My favorite part was this infographic below.

I think it perfectly illustrates the reality that most things in life are seldom a linear process. It’s usually messy, complicated, and full of winding roads. Posting this here as a simple reminder to be aware of the difference between expectation and reality, and to embrace the struggle that comes with creating anything great.

The Creative Process was originally published in Steve Wu on Medium, where people are continuing the conversation by highlighting and responding to this story.

“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.

Phase 1: Exploration

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.

Phase 2: Travel

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.

Phase 3: Startup Research

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.

Phase 4: Job Recruiting

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:

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.

I thought quitting my job and embarking on this journey would change my entire path in life, but it ended up being closer to a 13-month detour.

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

If you enjoyed my article, it would mean the world to me if you hit the clap button or shared it.

The Most Important Question of My Life was originally published in Steve Wu on Medium, where people are continuing the conversation by highlighting and responding to this story.

I distinctly remember staring into the mirror at age 15, wondering what life would be like in ten years. What type of career did I choose? Was I happy with my job? What city am I living in? There were so many unknowns. I had no idea what the next ten years would bring and how they would shape my life.

I remember that moment like it was yesterday, and here I am — 12 years later — wondering what 15-year old Steve would think about how things ended up. Would he be proud? Disappointed? I’m still not sure of the answer. However, he’d certainly be surprised to discover that five years into my working career, I’d make the decision to leave my job without anything lined up.

So why this? And why now?

Looking back at my career, I made two critical decisions which led me to where I am today:

1. For my first job, I spent ten months as an Investment Banking Analyst at Moelis. There, I learned the importance of doing work that makes you happy, so I left early in search of a job that would bring me happiness.
2. In my second job, I spent 2.5 years as a Product Manager at Scopely. During my time at Scopely, I realized that there’s more to life than just being happy, so I eventually left in search of an opportunity that would bring me fulfillment.

My search for fulfillment ultimately led me to San Francisco, where I joined Ever, an early-stage productivity startup. We were a small, scrappy team that was super passionate about helping people rediscover their life’s memories and I took that mission to heart. We tried a ton of things over the following year but despite our best efforts, Ever didn’t work out the way we wanted and the company had to pivot.

The pivot signaled an end to another chapter in my career, but this time I was at peace with the outcome. My experience at Ever taught me first-hand that the benefits of pursuing a fulfilling life existed both in doing fulfilling work and also in embracing the journey it takes to get there. Sometimes things don’t work out, and that’s okay. Life has many uncertainties, but I’ve found the greatest joy and peace of mind in being true to the process of finding my loves and testing my loves. To me, this is living a fulfilling life.

After Ever, I moved to a Founder-in-Residence role at Atomic Labs, the venture studio that incubated Ever. I stayed for ten months before transitioning out of Atomic to explore new ideas and projects on my own, a decision based on something that felt right in my heart and I decided to run with it.

Steve Jobs describes this process of 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

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. Eventually, by the end of my time at Atomic, it seemed like the only logical choice I could make.

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? I’m fortunate to be able to support myself temporarily without a paycheck, and I want to make the most of this opportunity. I’m hoping to start by spending more time reading, traveling, meeting new people and exploring my curiosities about how the world works and how technology can help people live better lives.

I’ll be the first to admit that I’m nervous, scared and excited all at the same time, but I’m trusting my heart on this one. I have no idea where this journey will lead, but I can’t wait to look back and see how this dot ends up connecting with the rest in the future.

As I embark on this next chapter of my life, I’m reminded of the following words by F. Scott Fitzgerald:

For what it’s worth: it’s never too late or, in my case, too early to be whoever you want to be. There’s no time limit, stop whenever you want. You can change or stay the same, there are no rules to this thing. We can make the best or the worst of it. I hope you make the best of it. And I hope you see things that startle you. I hope you feel things you never felt before. I hope you meet people with a different point of view. I hope you live a life you’re proud of. If you find that you’re not, I hope you have the courage to start all over again

******************

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

If you enjoyed my article, it would mean the world to me if you hit the clap button or shared it.

*Originally published on LinkedIn

Making The Decision To Explore On My Own was originally published in Steve Wu on Medium, where people are continuing the conversation by highlighting and responding to this story.

I was lucky — I graduated from UCLA and landed my dream job at Moelis, one of the top investment banks in the country. I stayed for exactly 10 months before quitting. The biggest lesson I learned from this experience was:

Don’t settle until you find something that makes you happy. In the end, that’s all that really matters

Despite my brief tenure, I left Moelis with a much better understanding of my core values. I learned to value happiness over money. I learned to value passion over prestige. I learned to value my time and how I spent it, both personally and professionally. And most importantly, I learned how to make decisions based upon these values. It took me 10 months in the real word but I finally figured it out. Simply put, I wanted my next job to be something that made me happy.

Fortunately, I was able to land a Product Manager role at Scopely, a venture backed mobile gaming startup. I was passionate about the product and the company was experiencing rocketship growth. It had everything I wanted and I spent my time in a role that challenged me, allowed me to grow and truly made me happy.

I worked at Scopely for the next two and a half years before finally making the decision to leave. It was a strange, unexpected feeling. I never really planned to quit because, unlike my first job, I was actually still happy. The work was interesting, my team was amazing, Scopely was exploding with growth and I was even up for promotion. Wasn’t this what I always wanted? Isn’t happiness all that matters? So why did I leave a job that finally made me happy?

Looking back, I left Scopely because I realized there’s more to life than just being happy. It’s not that happiness isn’t important. It’s just not the only thing, or even the most important thing. I started thinking about what I really wanted out of life and oddly enough, being happy every day just wasn’t cutting it. I was planning my career with a short-term focus on what made me happy, and in doing so, I completely overlooked the long-term importance of living a rich and fulfilling life.

