That uncertainty sits underneath a lot of financial decisions, even when we don’t name it. Most of us carry two fears at once. The first is spending too freely now and running out of money later. The second is the opposite: saving for a someday that arrives too late, or never arrives at all, whether because life is short or because our health doesn’t hold long enough to enjoy what we put away.

Those two fears pull in opposite directions. Spend now and you risk the first. Defer everything and you risk the second. Most of the financial advice I come across leans hard toward one side or the other. What I keep looking for is a way to account for both at the same time.

A Different Way to Picture It

I recently listened to “Die with Zero” by Bill Perkins. His core argument is that we wait too long to enjoy the life we’re building, and that a lot of us die with money we never converted into anything that mattered to us.

Two of his ideas stuck with me. The first is to think of your life in buckets of time, say five-year increments, and to make sure each bucket holds some of the experiences that bring you joy rather than saving them all for the end. The second is what he calls “memory dividends,” which I’ll come back to.

I don’t agree with everything in the book, and I’m not interested in literally spending down to zero. But the bucket idea is useful to me for a reason Perkins doesn’t emphasize as much. It’s a way to account for both fears at once.

Why Spreading It Out Works

There’s a reason clustering your best experiences into one stretch of life doesn’t work as well as you’d think.

When I was a kid, the years all blended together. But my family remembers one of them clearly. They remember it as the year I was eleven. Almost every major childhood story we repeat when we get together seems to have happened that year. Strangely, that doesn’t seem to be the case for my brother and sister. For whatever reason, my eleventh year got packed with the kind of moments we still talk about.

As an adult, I’ve noticed there are diminishing returns when your greatest hits all happen at once. A once-in-a-lifetime trip feels less rare when another one happens a few months later. But the opposite is just as real. Delay those experiences too long and some of them never happen at all.

Spreading them across the buckets is the hedge. If life turns out short, you’ve already been collecting moments along the way rather than banking them for an end that didn’t come. If life turns out long, you haven’t blown through everything early and left the later decades empty. You don’t have to spend everything now, and you don’t have to defer everything either. Each bucket gets a few moments worth remembering, and the balance between now and later stays intact.

Memory Dividends

This is the second idea that stuck with me, and it’s the part that keeps paying you back long after the money is gone.

A memory dividend is what you get when a past experience comes back to you. A story, an image, a familiar scent or taste can pull you straight back into a moment you lived years ago. The experience keeps paying out, again and again, for the rest of your life.

Some of those dividends cost nothing. When I’m out for a walk on a brisk day and catch a whiff of smoke from a chimney, I’m transported back to being a kid getting ready to go sledding on a snow day.

Others were paid for. The smell of sage takes me back to sunrise Jeep rides on safari in South Africa, where the wild herb grew everywhere. The taste of a particular wine brings me back to my first trip to Napa, and the evenings spent sharing the bottle with friends by the fire.

And then there’s the one I come back to most. Hearing about someone’s wedding, or seeing a photo from my own, brings me right back to my wife and me dancing alone outside together on the portico of our venue toward the end of the night. The portico was only available to us because we paid an extra fee. The photo I have of that moment exists because we hired a photographer who was a little outside our budget but was willing to stay a little later into the reception.

That memory will stay with me forever. Jamie and I both think of it often when we find ourselves having a quiet moment together.

What This Looks Like in Your Own Life

It’s easy to read this as permission to spend, and that’s not quite the point. The bucket idea only works because it respects both fears. The money still has to last. The future still matters. What changes is the recognition that the future isn’t the only thing that matters, and that some experiences only pay their dividends if you actually have them.

Rather than looking back and judging whether you’ve spent the last decade well, it’s more useful to look forward. Think about the bucket you’re in right now, the next five years or so.

What are the experiences you’d want this stretch of your life to be remembered for?

What are the memory dividends you’d want paying out twenty years from now that you haven’t set in motion yet?

It’s worth saying that these don’t have to be trips, and they don’t have to be expensive. The dividends that matter most are personal, and they look different for everyone. For some people it’s a hobby taken up seriously, or a tradition built with the people they love, or time spent on something close to home that they never seem to regret. The chimney smoke from a childhood snow day didn’t cost anything and yet is still paying out.

Others will cost more than feels comfortable in the moment. The portico fee and the photographer felt like a lot at the time. They’ve paid us back many times over since.

That’s the tradeoff worth weighing. Whether each bucket of your life is getting a few moments worth remembering, without robbing the buckets still ahead of you.

— Brad

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This is meant to help you think through financial decisions and tradeoffs—not tell you exactly what to do. It’s general in nature and not personalized advice (see full disclaimer).

As you can probably tell if you’ve been a regular reader of mine, I have no shortage of things to say about personal finances. My wife, Jamie, will strongly attest to exactly that, since I’ve bored her on countless mornings with my financial dreams, plans, and updates.

But there’s a difference between talking about your finances with your partner and giving them a road map they can follow if you aren’t there to lead the discussion.

Most relationships split household duties. Rarely evenly, and rarely by formal agreement, but there are tasks where one of you pulls more weight than the other. Doing the dishes, laundry, cooking, yardwork, repairs, weekend planning, trips to the store, driving the kids around, taking the pets to the vet.

None of it is set in stone, but we slip into routines. And when the person who usually handles one of those jobs misses a week, their share of the work piles up. Dishes in the sink. Laundry on the chair.

It’s just as common for one person to handle most of the finances, even when both are contributing income to the household.

Here’s the important distinction:

If something happened to the person who handles most of the cleaning, things would pile up for a while, but the other could still get through their day.

If something happened to the one responsible for the finances, things could come to a standstill.

Whether you handle most of the money or you’ve delegated that responsibility, take a moment to picture a scenario whose likelihood is not zero percent: the unexpected loss of the partner who oversaw the finances.

Within days the surviving partner is trying to piece together what happened and what it all means for the future. Then the realization hits. They don’t know where anything is.

How can they access the accounts without the correct login information? Even with it, are they listed as an owner on the account? Were they named as a beneficiary when the forms were filled out 5, 10, 30 years ago?

This is a scary, but all too real, scenario. And it cannot be fixed after the fact. It has to be confronted ahead of time, and no time would be better than now. I promise you that.

I had let this slip on my end. Jamie is aware of the various accounts we have. We use an app where I’ve linked all our accounts, so she knows which ones exist, and she uses a password manager that helps with accessing them. But if I’m being honest, I haven’t done my part of keeping it updated so all my accounts are stored there too. I also haven’t saved our financial plan document somewhere she can readily reach it.

I’ve allowed myself to let those items slide, in part, because I know Jamie is fully capable of stepping into managing our finances on her own, or of finding someone trustworthy to advise her. That is not the case in every household.

If your partner would be starting from zero, or wouldn’t know where to turn without risking being taken advantage of, then the list of trusted names and the copy of the plan move way up the urgency list. Which is why I’ve come to think of this as two tiers rather than one long to-do.

One thing worth knowing before the list. For retirement accounts and life insurance, the beneficiary form on file generally determines who receives the money, even if your will says something different. A will signed last year may still lose to a beneficiary designation filled out twenty years ago. That’s why confirming those forms sits in the first tier, while the will itself can wait for the second.

So here’s what I’m working through in our own household, starting this week.

The don’t-leave-them-locked-out list (Tier 1):

1. Make sure both of you know where every account lives and how to log in, with that information saved somewhere safe and protected. And don’t forget the devices, email accounts, or authentication apps needed to actually get in.

2. For everyday accounts, like checking and savings, confirm you’re both listed as owners so either of you can act. If an account only has your name on it, ask the bank what your partner would need in order to access it.

3. For accounts that can only have one owner, like a 401(k) or IRA, confirm the beneficiary on file is the person you would choose today, or update it. It usually takes minutes.

And the make-the-hard-days-easier list (Tier 2):

4. Share, in a protected but reachable place, the additional planning information a surviving partner would benefit from. Include the names of anyone you’d trust them to reach out to for financial or personal matters.

5. Complete a will, and alongside it an advance directive covering how you’d want to be treated in certain medical situations, plus any funeral wishes. They’re separate documents answering separate questions, and both spare your partner from guessing.

I can’t imagine how difficult those first few days would be when someone loses their partner. Their person. And I hope I never have to. But I want no part of adding to that grief the stress and fear of being locked out of a checking account when the heating bill, the mortgage payment, and the funeral arrangements all come due.

There you have it. About an hour of your time could help your loved ones get through the hardest days of their lives. Dishes can sit in the sink for a week. This can’t. Don’t let it pile up and become their problem to deal with.

— Brad

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This is meant to help you think through financial decisions and tradeoffs—not tell you exactly what to do. It’s general in nature and not personalized advice (see full disclaimer).

Apparently, Mike and Abby had accumulated a handful of rental properties. They had the cashflow to stop working and let their rental income cover their living expenses. Sounded nice, but it did come with some headaches. Mike was on and off his phone during much of our conversation, dealing with a new tenant trying to access one of their properties. And Abby mentioned not all their properties had been profitable. There were some learning opportunities along the way.

While I haven’t ventured into rental property ownership in my own financial planning, I do see why it’s appealing to some. The potential for tax savings that aren’t available to a W-2 earner such as myself, the opportunity for large property appreciation if you find yourself in the right location at the right time, and the allure of using a property in a desirable destination as a future primary residence or vacation home once it’s all paid off.

That last one is particularly exciting for Jamie and me. Just about every time we travel somewhere, we talk about what it would be like to buy and live there on a more permanent basis. Something about imagining it adds a new dimension to each trip. Grabbing a bagel and a coffee at a local shop brings up questions like: how long would it take before the person working the register recognized me, and would we be on a first-name basis?

Living in the DC area for the last couple of decades, I do find myself longing for that local feel and connection that often seems easier in a smaller community. But owning a rental there wouldn’t guarantee any of it. Some owners never visit their properties except when a tenant has an issue or repairs are needed. And in plenty of destination towns, there’s often angst between locals and the owners of short-term rentals. The welcome I keep imagining won’t just happen because I buy a place.

That’s when I noticed something about the daydream. It has nothing to do with the investment. When I picture the bagel shop, nothing in that picture involves occupancy rates or repair budgets. I’m pricing a lifestyle. The rental property fantasy bundles two very different purchases together: an investment that needs to earn its keep, and a story about who I might become. It’s easy to pay for the story while telling yourself you bought an investment.

Not every rental investor does this. Some buy commercial buildings or homes in markets they'll never live in, chosen because the numbers work and for no other reason. For them, the property is a business from day one. What follows is for the rest of us, the ones who catch ourselves pricing a lifestyle while telling ourselves we’re pricing an asset.

