I didn’t take a sabbatical as a founder, but as a relatively early hire. It was post-IPO but there were some really big hurdles left, and I was leading the tech side of getting over some of them, and an important but background player in quite a few more.
I found myself tired and thinly-spread. I did a lot of interventions throughout the business and in one case, one of our biggest customers, to make sure things would keep working out. Folks in my org couldn’t easily fill my shoes - mostly because it seemed hard to share that stuff - so it wasn’t looking good on a whole bunch of levels for me.
I think that “when it’s time, it’s time” and when that realisation comes, it’s pretty important to do something about it, consequences of not doing so can get grim quite fast.
I told my story to my favourite board members and sold the dream of rolling back some of the bus-factor if I were to take a nice, longish break.
The board - each of them - owed me big time for what I’d done, which may have helped, but I think that the dream of having more folks in my org able to do the tech, stakeholder and cultural work got them over the line in less than a week from suggestion to agreement.
I think my message here: what’s in it for them? Loyalty counts, but it might not be as strong a play as you hope.
I decided to roll off on (paid!!) six month sabbatical about 2 months later.
Those were pretty heavy weeks. I thought I could prep people for growth, change etc. Ha.
I also prepped my sabbatical by interviewing people I trusted who had taken breaks.
The best advice I got was:
- focus on mental plasticity to untangle from the last decade or more
- do new things that are potentially fun
- make bad art and poetry
- do something difficult
- do something intense
- write down some really big questions about what I wanted on my last day at work, put them in an envelope and look at them a few days before the sabbatical ends
- don’t sweat the changes that are bound to take place at $work
Coming back six months later after a lot of adventures and self discovery it became very clear that the genuinely refreshed, new me would get sucked right back in to bad old habits.
So I created a more realistic one year exit plan, got the board to buy into the little steps like all the different org consequences, but not letting them in on my decision to leave - loss of soft power can be a thing - and just after a stupidly high stakes sprint to cap off four years of work of hundreds of people, I did the mic drop. Did a bit of work travel to say goodbye to old colleagues around the world and moved on.
I’m a much happier, well-rounded person and professional now, very picky about the people and situations I choose to associate with. My next gigs weren’t walks in the park but I learned a lot and didn’t pick up much damage in the process of protecting and supporting good people.
Old $work is much more sustainable than if I hadn’t taken the time off and ultimately left. My former colleagues are mostly still there and growing into even more awesome folks than when I was there. All good!