Lessons Learned
Lots of humble brags from founders listing how much money they made or raised in 2021. Not my style. I wanted to share my actual reflections from my journal on what I learned in 2021.
It’s not pretty — but it’s real. Three simple lessons:
I worked harder this year than I ever have in my life.
12–14 hours a day (meaning, no breaks between waking up and going to sleep). Often 6–7 days a week. For 6 months straight.
I never knew I could work as hard or long as I did.
1) I love my job. I enjoy the work, our team is stellar, and our impact on our users and the world is meaningful.
But I learned professional success doesn’t feel sweet if there’s no balance.
Despite the work, I allocated a lot of time to doing the things I loved by simply moving closer to them.
Montana and Dolomites for biking. Hawaii for Surfing. Colorado and Utah for skiing.
Thank god for remote work.
2) Just as I was working harder than ever, key people I counted on for support left my orbit this year.
Two cofounders. My closest advisor. Several valued team members.
I waited to find a great team before I started Almanac, and losing partners was, legit, my greatest fear.
So for many of these people, I bent over backwards to keep them in the company longer. Helped do their jobs. Moved things around. Reduced their work.
But that didn’t change the outcome.
I’ve realized covering for people is a form of ruinous empathy.
Now being on the other side of my greatest fear — and thriving — I feel liberated.
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I’ve resolved to have higher expectations, communicate them, and enforce them when things aren’t working.
It’s up or out.
3) I traveled 200k miles last year. I spent more than 2000 hours in meetings, with thousands of people.
I don’t remember most of it.
What stands out are special moments of deep connections with my people.
Drinking airline-sized bottles of vodka with my friends in Hawaii.
Staying out until sunrise dancing with friends in Miami.
Doing a naked ski run in the Aspen wilderness.
Catching up with lifelong friends around the world, and spending time with my family in NYC.
I’ve realized (yet again) that work is not about winning.
After a baseline amount, no amount of money or success makes you happier.
My happiness, and identity, come from the people who shape me into who I am.
My intentions moving forward:
1) Prioritize friends and fitness. Nothing else will be good if you don’t.
2) Set expectations and enforce accountability. You only hurt yourself if you don’t.
3) Deepen relationships with those you’ve known the longest & who have been there for you.
And most of all, keep moving fast and making the most of each moment.
Life is short, and time is valuable because it’s limited.
Don’t waste it.
