The $5,500 Holiday Trip We Didn't Take

Good morning {{first_name|Reader}}.

Merry Christmas to everyone who celebrates. It's the holiday week and I've been spending as many hours as I can with my kids. Watching them open presents. Being present. Not rushing anywhere.

I'm relieved and exhausted at the same time. The holidays take more out of you than you expect, even when you're not traveling. The energy is starting to build back up, which is good because I'll be traveling for most of February 2026. But that's a problem for future me.

This week: a watch that's better than a Submariner in almost every way except the logo, the $5,000+ holiday trip we didn't take, and the friendship audit I didn't plan to do.

Let's get into it.

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I don't own this watch.

I don't own this watch. Full transparency. But it's been catching my eye lately and I wanted to break it down for you because I think it's one of the sharpest dive watches on the market right now.

Let's address it directly: everyone compares dive watches to the Rolex Submariner. So here's the breakdown between the Pelagos 39 and the Submariner 16610.

Why the 16610? Because it's 40mm (close to the Pelagos's 39mm), it's the black Submariner you see most often in the wild, and it's actually available on the secondary market without waitlists or spending games.

Here's the side-by-side and check out this article from Time & Tide for more:

Titanium. That's the headline. It's lighter, more comfortable for all-day wear, and more scratch-resistant than steel. The no-date dial is cleaner. The T-Fit clasp is one of the best micro-adjustment systems on any bracelet at any price. The lume is exceptional.

In terms of actual performance as a tool, the Pelagos does everything the Submariner does. Water resistance is 200m vs. 300m, but unless you're a professional diver, that difference doesn't matter. Both are COSC-certified. Both keep excellent time. Both are built to last decades.

Brand recognition. Resale value. The Rolex name gets you into a club that many people aspire to join. The Submariner holds its value better—significantly better. A well-kept 16610 can sell for $9,000–$12,000 on the secondary market. A Pelagos 39 is currently around $3,550–$4,000 used.

If you want to be able to sell your watch later and get most of your money back, go with the Sub. If you care about what other people think when they see your watch, go with the Sub.

But here's the thing: the Pelagos is more affordable, more attainable, and more of a conversation piece. Fewer people will recognize it unless they're watch enthusiasts. And that's either a dealbreaker or the entire point, depending on who you are.

I know about eight people with a black Submariner. I know zero people with a Pelagos. I know one person with a Tudor Black Bay, but that's it.

Does being different matter? That's for you to answer. Do you want the name recognition of a Rolex? If so, there's your answer. Do you want a luxury watch that's still practical and doesn't scream for attention? Maybe the Pelagos is the move.

If you already own a Rolex, do you need another one? Many ways to answer that question. Maybe yes. Maybe no.

Would I buy this watch? Yes. It's an incredible watch at a more affordable price than a Submariner that you can buy online today without playing waitlist games or building a spending history with an authorized dealer. (I’d look for it on the used market for a good deal. The Laughter Collection is your best bet for authentic, luxury watches)

Who should skip this? Logo chasers. If the Rolex crown matters more than the watch itself, this isn't for you.

If someone has $5,250 to spend on a dive watch, is this the move? It's one move. You could also buy this, or several other great dive watches, or not buy a watch at all and fund your retirement account or save for a trip.

The point is: this watch is a legitimate option at this price point that doesn't require you to beg a dealer for permission to buy it.

This Week’s Breakdown

Starting net worth: $XXX,XXX
Contributions (savings): $X,XXX
Investment additions: $X,XXX
Market gains: $X,XXX
Ending net worth: $XXX,XXX

(premium subscribers will see our actual numbers below)

We didn't travel for Christmas this year. We stayed home in Alaska with our three kids. No flights. No rental cars. No coordinating schedules with extended family. Just us.

A lot of young families get guilted into traveling for the holidays. We don't have any family where we live. We could have flown to North Carolina or Ohio to see parents. We didn't.

(click to read more)

Last summer, round-trip flights for a family of five from Alaska to North Carolina cost $5,000. That's just airfare.

Add in:

Total cost if we'd gone: roughly $5,500–$6,000.

We would have stayed with family, so no hotel costs. Food would have been mostly free. But the time cost, the stress cost, and the exhaustion cost don't show up on a spreadsheet.

