The Most Important Question of My Life

Steve Wu
Steve Wu
Apr 11, 2020 · 9 min read

“It’s worth recognizing that there is no such thing as an overnight success. The truth is, most of us discover where we are heading when we arrive. At that time, we turn around and say, yes, this is obviously where I was going all along. It’s a good idea to try to enjoy the scenery on the detours, because you’ll probably take a few” — Bill Watterson (creator of Calvin & Hobbes)

I don’t remember the details of everything that happened on July 2, 2018, but I’ll never forget how that day made me feel. It was the last day of my job at Atomic — a venture fund in SF — and I remember feeling a sense of excitement, enthusiasm, nervousness, and doubt. It was a strange mix of emotions, but I knew why today was different. For the first time in my life, I had quit my job with nothing lined up, no plans to find a job anytime soon, and no direction other than a single question I wanted to answer for myself.

At the time, I wrote a short blog post explaining what this question was and why it meant so much to me. To summarize:

“I left without another job waiting because it was the ultimate unexplored dot — an experience I thought would never become part of my story but became more and more of a reality with each passing month, as I increasingly desired freedom of exploration and discovery. More than anything, I wanted to discover where I would end up if I were entirely on my own, without any job or responsibilities. With all the time in the world, where would my interests, skills, passions, and curiosities guide me?”

In my ideal world, I would spend my days reading, traveling, meeting new people, and exploring any curiosities I had about the world. Over time, I’d hone in on a specific idea or problem I felt passionate about and start a company around something I truly believed in. If everything went to plan, I would find a way to do the most meaningful, fulfilling work of my life — whatever that ended up being. I knew this was a low probability outcome, but I now had more free time than ever before and was hopeful that — with enough time — I could figure things out.

I remember that moment like it was yesterday, and here I am — one year and nine months later — reflecting on what I discovered and the lessons I learned. So, with all the time in the world, where did my interests, skills, passions, and curiosities guide me?

Over the following 13 months, I would spend my time in four phases: Exploration, Travel, Startup Research, and Job Recruiting.

I spent my first two months trying to figure out what I cared about in life. I started by reflecting on my experiences more deeply — trying to understand past moments when I felt the most fulfilled, energized, and inspired. While creating a personal website to document and share these moments, I became fascinated by the intersection of identity, expression, and social connection and started researching topics in these areas. I met some incredible people and even explored a few startup ideas during this period, but didn’t feel strongly about anything in particular. By the end of two months, I was spinning my wheels and didn’t know what to do next, so I decided to take a short travel break and pick things up after I got back.

My two-week trip to Hong Kong, Thailand, and Singapore quickly turned into three-months of travel. Since nothing was tying me back to SF, I decided to skip my return flight, book a one-way ticket to Japan, and wing it from there. I spent the next 2.5 months hostel-hopping through 19 cities across three countries (Japan, Bali, and Korea) before finally returning home. Despite my best efforts to live in the present, I often felt guilty for extending my trip instead of returning home to focus on my goal of finding meaningful and fulfilling work. Thankfully, I brought along a few books to read during my travels. One of them, Shantaram, taught me the importance of forgiving myself, surrendering to new environments, and fully embracing every new experience I would have for the remainder of the trip — absent of expectation or guilt.

At this point, I was five months into my exploration year and desperately wanted to work on something that could be my life’s mission. I spent the next three months exploring ideas across different areas (life-coaching, digital therapy, recruiting, people analytics) but never made enough progress to start a company. Looking back, I realized I ended up repeating the same cycle every 2–4 weeks:

  1. Get excited about a new idea. Start researching, ideating, and prototyping.
  2. Reach a point where I start spinning my wheels. Start to question most things.
  3. Eventually, lose interest in the topic or lose confidence in myself (in my ability to find a problem worth solving, create a 10x solution, find a co-founder, etc.), whichever came first. Put existing idea on the back burner.
  4. Discover a new idea. Get excited again. Rinse and repeat.

After repeating this process 4 or 5 times, I felt pretty discouraged. I wasn’t making progress and didn’t want to spend the next 3 months continuing on the same path. I knew I had to make a change, so I decided to take a break from startups and pursue meaningful work within an existing company rather than starting one myself.

