The Perpetual Daydream of NYC in the Summer
and turning 30 means the next career step
NYC is…..
….a huge distraction.
It’s 7 nights a week of social activity. I’ve never been to a place where I have to actively plan out my alone time and never have to plan out socializing. On Monday I won’t have any plans for the weekend. And yet by Friday it’ll be too many things to go to.
And people are just down. One Friday, I planned for a small quiet dinner with two friends and the intention to be back home by 11pm. And of course by 3am we were singing karaoke with strangers-turned-friends.
So NYC feels like a perpetual daydream in the summer. The combination of the August heat along with a hazy perception influenced by booze and substances creates the feeling of a continuous dream. And in small moment throughout - I get a sense that this time is precious. It’ll never be like this again. So I try to cherish the moment.
Other times though - it feels like you’re being sucked around in a washing machine. Perpetually passing by different people and getting drained of social reserves.
Anyway - I’m planning on moving back to San Francisco soon.
Most people are surprised why anyone wants to go back there.
All the good people left for NYC already.
Parties are full of people not-drinking and going to bed at 10pm.
The city has turned into a Gotham city of homeless people shitting on the sidewalk.
Well there’s actually a similar amount of shit happening on the sidewalk between the two cities. But I’m ready to trade social abundance with a sunnier winter, good surf, and more opportunities to focus on startups.
Career Crossroads
I've been conditioned to segment my life into blocks of four years. High school. College. Early Twenties (22 to 26). And turning 30 means senior graduation for your late twenties.
I’m at career cross roads for what I want to do next. Here’s my short career recap:
22 to 26 - Gaining experience in tech.
Move to San Francisco for a marketing analyst job.
Break into data science after a few months and join a 10 person startup as the only data scientists.
Startup gets acquired and work changes
Move into senior data science role and join my first data science team.
Start a side project six months into my role.
26 to 30 - Learning how to build a startup
Quit my job two weeks after turning 26 to work on Interview Query full time
Grow business to $40K in monthly revenue after 1 year.
Slowmad travel across 3 years to 10+ different cities.
Scale out processes to hiring a small team and learning how to manage.
Deal with the tech downfall and the startup rollercoaster.
Begin outsourcing day to day operations to team members so the business can run on its own.
30 to 34 → ????
In this new career odyssey I’ve evaluated a few interesting paths. They’re all still about startups:
Venture Startup Founder: Find an idea that you’re passionate about with billions of dollars in market opportunity. Raise money and work on it for 4+ years minimum with an eye for scaling as fast as possible.
Bootstrapped HoldCo Operator: Repeat the bootstrapped playbook and buy / build businesses that grow to a similar size as Interview Query in half the time (2 years). Ideally own a large stake in 4 to 6 different businesses that generate free cash flow to continuously re-invest.
Bootstrap a Company to 10x the last one (8-figures in revenue): Buy a business or start one again and figure out what it takes to go from $1 million to $10 million in sales.
So far - I’ve started to learn into 2 or 3. The nice thing about bootstrapping various companies is that you can test a lot of ideas to see which ones stick. And ultimately if any of them have larger potential - then you can try to spend more time focusing on growth.
But you also don’t know how much to invest in everything. For example - I’m still working through slow progress on Yo! Focus. And it’s definitely from a lack of focus when bouncing around on different business ideas.
Either way - I want the next four years to be a step change.
It’s like the time I climbed piles of boulders in Joshua Tree. Each subsequent pile of boulders we climbed ending up dwarfing the last. Finally on my last hike I could barely see that first pile of rocks from the peak.
Eight years ago I just wanted a 6 figure data science job. Four years ago I was wishing for $10K/month from my own project. Now I’m squinting at full-time jobs and looking up at more startups to come. And I think it can still be done while getting some good surf in.
Other Finds
I was referred this app Dimensional by a friend. It’s branded as a social personality test app. It’s coolest feature is definitely seeing your compatibility across friends. Nice data visualizations. Here’s my profile if ya’ll wanna compare.