It was never an option this year. We get so few days off together as a family that traveling was off the table from the start. Traveling during the holidays is exhausting. I know so many people who travel for Christmas and come back to work feeling like they had no time off at all.

My wife and I were on the same page. No debate. No guilt. (Though many do suffer guilt from families) We've experienced guilt from family in the past—the covert contracts of "Oh, we just assumed you were coming this holiday..."—but not this year.

Here's the truth: I'm a grown man with my own family. When I decided to get married and have kids, they became my family. They're the ones to whom I owe my time and attention. Everyone else moved to the back of the line. That sounds harsh, but it's true..

We spent Christmas Day together. Opened presents. Enjoyed being around each other. No schedule. No rushing. No coordinating with anyone outside our house.

Staying home gave us time, control, and less stress. My kids didn't seem to care that we weren't traveling. They had a great Christmas.

The $5,500 we didn't spend stayed in the bank. It's there for future use—maybe a trip we actually want to take, maybe an investment, a watch, maybe nothing specific yet. The point is, we didn't bleed it on a trip that would have left us more exhausted than rested and there are benefits of staying home!

Do I feel guilty about not going? Not at all. People are always welcome to visit us. The people we'd be visiting don't have young kids, so I find it odd that the family with three children is expected to be the ones doing the traveling.

The hardest part of not seeing family during the holidays? I don't see it as hard. I spent Christmas with my wife and kids—my real family.

Is this about money? No. It's about boundaries and priorities. Even if money wasn't a factor, I'm not sure we'd have gone. We live in Alaska. Visiting people is a significant emotional event. It's not a two-hour drive. It's a full production.

Is this permanent? Not forever. We're not closed off to holiday travel. But we'll do it when it makes sense for us, not because someone else expects it.

Looking back, do I regret it? Not even 1%. No regrets.

I looked at my phone this holiday season and realized something uncomfortable: fewer than five people reached out to me. Text messages don't count—that's a lazy way to pretend you're still connected. I mean actual calls or meaningful contact. Is it JUST me?

I reached out to three people.

I scrolled through my messages. Most of the conversations end with me as the last person who sent something. I give effort. I call with no return calls. I text with no answers. I'm done with it.

I want connections. I want friendships. But if people are too busy to respond, then I'm not important to them. And that's okay. I'll give equal effort back, which means none. I'll take that time and energy and put it back into myself or my family.

This isn't a game. I don't do that.

This has been happening for years. People say "let's keep in touch" and I hold up my end. They don't. I've confronted people about it before. It didn't change anything. And that's fine.

The holidays just made it more obvious. Lots of text messages in my phone as I scroll down, and most of them are me as the last person sending a message. That pattern isn't just during the holidays. It's all year round.

I've already let go of so many friendships that there are too many to count. I'm not confronting anyone else. I'm just stepping back. They're missing out.

How does this connect to my goals? I'm laser-focused on being work-optional by my forties, being present with my kids, and building this newsletter. If people don't want to come along, I'm not pulling them.

I feel very lonely. It sucks. I want other guys to talk to about things. I want to grow with people who have similar goals and standards.

Do I worry I'm being too harsh? Yeah, probably. But I have high expectations and high standards. I need to be focused. Many people who say they're focused really aren't.

Has anyone noticed me pulling back? No. Not one "hey, haven't heard from you" text. That tells you everything.

If you're putting in more effort than the other person, maybe it's not worth it. If you want to be friends more than they do, maybe it's time to move on.

Is there a scenario where a one-way friendship is worth keeping? No. The whole "blood is thicker than water" idea is nonsense. You don't owe people anything just because they created you. That sounds harsh, but they have to hold up their end to be worth your continued time.

A less-known watch. Less travel. Fewer friends.

The Pelagos 39 is a better watch than most people realize, but it doesn't have the Rolex logo. The $5,500 trip would have been exhausting, not restorative. The friendships I'm letting go weren't friendships—they were me doing all the work.

Not everyone deserves to come along on your journey. And that's okay.

Focus on what actually matters. Cut the rest.

Watches mark time. The choices behind them mark intentions.

—Ian