Lessons and Insights From My Four Month Sabbatical

The Final Review

How did I approach my sabbatical?

I thought long and hard about the ways I could “fail” this sabbatical. Knowing my personality and natural inclinations, I was far and away most worried that I’d mess up my sabbatical by being too structured and too focused on using the time productively. Of course, I knew there was some risk of swinging too far in the opposite direction and finding myself getting to the end of the sixteen weeks and feeling like I completely wasted my time. Ultimately, I decided the best way to ensure I was deliberate with my time was doing biweekly retrospectives where I asked myself three questions: What’s going well? What’s not going as well? How do I want the next two weeks to go?

What had my attention during my sabbatical?

Guilt and shame

The feelings that hit me the earliest and the strongest were ones of guilt and shame. I almost immediately felt guilty that my fiancée, my parents, and other people I’m close to didn’t have, or are unlikely to ever have, an opportunity to step away from their work like this. Our sabbatical policy is incredibly generous and The Ready is an extremely atypical company. Most of the folks in my life do not work for organizations where this could ever be an option for them. But they’re burned out, too. They work incredibly hard. They do great work. Why should I get access to something like this when they don’t?

Small decisions can make a big impact

On day 41 of my sabbatical, after getting a 90 minute massage in the morning, I took a handful of actions over the course of maybe two hours that fundamentally changed the trajectory of the rest of my sabbatical. They were as follows:

  • Putting the bike rack that I had purchased over a year prior (and had been hiding in the back of a closet) on my car.
  • Finding a local triathlon coach and reaching out to him to schedule a consultation.
  • Booking a set of private lessons with a golf coach.
  • Searching Craigslist for a used road bike, finding one, and reaching out to the seller to coordinate the pickup.
  • Finding a local gym, getting a tour, and signing up for a membership.

Ego, identity, and being needed

My identity is largely comprised of the work I do at The Ready and my ego likes being an “important” or “needed” person. Both of these constructs took a beating by realizing that my absence in the day-to-day operation of The Ready was not critical. The work kept going. My colleagues kept doing a great job. I don’t really get the sense that there was much pining and longing for my presence. And that’s a good thing! Truly, it is. It was just interesting to see a large part of my identity basically get put on pause for the better part of four months. It made space for other identities to step into the foreground, but it was definitely strange to no longer be organizing my days by talking to high powered executives or selling six figure consulting projects. If I’m not the org design consultant guy, who even am I?

What am I going to bring forward from my sabbatical and into my work?

Remember the vast expanse of time that summer vacation always felt like when we were kids? Not only did the summer break feel like eternity, it also marked a distinct phase change in your progression through the education system. You’d leave school in June as a fourth grader and you’d come back as a fifth grader. Some of those transitions were even more stark; elementary school to middle school and middle school to high school felt like foundational shifts. I’m thinking about my sabbatical in a similar way. There was Pre-Sabbatical Sam and now there’s Post-Sabbatical Sam. While I didn’t try to fundamentally change my sense of fashion or come back with a wild new haircut, there are a few things that I’m trying to do differently.

Fitness and sleep

My sabbatical helped me remember, or maybe learn for the first time, what it feels like to get enough sleep and to be proud of my level of physical fitness. I think I understand in a much more visceral way how my physical health is the bedrock of everything else. In the past I think I’ve gotten too cute with life hacks and tips and tricks for circumventing taking care of my sleep and my physical body as well as I should have. There are no shortcuts here. Getting enough sleep and doing what I need to do to be physically strong need to be non-negotiables for me. It means sacrificing other things so that these can truly be priorities. No more being “early morning guy” if it means I also become “trying to operate on less sleep than is ideal guy.”

No more Imposter Syndrome

Before this sabbatical I conceptualized myself as a relatively green consultant who may have been at The Ready from day one, but didn’t really have the experience as a consultant that matched the expectationsI thought people had for me. I was still early in my career. I don’t really know what I’m doing. Like many, I was operating through a pretty heavy haze of Imposter Syndrome much of the time.

Working sustainably

There are lots of reasons I eventually got to a point where it felt like a sabbatical was my only option for salvaging my relationship with my career. Among the most important reasons is a complete lack of boundaries. Not boundaries that I failed to establish with other people… but boundaries I needed to set up with myself. It’s my own personal psychology and baggage that set me up for burnout far more than it was any sort of external pressure from colleagues (or even clients). I realized during my sabbatical that this is truly the work that I want to dedicate my life to and while the specific form it may take over the course of my career will likely change, I fundamentally love working with organizations and people. If I want to do this work for an entire career, though, I need to take a longer-term perspective.

Final Thoughts

It was incredibly gratifying to receive such great feedback on all the retrospective articles I wrote over the past four months. I loved the advice, reactions, and thoughts that you all shared with me. I was worried that openly writing about what I was experiencing with my sabbatical would come across as boastful or tone deaf (which I’m sure it did to some folks) but I was hoping that it might be insightful or useful to at least a subset of the folks who read my work. I’ll officially close this project by saying thank you and that I hope all of you get a chance to experience your own sabbaticals at some point, too!



Organization design guy at The Ready.

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