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. Let’s go on a memorable adventure.
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.
For dinner, we went to Smith & Wollensky, a nostalgic spot where I used to dine in New York City while going through seven rounds of interviews at GS. The firm gave me a $100 daily meal budget during that time. We also went to Lavo for Italian.
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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I’ve been writing about money from firsthand experience since 2009, and I’ll keep sharing the real stories, full of ups and downs.
Great picture after the late-night big loss, you hold up well. Thank you so much for all your articles, they have been my favorite for 10+ years.
Glad you are learning to be less of an optimizer ;)
Great post! We all need to relax on how much we spend when it really doesn’t affect the bottom line. Many of us have done VERY well. A coworker was always complaining about gas prices. BTW – he drives a gas guzzling truck. I got tired of hearing his whining and asked if the gas prices made him change his spending habits or affected his lifestyle at all. His answer, “No”. My answer – “Consider yourself very, very lucky. There are countless people who are hurting financially due to the higher gas prices. They don’t drive as much, eat as much, spend as much. You have a great life. Keep enjoying it and stop whining.” I meant every word. lol
I have to say Sam that you are the youngest 49 I ever saw, great post!
Haha, thanks! Very kind of you. I’m sure the hat makes me look younger as I slowly lose more hair. Haven’t figured out how to use the photo filters yet. Maybe when I’m 60.
But one thing that did happen after I left my job in 2012 is that all my grey hairs went away, and have stayed away 14 years later. There’s a silent stress I didn’t know I carried until 6 months later.
Related: The Health Benefits Of Early Retirement Are Priceless
I thought the same, great photo, Sam (and wife!).
Hey Sam, thanks so much for this article. I walk in your shoes often.
I was out to dinner with some blue-collar friends, the kind where there’s 1 pension coming in and 2 others pending. The wife’s parents have bought their groceries for their entire 20+ yr marriage, running it through their own blue-collar company. This couple is hard working, has great kids, and as a family they spend freely, and are generous. They never worry about money. So the wife tells me about how she failed out of her first college, her parents paid for her to travel down under for a year, and, unlike how I was raised, there was never a lesson on achieving, toughening it out, paying her own way, etc. As a wall st family, we can retire today and never run out (knock-wood), yet I stress about getting the ‘tap’, return on capital, tax optimization, etc. During the time of this dinner, our son was having a terrible time at a stupidly hard university and after this conversation it hit me to loosen up. After finals I took my boy on a 2 week European trip, just the 2 of us (dh couldn’t get away), stayed at fabulous hotels, and even left a pre-paid hotel when I wanted a nicer location. There were no conversations about not spending, how lucky he was to have a paid for trip, etc. I came to know my son in a way that you only get when you’re traveling together in foreign-language countries. (He’s a great person btw.) When I came home, my investment returns in that time had far exceeded the cost of the trip. The trip helped my son distance from the hated uni, and he transferred to a new one he’s liking. *I’ll never regret that trip*.
Sounds like a priceless trip! Glad you guys reconnected and bonded further.
Incidentally, surveys show that people with pensions spend much more of their money in retirement than those with 401k/IRAs. Imagine that most of your readers are in the latter category. After a lifetime of saving for later, it’s not so easy to spend. Kinda makes you wonder if we all picked the wrong path ;-)
Why do you gamble if you are that worried about money? Seems like unneeded stress that ends up affecting loved ones.
True. I set a budget of $500, and viewed it as entertainment and also as a chance to win. I have about an 80% winning record over the last 20 years.
It’s always good to review decisions and retrospect. Maybe I would’ve been happier if I had one $350. But I didn’t think I was unhappy or irritable or impatient to begin with that morning. Red rocks was really amazing.
Hi Sam
Thats really good if you win 80% of the time
How about we make a wager for charity?
I will play you no limit poker. We both put
up 10k and the proceeds go to the winners
charity?
You pick the spot
Seems like a great opportunity for your
charity?
JJ
Could be fun! But you have to promise not to drink heavily and keep things pleasant. For our last bet of $5,000, some of your emails were unhinged after your lost. It’s important to keep things light and fun.
