Overcoming A World Of Rejection: How To

12 August 2021

One week ago tomorrow, I was sitting outside of my apartment balling my eyes out. 10 years into being an entrepreneur, I’m constantly surprised at what does bring me down. Something in my business goes awry pretty much everyday, so I’m used to the ups and downs!

I’ve been rejected so many times along the way that I never feel phased by rejection anymore, but last week I did. It took me 3 days to bounce back from the frustration of how close I was and the inner monologue of how I still “am not good enough” – a monologue every single founder I know goes through like a hamster wheel, over and over again.

100 people can remind you of your success, but until you hit your ultimate goal as an entrepreneur, validation from others never seems as relative as it could be in the moments you feel ultimately defeated.

 The below video is one I frequently re-visit when I’m struggling with not feeling good enough for my own good, or was rejected like I was last week. I encourage you to watch a few moments of it and then scroll down.

In 2017, I was doing TV segments left and right to make a living – in a new city every single week to afford to do anything I wanted to do since I didn’t have anyone giving me any money or support. Blogging was incredibly hard to monetize and Instagram had only just launched, so I found the back door to get paid by brands to go on-air and host TV segments.

The glamour and the excitement on set was nothing to me. I had never been so depressed and lonely. I was in a new city every week, constantly wishing I could stop going on TV to make enough money to just write and talk about what I really wanted to talk about. I’m so content about the fact I didn’t stop pursuing my dreams because I never would’ve known what it would be like to be where I am today: able to simply run my company and start new ones without having to do so many side gigs I didn’t love doing to pay my bills.

Most people finish high school and then go to college, whereas I did the opposite: decided to pursue entrepreneurship and working in entertainment, which I looked at as a means to leading my dream life as long as I didn’t give up. Way easier said than done. AKA, why I started Mentor Match!

What happened prior to the video above: I pitched a show to a super big production company and landed a meeting with the head producer. To call myself naive would be an understatement. Like, of course they weren’t giving me a TV show. Who did I think I was!?

A few days after getting an email back, I found myself in Burbank walking into a meeting that I thought would change my life.

My life changed in a completely different way – I realized I’d never be successful unless I remained persistent and never defeated.

3 years later, I was filming Fearless Everyday on Radio Disney right across from the building I had the meeting with that producer in. Those 3 years were really rough. I left LA, went back to Boston, kept hosting TV segments that were making me deeply depressed, and I’d go back home and spend the rest of my time pursuing my former nonprofit (Media Impact and Navigation for Teens) along with this blog.

Last week wasn’t much different. I was in the running for a huge show on a major streaming platform (a social media show) with ongoing calls for 6 months with producers and directors. 3 days before my unfortunate rejection, I had even given my passport info, ready to get the call last Friday that I’d be flying to England tomorrow to start filming. I wasn’t chosen. That sucked because I was so close.

Here’s what I remembered about rejection: success isn’t supposed to come easy. If it was, we’d all be founding companies like Amazon and selling our companies for millions. Easy, right?

I was on a call yesterday with the New York Times, and the writer asked me how I pick myself back up time and time again and still remain as passionate about what I do. I’m not certain there’s a straightforward answer to that question, but all I can really say is what other choice do I have? Give up because someone thought I’m not good enough? Heck, I had a show for a year and was constantly told there I wasn’t good enough because I didn’t have millions of followers, yet.

Fuck that.

Were you really that passionate about something if you’re willing to give up that easy?


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