When Did You Take Your Last Leap of Faith?

In September 1991 I took one of my life’s biggest leaps of faith.

Kyle Okimoto
2 min readJul 31, 2023

I left the comfort of my business school program in Chicago. And I took a year off to attend a program in Leuven, Belgium. I met incredible people and built indelible memories. The experience was so valuable to my classmates that we return every 5 years from every corner of the world to hold an unofficial reunion.

I was reflecting on various leaps of faith over my life. Here area few of them:

Moved away to go to college: I attended university 4000 miles away from my hometown of Honolulu.

Pushed forward to marry my wife despite her parents’ objections: my wife parents disowned her for 2 years due to our relationship.

Made a big career switch: Left the comfort of a stable marketing job to the unknown world of management consulting.

Had kids: we struggled through infertility treatments for several years and finally were able to have two daughters.

Taking the Ship 30 for 30 writing class: publishing every essay and attending every breakout session is so scary for me.

Here’s the funny thing about all of these leaps of faith.

I’ve never regretted any of them.

If there’s any regret I wish I had taken more.

The next leap will be to figure out how to build on my writing and translating it to something bigger.

Let’s get there together!

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Kyle Okimoto
Kyle Okimoto

Written by Kyle Okimoto

I empower business owners to jumpstart growth | CMO & Head of Transformation @etrade @MerrillLynch | 4 Boston Marathons | Northwestern Wildcat fan

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