A gap year comes to a close

Pains and learnings from the 12 months I took off before starting college

Why I’m writing this:

  1. For myself: I want to document my experience so that I can officially (and finally) “close the loop” on my gap year.
  2. For my friends and family: I hope this update gives you a better idea of how I was during my year off and brings us closer together.
  3. For all others: I want to share my story of taking time off to encourage others to reflect on their options. There are always options.

While some part of me really wants you to believe that my gap year was nothing but glamorous (the same part of me that feels an incessant need to prove to the world that taking time off from school is neither irresponsible nor pointless), the truth is that it was also really hard.

In writing this, I hope to share my full truth. To celebrate what I’ve accomplished and the tremendous amount I’ve learned, while also embracing vulnerability and honestly sharing my struggles.

So here goes 😉


First, this year just by some of the numbers:

  • Traveled to 9 different states and countries, from Croatia to Germany to Colorado, the majority of which I flew to for free. Shared an apartment in Chicago for 3 months with my partner Sally and lived together for the first time in our relationship.
  • Worked 1 job, 2 internships, and 3 side ventures to cover my living expenses. Earned several thousand dollars (!) the majority of which I’ve set aside in savings accounts or retirement accounts, while also maintaining a credit score of ~750 (give or take a few points).
  • Read 41 books (technically 40 books and 1 unpublished manuscript), or about a book every 9 days. My top three: Team of Rivals: The Political Genius of Abraham Lincoln (Most Inspiring), I Will Teach You To Be Rich (Most Practical), and Living With The Seal: 31 Days Training With the Toughest Man on the Planet (Most Entertaining…by far).
  • Lost 17 lbs as a byproduct of gradual changes to my day-to-day lifestyle. Specifically: cooking instead of eating out (saves money too), eating healthier portions, and going rock climbing twice a week.

But the numbers aren’t everything. Here’s what they don’t tell you:

  • Being racked with self-doubt while I drove through Stanford during the move-in day of what would have been my college class of 2021 (to pick up my girlfriend, who was coincidentally doing research there), watching all of my friends pack their bags and leave for college without me, and wondering for a long time whether I could really make this gap year “work.” Yeah. There was a lot of insecurity and uncertainty those first few months.
  • How one of my big goals heading into the gap year (and in part how I sold the idea to my parents) was that I’d win several scholarships and save on tuition. I applied to maybe a dozen scholarships; I won none.
  • Being so mentally consumed by money and how I’d cover my expenses. Fully confronted with the reality of paying for all of my living expenses as a 19-year-old, I was always hyper-concerned with saving money and cutting costs. This lead to me making some rather unconventional choices like: taking home leftover catering from work (originally meant for the dump) and turning it into 10 freezer-ready tupperware meals, asking various Starbucks for their near-expired foods (which they’re obligated to throw away periodically), and raiding local college hackathons for boatloads of free (and often unhealthy) food (from one, I actually got 2 months-worth of nature valley granola bars and soylent).
  • How I was only able to travel because my girlfriend just so happened to be working for United Airlines and was able to bring one other person (me) onto flights as a standby flyer. While it was amazing to travel in this way, I recognize what an absolute privilege it was and how much luck played a role in giving me that opportunity.
  • The fact that I was only able to get my foot into the door for all of my professional opportunities because I happened to know the right person. I worked with my older brother’s company, Orenda, for the longest time. And then it was through people I met through Orenda that I was later introduced to opportunities with the Silicon Valley Organization (a chamber of commerce) and MissionU (an education startup). I tutored students for months, right back at my old neighborhood library, because I wasn’t sure I’d be able to find another paying job.
  • And lastly, seeking therapy for the first time in my life and acknowledging the need in my life to actively manage my mental health. This was really transformational for me.

So, what I’ve learned from my year off:

First, an understanding of the importance of taking care of my mental health

This past year, I went to therapy for the first time. Doing so and subsequently opening up to loved ones has been difficult, but I wish to include it here because it’s been important to me. Two learnings, in particular, have been really personally powerful:

The first is the importance of honoring past experiences. That doesn’t mean that you have to idolize or revere the past, you just have to acknowledge it in its unedited entirety. To acknowledge all that’s there.

The second is on the relationship between suffering and meaning. As it’s put in one of my all-time favorite books, Man’s Search for Meaning, which explains the idea far better than I ever could:

Meaning is possible even in spite of suffering — provided, certainly, that the suffering is unavoidable. If it were avoidable, however, the meaningful thing to do would be to remove its cause, be it psychological, biological or political. To suffer unnecessarily is masochistic rather than heroic.”

I have historically taken pride in my own suffering (seeing it as noble and always meaningful), and that’s proven to be deeply problematic. Aided by therapy and a year away from the humdrum of school, I’ve started the gradual process of unraveling and rewriting that belief.

Second, a clearer understanding of my essential values

I always knew I possessed values. But my ability to articulate those values pretty much ended upon naming them. I’ve since begun to understand what those values actually look like when fully embodied. The two values that I most try to live my life by now:

Intentionality = being deliberate about how I spend my time + being mindful of how I show up as a person and my impact on others + putting the requisite thought into every decision I make (or don’t make).

I’ve learned that being intentional is different from being constantly productive (which I thought I needed to do in high school). With intentionality, I can still choose to do “unproductive” things like playing video games or watching movies so long as my initial intention was to be playful or to entertain myself. But idly scrolling on my phone during a dinner with my family lacks intentionality. Being distracted during a phone call with my partner lacks intentionality. Being reactive in interactions with other people lacks intentionality.

