This is my friends & family newsletter. I publish here for reference and sharing. You can subscribe here.
⏩️ Updates
I’m now on TikTok! Big thanks to my friend Aakash for the push. It’s more fun than I thought it’d be. You can follow me here.
The next cohort of the Land A Remote Job program starts October 5th. It’s group coaching for ambitious professionals looking to land their next remote role. Past clients have landed jobs at meta, hims & hers, Samsung, Harry’s, and more. Learn more here.
ICYMI, last month I published:
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My three-step playbook to prepare for interviews
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When do you start looking for a new job? (and more burning questions)
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Annabel’s 4th birthday letter
What’s new with you? I’d love to hear about it. Hit “reply” or DM me here.
✂️ Not Made To Play The Son
This newsletter was supposed to be a victory lap.
See, I thought I had my next job lined up. I was already drafting a case study (ha!) showing how to use my interview prep strategies.
It was supposed to be a seamless transition from paternity leave to my next remote job.
I was 90% confident I’d get the offer.
But I did not.
Horse meets cart.
Let’s talk about what’s next.
⚙️ The process you control
I ran a post-mortem on not getting the role. The TL;DR:
I ran a good process. I started with a warm introduction, got a referral, had people back door recommend me, and took my interview prep seriously. But I stumbled in a couple of interviews. Now, I know where I can adjust.
The process is the only thing you control. You don’t always get the desired outcome. That’s the game.
I’m wearing my stoic hat right now. But to be very clear: I was surprised and disappointed. It was a great role. I would have been great it in.
But I’m lucky. I’ve been passed on before. What I’ve learned is:
No doesn’t mean never. It just means not now.
🧧 Crisis meets opportunity
“Never waste an opportunity offered by a good crisis.”
Niccolo Machiavelli said it first. He’s best known for being featured in Taylor Swift’s song, Mastermind (joke) (half).
I did what one does after a rejection: I started taking more interviews. Halfway into the process, I realized: I had zero enthusiasm for joining another company.
So I paused all my job search efforts and dug into “why?”
I landed on three reasons:
1/ I have a 6 year goal in mind (outdated now but directionally correct).
Is jumping straight back into a w2 the best way to achieve that 6 year goal?
Or instead, could I focus on the side hustle… and find consulting jobs to meet my monthly nut for now?
2/ All paths lead to this.
Taking another w2 now only delayed the inevitable.
All paths lead to me working on this side hustle or working myself. The only question is “When is the best time?”
3/ The climb up a corporate ladder never interested me.
I never wanted to manage people, much to the chagrin of my managers.
I didn’t want that path, clamoring from a Senior IC to a Director to VP to C-Suite aka professional liar.
This reminds me of a quote from The Wire:
“I wasn’t made to play the son.”
In a nutshell: Do I accept uncertainty today for more money and freedom tomorrow?
Not getting this job might be the push I needed.
Crisis meets opportunity.
⏳ No best time
The more I’ve stewed on this, the better I feel.
This isn’t optimism. It’s pragmatism, with a firm grip on reality:
1/ We have insurance.
This is the first question my friends have been asking.
And rightfully so. When your insurance is tied to employment, your mind thinks of all the cataclysmic events you’re now bound to endure once that COBRA runs out. Fortunately, we can get this through Amy’s employer and check that box.
2/ There is no best time.
But this time is as good as it gets.
We’re settled in Philly for a while, and I don’t even want to think of moving house for at least 2-3 years. The kids are in school. We have a 4-month-old but to be honest, after the second kid, the marginal amount of work is negligible. Parenting feels the same, you’ve just got this baby in your arms while you’re doing all the things.
Now is the time to take on additional volatility in exchange for future upside.
3/ The immigrant mentality.
I talked about this more here.
We saved money. We rent, so our cash isn’t locked into a property. We pay cash when we buy cars and don’t carry over credit card debt. Plus, during COVID, I started building cashflow projects, so we could calculate our cashflow for 12 months with about 90% confidence.
4/ This is a 2-way door.
I can always find a w2 later.
5/ I’ve test-run this during COVID.
6/ I’ve been testing the Remote Work business.
I’m a year into this experiment.
It’s a fledgling business, not even ramen profitable yet. I think there’s a there there — maybe not in this exact iteration, but close. And I have the tools to chase it down.
⚔️ This is the quest
Not the goal. As David points out, the distinction is critical:
“You expect a quest to take you into a new and unfamiliar landscape. You expect there to be puzzles, surprises, perils, and curious encounters. A bridge you counted on will be out. You’ll meet an interesting stranger on the path. You’ll hear wolves howling at night.”
The challenge is the fun.
Thanks for reading.
