A couple days before I published Broke Again At 49, my wife said going to Las Vegas over the long weekend would be a lot of fun.
I had floated the idea a couple weeks earlier. Unbeknownst to me, she then spent several hours over several days researching hotels, flights, shows, and costs to make it happen. The holiday was only nine days away, and she wanted to lock in good seats and better rates before they disappeared.
Normally, I’d be thrilled by this level of initiative. Vacation planning for four is not easy. The logistics alone are complicated, especially with food allergies and disruptive sleep patterns.
But I wasn’t thrilled. Between the time I brought up Vegas and the night she did all the planning, I got hit with another $25,000 capital call from a different venture fund.
When it rains, it pours.
So after she walked me through everything, at a total cost of between $6,000 – $7,000 I told her I needed to think about it. Understandably, she wasn’t pleased. I was the one who suggested the trip in the first place. She did the work. And instead of an enthusiastic thank you, she got a “let me get back to you.”
She also didn’t know I was about to publish a post announcing I was strapped for cash again. Ever since the advent of AI, she no longer edits my posts.
The Uncomfortable Position As A Father
Every father wants to give his family the best life possible. I’m no different. It stings when I can’t deliver.
So I had a choice:
- Say yes, and figure out how to dig myself out of another $6,000 – $7,000 hole.
- Say no, and disappoint my wife, and to some extent my kids, by insisting we stay local for the five-day weekend. Then look back with regret at a lost family moment when we were still young and beautiful.
To her credit, my wife said she’d be fine with a staycation. That mattered a lot. It showed she understood our situation even though I hadn’t fully explained it. She also was aware that I’ve been longing to do something different for quite some time, and the long weekend gave us that chance.
A week went by, and I had gone through a money manifesting exercise and raised enough liquidity to meet future capital calls. I didn’t raise the money to spend it. But at least I knew my investment obligations for the next three-to-six months were covered, and that took a huge weight off.
Further, we compromised on three nights instead of four, saving about $1,000 – $1,500.
Ultimately, I said yes for one simple reason. I was the one who estimated a 30% capital call within 12 months. Instead, 46% got called in just six. That was my mistake, not theirs. I wasn’t going to make my family pay for my bad forecasting.
When you’re the provider and you mess up, you own it. Even if your intention was to invest for your children’s future, the people who had nothing to do with your decision shouldn’t be the ones absorbing the cost.
No Complaining Allowed
Before agreeing to the trip, I made myself a promise: no grief about the hotel, the shows, or anything else she picked due to money. Going on vacation and stressing about money every day is the worst of both worlds. You spend the money and still don’t get the joy.
We booked two adjoining rooms at the Palazzo so we could spread out instead of cramming four people into one room. Thanks to my wife, we got great seats to Blue Man Group, Cirque du Soleil, and Popovich Comedy Pet Theater, the show starring rescue animals. Closer seats were important to help our son see more clearly.
Tickets averaged between $450 – $500 per show for the four of us.
We also went to the Illusions Museum, the Flyover, and took a tour out to Red Rocks, which was spectacular.
The kids had a blast. Mission accomplished.
The Small Moment That Ruined My Day
The night before Red Rocks, I played poker from about 9:40pm until 1:30am. I was doing fine until I lost $350 in a bomb pot. My full house got beat by a bigger full house after my opponent flopped top set. That’s poker. No crying at the casino.
I went to bed at 2am and promised my wife I’d be up by 6am to bring back breakfast before our 7:30am departure. My wife and daughter aren’t morning people. I am. I spent 13 years waking up before 5am in finance, so four hours of sleep felt manageable.
At one of the Red Rocks vista points, I asked my wife if she could take a few portrait shots of me for my newsletter or future media requests. I didn’t have an updated profile picture since 2025. She said sure.
After snapping some shots, then I asked if she could raise the camera to my eye level, since she’s nine inches shorter, and switch to vertical. That’s when I noticed she was getting irritated. When she finished, she handed back the phone without looking at me.
I felt hurt. I thought it was a simple request.
It also stirred up an old feeling of being a burden. I almost never post pictures of myself because it feels superfluous and awkward. I don’t celebrate my birthday either, since it falls in June when school is out and everyone’s busy.
I’m the one who takes the pictures, which I enjoy. The footage is often a surprise when you look back, and it captures moments that disappear too fast.
So asking someone to take photos of me already felt uncomfortable, even if that person is my wife. Asking for retakes with directions felt worse.
The Problem Was Me
With some distance, I’ve come to realize I’m the problem.
She had already taken a bunch of shots. Then I started giving camera direction like a fussy fashion photographer. Raise it. Turn it. Eye level. Vertical. On four hours of sleep and $350 lighter, my tone was probably more critical than I realized.
I should have just trusted her. She’s taken thousands of great photos of our kids. She didn’t need coaching.
