I earn over $260,000 as a CEO, but I'm still a HENRY. Big titles don't always mean big wealth.

Shaun Michael Lewis.Courtesy of Shaun Michael LewisShaun Michael Lewis, a real estate CEO, has worked in many sectors and considers himself a HENRY.Lewis transitioned from federal work to private sector roles and has invested in his wife's company.Despite high earnings, lifestyle inflation and strategic career pivots impact his financial status.This as-told-to essay is based on a conversation with Shaun Michael Lewis, a 42-year-old real estate CEO in Whitefish, Montana. It has been edited for length and clarity.Growing up in the '90s, I saw how my father and grandfather spent their entire careers at a single company. My dad worked at PG&E for decades, and my grandfather was an engineer at HP his whole life. That was the promise then: a pension, job security, and retirement.I'm part of what may be the first generation that doesn't broadly believe Social Security will be there when we need it. That shaped many of my early career choices, and I gravitated toward federal government work because it felt safe.After a few jumps around industries and the globe, I'm now a CEO. My personal income is about $264,000 a year. Combined with my wife's income, we're solidly high earners.However, if you asked if we could retire tomorrow and maintain our current standard of living, the answer would be no — we're considered HENRYs.I started my career in the military and for the governmentI joined the Navy and spent almost a decade working for the US Department of Justice and the Department of Veterans Affairs. I was doing well — I hit six figures in my early 20s and managed large teams — but there was a nagging feeling that something was missing. Love Business Insider? Log in to Google and make us a preferred source. Seven or eight years into my federal career, I asked myself, "Is this really what I want to do for the rest of my life?" I felt an enormous, crushing feeling that this wasn't the right path for me. I took a chance and switched tracks.I left stability to get my MBAI enrolled at the University of Washington to pursue my MBA and subsequently completed Harvard Business School's Executive MBA program. Leaving the federal government was unheard of among my peers. You just didn't walk away from a guaranteed pension — but I did.My first major private sector role was as COO at Clearwater Properties, a large, multi-state real estate company, in 2016. That was a massive leap from the safety net of federal work to the volatility of the private sector. I'm proud of that decision because it marked a complete shift in how I thought about risk. Previously, I was quite risk-averse. I then realized I could bet on myself and come out ahead.In 2020, I accepted a global executive position with Cofix, an international coffee retail chain based in Europe. When I quit my job in the US, I didn't even have the offer in hand. I just packed up, put my stuff in storage, and went to Tel Aviv, Israel, the headquarters, for the in-person interview.Following discussions with the CEO and Board of Directors, we mutually agreed that Moscow would be the optimal location for my role. The CEO was based there, and Russia represented our fastest-growing market at the time. My wife and I relocated there together.Life abroad was challenging in a new wayThat international role came with its own set of challenges. I led seven countries, including Russia. When the conflict in Ukraine broke out, sanctions made things very difficult, and the reputational damage was significant. The same happened when the Israeli-Palestinian conflict flared up; our company was founded in Israel.It was a massive learning curve: managing dual households across continents in Moscow and Warsaw, Poland, converting currencies, and trying to build real purchasing power amid volatility and geopolitical risk.After spending five and a half years in Europe, I returned to Clearwater Properties as CEO in 2025. In hindsight, that chaotic time abroad was exactly what prepared me to lead this company.Why am I a 'HENRY' at 42? A few reasons stand out.First, every strategic career pivot I made required a reset. New cities, new homes, and new costs. I was always building, not accumulating.Second, living and working abroad means maintaining more than one home. I spent years flying back and forth, paying for housing in multiple cities, and absorbing the higher cost of living in major cities.Third, lifestyle inflation is real. As your income grows, so does your spending, especially when you run in elite circles. I'm a Harvard Business School alum, and keeping up with that network comes with a cost: private club memberships, alumni events in far-flung places, and international travel.Fourth, my wife and I make big bets. She left an impressive corporate career to launch a startup that we fully bootstrapped ourselves. It's doing well, but the conflict in Europe has definitely changed the market's dynamic and what would've likely been dramatic growth.These choices have kept us buildingI'm passionate about my work when I have the autonomy to execute my vision, which is certainly the case in my current role. My philosophy is that retirement should be a choice driven by personal fulfillment rather than financial necessity. As long as my passion and work-life remain aligned, I could envision working well into my late 50s or beyond.However, I would ideally like to have the flexibility to step back in my early to mid-60s to focus on travel, passion projects, and leisure pursuits.From the outside, people assume that big titles mean big wealth. I run a multi-state real estate company that handles over half a billion dollars in annual transactions. But you don't get to pocket all that, and the reality is that you're working because you have to, not just because you want to.Do I sometimes feel behind my peers? Sure. However, I believe that the calculated risks I took — such as the zigzags, career resets, and geopolitical curveballs — will pay off. I'm not there yet, but I can see it on the horizon.Are you a HENRY and want to share your story? Email this editor at [email protected] the original article on Business Insider

Comments

Business News

Homeowner property repossessions in 47% annual jump but mortgage arrears falling

Evening Standard

Researchers built a social network made of AI bots. They quickly formed cliques, amplified extremes, and let a tiny elite dominate.

about 6 hours ago

Drake Baldwin Takes Charge Of National League’s Rookie Race

Forbes

Comments

Business News

Homeowner property repossessions in 47% annual jump but mortgage arrears falling

Boohoo founder should be investigated over debt collection, says Mike Ashley

National Financial Awareness Day: Expert tips to take control of your money

Homeowner property repossessions in 47% annual jump but mortgage arrears falling

Is The Nick Woltemade To Bayern Munich Transfer Truly Dead?

