Consider the Career Break

some nuggets on how i went about my gap year

Why, hello there! A few friends are soon embarking on their own career sabbaticals, so I’m finally writing down some reflections and tips on how to plan a gap year. I wanted to write things down now, while they’re still fresh, so I can keep helping people in the future. Sorry that this is six months late! The final travel recaps are coming, plus a longer, unrelated essay 🫨.

ALSO, A WARNING: I’m an extreme Virgo (i.e. crazy organized), so this level of planning may not be for everyone, but I hope that you can take away something useful from this. 💕 If you have any additional thoughts and questions, leave them in the comments, or hmu.

How the Gap Year Came To Be

I didn’t know I was planning a gap year at first. I knew that I was feeling underutilized and plateauing at my current job. And there were so many interesting things bubbling up to explore. 

I had just returned from a 5-week work trip and Spanish immersion school in Mexico City and Oaxaca. I joined two friends, Megha and Abena, to practice solo travel, together. It was like training wheels for solo travel. We stayed in separate lodging and would have our own fun, but hung out every few days to check in. 

I returned to San Francisco electrified, hungry for more solo travel. For the last ten years, I had filled every summer break and free moment with a structured activity to advance me in my academics or career. Everything was oriented toward the promise of external approval. That first time abroad, I realized how liberating it felt to control my own time, to live each day exactly as I desired. 

Slack had unlimited PTO, so I eagerly began planning the next year. There would be climate farm school in the spring, yoga teacher training in the fall. I help at the indie perfume store Ministry of Scent in San Francisco, so I reached out to Ernesto Collado, the creator of the natural perfumery Bravanariz on a whim. I didn’t expect him to warmly welcome me to his small village. How does all of June and July sound?, he wrote in an email. I agreed right away. 

In that moment, I realized that I would have to quit my job to accomplish all of this. At first I was hoping to just take leave and go away for a few months, but when a friend Zahir suggested that I just take a whole year, I knew deep down that this was what I needed. Taking this much time away would give me the space to reclaim my energy, to figure out who I was without so many other things competing for my time, my attention, my self. 

Except for Zahir, I knew very few people who had taken extended time away from work. It wasn’t a common thing that people around me did. Because of this, some days, I would wake up panicked, full of regret. Reminding myself that this was the only step forward that I wanted to take helped ground me. If I wasn’t going to do this now, when, if ever? And, in the grand scheme of things, six months, a year, two years, is not that much time to be away. Although I was leaving for a year, I wasn’t going to be leaving my whole life behind. 

Gap year planning: the WHY, WHAT, the WHERE

I began my planning very broadly. I had a few set dates going in, but everything else was a blank canvas. 

Create Your North Star

I called a mentor, who had taken his own gap year. He structured his gap year by setting a North Star, a few big recurring themes. He would return to these themes when feeling lost on what to do next, and he would use these theme as touch points, to check in on how his travels had changed him so far. His North Star was DANCE. 

After this advice, I decided on three key themes: spirituality, climate, and programming. I was committed to working at a climate startup after returning to my gap year, so I wanted my personal learning to focus on deepening knowledge of climate change solutions and my full stack programming skills. 

Write, Visualize, Reflect 

While planning, I made SO. MANY. LISTS. Books I wanted to read, coding classes to take, endless Workaway opportunities, a bucket list of the wildest experiences I could imagine. I googled a ton for gap year reflection questions. I did all the exercises in Design Your Life, which is a great resource for life in general. 

Some questions that were helpful to me to chew on (some from me, some from others):

• How do I want to change as a person?

• What is this gap year about?

• What is this gap year NOT about?

• How do I want to feel during my gap year? At the end of my gap year?

• What artifacts do I want to produce from this experience? (I chose to maintain a daily private journal and a public blog)

• What do I want to learn?

• What personal qualities am I most proud to have and which do I want to cultivate?

• How will taking a gap year help me prepare for my future?

• What life skills should I develop that will help me thrive as an adult?

• Do I have healthy habits? How might I live more healthfully on my gap year?

In addition to writing, visualizing helped a ton. Closing my eyes and embodying how I wanted to feel. I made Pinterest boards and watched YouTube vloggers as well. I scrolled around on google maps. I looked at the most harmonious locations for me in the world, according to astrocartogtaphy. 

I didn’t pressure myself to figure everything out at once. I only planned a basic structure for the first 2-3 months, forbidding myself from planning any farther in advance. 

