165: 🛫 Taking the Leap

165: 🛫 Taking the Leap

Newsletter

A story of emotional courage: how I opened up my heart after a difficult breakup to date and eventually marry the person of my dreams.


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Cultivating Resilience is a weekly newsletter about rebounding from setbacks and reinventing the future—by 3x founder and executive coach Jason Shen.

This week's issue is another story about courage, this time emotional courage. It's about how I took the leap and asked out the woman who would eventually become my wife. There's of course the neat and tidy NYTimes version: "He Took the Leap First, Bad Knees and All", but you all get the more honest and reflective version.


They say you shouldn't date friends, colleagues, or project collaborators. "Don't shit where you eat" is one variation on this idea—one I've always hated for its crassness and because fundamentally, I don't think it's reasonable advice.

I believe some of the deepest relationships are formed through work. Collaborative work enables people to pursue shared goals, rely on one another, and come together to solve difficult problems.

Still the advice is shared because it can be risky to date someone who you have some other existing relationship with, because it can lead you to lose any relationship you have with them should things go wrong. And that's where we begin our story:

Amanda and I met at the offices of Percolate as members of the marketing team. I was on content, she was on design.

The couple met in the fall of 2014 as co-workers in the marketing department of a software company in Manhattan. She initially saw him as a “dumb jock,” and “wrote him off,” she said, “as someone not worth getting to know.”

But her impression of him changed when they were asked to lead a promotional campaign for the company and she discovered he had lots of great ideas.

“I knew he was good-looking, but he absolutely surprised me with his intellect,” Ms. Phingbodhipakkiya said. “He was someone who could brainstorm and turn out ideas like magic, he was just brilliant that way.”

I had been dating someone else at the time, someone I felt strongly enough about that I essentially moved in within the first few months, keeping just a tiny 7' x 7' room in East Williamsburg as a backup. Amanda saw me commute 70+ mins each day to be with this person and was both impressed and a bit miffed.

When that relationship ended in a bad way that summer, I was hurt, frustrated, and swore off serious dating for at least five years. I told our mutual friend Sandy that I was going to "start a new company, make a bunch of money, and only then start dating again in my mid thirties."

We all have an instinct to protect the things that are precious to you, and one's heart might be the most precious thing of all. I was a knight who had been wounded on the battlefield of love, and was now hiding out in the forge, assembling a massive coat of armor before my next encounter. That unfortunately doesn't work in the real world.

It was my friend's wedding that really weakened this plan. I was a groomsmen and reflecting on how I had seen my friend through many special someone's in his life, and yet he had found someone who he wanted to spend the rest of his days with, and the cracks in my plan were starting to reveal themselves. Sandy saw an opening and prevailed on me the limited window where something might happen between Amanda and I.

I was afraid of dating, of commitment, because the last time I had gone for it, I had nothing to show for myself. I had put all this time, emotional labor, and reputation capital into the relationship and wound up with nothing. What a waste. What if it happened again?

I was afraid. But as we've discussed, courage is not the absence of fear, but feeling the fear and doing it anyway. I told myself that I would be vigilant and self-aware. I would not go in guarded and wary—never a recipe for a great relationship—but I would monitor the circumstances closely. And if the relationship did not seem to be headed down the right track, I would pull the ripcord and bail.

In October 2015, a year after meeting — each had since moved on to other jobs — their journey crossed the line from friendship to relationship in a single kiss initiated by Mr. Shen in front of a restaurant on the Lower East Side.

“It’s always scary to make that leap, but I just put it in my mind that I was going to go for it, and I did,” he said. “She responded pretty well to my kiss, which was a great sign.”

They became serious and moved into an apartment together in September 2016.

“I found her to be a great collaborator not only at work but in life,” Mr. Shen said. “She has a lot of ambition, as I do, and we are both able to pursue individual dreams without taking over each other’s lives.”

Next April will be the 5th anniversary of our marriage. I am writing this letter from a hotel in Bangkok where Amanda is working on a large-scale textile installation that uplifts community voices and celebrates US-Thai relations. We had an evening full of stories, laughter, and project collaboration while enjoying hot pot and dessert at one of Thailand's many luxury malls.

Taking emotional and romantic risks is uncomfortable, but the rewards can be wonderful indeed.

—Jason


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