Three Gifts For A 20-Something, The Power of Conviction

What three “gifts” would you give a 20-something if you were a “Forty-Godmother”? Here 40-somethings share three wishes to help a 20-something get a head start on the confidence to make decisions that are right for them (not their parents, friends, teachers or society). No more woulda, coulda, shoulda. 

This week’s three wishes are inspired by some amazing women I saw speak this week at the Vanity Fair Founder’s Fair: Christine Humsicker CEO and founder of subscription clothing and retail technology company, Gwynnie Bee; Jaymee Messler, cofounder and president of The Players Tribune, the platform for athlete’s stories that she created with Derek Jeter; and Whitney Wolfe Herd, CEO and founder of Bumble.

Be prepared, don’t be intimidated. 

We are all just people who have good and bad days and mornings that get off to a bad start. We are just people trying to do our own jobs. –Christine Humsicker

Christine was talking about pitching VCs, but remember in any situation, that we all have been there on the other side. And we all come into meetings with a lot more in our minds than just you. Know your shit but remember that it’s just another person you are talking to across the table.

Believe in what you believe in. 

“Something I’ve really learned over the past three years is that it’s conviction over consensus.” -Jaymee Messler, cofounder, president of The Players Tribune

Jaymee was responding to a question from moderator Tamron Hall about whether she had a mantra that kept her pushing when she went into a room and felt like an underdog. In her 18-year career in sports management she was often mistaken for an assistant. saying, “When I was in my twenties, everywhere I went they thought I was the girlfriend or the entourage. In my thirties, I was seen as an assistant. The president of the agency had to call ahead of meetings [to say I was the lead not the assistant] so I would get respect.”

In any decision you make, you get all the best info you can but then you have to do with what feels right to you. She went on to say, “Believe in what you believe in. You don’t always have to listen to everyone else’s opinion if you really feel strongly about it. Not everyone else knows.”

Just say no. 

No. I didn’t realize how powerful it is as a woman to say that word.  Trying to please all, pleases no on. – Whitney Wolfe Herd, founder and CEO of Bumble

When we are younger, we hunger for the yes. To get invited to the table. We say yes! But after a while we learn that we also have to learn the power of no. That is the real power. Whitney admitted she was always a people pleaser. “I wanted to make everyone happy at all times,” she said. It wasn’t until she found herself mentoring other women to say no that she realized she needed to stop saying no as well. “I forced myself to say no. It took mentoring others on this to mentor myself.” She encouraged all women to not feel guilty saying no.


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