A big help to me was trying to strike a balance between structured experiences and free travel, between staying in private rooms to recharge and hostel dorms to make new friends. I loved having a few weeks or more to get to know a group of people well, working on a shared goal together. This was balanced really well by time to reflect alone in hostels, traveling bit by bit through a country. But I found that if I spent too many days in a hostel dorm, my battery drained quickly. I would feel trapped and lost, anonymous in a sea of constantly changing faces. 

I also liked working toward a learning goal on the side while traveling. I would give myself time between classes, though, to not overwhelm myself. For example, I went through the Terra.do 12-week class on climate change while apprenticing at the perfumery. I took a journalism class, a Chinese class, and more. Making progress toward these learning goals was grounding for me when moving around a lot. 

After answering these big questions, I picked out a few places that I most wanted to explore, connecting the dots between the big structured experiences that I booked in advance. 

I found that I liked spending 2-4 months in a region and then moving on, because I would get a bit antsy after too much of the same scenery. I ended up doing 4 months in Europe, 3.5 months in Central America, 2.5 months in South America, a quick stint back in Spain to hike the Camino, and 2 months in Eastern Asia. 

Between these chunks, I would go home for a few weeks to recharge and see friends and family. People also periodically came to travel with me.

Gap Year Planning: the HOW

Misc.

• Make sure your vaccines are up to date!! You can go to a travel health clinic and show them a list of potential countries. Some of the vaccines can be quite expensive, but my insurance covered a good bit of them. One vaccine I needed for central and South America was the yellow fever vaccine. 

• I also grabbed some travel insurance for medical emergencies. I don’t have a specific travel insurance rec, because I luckily never had to make a claim. I also made physical and digital copies of my important documents like passport, covid vaccine, and drivers license. 

• Get a good travel rewards credit card and a debit card without ATM foreign transaction fees!! The chase sapphire reserve card has been awesome. It often has a great sign up bonus, and gives you priority pass airport lounge access!! I also got the Schwab debit card, and it worked like a charm. I tried to carry several credit cards and debit cards with me while away. This worked great because one debit card and one credit card ended up getting hacked, so I couldn’t use those cards until someone brought me a replacement that I had to ship to the States. 

• Most credit cards have insurance for problems with travel things like flights, luggage, and rental cars. Making charge backs to my credit card was great for the few times that places tried to scam or overcharge me. 

• Figure out where you’re going to put your stuff!! I ended up selling my car and all of my furniture because I knew that I was going to move to New York after finishing the gap year. I mailed everything else back home to store with my parents. If you’re returning to the same place after, maybe you’ll just need to find someone trustworthy to sublet your apartment to. 

Packing

I practiced packing, over and over. I went through numerous rounds of packing my two backpacks: an Osprey 45L Fairview and a smaller computer bag. I first drafted a list of everything I might need, because it’s easy to get caught up in emotional attachment to certain articles of clothing. Several friends sat with me on FaceTime and helped me whittle down piles into a final selection. 

Even after all this, my backpack was so full on the first flight out that I had to zip up its straps and drag it on the ground, tearing some holes in the exterior fabric. I learned quickly that I didn’t need as much as I thought I did. It was less stressful to have a less than 100% full backpack than to stress about fitting everything into my packed bag every time I moved hostels. I worried a lot before leaving about forgetting something, but usually, you’ll be able to replace whatever it is on the road.

Also, the contents of your backpack don’t have to be static. I was constantly refining the contents of my backpack over the gap year. It was helpful to switch out general summer clothes for winter during a visit home. 

Here’s some items that ended up being essential:

• Luggage locks: great for when you leave your bags in an unwatched hostel all day after checking out, and for peace of mind when in transit. I never had anything stolen, and these locks probably were a big reason why. 

• Mini medical kit: prescriptions, travelers diarrhea pills, neosporin, bandaids, tweezers, etc.

• Kindle: saved me from packing 25+ books in an additional suitcase, my stubborn original plan

• Travel adapter and power bank

• Travel cubes, or ways to compress and compartmentalize your luggage space

• Sleep kit: ear plugs and eye mask, to survive any hostel dorm room ruckus. 

• Shower shoes: to survive any hostel shower floor ruckus.

• MINIMAL DENIM: that shit HEAVY.

• Clothes you’re not too attached to: I burnt through so many pairs of socks and basic pieces from heavy wear. 

💰 Finances 💰 

Gap year budgets can vary a ton for people!! Some people make it a whole year or more spending $500 a month, with the help of the many awesome work-stay programs available. Others I met spend could spend up to $4-5k per month. There’s a huge variety of budgets that people are following. The experience you get with each spending level is different, but equally valuable. 

