I Was Looking for a Startup Idea. I Needed to Ask a Different Question

In March, I left Artie (YC S23), where I’d helped build the company from seed through Series A, to start something of my own. A couple of months later, I found myself working on an idea I wasn’t particularly excited about.

The idea was in investment banking, an industry I’d spent several years in before joining Artie. I knew the users, understood their problems, and could get meetings with the right decision-makers. I spoke with 18 banks, built prototypes, and even had a potential pivot in mind. (I wrote more about the project here)

But I hadn’t stopped to ask myself a more basic question: did I actually want to spend the next several years working on this problem or this space?

After leaving Artie, I’d spent about two weeks exploring ideas before I started feeling anxious about the lack of progress. I’d wanted to start a company for a decade. Now that I’d finally taken the leap, I wanted to get going. Finding a problem in an industry I knew felt better than continuing to search for something I couldn’t yet articulate.

So I ran with it. I could explain why the idea made sense, and a handful of people around me agreed it was worth pursuing. That was enough to convince myself to get started.

Looking back, I had a good reason to pursue the idea. I just hadn’t established that I wanted to.

I’ve always worked toward something

I’ve spent much of my life taking on difficult things because I could see what they might lead to.

I studied hard in school because I was curious, and because I knew it would open doors. During my two years of military service in Korea, I saw it as both a worthwhile experience and a way to keep my options open. I could have chosen not to serve, but doing so would have restricted how long I could stay in Korea and whether I could work there. Completing my service meant I could return to the West and continue building a life there without those restrictions hanging over me. Later, I went into investment banking with a similar mindset.

Banking wasn’t necessarily where I wanted to spend my career. I wanted to understand how successfully scaled companies position themselves in the market, how they grow and compete, and how different strategies play out across industries. Working on mergers and acquisitions gave me exposure to these companies.

The work was demanding, but I had a reason why I was doing it. I was willing to put in the effort because I believed the learnings would be valuable for ultimately starting a company.

Eventually, I wanted to stop learning about companies from the outside and help build one myself.

That’s why I joined Artie as its first business hire. I wanted the operating experience I thought would prepare me to start a company of my own. I’d also be lying if I said fear played no part in the decision. I didn’t have an idea I believed in, and I had built up an image of founders as people who somehow knew what they were doing before they started.

Working alongside founders quickly changed that view. They didn’t have everything figured out either. They had a strong bias toward action, made decisions with incomplete information, and improved through iteration. Watching that process gave me a better understanding of how companies get built, and more confidence that I could do it myself. I didn’t need a perfect idea or a complete plan. I needed to get started.

I stayed at Artie for nearly two years. The work was demanding, and most of my attention went toward building the business. I sometimes wondered whether I was doing enough to prepare for starting my own company, but I kept telling myself that the experience I was gaining would help me get there.

Eventually, I decided to leave and give myself the time and space to figure out what to build. I thought the problem had been time. Funnily enough, when I finally had all of it, I spent it much the same way.

When becoming a founder became the goal

I’d wanted to start a company for more than a decade, for a few reasons.

I’m drawn to the personal growth that comes from taking on something difficult and being responsible for making it work. I want greater ownership over my time, decisions, and the direction of my life. I also want to build alongside talented, driven people who share my interests or care about the same mission.

And I want to build wealth. I believe in focusing on the inputs, doing the work well, and letting the results speak for themselves. Strong results create credibility over time, and credibility makes it possible to have a greater influence on the people and problems that matter to me.

Starting a company seems like a way to pursue all of these things at once.

The trouble was that I’d become so focused on starting that I’d stopped giving enough thought to what I was starting.

The investment banking idea was a natural candidate because of my background. My experience gave me an advantage in understanding the customer, and I knew how to get in front of potential buyers. But none of that automatically meant I wanted to build for them.

I’d learned at Artie that you don’t need to have everything figured out before taking action. That lesson was important, but I’d taken it too far. I treated the uncertainty around what to build as something to overcome quickly, rather than a question worth spending time on.

