Ask HN: Experiences with Co-Founder Sabbaticals

https://news.ycombinator.com/item?id=41849771

by 3dsnano • 2 years ago

3 4 2 years ago

news.ycombinator.com

Hello I am a co-founder of a post-series A startup. Been at it for about 10 years. I recently was pushed out of leadership into a SME role, where I help other companies integrate with our product. I don't write code anymore nor am I involved in strategy. I see the company making a lot of dumb decisions and I feel like I don't have the license, mandate, or energy to go all "founder mode" and try to fix what I see.

It's unsatisfying and boring, but it pays well. I am the top expert in our product and the organization still needs my brain, but the daily feeling of existential dread is getting too loud for me to ignore. It doesn't make sense for me to quit but recently a colleague suggested I take some time off and the idea of a sabbatical has come into mind.

So, I am really interested in hearing stories from other founders who have taken a sabbatical. Did it help restore your energy for your venture or lead you in a different direction? How long did you take off? What goals (if any) did you set for yourself? How did you negotiate this with your other co-founders or board?

codingdave• 2 years ago

This isn't quite the answer you were looking for, but I absolutely have taken sabbaticals in my career when I was feeling burned out. It absolutely helped and re-energized me, and I usually needed 3-6 months off. I'm doing it again at the end of this year, FWIW.

But I did not negotiate it with my employer, I just quit. It will be hard to truly disconnect if you know someone out there has a timeline when they expect you back. Instead, I'd leave things open-ended. If you feel better in the future and want to go back, and they want you back, great. Or maybe you'll find a new direction and not ever want to call them back. That is great, too. Leave yourself open to whatever comes your way.

epc• 2 years ago

Wasn't a founder at the time so feel free to ignore the rest of this, but…after five soul crushing, burn out generating, years as the main guy in the dot com era I took a ~7 month sabbatical. It was awesome, totally reset and cleared my head, allowed me to mentally review what I’d learned and separate the good lessons from the bad. But I did not structure the down time well and felt that I wasted about a third of the time I was out. The biggest downside was that on returning…people wanted me to just go back to what I was doing and I wasn't interested in that at all.

My advice: figure out where you want to go first, even if only as a hazy general notional direction. Is your goal to return to the organization renewed and ready to keep going on what you're doing? Or to find a different path?

Previously: https://news.ycombinator.com/item?id=37827668

com• 2 years ago

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!

t_hinman_esq• 2 years ago

Startups are difficult, and a 10-year run at any company in the startup space is an eternity! No wonder you feel burned out, especially if you feel the company is not going in a direction that gets you excited to get out of bed in the morning. I never took a sabbatical, but having run my own startup, I'm guessing your team probably feels your energy and won't be surprised if you asked for time off. Why not try something small at first -- 4 weeks, maybe -- and see if you can get some clarity about what you want to do next? Good luck!

Ask HN: Experiences with Co-Founder Sabbaticals

Related Stories