The problem with writing about FIRE since 2009 is that I’ve become completely sold on the lifestyle. I know how good freedom feels, so I have a natural tendency to want everyone I care about to achieve it too.
I’m also aware I can come across as annoying when I talk about FIRE, so I try to throttle my enthusiasm in most situations. After the first year of FIRE in 2012, I no longer told anybody I had retired. Instead, I’d tell people that asked that I was a writer or investor, to avoid strange looks or awkward conversations. I try to play dumb to save energy.
But as someone approaching 50, I’m acutely aware of how quickly time passes. There is no amount of money I would take to trade away the last 14 years of freedom. Not one dollar. OK, maybe two billion dollars.
As I think about the financial mistakes we make, whether buying too much car or house, picking a stock that craters, or pouring money into a business that fails, I keep coming back to the one mistake that dwarfs them all: staying at a suboptimal job far too long, and looking back at years of work that didn’t matter, done for people you didn’t respect.
You can recover from financial losses. But you can’t get back the years you spent being miserable when you didn’t have to be. That’s the regret that doesn’t fade, but grows over time.
Failing To Convince People In Their 40s And 50s To FIRE
I understand that leaving the workforce at 34 is unusual. I wouldn’t expect to convince more than 2% of the people I meet in real life to do the same thing in their mid-30s.
But now that I’m almost 50, I expected I’d be more persuasive. After all, it’s only 10 years away from the start of traditional retirement age. These are people who’ve had full careers. They have perspective. Many have kids. And after the S&P 500 delivered extraordinary excess gains since 2022, many of them have serious money.
So I’d expect more people to be taking their financial windfall and changing their lives – not staying tethered to the same commute, the same office with harsh fluorescent lights, the same micromanaging boss, the same soul-grinding routine.
Yet almost nobody does it. And recent conversations have made me feel like a complete failure at selling a lifestyle I genuinely believe in.
The Contradiction I Cannot Explain
Nobody on their deathbed has ever said they wished they’d worked longer. Yet here I am, failing to convince visibly disgruntled people I meet in real life to negotiate a severance and break free.
Yet, these are the same people who enthusiastically tell me how much money they’ve made from their investments in recent years. So either they aren’t as financially set as they claim, are irrational actors, or they simply can’t overcome the pull of making maximum income even when they clearly have enough.
What do you think?
I also think there’s something slightly absurd about being a grown adult who still has to take orders from another adult who isn’t your family. You’ve got wisdom, experience, and possibly children of your own, yet someone else controls your time. Ridiculous, especially if you are financially independent.
So what is going on? Is the FIRE movement actually dying, instead of being more important than ever due to AI? Maybe you can lend me your perspective.
Four Recent Examples That Stuck With Me
Exact details have been changed for privacy reasons.
1. The AMD Guy: 22X Returns, Still Clocking In
A 48-year-old man recently told me he’d made a 22X on his AMD position over eight years. That is extraordinary, and I congratulated him.
But I couldn’t stop thinking: why is he still driving 45 minutes each way to work, paying $50 a day to park, and working 50 hours a week fielding client calls and traveling? Meanwhile, his wife wants to quit work and spend more time with their young children, but he won’t let her. With a 22X, why is none of that changing?
If I invested $100,000 and walked away with $2.2 million on one position alone, I certainly wouldn’t keep grinding so hard. And I definitely would let my 40-something year old wife break free. There’s no need for both of us to be away from the kids.
2. The Bearish AI Investor: Complaining on Both Sides of the Trade
A pickleball acquaintance has been telling me the market is overvalued and AI is a bubble since 2025. I didn’t push back, even though I’d become an AI maximalist during this time, heavily investing in public and private venture capital.
Recently, gave me another example of why he hates his boss with a passion. “He’s a total, complete idiot!” he told me for the third time.
When I suggested for the possibility that we might not be in a AI bubble, and the bull run might still have legs and to reconsider, he said: “You don’t realize how much I have invested in AI companies!” So, simultaneously bearish on AI and heavily invested in AI, while complaining constantly about his job, his travel schedule, and his boss.
I genuinely don’t get it. He hates his boss and hates AI. But he says he has a ton invested in AI. So shouldn’t he break free?
3. The Entrepreneur: Perfect Investment Timing, Every Time
There’s an entrepreneur I bump into who always volunteers his big wins without being asked. Bitcoin. GameStop. OpenDoor. All highly speculative names that had massive runs. Yet somehow, he never mentions any of them before they run. Only after. Funny how that works.
The one that stuck with me: before Liberation Day in April 2025, when tariff announcements tanked the market roughly 20%, he told me he had gotten completely out a month beforehand. Perfect timing, as always. Did he get back in after the S&P 500 ripped back even higher? Details are sketchy.
Here’s what isn’t sketchy: if the wins have been as large and as frequent as advertised, why is a three-kid family still living in a condo with a belligerent alcoholic downstairs who scares his children? He’s mentioned this neighbor more than once. The annoyance in his voice is real.
If you’ve nailed Bitcoin, GameStop, and called Liberation Day, why not deploy some of that genius toward buying another condo? Or a cozy home in a neighborhood where your kids can actually play outside without worrying about what’s happening one floor below?
