How to Sabbatical

Lessons learned from four months alone with my own thoughts

Last week marked the end of my four-month sabbatical.

15 years working in startups and I’ve never had a true sabbatical. I’ve been fired, which was like a forced sabbatical with a healthy dose of depression. Not the same. I’ve taken vacations for 4-6 weeks. But never this long. Never this deep. 

I’m a bit sad it’s coming to an end. I’ve never felt more free, more in control of my life, and more rested. A friend asked me on a scale of 1-10 how would I rate my sabbatical and I said “11”. I can’t recommend taking a sabbatical highly enough if you’re able to. And I’d argue that more of you can take one than you think (more on that below). 

While I’m sad, I’m also excited to start using my brain again. I’m excited to connect with you all and have intellectual conversations again. I’m excited to create.

This week, I’ll share some of the lessons I learned about taking a sabbatical that might inspire you to take one, or help you if you’re on one or planning one.

tl;dr:

1. Look at it like an investment

2. Seriously… turn social media off

3. You may not learn WHAT you want to do next, but you’ll learn HOW you want to do it

4. Don’t set a deadline, you’ll know when your sabbatical is over

5. Make it your goal to not have goals

6. Prepare to go deep on your issues

Alright, let’s dance…

Look at it like an investment

My friend Noah lives what many would call a dream life. He and his wife both work for themselves and travel the world with their kid, living in different cities for months at a time. They have complete autonomy of lifestyle, location, and time. And they’re chill about it, they never seem stressed, even during times when money is tight or they don’t know where they’re going to live next.

When I started my sabbatical I told Noah that I was stressing about our finances. My wife is taking a sabbatical from teaching at the same time as me so we’re losing two incomes and all our benefits while moving across the country (very expensive) and having another baby (very very expensive). 

Noah’s advice: “look at it like an investment”. 

I was looking at it as a cost. “We’re just burning our savings!” He reframed it by asking, “what do you gain from taking this time off together?” Of course, we stood to gain a lot.  A cross-country road trip with our toddler that we’ll never forget. Taking time to heal and refill our cups after both working our butts off for 13 years. Spending deep, quality time together. The list was long.

We weren’t going to be burning cash. We’re going to be investing it in ourselves. What could be a better investment?

My wife and I mapped out all of our expenses for the next year. We calculated that if we made absolutely no income in the next 12 months (unlikely), we would spend $80k of our savings. Was that worth it to us? Yes, it was. Best investment of my life.

You could spend a lot less than us, especially if you’re not moving across the country, or don’t have kids. Not everyone has the ability to take a full sabbatical with their partner. But if you get clear on your numbers, and look at it as an investment, you can make a rational decision rather than just assuming you can’t do it.

Seriously… turn social media off

It’s going to be hard.

You’re going to want to cheat.

You’re going to feel isolated and out of the loop.

But just trust me, the quality of your sabbatical will be 10x greater if you do it without social media. 

Look, social media has brought me tons of value. It’s how I’ve built my career. It does have a lot of positives.

But one thing that social media does is tell you what to think about. You rarely log into social media with a specific goal other than to consume whatever it throws at you. That means you’re letting algorithms decide what you’re focusing your attention on, rather than letting yourself choose.

Your brain will to some dark places and be confronted with difficult questions while on sabbatical (more on that below). Social media will feel like an easy way to escape those thoughts. But it’s really important that you stay. Sit with those thoughts. Process them. The only way out is through. 

I’m so happy I turned social media off, and honestly, after the first two weeks, it felt really easy. Once you get off the hamster wheel, you realize you don’t need it.

One hack that worked for me was to keep The Almanack of Naval Ravikant (free to read online) open on my phone so that whenever I felt the urge to use my phone, I could go to the book. The chapters are bite-sized so they scratched a similar itch to social media.

And the bonus of turning off social media for several months is that when you return to social media, you can be really intentional about setting boundaries around how you’ll use it moving forward. 