I went over my original goal because I didn’t track spending closely for the first four months, and I chose to spend time in several expensive countries (Ireland, the Galapagos, East Asia.) and on several expensive experiences. From talking to other people, though, I tended to be on the mid-upper end of spending. I leant more toward going over budget for experiences because time is worth more than money for me at this age, but again, what you spend money on depends on what you value! 

It’s a good routine to try to record your expenses and assess your spending habits monthly. A big thing is to keep enough money left over to handle a few months of your typical spending in whatever city you end up in after finishing the sabbatical. 

Here are some tips I picked up to be more budget conscious:

• Travel in places where your currency is relatively strong and the cost of living is lower. Western Europe and East Asia have comparable or higher costs of living to the US. A hostel bunk in these areas can go for $100+, especially during a popular season. 

• Going with that, travel during shoulder seasons or off seasons for discounted pricing. 

• Travel Spend is the app I started using four months into my gap year, when I realized I was over budget. I tracked every single expense in this thing. You can get the premium version but the free version worked just fine.

• I did some freelance work, which brought in a little extra cash. Saw other people doing this too!

• Booking.com has some good deals if you are booking repeatedly through them. 

• Private rooms in hostels can be a lot cheaper than a hotel room, but offer just as much peace and quiet. 

• Check around for backpacker discounts, young traveler discounts! 

• Menu of the day at restaurants is a game changer, < $5 in central and South American countries.

• I would cook when staying in one place for longer. I would also try to book places with free breakfast. 

• Work stays!!! workaway.info is what I used, but you can find many other opportunities you can find online. Lodging and food are usually provided. Note: some countries, like Japan, have really high demand for work stays, or a particular work stay could be really popular. You might want to make arrangements a few months in advance.

• Taxes: if you begin your gap year partway through the year, you should get a pretty nice tax return the following spring. 👌👌

Before You Leave

Honor Your Community

Since I knew I was taking a gap year several months before I actually left, I had the time to think about how I wanted to honor my time and community in San Francisco. I challenged myself to host a different gathering once a month from January-May, culminating in a tender farewell dinner and a giveaway of my remaining apartment things.  I left feeling connected to friends here and with plans to reunite with them again after my return. 

I tried to hit some of my favorite spots in town before leaving, to see San Francisco with fresh eyes. 

I also wanted to bookend the gap year with a mini adventure in itself. Using my final days of PTO, I went to run my first marathon, Big Sur, with Liam.  Then, I took the solo road trip of my dreams, going up and down the west coast to get to the Terra.do climate farm school on Lopez Island. I was very attached to my old car, a beautiful Mazda 6, so this was our final trip together. When I made it home, I felt ready to go. 

Record Work Projects in Detail

Before leaving for your adventure, or early in the trip, I would take a few hours to write down some detailed notes about your biggest work projects and accomplishments. You want to include enough detail to be able to reference these projects in job interviews a year or more down the line. When I quit, I had saved some  bulleted lists of my projects, but that wasn’t enough for job interviews. Write about your work projects as if you’re going to forget everything about them. It could even be helpful to record yourself talking about them!

During the Gap Year

Okay, we’ve made it!! We are IN the gap year. Congratulations on making it so far!!! Here are a few notes. 

Be a Considerate Traveler

In each place that I visited, my goal was to respect the local community, to get to know a place instead of using it as a backdrop for my personal journey, pumping it dry for Instagram content and moving on to the next. I won’t be able to ever fully reconcile myself with the privilege of travel, but here are some things that I tried to do:

• If I didn’t know the language, I tried to pick up a few phrases to communicate and downloaded offline dictionaries, instead of assuming everyone could speak English.

• I tried to get out and talk to locals, and really listen to them.

• I found local, passionate tour guides. For example, some tours were run by nonprofit organizations, and their proceeds went directly toward community programs.

• I educated myself a bit on the country’s history and current issues (talking to people, consuming media, going on walking tours).

• I volunteered in the community and participated in two Workstay programs away from the big cities.

• I tried to book independently run lodging. I often ended up just going with the cheapest well-rated option, though.

• I tried to reduce my carbon footprint by traveling slowly, locally, and minimizing the flights I took.

• Show gratitude. Simple thank yous can go a long way, in addition to tips and little tokens of appreciation.

Changing Course

You might find yourself changing course several times throughout your sabbatical. That is totally okay! You did the initial planning for the trip when you weren’t traveling. You can find out surprising things about yourself while on the road. Your priorities may shift. 

