Be YOUR hammer and look for YOUR nail

One of my worst moments as a start-up CEO was when I lost $400,000.

The short of it is that a customer had sent us the money, but my company was too small to receive such a large payment. And due to technical reasons, our payment processor could not refund him.

In a kafkaesque twist, that money was stuck in limbo.

My customer was pissed – and understandably so. I felt just awful about it. 

I bore the brunt of his fury. A torrent of angry calls and ALL CAPS emails poured in. He looped in his lawyer, and legal action loomed large.

I always knew that there was a chance that my start-up could fail – but I had never imagined it would happen like this . . .

Thankfully, after 2 of the most stressful weeks of my career, I solved the issue.

Whether or not you are a start-up founder, the following sentiments may resonate:

Your career is going well. You feel young and energetic. The world is your oyster. 

Suddenly, you experience a small setback. And your perspective changes. You zoom in on the negative. You feel a bit lost. You start doubting yourself.

“Am I on the right path?”

I’ve felt this way before. The $400,000 near-disaster is a dramatic example, but throughout life I’ve constantly felt doubt.  And from conversations with some of my closest friends, I know that my experience is universal.

Perhaps you feel lost at this very moment.

My previous article discussed how investors and entrepreneurs should avoid the hammer looking for a nail mistake. But for your personal career, I advise the exact opposite—you should embrace your inner hammer and look for your nail.

“Yishi, why are you telling me two different things?”

The reason comes down to the amount of effort required.

It’s hard to fundamentally change who you are as a person–much harder than becoming a better entrepreneur or investor.

You’ve made it this far in your career. You must have done something right! You are the solution to your challenges. You’ve invested the past few decades of your life building that solution. 

So look for problems that you are well suited to solve based on your strengths. Don’t just be any hammer looking for any nail. Be YOUR hammer and look for YOUR nail.

“How do I discover what my hammer is?”

David Cohen, the founder of Techstars, once answered this question for me with 2 specific pieces of advice:

  • Find a coach
  • Do 360 reviews

I’ve embraced both tactics myself, and they have been very helpful.

Now at Optionality Partners, my start-up studio, I try to coach others from the very beginning.

For example, my favorite question to ask prospective business partners is: “What do you think you are better at relative to your peers?”

It’s a twist to the classic: “What are your strengths?” question, but much more thought provoking.

Importantly, I ask you to think about your peers. The peer group that you compare yourself to is telling. From that emerges an existential question: “What do you want out of life?”

That can certainly be uncomfortable to think about. And that discomfort is healthy.

Overall, I’m asking you to go a level deeper, to consider your strengths not in a vacuum but in a relative context. 

These aren’t easy questions to answer, and I’m not trying to trip you up. I’m trying to help you figure yourself out. There is no perfect answer. Any genuine response will evolve over time, and it’s a life-long learning process for all of us.

Most likely, your core strength is a unique combination of assets that few others have.

For example, Scott Adams was an unexceptional artist and unexceptional comedian. He worked a few unremarkable stints at unremarkable white-collar jobs in the 80s.

Scott ultimately fused his mediocre skills and life experiences to create a powerful hammer—the highly successful comic strip Dilbert. (Due to his political views, he is a highly controversial character today. His autobiography is worth a read.) 

So look for that magical, irreplicable combination in your own life.

And whether or not you consider yourself to be an entrepreneur, let’s help each other find our hammer and our nails. Start by signing up for my newsletter below!

I write at the intersection of investing, entrepreneurship and personal growth. Contact me at I respond to all thoughtful messages.

Thank you Steven Ovadia and others for reviewing previous drafts of this article!

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March 25th, 2021

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