The Dumbest Smart Decisions I Ever Made

What’s the best that could happen?

Let me tell you something: I’ve made some decisions in my life that, at the time, seemed downright idiotic. But here’s the kicker—they turned out to be brilliant.

Quit Law School

In the late seventies (19 not 18), Asian American kids were supposed to go into one of three professions: doctor, dentist, or lawyer. In my freshman year of college, I took a one-credit class that involved going on rounds at the medical school.

I fainted on the first day. That was the end of medicine. Then I learned that dentists have a high rate of suicide, so dentistry was out too. That left law and that seemed like a good idea because my father, though he never went to college, was a state senator in Hawaii.

He would love it if I became a lawyer, so off to law school I went in 1977. After a week of orientation, I decided I just hated law school. I was totally intimidated by the case study method. So much so that I quit law school shortly thereafter. I never even went to one class.

Sell Fine Jewelry

Before Apple, I worked for a fine jewelry manufacturing company called Nova Stylings. My job was to sell gold and silver fine jewelry to retailers. Let me tell you, the jewelry business is brutal—much tougher than the tech industry. I spent my days schlepping samples, dealing with skeptical buyers, and learning how to close a deal.

I started at Nova while I was getting my MBA, and then when my friends went to work for banks and consulting firms, I stuck with Nova. But looking back, it was one of the most valuable experiences of my life. It taught me how to sell, how to handle rejection, and how to build relationships. Those lessons became the foundation for my career in tech and beyond.

Sign On with Canva

Fast forward to 2014. I was 59 years old, and most people my age were thinking about retirement. That’s when Melanie Perkins, the co-founder of Canva, reached out to me. Canva was a tiny Australian startup with big dreams of democratizing design. But there was this other company named Adobe.

And how hard would it be for Adobe to make a simple version of Photoshop and put it online?

But then I saw the product and adored Melanie, Cliff, and Zach, and I realized Canva wasn’t just a tool—it was a movement. It made design accessible to everyone, from students to small business owners. So, I took the leap and became Canva’s chief evangelist. Today, Canva is valued at over $40 billion, and I’m proud to have played a part in its success.

Embrace “Foolish” Decisions

Here’s the moral of the story: sometimes, the decisions that seem foolish are the ones that lead to the most growth. They push you out of your comfort zone, force you to take risks, and open doors you didn’t even know existed.

So, the next time you’re faced with a decision that feels risky, unconventional, or unpopular, ask yourself: what’s the worst that could happen? And more importantly, what’s the best that could happen?

To hear these stories in depth, preorder my new book Wiser Guy.

Share Your Story

What’s a decision you made that seemed foolish at the time but turned out to be brilliant? Reply and share your story—I’d love to hear it!

CTA: If you enjoyed this newsletter, share it with someone who needs a little encouragement to take a leap of faith. Let’s inspire more “foolish” brilliance together.

Mahalo!

Guy