Something funny happened after I spent $3,000 fixing up my 2015 Range Rover Sport. A 2026 Range Rover Sport in the same black on black with 905 miles became available. It was the perfect setup, because buying a brand new car is a serious waste of money. When you’re the family’s financial provider, your goal is to retain and make more money, not incinerate it.
New, the car cost about $98,000 before tax. This one was selling used for $89,000. The previous owner had it for two months, decided he wanted the larger version, traded it in, and took a small bath.
I wanted the car. But I had just spent $3,000 fixing a coolant leak and an inoperable rear right window and door. So I shelved the idea and figured I’d reconsider after returning to Hawaii a month later.
When I got back, the car was still available, but the price had been lowered to $85,000. Now we’re talking. Still, I needed to drive my car for at least another week to confirm the coolant was truly no longer leaking before making an informed decision.
A week later, my car ran without a problem. And the car I wanted dropped to $80,000. Oh, the temptation as I struggled between cost, safety, and pleasure. But still, I resisted.
Then a week after that, the price dropped to $75,000. Sweet! It’s go time. Maybe I could walk in with a cashier’s check for $68,000 plus taxes and fees and they’d take it on the spot.
At the same time, I was staring down a $1,100 decision on two new 22″ front tires. So I rationalized that if I could haggle the newer car down far enough, it was worth buying, despite the money I had spent two months earlier.
Then It Was Gone
Just as I was about to email the salesperson who let me test drive the car before I left for my trip, I noticed the listing link no longer worked. Noooooo.
I finally had liquidity thanks to newly distributed SpaceX and VCX shares sitting in my brokerage account. I was finally mentally ready to move on and waste a lot of money on a depreciating asset. After 10 years of driving and taking care of my car, my family deserved it.
Alas, the salesperson confirmed it was no longer available. And after a full day of second guessing my second guessing, something unexpected happened.
I felt relieved. No more mental gymnastics balancing safety, reliability, and money.
There was now only one path. Spend $1,100 on two front tires and keep driving the car I already own.
After all these years of disciplined saving and investing for a brighter future, the future made the decision for me to save and invest some more.
Sometimes it’s nice when a financial decision is made for you. Almost like being a kid again, when your only responsibility was to play.
Investing During The Downturn
Back in 2022, the S&P 500 declined about 20% after a euphoric +18.4% in 2020 and +28.7% in 2021. The tech-heavy NASDAQ was even more violent, up +42.6% and +20.7% those same two years, then down -33.5% in 2022.
I tried to keep investing in public equities in 2022. But I would be lying if I said it was easy to invest the same percentage I had during the good times. My portfolio was tech heavy and getting beat up. When you’re losing lots of money, it’s natural to want to clutch whatever cash you have left.
That year, I was offered access to a tier 1 venture capital fund through their friends and family vehicle. I had invested in its 2018 vintage but somehow never got notified about the 2020 vintage, so I said yes.
It felt good to reduce my mental load and let someone else decide when to buy the dip. At the time I was preparing to market my WSJ bestseller, Buy This Not That, while taking care of my 2.5-year-old daughter who was home with us full-time.
So I committed $400,000, with $200,000 to the early stage fund and $200,000 to the growth stage fund. I estimated the VC would call about 30% of the capital the first year, or $120,000, which is more or less what happened.
Now I was tied to the mast. Even if I chickened out on buying the public equity dip, at least $120,000 was going to work. And then perhaps another $120,000 in 2023, and another in 2024.
Taking part of the investing decision out of my hands felt wonderful, and worth the fees.
$100,000+ Swings Before Breakfast
Now compare that to VCX, my public venture capital investment I made in early 2023.
I felt a similar calm when VCX was private and I could dollar-cost average in, quietly building exposure to AI names changing the world. Then it listed on the NYSE three years later, and suddenly I was riding out a lockup like a startup employee whose company just IPO’d. All of the volatility, none of the ability to act.
To decide what to do with my shares once the lockup expired, I spent hours modeling VCX’s estimated NAV for 2026, 2027, and 2028. Then I had to calculate the odds of retail mania returning as we edge closer to the IPO of the fund’s largest holding, Anthropic.
But who can really accurately forecast an NAV with so many moving parts, let alone retail sentiment? Nobody. But I had to try, given years of living expenses were at stake. Without sweet W-2 income, I can’t be too wrong.
The temptation to take profits is high, given my entry point of between $10 and $18.97 a share. But my model says VCX can reach $60+ next year based on current data and expectations. So even though I could sell 3,000 shares and buy my favorite car new after tax, I resist. The potential to provide more financial security for my wife and children is more important.
