OWN THE WATCH
Week ending May 22, 2026
Good morning {{first_name|Reader}},
Most people's biggest career regret isn't a bad move. It's no move at all. This week:
Why 66% of workers regret staying too long, and what that fear actually costs over five years
300 people stood in line at 4 AM for a $400 pocket watch they can't wear on their wrist. We need to talk about it.
The $48,000 earnings gap between people who make the move and people who don't
There's also something personal I've been working through. Not ready to share the details yet, but it connects to everything in this edition. More soon.
OBSERVATION
The Move You Keep Not Making
You've been thinking about it. The career change, the conversation with your boss, the application you've had open in a tab for two weeks. You know something needs to shift, but you haven't done anything about it. Not because you don't want to. Because you're afraid of getting it wrong.
You're not alone. According to Zety's 2026 Job Search Split Report, 47% of American workers plan to look for a new job this year. But 53% plan to stay put, not because they're satisfied, but because the job market feels too uncertain to risk a move. Gallup's data tells the same story from a different angle: 51% of employees are watching for or actively seeking new work, matching a decade high. The desire to leave is everywhere. But few are doing it.
The Regret That Comes from Standing Still
According to Resume Now's 2025 International Career Regrets Survey, 66% of workers report career regrets. The top three are all about things they didn't do: not asking for a raise (60%), not prioritizing work-life balance (59%), and staying at a job too long (58%). Only 38% regretted quitting.
Read that again. More people regret staying than leaving. The fear of making the wrong move is real, but the data says the bigger risk is making no move at all.
A separate CNBC report from March 2026 found that 58% of workers in AI-impacted sectors want to change careers, but only 14% have taken any concrete steps. The gap between wanting change and doing something about it is massive, and it's not closing.
Career Regrets: Inaction vs Action
66%
of workers report career regrets. Most are about things they didn't do.
Regret staying at a job too long
58%
Regret quitting a job
38%
60%
regret not asking for a raise
59%
regret not prioritizing work-life balance
Source: Resume Now International Career Regrets Survey, 2025 | 1,000 workers across U.S., U.K., France, Germany
What Fear Actually Costs You
The cost of staying isn't always obvious. It's not a single bad day or a dramatic breaking point. It's the slow accumulation of years spent in a role that stopped fitting a long time ago. It's the compound effect of not building toward what you actually want because the path there felt too risky.
Work-optional living requires forward motion. You can save aggressively, invest wisely, and build a financial runway, but if your career is stalled because you're afraid to make a move, the math only gets you so far. At some point, the decision to stay becomes more expensive than the decision to go.
WATCH
Swatch x Audemars Piguet Royal Pop
What it is:
Eight Bioceramic pocket watches inspired by the AP Royal Oak
Lépine (open face, hours/minutes): $400
Savonnette (hunter case, small seconds): $420
Hand-wound Sistem51 movement, 90-hour power reserve
Boutique-only, one per customer, no online sales
Launched May 16, 2026
The Royal Pop is the third entry in Swatch's hype collaboration playbook, following the MoonSwatch and the Blancpain Scuba Fifty Fathoms. This time the partner is Audemars Piguet, and the product everyone expected was a plastic Royal Oak for your wrist. Instead, Swatch delivered eight pocket watches on lanyards. (gross)
To be fair to the product: the specs are legitimate. A hand-wound Sistem51 with 90 hours of power reserve, Nivachron anti-magnetic hairspring, sapphire crystal front and back, and a visual power reserve indicator through the caseback. At $400, the engineering is real. Audemars Piguet is donating 100% of its proceeds to fund watchmaking apprenticeships. Those are good things.
But the question you should ask before standing in a 300-person line at 4 AM is simple: what are you actually buying?
You're not buying a Royal Oak. You're buying a pocket watch in a plastic case that borrows the octagonal bezel shape. You can't wear it on your wrist without an aftermarket strap. The resale market is already showing flips at 3 to 5 times retail, which means most of the people in line aren't there because they want a pocket watch. They're there because they want a transaction.