Strip the story away and look at what’s left. A rental property is a small business with a big, illiquid price tag. Rental income looks passive on a spreadsheet, but Mike’s phone kept lighting up at the bar. He and Abby stepped away from their careers and into a part-time job with no boss, no PTO, and the occasional tenant lockout on a Monday night. Some people genuinely want that job, and there’s nothing wrong with that. Abby’s comment about unprofitable properties fits the same picture. Small businesses sometimes lose money, especially while the owners are still learning the trade.

Once the investment case had to stand on its own, it didn’t win for me. It came down to three things.

1. What you’d need to know. Buying a rental means understanding a specific local market. What properties rent for, how many days a year they’re occupied, how quickly they sell, and whether future development or environmental issues could keep the property from appreciating or renting as anticipated. A broad-based index fund asks none of that of me. I just need the overall market to keep doing what it has historically done over long stretches of time.

2. Access to the money. A rental keeps a good bit of cash locked up for weeks, months, or even years before it can be turned back into dollars I can spend. It also demands cash reserves for extended vacancies, major repairs, or improvements. The money I invest in index funds mostly stays reachable if I need it. Try that with a down payment.

3. Taxes. Real estate has a powerful toolbox: depreciation deductions, deductible expenses, and 1031 exchanges that can defer gains when the rules are satisfied. Index funds offer a different kind of tax efficiency: low turnover, preferential tax rates, and the ability to hold them inside tax-advantaged accounts like 401(k)s and IRAs. It’s a question of which rulebook you’d rather learn, and I’ve already spent a good bit of effort on the latter.

In fairness, there’s one place where the rental math can genuinely pull ahead: leverage. Put twenty percent down and you collect appreciation and rent on the property’s full value. That’s one of the real engines behind most rental wealth stories, and it’s the honest answer to why some investors do far better with property than they ever would in an index fund. Of course, leverage runs both ways. A leveraged property that sits vacant or drops in value loses money faster than an unleveraged one ever could.

So I continue down what I consider the simpler path, while admitting the stock market can be made to look a lot more complex than buying and holding an index fund for the long run. I expect to keep revisiting this decision anyway. I have a bit of an obsessive personality and often beat a topic to death long after Jamie has tuned me out. Future me may feel differently than current me, and there’s nothing wrong with keeping myself honest about the why behind decisions this size.

Go back to that bagel shop. Index fund money can buy me the coffee there someday, with no tenant calling in the middle of it. What it can’t buy is the thing I actually wanted, which was to be a local. To be recognized and have the person at the register ask what we’re up to that morning and actually care about the answer. A visitor rarely gets that no matter how the trip was funded.

And here’s the harder truth: neither does the owner.

I could buy the property and still be an out-of-towner with a key. Even if we moved there for good, we’d be new locals, not people with a real history in the place. That feeling I was longing for was never for sale. It only comes from years of actually being somewhere, and no down payment shortcuts the years.

So strip away the life I’m imagining. Is what’s left something money can actually deliver, or have I been pricing a feeling that no asset was ever going to hand me?

— Brad

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This is meant to help you think through financial decisions and tradeoffs—not tell you exactly what to do. It’s general in nature and not personalized advice (see full disclaimer).

I’ve always liked nice things. I was definitely the ‘girlie girl’ growing up. I did not, however, grow up with money. We were comfortable for our small town, but while I loved pretty things and shopping trips, I wasn’t an “Abercrombie girl” like some of the others in my class. But I did have a generous grandmother who would take me back to school shopping every summer — a true highlight of my year not only for the shopping spree, but for the time and fun we had together on those trips. She also loves to shop, so I got it honestly.

My mother also loved shopping, and in the earlier years when money was tight, she would get into some financially precarious positions because of it. So while I enjoyed the occasional splurge trip with my grandmother, I was also cognizant of the fact that the bill comes due at the end of the month, interest piles up quickly, and I shouldn’t buy something if I couldn’t afford to pay for it within the month.

Growing up in a small rural area also meant that my concept of ‘nice’ or ‘expensive’ was different than what it is now, living in a high-net worth metropolitan area. I consider myself lucky that I grew up in a time without social media, where the exposure to people with seemingly limitless money and fancy things was nonexistent. My comparison was the other kids at school and what I saw in my Seventeen magazine. My dream wardrobe came from the Delias catalogue, rather than an influencer peddling a wardrobe worth more than a teacher’s annual salary.

While that was my early life experience, my world view expanded substantially when I moved to DC, where a whole new world of luxury was suddenly in my face, and my budget did not match what I was seeing and starting to desire. My $25,000 staff assistant salary didn’t even cover rent — I was fortunate to have my parents subsidize me for a bit until Brad moved to DC and moved in with me. That didn’t stop the growing desire for nicer things though. I was suddenly exposed to lobbyists, consultants, and business owners rolling through my office with designer bags, shoes, and clothes. I have always enjoyed fashion, and I view my wardrobe and how I present myself as a core part of who I am. Perhaps that’s vanity, but I have always been very attuned to how people are treated based on how they look and dress, and I believe in putting my best heel forward. I want to ensure my first impression is a good one, and my look is a big part of that.

That desire to look fashionable and my love of shopping did get me in a little bit of trouble here and there — a credit card balance I couldn’t pay off at the end of the month and had to carry over to the next, pulling a bit more from my savings to cover it, or, much to the detriment of my pride, having to tell Brad I overspent and needed him to cover more than his half of our living expenses for the month.

Those conversations were the worst, not for anything he said, but for my own sense of self. For as much as my look is a part of who I am, I was also good with money and despised feeling like I made a mistake and let down my partner.

These conversations, as much as I hated them, did help Brad and me build a healthy relationship and communication style, as well as set the foundation for how we would manage budgets and financial decisions together.

Our financial styles and goals are a bit of a push-pull, depending on the area. I lean toward spending and enjoying our hard-earned money now, while Brad has been the more conservative spender, preferring to put more away for later. It doesn’t work that way on everything, and over the years, we have rubbed off on the other.

I understand the value of saving for our future, setting ourselves up for a fulfilling retirement and giving ourselves the flexibility to quit working when we want to, versus having to wait until we can. Brad has learned from me there is sometimes value in higher quality items, presenting oneself well, and spending money on things we enjoy now (travel being the most obvious).

This has enabled us to find a good middle ground. But, as our salaries have increased, so has our spending. Our baseline of what is “quality” or what is even just “acceptable” has continued to rise. 15 years ago my requirement for a hotel was a safe location and clean room.

As I’ve experienced luxury hotels thanks to my career, my wants have gone up. What was once a decent hotel suddenly looks a bit underwhelming next to what work travel has shown me. So our conversations focus on balancing the needs with the wants and determining what is worth the cost.

When Brad and I were in college, I really wanted a quality ‘investment’ bag. Something that was neutral, leather, classic, and would last. At that point, I decided it was a $350 Coach bag. For someone whose nicest bag probably cost a third of that, it was a big jump. And for Brad, whose mom’s handbag was for schlepping around all the kids’ stuff, it was almost absurd.

Regardless of his opinion on the matter, he knew it was important to me, and after a summer living with his family and helping them build their patio, Brad and his mom surprised me with the bag. It meant the world to me, not just because I got the big-ticket item I was dreaming of, but for what I felt it said about how they felt about me. I loved that bag and I carried it for years.

Eventually though, the bag fell out of style, and other desires took its place. But it wasn’t a different Coach bag, or something around the same price point. The ‘hero’ items on my wish list rose in cost as my exposure to higher end goods expanded. The Coach bag became a Prada tote. The Tory Burch flats became red bottom heels. As income grew, so did the wish list.

To this day, Brad keeps a running list of these things (which makes him an excellent gift giver). While it would be easy to let this run out of control, we’ve both been cognizant of the fact that these are special purchases and gifts and not meant to be the baseline for everything we own. That perspective has been important to both of us. Neither of us wants to see a day where these things are no longer special.

Even keeping this perspective in mind, I do suffer from ‘lifestyle creep,’ and it can be a challenge to keep it in check. In all honesty, I can come up with a way to justify any of my higher end purchases, but should I? Or should I finally hit the point where good enough truly is good enough? When do the expectations stop ticking up?

There’s a sweet spot between what we used to be able to afford, what we can afford, and what we should spend. Managing that push-pull is a constant negotiation not just between the two of us, but within ourselves as well.

Trying to maintain the self-awareness of why we want things and how we decide to satisfy those desires goes a long way in making sure we aren’t blindly allowing a ‘keeping up with the Joneses’ mentality to totally overwhelm us. It’s easy, especially in this hyper-visual world, to let it creep up and overtake us.

Trying to keep things in perspective has allowed me to truly appreciate what I have, enjoy those ‘wish list’ surprises and purchases, and not get lost in the ‘next best thing’ cycle (though it does happen from time to time), which is a losing battle regardless of how much money you have.

- Jamie

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This is meant to help you think through financial decisions and tradeoffs—not tell you exactly what to do. It’s general in nature and not personalized advice (see full disclaimer).

The risk of running out of money is real and should be taken seriously. Most financial advice is built around that idea for a reason, and any serious financial plan should build ways to navigate it.

But that’s not the risk I’m concerned with here.

You can spend years building a plan that works perfectly on paper and still end up extending your working years well beyond what’s actually required. Or give up experiences, comfort, and flexibility along the way because the plan demanded it.

Most people don’t arrive at an overly cautious plan through a single decision. They arrive through a series of small ones:

• Lower withdrawal rate.

• A bit of extra cushion in your spending.

• More conservative assumptions on returns.

Each one makes the plan feel more secure. And each one moves the target further out.

Taking a conservative approach isn’t a problem. Being conservative in multiple places might be.

When Caution Compounds

Most of these decisions are made independently, and each one has a reason behind it. But when every assumption leans in the same direction, the combined effect can be more than the plan was meant to carry.

The target gets higher. Spending gets tighter in the present. Experiences get delayed.

Plans get pushed to “later” without much thought given to what later actually looks like, or whether health and circumstances will allow for the same things.

I caught myself doing this in my own planning. I’d lowered my withdrawal rate to build in margin, added cushion to my budget estimate, and assumed higher taxes just to be safe.

Each decision had a reason behind it. Together though, the years needed to reach FI had grown more than I’d expected. My response was to increase my annual savings goals and reduce expenses.

I was reshaping the plan I actually wanted in order to fit the one I’d built. It should have been the other way around.

That was a bit of a wake-up call. My priorities hadn’t changed, but I’d layered one cautious assumption on top of another without accounting for where they’d land together.

A lot of us could be over-saving because we’re unsure.

Every Layer Has a Price

A lower withdrawal rate needs more saved to cover the same spending. A larger cushion for expenses raises the annual baseline you’re working from. More conservative assumptions push the entire plan further out.

