I’d originally planned to take off 3 months. I was tired and frustrated, and all I wanted was to get out of my job in tech and see what else was out there. I thought that by September 2021 I’d have been able to take a break, figure out what matters to me, and pivot into a new job that felt more meaningful.
Well here we are, in January 2022. It’s taken me an extra 4 months, but I’m finally at a point that I can bring my self-prescribed sabbatical to a close. It’s been an unexpectedly trying journey — far from the travel-the-world, drinks-by-the-beach, “fun”-employment experience that people expect. I did learn a LOT about myself — though none of it was easy. I figured out what I’m passionate about — after months of ambiguity, self-denial, and difficult conversation. And I found a new job — after much hesitation to commit to any path.
Though I am completely and utterly grateful to have had this time to regroup, reflect, and reorient, I do think there are some things I could have known from the beginning that would have made this a lot easier. I’d like to share these thoughts with you, in case one day you’re considering jumping off the 9–5 work train and pivoting your career, so that you can be more informed before you take that plunge.
1) You’ll be on sabbatical longer than you think.
I thought I would figure it all out in 3 months. But somehow I always needed more time. By September, I told my partner I needed until October. By October, I realized I needed until the end of the year. By the end of the year, I realized I might need up to 6 more months to secure a job. There was so much more to uncover than I realized — a spontaneous conversation would lead me to a new interesting organization, a phone call would reveal a whole new job field, a pointed question would force me to work through some tough realizations about myself. With so much to explore, I simply needed more time.
There’s always more to work through than you think there is, and this might be the first time you’ve ever gotten to fully explore! There’s a reason most people I knew who took time off in the past had done so for a minimum of one full year. So do yourself a favor and double the amount of time you think you’ll need. It’ll save you the surprise of needing additional time off, and you’ll likely use all that time anyways.
2) Don’t underestimate the importance of money.
Yes, this is probably obvious to a lot of people. But, as someone who grew up in an upper middle class family and then went straight into tech after college, I had never felt the need to pay close attention to my finances. I was privileged, and that made me blissfully unaware.
My sabbatical was the first time I faced true anxiety and stress around money. Taking off more time than I had originally planned for did not come without consequences. By month 4, I no longer felt like I could freely explore because every month, my bank account sank lower and lower to uncomfortable levels, with no money coming in. I began to watch how often I ate out and grew wary of grabbing food with my better off tech friends. My partner and I chose to stay local for his vacation. We had numerous stressful conversations about my job search progress as my partner fretted about having to cover our costs singlehandedly with his meager medical resident salary. When I tried to work some side jobs to support myself, I became acutely aware of how difficult it is to make money that you can live off of and how incredibly cushy it is to work in tech. With my diminishing savings, I felt like I couldn’t afford to look for a job on my own terms, which meant that job searching became stressful as fuck.*
Without a solid financial plan, I constantly felt stressed about money in the latter half of my sabbatical, which meant that I had less energy to stay curious in my explorations. In the end, I was lucky to have parents who were willing and able to help me out, and by letting myself accept their support, I gained some room to breathe. With money comes stability and peace of mind, and that is not something to be underestimated.
3) Dictating your own time is not all rainbows and butterflies.
For a long time, I didn’t understand how people could be content with just working a standard 9–5 job and then going home. Instead, I looked up to startup founders and small business owners, people who were brave enough to create something of their own that they really cared about. I was excited to have a chance to try out that self-directed lifestyle, where I could make my own decisions and pursue my own path.
When I told people I was taking time off, they typically saw this as something super awesome, saying things like, “It’s so cool that you’re just doing your own thing” or “You’re totally living the life!” But after 7 months of sabbatical, I can tell you that being your own boss is not easy. It was exhilarating for sure to have complete control of your time and endless avenues to explore. But that amount of freedom was also terrifying. Because without the 9–5, you have no default structure. You have no guidance. No one depends on your work, so no one has to check up on your progress. All you have is your own steadfast belief in yourself, what you’re doing, and why you are doing it. And if you can’t commit to yourself firmly enough, you will struggle.
