Reader Q&A: Watches, Money, and Discipline

Hey {{first_name|Reader}}.

You asked. I'm answering.

In January, I sent an email asking for your questions about watches, money, discipline, parenting, and building toward work-optional. I got more submissions than I expected, so this is the first of what might become a regular series.

Some of these questions are easy. Some are uncomfortable. Some challenge my own thinking. That's the point.

Here are the ones I'm answering this week.

(I’m always looking for feedback. Let me know! Reply to the email.)

You don't convince her. You earn it.

If you have to convince your spouse that a luxury purchase is justified, you're not ready to buy it. The foundation comes first: emergency fund, no debt, stable income, shared financial goals.

Once those are in place, the conversation changes. It's not "Can I buy this?" It's "We're in a position where I can buy this without hurting our goals. Here's why it matters to me."

Show her the math. Show her the cost-per-wear over 10 years. Show her that you're not sacrificing retirement or your kids' future for a watch. Show her it's intentional, not impulsive.

If you've done the work, she'll see it. If you haven't, she's right to say no.

Used. Always.

Here's why: a new luxury watch loses 20-30% of its value the moment you walk out of the dealer. A used watch has already taken that hit. You're buying it at or near the bottom of its depreciation curve.

You get the same watch. The same movement. The same function. You just don't pay the new-watch premium.

The only reason to buy new is if you want the full warranty, the experience of unboxing it yourself, or you're buying a brand-new release that's not available used yet. Otherwise, save the money and buy used.

Start with Chrono24. Buy from a reputable seller. Get it authenticated. You'll be fine.

Three options:

Sinn 556 I ($1,400): German engineering, anti-magnetic, clean dial, will last 30 years. Tool watch that works everywhere.

Seiko SPB143 ($1,100): In-house movement, 200m water resistance, finishing that rivals watches twice the price. Modern classic.

Christopher Ward C63 Sealander GMT ($1,450): True GMT complication at a price that's absurd. British design, Swiss movement, punches way above its weight.

Pick based on what you need. If you want a no-date field watch, go Sinn. If you want a diver, go Seiko. If you want a GMT, go Christopher Ward.

All three are legitimate watches you can wear for decades.

Keep it. For now.

You don't have to wear it. But don't sell it yet. Inherited watches carry weight beyond their market value. They're connections to people who are gone.

Put it in a box. Let it sit for a year. Maybe two. Revisit it later. You might change your mind. You might not. But once you sell it, it's gone forever.

If you still don't want it after a year, then consider selling. But give yourself time to sit with it first. Regret is expensive.

Foundation first. Luxury second.

Every dollar I earn gets allocated before I see it. Savings and investments are automated. What's left is discretionary. If I want something nice, I save for it from the discretionary pool. I don't touch the foundation.

The foundation is: emergency fund, retirement accounts, taxable brokerage, kids' 529 plans. That's non-negotiable. Once that's funded, I can spend on watches, tools, experiences—whatever matters to me.

It's not deprivation. It's priorities. I don't feel restricted because I know the foundation is solid. The watch is a reward for doing the boring work first.

No.

I don't care if it's 0% interest. I don't care if the payments are small. I don't care if you're "sure" you can pay it off early.

If you can't pay cash for it today, you can't afford it. Wait. Save. Buy it when you can pay in full.

Financing a depreciating luxury good is one of the dumbest things you can do with money. Don't do it.

Not investing sooner.

I had six figures sitting in a savings account earning 3% while the market was doing 8-10%. I was scared of risk. I didn't understand compounding. I wasted years.

If I'd started investing aggressively five years earlier, I'd be years closer to work-optional. That's time I'll never get back.

The lesson: saving is good. Investing is better. Don't let fear keep your money sitting idle.

I automate it before I feel it.

When I get a raise, the first thing I do is increase my automatic savings and investment contributions by the same percentage. The raise never hits my checking account. It goes straight to index funds.

If I got a 10% raise, my lifestyle stays the same and my savings rate goes up 10%. I never adjust to the higher income because I never see it.

This is the only way I've found to avoid lifestyle creep. If the money never touches your hands, you can't spend it.

"We can afford it, but we're choosing not to buy it."

Not "we can't afford that." That's a lie, and it plants a scarcity mindset. They internalize the message that we're struggling, that we don't have enough.

When I say "we can afford it but won't buy it," the message is different. We're financially stable. We're just not buying that for you. It's a choice, not a constraint.

My youngest gets whiny sometimes. But I think all three of my kids respect it. They're learning that money is about choices, not limitations.

We're starting in 2026. My kids are 11, 10, and 8.

I don't have a perfect system yet. We're figuring it out. But the goal is to show them how compound interest works, how index funds grow, and why investing beats saving.

I'm open to ideas from readers. How have you done it? What worked? What didn't? Hit reply and tell me.

I don't worry about sounding mean.

I'm not their friend. I'm their parent. There's a difference.

My job isn't to make them happy in the moment. It's to raise them into adults who understand delayed gratification, intentional spending, and discipline.

Sometimes that means saying no when their friends' parents say yes. Sometimes that means being the "mean" parent. I'm fine with that.

They'll thank me later. Or they won't. Either way, I'm doing my job.

Accountability and replacement.

I told my wife immediately. She kept me honest. I also told a peer who was on the same path. Knowing someone else was watching made it harder to quit.

And I replaced the habit. Instead of having a drink after work, I'd work out. Or write. Or spend time with my kids. I didn't just remove alcohol—I filled the space with something better.

The first 30 days sucked. But by day 60, it felt normal. By day 90, I couldn't imagine going back.

I use the 72-hour rule.

If I want something, I wait 72 hours before buying it. I don't browse. I don't add it to my cart. I just wait.

Most of the time, I forget about it. The impulse fades. If I still want it after 72 hours, I revisit it. I ask: does this fit my goals? Is this a Time Saver, Money Maker, or Legacy Piece? If it fails all three, I don't buy it.

This rule has saved me thousands of dollars on things I would've regretted.

I go to bed early. And I have a reason.

I'm in bed by 8:30 PM most nights. That gives me 7.5 hours of sleep. I don't negotiate with myself in the morning. The alarm goes off, I get up.

But the real reason I wake up early is because I want to. I have work to do. This newsletter. Workouts. Thinking time. If I don't do it at 4:09 AM, it doesn't get done.

The motivation isn't discipline. It's purpose. I wake up because I have something worth waking up for.

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These questions keep me sharp. They force me to articulate what I believe and why. Some of my answers will age poorly. Some I'll disagree with in a year. That's fine.

If you submitted a question and I didn't answer it this time, I'll get to it in a future Q&A. Keep them coming.

Question: What question would you ask if you could guarantee I'd answer it? Hit reply and tell me. I'll use the best ones for the next Q&A.

Watches count time. Your choices make the time count.

—Ian