Connecting with Risk-takers

Last Sunday, I went to a free event in New York City called Conversations New York. Over a hundred strangers came together on a sunny, breezy day in Bryant Park behind the main branch of the New York Public library. All around me, people lounged on the lawn eating lunch, playing ping pong, and reading books and magazines at the outdoor reading room. For the event, tables were set up on a stage, each one signaling a different topic to discuss.

I chose “Risk-taking” because I wanted to meet people who would teach me how to take risks with ease and confidence. The first question was “What do you want more than anything now, but are afraid to go after?” I explained that I wanted to submit my completed novels to agents and not give up so easily this time in the face of rejection. During the course of the conversation I learned some important, and uncomfortable, things about myself.

I started off by revealing my vulnerabilities and insecurities. Isn’t that the way to be instantly liked? I related my fears about submitting my writing. I expressed my doubts about my ability. Then I thought to myself, what is there to be afraid of? Am I as meek as I’m saying? Do I truly have so little confidence?

The people in the circle encouraged me with stories of triumph over rejection. One woman related her life’s journey in a strong, vibrant voice. “I once ran one of the best dancing schools in Manhattan,” she said. “I was great. This is New York after all, and I was heads up better than the rest. Later, I worked in different companies, but as I got older I became a victim of ageism.”

The woman expressed no doubt about her talents and abilities the way I had done. “I dropped everything and moved to California to open my own catering business,” she continued, “because I’m excellent in that field and was doing it in New York. Unfortunately, someone who promised to make introductions for me in California reneged on this promise. I knew I was fabulous.”She laughed. “I had catered parties for famous rap musicians in New York and they loved me. But I failed in California.”

The woman didn’t sound egotistical. She exuded confidence and enthusiasm but also sincerity and humility. I believed in her talents and her abilities because she did. She was someone I wanted to know better.

I began to feel bad that I’d expressed only self-doubt. These were strangers and I had painted an inaccurate portrait of myself. Why would any of them want to know me? I wouldn’t have wanted to know the person I had described myself as. I jumped in to correct my self-description and saw eyes light up with interest and encouragement.

“Actually,” I said, “I know I’m great at what I do also. I’m a wonderful psychotherapist and I have a reputation that has spread throughout the population I serve on Long Island.” As soon as I said this, I felt I was being too strong, so I went back to undercutting myself. “Maybe I’ve been ruined by too much early praise,” I said. “All my writing in school and on jobs has been recognized with awards but sometimes I wonder if people are just being nice and not telling the truth.” Did I believe what I’d just said? No. Then why had I said it?

I think this is a habit that women often have, more than men. We sound self-effacing. We think that if we state our abilities and talents outright we’ll sound like braggarts, and that’s unattractive.

The truth is, I’m not fearful or timid, even though I sometimes feel that way inside. I wished I’d told those people that I took the biggest risk of all when I had a low-paying, part-time job in social work and two children, aged 2 and 5, when I decided to divorce my husband. He had a cash business and reported very little income so I knew my child support would be inadequate.

But by myself, I bought a little house other people told me I wouldn’t be able to support. I was able to. My two sons went to college and law school. They’re successful and happy.

When the discussion ended we left to find conversations to join. I wanted keep in touch with the dynamic woman who recognized that a lot of her difficulties were not of her making. I didn’t take her number. No one else exchanged numbers either. Why not? Were we all afraid of being rejected?

Now I wish I’d given my number to a few of those people. I might have been rejected, but so what? Isn’t that what risk-taking is all about? Besides, it would be such a small risk. Whenever I’ve reached out to other people for friendship in the past, they’ve always welcomed it.

I’m now committing to a new plan to change my life: I’m going to keep going to social activities with strangers. I’m going to exchange numbers with anyone I find interesting. I’m going to follow up later with a phone call and an invitation to get together.

Taking a risk is the only way to connect with people worth knowing. It’s the only way to accomplish anything of value.

2 thoughts on “Connecting with Risk-takers

  1. A lot of truths in here. I too, would rather talk less about my accomplishments lest people think me conceited or a show off. I’d rather people decide for themselves if what I do is good or not – and yes, some people think ‘not’; but I’ve learned to accept not everyone believs and likes the same, so I’m alright with that too.
    Great post and great goals to look forward to.


    1. Thanks for your comment, Jina. Yes, it’s difficult to figure out sometimes where self-confidence ends and bragging begins. I guess there is a way to let someone know our good qualities without sounding conceited, but like you, I’m shy about that.

      Liked by 1 person

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