Is Taking August Off Indulgent, or Finally Sensible?

I used to think August was such a weird, almost fake month – one that was indulgent, but mostly unproductive. I thought about this as I was on a Citibike yesterday along the West Side bike path which was way emptier than usual.

Everyone takes it down a gear I always figure, and maybe if I worked a *bit* harder, I’d have the advantage.

So I brought gelato into the office to keep everyone cool, and just cause well, its August!

The more I talk to folks about how they’re working this month, the more answers I get. WFH month for some. Lots of travel for others. Many Hamptonites have been out there since Memorial Day. And for a lot of people, honestly, August changes nothing. Same commute, same inbox, just with 98% humidity.

But this is one of those years I keep hearing the same refrain from founders and investors : “I could use a few weeks to clear my head.” The last I remember this was right after Covid, people felt similarly.

This year has felt like one long sprint: the crazy news, the pace of rounds, keeping up with whatever new AI model or company launched. Nobody really got a lap to catch their breath.

Maybe August isn’t the least important month, maybe its the most.

I used to think going “out east” or upstate or anywhere else for part of the summer was indulgent and what bankers do, not what hard-core, ambitious tech folks would do. Or maybe I’m just getting soft?

I heard about a founder hosting an actual scavenger hunt out in the Hamptons and I’ve been invited to work events out there and elsewhere outside the city. Maybe this new normal is the new normal.

But a small part of me isn’t totally comfortable with “relax” mode.