The 3 Most Painful Parts of Leaving My Job at HubSpot

I recently left my job at HubSpot to strike out on my own again (learn more here). It’s been an amazing change so far and I’m super excited about what’s the come, but I’ll be honest and admit it hasn’t been all roses. Since I’ve never left a real job before, I didn’t really anticipate some of the more painful aspects of making such a dramatic change, so I thought I’d share them here.

Losing parts of my digital memory

When I left HubSpot and my work email was shut down, I lost access to a lot of the history around building Leadin. I lost access to my contacts. I lost my Google Docs. It’s amazing how much personal information we store in our work accounts. When you lose your accounts, it like losing a piece of your brain.

Losing my extended community

I braced myself for not working with my direct team mates anymore, but I didn’t prepare myself for losing my extended team. Habits like checking the company wiki when I woke up in the morning were no longer possible. Saying hello and striking up a casual conversation with people in the halls doesn’t happen. It’s easier to focus on GSD when you don’t have many people to talk to throughout the day, but I do miss the small interactions + random conversations.

Recalibrating my top of mind idea

By far the hardest part about leaving HubSpot was recalibrating my brain to not think about Leadin anymore. Leadin occupied my mind almost every waking hour of my day (and sometimes in my dreams). Making such a dramatic shift was painful and I didn’t transition as well as I wanted. I felt a lack of purpose and focus the first two-three weeks because it took me time to shift my top of mind idea. Time heals all, and I’ve transitioned through the five stages of loss, but it definitely was a pain I didn’t anticipate.