Sacrifice Is Your Role
Being able to achieve FIRE came from patience, discipline, and taking constant calculated bets. Unless new negative data emerges, I will not sell a single share under $60. And if VCX gets to $60, I will crunch the numbers again before deciding what to do. And so I endure $100,000+ daily swings in one position alone, which quietly grinds away at me.
In the meantime, I distract myself with more writing and pickleball, instead of hoping for more selling so I can buy more. Then it’s Daddy Day Camp every day before the kids start school again. Because providing just money to my children is unsatisfying.
The goal is to push those swings into the background so I can focus on the day-to-day moments. Easier said than done. As the manager of our household finances, I never get to forget. Too much is at stake.
When Your Net Worth Becomes Your Self-Worth
Here’s the part nobody warns you about when you become the family’s provider and de facto investment manager. Your sense of self gets welded to a number you don’t entirely control.
When income is up and the portfolio is compounding, you feel like a good husband and a good father. When there’s a drawdown, or you hold something you should have sold, or you sell something that then triples, you don’t just lose money. You feel like you failed the people counting on you.
Nobody in the house says that, partly because they have no idea what’s happening with the investments behind the scenes. But you do. There’s no whistle at the end of the shift and nobody hands you a review saying you did fine. The market publishes a number every day and you decide what it says about you as a person.
Separating your self-worth from how much you provide is an ongoing challenge.
Don’t Take Your Financial Provider For Granted
After 13 years of grinding in finance, I had forgotten what living pain-free felt like. I only remembered what it was like to wake up feeling normal about three months after I engineered my layoff.
Missing out on that car reminded me how nice it is to have a financial decision taken out of my hands. Because for the 11 years since my wife left her day job as well, I’ve been the primary one navigating the financial waters, making sure we don’t sink. And when the storms come, and new lives arrive to protect and feed, that weight can feel immense.
Is there any wonder why so many men and women are opting out of marriage and parenthood altogether? It’s hard enough to build financial security for yourself without The Bank of Mom & Dad. Add children and the pressure to provide climbs to a level that’s hard to explain until you’re in it.
I don’t blame any man for wanting to be a stay at home boyfriend or a stay at home husband. Who the heck doesn’t want to be provided for.
I realized back in 1999, when I graduated college, that there was nobody I could depend on for financial security. My parents were already thinking about retiring from their modest-paying government jobs. So the only solution was to generate enough passive income to break free one day.
If you have a partner who is the main or sole financial provider, please do not take them for granted. They are likely carrying more stress than you’re aware of, and possibly more than they’re aware of themselves.
As the household finances hopefully grows, the stress often grows with it, because more is at stake.
Close The Loops You Can
The money is one thing, but the open loops are a constant strain. Every unresolved decision, every position you haven’t trimmed, every year of tuition you haven’t funded stays open in the background, quietly burning energy your family only experiences as you being a little distant at dinner.
So build decisions that close by themselves.
Automatic investing every month. A written target asset allocation. A capital call schedule from a fund that doesn’t care about you mood. A target price to buy or sell to help reduce emotion from your decision. Assign a reason for your investments. The point of a rule isn’t precision. The point is to stop having the same argument with yourself every morning.
And if you’re not the financial provider in your household, the ask is simple. Ask them what they’re worried about. Not the balance. The worry. Then tell them you appreciate what they carry, and that you could happily downsize to a cheap and tiny house if things ever go sour. They might finally open up, and feel lighter for it. You might even save their life.
Meanwhile, I’m still driving the same 2015 SUV, soon to have two fresh front tires. But if that black on black 2026 model comes back at $65,000, my provider brain and I are going to have words.
Reader Questions
If you’re the primary provider or the one managing your family’s investments, how do you disconnect your sense of self-worth to the rise and fall of your household’s net worth? Has anyone in your household ever asked you what you’re worried about?
What financial decisions have you deliberately taken out of your own hands, and did outsourcing them actually reduce your stress or just move it somewhere else?
Have you ever felt relieved to miss out on a big purchase you thought you wanted?
And for those of you who aren’t the provider, how do you support the person carrying the load?
Get A Free Financial Checkup
If you have over $100,000 in investable assets, take a moment to get a free financial checkup with Empower. Half the burden I described in this post comes from not knowing whether the plan actually holds together. The other half comes from knowing, but never saying it out loud to anybody.
A checkup solves for both. You get a second set of eyes on your asset allocation, your fees, and your retirement projections, from someone who isn’t emotionally attached to the positions you picked. I’ve run my own numbers through Empower’s free dashboard for years to track my net worth, x-ray my portfolio for hidden fees, and stress test my retirement plan against different return assumptions.
There is no cost or obligation to speak with a financial professional. Just don’t be surprised if they find a 401(k) fund quietly charging you 0.75% a year for the privilege of underperforming the index.
Empower is a Financial Samurai affiliate partner. The opinions expressed here are my own.
