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Build a simple foundation and optimize from there. That’s a line I find myself repeating a lot.
Building a financial system that’s well-controlled, reliable, capable of supporting you when you need it most, and ultimately serving your bigger picture dreams and goals is not a one-and-done task.
It’s a combination of personal habits, one-time tasks, routine practices, mindset shifts, and more. Because of these many moving parts, getting finances well in hand can feel overwhelming—or, if not overwhelming, a bit annoying and easy to procrastinate.
This is why many of us tend to start and stop, or work hard in a full-court press, only to feel things fizzle a few months later.
The trick to avoiding the start/stop cycle is to think of your financial life as a pyramid of layers.
You lay a simple “good enough” foundation—like sticking to a monthly spending cap, knowing your cash flow numbers, and automating some saving and investing.
Then, you fine-tune those foundational bricks, steadying that base, as you begin to build upward—diversifying earnings, optimizing interest rates and cashback earnings, going deeper on how you spend and save money, and so on.
But how do you do that continual fine-tuning without feeling like you’re starting over or dropping the ball repeatedly?
The answer is simple: make a habit of looking back.
Live in the gain while you work toward closing the gap.
Regularly evaluate.
Debrief your outcomes.
Then use the resulting perspective to make small, intentional changes: tweak a habit here, shift a bill there.
As you revisit this evaluation-retool process, your improvements will compound.
Even if your spending habits are lackluster and your savings plan is struggling, working on the single habit of routinely critiquing your financial house with a curious, problem-solving attitude will take you far.
Asking yourself simple questions like, How did this week go? What worked? What didn’t? helps you catch the things that need attention most.
Ultimately, evaluation is the system that ensures your broader financial system works well and continues in the right direction. It’s also how you check in on those process goals I talked about last week. (Debriefing regularly should actually be your first process goal!)
Inside Money $trategy $chool, we dedicate an entire module to evaluation. Students even receive weekly emails reminding them of weekly, monthly, and quarterly debrief items. Why? Because when this piece is in order, it’s so much easier to create steady forward progress.
No more start/stop cycle.
Just small, meaningful changes in the right direction.
How were your first few weeks of 2025?
What’s working, and what isn’t? Take a look back.
Use that reflection to guide your next step forward.
It is common sense to take a method and try it: If it fails, admit it frankly and try another. But above all, try something.
Franklin D. Roosevelt
Criticism may not be agreeable, but it is necessary. It fulfils the same function as pain in the human body. It calls attention to an unhealthy state of things.
Winston Churchill
A life spent in making mistakes is not only more honorable, but more useful than a life spent doing nothing.
George Bernard Shaw
I hope you enjoyed this edition of Under 2, an email series designed to share quick bites of wisdom to empower your financial journey (while keeping it short). Be sure to sign-up below to get these messages in your inbox.
All for now,
Lindsey