That's the opposite of intentional ownership. The Royal Pop is designed to create scarcity, generate lines, and produce social media content. The product itself is secondary to the event of buying it. Don’t fall for it.
At around $400, you could buy a Seiko Presage with a real automatic movement on your wrist. Still under $1,000, you're at a Tissot PRX Powermatic 80. Those watches don't require standing in line, won't lose their novelty in six months, and actually tell time on your wrist without a workaround.
If you genuinely want a pocket watch with Royal Oak DNA because it speaks to you, go for it. But if you're buying it because of the line, the hype, and the Instagram post, ask yourself whether that's the kind of collector you want to be.
View the collection (or don’t): https://www.swatch.com/en-us/royal-pop.html
NUMBER
$48,000
That's roughly how much the average worker earning $85,000 leaves on the table over five years by staying in a role instead of making a strategic move.
The math is straightforward. According to ADP's 2026 pay research, job changers see a median year-over-year pay increase of 6.4%. Job stayers are getting 4.5%. That's a 1.9 percentage point gap that looks small in any single year but compounds quickly.
Take someone earning $85,000 today. At 4.5% annual raises, they're making about $105,700 after five years. If they'd switched jobs in year one and continued earning at the 6.4% rate, they'd be at $115,900. That's a $10,200 difference in year five alone, and the cumulative gap across all five years totals roughly $48,000 in lost earnings.
And that's the conservative scenario. During the post-pandemic peak in 2022, the gap between switchers and stayers was 8.4 percentage points, according to ADP. Job changers were getting 15%+ raises while stayers averaged 7-8%. The window was wider then, but even in a cooled market, the math still favors the person who moves.
The counterargument is real: the gap has narrowed. CNBC reported in March 2026 that switchers were only getting 4.4% versus 3.9% for stayers using Atlanta Fed data. In some months of 2025, stayers actually out-earned switchers for the first time since the Great Recession. So switching for the sake of switching doesn't guarantee a windfall anymore.
But that's not the point. The point is that staying in a role you've outgrown has a measurable cost, and it compounds every year you don't act. The fear of making the wrong move has a price tag. Over five years, for the average earner, it's roughly $48,000.
The Number
$48,000
Cumulative earnings gap over 5 years.
Staying at 4.5% vs switching at 6.4%. Based on $85K salary.
Year 1
Switch
Stay
$90,440
$88,825
Year 3
Switch
Stay
$102,400
$97,000
Year 5
Switch
Stay
$115,900
$105,700
5-Year Cumulative Gap
~$48,000
Based on $85,000 starting salary. Stayer rate: 4.5% annual (ADP 2026). Switcher rate: 6.4% median (ADP 2026). Cumulative gap includes total earnings difference across all 5 years.
The numbers don't require a strong opinion. They just compound.
The Takeaway
The data on career regret is consistent: people regret what they didn't do far more than what they did. They regret staying too long, not asking for the raise, not prioritizing the life they actually wanted. And in a labor market where nearly half the workforce wants to leave but won't, the gap between intention and action is widening.
The Royal Pop is the watch version of that same paralysis. Hundreds of people stood in line for hours to buy something they don't need and can't wear on their wrist, because the culture told them it was worth chasing. The $48,000 compounding cost of staying in the wrong role works the same way in reverse. Every year you don't move, the gap gets harder to close.
Work-optional living requires momentum. Saving matters. Investing matters. But so does putting yourself in the position to earn what you're actually worth. That might mean a hard conversation, an uncomfortable transition, or a leap that doesn't come with a guarantee. The fear of getting it wrong is real. The cost of doing nothing is measurable.
I've been thinking about this a lot lately. More on that soon.
Have you been putting off a career move you know you should make?
Time is wealth. Own it.
Ian
P.S. Looking for your next watch? I help readers find the right one for their budget and lifestyle. Click here to get started.