What’s the maximum you’re willing to bet? And would you be willing to fly to Honolulu? I’ll be there during the holidays for a couple weeks.
Sure Sam, too much alcohol is never good.
I apologize for those comments. I am in the Cayman Islands over Christmas time. Pick another time, let’s keep it fun. I do appreciate what you do and look forward to
your posts
So I would wager 21 k divided between 3 charities
We could do it in Tahoe,
Vegas, San Jose, Ventura, or Bristol
I remember a number of years ago I was stressed about money and we were driving home together since we worked together.So she says look at that homeless man standing on the corner. Then she says do you think he lost any money in the stock market today. So that puts it in perspective.
Good perspective. Always good to anppreciate what we have.
Although, it’s kind of nice not to have any money during a downturn.
I remember during the Global, financial crisis, my boss was trying to console me on my terrible bonus. And he said, “you should be happy you make so little. I’m getting crushed here making so much.”
I was attending an IT Cybersecurity conference with a couple of other senior partners when I got the call from the CEO. I had sold my company to them a couple of years prior and the company had recently lost a couple of major clients. They couldn’t afford to keep me on board anymore. I had equity in the company, but was also just another employee. There’s a longer back story, but I ended up staying for about another year at a severely reduced comp plan. It was an extremely stressful and difficult time even though on paper I had zero financial reason to keep working. I could have retired then, but my pride and ego would not allow it. The looming issue was we had a two week vacation planned for the Carolinas and then off to the Bahamas for a week on a sailboat. I was super stressed about the situation. They were going to lay me off, but wait! I have a big vacation planned the next month. As it turned out, the vacation was exactly what I needed and my family needed. I actually closed a deal at the airport on the way out, and then I was done with work for 2 weeks. Didn’t think about work again the entire time. Enjoy your time in Las Vegas with family. The money will always be there!
Everybody makes mistakes. Not Everyone admits them.
Thank you for trying to help us learn by yours.
OK that picture is fine! But you’re right…she was probably stressed too. Pick your battles. Let me tell you- I’ve been married for 35 years.
Thanks. It’s after the fact.
When you’re being photographed, you have no idea what the outcome is because you cannot see the picture after it is snapped. I just asked for a different angles given snapping is free.
The setting was majestical, so I didn’t take into consideration she could have been stressed. So it’s important to put myself in her shoes and not be quick to judge next time.
Happy to see this post Sam. After reading this I just added two extra days on my road trip and not going to worry about the extra money that will be spent. I am going to enjoy it and not fret over a couple thousand dollars. Thanks.
I LOVE the shirt….great post.
Hang in there Sam, sounds like you’re human and continuing to learn everyday.
Cheers!!
I love it too, which is why I thought it would be a fun profile pic. It’s so true as a parent to young children :)
Sam, another fantastic middle-age point of view and just full of common sense. I would add a 4th point for a middle-age financial provider, and that is especially if you have enjoyed some investment success is to stop trying to hit home runs and be satisfied with double, triples, and even some singles. What a great picture of you, thx for sharing and thx for listening.
Great article Great photo! Thanks for sharing!!
Vegas! So glad you went together. Even though it’s known as an adult destination there’s actually tons of great activities to do with kids there. And that’s great you also got to do an excursion to mix things up. There’s so much surrounding beauty and Red Rocks is quite an incredible place. It’s also so cool to see lots of rock climbers there. Great pic too!
Sam, I think you’re being awfully hard on yourself. I also think what you are feeling is very normal. Imagine being stretched ALL the time! That bit of anxiety, noticing how much every single thing costs, annoyed at gas prices, annoyed when kids ask for things for the 10th time that day, annoyed when the wife suggests we get take out for $100 after a busy week. “The silent burden of the primary provider”. This is very real for me; especially now after taking a medical retirement. You elude to this, but we have to realize we’ll be ok and that all our hard work and aggressive investing over the last several decades is exactly what these moments are for. Us type A personalities have a hard time chilling out, it’s how we’re built but it’s also how we got our successes and ultimately how we provide.
Life is interesting, isn’t it? Why do we feel the way we feel? And what can we recognize about ourselves to change to make things better for others.
Introspection can reveal a great deal if we let it happen.
Great picture!