I took my first sabbatical this year, after Close started (generously) offering fully paid 4-week sabbaticals for all employees after 5 years.

Recently I spoke with our CEO, Steli, who just came back from his own sabbatical, about how our sabbaticals went and what we learned. Our conversation was recorded for our company’s internal podcast (we use Castos) but I thought I’d also write up some of my sabbatical thoughts and lessons learned while our conversation is still fresh…

Why take a sabbatical?

Besides just being a great perk to take advantage of, a sabbatical is meant to be a time for rest, recharge, and renewal.

I’ve been at Close a very long time (9+ years). Given enough years in the same environment, anyone can get burnt out or just want to take an extended break. Vacations and other regular time off (among other strategies) can help avoid this, however a week at a beach (knowing that your inbox is piling up while you’re gone), is pretty different than taking a more extended break away from work.

Both at Close and elsewhere, I’ve seen long-tenured employees quit or come close to quitting their job even without any specific plan on what they want to pursue next – simply because they felt burnt out or wanted unstructured time to reflect, deal with personal issues, and/or consider their next steps in life.

A sabbatical is a great way to have space for this, without having to quit or use up a year’s worth of vacation time all at once.

I think given several years in the same company, everyone would benefit from an extended break. Hopefully you come back refreshed and renewed!

Planning a sabbatical

Timing – When should I schedule my sabbatical?

Sabbaticals are best planned months in advance, to give yourself and your team adequate time to prepare for your absence. Beyond having advance notice, it’s also good to choose a time when (as much as you can foresee) things aren’t going to be too hectic, so you can truly disconnect during it.

I had first planned, in Feb 2020, to take my sabbatical in the fall of 2020. Not long after making those plans, COVID-19 introduced a huge amount of uncertainty into the world. It soon became pretty clear that 2020 was not going to be a great time to leave the company in great shape since it was such a chaotic time, nor would it have been good for me to be stuck at home on sabbatical. So I waited until things were returning to normal and the company was in a more certain state before I ended up taking mine, earlier this year.

That said, there’s never going to be a perfect time to be away from work, so at some point you just need to pick dates and commit.

Expectations, Hopes, and Goals

I had big expectations for my sabbatical. Beyond just wanting to take an extended break from work and recharge, I wanted to do a lot personally.

I wanted to spend a bunch of extra quality time with my family. We also wanted to take a vacation and take our kids to see snow for the first time.

In the several months prior, I had also accumulated a very large list of other things I wanted or needed to do. My Apple Reminders was full of tasks to accomplish, things to read/explore, home improvement projects, side project ideas, etc. I was excited to have time to really take a crack at this list.

Twice previously, I had taken 4 weeks off for paternity leave and had looked forward to those for similar reasons. But parental leave is very very different from a sabbatical – more about surviving, adjusting as a larger family, and helping with the baby/kids – pretty much the opposite of rest & renewal or lots of time for of personal interests.

Preparing at work

I lead Engineering at Close – nearly 20 people. It was critical that I left the team and company in good shape while I was on sabbatical so things could keep humming along without any disruption.

4+ week sabbaticals are pretty different than a 1-2 week vacation. If you go away for a week or so, things generally operate fine without you. For example you may only miss one instance of a weekly recurring meeting. People will still email you and just expect that you catch up on everything in a few days. At 4+ weeks away, it’s different. Initiatives don’t (or at least shouldn’t) really pause while you’re gone, and you can’t just catch up on everything when you get back. You need to ensure your team can really operate without you, versus just waiting on your turn.

So in the weeks leading up to my 4-week sabbatical, I worked hard to help the company be best prepared for my absence. Examples:

  • I helped ensure that our product development roadmap/plan was planned out a bit farther than was typical.
  • I wrote up new internal wiki pages to document processes that I had previously been doing that I wanted to start delegating.
    • Example: We introduced a new “Cycle Lead” role that an engineering manager would take on to be the person most responsible for a specific 6-week cycle of product development work and communicating that work to the company.
  • Previously I had led all of our weekly Engineering Sync meetings. I changed that by setting a schedule with our engineering leadership team to rotate through leading these meetings both while I was out and after.

In addition to allowing the team to operate smoothly while I was on sabbatical, these were all good things to do anyway, and also gave a chance for others on the team to lead in new ways.