All of that increases certainty. It also reduces flexibility, both in how long the plan takes and in what it allows along the way.

For me, a lot of it came down to not wanting to get it wrong. I handle most of our financial planning and reaching FI has always been more of a priority for me than for my wife. She’s likely to want to work well into her 60s, and I hoped to have the option to walk away long before then. The last thing I wanted was for my timeline to become her problem, or to cost her something she hadn’t agreed to give up, if I miscalculated.

What I didn’t account for was how each cautious decision made the next one easier to justify. By the time I stepped back and looked at what they added up to, the plan had drifted well past what either of us actually needed.

There’s nothing wrong with building margin into a plan. That said, it’s worth asking how much of it is really required, and whether it’s concentrated in the right places.

If multiple decisions are providing safety, it’s worth asking which one actually needs to carry that weight.

Once It’s Gone, It’s Gone

Financial independence planning is often framed as a problem of not saving enough. The version that gets less attention is the plan that asks for more than it needs to. More time working, more saved, and more given up along the way because the decisions it’s built on were never examined together.

A plan can be adjusted. Assumptions can be revisited. Decisions made with incomplete information can be updated as things become clearer.

What it can’t do is return time that’s already passed.

That’s what I’m revisiting now. Whether the tradeoffs the plan is asking for were actually chosen, or whether they just accumulated, one reasonable decision at a time.

— Brad

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This is meant to help you think through financial decisions and tradeoffs—not tell you exactly what to do. It’s general in nature and not personalized advice (see full disclaimer).

One of my favorite things to do on a beach vacation is enjoy my morning coffee outside. As seems to happen to all men in their 40s, I’ve become an amateur birder. Sipping strong coffee, listening to the birds, and enjoying the morning before the sun starts beating down with that summer heat is just about as good as it gets to me.

The realization that our rental had no coffee maker was a bit of a bummer. Luckily, we live in a time where just about anything can be delivered, often with free shipping, within a matter of days. Sometimes within the hour. I opened my phone, scanned Amazon for the cheapest coffee maker, and saw it was available for $28 and could be delivered between 7-11am the next day.

I let the group know I’d solved our problem, though none of them seemed to have even gotten to the point of caring about tomorrow’s coffee. But in my mind, I was a hero. Just as I was about to hit add to cart and buy, Jamie said, “Don’t buy a coffee maker. That makes no sense.”

That was the first time since I worked out the coffee problem that I questioned whether it made sense to buy a coffee maker for a long weekend or just plan to go find coffee each morning. So like the accountant I am, I did the math.

Eight adults, three mornings. Even if the coffee maker couldn’t be delivered in time for the first morning, we’d still use it at least two mornings, possibly three, with potential for any afternoon pick-me-ups too. We were likely looking at anywhere from 16-24+ cups of coffee.

For a $28 coffee maker, my cost per coffee would be $1.75 or less. Hard to find a cup of coffee as cheap as that anymore, so the math for buying made sense.

Beyond the math, the coffee would be available whenever I wanted it, at the home I was staying in, and refills were only limited by the amount of coffee grounds I had on hand. Seemed like a no-brainer to me.

I explained to the group I’d done the analysis and it made sense to just buy it. They were almost paying attention to our coffee problem at this point, and I may have heard at least one person agree. So I added to my cart and purchased.

The next morning, I was waiting for the coffee maker to be delivered when one of the others in our group happened to find a coffee maker hidden in the downstairs bathroom closet.

The coffee maker had been there the whole time.

I’d done a quick sweep of the kitchen but had stopped looking that hard once just ordering one seemed easier and more convenient. The truth is, the cheapest and most convenient option would have been to find the coffee maker that was already there.

In my defense, the downstairs bathroom closet is not the first place most people would look for a kitchen appliance. But I also hadn’t looked especially hard, asked the rest of the group to help, or contacted the owner to see whether one was available.

Once I saw that another coffee maker could arrive the next morning for $28, continuing to search no longer seemed worth the effort.

Have you noticed how much convenience has changed our threshold for effort?

A short drive begins to feel like too much when delivery is available. Waiting a few days feels unreasonable when next-day shipping is an option. Looking for something, repairing it, borrowing it, or asking whether someone else already has one can feel like more work than simply buying another.

There is real value in convenience. Money is not the only limited resource in our equations. Time, energy, patience, and attention matter too.

Financial independence shouldn’t require us to perform every task ourselves or choose the cheapest possible option. Part of the reason many of us want financial flexibility is so we can spend money to make life easier when doing so is worthwhile.

But be careful. Being just a few clicks away makes it easy for us to default to convenience. Think about how many ongoing subscriptions you may have. The grocery and food delivery services. The Prime and next-day delivery fees. Ride-sharing and streaming bundles.

We’d all be surprised how much we spend on convenience throughout the year. And the future is only going to continue to get more convenient with less effort.

If you haven’t thought about some of those convenience charges you might be paying each month, start with the big-ticket items and work your way down. If the value exceeds the cost, and you have the flexibility in your budget, no worries. But if things feel a little tight or you feel like your money isn’t working for you as much as you want it to, this is an area that could free up some cash.

Don’t be too quick to just go with what feels convenient at the time. Likewise, don’t overburden every decision you make out of convenience. You don’t have to analyze and justify everything. Sometimes convenience is just that.

Yes, this level of analysis was a bit of overkill for my morning coffee concerns, but the general point is still beneficial for most things where we’re quick to sign up, add to cart, or swipe on a card.

A little more effort on my end may have solved the problem for me for free, but who knows if I ever would have thought to check the bathroom closet on my own.

Luckily, I have free returns and was able to send the purchased coffee maker back without even opening the box. Just one more convenience that sometimes can do more harm than good.

But I’ll take it this time.

— Brad

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This is meant to help you think through financial decisions and tradeoffs—not tell you exactly what to do. It’s general in nature and not personalized advice (see full disclaimer).

There’s a point where your investments are growing, your savings are consistent, and things are clearly moving in the right direction.

If you're not here yet, you will be. When you get there, you’ll expect it to feel different than it does. More certain. More settled. Like something has been figured out.

I remember the first time our investments hit $100K. I noticed it, felt good about it, and mentally moved on to $250K. That came and went too. On to the next.

I’m not going to pretend each milestone didn’t bring real excitement. But each one also left the same question sitting there.

The uncertainty didn’t go away. It just changed.

The Uncertainty Doesn’t Disappear

Early on, the uncertainty is fairly straightforward.

Will I be okay? Am I saving enough?

That starts to ease as savings grow. There’s more margin, more distance from a bad situation. But something else begins to take its place.

A few years after my wife and I moved into our home, things started to feel more settled. We had built something. The basics were covered. And that’s when we started having real conversations about what we were actually building toward.

We expected it to be easy to identify at that point. It wasn’t.

We disagreed here and there. Had different priorities occasionally. Still do. But we knew it was important to start looking at things with more intention, even without a clear answer.

The uncertainty hadn’t disappeared. It had shifted. From whether we’d be okay, to what okay was actually supposed to look like.

When the Decisions Change

As the margin grows, the decisions start to look different. The question moves from whether to spend to which options to pursue.

I’ve noticed this when trying to keep the pedal down on saving. When you’ve built a cushion and feel more secure, there’s a pull toward letting up a little. Maybe that’s even the right move at some point. But it’s easy to get distracted from actual goals when there’s money that could go toward extras instead of just covering the basics.

Adding another trip is easy to justify when you’re ahead of your savings target. But that assumes things will keep moving in a straight line. Investment returns, health, and circumstances rarely do.

The other place I’ve felt this is the home. My wife and I keep coming back to whether we should upgrade. We've stayed in our current place intentionally. The lower fixed costs give us the flexibility we both value. But a bigger home has become something we could actually make work now. That possibility has a pull to it that didn't exist before.

What Actually Changes

The decisions stayed the same. Having more cushion changed how I was willing to answer them. The bigger question of what we're actually building toward is still just as open as it ever was.

I used to be pretty rigid about spending, and saw it as something to minimize. My wife was the one with champagne tastes. I was the one trying to keep us on a beer budget.

I’m not sure exactly what shifted. Maybe it was Covid or my more recent back flare-ups that changed the way I thought about time. Maybe it’s where we sit financially now and the cushion that comes with it. Maybe my wife has rubbed off on me more than I’ve admitted.

Probably all of it.

I’m still always going to prioritize the future. That hasn’t changed. But I’ve found a more balanced approach with the present than I had ten years ago.

For years I kept our travel budget flat. Most of every raise or bonus went toward the future. More into savings, more into the brokerage account. The last couple of years that’s changed. A bigger portion of pay raises have started going toward the travel budget instead.

Some of it was practical. Inflation and preferences for slightly nicer places had made the old number feel tight. But some of it was intentional. A conscious decision to make sure we were investing in now too, and not just a future version of retirement where we hoped to travel. Our bonuses still mostly get deferred to the future. But the raises shifted, and that feels more aligned with where we are and what we want.

The number still matters. I just started paying more attention to what it was actually for.

More money gave me the ability to ask that question more honestly. It didn’t answer it.

That part is still mine to figure out.

— Brad

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This is meant to help you think through financial decisions and tradeoffs—not tell you exactly what to do. It’s general in nature and not personalized advice.

The decisions I make around financial independence (FI) are not just mine. I share every input that goes into my own FI equation with someone else.

I met my wife, Jamie, during our freshman year of college. We dated, graduated, moved in together, and got married about seven years in. Every stage of our relationship required decisions that impacted both our futures, financially and otherwise.

In school we had both wanted to study abroad, but I couldn’t make it work. I needed to graduate with a certain number of credits to eventually get my CPA license, and going abroad would have left me short unless I stayed for a fifth year.

Jamie was not thrilled when I told her I couldn’t make the semester abroad work.

She decided not to participate in the study abroad program either and chose another program that allowed her to spend a semester in DC for an internship. We were three hours apart that semester, but I was able to drive from Pennsylvania to DC to visit. It’s how we both started to fall in love with the DC area.

Jamie’s internship led to her career, so things worked out. She has almost forgiven me for skipping the study abroad program.

There was nothing saying Jamie couldn’t have gone abroad on her own. Or that I couldn’t have stayed a fifth year to make up for the credits. Nothing that said I couldn’t have changed my career plans entirely and done something other than becoming a CPA.

Any of those choices could have made sense.

But in the end, we made the decision together. We committed to each other, and that meant sacrificing, listening, and trying to understand one another.

What does this have to do with financial independence?

At the time I thought the ‘financial decision’ was the cost of going abroad and the extra year of school. But in hindsight, this was the decision everything financial got built on. The place we’d live. The careers we’d have. Whether I’d get my CPA. It even pushed us toward making those decisions together.

We didn’t know it then, but we were shaping our financial future before we had ever made a budget together.

