How We Slacked Off in Our 20s & Still Retired in Our Early 40s

What type of person were you when you graduated from college and became a young adult?  Were you a “Go-Getter” or a “Slacker?”

Go-Getters know what they want in life, and they don’t waste any time going for it.  They move straight from high school to college, and then right into their chosen career path.

Slackers, on the other hand, take awhile to figure out their life path.  Sometimes a long while, like years or even decades (or for some, perhaps never).

My wife, Allison, and I fell into this camp.  We both went to college right after high school and tried to get “real jobs” when we graduated.  But we realized we weren’t ready for a serious career path that early in life.

We totally slacked off in our 20s, but it was a lot of fun and it led to our future path.  We eventually got on track with careers and finances in our 30s, which ultimately brought us to early retirement in our 40s!

So even if you slacked off in your 20s like we did, you still have time to turn it around and achieve FIRE (Financial Independence / Retiring Early).

Here’s how our journey down Slacker Street in our 20s eventually ended up on the FIRE Freeway in our 40s:

Our 20s:  Restaurants, Acting, & the Internet

Age 22:  Selling Cleaning Products

My first job out of college was selling industrial maintenance products.   My boss made the job look easy. I just didn’t have the knack for selling cleaning fluid, bug sprays, and bathroom deodorizers.  I stuck it out for about six months, but I knew this job wasn’t for me.

Age 22 - 24:  Restaurants, NYC, & Strip Clubs

I thought I’d try my hand in the restaurant industry.  It seemed like a fun way to make decent cash in the short term.  I started at a Mexican restaurant and then upgraded to a fancier Italian restaurant.  

But as time went by, I realized that I was spinning my wheels in Columbus.  After narrowly avoiding a DUI one night, I decided it was time to leave Columbus for the Big Apple.

NYC:  I moved in with my dad, who was the super of a building in Manhattan.  I helped around the building and paid some rent in exchange for living in the big city.

My first job in NYC was as a barback at a “gentlemen’s club” in Midtown.  As you could imagine, this was a pretty fun gig for a young, single guy from the Midwest.  But after awhile, I got numb to seeing bare breasts and thong bikinis (Editor’s note: Thank God).

I segued into bartending at a small local bar, frequented by European tourists and middle-aged gay guys.  It was a decent job, but it was lonely (I was the only one working during my shift) and the money wasn’t great.  

I wanted a job in a big fun restaurant where I’d make good money, meet new people, and soak up all the NYC energy...

Age 24 - 26:  The All-Star, The Tender-Nob, & The Murder

Allison and I started working at The All-Star Cafe, a sports-themed restaurant in Time Square, along with over 100 food servers and staff.   

Allison got to the All-Star in a similar fashion to my path.  She graduated from Dartmouth, and then tried to get a “real job” as a teacher in Boston.  She realized she didn’t like teaching or living in Boston (the low pay, the weather, the crazy “Single White Female” roommate) and decided to move back to her hometown of NYC.

We started hanging out together at a local bar after work with some other workers, and pretty soon we were dating.  Six months later, we decided to visit San Francisco, and we never moved back...

Tender-Nob:  We got a studio apartment in an area that some people call the Tender-Nob, the zone between swanky Nob Hill and downtrodden Tenderloin.  

Our first jobs were in the restaurant business.  I landed a server job at a nice seafood restaurant along the waterfront.  Allison got a job at a diner, as a favor to our new landlord, who also worked there and needed someone to take some of her shifts.  

About two months into this job, one of the short order cooks fatally shot a waitress after an argument over poached eggs, which weren’t on the menu (Editor’s note: to this day, I don’t like poached eggs).  It made the national news. Time for Allison to find a new job.

Age 26 - 28:  Admin Jobs, Acting, & The Internet

We were both getting tired of working on our feet all day.  The idea of a desk job seemed very alluring, especially if we could get one with a decent salary and benefits.