I don’t think the investment banking idea itself was necessarily bad. It might have become a good business. The problem was that I hadn’t given myself enough time to understand whether the industry, the problem, and the work involved were things I wanted to commit to.

I was evaluating opportunities based on whether I could build them, rather than whether I wanted to.

I kept searching, but in the same way

After moving on from the banking idea, I spent another three months exploring other opportunities.

I looked at problems in US healthcare, and launched a golf app that I wanted to use with my friends. I explored other ideas, too, talking to potential customers, testing assumptions, and building things along the way.

In many ways, I was doing what I’d learned to do at Artie. Rather than sitting around waiting for inspiration, I was getting out into the world, learning about problems, and testing whether they were worth solving.

But I began to notice a pattern.

Each idea became another sprint. I’d identify a problem, investigate it, and try to work out whether it could become a business. When an idea didn’t feel right, I’d move on to the next one.

I was making progress on individual ideas, but I wasn’t necessarily getting closer to understanding what I wanted to build.

I’d left Artie to make room to think and explore. Yet I’d filled that room with sprints.

Effort was the part I knew how to supply. I’d spent years learning how to work toward a goal, stay disciplined through difficult periods, and make progress even when things were uncertain.

What I hadn’t learned was how to slow down when more effort wasn’t the answer.

I was still treating the search for an idea as a problem to solve as quickly as possible. I hadn’t given myself much space to consider what I actually cared about, what kinds of problems I’d be happy thinking about for years, or what work I’d find rewarding in its own right.

Those questions were harder to answer than whether a particular problem had a market or whether I could build a product to address it. They also couldn’t be answered by running another sprint.

By August, I decided to pause.

What I want to spend my time building

With the constant pressure to find an idea temporarily removed, I started thinking about the kinds of things I’ve consistently found rewarding.

Some of the experiences that come to mind aren’t particularly grand. They’ve involved helping Korean students find their footing abroad, athletes find their place on a team, and friends and students navigate career decisions, whether breaking into banking or making the transition into startups. I’ve often found myself spending hours talking through someone’s options, helping them make sense of a difficult situation, or figuring out what to do next. I enjoy those conversations.

I don’t take this to mean that my next company needs to be about helping people in some direct or obvious way. Nor does enjoying these experiences automatically translate into a business idea. But it’s a pattern worth paying attention to when I’m trying to understand what kind of work I’d find rewarding enough to pursue for years.

It also reminds me that I don’t need to manufacture enthusiasm for a problem simply because I can make a convincing argument for why I should work on it. I should give more weight to the problems I’m naturally curious about, the people whose challenges I want to understand, and the work I find myself returning to without having to force it.

Paul Graham famously advised aspiring founders not to try to think of startup ideas, but to look for problems, preferably ones they have themselves. I’d known that advice for years. Yet I’d spent months looking for problems to turn into companies.

In retrospect, I was following the first half of the advice and skipping the second. I was looking for problems I could make a convincing case for solving, rather than paying enough attention to the problems I was genuinely drawn to.

Choosing what comes next

I still want to start a company. I still want the challenge, the autonomy, the opportunity to build with people I admire, and the possibility of creating something that delivers outstanding results.

What I’d do differently is give myself more time to choose what to work on before committing to it.

That means protecting time to explore ideas, speaking with people who might eventually build alongside me, and paying attention to the problems I find genuinely interesting. It also means asking myself whether I want to do the actual work involved in an opportunity, rather than focusing primarily on where pursuing it might lead.

I don’t expect this to guarantee I make the right decision. Starting a company will always involve uncertainty, and some things can only be learned by doing. But I can be more deliberate about which uncertainties I try to resolve before taking the leap.

For years, I’d measured progress by how much closer I was getting to starting a company. I hadn’t spent enough time figuring out what I actually wanted that company to be.

I still care about the destination. I just want to be more thoughtful about the journey that gets me there.