Two Weeks Offline: Confronting the Guilt of Not Working

Earlier this year, I took two weeks to disconnect on vacation. I put up away messages and removed apps from my phone.

I successfully stopped. But that wasn't always so easy for me.

When I was running my own nonprofit, I had the flexibility I loved, but I had a really hard time stepping fully away from work. I felt this guilt that if I wasn't being productive, if I wasn't doing something, then I wasn't working hard enough. I wouldn't deserve any success or get the chance to go further. Even on actual vacations, I held onto that sense of responsibility.

Back in early 2016, I took a trip to the Philippines with my husband and some friends. I was surrounded by some of the most beautiful scenes I’d ever seen - palm trees, white sand, jungle, scuba diving, and I remember that I spent a lot of time looking for wifi. I held myself to deliverables and goals even though I was the only one looking.

Funnily enough, when I worked in corporate, I didn’t have this issue. I was excellent at not checking my email on vacation, but I watched many of my colleagues succumb to pressure and patterns that make it hard to fully disconnect.

But then when I went back to entrepreneurship, I felt myself swing back to my pre-corporate habits. The same stress to be always on. The familiar what-ifs and need to check boxes.

But this time, I caught myself before I spent another vacation refreshing my inbox.

I planned my birthday trip and wanted to make it a real vacation. I told people I was going offline. I posted about it to hold myself accountable. I deleted social media apps off my phone. I only accidentally opened my business email once, but when I saw "so-and-so has commented on your LinkedIn post," I realized I was in the wrong place and shut it immediately.

I caught myself wondering whether my vacation itself would be a different kind of “productive" - epiphanies about my business or some stroke of life-changing inspiration while I stared at turquoise water.

But that didn't happen.

And that’s ok. I did actually stop, and that was my only goal.

I spent time at a family-friendly ashram for yoga and breathwork. I celebrated my birthday. I picked up sea glass and shells on the beach. I read fiction for fun. I spent time in nature and made memories with loved ones. I also celebrated my first successful beta launch instead of just jumping to the next milestone.

Once in a while, my mind drifted to business. But not with dread or pressure. I even got home and realized my website had been offline the entire time I was away, but I didn’t fixate on it or beat myself up. I don't love it, but it is what it is.

I used to make everything so high-stakes out of habit, out of my own FOMU, out of the constant need to produce, to make sure everything was OK.

But now I'm building new habits. New mindsets. A new pace.

When's the last time you let yourself fully stop?