You may not learn WHAT you want to do next, but you’ll learn HOW you want to do it

Every time I told someone I’m on sabbatical they asked the same three questions:

Them: How is it?

Me: Incredible.

Them: What’s been your favorite part?

Me: Not working.

Them: Do you know what you’re doing to do next?

Me: Not a clue.

Going into sabbatical, I thought that by the end of my sabbatical, I’ll know what I want to do next. How could I not, with all that time to think and reflect?

I honestly don’t know. I think you can only find out what you want to do by trying a lot of different things and seeing what brings you joy. Since the whole point of my sabbatical was to stop doing things, I wasn’t going to learn what I want to do during that time. I couldn’t think my way through that question. Only action will get me there.

But I learned a lot about HOW I want to do whatever I do next.

A sabbatical is great because it stops your momentum. It’s the literal opposite of the common business advice you get. It’s usually all about momentum momentum momentum. But momentum is a double-edged sword. You build on your success, but you also fall into routines that don’t serve you. You have no space to figure out which parts of your work aren’t serving you.

Your sabbatical will be a full stop and a chance to reset how you live and work.

Whatever I do next, I know that…

• I don’t want to have a boss, I want autonomy

• I don’t want full-time employees, contractors only

• I don’t want to be on Zoom, phone calls are better

• I don’t want to be on Slack, email is better

• I don’t want to have my days booked with meetings, I want open, uninterrupted time to write and create, and have spontaneous conversations

• I don’t want to work with people who I don’t personally respect and enjoy spending time with

• I don’t want to host conferences… please no more conferences

• I don’t want to work more than 3-4 days a week, I want more time for other parts of my life

Returning to work, I can now be clearer with myself and others about my expectations. I know much more about what will make me pumped about work every day.

Don’t set a deadline, you’ll know when your sabbatical is over

In an ideal world, your sabbatical shouldn’t have a pre-defined end date, and you shouldn’t commit to going back to your old job.

I know it’s not possible for everyone. I’m very lucky and privileged to be able to do what I did. Take what you can get. Any sabbatical is better than none.

But my sabbatical would have felt entirely different if I knew I had to go back to work at Bevy when it was done or if there was a hard end date. Bevy was a great place to work, don’t get me wrong. And I probably could have negotiated a paid sabbatical which would have alleviated the financial stress. But I just couldn’t have anyone or anything waiting for me on the other side. No expectations, no goals to come back to, no emails waiting for my response… I needed a full separation from my work life and identity.

It’s not how most sabbaticals work. Companies usually give you something like six paid weeks off every five years. Which is great, and a lot less risk financially. But you miss out on a deeper experience.

My sabbatical had three distinct stages:

1. Wind-down from work

2. Chill and not think about work

3. Wind-up to work 

Six weeks into my sabbatical I was just transitioning from stage 1 to stage 2. It takes time to wind down, especially if your identity has been defined by your work like mine has. If I had to go back to work after 6-weeks, I would have missed the opportunity to fully refill my cup and redefine who I want to be and how I want to show up moving forward.

So just take your time. Don’t force yourself to come back earlier than your mind and body needs. When you find yourself feeling stuck, eager to do something, excited to use your brain and talk to people again, you’ll know you’re ready to start winding down your sabbatical. 

That’s where I’m at now. It took me four months.

Make it your goal to not have goals

Since I was a kid, there was always an expectation of accomplishment in sports, in school, in business…in everything.

I’m hard-wired to achieve.

As I started prepping for my sabbatical, I started thinking about all the things I wanted to accomplish. 

Start painting again.

Learn Hebrew.

Read one book a week.

Take a pottery class.

Meditate and journal every day.

Not working was quickly starting to feel a lot like working.

I made a decision at the start of my sabbatical that my only goal would be to not have any goals. 

I’m so happy I did. My sabbatical became the first time in my life where I had permission to not succeed, to not accomplish, to just be. 