David Brooks, a columnist for the New York Times, describes a fulfilling life as:

The process of finding your loves and testing your loves. All of us love certain things: certain friends, certain dreams, certain professional goals. But you really don’t know the nature of your love until you’ve tested it with reality

He also shares his own life experience, saying:

After ten years, I could write out a priority list on a piece of paper of the things I loved, and I could rank them and I could devote my best energies to my highest loves…When you have the ability to write that list in order, you’ve achieved your agency moment. You have your own criteria. You’re not relying on the opinions of others. Your own standard and your own ability to judge your own life

I didn’t want to just be happy. I had confused happiness with long-term fulfillment, contentment, satisfaction and achievement. I wanted to reach my agency moment and I knew I would never get there if I made every decision using happiness as a barometer for success. There are a ton of things I could do, both personally and professionally, that made me happy, but relatively few would meaningfully contribute to a more rich and fulfilling life. I knew what my next 12+ months at Scopely were going to look like and I simply wanted a change, something that would test my loves and take me on a completely different life adventure.

After leaving Scopely, I decided to move to SF and join the product team at Ever, an early-stage productivity startup. I’m not sure where this will lead and I certainly don’t expect to be happy 100% of the time, but that’s okay. I’m embracing a new city, new job, new industry and new challenges. I’m embracing being uncomfortable. I’m embracing the belief that, regardless of what happens, this will be a brand new adventure and that’s all that truly matters.

I challenge you to focus less on what makes you happy or comfortable and more on what actions you can take to live a more rich and fulfilling life. I’m not saying everything in life has to be deeply thought out, but for the important things — like career goals, relationships, aspirations and fears — it helps to put things in context of what truly matters. Nothing in life will make you happy 100% of the time, and it shouldn’t have to. More often than not, happiness will be a natural side effect of living a rich and fulfilling life because it will give you the satisfaction of knowing you made the most of your limited time here. Happiness is overrated…At the end of the day, you’ll look back on life and appreciate the entire journey, the ups and the downs that shape who you are and the commitments you’re willing to make.

As Mark Twain says:

Life is short…Twenty years from now you will be more disappointed by the things you didn’t do than by the ones you did. So throw off the bowlines. Sail away from the safe harbor. Catch the trade winds in your sails. Explore. Dream. Discover

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

If you enjoyed my article, it would mean the world to me if you hit the clap button or shared it.

*Originally published on LinkedIn

Why Happiness Is Overrated was originally published in Steve Wu on Medium, where people are continuing the conversation by highlighting and responding to this story.

I was lucky — I graduated from UCLA and landed one of my dream jobs. I still remember the day I got my offer from Moelis, one of the top investment banks in the country, asking me to join as a full time analyst. It was one of the best days of my life and I literally couldn’t stop smiling for about a week. I was sold on the investment banking career path — challenging, steep learning curve, being the best of the best — and I worked my ass off to get the job. The hours upon hours of studying, mock interviews and informational coffees finally paid off and at 22 years old I had a six figure salary and seemingly endless opportunities. I started my first day at Moelis ready to take on the world.

10 months later I decided to quit my job, something I never imagined would happen in my two year stint as an analyst. So what happened and why did I quit a job I worked so incredibly hard to get?

I initially joined Moelis for the challenge, steep learning curve and prestigious career path. 10 months later the work was still challenging, I was still learning and people were hitting me up left and right asking for advice on how to break into Investment Banking. I just closed my third deal and our analyst class was a close-knit group. This was exactly where I wanted to be and yet I simply wasn’t happy. Looking back, I was unhappy mainly because I chose my job based on a career path that would set me up for success, and in doing so, I completely overlooked the importance of doing what I believed was great work.

Steve Jobs defines “great work” in this excerpt below:

You’ve got to find what you love. And that is as true for your work as it is for your lovers. Your work is going to fill a large part of your life, and the only way to be truly satisfied is to do what you believe is great work. And the only way to do great work is to love what you do. If you haven’t found it yet, keep looking. Don’t settle.

I quit my job at Moelis because I was searching for a feeling that I knew I would never be able to get if I stayed in Investment Banking. There’s no point in prolonging a job you don’t enjoy when you could be spending your time doing something you do. It’s a cliché, but life is too short to live any differently. After leaving Moelis, I decided to take a Product Manager position at Scopely, a venture backed mobile gaming startup. I’ve always had a strong interest in gaming and this provided me with an opportunity to get hands on with a product that I truly enjoy. Have I found what I absolutely love to do? Hard to say, but this is definitely a step in the right direction and I can’t wait for what’s coming next.

I challenge each and every one of you to discover what you enjoy and go after a career path that allows you to accomplish truly great work. Put less emphasis on what people tell you are “typical career paths”, the “most prestigious jobs” or “jobs that attract the best talent” and go after what makes you happy.

This is much easier said than done and will likely require extensive research, work experience, talking to peers, etc. but no amount of prestige or money will be able to replace the feeling you get when you work on something you love. Keep looking and don’t settle until you find what makes you happy. In the end, that’s all that really matters.

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Things to think about when choosing the right company / career path:

• People: Is this a great team of people you will love working with in the trenches?
• Product: Is this a product-focused company that wants to build amazing experiences?
• Passion: Do I feel passionate about this product to commit all my energy?
• Potential: Is there the potential to create significant impact?
• Position: Will this position leverage my expertise and open new opportunities?

I will only work for companies I admire, with people who inspire me and on endeavors that have a meaningful impact

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

If you enjoyed my article, it would mean the world to me if you hit the clap button or shared it.

*Originally published on LinkedIn

Why I Decided to Quit Investment Banking and Join a Startup was originally published in Steve Wu on Medium, where people are continuing the conversation by highlighting and responding to this story.