That decision worked out. Plenty don’t. And sometimes the difference is not just the decision itself, but who you are making it with, how honestly you are making it, and whether both people are willing to carry the consequences together.

A couple’s financial future is not just about combining accounts. It is about combining direction and being the person your partner needs beside them.

My parents recently celebrated their 50^th wedding anniversary. When I told my dad I was going to start writing about the decisions around financial independence, his first comment was that I should make sure to talk about the importance of sharing and discussing financial decisions with the person you are building a life with.

This is the start of my efforts to address his request.

More to come.

— Brad

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This is meant to help you think through financial decisions and tradeoffs—not tell you exactly what to do. It’s general in nature and not personalized advice (see full disclaimer).

I didn’t think much about heating bills growing up. Then I moved into a house in college with three roommates and got my first real introduction to what an unpredictable one looks like.

The first cold month of the year came with a huge heating bill. So we lowered the thermostat to 60 and wore layers indoors. Friends who visited thought we were living in a refrigerator.

I even tried lighting thirty candles in my room once hoping they’d generate enough heat to make a difference. The smoke got to be a bit much and the fire hazard potential became pretty obvious pretty quickly.

Still, the heating bills came in shockingly high. We later figured out the heat vent was positioned directly below the attic, which meant the furnace ran constantly without ever really warming the house.

We’d split the bill four ways and still each feel the hit. There wasn't much we could do about the vent or the furnace. We just paid it and hoped the next month would be better. It usually wasn't.

That’s how financial spikes work. You know they’re coming in some abstract sense. But when the bill actually arrives, the amount still lands like a surprise.

Years later my wife and I bought our first townhouse and the same feeling came back. She’d see a bill come in and turn to me, “hey, we have to pay this” and I’d feel that immediate anxiousness. Not panic, just the extra stress of figuring out where the money was coming from and whether anything else needed to move around to cover it.

It wasn’t that we didn’t have the money. It was that the money wasn’t where it needed to be when it needed to be there.

The same thing happened with car insurance, holiday spending, and anything else that hit once or twice a year in amounts that felt larger than a normal monthly expense. The math worked out fine over the course of a year. The timing didn’t.

The fix isn’t complicated. It’s just moving money in smaller, more consistent amounts before the bill arrives instead of scrambling to find it after.

For utility bills, many providers offer average or budget billing—a monthly amount based on your typical usage rather than the prior month’s actual consumption. The amount adjusts slightly over time to true up, but the swings disappear. For anyone in a place where a $300+ heating bill hitting in February creates real stress, it’s worth a phone call or a few minutes online to set it up.

For larger periodic expenses—car insurance, holiday spending, anything that arrives once or twice a year—the same logic applies. Divide the annual amount by twelve and move that amount into a separate account each month. When the bill arrives the money is already there. The surprise is gone.

You don’t need a separate account for every category. One account for irregular expenses covers most of it. The point isn’t the account structure. It’s the monthly habit of moving a small amount before you need it.

My wife and I have had a dedicated travel account for over fifteen years. We both contribute to it monthly. When we travel, I transfer from it. When my wife travels for work and needs to cover expenses before reimbursement comes through, it’s there.

We also use it for things that are part of how we travel. In Florence, I bought a leather jacket I hadn’t planned on. It was more than I’d ever spent on something for myself at that point, but we’d saved specifically for the trip and I wanted something that would mark the occasion, our honeymoon. Having the account meant I could say yes without second-guessing it.

What I’ve noticed over time is that the account does something beyond just covering expenses. The balance tells us what kind of travel year we can have. If it’s grown, we can take on something bigger. If we’ve had an active year, we know to pull back a little on the next one. It turned a recurring source of financial stress into something I actually look forward to managing.

That shift, from reactive to intentional, is what smoothing the spikes actually gives you.

None of these are complicated adjustments. They don’t require a new app, a financial advisor, or a perfect budget. They just require moving money in smaller amounts more consistently so the spikes stop feeling like surprises.

The stress that comes with a big unexpected bill isn’t usually about the money itself. It’s about the timing and the feeling of being caught off guard. Fix the timing and the stress tends to go with it.

What’s the next bill that’s going to catch you off guard? Whatever it is, you probably already know it’s coming.

— Brad

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This is meant to help you think through financial decisions and tradeoffs—not tell you exactly what to do. It’s general in nature and not personalized advice (see full disclaimer).

Time is doing the heavy lifting there, and time is one of the most powerful forces in any financial plan. The catch is that you don’t fully control it. You can’t reclaim the years before you started, and choosing to retire earlier shortens the runway rather than extending it. Most of your time is already set by when you began and when you want to stop.

Your savings rate is different. It’s just as powerful, and unlike time, it’s a lever you can still pull at almost any age. Part 1 looked at where the conventional 10-15% guidance came from and who it fits. This post is about the lever itself, and how to read what it’s doing for you.

Think about how a working life tends to unfold. You might start with debt to pay down and an income well below what you’ll earn later. Then the bigger expenses arrive: housing, family, repairs and emergencies.

Retirement savings gets pushed back, then pushed back again. For a lot of people, the early years simply don’t allow much. That’s exactly why the savings rate carries so much weight. It’s the input you can adjust once your situation allows it, at almost any age.

Working Both Sides at Once

By now you’ve hopefully found a recurring gap between what you earn and what you spend. That gap is your maximum possible savings rate, the ceiling on what you could set aside. What you save is a choice you still have to make. The gap only becomes a savings rate once you direct it toward the future instead of letting it sit or spending it elsewhere.

Once you’re saving it, that rate does more than any other input you control to determine whether and when you can stop working.

What makes it so powerful is that it works on both sides of the equation at the same time.

Every dollar you save gets time to grow, and as the opening showed, time does extraordinary things to a dollar.

Then there’s the other side. The more you save, the less you’re living on. And the less you live on, the smaller the pile you need before you can walk away.

A higher savings rate lowers the target at the same moment it speeds you toward it.

What That Looks Like in Dollars

Say your gross income is $80,000 and you save 10% of it. You’re setting aside $8,000 and living on $72,000. If you expect similar spending in retirement, you’ll be funding roughly that $72,000, 90% of gross income. Using the common benchmark of 25 times your annual spending, your FI number is $1.8 million.

Now raise the rate to 15%. You’re saving $12,000 a year instead of $8,000, and you’re living on $68,000, 85% of gross income. You’re putting more away each year, and your FI number falls to $1.7 million, because you’ve shown you can live on less.

Saving more fills the bucket faster. It also shrinks the bucket you’re trying to fill. The same five-point raise did both jobs at once, which is the whole reason this lever matters as much as it does.

Find Your Own Savings Rate

You may already know your savings rate or have a vague idea. If you haven’t calculated it recently or want to make sure what you think you’re saving is right, use the Savings Rate Calculator.

It will help identify your current rate, including employer matches and other retirement contributions.

Most people couldn’t tell you their savings rate. Even fewer know what it’s buying them.

The number itself isn’t good or bad. It’s just an important step in seeing where you are, before figuring out if you need to adjust. A 10% savings rate might be exactly right for someone planning to work into their 60s. The same rate could limit someone hoping to leave full-time work by 55.

Every savings rate buys a different timeline. The question is whether yours is buying the one you want.

See What That Rate Buys

Now that you know your current savings rate, you can see if it aligns with the timeline you want. Open the FI Timeline tool and see for yourself.

It takes your age, gross income, savings rate, and what you’ve already saved, and shows roughly how long until financial independence (FI), where work becomes optional.

To keep the calculation simple and consistent, the tool does not include Social Security benefits. For many people, those benefits could meaningfully shorten the timeline shown.

Closing the Gap

If the tool shows a disparity between where you are and where you want to be, there are a few places to look.

You can raise your rate, saving a larger share of what you earn. That’s the lever this post has been about.

You can earn more, allowing the same savings rate to carry more weight.

You can move your timeline, accepting a later date and longer runway to grow your portfolio.

You can reconsider your target, asking honestly what kind of retirement you’re funding, and whether it needs to cost as much as you’ve assumed.

Which ones make sense for you depends on what you’re not willing to give up, and that’s not something a formula can tell you.

What Comes Next

Once you have a pace and a rough idea of where it's taking you, the next question is how simple or complicated you want the rest of it to be. More accounts, more strategies, more moving parts can all earn their place, but each one asks something of you in return.

If you haven’t checked out the FI Tools page on my site, please do. That’s where I’ll share free and interactive tools, like the two in this post. These tools are meant to help you work through your own FI equation and make clearer decisions with it. I’ll continue to build out additional tools, so keep checking back.

And you can always email me at brad@thefiequation.com if you have ideas or suggestions to improve any of the tools or content for the site.

— Brad

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This is meant to help you think through financial decisions and tradeoffs—not tell you exactly what to do. It’s general in nature and not personalized advice (see full disclaimer).

Whoever told you had a point but they didn’t have the whole picture. At best they handed you a starting point, a target, a benchmark to measure against. There’s just too much they couldn’t know: your trajectory, your priorities, how long you’ll live.

I don’t know those things about you either, and I won’t pretend to. That said, I do think it’s worth understanding where that number came from, because once you see what it was built to do, you can tell whether it was built for you.

Where You Heard It

The “save at least 10%” idea probably reached you through a parent, a teacher, or an HR rep handing out forms. Maybe an article about how unprepared most people are for retirement.

I remember filling out the 401(k) contribution line at my first accounting job. I marked 3%. A coworker who started the same week marked 10%. He was about ten years older, and when it came up, he gently pushed back on my number and suggested I make it more of a priority. He wasn’t trying to make me feel bad. He was passing along the same guidance someone had probably once handed him.

For me, that’s exactly what it did. It planted a seed. I left my contribution at 3% for the moment, and made a plan to raise it by at least a percentage point every year. The number itself mattered less than the nudge to start thinking long-term about where my money was going.

Why the Number Holds Up

The math behind 10% makes sense, for a particular set of assumptions.

Picture someone who starts working in their early 20s and plans to retire around 65, a career of 40 to 45 years. They likely won’t need to replace all of their pre-retirement income, since payroll taxes, retirement contributions, and the costs of working all fall away. Most planning lands on replacing 70 to 80% of pre-retirement income, with Social Security covering part of that and personal savings filling the rest.

Run those inputs over four decades of compounding, and a savings rate around 10% works for a lot of people. It’s the answer to a specific, reasonable question: how much do you need to save over a typical career to retire at 65 on something close to your current lifestyle?

Every Savings Rate Buys a Different Timeline

A savings rate isn't just a percentage of income. It's one of the biggest inputs determining how long you'll need to work.

One way to see this is to stop thinking about savings rate as a percentage and start thinking about it as time.

