A Perfect Plan Doesn’t Get You Moving
Why waiting for certainty keeps you from making better decisions
The Hesitation
Sometimes you just feel stuck. You’re not directionless, you just can’t seem to move.
You might find yourself watching accounts grow without acting, running scenarios without deciding, or feeling close but never quite ready.
Maybe you haven’t even gotten to the point where there’s anything to watch. Some are so certain they’ll make the wrong move, they just stay put.
This might show up as:
missing out on an employer match because you aren’t sure how much to contribute
letting money sit in your checking account, slowly losing value to inflation
delaying opening an investment account because you don’t know what to choose
So you sit and wait. The information to proceed must be somewhere. Once you find it, then you’ll move.
The real problem isn’t the lack of information. It’s the expectation that you need certainty before you act.
Think about the last decision you put off.
Was it really because you didn’t have enough information? Or because you didn’t want to be wrong?
What’s Behind the Behavior
A lot of what we learn early in life comes with some level of uncertainty.
Take driving.
You can follow the rules, pay attention, and do everything you’re supposed to do. Most of the time, that’s enough. But everyone understands that it doesn’t eliminate risk entirely. Accidents still happen, even when you’ve done everything right.
That possibility doesn’t stop you from getting in the car. It just becomes something you account for.
The same idea shows up in other parts of life.
You can follow a doctor’s advice, choose the recommended treatment, and still not get the outcome you hoped for. There’s uncertainty in how things play out, even when the decision itself is well-reasoned.
We don’t expect certainty in those situations. We accept that there’s some level of risk involved and move forward anyway.
But when it comes to decisions around our financial independence (FI), that expectation often changes.
Instead of approaching them the same way, it’s easy to start looking for a level of certainty that doesn’t exist. The expectation shifts from making a thoughtful decision to making one that can’t go wrong.
And when that becomes the standard, it becomes much harder to move at all.
I had this happen to me early in my career.
My first accounting job was fine, but I wasn’t learning as much as I should have been, or as quickly. I was falling behind some of my coworkers, and the situation probably wasn’t the right fit. But I kept delaying the decision to move on because I didn’t know if anywhere else would be any different, or maybe even worse.
Then people who joined the firm after me started getting promoted. Not me.
I thought about leaving. Then I’d reconsider. Another year passed. Still no promotion. Still I didn’t move.
It wasn’t until the financial crisis forced my hand that I finally took another job.
I was promoted within six months.
That one still stings a little. And it’s hard not to wonder if I’d started moving sooner, would that promotion have come sooner too? And the pay bump that came with it?
The Tradeoff
When you start looking for a decision that can’t go wrong, waiting begins to feel like the safer choice. There’s time to gather more information, think through more scenarios, and avoid committing too early.
Waiting feels like the responsible thing to do, especially when trying to avoid being wrong. It creates a sense of being thoughtful and careful with decisions.
For a while, that can feel like progress. Before long, it creates a different set of tradeoffs. Delaying action takes time to reveal itself and can easily be overlooked.
The cost of waiting for certainty begins to appear as:
years of missed growth
decisions you never tested
learned experiences you delayed
They tend to build quietly, in decisions that keep getting pushed out.
The contribution you haven’t increased.
The account you haven’t opened.
The change you’ve been meaning to make.
Eventually, that pattern starts to feel less like waiting and more like standing still.
Acting carries risk too. You might lose money, regret a decision, or have to adjust sooner than you expected. But taking action creates something waiting never will.
Information.
Even the bad outcomes can provide value. A person will often learn more from an investment that lost them money than one that performed well. Losses tend to reveal how you actually respond when things don’t go like you thought. Not how much risk you thought you could accept, but how much you actually can handle.
You begin to see how your assumptions hold up, how you respond to outcomes, and what you would do differently next time. Something you can use to improve future decisions and actions.
Over time, those adjustments start to move you closer to what you’re actually trying to solve for, even if the path isn’t as direct as you expected. You’re no longer trying to figure it out from the same place.
Be Careful
There's a natural tendency to judge decisions by their outcomes alone. A bad result means the decision was wrong. A good result means it was right.
That kind of outcome bias leads to the wrong conclusions.
The S&P 500 has dropped 20% roughly 25 times over the last 100 years. Someone who retired early and watched the market fall might conclude they made a mistake. In most years, the outcome would have looked completely different. Same decision. Different result.
So, was their decision wrong? Or were they just on the unlucky side of a range of possible outcomes?
The decision and the outcome aren’t the same thing. Confusing the two is where the thinking breaks down.
Recalculating
I have an embarrassing admission. I have a terrible sense of direction. It’s a running joke that if I have a 50/50 chance when turning left or right, I’ll pick the wrong one more often than I should.
I used to dread driving somewhere new because I didn’t want to get lost.
Then GPS became readily available, and everything changed. If I made a wrong turn, it recalculated and showed me a new way to keep going. I wasn’t lost. I was just recalculating.
I wasn’t any better at directions. I had just become more comfortable pivoting from one way to the next.
Too often we treat decisions like they are permanent and can't be corrected. A wrong turn isn't the end of the route. It's just a prompt to recalculate.
That’s what having a direction does. It doesn’t remove uncertainty, but it does make it manageable.
Staying Put vs. Getting Started
There’s a natural desire to balance the need for certainty with the desire to move forward.
At a certain point, waiting stops being about getting it right and starts to look more like avoiding decisions altogether.
A plan only becomes useful once it’s tested. The feedback you need doesn’t come from thinking through more scenarios. It comes from seeing how your decisions actually play out.
The goal isn’t to eliminate uncertainty. It’s to make decisions that can hold up across a range of possible outcomes.
Consider two people who want to start putting extra savings each month into a brokerage account.
Person A plans to wait until they better understand markets and the investments they want to make. Until then, their money stays in a checking account.
Person B doesn’t know much about markets or investing, but decides to invest part of their money now and sets up a recurring automatic transfer for future monthly amounts.
Even without calculating which outcome is better, there’s a difference in what each person learns—either by staying stopped or struggling forward.
Person A may build familiarity with concepts and follow what’s happening in the market, but their understanding remains somewhat abstract. Their money sits.
Person B starts to learn through experience. They see how they react when their investments fluctuate, begin to understand their tolerance for risk, and recognize what they would change going forward. Eventually, those adjustments begin to shape how they invest.
The difference isn’t that one of them had a better plan. It’s that Person B began to understand how their own FI equation actually works by using it.
By creating the brokerage account and setting up monthly transactions, they’ve built a system to learn, adjust, and improve.
What decision are you waiting to feel certain about?
What aren’t you learning by delaying?
The plan might not be what’s holding you back. It might be the expectation that you need to get it right before you start.
Don't wait for the perfect plan before you open the account, make the contribution, or take the job. You’ll learn more once you start moving and see what happens.
— 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.