Alternative Careers: Be Aggressive

B-E A-G-G-R-E-S-S-I-V-E! If there is one piece of advice that has helped in my alternative career transition from lawyer to comedian it’s to always be aggressive. A cool thing happened to me recently because I followed my own advice.

Tell People What You Want

Nobody is sitting around thinking of ways to help Matt Ritter … or you … except maybe your mom. Everyone else is busy. So if you are trying to accomplish something that requires other people to pitch in, just ask. Maybe you can offer something in return so it doesn’t seem like you are imposing.

One good recent example is someone I found right here on Lawyerist. Fellow lawyer turned comic, Alex Barnett. After reading his similar story, I reached out to him and told him I wanted to do something with this legal entertainment niche we shared. It turns out he was thinking the exact same thing. Within a few months, we got together and found a few other guys and created a touring group of lawyer-comedians.

Follow Up

Someone didn’t respond to your email request. Do you (A) give up (B) wait 6 months and try again, or (C) follow up with a phone call. The worst thing that can happen if you go with option C is that they say No. If you go with option A or B, I promise you nothing good will happen.

Often, the person you are trying to reach gets hundreds of emails a day, and yours gets buried. Sometimes, when you send it again, it catches them at the right time and they reply immediately. This is something that I’ve discussed previously when you are trying to do work for a busy solo practictioner. This should be obvious at this age, but phone calls are a must. Sometimes email is sufficient, but when it’s not working, you have to take it to the next level.

Don’t Be Afraid

Whatever you’re trying to accomplish, fear is your worst enemy. Don’t ever be afraid to take chances. By way of example, I recently managed to get David Spade to do a set on my standup show. That’s right, David Spade. Probably one of the biggest comedians in the world, did my show in a room that holds 50 people. Those people were treated to a really intimate and rare moment in comedy. He wasn’t on the bill, most of the audience came there to see a bunch of up-and comers and were shocked to see him and Sarah Silverman doing sets.

How did that happen? Well, long story short. Jeff Ross, better known as the Roast Master, popped in to try out some of his Charlie Sheen Roast jokes on a show I was hosting at the Improv around a month ago. A few weeks later he was having lunch right next to me with Sarah Silverman. He introduced me and we chatted for maybe 2 minutes. I didn’t want to disturb their lunch. At the same time, I knew it would be a coup to get a person like Sarah on my show. So when Jeff went to the bathroom, I simply asked her. Was it terrifying to do that? Yes. But you can accomplish alot by not being afraid. I told her it would be a privilege to have her on my show. She was amazingly kind, she said yes on the spot. Not only that, the day before the show, she asked me if David Sapde could drop by as well. They both showed up and crushed it. It was surreal. People are still talking about it. None of that would have happened if I didn’t overcome my nerves and ask Sarah to do the show. The worst she could have said was no. You could also call this a very good result of networking.

The same goes in any field. If you are transitioning to writing or sales or starting a yoga studio: don’t be afraid to reach out to big names in that field. Ask if you can buy them coffee or a drink. Hit them up on twitter. Find something interesting to share, a helpful tip for them. This is a proven stategy, you may not get everyone to respond, but someone in your field will respond and it will likely help you in some way. Maybe they will tweet you back and a relationship will form and you’ll be on your way. Just don’t be afraid. Whatever you do, be aggressive.


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