I Just Waved Goodbye to a $90k Salary

Joe Hassett
Decaf Destinations
Published in
4 min readDec 18, 2018
Photo by Pascal Renet

Three years ago, I thought I could predict my future. At 24 years old, I was living with my girlfriend in a high rise in Chicago’s Gold Coast neighborhood, three blocks west of Michigan Avenue. I was working for a top consulting firm in systems implementation and making $60k/year.

On Mondays I would wake up at 4am, take the elevator down to the lobby and hop in a cab to Midway airport. On the drive over I would marvel at how beautiful the city was when it slept, which was always my favorite part of the week. I would be eager to see if the status I had accumulated via hundreds of stays at hotels would net me a suite upgrade. Once, while traveling to Madison, Wisconsin, I was upgraded to a presidential suite that Obama had used a month prior. Not too shabby for a kid two years removed from college, right? But man, I hated my life.

Photo by Mike Wojan

Ask 24 year old me where he’d be in three years, he would have said married. A homeowner. Have a dog and be on his way to gifting his parents a grandchild.

At 25, I bitch slapped that life trajectory across the face. I needed a change, so when my job offered me the chance to move to San Francisco, I took it. I moved into a two bedroom apartment with three other dudes (we curtained off the den and living room, classic SF). I learned how to use the word “hella”, not to call the city “San Fran”, and then waited patiently for a job at a startup to fall in my lap.

My dream was to eventually land a gig at Airbnb, I longed for the cafeteria access and annual $2,000 travel stipend. I spent hours perfecting my resume and cover letter. I triple checked everything on the application and with a dollop of misguided confidence hit submit. Less than twenty minutes later I received a rejection letter. Thankfully the other 50 or so rejections I received from various startups across the Bay cushioned my fall. I promised myself I would not leave San Francisco until I broke bread in an Airbnb dining hall. When my straight up boss of a friend got hired there, I used him for my own nefarious purposes. I had a big dumb grin on my face as I was scooping orange chicken onto my plate at the hot bar.

When my family would ask how I was spending my time, I would say I was attending meetups (I went to exactly one), teaching myself to code (lol no), and going on a bunch of dates (I took all my hinge dates to the same brewery two blocks down from my apartment, and in all honesty would have preferred staying home and watching Parks and Rec).

On Sundays, during the opening credits of a fourth consecutive episode of Parks and Rec, I would reprimand myself for not spending my time more productively. Ultimately, I decided to move back to my hometown of Atlanta. The notion that the city I lived in had anything to do with my failures was admittedly a silly one, the real culprit being that my effort was about as consistent and present as an alcoholic stepdad. That said, the change of scenery has benefitted me.

Now, at 27, I’m currently living with my parents, and I am as single as the last slice of bread. Pretty lame for a kid five years out of college, right? But man, I am loving life. Three weeks ago I quit my job and the $90k salary that came with it. I have started a location independent business and in two weeks I am moving to Colombia for a couple months. Millennial alert!

Photo by Helena Lopes

My parents are understandably concerned. They are risk averse, and whether by nature or nurture, some of that risk aversion resides in me as well. But when my dad asked why I couldn’t keep my job (and the guaranteed salary, health insurance, and 401k that came with it), and slowly build my business on the side, my response was simple. No more excuses, no more pretending.

“Because dad, in order to do something special, you have to do it.”

I know, not the most profound saying, so I will let Ron Swanson explain;

“Never half ass two things, whole ass one thing.”

As I look over my shoulder at the past and catalogue all the things I never accomplished, I realize I never actually tried. Ask me how I spend my time now, I would say I am building my business (landed our third project yesterday), prepping my Spanish for Colombia (65 day streak on Duolingo!), and teaching myself Adobe CC (drew a pixel art version of my friend in Photoshop. He loved it).

Not sure I want to take credit for this

I have not watched an episode of Parks and Rec since I left San Francisco.

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