Taking a Sabbatical

The following is a guest post by Jonathan Baker. He's been working with me the last few months to launch a new product offering...and streamline our existing systems. He took a sabbatical, you lived through 2020, and you're about to take a long weekend, so what better time than now to think about this.

Stage One: Starting

TL;DR: Sabbaticals are awesome. It’s easy to justify one from a personal perspective: time to regroup, learn something new, reconnect with yourself… you get the idea. But there is a compelling argument to be made that a sabbatical would not only be good for you, but also be good for your business. After the wild ride that 2020 was for most of us, you might find yourself just now able to come up for air, and looking for a way to reboot like I was a few years ago.

Eight years into growing my own business (a craft brewery based in Atlanta), I was feeling a bit burnt out, bored, and trapped. I didn’t want my business to define who I was, but after doing it for so long, it felt like an inevitability. I decided to pursue a sabbatical, and after some careful planning, I was able to sneak in 6 weeks before my second child was born. In the moment, it was liberating. No email, no Slack, no pesky employees with their pesky problems. I traveled, built some furniture (AKA bought some new power tools), and got back into shape. Six weeks later, I returned to work not necessarily feeling like I’d accomplished much, but nonetheless refreshed.

Looking back now, I had accomplished much more than I thought during my sabbatical. In the background, I’d been percolating on the long-term vision of our brewery, and I came back with renewed vigor and quickly developed a game plan. We revamped the marketing department, starting looking for new taproom space in different states (and ended up opening a brewpub in Birmingham, AL), and I was able to connect more deeply with those “pesky employees” previously mentioned. Now, I think I know why my sabbatical was actually good for our business.

The ‘Why’

Here are a handful of business reasons for you to take a sabbatical. Note they are not mutually exclusive, but in most cases additive.

  • You are able to pressure test your team in a relatively low pressure environment. How much damage could they actually do in 2 months?
  • You can more easily identify the areas of the company where you are still needed, and also the areas that would actually be better off without you. It was surprising to me that I was stifling parts of our business with my meddling – something I wouldn’t have realized unless I stopped meddling.
  • You have more focus upon returning, as the squeaky wheels have been identified and you are no longer tied to as many day-to-day tasks.
  • You are able to give the company what it needs from you as an owner: direction. The more you grow and the longer you’re around, the less your business needs you to “do.” What your business actually needs is someone to pick up their head and look forward five years, working to steer the ship (slowly) in that direction.
  • This last one is mostly personal instead of business, but I’ll throw it in here anyway. You need to be reminded of what you want out of life. You’ve been working yourself to the bone for years, making far less money than you’re worth, and you need to reconnect to your own “why”.

Surprisingly, planning for a sabbatical can be almost as helpful to your business as the sabbatical itself. It will give you a true read on how you’re spending your time, how supportive your team is, and what job roles might need to be reshuffled permanently.

The ‘How’

Assuming you’re marginally convinced there is a business case to be made for a sabbatical, how should you go about taking one? Here’s the process I followed, with a few tweaks that I would have made in hindsight.

  1. Share your intentions with your partners and/or senior leadership team. Let them know your reasoning and how you hope it will help the business long-term. And don’t be afraid to inject some personal reasons too. Give them a high level timeline (12-18 months) to work towards. Something that feels far enough away to avoid freaking them out, but close enough to give you hope. Six weeks should be the absolute minimum amount of time you allot for a sabbatical. Anything above that is gravy. I wish I’d planned for 8-10 weeks, looking back.
  2. Pick a 4-6 week period early on and start keeping a list of all the things that you would need to transition before a sabbatical was possible. You need to keep an active, ongoing list. There are going to be plenty of small things you won’t remember if you try to brainstorm in one sitting. Effectively, every single one of your day-to-day job functions needs to have a backstop.
  3. Once you have your list, go through it and for each item:
    1. Write down who in (or outside of) your firm you plan on transitioning the item to.
    2. Decide if it’s something you should be doing at all. If not, make it a permanent transition. If there’s still a good reason for you to be reconciling bank accounts every month, then make it a temporary transition.
    3. At this point, you should have a list of employee names, and a list of responsibilities for each person.
    4. Sit down with each employee and talk through a training plan. In many cases you’ll be able to frame this plan as “professional development” without feeling too guilty about it. Regardless, your employees wantyou focused on the bigger picture. That’s your job, not theirs. They’ll be understanding if you are honest with them about your reasons. And if they’re not understanding, they’re probably not employees you want to keep around for long.
    5. Train. Ideally over a 2-3 month period, not the frantic “last week before you leave.” Make sure everyone is fully trained at least a month before your planned sabbatical so you can jump in and work through any kinks if necessary. Yes, this will be a very boring month for you, hopefully. Use it to catch up with clients, old friends, and maybe drink a few lunch margaritas. You’re worth it.
  4. Set expectations. You will be turning off email and Slack. You won’t be checking in. Designate 1-2 people in the company as the only people who are allowed to contact you, and then only if urgent, and only by the method you request. I chose text message. These employees will be able to run interference for you and hopefully catch most (or all) of the bullshit before it works its way back to you.
  5. Upon your triumphant return, schedule debriefs with most of your employees to get their perspective on how things went, what you should be focusing on, and what they learned about themselves. Schedule dedicated time with your partners and/or leadership team to get their perspectives as well. Share your learnings, and talk through a revised job description for yourself moving forward.

I will admit, taking a sabbatical was much easier to do with understanding business partners who could help hold things together in my stead. But that doesn’t mean it’s impossible even without partners.

If you can’t get the idea of a sabbatical out of your mind, it’s probably a good time to start planning one. And you shouldn’t feel guilty about it, because even if it might not feel like it, it will be good for your business. Trust me. Even if I’m wrong, you’ll get a few new power tools and some lunch margaritas out of it, so there’s really no downside.


My father says I’m not supposed to do any active selling in these content pieces, but I don’t think he reads the footnotes. If after all of this you still aren’t sure how to go about taking a sabbatical, but know you need one, I’d be happy to be your sabbatical consultant. I take payment in American dollars and American craft beer: [email protected]

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