The best time to own the nicest home you can afford is when your kids are still living in it, not after they’ve grown up and moved out. That window closes faster than any trade.
4. The Unstable Dad: A 10X Return and Still Commuting to Palo Alto
A person I know was laid off, then unemployed for eight months. His wife earns about $230K, enough to cover their living expenses. He made about $2 million working at a highly successful startup, then he invested $150K in a public venture capital fund that has since gone up over 10X. They rent, keeping their cost of living relatively low. They also have a 6-month old.
Instead of taking his enormous gains to stay home and care for the baby, he chose to put her in daycare and drive 55 minutes each way to Palo Alto three times a week for a new job.
The career versus family tradeoff is genuinely hard. But taking two or three years off to take care of your daughter after essentially winning a $1.35 million lottery seems like a rational move.
Then there’s social media. Everyone, always, is successful. Losses are rarely mentioned. Huge gains are posted constantly.
I have no reason to believe they are not telling the truth, since why would people lie? However, why aren’t more people changing their lives and FIRing if they’ve made so much money?
Instead, what I do see is people spending enormous amounts of time posting about money, running auto-responders to sell products, building YouTube channels, hustling for followers. Which is fine. I respect the grind. But if you’ve genuinely made the money you’re claiming, what exactly are you still grinding so hard for? Just let your investment gains do the work for you.
I saw a tweet recently criticizing the FIRE movement.
Looking more closely at his account to understand why Joseph was so salty about FIRE, his portfolio appeared to be around $1 million.
With a family to support, I understand why $1M might not feel like enough to pull the trigger in his early 40s. At a 4% withdrawal rate, that’s only $40,000 a year, and most people would rather keep working than live in abject FIRE poverty.
I responded telling him to hang in there if he’s feeling behind. There’s room for all of us to build wealth. Seconds later, I got an auto-reply pitching one of his products.
And there it was.
Perception Is Reality Online
On social media, you can appear far wealthier and far smarter than you actually are. You can graduate from any university, never work a day in finance, build a YouTube channel anyway, and have thousands of people treating your opinions like gospel.
This is genuinely one of the great powers of the internet, and I mean that without sarcasm. Use it if you’ve got something real to offer.
But what became clear is that for some, the game was never about building wealth through investing. It was about building an audience to earn money online. The investing content is just the bait. I respect the hustle. But let’s be honest about what the hustle actually is, because the people watching might not be.
Are You Really FIREd?
If you claim to be FIRE but haven’t changed anything about a situation you call suboptimal, are you really FIRE? I’m not sure your financial independence number is real.
You can run the numbers endlessly and invent sub-genres, Coast FIRE, Barista FIRE, Fat FIRE. You can call yourself retired while your spouse keeps working for the income and benefits.
But you have to be honest with yourself if you want the label to mean something.
If the investment wins are as big as you claim, why are you still grinding at a job you dislike? At some point, the purpose of making money is to actually use it, not to keep score on a leaderboard nobody else can see.
Lots Of Twists And Turns On My FIRE Path
When I left my job in 2012, I was nervous. I asked my wife, who is three years younger than me, to keep working for a few more years for stability and healthcare. That was a real compromise, and I named it as one.
When I bought a house in 2023 that stretched us financially, I told you about that too. Living paycheck-to-paycheck was both stressful and humbling. I took on part-time consulting to rebuild liquidity and set a specific goal: enough passive income to cover all expenses by December 31, 2027. Because after that purchase, we were no longer technically FIRE. I had blown up our passive income by $150,000 a year overnight.
But I’ve spent the last 2.5 years finding my way back – through investments, part-time consulting, and writing my third book. I’m close. Maybe I’m already there, but I want a bigger buffer before I plant the flag again.
What I do know is that I’m done with corporate consulting. I’m back to writing in the mornings, taking the kids to school, playing pickleball before lunch, soaking in the hot tub thinking about my next investment, and napping before the afternoon pickup. Evenings belong to the family.
That’s not everyone’s ideal life. But after almost 50 years, it’s mine.
Walking away from the status and identity that comes with a prestigious role is hard. But if you’ve truly made an enormous return on your investments and you dislike your job and have children who actually want to spend time with you, you owe it to yourself to at least try.
If FIRE isn’t for you, that’s completely fine. Just make sure you run a regret minimization framework before life makes the decision for you.
Reader Questions About FIRE
Readers, why aren’t more people FIREing after massive investment gains? Or are people simply not as invested as they claim, online and in real life? Is it really that hard to quiet the hunger for money and security in exchange for a better life? How much do status and prestige keep people grinding away at jobs they dislike far longer than they should? Do you think the FIRE movement is dying?
Stop Leaving Money on the Table
Sign up for Empower, my favorite free financial tool. I ran my 401(k) through its investment analyzer and discovered I was paying thousands a year in unnecessary fees on active funds. I switched most of the portfolio to ETFs and have saved over $50,000 in fees since. If you’re grinding away at a job you dislike while quietly bleeding money in fees, that’s a painful combination.
This is also the last month I’ll be sending signed copies of my USA Today bestseller, Millionaire Milestones. If you’d like a copy, you can sign up for a free financial review with Empower after linking over $100,000 in investable assets. Full details and instructions are in this post.
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