When Violence Based On Religion Or Belief Amounts To International Crimes

Washington Freedom Hope To Have Home Cricket Ground By 2026

Tottenham ‘Can Play Against Any Team’, Says Frank After Super Cup

People Will Lose Their Minds When AI Such As Artificial General Intelligence Suffers Blackouts

Gatwick ‘optimistic’ minister will approve expansion plan

British Gas owner takes stake in Europe’s biggest LNG terminal in £1.5bn deal

Asian shares are mixed after days of gains driven by hopes for US rate cuts

New York sues Zelle, says security lapses led to $1 billion consumer fraud losses

Kellogg’s becomes first company to sign legally binding agreement removing toxic dyes from cereals

Powerball Jackpot Rises To $565 Million—Here’s What The Winner Could Take Home After Taxes

Major League Scouting Report On Toronto Blue Jays’ Trey Yesavage

Hidden Door Turns Fan Worlds Into Licensed, Revenue-Sharing Story Platforms

UK growth slows as economy feels effect of higher business costs

Outrage as bingo players 'win' share of &#163;1.6m - then Gala takes it back

Zara McDermott created ‘the best leggings of all time’ and they’re only £30

Pink Oyster card reader rule could save you money while travelling around London

Small firms turn to virtual employees to combat National Insurance

I paid next door's British Gas bill thanks to smart meter mistake: CRANE ON THE CASE

Thieves are targeting luxury Mercedes 4x4s to steal vulnerable part

How Reeves's inheritance tax changes will affect families

The eight popular EVs that never reach peak charging speeds... and the two that do

Number of unroadworthy cars on our roads has soared in the last year

Nick Train interview: These world-class UK companies are primed for profit and going cheap

Ethical hacker exposes how criminals access YOUR data with just an email address

7 takeaways from Taylor Swift's appearance on the 'New Heights' podcast

The godfather of AI has a tip for surviving the age of AI: Train it to act like your mom

Why every A-lister also has a side hustle

FTSE 100 Live 14 August: GDP growth above forecast, index seen higher after record close

What are student loans and when do you start repaying them after university?

AI Legal Developments Affecting Hollywood In 2025

Cyber Attacks Could Stifle Online Demand From The Under-35s

UFC 319 Fight Card: Date, Time, Location, How To Watch Or Stream

DVSA warns drivers to act immediately over MOT 'mistake'

DWP payment for people with reading issues could be worth £749

UK's cheapest theme parks ranked - one is free to enter this school holiday

Woman picks up £3.09 Too Good To Go bag from Spar and is blown away by contents

Found a yellow ticket on your car? Beware, it could be a new cruel parking scam...

Investing for beginners: The best platforms to get started as an investor

The cofounder of xAI is leaving the company. He says he's learned 2 main things from Elon Musk.

Taylor Swift says she was in a 'state of perpetual physical discomfort' while performing on the Eras Tour

Elon Musk says Google has the best shot at being the leader in AI

Researchers built a social network made of AI bots. They quickly formed cliques, amplified extremes, and let a tiny elite dominate.

Drake Baldwin Takes Charge Of National League’s Rookie Race

Potential Big Bash League Privatization Sparks Major Interest In The U.S.

B&M shoppers 'run' to stores for viral £35 'gorgeous' mirror

Yoga app for over 35s that helps with 'weight loss and heart health' is 61% off

'I saved £57k by age 26 - one simple system changed everything for me'

The Kremlin's recruiters are crushing their targets and might get their 2025 goals bumped up, Ukraine spy chief says

There are 25 artists who have been featured on a Taylor Swift song &mdash; here they all are

Projections: ‘Nobody 2’ Has No Chance Against ‘Weapons’ At Box Office

Taylor Swift And Travis Kelce On How They Deal With Internet Hate

Everything To Know About ‘The Life Of A Showgirl’—Release Date, Tracklist And More

Yadhira Carrillo’s TV Return In ‘Los Hilos Del Pasado,’ Premieres On Univision

Taylor Swift has been saving up to buy her music masters since she was a teenager

David Ellison's plan to rebuild Paramount: 'Top Gun 3' and more 'Star Trek'

Outrage as bingo players 'win' share of £1.6m - then Gala takes it back

There are 25 artists who have been featured on a Taylor Swift song — here they all are