The chart below shows how long it takes to reach financial independence (FI) at different savings rates and starting portfolio sizes.

Start from zero and save 10%, and you can reach FI in about 44 to 46 years, roughly age 66 to 68 for a 22-year-old. Save 20% instead, and that drops to 33 to 35 years. That same 22-year-old could retire in their mid-to-late 50s. (An exit that early may need more than 70 to 80% replacement to bridge health insurance before Medicare, so treat the earliest numbers as a demonstration of the rate’s power more than a finished plan.)

This is why the guidance became standard: for someone who starts early and wants a traditional retirement, 10% genuinely works. Aiming for somewhere between 10-15% provides a little extra cushion for someone with a long time horizon to help if things don’t go as planned.

What About Those Starting Later

Most of us aren’t 22 anymore and likely didn’t save as much as we wish we had.

Fortunately, most of us aren’t starting from zero either.

The chart shows how much of a difference an existing portfolio makes. Someone saving 10% with 3× income already invested reaches FI roughly a decade sooner than someone starting with only 1× income.

Same savings rate. Different starting point. Different outcome.

That’s why late starters often need a higher savings rate than the traditional benchmark.

When the Question Changes

My dad once told me that during the years he was putting money away for me and my siblings’ college funds, there were stretches where our accounts held more than his own savings did. He couldn’t put as much toward his retirement then, because he was funding a different goal he cared about. He made up ground later. The point is that a lower rate at one point or another isn’t necessarily a failure. Sometimes it’s the right call for the life you’re living.

My own savings started slow. The 3% in my 401(k), a little toward an emergency fund, some other savings. My overall rate sat between 5-10% for a while, inching up each year.

It was a reasonable plan. Then I started wanting the option to stop working before my 60s while keeping the retirement my wife and I were already working toward.

That single change, pulling the date earlier, is what moved the math. If I’d planned to work longer, 10-15% would likely have funded the retirement I’m aiming for now. The driver was timing. I wanted the same kind of retirement, just sooner.

So I raised my rate. I kept increasing it each year, setting aside a portion of every raise and bonus so at least some of it went to long-term savings. That approach let my wife and me double our savings rate over each of the last two decades, helped along by careers that brought steady pay increases. Not everyone is in that position.

Here’s the part I have to stay honest about. The goalposts move. As a target comes within reach, there’s a pull to stretch further. When something becomes achievable, we tend to want a little more.

I’ve bumped up my retirement budget here and there. I weigh that increase against my current savings rate to determine if the tradeoff of needing to save more makes sense. For now, the balance between living today and funding tomorrow feels close to right. But I expect to keep revisiting it.

Rules of Thumb Are Answers. Check the Question.

The 10-15% guidance is an answer, and sometimes a good one, to a question you may or may not be asking.

Most financial rules of thumb work this way. Someone ran a calculation with reasonable assumptions and compressed the result into a number you could remember. Save 10% for retirement. Keep three to six months of expenses on hand for emergencies. Withdraw 4% a year in retirement so your money will last. These are all useful pieces of advice but might not always line up perfectly with your own FI equation. That’s why it’s worth the time to understand them and make some adjustments before you build a life around them.

You don’t have to settle your retirement vision today. It will move. Mine did and probably will again. What you have now is the ability to check, whenever you want, whether your pace and your destination still belong to the same plan. Most people never get that far.

Checking starts with a number: your own savings rate, measured the same way throughout this series, and what it’s actually doing for you. That’s Part 2.

— Brad

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This is meant to help you think through financial decisions and tradeoffs—not tell you exactly what to do. It’s general in nature and not personalized advice (see full disclaimer).

But there’s another version of getting this wrong. Some of us lean so far toward optimizing the future that we end up delaying the life we could be living now. Sometimes I find myself in this second group and have to pull myself back.

Living for the Future

There are decisions that clearly improve the outcome.

Saving a little more. Finding better returns. Lowering costs. Working a bit longer to build more margin.

Those decisions are easy to justify. They move things forward. Progress feels measurable. Like things are working.

And once something is working, it’s natural to keep leaning into it.

I’ve noticed that in my own decisions. It doesn’t even feel like an intentional strategy. It just becomes the direction things keep moving.

This is where optimization sometimes becomes a default decision-maker on its own.

If saving more is good, saving more than that must be better. If the plan is on track, tightening it up a bit more feels like the right move.

Over time, the focus shifts without really noticing it. Improving the outcome starts to take up more space.

But what tends to get missed is what you might regret later. If you reached your number tomorrow, would you regret how you spent today?

Even when not considering our finances, there are moments that might cause us to reflect on that same question. A sudden health scare. An aging parent’s decline. The loss of a friend.

Mine came on the side of a volcano. My wife and I were halfway up Mt. Etna, filming an eruption that had been building all morning, when the slow release of gas and ash we’d been watching turned into a thunderous explosion. We started running. I still have the video of the two of us scrambling for safety with the eruption going off behind us.

No one was hurt. It’s become one of those stories we tell often now, half disbelief and half laughter. But moments like that have a way of reminding you how quickly things can change.

Taking a Closer Look

Those moments have a way of making you look at your own decisions more closely. You take notice of where most of your attention has been going. What keeps getting pushed forward. What keeps getting delayed.

I found myself thinking about whether I had started to overemphasize one side of things without really meaning to.

Improving the outcome has real benefits. More flexibility later. More room for things to go wrong. More options when you get there.

Those decisions are what make a future possible in the first place. Without them, there isn’t much to trade off against.

At the same time, every decision that pushes further in that direction is pulling from somewhere else. More saved is less used. More time spent building something for the future is less time available now.

The tradeoff is always there, even when it doesn’t feel immediate. It’s easy to lose track of it when everything looks like it’s moving in the right direction.

I don’t think the issue is optimizing. It’s easy to see why it becomes the default. The results are visible. The path feels clear. There’s a sense that you’re doing things the right way.

The numbers give a feeling of control at exactly the moments when life makes it clear how little control there actually is.

What’s less visible is whether the direction still fits, and what might be getting less attention in the process.

That’s something I’ve been sitting with in some of the more everyday decisions too.

The Decisions in the Middle

At least once a year, my wife and I go back and forth on our home. Our home is one of those decisions that sits right in the middle of how we live now and what we’re building toward.

There are moments I lean toward doing a little more. Spending more to improve the space, or even thinking about whether we should find something bigger.

It’s easy to frame that as a better outcome. More space. More flexibility. Something that might fit future versions of our life more easily.

At the same time, our current home gives us something we both value. Lower fixed costs. More flexibility in how we use our money. Less pressure to maintain something larger than what we actually need day to day.

Neither direction feels obviously right. Each just pulls in a different way.

What we’ve come back to isn’t trying to get that decision exactly right. It’s paying more attention to what actually matters within it.

When Efficiency Isn’t the Point

We spend a lot of time outside on our patio. It’s where we unwind, where we talk, where things slow down a bit at the end of the day. So we’ve put more into that space than I expected we would when we first bought the house.

Better furniture. More plants and landscaping. More thought into how it feels to be out there.

That decision doesn’t really show up as an improvement in the outcome. It doesn’t make anything more efficient. It doesn’t move us closer to a higher number.

But it changes how we spend our time. More connected to what we care about.

I haven’t moved away from trying to make good decisions for the future. A comfortable retirement is still something I’m actively working toward.

But I’m recognizing that not every decision needs to be pushed as far as it can go in that direction.

Some decisions feel better when they're a little more connected to the life that's happening right now. The trouble is knowing when you've drifted too far in one direction. The decisions themselves still look reasonable on their own. They just start to stack in the same direction.

This is where I’m finding it helps to step back and look a little closer at what those decisions are doing beyond the outcome they’re improving.

My decisions don’t have to be optimal, but they should feel more consistent and connected to what matters to me.

I’m willing to work a couple extra months for what will hopefully be decades of mornings with my wife, sitting out on the patio we’ve built and love.

That tradeoff won’t show up as optimal anywhere.

It’s just one that feels more aligned with how we want to spend our time.

— Brad

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This is meant to help you think through financial decisions and tradeoffs—not tell you exactly what to do. It’s general in nature and not personalized advice.

One of life’s simplest joys is putting your hand in a pants pocket and finding a $20 bill you didn’t know you had. It’s immediate and feels like a little victory. Like you just found something for nothing.

But it’s not actually free money. At some point, it was part of what you earned. It just got misplaced for a bit. You didn’t have a plan for it and now it will probably get spent without much thought.

Why does a dollar we find feel different from the dollars we earn? It’s the same money. The difference is that it isn’t being asked to do anything.

Most of our money doesn’t get that treatment. At least not once it starts to feel like it matters. A raise. A bonus. A few hundred dollars sitting in an account. An extra $1,000.

At some point the amount gets big enough that you stop and ask: what should I do with it?

There’s rarely just one answer. Every dollar ends up serving some purpose along the way. The real tension comes from having too many reasonable options:

• Save it

• Spend it

• Invest it

• Pay down debt

• Give it to a cause worth giving to

None of those are obviously wrong. That’s what makes it challenging, and why money sometimes ends up doing nothing at all. Spending a little more time lost in the pants pocket instead of getting to work.

The Familiar Advice

There’s no shortage of guidance on how to work through this. Most of it follows some version of a familiar sequence:

• Build an emergency fund

• Pay off high-interest debt

• Contribute to retirement

• Invest the rest

The advice itself isn’t really the issue. The sequence just assumes life follows an orderly progression. Complete one step and move to the next. In practice, priorities overlap and interrupt each other in ways the sequence doesn’t account for:

• Someone carrying credit card debt may also have no real emergency savings.

• Someone saving consistently may still feel unprepared for something unexpected.

• Someone may be doing everything right on paper and still not feel clear on what any of it is building toward.

In those situations, the issue usually isn’t knowledge. The sequence is familiar. The steps make sense. But when the steps don’t map cleanly onto the actual decision in front of you, the guidance starts to feel like it was written for a different situation. Not yours.

I ran into a version of this when my wife and I bought our home. The standard sequence would have pointed us toward building a safety net and paying down the mortgage. But what I was actually most concerned about was what would happen to the house if something happened to me.

So instead of following that order, we put money toward supplemental insurance. Enough that my wife would never have to worry about losing the home if I wasn’t around.

The sequence wasn’t wrong. It just didn’t account for what we were actually trying to solve for. That gap between what the order says to do and what the dollar actually needs to do can really matter.

A simpler way to look at it is that every dollar is being asked to do a job. Sometimes that job is stability or relief. Other times it’s building the future, preserving flexibility or improving life today:

• Building enough of a buffer that something small doesn’t turn into something bigger (stability)

• Paying down debt that’s been sitting there longer than it should (relief)

• Saving or investing to create more options later (future)

• Keeping access to your money so you’re not locked into one path (flexibility)

• Using money in a way that actually improves your day-to-day (life today)

Those aren’t categories you move through once. They’re competing uses for the same dollar. That competition between uses is the actual decision.

