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Can you ever turn off the entrepreneurial mindset? And how being nice cost me a promotion

Happy Thursday, almost Friday!

We are busy interviewing more Fil Am entrepreneurs but thought you might want to hear about how Tricia’s entrepreneurial mindset prompted a memorable conversation on the subway.

Can you ever turn off that entrepreneurial mindset?

New York, NY, 2015- The encounter took place the night I arranged a dinner for a group I’d nickname the “Amiables.”

That sounds like a good thing but it wasn’t. As part of a career development workshop, my managers and colleagues had been given an exhaustive questionnaire meant to pinpoint each of our styles of working.  The categories were Analytical, Driver, Amiable, and Expressive. I was–as you might have guessed–an Amiable.

I wouldn’t have minded the label so much but at that time, I led a successful global team and had asked  for a promotion. My request was denied. The reason? I was “too nice.”

With my rockstar team members Danika Jensen and Jeff Chou

And so, I had reserved a table for five other Amiables so we could put our niceness aside and vent, but only one person besides me showed up. The two of us had a great time talking about our careers but because the waitstaff was giving us the evil eye, I couldn’t help thinking that the two of us were the losers of the losers, especially since we waited for an hour for the others to show up. By the time I boarded the subway on 23rd Street en route to the tip of Manhattan, I couldn’t wait to get home, go to bed, and forget the day. As soon as I got a seat, I put my headphones on and started reading  the New York Times on my phone.

At Penn Station, 34th Street, a tall, hefty man squeezed next to me and started to ask me questions.

“That’s a big ass phone, what model is it?”

At that time the iPhone plus (6.23 inches) was new. Because of my bad eyesight, I’d purchased it right away.

I pretended not to hear but he persisted.

Finally, I took my headphones off and told him. He said he was going to buy a phone just like mine. And then he proceeded to tell me that he had been in jail for 17 years and was wrongly put in solitary confinement. He had just won a $6 million dollar settlement. He said his lawyer’s fee was $2 million.

With the $4 million he said he was going to buy a phone like mine and then a Bentley.

“It’s a million dollar car, you know.” (I checked later and learned that a base model is about $200,000.)

That plan didn’t seem right to me.  I had grown up with parents who were entrepreneurs, always open to opportunities.

I couldn’t help it–my  whole body turned  toward him and I said— “You have $4 million and you are going to spend a quarter of it on a car?! Why don’t you open a business? What about a restaurant?”

The man’s eyes lit up and he confessed that  he was known for making amazing wings and hamburgers.

“Oooh, they loved how I seasoned my burgers in prison. I can see it… my mom and I will open a burger place. I need to set aside money for the equipment… but first I need to buy her some furniture. I promised to buy her new furniture…I need to hide too because I have five baby mamas and they are all looking for me to give them money…”

I sat and listened. I also asked him why he was in prison.

“Seventeen years because I shot my sister’s attacker 17 times. You can look it all up on Google,” he said. He even gave me the name of his lawyer.

“You have $4 million and you are going to spend a quarter of it on a car?! Why don’t you open a business? “

I think it’s because I am short, only five feet tall, I’m quick to  smile, and many people seem to feel comfortable around me, perhaps because I’m….nice? Whatever the reason, he and I rode stop after stop uptown, and he talked to me like we were old friends.

“What do you think about Atlanta?” he asked. “I’m thinking of moving there.”

I told him I’d been to Atlanta. I listened and was excited for him but I was also scared. I tried to remember his name and the name of the lawyer so I could look it up later but my heart was pounding inside my chest, as I wondered what would happen when I left the train. It was a dark winter evening. I prayed “Please don’t let him follow me home.”

Suddenly, he looked up and saw that we were at 157th Street.

“This is my stop,” he said.

The man took my hands and said to me, “Thank you, you are a beautiful person and I love you!”

When the subway doors closed, an older woman on the other side of me immediately exclaimed, “I heard everything!  I liked how you talked to him; you were patient and kind, you handled that beautifully."

"Do you really think all that was real, that he was in prison for 17 years?,” I asked.

“With his cracked teeth and tattoos he sure looked like it,” she answered.

It’s been years but whenever I pass the 157th Street stop, I remember that conversation. It reminds me that being nice is not just for losers and to keep that entrepreneurial mindset—to be open not just to business opportunities but also to people’s stories.

As for the promotion, eventually, I got it.

Le Cunff introduces many interesting ideas for personal and professional growth. My favorite insight is in the beginning, “The Trap of Linear Goals.” Life is rarely linear. Le Cunff presents different ways of personal and professional experimentation.

The Tutong Newsletter team receives a 10% commission on every sale via Bookshop.org. In addition, if you are in the US, a matching 10% goes to fund your local bookstore.

Special thanks to Paula Derrow for editing this piece.

Thank you for subscribing to the Tutong Newsletter. If you enjoyed this, please share it with someone who might find it valuable.

Tutong is the Tagalog word for toasted rice at the bottom of the pot. Some choose to toss it, others seek it out. Every other Thursday, we feature the story of a Filipino American entrepreneur and how they dug deep to start their own business.

Want to tell us about a Filipino American entrepreneur, sponsor, or give us feedback? Contact us here.

We look forward to hearing from you.

Tricia Capistrano, NYC

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