I would track my feelings while journaling and notice if I was feeling bored, numb, and/or anxious for an extended period of time. I would ask myself: Is my current path serving me? Why am I feeling this way? How do I return to a daily state of presence of calm? It helped a ton to speak these feelings into existence, and over the next few days of processing, the answer for what  I I needed would come to me. You will experience some big emotional challenges while away. You’ll have to reckon with yourself and your shortcomings. These difficult periods are not a reason to quit the gap year, but an opportunity to learn more about yourself. (But if you do have a serious reason to end your travels early, then please do what feels right for you)

When I decided to hike the Camino and work on a farm in Japan instead of continuing down through South America, I felt guilty, worried that other people would judge me, judging myself for not planning the itinerary perfectly. 

In the end, nobody batted an eye! It felt scary to switch direction in the moment, but I’m so glad that I did, because these different experiences were exactly what I needed at the time. 

Protect Your Energy

Take time to call friends when you need it!! Despite all the new, exciting faces, it can get lonely out there. I can get pretty stressed about calling a lot of people, so it helped me to block out some time every day while I was visiting home.

My social battery can drain quickly, and by the last few months of the gap year, I noticed how on guard I felt when sharing a space with 6-12 strangers. After one particularly sleepless night, I made the call to switch most of my remaining lodging to private hostel rooms. 

I also tend to be go go go, wanting to fill each day with activity. When you’re traveling full time, this can negatively impact you over time. I noticed that I needed a rest day when my body began to ache from exhaustion, and my mind felt fried. It’s really great to build rest days into your travel. You can do chores, figure out any logistics for the next leg of travel, or simply lie in bed with a great book.

Post Gap Year: Reintegration 

Coaching and Reflection 

A few months before finishing my gap year, I started working with a coach, Alexis Morin. Alexis is an activist and graduate of the Union Theological Seminary. She helps her clients tackle big transitions or build leadership in current roles, by interweaving spirituality/theology, justice, and leadership. 

Over the year, I had collected such a diverse batch of experiences. I wanted help integrating these experiences, connecting the dots. I wanted to uncover the ways I had changed. What were my needs and values? What was I ready to leave behind?

Alexis asked me difficult questions that I’ve never had to answer before. We uncovered areas of myself that I had avoided or ignored for years. This internal work made it much easier to dream up the perfect roles for me moving forward, inside and outside of work. I came back excited to find a job and community groups aligned with the transformed me.

Post Gap Year Blues 

I moved to NYC and found a great job at a climate startup, yet I was still feeling lost, exhausted, and down for several months. Some relationships with friends had drifted while I was away. I wasn’t finding communities that felt right for me.

It really helped to talk to someone else who had recently finished a sabbatical and was having a similar experience, especially because I hadn’t had the space to talk about gap year reflections with friends. I felt guilty talking about these negative feelings when it was such a privilege to be able to travel. We validated each other’s feelings, and we reminded ourselves to take things slowly and be kind to ourselves as we reintegrated into normal life. 

I wrote more about the job search and the post gap year blues here, if you’re curious. Also, I am here for you if you’re going through a similar struggle.

To conclude: make this experience your own experience. Let it challenge you, change you, teach you. Treat this time away from work is a precious gift. You deserve it. 

“It is your road, and yours alone. Others may walk with you, but no one can walk it for you.” 
- Rumi 

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I’ll leave you with some more resources from people who took or are currently taking gap years. If you have any additional recs, let me know, and I’ll add them to the list!

• Heidi Lim wrote an amazing article on making a pivot to a job with purpose. Her advice includes taking time away from work to reset and figure things out.

• Victoria Kirst, my awesome previous CS advisor, is taking a learning-focused career break and writing about her progress here.

• Matt Yao has been tracking his career break in his newsletter Game of One: here, here, and here. He’s coming out with a reflection soon as he hits his one-year mark!

• Another dear friend Kora Kwok has been tracking his ~artist’s journey~ after also leaving Slack, in the form of beautiful essays and Instagram account.

• Carter, a friend I made at a random cafe in Sayulita, is biking from the US to Argentina!! He’s currently in Ecuador. He’s tracking his amazing journey here: https://www.instagram.com/rhoderide?igsh=YzVkODRmOTdmMw==

• Claire and Peter: hilarious couple on TikTok (and everywhere else), who originally were taking one year off, but have since turned it into two. Here’s a helpful interview with their travel advice.

• Leah’s Field Notes: Leah is a vlogger who embarked on a really cool journey living abroad in cities for a month at a time, learning the local languages. She started traveling a bit before I did, and her videos were both inspiring and comforting.

• Sanmao’s Stories of the Sahara, an OG travelogue which I admittedly haven’t read yet, but looks sick.