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.