Week 1 | The Missing Chapter | Joshua Grass, CFA, CFP®
Am I on track? Is my next dollar going to the right place? Is there a more intentional version of this that I’m not seeing?
If any of those questions have crossed your mind, you’re exactly who I’m writing this for.
Over the last few months, I’ve had the opportunity to meet with an assortment of professionals in varying fields. Doctors, a rocket scientist, a technology exec, mechanical engineers, attorneys, actuaries, data scientists, hell, even a helicopter pilot.
Every one of them is exceptional at what they do. And nearly every one of them, when we started talking about their financial life, said some version of the same thing: “I know I should have a better handle on this.”
That’s not an insult. It’s a pattern. The financial literacy gap doesn’t discriminate based on IQ, and if that sounds familiar, you’re exactly who I’m writing this for.
My name is Josh Grass. I’m a CFA charterholder and a CFP®. I’m 31. And I’m going to tell you something that might surprise you coming from someone with those credentials: I had to learn this stuff deliberately, too.
I didn’t start in finance. I started college studying biochemistry with plans for medical school. I understood what that path looked like, I was good at the coursework, and I followed it until I looked more carefully at what it actually required and made a different call. I pivoted to finance, an area I’d always been genuinely curious about, and eventually spent years in corporate strategy and national accounts at major financial institutions before joining Stapleton Asset Management. This year, I left a secure corporate role (recently promoted, making good money) three weeks after finding out my wife was pregnant, because I believed I could build something better. My son Beaux was born in December.
I’m telling you that not to establish a résumé, but because I want you to know who’s writing this. Someone who studied this professionally, holds two of the more rigorous designations in the industry, and still had to go looking for the practical knowledge of how to actually run his own financial life. How to think about our account structure. How to approach tax planning across multiple years. How to make sure we’re building in the right direction and not just accumulating money without intention.
Nobody pulled me aside and said, “Here’s how to think about your own money.” If it wasn’t handed to me, someone who chose this as a profession, it definitely wasn’t handed to you. And that’s okay. That’s actually the whole point of why I’m writing this.
Let me paint the picture, because I bet some version of it applies to you.
We wouldn’t expect a doctor to design a bridge. We wouldn’t ask an attorney to perform surgery. We wouldn’t hand a data scientist a set of blueprints and say “build me a house.” These are all brilliant people, but brilliance is domain-specific. So why do we expect any of them to just know how to build a financial plan?
Nobody ever taught them. There was no course in your engineering program called “What to Do When Your RSUs Vest.” Medical school didn’t offer a seminar on “Tax Planning for Your First Real Paycheck.” Your law firm’s onboarding didn’t include a session on “Why Your Group Disability Policy Has a Gap You Don’t Know About.”
You were expected to just figure it out. Or to Google it and hope you land on advice that isn’t trying to sell you something.
And so what tends to happen is a kind of financial autopilot. You follow the path of least resistance. Max the 401(k) because HR mentioned it during onboarding. Hold the company stock because it’s performed well. Swipe the HSA card for every copay and prescription because it’s a healthcare account and that’s what it’s for. None of it is necessarily wrong. But none of it is a plan, either. It’s a collection of defaults.
The real problem isn’t those defaults. It’s that without understanding what they’re actually for, you have no way to know when they stop making sense. Maybe you’re the physician who’s been maximizing her 401(k) every year, a good instinct, but who’s never been shown why the type of account she’s funding matters as much as the amount. Maybe you’re the engineer who has RSUs, a 401(k), and a brokerage account, each looking reasonable in isolation, but nobody’s ever pulled them into a single view and shown you the concentration underneath. Maybe you’re the attorney who has disability coverage through your firm and has never had reason to question it, until someone walks through what it actually pays out and how far short of your real income it falls.
You’re not behind for not knowing any of this. The gap exists because nobody connected the dots.
