Lenny Rachitsky

Lenny writes a weekly newsletter about product and growth, angel invests, and occasionally advises companies. Before this, Lenny worked as a PM Lead at Airbnb, started a company called Localmind, and before switching into PM was an engineer. Headshot by Marc Reisen.

On his morning routine.

Most days I’m up around 7.

It’s hard for me to define an “ideal morning” because I really struggle between enjoying it and taking it slow, and being productive as quickly as possible.

Every day, I can either wake up and start working, or take it easy, have a cup of tea with my wife, and take my dog out for a walk before booting up my Mac. 

Since I’m working for myself these days, I actually try to do the former as much as possible.

To not take for granted the flexibility I have in my life right now.

Then, before I dive in, I generally try to list out the things I want to get done that day (e.g. finish this post, send that email, etc.) and throw that into my todo app.

On his optimal workflow.

One change that I recently made, and strongly recommend, is completely blocking off the first half of the day for deep work (e.g. writing).

I take zero meetings and calls until at least after lunch.

As a result, the first half of my day is dedicated solely to creating, and doing what I want to do, vs. what I need to do.

I have also become reliant on an app called Centered.app, which is a mindfulness oriented to-do list that uses specially designed music to prime your brain for concentration. I quickly realized that I can’t work listening to regular music, like classical or anything with words, so this has been super helpful. 

Lastly, I turn off notifications on my computer (turning on the hidden Do Not Disturb feature on OS X), to avoid distractions that I know will suck me in.

On days that I need the most concentration, I’ll also grab a Magic Mind shot to really zone in and get stuff done.

On his writing process.

For my newsletter, I basically write an advice column about product, growth, and anything else that stresses you out at the office. People send me questions and I answer them to the best of my ability.

I work on a number of new posts at once and maintain a workspace in Coda where I plan out the next 4 to 6 weeks of content.

For each week, I’ll choose what questions I want to answer, create a page in Coda for each of those topics, and then start dumping notes and thoughts into each page.

I typically work until my brain simply can’t look at the page anymore, and then I get up, walk the dog, talk to my wife, and scroll through socials.

This digital workspace acts as a repository of ideas I’m exploring and that I want to write about. Twitter also helps me to develop ideas, both for idea generation and research. I can now just tweet out a question and get a ton of different perspectives super quickly.

While Twitter is great because I can get answers to questions I have, and get connected to incredible people, it’s also an endless suck on writing time. I try my best to moderate how much time I spend there, but I generally lose the battle.

More importantly, it’s become harder to tell whether Twitter makes me happier and more productive as a person. But I still can’t resist.

On his drive and ambition.

I think part of my hustle and ambition comes from when I was younger. I was a super shy kid, extremely independent, and kept to myself most of the time. 

Deep down, I knew that I could do a lot, but I was always seen as this anti-social nerdy dude even in high school.

Despite that, I always held onto this goal where I would eventually start my own company and show people I was capable of big things. 

My drive also comes from the fact that my family emigrated from the USSR and that we didn’t have much of anything when we came over.

My parents essentially lived the American dream (both of them have their own businesses now), and I’ve always been inspired by their hard work and ambition.

On chasing happiness. 

I left Airbnb a year ago and I gave myself 6 months to figure out what I wanted to do. On a macro level, my strategy was simple: spend more time on things that give me energy and less time on things that don’t. 

I quickly figured out that I really enjoyed writing, something that quite frankly I never did before, nor expected to want to do.

I thought I was going to start a company.

This time off helped me realize that I actually don’t want to start a company yet, or become VC, or write a book (all things people kept suggesting I do).

It’s actually been really helpful to recognize the things I don’t want to do, I call them my anti-Goals.

In tandem with discovering my pull for writing, I found that I thoroughly enjoyed angel investing as well. So I’m trying to craft my life to revolve around my newsletter (for income), angel investing (for upside), and advising companies here and there (to stay grounded in real problems).

On his evening routine.

This sounds weird, but at night I usually snack on chips and salsa (I’m addicted), along with some Rooibos tea and sometimes a glass of wine.

Then I usually watch some TV, most recently Billions and Man in the High Castle, which helps me decompress.

Once I’m done with the workday, I generally don’t want to do anything that uses my brain. I don’t journal. I don’t exercise at night.

I just relax before knocking out around 11 and 11.30.