If I felt like reading, I would read. If I felt like writing, I would write. If I wanted to work out, I would work out. But I never set an expectation that I had to do anything. 

Staying off social media made this a lot easier. If I was seeing other people accomplishing every day, I would have felt a lot more pressure to do the same. But unplugging let me stay within my own reality throughout my sabbatical. The only content I consumed was content I chose to consume. No one else could insert their standards into my life. 

As I come back from sabbatical, one of the biggest things I’m working on is figuring out what I want because I want it, and not because it’s how I see myself from the perspective of others. Someone recently framed this for me as your “external self” vs your “internal self”. I feel like I have a more clear idea of my internal self than ever before, and I want to hold onto that.

Managing my social media usage will be a key part of it. My intention is to use social media primarily to create and connect, but not to consume. 

I want my goals to be MY goals, not someone else's.

Prepare to go deep on your issues

I asked another entrepreneur for their advice before I went on sabbatical and he said, “Get a therapist”. 

He told me I would be confronted with a lot of difficult thoughts once I no longer have work to distract me. He was right, I would find myself sitting along with my thoughts for hours on end, especially on long legs of the road trip.

I realized that, for my entire adult life, I’ve used work as an escape. I’d often find myself in a vicious cycle where I work to avoid stress and trauma, then work brings more stress and trauma, and the only solution is to throw myself deeper into work. 

I didn’t end up getting a therapist, but I did have a lot of conversations with my wife and would give close friends calls to talk through the mental chaos. It’s really hard to move past something when you can’t take action on it. It’s hard to think your way through trauma. I wasn’t going to be able to change things about myself by pondering them. I need to talk them out.

I can’t say I’ve solved all my issues on the other side of sabbatical, but I do feel like I’ve gotten a lot more clarity, created more space, and feel more aware of how they’re showing up in my life.

Sabbatical was a sort of self-therapy for me. But you have to fully unplug to achieve this. Otherwise, you’ll just distract yourself with social media or tv or something else in place of work. 

Highly recommend driving 5,000 miles, you’ll get a lot of thinking time (=

---

Reader Questions

I’m going to try something new in the newsletter and answer one question from a reader each week.

Hit reply and send me your question over email along with your Twitter account. If your question is selected, I’ll link to your Twitter so that other readers can also share their answers with you. If you prefer to stay anonymous or not include your Twitter, that’s cool, just let me know.

---

Notes and Contemplations

Things I’m reading and thinking about. They might become future posts…

• Before posting anything on social media, ask yourself, “How would I feel if a member said something like this in a community that I lead?” Do unto other communities as you would have members do unto your community.

• Community people struggle in the world of business because they have to act like they’re not selling and they’re just your friend, even though they work for a business that absolutely is selling. At least salespeople can be upfront that they’re selling you something. Feels inauthentic to have to act like it’s all community when in reality, each member has a dollar value attached to them whether you like it or not. It’s probably better for community professionals to just say up front, “Yes… we want to sell you something. It’s not the only reason we’re building this community, but it is a big reason. If you’re cool with that, come on in.”

• CMX Summit is next week and it’ll be the first time it’s in-person since 2019, and the first since I’ve stepped down. Feeling a lot of feels. I’ll be there just hanging out like a regular ol’ attendee. Hit me up if you’ll be there. If you don’t have a ticket, grab one for 50% here while they last.

• I’m thinking about doing a deep behind-the-scenes look at really successful and really weird communities. Like a case study but less boring. Would you read that? Which community should I do first?

• I feel like the communities we see on the internet are like 1% of the actual communities on the internet, and the other 99% are all in small, private, group message chats. The “community dark web”.

• Fascinating article on the different sides of the question, “should I have kids?”, taken from a socialistic and moralistic perspective, by Nadia Asparouhova.

---

Thanks for all the kind comments and messages from my last post. I read all of them, keep em coming.

Until next time…

-David