172: Professional Courage

Hope you are doing well and staying dry. I got 3 emergency flash flood alerts on my phone on Friday as the Northeast got slammed with buckets of water.

Fortunately I was able to make it out of my neighborhood and make my flight to SFO. I was gifted with an entire row of seats all to myself, which is like better than being in first class. This good fortunate was short-lived as we had a bit of scare on the landing. Jason Calacanis was apparently on my flight and live-tweeted the whole thing.

Today we're continuing the series on risk and courage.

If you're just catching up, my previous pieces were about acts of physical courage (a gymnastics skill) and emotional courage (asking out my future wife) in the face of great risk.

This letter is about how I found the courage to take my greatest professional risk: leaving Meta, go on a sabbatical, and coach full-time.

In the United States, people tend to celebrate when you quit jobs to chase your dreams, much to the chagrin of my immigrant parents. But I think it makes sense because this country was about a bunch of rebels sticking it to The Man (ie King George III), and people recognize that quitting your job is a "same energy" kind of move.

But quitting and starting over in something new gets harder and harder as you get older. At 37 years old, I'm closer to 50 than my college graduation and while still filled with energy and aspirations, I feel the groping hands of age and lifestyle creep affecting this decision.

On March 22nd, 2023, exactly two months before I gave notice at Meta, I jotted down a few notes for an article that I don't think I ever wrote:

As you get older it feels harder to gain conviction for your actions

Young: impulsive
Getting married
Changing jobs
Moving cities

You know less
You have less to lose
You have more time / energy

Older: Know more
More to lose
Less time / energy

In the Badge Post video I shared about leaving Meta [#155] , I said that it had been "over ten years since I had quit my job to start a company", which referred to May 2011, when my cofounders and I got a Y Combinator interview and I just up and quit my startup job.

The CEO / Founder of that startup, my boss, was pissed at this decision because

1. I didn't even wait to see if I was going to be accepted (making me a cocky motherf***er) and
2. I had worked at the company for 11 months and was effectively spurning the opportunity to vest any stock (a vote of no confidence in the startup).

Despite making effectively the right choice (we did get into YC, my boss's startup exited for a very modest sum after many years) that Act of Quitting definitely had young person's"F*** This" energy.

My Act of Quitting at Meta had a very different kind of energy.

I discussed my decision with my direct manager and skip manager ahead of time and listened politely to their half-hearted attempts to get me to stay. I timed the exit around a stock vest and benefits getting paid out. I left behind a folder of key documents for the next PM.

This time I did not have a Y Combinator or some other thrilling and prestigious opportunity lined up.

I was going to do some wandering and exploring in a sabbatical, spending down the savings I had accumulated over 3 years of finally earning a top tier tech salary, then figure out this solopreneurship thing. My sabbatical is now over and I've been "back to work" to for a few weeks now.

On the day I gave notice (also my birthday), someone I knew announced on Twitter that he was not able to sustain himself as a solopreneur / coach and was job hunting.

That was an eye-pener. I had paid for his Maven course on Career Storytelling (which was great!) so it was definitely shocking to see him essentially wave the white flag.

The possibility of failure was very real.

And the cost of failure is higher than it has ever been. I have a mortgage. I'm trying to grow my family. The tech job market is not super hot at the moment.

I would be lying if I didn't wince every time I look at my bank account. And I would very much not like to fail, not have to announce that I'm looking for a job sometime next year because I could make it work.

Unlike my last two stories, I don't have a simple wrap up to this story, where I announce that I'm already making more than my Meta salary as an executive coach. Though that is absolutely one of the milestones I have in mind.

I may not have the desired outcomes yet, but I feel good about my inputs:

• requesting referrals for new clients
• writing my book on startup pivots
• recording guest podcast interviews
• promoting my workshop, updating my website
• posting videos and threads on topics I find fascinating
• Even hiring a full-time assistant to support my work

In other words, I have momentum that's aligned with my skills and my interests, as discussed in the Flywheels issue [#166]. And yet I feel uncertainty.  just like you probably do for whatever it is you're trying to do. Let us walk through the neutral zone, the fog of war, the dark forest, together as comrades.

My sabbatical and this career shift I'm making is the biggest professional risk of my career. And I'm proud of myself for taking it. Because as discussed in our last letter, there are no guarantees [#170] except that we will all one day be shuffle off this mortal coil. And that keeps me from letting the fear paralyze me.

Take care and talk next week,

—Jason

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