On March 1st, Rich and I celebrated the one year anniversary of incorporating Jupiter. Over the course of the year we have:
I had all intentions going in to better document our journey along the way. Once in the hamster wheel though, it became difficult to understand which decisions were private and/or inconsequential.
It’s been a year now and this moment is worthy of a check-in. Some acknowledgement is due.
I leaned on a lot of what I learned at Shopify about hiring. We pooled candidates, reached out to heads of bootcamps and schools, promoted it on every (free) network we could, and spent four weeks going through every application.
Our results are as follows:
We intend to keep much of the process the same next time except do it over an extended period of time (purely for exhaustion reasons). We made our first mistake here with hiring because we didn’t fully understand how much it cost to onboard someone.
Every person added to a team will create more work, for sure, but it also subtracts time from whoever their direct manager is. In a start-up that time is very limited (especially of a CTO) and we made a bad call somewhere along the way… believing we had more time than we did.
Both of us came in saying we didn’t want to work “hustle hours.” When you have a start-up and this value, it forces prioritization.
Over time I have realized my life works as an integrated mesh. A pull in one area pulled everything around it too. Things in my personal life had to shift to accommodate for deep work sessions and many days I’m strictly scheduled to make sure I get in my training, deep work, and self-care.
All that being said, I did notice that doing that for too long caused me to feel restricted. Every few weeks I’ll ease up on the routine to give myself the mental break required to stay efficient and content.
Peace of mind gives me time time to make better decisions. I can let data rest instead of reacting. As a result, I’m more confident, can move on from past decisions faster, and have room to analyze for lessons learned and outcomes after-the-fact.
This has been a habit which started years ago but Jupiter has reinforced it over time: peace of mind needs to be protected–especially in a start-up.
I often observe others (or even myself) losing the context of life–fixating or ruminating on the business or things which won’t move the needle, because that’s all you have. Finding other things in my life I love has been sustaining.
Putting boundaries on myself for peace of mind, as mentioned, also ensures that I never lose context. The sun continues to shine and my lizard needs bugs to eat. In the grand scheme of things, most decisions don’t really matter and most decisions can be reversed. It’s not worth giving yourself anxiety over every little thing.
The key is to make sure you knew it was a decision to begin with. No one has complete information but if you go in with eyes wide open, the consequences aren’t ever that melodramatic.
We haven’t made that many decisions I regret–just one in a year. I think that’s a sign of us working well together but I also think that’s a sign of us understanding why and when things don’t really matter.
I left my last position at Shopify half an hour after knowing I was unhappy–nothing was lined up and months were spent wondering if I should remain in tech. I read books, went on a long walk, wrote 80% of a product design book, researched different career paths, and went to Antarctica.
It’s been more than two years from that time. I think you can always tell if something is really meant for you when you’re ready to walk away. In retrospect I simply needed a challenge which suited my strengths.
I’m so grateful to be in this position and I hope the future years are as nourishing as this one has been.