Planning for the future when the playbook keeps changing
There are a few ways people try to outrun the unknown.
Some squirrel away savings in high-yield accounts, still clutching the belief that compound interest will somehow outpace inflation and the rising cost of oat milk. Others bet on real estate—bricks and land, appreciating slowly and stubbornly, if you pick the right zip code and survive the HOA. Then there are the crypto faithful, those who prefer volatility with their morning coffee and believe the blockchain holds answers the rest of us are too afraid to ask.
Entrepreneurship? That’s the path for the bold. Build something, scale it, sell it—or hang on and try not to let it consume your sanity and savings account at the same time.
And then, there’s the stock market. That ancient cocktail of strategy, speculation, panic, and patience. A place where numbers supposedly tell the truth—but only after they’ve had their fun.
Of course, not everyone’s in the game. Some live paycheck to paycheck, not by choice but by necessity. Some trust the system—pensions, 401(k)s, social security. And some don’t think about it at all. They spend what they make and assume the future will show up like it always has: eventually, and slightly behind schedule.
My Bet? The Stock Market.
This is where I landed. The stock market.
And let me be clear—this is my answer, not the answer. If you’ve built wealth flipping houses, minting NFTs, or launching a niche product on Amazon, I’m genuinely happy for you. This post may not speak directly to your journey—and that’s okay. But for those of us who didn’t start early, didn’t inherit a portfolio, and didn’t have a financial planner on speed dial, this might feel familiar.
I didn’t come in with a lump sum or some ironclad strategy. I started late—late 30s. That’s not a tragedy, but it’s not ideal either. So I approached it with urgency and intent.
I began with what I knew. Brands I trusted, industries I understood. No moonshots. No memes. Just companies I used every day—the ones I’d bet would still be around when my kids are my age.
And while picking companies is the flashy part people like to talk about, here’s what doesn’t get enough attention: how you set up your portfolio matters just as much as what’s in it.
Because of my income bracket, a traditional Roth IRA was off the table. So I took the backdoor route—converted a traditional IRA into a Roth. That way, every gain, every dividend, every bit of growth? Mine, tax-free. No asterisk. No fine print. Just a smarter structure for the long game.
From there, I expanded. ETFs. REITs. Index funds. Anything that would generate passive income while I was sleeping, working, or coaching one of my sons’ teams. I wasn’t just looking to make a quick buck—I wanted the snowball. I wanted the kind of compounding momentum that, years from now, could make “freedom” more than just a buzzword.
And so I became a student of it all. Blogs, books, podcasts—anything I could squeeze in during a commute or lunch break. Financial literacy wasn’t something I was handed. But I made it mine. Late, maybe. But not too late.
What the Market Taught Me: Play the Long Game
If there’s one lesson that rose above the noise, it’s this: the market rewards discipline, not drama.
I learned early on that trying to time the market was a fool’s errand. I didn’t have a crystal ball, and I wasn’t looking for one. What I needed was a strategy I could trust—not one that relied on adrenaline or FOMO, but one that respected time, consistency, and clarity.
So I stopped chasing. Instead, I started setting buy orders at prices I loved—not because someone on Twitter said to, but because I did the work. I researched. I ran the numbers. I identified the fair price and made peace with the wait.
And once I bought? I let it breathe. I chose companies, ETFs, and assets I could walk away from for five years—ten even. If you can’t stomach holding it through a dip, you probably shouldn’t be buying it in the first place.
The long game requires patience. And patience is only sustainable if you believe in the fundamentals. That belief came from the reading. From Guy Spier’s humility. From Warren Buffett’s restraint. From understanding that the most powerful investment tool isn’t money—it’s time.
But investing wasn’t the only muscle I had to build. Budgeting came first. That one came courtesy of Dave Ramsey—not Gordon, although I’m sure yelling at my spending habits in a British accent could’ve worked too. Ramsey taught me how to track, plan, and most importantly, pay myself first.
That mindset—that I deserved to build wealth before I gave it all away to bills and lifestyle inflation—was the breakthrough. Add in Robert Kiyosaki’s tactical advice on assets and liabilities, and suddenly I had a mental model that actually worked.
I kept going. Converted my traditional 401(k) into a self-directed account. Got bold enough to ask my accountant the right questions. Learned how to format my returns to align with my strategy. The passive bystander version of me was gone. I wasn’t just earning—I was building.
The growth was slow at first. That first year of “passive income” was humble—maybe enough to cover a decent pair of shoes. Now? Several years in, it can cover a month of my mortgage. And that’s without touching the principal.
Looking ahead, I’m beginning to believe in a version of my future where my lifestyle funds itself—where what I’ve built continues to compound, uninterrupted. Not because I got lucky, but because I stayed in the game long enough to stop playing it and start benefiting from it.
If You’re Just Starting Out
If any of this sounds out of reach—don’t let it.
You don’t need to be a financial analyst or a spreadsheet junkie. You don’t need ten grand in the bank. You just need the willingness to begin, and a reason to stay with it.
To see if I really understood what I’d been learning over the years, I tested it the best way I could—I taught it. To my sons.
Two of them picked up part-time jobs. Nothing glamorous, just solid work. And after those first paychecks hit? We went to school. Starbucks, actually. Saturday mornings, just us and a table, talking money over overpriced coffee.
I broke down the basics—compounding, investing, paying yourself first. I basically turned into a walking, caffeinated book review of my Audible library. But it landed.
They each opened their first institutional investment accounts. Within a month, their rainy-day funds were topped off, their emergency funds had momentum, and they were steadily building positions in an S&P 500 ETF. They reinvested dividends. Tracked growth. Watched their net worth climb.
Watching them set themselves up years ahead of where I started? That alone made every article, every financial podcast, every dollar I didn’t spend worth it.
So if you’re starting late—or just starting now—here’s how to begin:
5 Steps to Get Started:
- Set a Budget and Track It
Know what’s coming in, what’s going out, and where you can cut back. Build a budget that’s real—and stick to it. - Pay Yourself First
Before you spend a dime, invest a percentage. Start small if you need to, but make it automatic. - Set Up the Right Account
If you’re eligible, open a Roth IRA. If not, consider a backdoor Roth or a self-directed account that aligns with your income and goals. - Pick What You Understand
Start with ETFs (like the S&P 500), then layer in industries or companies you believe in. You don’t need to be fancy—just consistent. - Reinvest and Repeat
Turn on automatic dividend reinvestment. Let time and compounding do the heavy lifting while you focus on earning and learning.
Let’s Build Together
If you’ve read this far, you’re already ahead of where I was when I started. And if you want help getting started? I’ve got you.
Drop a comment. Subscribe. Or just leave a keyword or two below—“investing,” “portfolio,” “help”—whatever feels right. I’ll personally follow up with more insights, tips, and tools that helped me turn this from a theory into a strategy that actually works.
You’re not too late. You’re right on time. Let’s get to work.
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