Writing more things down and having processes that don’t rely on you – these are all good things even if you’re not going on a sabbatical.

This preparation work allowed me to more confidently take time off without worrying about how things were going at work.

The Time Off

Finally, my sabbatical came! Now to enjoy it…

Keeping a log

First, I have one big tip for anyone taking extended time off…

I kept a daily log of what I “worked on” or spent significant time on that day. I just used an Apple Note and just wrote a few bullets grouped per day. A day might just look like:

  • Gym
  • Tax prep & call with CPA
  • Lunch out + bike ride with family
  • Caught up with Matt

This simple task helped with a few things:

  1. Help have an idea of where your time went. It’s not hard to wonder “where has all my time been going?” after having long periods of unstructured time, and this helps.
  2. Give a sense of accomplishment each time I added a new thing, even if that thing was just “fun” and not a task.
  3. Prepare for others’ questions. Having a log helped me be able to look back over my entire sabbatical to be able to answer the common question every one of your colleagues will ask: “So, how was your sabbatical? What did you do?”

Don’t underestimate that last point… you can safely expect that pretty much every coworker you talk to in the following month will ask you what you did on your sabbatical. Especially if they haven’t had a chance to do a sabbatical yet, they may have big expectations for you! Be ready to give a clear answer. Reviewing a log can help.

So what did I actually do?

Looking over my daily logs, my time went toward the following.

  • Family: More quality time with my own family every day. Met up with extended family we don’t see often. And when a family member was in the hospital, I was able to visit them.
  • Vacation: Planned a family trip to North Carolina and had a great time: road tripping, mountain cabin, snow tubing, alpine coaster, met up with friends there.
  • House projects: Organized garage, improved home audio setup, planned our house to be painted, got some trees trimmed, got some pool staining handled, fixed that pesky loose toilet paper holder, etc.
  • Friends: Caught up with quite a few friends that I hadn’t talked to in a long time.
  • Personal finance: Worked with a financial advisor, did a lot of reading about investing (Bogleheads, books, articles, FI/RE), did an EOY finance & spending review, did tax prep / worked with CPA, restructured some charitable giving, etc.
  • Learning: Read a couple eng management articles, learned about some new tech stuff, listened to podcasts, watched some talks.
  • Networking: Met with some local SaaS/tech people in my city.
  • COVID vaccines: Got my parents appointments for shots, my wife and I got our shots (made calls daily looking for leftover doses, etc.) Felt a big relief after getting this “project” done!
  • Tech projects: Improved my Raspberry Pi setup and a bit of work on other side projects.
  • Shopping: research and buying a new kitchen dining table set, a new printer, etc.

In summary, my time was spent on a combination of:

  • Family/fun/relaxation/downtime
  • Work on my personal todo list
  • Entertaining whatever unexpected things (good or bad) that came up


4 weeks off sounds like a lot of time, but I didn’t get to do probably even half of what I wanted to do. For example, I thought I’d make a lot of improvements to a side project, but didn’t end up spending any time on it at all.

But I am happy with how I spent my time. In particular, I realized that I ended up spending a lot of time on good things I hadn’t planned on.

In hindsight, it was great having a combination of proactive stuff I wanted to do, but equally great to just have time and space for entertaining other unexpected things that come up.

I went back to work recharged and happy to be back. Extended time away gave me a fresh perspective and clarity on what was most important. I went back with renewed focus on how I should best spend my time/energy at work.

Tips & Lessons Learned

Beyond learning a bunch through reading during my sabbatical, here are my lessons learned about taking sabbaticals:

  • Anything at work I’d need to document or turn into a “process” in order to take extended time off – these are things I probably should have done regardless.
  • It was really great to have a combination of
    • proactive plans and goals to move forward, plus
    • unstructured time to allow space to react to new opportunities and do things I didn’t plan on.
  • Keeping a log of where my time went was really helpful.
  • What I’d do different next time:
    • Would have planned my actual travel plans well ahead of time, before things got mostly booked up.
    • I’d have a bit lower expectation on how much I’d be able to do / how long the time would feel (it did go by very fast)
  • Sabbaticals are a great way to clear your head and come back to work with clear perspective and priority on what’s important.

Overall my sabbatical was a great experience and I was really grateful for opportunity.

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