Money Has Its Limits

A dollar can’t do all those things at the same time. The moment you give it one job, you’re taking it away from another. Putting more toward debt means less for investing. Investing more means less flexibility today. Saving more often comes at the expense of using money now. None of those are inherently right or wrong, but each one carries a tradeoff whether it’s acknowledged or not.

If you go back to that $1,000, the “right” answer starts to look different depending on the situation. For someone with no real emergency savings, that dollar is probably doing its best work creating stability. For someone carrying credit card debt, that same dollar might be better used for relief. The math matters, but it's not the only thing at play. The reduction in stress and the certainty of the outcome tend to matter just as much.

Once a solid foundation is in place, the decision opens up. That dollar could go toward future growth, flexibility, or improving life today. At that point it’s less about following an order and more about deciding what matters most right now.

Two people in different situations might use that same dollar in completely different ways. Both decisions can make sense given what they’re trying to prioritize.

The same is true in reverse. A dollar can be doing the same thing for people in completely different circumstances. Someone who likes their job may choose to prioritize the present over building for later. Someone who knows their health is at higher risk than the next person may also want their dollars going more to now than later. Two different situations. Dollars doing the same job.

The supplemental insurance decision I mentioned earlier fits here too.

Once our net worth had grown enough that we could cover the remaining mortgage on our own, we canceled the policy and redirected that money elsewhere. Some people would look at that as money wasted. Years of premiums for a policy we never used. I’d still make the same call. The job that dollar needed to do was stability and peace of mind, and for a long time, that’s exactly what it did.

The sequence still isn’t wrong. It just doesn’t adjust well to the way decisions actually show up in real life. It tells you where money often goes first, but not what those dollars are doing or why that order matters in a specific situation.

The Next Dollar Is the FI Equation in Real Time

Financial independence (FI) gets framed in a similar way. Save enough, hit a number, and you’re done. But that outcome is built from decisions like this one, made repeatedly over time. How money gets used along the way shapes both how quickly you get there and what it looks like when you do.

When you decide to put your money toward one thing, you’re trading away another. Stability or growth. Now or later. Life you’re living or the one you’re building toward.

The question is which one needs the next dollar more right now, given where you actually are.

You don’t need a perfect order, and you don’t need to optimize every decision. But when a dollar gets used without that clarity, the trade-off is still happening. It just happens without you.

— Brad

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This is meant to help you think through financial decisions and tradeoffs—not tell you exactly what to do. It’s general in nature and not personalized advice.

There’s a version of Monday morning that doesn’t get talked about much.

No emails.
No meetings.
No one waiting on your approval.

For some, this is exactly what they’ve been working toward. Uninterrupted freedom. For others, it feels like a part of them would be missing, even if they haven’t experienced it yet.

A few years ago, my dad said something that stuck with me. He had been retired for a few years, and in the middle of a normal conversation, he mentioned that he missed feeling important on a regular basis. The way he used to feel when people would turn to him at work for advice. Where his input carried weight.

That role didn’t happen overnight. He spent decades building it, rising through banking to eventually become a CEO and leader in his community. And then, over a relatively short period of time, it was gone. Retiring was his decision. He’d spent plenty of time saving towards it and years looking forward to it. But leaving his job removed something that had been a large part of how he defined himself. His identity now had a bit of a hole to fill.

While my dad came to this realization after leaving his work-life behind, many still cling to their job identity like it’s their reason for showing up each day.

What Work Provides

No longer having a job doesn’t just change how time is spent. It can change how someone sees themselves.

A career fills more than a schedule. It creates structure, feedback, and a sense of direction. Over time, that builds into:

• a role people recognize

• a place where decisions matter

• a consistent signal that what you’re doing is important.

You likely won’t even notice it happening while you’re in it. Your identify and your job merging in the background, day after day.

When that structure disappears, there’s more freedom and flexibility, but there’s also less definition. Priorities aren’t assigned anymore. Progress isn’t measured the same way. The shift happens whether you’re ready for it or not.

Why Some People Don’t Step Away

For some people, there’s a real fear in their job title changing from something like business owner or C-suite exec to “retiree”. They aren’t quite sure who they are without the big title.

This is part of the reason some people continue working long after they no longer need the income. It’s not always about the money. Sometimes it’s about holding onto the role that gave shape to their time. To their identity.

Who are you when you’re no longer the person at work everyone depends on?
And how much of that answer have you already figured out?

The longer you stay, the easier it is to avoid the question.
The moment you leave, you have to answer it.

Continuing to work keeps that role intact. It preserves the structure, the recognition, and the sense of being needed. But it also delays having to figure out what replaces it.

What That Looks Like in Practice

This isn’t easy. I’ve been struggling with it myself for a long time.

I’ve tried to be more intentional about relationships, but that’s harder than it sounds. It requires effort on both sides, so it’s not always in my control.

I’ve looked for things that feel meaningful beyond just passing time. Ski trips and shared travel experiences give me a reason to get out, explore somewhere new, and reconnect with people I care about. But they’re expensive. So now that becomes another decision—something I have to plan and adjust for. And even then, it’s harder to do consistently while working full-time.

Lately, I’m trying to figure out what I care about enough to keep coming back to. For a while, I thought that might be more charity work and community involvement. And maybe it still will be. But somewhere along the way, I realized I’m even more drawn to writing and talking about personal finance—trying to help people think through the same kinds of decisions I’ve been working through myself.

I don’t have a clear answer yet, but I’m starting to see pieces of it. Putting together a few things that seem worth building around.

What Often Gets Ignored

We spend time thinking about potential investment returns, adjusting budgets and withdrawal rates, or modeling potential scenarios and assumptions.

We don’t spend nearly enough time considering our after-work identity. Which means the plan can work financially, and still leave a gap you weren’t expecting.

There’s a need to account for what replaces the structure that’s been there for decades, or how long it takes to build something new.

For most people, that gap stays hidden until it’s no longer avoidable.

Financial independence (FI) tends to be framed as the point where work becomes optional. That’s partially true, but there’s more happening here. The FI equation isn’t just about whether you can step away from work. It’s about what you’re stepping into. There’s now a need to fill the space that appears when a job is no longer required.

Some people already have a sense of what fills it. Others don’t. Work has consistently filled the time, so they haven’t seen much reason to.

The challenge is when this question only shows up at the end. When the structure is already gone and there’s no longer a gradual transition, just a clean break from something that’s been there for years.

Building it Before You Need It

Most of those doing well in their careers have thought about what they need to retire comfortably. Fewer have spent the same amount of time thinking about what actually comes next or what they could be building towards.

Yes, there’s a list of projects they want to get done, maybe some books to read and a few hobbies they’ve been meaning to explore. But there’s a difference between having things to do and having something that defines how you spend your time.

It would be nice to have an answer when someone at a party or get-together says, “What do you do?” that isn’t just “I’m retired.”

What will define who they are the way their work has for the last 20 years?

There’s a version of FI where nothing really changes except the absence of work. And there’s another where something has already started to take shape before that transition happens. The difference isn’t the number. It’s what’s been built alongside it.

What To Actually Solve For

This isn’t about deciding if you should keep your job or move on to the next chapter. It’s about understanding that for a long time, you’ve had a defined role and structure. That will likely shift and require a lot more self-direction.

It helps to think about identity in layers. There’s who you are at work: the role, the title, the expertise. But there’s also who you are to your family and friends, and who you are in your community. For most people those layers exist but work has been so dominant that the others haven’t had to carry much weight.

When work steps back, those other layers have to fill more of the space. The question worth asking before that happens is whether they’re already strong enough to do that, or whether they need more building.

Are you known for something outside of what you do professionally? Is there a role you play in your family or your community that would still feel meaningful without the job title behind it? If not, that’s worth paying attention to now rather than later.

Being intentional earlier tends to change how that transition feels. From there, building purpose or expanding identity gets a little easier.

Some people start to practice this before it becomes a hard stop. It gives them a chance to find meaning in things that don’t come with a title or performance review, and to see what doesn’t.

If the role you’re known for disappeared tomorrow, what would still feel like a meaningful way to spend your time?

And is that something you’re already doing, or something you haven’t figured out yet?

For a long time, the role answers the question for you.
After that, it’s yours to answer.

Stepping away gives you control of your time, but also removes the structure that made that time feel meaningful.

The hardest part might not be stepping away from work. It might be figuring out what replaces the role and identity you’ve spent years building.

— Brad

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This is meant to help you think through financial decisions and tradeoffs—not tell you exactly what to do. It’s general in nature and not personalized advice.

I’ll say, “I think I figured out a way for us to both retire a year earlier.”

And she’ll say, “Did you make coffee?”

I know this isn’t how most people spend a Sunday morning. But for some of us who find ourselves drawn to thinking about financial independence, it kind of is.

I’ve been this way for decades. If we’re going on a trip, I build an itinerary in Excel with reservations, confirmation numbers, booked time slots, and of course make sure to schedule enough time for unscheduled time.

When we take on a new debt like a car loan, I add it to an amortization spreadsheet so I can see exactly when each debt ends and roll that payment into the next one.

I even built a spreadsheet to figure out when we’d need to start saving for two kids to go to college. The thing is, I didn’t have kids at the time. I still don’t. I had a separate spreadsheet for that too. A timeline for when my wife and I would need to decide to even have kids, overlapping with the age range that made most sense to start trying if we did.

I hate to say it, but there wasn’t some horrible accident that made me this way. And as far as my parents will admit, they never dropped me on my head. This is just how I exist. I reach for a spreadsheet when life gets complex or uncertain, like a coping mechanism.

I say this not to highlight how different we may be, but to point out what we likely have in common.

Anyone who has thought about their financial future has probably felt some version of that uncertainty, whether it’s looking for reassurance, trying to gain control, or just a vague sense that there’s something you should be doing but haven’t gotten to yet. That feeling is pretty universal.

What isn’t universal is how people respond to it. For me it’s a spreadsheet. For others it might look completely different, or it might just mean putting it off a little longer.

I didn’t start off any different from where some of you may be. When I first started my career, and even a few years in, I didn’t have a well thought-out plan. I was periodically checking accounts, had a general sense of my savings and debts, and was trying to figure out how to balance what was available with the decisions we were making.

I knew what I had, but hadn’t started connecting any of it to a longer view of the future.

That started to change when life began adding up faster than I could casually track it. We got married. We were thinking about buying a place and moving out of our apartment.

There were conversations about whether we’d start a family. A few years later I got a promotion, and my wife was considering a job change. There were a lot of moving pieces, and passively glancing at account balances wasn’t cutting it anymore.

