Sabbatical Season: My Summer of Strategically Doing Nothing
How the practice has helped me reinvent myself many times over
*To all recent subscribers - while I mainly write about go-to-market strategies, I also tend to include a heavy dose of life design in my writing. Such as today’s article. Also, in a survey I sent out a while back, your favorite content was behind-the-scenes pieces, so enjoy.*
Every year I take a multi-month sabbatical. I actually do this twice a year, in the winter and in the summer. The summer break typically coincides near my birthday, starting on May 15th and ending on July 15th. Although, sometimes I extend it into August if that feels right.
It’s not a complete reprieve from any and all responsibility. For example, I do work during this period. Although I take a lot of PTO during that period-I earn upwards of five weeks off per year. In fact, during June I’ll only work four out twenty-two work days.
Beyond work, I power down from all the other normal hustle and grind of my daily life. That includes virtually no side projects, unless they are something that is a) extremely interesting to me; b) ridiculously lucrative. For the past three years no project has met those conditions enough to entice me away from my side-hustle sabbatical. This time also includes writing less, although when “inspired” I do write some, since writing is one of my favorite things to do to relax.
If you’ve never taken a break like this, I can’t recommend it enough. The benefits aren’t endless, but there are many.
Room for deep work
I spend my sabbatical asking myself deep questions about the future. Like:
Is the work I’m doing fulfilling?
I’m I working with people I can learn from?
Am I focused on the right skills to be acquiring?
Which projects were the most exciting to work on? What are the common themes of those projects?
More times than not, it’s been the deep work I do during a sabbatical that led to a professional change in course.
For example, it was a winter sabbatical ten plus years ago that led me to the decision to leave the bank where I was Chief Lending Officer and, according to the CEO and a few Board members, the likely next CEO. It was this past winter sabbatical where I realized that I was ready to move on from leading my company’s largest product build in its 50+ year history. One that I helped incubate.
Asking hard questions, doing the deep work, during these sabbaticals has fundamentally changed my life for the better.
Room for re-invention
I use my sabbaticals to re-invent my life. During this down time, away from many of the normal things that take up my energy, I audit what is working and what isn’t. If something is an energy drain, and not fundamentally necessary to our livelihood, I cut it out of my life. That may include business activities, events I was attending, or even people I was spending my time with. Creating distance from those things over an extended period gives me the space I need to evaluate if they are serving me or if I was serving them.
Room for family
Ten years ago I made the decision to leave a role where I was being told that I was the next CEO. I was ready for a new challenge and the decision to transition out of that role was partially because I wanted to work from home, where I could be around my wife and daughter more. That decision has been one of the best decisions I’ve made, because I’ve been afforded all kinds of “stolen moments” over the past decade.
I would estimate that my family time goes up by 25%-40% when I’m on sabbatical. This summer will be different than past summers, since our daughter is driving now. Still, this time gives me more chances to bond with my family and make relationship deposits for upcoming times when I may not have as much bandwidth.
Room for my hobbies
I’m fortunate to have time to explore my main hobbies through a normal week. They include video games, which I’ve played for 47 years now, reading, and writing. During my two sabbaticals, I ramp up my time on those things.
The biggest change is that I shift my writing, or most of it, from a professional focus (GTM/Fundraising/etc.) to life design and working on other projects I have been wanting to get to. Right now, the biggest change is that I’ve refocused some of my writing energy into my second fantasy novel. It’s one I’ve been mentally working through for a few years and I think I finally have enough content carved out to keep the ball rolling.
Tips for taking your own sabbatical
If you are considering a similar approach, here’s some tips for you to consider.
Some people take full-on sabbaticals, from virtually everything. They often take long trips as part of their time away. If that’s not something you can afford, in time and money, there’s no reason you can’t take an at home sabbatical. Many, in fact, most of mine was been at home.
Sabbaticals don’t have to be for months to be successful. Mine have ranged from one week to one month. The key is giving yourself enough space to do the deep work.
They don’t have to be an all-or-nothing break from life. In fact, I would tell you that it’s unreasonable to expect that. Social media has contributed to the romanticization of sabbaticals as a modern day pilgrimage to find one’s self. While that is the goal, you don’t need to disappear or put your entire life on hold to accomplish it.
What you can’t expect is to take one sabbatical and it be completely transformational. That’s because it takes time to get used to the break in activity. I’m typically a week or more into my breaks before I am mentally free from all of the other distractions I’ve put aside. In fact, there have been times when I had started a break and then broke it because the inactivity was too hard mentally. That’s why, if you decide to give it a go, don’t be disappointed if your first few attempts feel more like a typical vacation than a true sabbatical.
I’m one month into this summer sabbatical, and I can already tell it’s going to be one of my more impactful/productive breaks. From the start I felt free of a lot of things and I wasn’t feeling the pull towards activity that was there in when I started taking these breaks. I can’t wait to report back on the deep work I did and the decisions I make.
See you in July/August!