
A 37-year-old subscriber emailed me last week. She’s making $140,000, has no debt, and lives in a 900 square foot studio apartment because she’s saving 65% of her income.
Her goal?
Retire by 45. She'd found FIRE (financial independence retire early) two years ago and went all in.
Her question was practical: should she put more into her taxable brokerage or max out a second Roth to save on future taxes?
But the thing that got me wasn't the question. It was the last sentence of her email:
"I don't let myself spend on anything that won't get me to my goal faster."
Spoiler: I didn't respond with a tax strategy.
I asked her when she'd last taken a trip. When she'd last spent money on something because she wanted to. When she'd last felt like a person instead of a savings rate.
She wrote back two days later.
She hadn't taken a real trip in five years. She'd missed her best friend's bachelorette in Scottsdale because flights were too expensive. She was eating the same five meals on rotation.
She said she didn’t love it, but the urge to not have to work until she’s in her 60’s is so strong.
Now before you get defensive, I completely understand the appeal of FIRE.
Financial independence sounds like freedom. Retiring in your 40s, before your body starts sending you physical memos? Sounds great on paper.
But I don't follow it, and I don't teach it.
And every time I see someone go all-in on FIRE, I get a little twitch in my eye.
Here's why.
YOLO
You only live once.
I know how that sounds coming from a financially responsible millennial. Hear me out.
There's a version of your life where you spend your most mentally and physically capable years eating ramen, skipping girls trips and spending your Friday nights balancing your budget.
Then you retire at 45 with a full portfolio and immediately throw your back out. Or your parents get sick. Or your kids still need things. Or you find you can't do the things you were saving "freedom" to do.
This isn’t hypothetical. It's real life.
I’ll turn 39 this year.
My husband Andrew and I live on a piece of his family’s farm in rural Pennsylvania. We raise show pigs, I have horses, and two barns to keep up with. We also both work full-time off the farm.
Each November, when Andrew leaves for his annual bow hunt in Illinois, I get up at 4:30am instead of 5:15 and run the whole thing myself. I know what my body does and doesn't want to do now versus 10 years ago.
I'm not old (at least I don’t think of myself as old lol). But I'm different.
And the things I wanted to do at 29 are not the things I want at 39. Some of them I wouldn't want to do now even if I could.
Extreme frugality during your prime years is a bet you're making with your future self about what he/she will want. And they might not agree with you.
The Math Only Works If Nothing Goes Wrong
The backbone of FIRE is the 4% rule.
The idea: save 25X your annual expenses, withdraw 4% per year, and the math holds indefinitely.
There's just one problem…
The 4% rule was designed for a 30-year retirement.
Retire at 42 and you're funding a 40-year retirement. Maybe even 50.
That completely changes the math.
Retire at 42 with $1 million and your portfolio has to survive two financial crises, a pandemic, and a few things nobody's thought of yet before you'd even qualify for Medicare.
The same $1 million retiring at 62 only has to cover 30 years.
One bad bear market in your first decade of retirement (2001, 2008, 2022, take your pick) and fixed inflation-adjusted withdrawals start depleting your nest egg before the market recovers.
That is a real, documented risk.
It even has a name: sequence of returns risk. And early retirees are uniquely exposed to it.
A 50-year sequence-of-returns is a whole different animal from a 30-year one.
Then add in health insurance.
Off your employer's plan at 42. Not eligible for Medicare until 65. That's 23 years of premiums.
A healthy 42-year-old pays $400-600/month for a decent plan. By 55, that might increase to $800-$1,200/month. Run that out over 20 years and you're looking at ~$200,000 to $300,000 in insurance costs alone, before a single claim.
The math just got a whole lot messier.
The Scarcity Mindset Doesn't Turn Off Once You Hit Your Freedom Number
FIRE requires years of conditioning yourself to spend as little as possible.
Saying no. Tracking every dollar. Treating purchases as enemies.
Then suddenly one day, you hit your number. You retire. You're free!
And…you can't spend the money.
Whomp. Whomp.
Not because it isn't there.
Because your brain has been wired for deprivation for a decade, and that wiring doesn't magically reset the day your portfolio hits $1.2 million.
People I know who followed FIRE tell me spending feels like failure.
Call me crazy, but that’s not something I want my money to make me feel.
There are entire subreddits full of FIRE adherents who hit their number and then worked "one more year to be safe," then another, then found themselves at 55 still in the job they swore they'd leave at 40.
The freedom they chased became self-inflicted golden handcuffs.
Isn’t that what you’re trying to escape in the first place?
Work Gives You More Than a Paycheck
I’ll be the first to tell someone, the sooner you can get out of a job you hate, the better.
Yet, ask anyone who’s completely retired. The first 3 months feel like a long vacation.
Then it's month 4.
It’s a dangerous thing to follow FIRE solely for the purpose of ‘never having to work again’.
Work gives you structure. Identity. People. A reason to get dressed. A problem to solve. A place where you matter.
Strip all of that away at 43 with no clear plan for what comes next, and you get a lot of people who spiral. By their own accounts. Boredom becomes restlessness. Restlessness becomes anxiety. And the whole project they sacrificed years to achieve starts to feel hollow.
It definitely does not have to be a 9-5 working for someone else. In fact, I highly encourage it not to be. But it should be something.
Bottom line: a job that's destroying you? Leave it.
But "retirement at all costs" is not the same thing as "a life well-lived."
The FIRE Math Assumes You Earn Well Above Average
I don’t see a lot of FIRE promoters talking about this, but a 50-70% savings rate requires a very specific kind of income.
If you make $250,000, it's uncomfortable but doable. If you make $70,000, you're living on $21,000-35,000 a year.
In 2026 America, that is survival mode. Not investing mode.
The loudest FIRE voices are almost always high earners: software engineers, doctors, attorneys who did something demanding for a decade and then stopped.
And look, it’s a completely legitimate choice.
But it gets sold as a universal strategy to people for whom the math simply doesn't work, which means they compensate by reaching for risk. Speculative passive income. Real estate flips. Individual stock bets.
Ironic, for a movement built around security.
What I Do Instead
I invest consistently, and increase my contributions anytime I can.
I live below my means, but not to the bone.
I still take the trip.
I said yes to the concert this summer.
Last weekend mom and I replaced the porch cushions because they were frayed and dry rotting.
I’m building wealth quietly over time without sacrificing the years I'm living right now to fund some theoretical future self who may or may not still want the same things.
Because who knows, I may never even get there.
~
Financial independence is absolutely worth building toward.
The freedom to choose your work, to walk away from what doesn’t bring you joy, to not need any single paycheck to live. That all matters.
That's what I want for you. That's what I'm building toward myself.
But retiring at 42 on a shoestring budget while spending your 30s miserable is not freedom. You’re not building a better mouse trap, you’re simply still trapped.
Quiet wealth looks different.
It looks like growing your portfolio while also celebrating your best friend’s 40th birthday weekend in NYC. It looks like booking the flight when the fare is actually reasonable. While also, yes, replacing the porch cushions.
Compounding doesn't care you're not on a 65% savings rate. It cares that you started.
Your wealth hype girl,