Allison got a job as an Admin Assistant at a small law firm, and I got a job as a Customer Support agent at a credit card company.  Neither job was all that interesting, but they would become stepping stones to better jobs.

The Acting Bug:  I had taken an acting class in NYC and got bitten by the acting bug.  I landed some small parts in SF, in local theatre, extra roles in a couple of Robin Williams movies, and a lead role in an Independent horror film called Prey. (Check out my Oscar-snubbed role, it’s on Youtube).

I soon realized that becoming a professional actor was probably not going to happen.  I’d have to move down to LA and really dedicate myself to it, going through all the trials and tribulations of starving actors and artists. The Acting Bug’s bite wasn’t that powerful...

The Internet:  Fortunately, it was around that time that a former boss started working at a new Internet startup.  I didn’t know anything about the Internet or startups, but it sounded intriguing. I would still be doing Customer Support, but something was telling me this was a good move.

Simultaneously, Allison got a job at Andersen Consulting (later Accenture) as an AA.  Since she was super bright and hard-working (Editor’s note: I did NOT write this sentence ;-)), she was one of the few that was able to transition from an admin role into a consulting role.  

Age 28 - 29:  Real Jobs & Real Estate

At the end of our 20s, we finally started to settle down and get serious about our financial future.

Real jobs:  While Allison was at Accenture, getting experience working for several big clients, I got my next Internet job.  This time as a Marketing Manager, which was right in my wheelhouse.

Unfortunately, Reel.com became one of the first casualties of the dot-com bust, getting shuttered in 2000.  The good news was that many other Internet companies were still booming, so I got an even better job with a much higher salary (Ebates.com, which is still around to this day).

Real Estate:  We also bought our first home in 1999, a one-bedroom condo in the Oakland Hills for only $186,000.  This was our first real estate “investment.”

After only a year in our new condo, we decided to make an even bigger move.  We sold our condo and bought a “cozy” house in an old blue collar San Francisco neighborhood.  

We were making all kinds of moves with jobs, condos, and houses.  I even bought a motorcycle for my commute. Things were starting to look up, but this was only the beginning of our journey to FIRE.  We stepped everything up in our 30s. Here’s what we did...

Our 30s:  Marriage, Investing, & Side Gig

Age 30 - 33:  Wedding, Investing, & Nob Hill

Allison and I tied the knot at City Hall in SF in 2001.  True to our frugal ways, it was a small wedding, but we saved a lot of money and were able to share it with our closest friends and family.

Investing:  After getting married, we started getting further into our careers.  Allison was a Technical Project Manager with eBay, and I became the Director of Marketing at site called Tickle, whose speciality was an online IQ test..

This was when we first really started investing in the stock market.  It was easy to do with our company 401(k) plans, which we both maxed out, and eBay’s ESPP program.  Since we were making decent salaries, we actually had extra money to invest, so we also maxed out our IRA contributions as well.

We didn’t know exactly what we were doing with our investments, but we knew we just needed to start somewhere.  We understood the power of Compounding.  I’m sure I read about it in a book, and Allison learned it growing up in a financially-minded household.

More Real Estate:  We got tired of living on the outskirts of the city, so we sold our little old house and bought a condo in Nob Hill (the actual Nob Hill), right on SF’s iconic California St cable car line.

Age 33 - 37:  The Side Gig, Brain Games, & Tenants

DR Marketing:  I always loved the idea of small businesses that you could run “on the side” with a more passive income.  In 2004 I stumbled upon a business idea involving Google Adwords and affiliate marketing.

Little did I know at the time, but this side gig would end up generating a mid-six figure income over the next several years.  Simply called DR Marketing , it became what amounted to a 3rd income stream for us.  We wisely plowed these profits into a SEP-IRA and additional taxable accounts.

Startup City:  By 2008, Allison and I were in new jobs again.  She moved from eBay to StubHub, a startup company that eBay bought that was located in SF (no more 2.5 hour commute!).  And I became the VP of Marketing for a startup called Lumosity, which sold online brain games.