What makes it particularly hard to sit with is that we are all optimizers by nature. We don’t accept “good enough” in our own work. We find the more efficient path, ask the better question, look for what everyone else walked past. That instinct doesn’t turn off when it comes to our finances. It just has nowhere to go. The question that tends to surface isn’t “I know I’m doing something wrong.” It’s quieter than that, and harder to shake: Am I on track? Is my next dollar going to the right place? Is there a more intentional version of this that I’m not seeing? Not a specific mistake to fix, just the persistent sense that somewhere there’s a plan where every dollar has a purpose and a direction, and you’re not entirely sure you have one.
That’s what this blog is about.
I’m calling it The Missing Chapter because your education, your career preparation, your entire professional trajectory had this one chapter ripped out. The chapter on how to think about your own money with the same rigor you bring to everything else in your life. Not by anyone’s malice, just by the way knowledge gets organized and the quiet assumption that someone else was covering it.
They weren’t. That’s what we’re here to fix.
Over the next thirteen weeks, I’m going to write that chapter. One post per week, each one unpacking something you were expected to “just know” but probably don’t. Not because you can’t, but because no one ever sat down and walked through it with you.
Here’s a taste of what’s coming:
What actually changes when the promotion comes, and the financial playbook doesn’t. The tax interactions, the phaseouts, the decisions that quietly get more expensive to ignore.
Why you probably only have one type of money, and why the architecture of your accounts matters more than which stocks you pick.
Why I didn’t use my HSA to pay for the birth of our first child. A personal story that reveals the most underrated account in the tax code.
What “diversified” actually means when your career, your 401(k), and your brokerage account are all concentrated in the same companies.
What a complete financial plan actually looks like, and why managing the pieces in isolation is costing you more than you think.
Before we get started, a few things I want to be upfront about.
Here’s something that’s genuinely a pet peeve of mine: most financial advice is written as though there’s one right answer. Advisors market in absolutes. The smart move. The optimal strategy. What everyone in your situation should be doing. I think that framing is mostly wrong. The right financial decision isn’t the one that looks best on a spreadsheet in isolation. It’s the one that helps you accomplish what you’re actually trying to accomplish. Your goals are the starting point. Everything else is in service of those goals: which accounts you use, how you manage your taxes, where your next dollar goes. So while I’ll always explain the reasoning and show the math, I’m going to resist telling you what you should do. Because most of the time, the honest answer starts with a question: what are you actually trying to build? That’s the conversation this blog is trying to have.
I’m also setting a bar for myself: show the work. Not conclusions dressed up as expertise, but the actual reasoning, the math when it matters, the nuance when it’s real. If I make a claim, I’ll back it up. That’s a higher standard than most financial content holds itself to, and it’s the one I’m committing to here.
I’m not going to sell you anything in these posts. I’m a fee-only financial advisor. I don’t earn commissions, I don’t sell products. My incentive is the same as yours: build a plan that actually works. If you read all thirteen posts, learn something useful, and never reach out to me, that’s a perfectly good outcome. I’m writing this because the information should exist, clearly and honestly, in a way that respects your intelligence.
And I’m going to share my own experience along the way. I’m 31. I’m navigating the same life stage many of you are: the career acceleration, the growing family, the realization that the financial decisions you make in this decade compound for the rest of your life. I’m not writing from a mountaintop. I’m writing from the same trailhead, just a few steps further down the path.
One more thing: if any of this resonates, if there’s a part of you that felt quietly recognized in what I described above, I want to be clear that the gap in your financial knowledge isn’t something to be embarrassed about. It’s just something to close. Nobody handed you this playbook. The expectation that you’d just figure it out was the problem, not you.
The chapter was missing. Let’s write it together.
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Josh
Joshua Grass, CFA, CFP® is a financial advisor at Stapleton Asset Management in Minneapolis, MN. New posts publish weekly. This blog is educational content and does not constitute personalized investment or financial planning advice.
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