-Charlie
📌 P.S. Want to figure out what financial independence actually looks like on your terms? Book a 1:1 strategy session with me here. I’m currently offering a discount just for email subscribers.

🔗 Links You’ll Love
🏦 The hidden cost of paying taxes quarterly — and the strategy that fixes it. As someone who is always looking for the next (legal) loophole to keep more of my hard-earned money in my own pocket, I love Max Donovan’s “What Tax” newsletter.
📊 Will vacation inflation affect your summer travel plans? — here’s everything you need to know. Plus 11 questions on summer travel and airline outlooks.
🎥 What $100/month will get you in 30 years — in this video, I break down the real numbers behind investing just $100/month, and show you how small, consistent growth can turn into serious wealth over time. If you’ve ever felt like you don’t have ‘enough’ money to start, this just might change your life.
💭 Weekly Wonderings…
🐷 On the farm: the nephew and nieces had their first pig show of the year yesterday. While the weather was horrible (🎶 where are you summer!? 🎶 - sung to the tune of the “Where Are You Christmas?” from the Grinch), the kids learned a lot and the pigs had their first trip off the farm. Here’s hoping the next one the temps get above 50 and it’s not raining!

📈 On social media: I took the plunge and started an Instagram! Why? Because I needed something more to do. HA! But in all seriousness, since hitting over 100K followers on TikTok (🤯), I thought it time to branch out onto other platforms. It’s a steep learning curve, but I’m having fun. Would love to have you follow along!
📬 From my inbox: a subscriber was confused on tax implications of moving investments around in her Roth IRA. The beauty of the Roth is that you’ve already paid taxes on the money that’s in there. You can buy and sell investments within your account as often as you want without triggering a tax event. Just make sure you’re not actually pulling money out of the account completely. Unless it’s your contributions, you’ll pay a 10% penalty on that money if you’re not age 59 ½ and the account hasn’t been open for at least 5 years.
💰 Quiet Wealth Move
You can’t change what you don’t acknowledge.
If your way of tracking your investments looks like my brother’s room growing up, it’s time to get your s$%^ together my friend!
My Stock Tracker & Portfolio Balancer does exactly that.
It's a simple Google Sheet, fully customizable, and it costs less than 2 cups of ☕️.
Once you’ve got everything in one place, ask yourself: is my most tax-inefficient investment sitting in my most tax-protected account?
If not — you've just found some hidden money!
That's it. 20 minutes. Could be worth $1,000s over the next decade.
When you’re ready, here’s how I can help:
If you want to sit down together and map out your specific asset location strategy — which investments go where based on your exact accounts, income, and tax situation — that's exactly what my 1:1 private strategy sessions are for.
No pressure, no pitch. Just your numbers and a clear plan.
Disclaimer: this content is for educational and informational purposes only, and is not legal, financial or investment advice. Always do your own research before investing, and consult a licensed professional. Charlie and OJD LLC are not responsible for any losses or decisions made based on this content.