Even more Real Estate:  We sold our condo in Nob Hill for a huge loft in the Mission district in 2004.  Our friends joked that they wrote our address in pencil. In 2006, we sold the loft and bought a 3-unit house in the Castro district.  We planned to live in one unit and rent out the other two. Apparently we had stumbled on “house-hacking” before it was even a thing; we were #TrendSetters.

Between our side business and our rental units, we were making good money and investing quite a bit of it.  We knew we wanted to retire early (by the grand old age of 55), so we were exploring options before they were in the mainstream.

Age 37 - 39:  Pneumonia & Losing Half our Net Worth

Near Death Experience:  In late 2008, I had a near death experience from a severe case of pneumonia.  I was in the hospital for two weeks and ICU for much of that time.

The doctors never figured out how I got pneumonia.  Maybe it was the stresses of working too hard, being landlords, having huge mortgage and tax bills, etc.  Whatever it was, it ended up being a blessing in disguise.

That experience opened both our eyes to the fact that life is short and we needed to make the most of it.  We subconsciously made the decision during that time to find a way to become financially independent and retire even earlier.

Surviving the 2008 Crash:  The global economy suffered a major downtown in 2008. Our investments, both in our 401(k) and non-retirement accounts, took a huge hit (about 50%, although to be honest, we don’t know the exact amount because it was too scary at the time to keep track).  

Just before the crash, we had realized that being landlords was too much work, so we decided to sell our house and just buy a brand new condo in Mission Bay. However, in a massive stroke of bad luck, we didn’t sell our house before we closed on the condo, and as a result, we ended up as the proud owners of FOUR units in SF.  

Our property tax bill alone was over $30k per year for the two properties.   Lucky for us, our tenants remained employed and were able to pay their rent, which meant that we were able to pay our mortgages and keep ourselves afloat.

Our 40s:  GeoArb, Sabbatical, & FIRE

Age 40 -43:  Winding down & Letting go

Final laps: As we entered our 40s, we felt like it was time to simplify our lives. The first step was whittling down our RE holdings. Eventually the real estate market recovered, and we were finally able to sell the Castro house (net profit: $0; experience: priceless), which meant we no longer were landlords. We moved back to our Mission Bay condo and kept our nose to the grindstone in our tech jobs.

In Silicon Valley (& San Francisco), you become a bit of a dinosaur after the age of 40.   Tech startups are the domain of 20s and 30s “kids” with a few random grey-hairs who manage to keep hanging on.

Allison and I bounced around to a few more random startups during this time, but they all had issues: either bad products, bad bosses, bad cultures, or combinations of all these. We kept contributing to our retirement accounts, and our investments began to slowly recover.

We were actually thrilled when we both got laid off at the beginning of 2014.  It meant we could finally take a break from the rat race and enjoy life for a bit.  At the time, we thought we would do some traveling for a few months and eventually find another job, but….

Geographic Arbitrage:  In what would be our final major financial move, we realized we could significantly reduce our mortgage and cost of living by moving 10 miles away to Oakland.  In 2013, we found a condo with roughly the same square footage and floor plan, and with many additional amenities, for literally half the price of our SF apartment!

Age 43 - Present:  Enjoying FIRE!

In the years since retiring, our lives have never been more interesting, fulfilling, or joyous.  We travel around the world, we work on projects like Retire By 45, we’re involved in our community, we work out everyday; the list goes on and on.

I hope our story and our journey inspires you to achieve FIRE for yourself.  Life is far too short to be stuck in commuter traffic, dealing with angry bosses, doing mindless work, and being buried under mounds of debt.

It’s never too late to make some simple changes needed to get out of that situation.  You just have to take it one step at a time. If you slacked off in your 20s like we did, then you can make your 30s your decade to spring you into FIRE for your 40s and beyond! Even if you’re in your 30s/40s/50s, don’t give up! Shaving off a couple of years from a more traditional retirement age can be rewarding and worth the effort.