Doing Well Doesn’t Mean It’s Clear What to Do Next
You can be making progress and still feel unsure what it all adds up to
Watching your investments grow feels good. It feels like you’re making progress. But it doesn’t always make the decisions any clearer.
Even when things are going well—excelling at work, saving more than you used to, life feeling busy but balanced—you still feel unsure about the decisions you’re making.
I get it. The only person who wouldn’t be surprised by how often I’m looking at my finances is my wife.
You might be feeling this too. It’s hard to know if we’re making the right choices.
The questions probably sound familiar:
Should I spend more now, or save it?
Am I saving enough, or too much?
Should I change jobs even though things are working?
Am I any closer to what I want, or just further along the same path?
What path am I even on, and am I happy with where I’m heading?
The questions pop up often, but the answers? Rarely. Or at least not without some intention.
Right now you, and many others working towards their financial independence (FI), probably reduce everything down to reaching a savings goal for retirement—your FI number.
Decisions get reduced to: does this help me reach it or not?
No, you’re not doing something wrong. There’s value in that. But it’s too narrow to guide your decisions.
I didn’t come up with my own framework for thinking about this overnight. For a long time I just followed what I thought I was supposed to do — save at least 10%, invest for the future, stay in a job with good compensation and security. Things I’d read or heard along the way. A script that made sense on the surface.
The problem was it didn’t always reflect what was actually happening.
There were stretches where my wife and I watched our savings grow while our spending grew right alongside it. We weren’t actually getting ahead. We were just moving faster on the same treadmill. The progress was visible. The feeling of getting somewhere wasn’t.
Then there were the milestone benchmarks. You’ve probably seen them. The ones that tell you how many times your salary you should have saved by 30, by 35, by 40. For years those numbers made me feel behind. My wife and I both knew we’d earn significantly more later in our careers, but in our 20s and 30s we couldn’t seem to measure up. I didn’t stop using them so much as I quietly decided they must be flawed for our situation.
It wasn’t until our 40s that we started actually hitting those milestones. By then our combined income was much larger than it had ever been, which made the targets harder to hit in a different way.
Just saving more or picking up a few tactics doesn’t really solve it either. It helps to look at it a little differently. An expanded view that doesn’t just work around the number.
Shift the focus to your decisions and what they’re built on.
Future posts will go deeper into this, but the core idea is this: the FI number alone won’t give you what you need. There’s a bigger equation at play. One that’s shaped by your decisions and how they connect to each other.
When those connections aren’t clear, it’s easy to keep making progress without ever feeling more certain about where it’s leading.
I still feel that. I can see the savings growing, watch the timeline take shape, and still find myself wondering whether the choices between now and retirement are the right ones. Whether it will all add up the way I’m expecting.
The progress is there. The clarity isn’t always.
— 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).