And I bet she had her own stress. She planned the entire trip, got up early, wrangled two kids through a casino city, and was dealing with a husband who’d been quietly anxious about money for weeks. Being on the receiving end of that energy isn’t fun.
When you feel money stress, small interactions get magnified. A neutral look feels like rejection. A sigh feels like a verdict. A nothing-burger becomes a full meal of self-doubt. And you might not even realize what the stress is doing to you until a blowup happens.
We must control how we react to suboptimal situations.
The Silent Burden Of The Primary Provider
Men are often taught to bury our feelings. If we admit we’re stressed, scared, or worried, we assume we’ll be seen as less capable. So we soldier on through bear markets, layoffs, and capital calls, and keep grinding. Most of us make it through. Some of us sadly don’t. While others simply opt out of family formation altogether.
The same goes for any primary provider, regardless of gender. When the household depends on your income or your investment decisions, every bad outcome feels like your personal failure. And because you don’t want to worry anyone, you often carry it alone.
The problem is, stress doesn’t stay buried. It leaks out as irritability, sensitivity, and an inability to enjoy the moment you’re paying for.
If you’re the provider: say something. You don’t need to dump every number on your partner. But “I’m feeling stretched right now and might be more irritable than normal” goes a long way to set expectations. Silence forces your partner to guess, and they’ll often guess wrong.
If you’re the partner of a provider: know that the person who seems tense about a $1,200 hotel upgrade or a simple photo request may be carrying something heavier than they’re letting on. A little patience, a thank you, or a “how are you doing with everything?” can mean more than you’d think.
Investing Beyond Your Means Isn’t Worth The Stress
Since 2009, I’ve always told readers to save and invest until it hurts each month. Otherwise, you’re not saving enough. After 10 years of deliberate saving and investing, you’ll likely have far more than you imagined. Compounding sneaks up on you.
But I’ve always taken an extreme approach, and there’s a reason.
The summer after high school, a prank went wrong and I got in trouble with the law. I thought my life was over. I assumed no company would ever take a chance on me.
When one finally did, I swore I’d save and invest as much of every paycheck as possible so I’d never have to depend on someone accepting me again. I didn’t think many would.
Delaying gratification was painful yet comforting. Every dollar saved was a step toward never needing permission again. Luckily, the worst case scenario did not happen.
But now I have people depending on me who had nothing to do with my past mistakes. They shouldn’t have to live under the strain I put on myself. For the sake of harmony and happiness, I need to ease up.
Three Lessons For Financial Providers
1) Keep at least a six-month cash buffer.
From now on, I’m keeping at least six months of living expenses in cash or cash equivalents in my taxable brokerage account. No exceptions.
For years, holding cash felt wasteful because it earned next to nothing. But with money market funds and short-term Treasuries paying a respectable yield, the opportunity cost of sleeping well at night is much lower.
Cash isn’t just a return. It’s emotional capital. It’s what lets you say yes to a family trip without feeling like you’re stealing from your future. If you’re fully invested and a capital call, layoff, or market crash hits, you’re forced to make decisions from fear.
2) Stop optimizing every last dollar.
I’m a recovering optimizer. Saving $1,000 by cutting a night is fine. Spending the entire trip mentally tallying costs is not.
At some point, the marginal benefit of squeezing out another dollar is smaller than the cost to your relationships and your mood. Your kids won’t remember whether you got a great rate on the second room. They’ll remember whether Dad was present or distracted.
3) Don’t miss the whole point of investing
The portfolio: a happy family on vacation, kids laughing at rescue animals doing tricks, a jaw-dropping view at Red Rocks.
The positions: a photo angle, a lost poker hand, a capital call that will be met come hell or high water.
Any investor knows not to let one red position ruin a green portfolio. Yet I let one tiny position ruin an afternoon worth more than any return. Don’t be like me.
Forced Change Is The Greatest Silver Lining
Once you hit middle age, it’s hard to change. It’s why so many couples split over irreconcilable differences. Both sides know what the other wants, both want to stay together, yet sustaining change is impossible.
But just like a near-death experience can make you stop taking life for granted, a stressful moment blown out of proportion can be a great catalyst for change. It shows you what’s actually going on beneath the surface.
I’m tired of optimizing every last dollar. Spending freely in Vegas for four days, minus that bomb pot, has loosened me up. And this change should make me a better husband, father, and personal finance writer.
Oh, and here’s one of the pictures my wife took of me during that moment. Turns out she knew exactly what she was doing all along.
Readers, have you ever felt like a burden to your loved ones, no matter how hard you try to provide? Has financial strain ever made you more sensitive to perceived slights? And for the partners out there, how do you support the provider in your household when you can tell they’re stressed?
Related post: Don’t Let Honor And Pride Keep You On Hard Mode Forever
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