I started my job search with high expectations. I wanted to find a company that perfectly aligned with my interests and wouldn’t settle for anything less. After a few weeks of searching, I came across a promising company and got introduced to the CEO. We talked for over an hour, and by the end of our conversation, I was convinced that this company was the one. At the time, I hadn’t applied to any other companies and didn’t have a plan B, so I put everything I had into preparing for this one interview process.

30 days and four rounds of intense interviews later, I was told I didn’t get the job.

I was devastated.

Over time, I had to pick myself back up and accept the harsh reality that waiting for “perfect” wasn’t realistic. I decided to cast a wide net and applied to an additional 30 companies over the following four months, leading to 17 phone screens, 8 onsites, 5 final rounds, and 2 offers. After months of arduous, full-time recruiting and countless rejections, I officially joined Gusto in August 2019, exactly one year and one month after leaving my last job.

If I mapped out my emotional journey throughout this period, it would look something like this:

my emotional rollercoaster

These 13 months were some of the most emotionally challenging periods of my life. As much as I tried to focus on the journey rather than the outcome, I found myself constantly worried about whether or not I was moving in the right direction. During the high points, I felt excited, energized, passionate, focused, and aligned. However, during the low points, I would replace these same emotions with prolonged feelings of fear, anxiety, depression, frustration, and doubt. I knew there would be ups and downs throughout this journey. Still, I had no idea — and was entirely unprepared for — how much it would impact my mental and emotional state.

Looking back, things didn’t exactly go according to plan. To put it bluntly, I quit my startup job, spent eight months exploring, and then found a startup job. I didn’t start a company. I didn’t achieve enlightenment. And I’m still trying to figure out what it means to do the most meaningful and fulfilling work of my life.

As I continue to reflect, I’m reminded of a Steve Jobs quote on decision making, saying:

“You can’t connect the dots looking forward; you can only connect them looking backwards. So you have to trust that the dots will somehow connect in your future. You have to trust in something — your gut, destiny, life, karma, whatever. This approach has never let me down, and it has made all the difference in my life”

It’s easy to feel inspired by this quote when you’re about to make a big, bold decision, but what happens when you complete the journey and things don’t go according to plan? What happens when you look back one year and nine months later and still find it difficult to connect the dots?

Growing up, society taught me the importance of setting goals and connecting the dots looking forward. I eventually discovered you can’t connect the dots looking forward; you can only connect them looking backwards and trust that the dots will somehow connect in the future. I’m now learning that how each dot connects — and the role each decision plays in my life — will change depending on my goals. And because change is constant, I’ll never know the real value of a decision until I reach the end destination. Choices I’ve made in the past that have seemed like detours now make complete sense today, so I can’t get too caught up on connecting the dots or comparing the quality of my decisions with anybody else’s.

I think Calvin put it best…

So, was it worth it? Only time will tell.

But for now, all I know is that I feel different than I did before this journey started. I don’t feel as anxious, I don’t feel as rushed, I don’t feel like I need answers, and I don’t feel like I need to be anywhere other than where I am right now. Of all the emotions I felt during that crazy 13-month period, the main emotion I feel now is gratitude. I’m grateful for the experience, for the privilege to embark on this journey, for the opportunity to experience things the hard way, and for the space to reflect, learn, and move forward.

If I have one piece of advice to give, it would be that if you feel like you’re on a detour or thinking about taking a leap of faith away from what’s “planned” in life, to think deeply about the question(s) you’re trying to answer for yourself. Lean into the journey and make the most of your experience. Don’t worry about how your dots will connect and don’t compare your journey with anybody else’s. You never know what you’ll learn and how this chapter will end up rewriting the rest of your story.

I leave you with one of my favorite quotes about the power of asking questions. After all, this entire journey started from a single question I wanted to answer for myself:

Life is about asking questions. If you think about it, life is just a collection of questions, or at least the ones we choose to acknowledge. Within those questions we choose to acknowledge, we answer them for ourselves because we feel the need to. And in those answers, I believe we find our own meaning, we find our own definition, we find what it is we stand for, and who we are as people. And that’s how we celebrate our individuality

What questions do you want to ask yourself?

Questions? Want to chat? Feel free to connect with me here: stevewu22@gmail.com

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Steve Wu

thoughts and curiosities 💭