In essence, I want to always investigate and understand the why behind my actions, because it’s my life that is the sum of those actions.

Vulnerability = fully acknowledging (and when appropriate, sharing) my hardships and pain, even if it means knowingly opening myself up to the possibility of hurt or discomfort, because that’s authentic living.

I cared too much about what others thought of me in high school — I wanted to be respected, admired and most of all seen as individualistic — and as a result, I often lefts parts of me behind in interactions. I’ve since seen firsthand that bringing my full self into every moment and embracing vulnerability leads to more authentic connections, less cognitive dissonance, and a sense of living and being “from my core.” Letting vulnerability into my life has deepened, and in some cases, transformed my relationships.

Third, the importance of community

The spaciousness provided to me by this gap year has allowed me to be more present with my family and connect with them on a more human level — especially my parents, who I made an effort to get dinner with (just us) every few weeks and my three brothers, who frequently got breakfast together (without parents) at a similar cadence.

But community is also more than family. From those you live with to those you love, the people you surround myself with matter so, so very much. I didn’t even come close to recognizing this in high school.

Fourth, a much better ability to self-manage

In high school, 90% of the items on my daily to-do list at any given time were assigned to me, or things that I was obligated to do for external reasons. Much of my life revolved around putting out fires, and there was always a clear incentive to do so (social feedback, grades, etc).

During my gap year, however, 90% of the things I did each day I actively chose to do (for example, learning about personal finance). Rarely were there immediate external incentives for me to do anything. Having this level of freedom and control over my life was liberating, but it was also difficult to manage. Experientially learning more about what motivates me and how to effectively self-manage has been empowering and very useful in many areas of my life.

Fifth, a personal understanding of the value of money

Maybe it was growing up with two engineers as parents and never seriously having to consider costs as a kid, or maybe it was rarely having to deal with large expenses in the first place (the first time I had to take the car in for repairs…wow), but I had never truly felt — on a personal level — the value of money and being able to afford things. Until the gap year.

I’ve since set up personal finance infrastructure for myself like budgeting tools, savings accounts, and even some sources of semi-passive income that will continue with me through college. Now, I’m just much more aware of the layers of privilege that exist in my life (socioeconomic being just one of them), and I have a mindset of frugality I don’t think I would have acquired otherwise.

Lastly, learning how to learn

From going through a coding boot camp in Fremont with no teachers and no classrooms (see 42.us.org if interested; it’s free) to reading up on random topics like cryptocurrency (yes — I went through that phase) and seasteading (creating floating ocean cities) to teaching myself how to pick a lock, my biggest learning from this past year is that learning can happen anywhere and at any time, even — or perhaps especially — during a year away from school. I used to think that learning was just one component of the many that form educational institutions like schools. But in reality, it’s the complete opposite. The domain of learning is huge, and your formal schooling is just a tiny, tiny fraction of that.

And as my gap year has shown me, to live is to learn.


In summary, I am not the same person I was at the start of this year; I’d like to believe that I’m more grounded, more whole, and more honest with myself. The Will that would have started college one year ago would have made very different life choices than the Will of today. And that’s all I really could have asked for from a gap year.

I want to close with acknowledgment and profound gratitude for all those who shaped me during my gap year.

To Carl, who didn’t hold back one bit in leveraging his resources to support me (even letting me live with him for nearly a year), and without whom I never would have taken a gap year in the first place.

To Brandon, who showed me the power of investing in people and who single-handedly helped me go from “matcher” to “giver.”

To Norman, who taught me the language of emotions and who has enabled me to feel empowered by all of life — not just its shiny bits.

To Tam, who showed me what it really means to be “full of life” and who opened my eyes to the immense joy of living life to its absolute fullest.

To Cat, who showed me the importance of checking in with the human and who taught me that the little things really do matter.

To Sally, who held me tight through it all (the ugly and the pretty) and who is the most patient, loving partner I could have ever asked for.

To Mom, Dad, Jason, Joseph, who welcomed me home each time I got tired of my own terrible cooking and who wholly supported each and every one of my decisions (even the bad ones).

And to everyone else I met during my gap year…

Without you, this last year would not have even been remotely as transformational to me as it was. And it was really transformational.

So thank you.

Next week, I’ll start my second quarter at Stanford. My first quarter has shown me that although there are things I certainly don’t miss about school — waking up early, always feeling “busy,” people stressing out about grades — I do admittedly really miss having peers, feeling my own age, and being constantly challenged. So it’s been a welcome change, though one I’m most definitely still adjusting to.

To anyone who’s read this far, I truly appreciate you making time to hear my story.

Take care 🙏


PS: One of my resolutions for 2019 is to write a blog post every month. Some topics I’m thinking about:

  • What I’ve learned from reading love and marriage books
  • The 80/20 of personal finance for college students
  • Platonic intimacy and building community
  • Principles and systems for “getting things done”
  • A collection of the best self-reflection activities/exercises I’ve found

If you’re interested in reading what I write, please consider following along via Medium, where I’ll be sharing about all of these (and more).

PPS: Considering taking a gap year? Currently on one? Have a friend in a similar situation? I’d love to connect and maybe even be of support. Please shoot me a message at https://www.facebook.com/wwilliamsshan :)