With so much uncertainty, I opened an Excel file and went to work. I entered our salaries and made assumptions about what the next several years might look like, projecting where we’d likely be when some of these decisions came due.

Then I inventoried our accounts—retirement accounts, savings, checking, a brokerage account—and tallied what we were contributing to each.

A few more assumptions about expected returns, how many years we’d still work, and how long we’d need the money to last, and I was most of the way to a simple plan I could actually follow.

That simple plan has grown considerably since then. What started as a way to get my arms around a lot of uncertainty has turned into a living document I update throughout the year, revisiting it when something changes or a decision is approaching.

The habit of returning to it is probably what’s made the difference. There’s a big gap between something you create once and set aside and something you keep coming back to.

Variables, tradeoffs, inputs that change the outcome. They were all there from the beginning. I was building my own FI equation before I even had a name for it.

Not everyone needs to build what I built. My spreadsheet has grown into something that works for me but wouldn't be easy to hand off as is.

But having some intentional framework you actually return to, one that meets you where you are and grows with you, is something I think most people would benefit from. Mine started simple. Yours can too.

I’m planning a few more posts on this topic and your input could help shape what I write about next. Whether you have a plan underway or are still looking for a starting point, I’d love to hear what part of financial planning still feels most unclear or out of reach. Feel free to leave a comment, or if you’d rather not post publicly, my email is always open at brad@thefiequation.com.

— Brad

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This is meant to help you think through financial decisions and tradeoffs—not tell you exactly what to do. It’s general in nature and not personalized advice.

You know that feeling after the holidays or maybe a weekend trip when you may have overindulged and are now scared to step on the scale and see the damage? Instead, you might avoid the scale completely. If you don’t look, it can’t be true right?

Here’s the thing though. That scale is going to know that I went back for a second helping of dessert. And if I’m honest with myself, I already do, too.

Many of us avoid looking at our current financial situation for this exact reason. The false belief that I can’t be behind if I don’t look at where I am.

I don’t think it would be shocking to know that many of us push things off, especially when we feel overwhelmed, unsure, or even fearful. Someone who knows they should be looking more into their finances, but still pushes it off, might be feeling all three.

And where does one even start?

Instead, many of us focus our energy elsewhere, on the things we can control and are more familiar with, like working hard and building a career. This likely even allows us to put something aside for a future that’s still being figured out.

That’s a decent starting point, though there’s still plenty of gaps that will continue to exist and possibly expand without a bit more intention.

If that sounds like you, it might be time to honestly look at where you are so you can stop navigating blind.

What ‘Starting’ Actually Means

When I took my own first look, I didn’t set out to build anything. I just wanted a few basic things in front of me so I could see where I stood.

I wanted to know where my money was. Spread across which accounts. What I owed and to whom. And then the one that mattered most: whether what was coming in each month was actually more than what was going out.

I wasn’t trying to make sweeping changes. I just needed to see it, so I could tell whether what I’d been doing was working or not.

Starting simple doesn’t mean it has to stay simple. But if complexity and uncertainty are what has been holding you back, a simple approach might be the right place to start.

1. Where is my money?

2. What do I owe?

3. Does my income exceed my expenses?

That’s it. That’s where I started.

This can be as simple as logging into the accounts you already have, including any you might have lost track of, like an old retirement plan from a former job. Check the balances to see what’s there and what you owe, then look at a month or two of what came in and went out.

There are tools that make it easier to track over time (I use Empower), but you don’t need one to take the first look.

Looking Is the Start; the Choices Come Next

The first two questions show you what you have. The third tells you whether you have room to do anything with it.

If more is coming in than going out, you have something to work with, and the choice becomes where to direct it. If it’s the other way around, that’s the first thing worth understanding, because nothing else can really move until that gap closes.

My own first look provided me with the realization that while I was exceeding my expenses each month, the gap was a bit smaller than I thought it would be.

I couldn’t increase what I was saving each month without making some other changes first. But I also realized that the monthly savings transfer I’d set up earlier that year was doable.

A separate look was still needed to determine if the monthly savings I’d established for myself was sufficient for the long-term, but that’s for another day.

Just seeing it laid out won’t fix anything on its own. But like stepping on the scale, it reveals the reality of where you stand. A first real benchmark. There’s a bit of relief in that, even if the gap is small or pointed the wrong way.

Knowing the true situation, good or bad, is its own kind of control. And the sooner you see it, the more time you have to correct course, or to accept where your current priorities are taking you.

That’s where every plan begins.

Yes, I’ve gone on to expand my plan. There are other posts where I go deeper into what else I’m currently capturing, the things I track now, and the areas I’ve added complexity. All of which help balance the decisions I make with where I am and where I want to be.

But just those first few inputs gave me the foundation I needed to see my financial picture more clearly.

That's the part worth remembering if you've been putting this off. The first look is smaller than the worry that surrounds it. Three questions and an honest answer. Whatever you've been afraid of finding, seeing it clearly is what finally lets you do something about it.

— Brad

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This is meant to help you think through financial decisions and tradeoffs—not tell you exactly what to do. It’s general in nature and not personalized advice (see full disclaimer).

Before my wife and I were married we lived together, and like most people she had credit cards with due dates scattered across the month. Seven cards, seven different due dates. Some at the beginning of the month. Some in the middle. Some at the end.

She's always been smart with her money. Two of those cards were her everyday cards, the ones she used for most purchases. The other five came out occasionally for their rewards or loyalty programs. It wasn't carelessness that created the problem. It was just the system that developed naturally from managing multiple cards.

It’s the default and nobody tells you to align them. You may not even have known that was an option. But leaving them as the default creates a problem.

Some months she’d overdraft. Other months she’d carry a balance rather than risk paying before her paycheck cleared. That meant interest charges on balances that should have been paid off entirely. The money was there. The timing wasn’t.

It was a simple fix. She went online for each card and moved the due dates. Now everything falls on two days that work with when she gets paid. The overdrafts stopped. The carried balances stopped. The interest charges stopped.

Nothing about what she earned or spent changed. Just the timing.

I took a slightly different approach. All of my credit card due dates fall on the same day. My automated savings transfers go out the same day too. When I had a car payment, that came out the same day as well.

Everything in one moment.

That requires keeping a little extra cushion in checking at all times so I can cover everything coming out at once without cutting it close. I keep a small buffer in a high yield savings account that I can transfer back quickly if I need it. For most people, spreading payments across two or three dates reduces that cushion requirement slightly. The tradeoff is more dates to track and more moments during the month where you need to know if you’re covered.

My wife uses two dates for exactly that reason. Her travel gets reimbursed by work, but reimbursements can be delayed. That creates swings in her credit card balances that don’t always align with when she gets paid. Two due dates gives her more flexibility to manage that without carrying balances forward.

There’s no single right answer. The right setup is the one that matches how your money actually moves.

Here’s what alignment actually gives you.

When everything comes out on the same day each month, your checking account balance at that moment tells you something. If it’s higher than last month, you netted positive. If it’s lower, you spent more than you brought in. If it’s roughly the same, you’re holding steady.

That pattern—higher, lower, flat—is easier to see than when payments are scattered across the month. A balance on the 14th means something different than a balance on the 3rd or the 27th. When you’re always checking at the same point in the cycle, the number actually means something consistent.

You can’t make good adjustments to something you can’t see clearly. Alignment doesn’t change what you earn or spend, but it does change how easy the pattern is to observe.

Once you see the pattern, you can do something with it.

This is a small adjustment. It costs nothing and takes a couple minutes of logging into your accounts to change a due date.

It’s the kind of input that changes what you’re able to see. And what you’re able to see shapes the decisions you make.

What does your checking account balance tell you right now? If the answer is “it depends on the day,” that might be worth fixing.

— Brad

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This is meant to help you think through financial decisions and tradeoffs—not tell you exactly what to do. It’s general in nature and not personalized advice (see full disclaimer).

If you needed to list out all the assumptions going into your financial plan, could you? Not just the ones you’ve set intentionally, but the ones you’ve accepted without questioning, and the ones you know you need but can’t fully answer yet.

Some came from things you heard or read. Others were educated guesses. Some may have just been the default value in a retirement calculator.

You make decisions about how much to save, how much to spend, and when you’d want to step away. While those decisions matter, what tends to get less attention are the assumptions they’re built on.

Each of those decisions has an assumption behind it, whether you realized it at the time or not.

• Decision: how much to invest. Assumption: what those investments will return.

• Decision: what kind of lifestyle you want. Assumption: what it will cost to maintain it.

• Decision: when you’d like to be done working. Assumption: what the years around that will look like.

Those assumptions might not feel like actual decisions you’re making. But they impact the outcome just as much as the decisions do. More important, changing just one assumption can reshape the outcome even if everything else stays the same.

Why Two Plans Can Look So Different

Two people can be saving the same amount and aiming for the same goal, but come up with very different timelines. One assumes higher returns and a lower spending need later. The other assumes more modest returns and builds in more room in their budget. Nothing about their effort changed, just the assumptions. The outcome looks completely different.

That’s part of what makes this tricky.

Assumptions don't come from one place and they don't all behave the same way. Some you've thought through intentionally. Most you're probably carrying around without ever really questioning. They're a mix, which means the outcome they produce is a mix too.

Some Assumptions Are Taught, Others Are Learned

Some of my assumptions came from my dad. He spent over 40 years in banking, has been a DIY investor and retirement planner most of his adult life, and shared a retirement projection spreadsheet with me years ago that shaped how I think about my own numbers. It helped me see things a generic calculator couldn’t capture — like what the gap between early retirement and Social Security looks like, or how to account for compensation that doesn’t change in a straight line.

His assumptions lean slightly conservative and I’ve borrowed some of that instinct. But I’ve also been willing to revisit mine as my own understanding has grown. The foundation was his. What I’ve built on it is mine.

Not all of it came from good decisions though.

I started investing right after the financial crisis. Not the most comfortable time to begin, but in some ways it turned out to be instructive. And in hindsight, the timing was pretty ideal.

My early investments did reasonably well. But I kept moving. When something gained, I’d sell and shift to something else. I didn’t want to give back what I’d made. I told myself I was being smart about it and locking in those gains.

Looking back, I wasn’t. I was reacting. For a lot of investors, the less you do the better the outcome tends to be. I was learning that the hard way.

That experience taught me something about my own assumptions that a calculator couldn’t. I had been assuming that staying active with my money was the same as staying smart about it. It wasn’t.

Placeholders, Not Permanents

We tend to focus on the FI number and treat it like the answer. In reality it’s just one version of the outcome based on the assumptions used. That’s easy to miss, because once the calculation is done it feels finished. The assumptions that created it don’t get the same attention. They stay in place, and we adjust our lives around that outcome.

