I’ve been working on a fully distributed/remote basis since leaving a big company in ‘07. I’ve never actually met our back office/CFO equivalent, nor have I ever been in the same room as our corporate lawyers or investment bankers.
When @ABCSharkTank filmed my opening sequence, they wanted to highlight the Lowercase HQ. Well, we’ve never had one. So, the producers faked it by borrowing a @Heavybit breakout room and put our logo on the monitor.
There is a lot of upside to not going into the office. We are closer as a family and the time I don’t spend commuting can be spent outside. That said, my kids being around while I’m negotiating on the phone has led them to adopt some “colorful” language. Whoops.
No doubt being remote does require some extra effort to stay in touch with the team and others. What’s worked for us is inviting collaborators to where we live to spend high quality time vs casual catch-ups in passing.
Calendaring a 1:1 slot in a conference room in Building 87 is cool and all, but going on a hike, cooking dinner together, and staying up late to share big ideas is hard to beat for building meaningful relationships.
We left SF 12 years ago. It didn’t make sense back then. Our work was in the Bay Area, and we were far away. But we’ve never regretted it. Our business likely would’ve done better if we were downtown. Yet we’ve never been happier nor healthier. Hard to think of what matters more.
Some people thrive in offices and cities. Some live for the watercooler. I don’t, and maybe you don’t either. If I don’t get time alone outside everyday, then I’m not effective at my job and my head and my body are a mess. Maybe that sounds familiar to you.
So if you’re lucky enough to have the opportunity to work from home and moving somewhere more livable, give it some real thought. If you’re leading a company, stay open to the idea of a distributed team. If you’re an investor in office space, sell.
Of course WFH doesn’t work for everyone. Spare me the classic Twitter moaning about how this approach isn’t universally accessible for x, y, and z reasons. No shit. But this is what worked for us and many others, and I’m sharing it because it might work for you.
Last, I see a lot of people saying they’ll move to a place with a better life “someday.” A couple years ago, a few hundred of us on here lost one of our best friends, @tedr. He was 45 and his passing certainly wasn’t in anyone’s plans.
He was legendary for enjoying every single day of his life. When he first found out he was sick, we all rushed to help check off some bucket list items for him. But he calmly replied, “I don’t have any. I’ve been living my bucket list in real time.” Hashtag goals.
In parallel, Warren Miller, a filmmaker/author who deeply influenced my journey passed away. He had a famous saying that I live by, “If you don’t do it this year, you’ll be one year older when you do.” Preach. Scary as it might be, maybe now is the time to make your move.
Change is frightening and the timing will never be perfect. Yet there are good odds that, for some of you, leaving the big city and the office building behind will leave you happier, healthier, and fulfilled.

Good luck and keep us posted! 🙏🏼
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