Don't waste a career crisis
Dear Gup and Dabbles,
Last week I had a call with a 25-year old kid (yes, I can call 20-somethings kids as a thirty-something dad) who decided to quit his job at a private equity firm, move back home with his parents, and buy a business.
He decided to quit because he was working non-stop and saw that his boss and his boss' boss also worked non-stop. He knew it would be intense when he joined the company but he felt it deeply when he had to work during his PTO while visiting his newborn nephew.
To make matters worse, despite a glowing performance review, the company passed him over for a promotion that he was implicitly promised.
The future payoff was not worth the grind, so he crashed his life and quit.
---
The first time I crashed my life was about six months after I graduated college. I had commissioned into the Navy and won a spot at BUD/s, the initial selection training for aspiring Navy SEALs.
It wasn't long before I realized I didn't fit in. I was below-average performance wise, I didn't relate to most of the officers there (and wouldn't choose to hang out with them), and most importantly, I was no longer excited by the prospect of becoming a Navy SEAL
I set a goal in high school of becoming a Navy SEAL, and took all necessary steps to get a spot in training. But between high school and the time I entered training, that desire had faded.
So I quit, and then six months later, I was out of the Navy entirely in the middle of the Great Recession.
Crash.
---
I asked Jake (the 25-year old) why he wanted to buy a business as his next career move.
He listed a few:
He wanted more autonomy and control over his destiny
He wanted to take the risk now while he was young and not thirty-something with a family
The potential to make a lot of money was appealing
He likes the idea of creating a great service experience for customers and wants to really make them happy
I thought these were all great reasons for buying a business, but just to be a bit of a provocateur, I asked:
"Have you ever considered moving to Thailand for a year and screwing around?"
---
The reason I asked this question is because after I separated from the Navy, I went to Cairo with your mom to teach English to have an adventure. I was newly under the influence of Tim Ferriss' Four Hour Work Week and wanted to live cheaply overseas and think of a "passive income business" I could start.
I made a complete 180 degree turn in life paths. Initially I was on track for a military career, and now I was on track to live a very strange unstructured, bohemian traveler lifestyle.
It would have been relatively easy to change course in a less dramatic fashion (say, a 30 degree course correction) by say, pushing harder to find a different military career path, maybe leaning into an intelligence officer career.
The 180 degree turn was valuable, but not because living overseas full time or starting a passive income business was the right path for me.
It was valuable because it gave me more information about myself. My self-identity had been built around pursuing this Navy SEAL goal and I destroyed that in under a year. Trying to pursue a different military career would have been a sort of compromise solution. I'd still be doing something masculine and patriotic inside a bureaucratic organization with a defined career path and sure I'd learn a few things about myself.
But I wouldn't have gotten so many insights into myself as I did hanging out with a bunch of American expats and wealthy western-education Egyptians and trying to start my own business.
I learned that I chafe under authority (wish I had known that before joining the military), I have a creative side, I default to laziness in the absence of work, and I appreciate developed western country comforts,
I learned that I'm actually not particularly money motivated. I like being contrarian. I learned that I was confusing wanting to be an entrepreneur with wanting to be known for my ideas and making money outside of a paycheck format.
I learned a lot, and I learned it on an accelerated timeline, because I did something so radically different from what I was initially doing. These lessons are still making a big impact on how I think about my career today, now that I'm a thirty-something with a family.
---
Jake was surprised by my question, and he responded, honestly, that no, he has never actually considered doing that.
And I don't think he will.
I think Jake will be just fine. Buying a business is definitely an adventure.
But it feels a little too close to what he was doing before in some ways.
It's still business and money driven to some degree. It's still analytical, and it's still a known and well trodden path that can be prestigious if it works out. I think it's a 30 degree correction, not a 180.
Jake will still learn a lot, but my hunch is that he'd learn a lot more about himself if he actually went to Thailand (or other cheap foreign land) and tried not having any goals for a while.
---
One of the best ways to learn who you really are and what you truly want is to experience something completely different from your default path [see
’s writing on this].Career crises, despite being painful, are uniquely valuable moments that make radical experimentation possible.
My advice to you, sweet daughters, is that if (or when!) you face a career crisis, don’t rush to simply fix it or get back on a known path.
Instead, ask yourself: "What is the most interesting, radically different thing I could try right now?" And then go do it.
Like Jake correctly assessed, this is the time in your life to take risks.
Just make sure you're taking enough risk to make it worth it.
Love,
Dad