It doesn't have to stay that way. I’ve gone back and adjusted my own assumptions before. Revised my withdrawal rate, expected returns, and what I think I’ll spend. Each change moved my timeline even though I hadn’t changed any of my actual behaviors. Just the assumptions.

Some of those adjustments have been straightforward. I’ve built in reduced spending at different points in retirement to account for the go-go, slow-go, and no-go years. Higher spending early when we’re active and healthy, pulling back later as that changes.

The assumptions are in my plan. But I’ll be honest: I haven’t fully connected those later-year spending reductions to what I’m currently saving toward. The assumption exists but it isn’t doing its full job yet. That’s a gap I still need to close.

Other assumptions I’m not ready to finalize yet. And won’t be for a while. When to claim Social Security is one. The right answer depends on how long I work, what my final earnings look like, whether benefits get reduced before I’m eligible, and how long my wife and I are likely to live. I can make an educated guess but I can’t set it with any real confidence yet.

Withdrawal strategy and Roth Conversion timing are similar. Both depend on tax rates, account balances, and retirement income that are still taking shape. These aren’t assumptions I’ve overlooked. They’re assumptions I can’t finalize yet because the information that would determine them is still being written.

That’s a different kind of placeholder than the ones I’ve already set. Not an assumption I made and forgot to revisit. An assumption I know I need but can’t complete yet.

Uncertainty is part of this, which means assumptions come with it. They’re guesses about things that haven’t happened yet. But they don’t have to stay fixed.

Think of them as placeholders that keep the calculation moving. Change them, and the result changes with them. It’s worth slowing down how those assumptions get set, and revisiting them as things change.

There are a few things worth doing when you look at your own assumptions:

• Identify and think through what they actually are

• Consider the assumptions you aren’t making

• Understand how each one affects the others, including the ones you haven’t fully set yet

Your assumptions aren’t perfect. But they’re not set in stone either. They’re shaping the outcome whether you’re paying attention or not.

— Brad

New here? Start here.

Or read more at The FI Equation.

If this way of thinking about financial independence resonates, subscribe for free to get future posts delivered to your inbox. (If you don’t see a welcome email after subscribing, check your spam folder.)

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This is meant to help you think through financial decisions and tradeoffs—not tell you exactly what to do. It’s general in nature and not personalized advice (see full disclaimer).

There’s a game I play when the lottery gets big enough that it makes national news.

I ask my friends and family two questions:

1. Would you keep working if you won?

2. What would you do instead?

The first answer is usually quick.

Occasionally someone says yes, but when they do, it’s usually because their work already gives them something beyond a paycheck. It’s something they chose for reasons other than money.

Most people say no. For them, a job is often just that. Something they do because they need the income, even if it comes with decent pay or flexibility along the way.

But they still see it as just a job. So it's not surprising how quickly most people would walk away from it if that need disappeared.

What Comes Next

The second question is where things can get a little more challenging.

Some people have an answer ready and say it with excitement. They want to start a nonprofit. Open a restaurant. Make music. Do something they’ve clearly thought about before.

But a lot of people don’t have an answer at all.

“I have no idea.”

That was always my answer.

The question wasn’t really about my job. It was about what I’d build my time around if I no longer had to build it around work at all. That’s a different question. And one most people haven’t fully answered.

I have a good job and it treats me well. But the odds of me still reporting to work every day if money no longer mattered were pretty slim. I just didn’t know what I would do instead.

For a while, I assumed I was one of the few who hadn’t figured it out.

But the more I’ve talked with friends and others in similar situations, the more I’ve realized that’s not true.

There’s a group of people who feel the same way. Maybe even a silent majority who just don’t talk about it.

We look around and assume everyone else must have it figured out. That they’re satisfied. That they know what they would do. We stay quiet.

Why Just Winning Isn’t Enough

Winning the lottery doesn’t solve that problem. It removes the need to make money, but it doesn’t replace what money was supporting.

It doesn’t tell you what to do with your time, or what you’ll miss when the structure of work is gone. It won’t give you a signal for what will feel meaningful when you no longer need a paycheck.

It just removes the constraint. Instantly.

When everything changes overnight, you don’t get the chance to figure things out along the way. You’re left with a question you haven’t had time to explore. Only now you’re expected to already have an answer.

What Financial Independence Actually Gives You

Financial independence (FI) works differently. It’s a slow building process.

You’re not just accumulating assets. You start to notice things. What you enjoy. What you don’t. What you wish you had more time for. What actually feels worth your attention.

That awareness develops slowly, and with it comes your ability to adjust:

• Try something and realize it’s not what you expected.

• Change direction without it needing to be permanent.

• Begin to move away from things that don’t matter and toward things that might.

By the time you have the option to step away, you’re not starting from zero. You’ve already been moving in a direction.

You Don’t Figure It Out All at Once

There’s an assumption built into the lottery question. That if money were no longer a factor, you should already know what you would do instead.

It’s just the reality that most of us don’t have that answer.

You don’t discover what matters most in a single decision. This happens gradually, as you pay attention to how you’re actually spending your time, including what you’d choose to avoid if you had the option.

For me, that's become clearer through the decisions I've made and adjusted along the way. Spending time with my wife. Focusing on my health and connections with my family and friends. Writing about financial independence and what drives our decisions, which grew out of wanting to help people and my own personal interest in it.

Just as important has been recognizing what I want less of. Things like spending weekends cleaning the house, or working longer than I actually need to. Even minor ones, like a long drive home from the airport after an already long travel day, have shaped how I think about where we might live someday.

None of this showed up all at once. It came from trying things and noticing what I enjoyed and what I didn’t.

And it’s still evolving. I don’t need to be certain about any of it. I just need to see how these preferences start to influence my decisions.

That's where the FI equation begins to take shape. In how I prioritize things like paying for a cleaning service, choosing where I live, or thinking about whether I'd be open to working part-time in the future as a way to test my readiness for retirement. Decisions that can be adjusted as I learn more.

Nothing is set in stone. The equation changes as my decisions do.

Building toward financial independence gives you the space for that.

Revisit The Questions

The decisions you’re already making, including the ones you keep putting off, are telling you something.

Go back to those two questions. Would you keep working if money wasn’t a factor? And what would you do instead?

Pay attention to what comes up when you sit with those a bit longer than you might have before. What you keep coming back to, what you’ve been putting off, what you’d do more of if the excuse of not having time went away. And if there’s just silence, take note of that too.

That’s not nothing. That’s where the direction starts to take shape.

Winning the lottery removes the need to work. Working toward FI gives you time to figure out what fills the space it leaves. Otherwise retirement just becomes the absence of work, which sounds about as enjoyable as a job that just pays the bills.

— Brad

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This is meant to help you think through financial decisions and tradeoffs—not tell you exactly what to do. It’s general in nature and not personalized advice (see full disclaimer).

The last time I received a raise, I knew what to do. I had a plan with where the money would go and what it would be used for.

Part of it would go to taxes, and at least a quarter to half would go towards long-term savings. The rest was free to spend how I pleased.

That’s how I approached most raises and the occasional bonus. Some for Uncle Sam, some for future me, and some for now.

It’s hard to argue against that being a sound approach. It takes the guesswork out and keeps me in line. But I realized I was doing it on autopilot. I hadn’t reconsidered why that split made sense for me anymore. More importantly, I hadn’t considered what I was trading away by sticking to it.

The decision wasn’t just about how to split the money. It was about whether I wanted to prioritize life now or later.

Once you start looking for the tradeoffs, you’ll start seeing them everywhere:

• Where to live. Higher cost for lifestyle, or lower cost for flexibility.

• Change jobs. More money or more flexibility.

• Retire earlier. Gain time now or more security later.

Most of these decisions don’t have a clear right or wrong answer. It helps to think about the version of you that results from each choice.

The Tradeoffs You See

My wife and I both chose not to study abroad in college. For me it wasn’t just the cost. I needed 150 credits to qualify for my CPA, and going abroad would have meant a fifth year of school, summer courses, or extra coursework during my first years of working. The financial and practical tradeoffs were real and I could see them clearly at the time.

What I didn’t see as clearly was everything on the other side. The friendships you build when you’re living somewhere new with a group of people doing the same thing. The experiences that only make sense when you’re that age, in that moment.

We didn’t take our first international trip until our honeymoon, years later. We travel often now and stay at nicer places than we ever could have in college. But it’s a different experience. Some of what we would have had then, we can’t quite replicate now.

My wife had her own version of that tradeoff. She also chose not to go abroad, and for a while she regretted it. What she got instead was an internship in Washington D.C. that ended up shaping her entire career. A tradeoff she didn’t fully choose so much as stumble into, and it worked out in ways neither of us would have predicted.

Same decision. Very different outcomes. Neither of us saw the full picture at the time.

The Tradeoffs You Miss

New parents often talk about the version of themselves that existed before they decided to start a family. The same is true if you changed careers or moved to a new city. The old life ends, a new version begins. That’s part of the tradeoff.

You’re not just choosing between options. You’re choosing between outcomes. Each decision creates a different version of your future. And a new set of tradeoffs.

That’s easy to see in hindsight. It’s harder to recognize in the moment.

Most decisions don’t feel like tradeoffs at the time. People often just decide what feels like the right thing to do. But underneath that decision is another layer. You’re choosing one path over another and giving something up either way.

Circling back to how to divvy up my raise. When I set how much to save, I knew there was an amount I needed to put away and a goal I was working toward. The tradeoffs were still there whether I acknowledged them or not.

• Save the same percentage. I’m trading the chance to spend more now—on travel, experiences, more stuff.

• Spend more instead of save. I’m trading future flexibility.

We’re in a much stronger position now than we were early on. Some of that came from being disciplined about those raises and bonuses. Some of it came from keeping certain costs simple.

Take our home for example. It was a real stretch for us at first, but we’ve stayed in it and the breathing room it’s given us financially has been significant. It’s not something I thought much about at the time. Now my wife and I talk about it often.

That flexibility has allowed us to pull back a little and make more room for life now. We travel more. We’ve gotten more comfortable spending on things that matter to us. The tradeoffs are still there. We’ve just gotten better at choosing which ones we’re willing to accept.

You can’t eliminate tradeoffs. You can choose which ones you’re willing to accept.

Depending on where your savings are, you might decide you’ve built in enough flexibility already. Or you might decide that money is still better off going toward your future.

The last financial decision you made, did you consider the tradeoffs? Did you actually choose which ones you were willing to accept? Or was it an afterthought?

The tradeoffs are there either way. You just get to decide whether you see them or don’t.

— Brad

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This is meant to help you think through financial decisions and tradeoffs—not tell you exactly what to do. It’s general in nature and not personalized advice (see full disclaimer).