So there is something nice about a 9–5. Not only does it provide financial stability, but it also provides structure. And with that structure comes less mental load. At a traditional job, you don’t necessarily have to come up with your own goals; the company gives it to you. You’re given a regular schedule and teammates to talk to. You’re given accountability because your work matters to your company. And when the work day ends, you can do whatever you want with the rest of your evening.
Both lifestyles have different forms of freedom. Just make sure you’re prepared for the pros and cons of the one you choose.
4) It will be an emotional rollercoaster.
A sabbatical gives you space to slow down and think, with very little distraction in the way. I wanted to figure out what I cared about most and how to make that into a career, and for the first time in my life, I had the time and space to do that. Doing this work was incredibly hard. It required me to delve into my deepest fears and insecurities. I had to wrestle with my need for recognition and prestige vs. my desire to be true to my interests. I struggled with identifying my strengths, a situation that forced me to confront my relationship with myself. It was illuminating, exhausting, but also highly rewarding.
Even if you don’t choose to take a long, hard look at yourself during your sabbatical, each day can still be emotionally challenging. I struggled a lot with staying emotionally grounded. One day I’d be ecstatic about a great conversation I had with an inspiring community leader, and on the very next day, I’d feel like shit because I didn’t get enough done. My emotional fluctuation was astounding — and I think it was because I never felt secure enough about the value of my explorations. As time goes on, I’m learning to be more patient. I’ve accepted that the things I’m exploring might take a lifetime to understand. All I can do now is try to be kinder to myself and accept the highs and lows of this journey.
5) You won’t figure it all out.
If you were hoping, like me, that a sabbatical could magically help you identify your life purpose, then you’re going to be in for a wake up call. The truth is, there are a bajillion different paths that you can take next. While you may wish for one obvious choice, you’re probably not going to find it because in reality, none of those possible paths are going to be a bad choice.
During my sabbatical, I discovered philanthropies, non-profit consulting, community management, business school, policy school, and tech as potential career next steps. The number of options I had was paralyzing. I was terrified of making the wrong choice, and so for a long time I didn’t make any at all.
But at some point, you have to move forward. You have to choose a path. If that path is awesome, then great! If that path sucks, that’s okay! You will have learned something, and now you can go try something else. There are still so many paths just waiting to be discovered, and if you can try even just one, then your sabbatical will have been a success.
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Even though there is a lot about a sabbatical that is daunting, if you asked me if I’d do it again, I’d say yes every single time. There will always be unexpected hurdles, but the personal growth was so rewarding. I learned more about myself in 7 months than I have in years. I finally admitted to myself that I love building relationships and creating warm fuzzy places of belonging, even though I had been trained in the objective world of hard science and tech. I realized that I wasn’t ready to go after my own project or idea full-time, and that I currently want to learn from others at a company provides me some structure. And I’ve accepted that I don’t need to be a start-up founder or a super technical person to prove myself to others.
Though my sabbatical has come to end, my commitment to exploration will continue onward. Specifically, I will continue to explore what strong communities look like in both physical and virtual spaces. Next month, I’ll be joining Orbit to help community managers build stronger online communities. I’ll be supporting Redwood City’s Downtown Streets Team through work on the community advisory board. I’m exploring what an ultimate frisbee team could look like if it was centered around community instead of around winning. I’m grateful that my sabbatical gave me time to discover my passion for communities and build the right mindset for lifelong learning. I’m super excited to tackle this next phase of my life with curiosity, intention, and a constant lookout for growth.
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Notes
* I understand everyone has different thresholds for financial stress and so I want to be transparent about my financial situation. I was essentially “cash-poor”, meaning that I had low liquid assets (aka money that could be easily pulled from my bank account). I knew I comfortably had enough for 3–4 months off, but that 7 months off would be my upper limit. I had money set aside in some investments and my retirement account, but I made a conscious choice to try to not pull any money from these sources. When my liquid assets got tighter and I was seriously considering pulling money out of my investment account to help, my parents stepped in and decided they’d rather provide me some money instead of having me cash out on my money in the market.
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Have opinions? Questions? Been on sabbatical before and want to exchange thoughts? I’m always down for a good conversation where I can learn from others! Just reach out :)
