5 Lessons from Taking a Sabbatical as a Co-Founder/CTO

One of the benefits we have at Gusto is a one-month paid sabbatical after five years of employment with the company. As a co-founder of the company, I was among the first employees to be eligible to take the sabbatical.

As someone who’s never taken so much time off and traveled alone before, I felt a little bit of excitement and lot of anxiety. I’m a somewhat shy person and meeting new people isn’t exactly my forte. Would I get lonely and want to go home early? What if something bad happens at Gusto while I'm away? What if I don’t get that epiphany or creative insight that so many tech workers say sabbaticals are useful for? Would I still be as excited about Gusto when I come back?

Lots of questions swirled through my mind, but I finally booked a one-way plane ticket to Chile with no plans other than to figure things out once I land.

By the end of my trip, my mindset completely shifted. All the questions I had were eventually answered, my mind quieted, and and I learned a few important life lessons which I’ll share here.

Lesson #1: Don’t plan everything out and check the boxes.

Don’t go on TripAdvisor and figure out a way to optimize your itinerary to see all the top 10 things to do in a day. In our world of Pivotal Tracker, JIRA boards, OKRs, sprint planning, and standups, it’s easy to fall into that trap, especially if you’re an engineer and love to optimize.

Instead, take extra time to experience it. It’s better to hike up a valley to have Gray Glacier gradually reveal itself to you over a period of eight hours than to sign up for an overcrowded boat ride that gets you there in an hour so you can snap a few photos before moving on to the next destination.

The photos of the glacier you show your friends are exactly the same, but your experience and memories of it are completely different. It’s the difference between having a crawfish boil with friends versus ordering pre-peeled crawfish at a restaurant that you shovel into your mouth with a fork.

Stopping to eat lunch in front of a lake en-route to Gray Glacier in Patagonia.

Lesson #2: Traveling alone isn’t just about being alone.

Traveling alone isn't only nice because you get much-needed “me time” to reflect on your life. You definitely do get a fair bit of that, but truth be told, it gets old pretty quickly and you start to feel lonely, even as an introvert.

More than getting valuable alone time, I learned that traveling alone is nice because it opens up more opportunities for you to meet people from different walks of life you would otherwise not meet if you were travelling with friends.

After getting tired of reading my book on the bus, I mustered the courage to strike up a conversation with the person sitting next to me. He turned out to be Peruvian traveling on vacation as well. Though he was from a completely different world from my own, we became the best of friends for the next few days, simultaneously learning about each other’s worlds while sharing amazing new experiences in Chile together.

Lesson #3: First impressions are often wrong.

I met a lot of people that I prematurely judged before taking the time to get to know them.

One person I was sitting next to had headphones on and didn’t make eye contact with me for a couple hours. Though I didn’t talk to him, I thought him to be unfriendly. Despite my impression of him, I decided to talk to him anyway. I realized my first impression of him was completely wrong. We started planning all our hikes together, jumped in freezing cold lakes together, and shared many interesting facts with each other over meals. When I told him I would’ve liked to extend my stay one more night at the hotel but the front desk told me that there was no more availability, he secretly campaigned to the hotel manager (who he had a connection to) to try to make it happen for me.

On multiple occasions, people I took the time to get to know turned out to be very different from how I initially imagined them to be. I learned that when I’m afraid or intimidated to initiate conversation with someone, I tend to project a slightly negative judgment on that person. Perhaps this is one of the ways my mind rationalizes not talking to them. Once I fought my intuition and struck up a conversation with that person, I found I really enjoyed getting to know them. We should resist our impulses to judge what someone is like before actually engaging with them.

After getting to know someone, you find yourself pulling tables together so you can eat next to each other.

Learning #4: To disconnect from work, tell your colleagues you’re going to disconnect.

One of the biggest personal challenges I set for myself on the sabbatical is to learn how to disconnect from the day-to-day when I’m on vacation and focus on myself.

This may sound obvious at first, but I learned that there can be a virtuous or vicious cycle to disconnecting. If you tell your colleagues you’re going to disconnect and won’t be very available, they send you fewer messages. If you get fewer messages, you start to check your inbox less often. This in turn reinforces the fact that you’re not as available. Eventually, the messages that need your direct response peter out.

The opposite is also true. If you respond to a message, it signals to your colleagues that you’re available, which encourages them to send more messages to you, compeling you to be more available.

As someone who’s always checked email on vacation and never used an email auto-responder in my life, I started my sabbatical not being successful at disconnecting from work. After years of being “on,” it became habit to check Slack and email as soon as I whip out my smartphone to look for directions to get back to my hotel or find a translation for a word. It’s exacerbated by the fact that you’re alone and sometimes check out of boredom. It was also hard to get over a sense of guilt about being disconnected.

The only way I was able to turn this vicious cycle into a virtuous cycle was to completely uninstall Slack and email from my phone. Miraculously, this worked. Colleagues started feeling empowered to make decisions without my input. Messages requiring my direct response slowly petered out. By the second week, I eventually felt at ease with not checking messages daily.

Lesson #5: It’s hard to meet people just by sitting alone in bars or restaurants. But other options exist.

People say staying at hostels are the best way to meet other people when you’re traveling. At this stage in my life (I'm 35), I’ve grown a little too old and accustomed to comfort to stay at hostels. If you’re willing to splurge a little (and I think you should on something as rare as a sabbatical), programs like Explora are great at fostering a community of travelers and make it much easier to meet people. You still have to put yourself out there and get comfortable with the awkwardness of walking up and introducing yourself to another traveler, but I found it a lot easier than meeting someone at a bar or restaurant and a lot more comfortable than a hostel. These programs do tend to attract older couples (who were among the most interesting people I met!), but there are also enough like-aged travelers to form a good gang.

Some very kind Canadian travelers I met.

Final thoughts.

I feel incredibly lucky to have had an opportunity to take a sabbatical through Gusto. I started my sabbatical with anxiety, apprehension, and guilt, but ended with greater happiness, some important life lessons, and a deep sense of gratitude for my life. It was truly a once-in-a-lifetime experience. I feel thankful to be able to do a personal sabbatical AND have a great place to go back to work afterwards.

Did I get lonely on my sabbatical? Yes, especially in the beginning when I was still learning the above lessons. Towards the end though, I got really good at breaking through my shyness, initiating conversations, and making new friends. The last day of my trip felt a lot like summer camp ending: We were giving each other teary-eyed goodbyes and making promises to see each other again.

Did things break down at work? No. Gusto charged on without me, and especially so once I learned to disconnect and my colleagues felt more empowered to make decisions without me being there. I think this was a huge win for my team in its ability to scale.

Did I achieve an epiphany or have the “ah-ha” moment during my sabbatical that tech workers sometimes say they have? Personally, I didn’t. I won’t be making a bunch of drastic changes my first day back at work as a result of my time away. But I do believe that taking an extended break and traveling alone gave me a broader perspective, some great life lessons, and made me a happier person. And that’s definitely good for Gusto.

I’m incredibly excited to get back to work helping Gusto achieve our mission and I come back a wiser and happier person, with a much broader perspective.

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