At A Crossroads In My Career

How to know when to quit your job or if it is a good idea to quit your job and do something full time that you really love, or if you still should still keep your job and continue building your dream career or business on the side part time.

In this video coaching newsletter, I discuss an email from a viewer who has been following my work for about a year. He says that he’s never been happier. He went from pursuing a career he had no passion for and dating one awful woman at a time, to pursuing his childhood dream and seeing multiple great women. He always wanted to do standup comedy and decided he could not go to his grave without attempting to get on stage and tell some jokes. He went from doing open mic nights to being a potential rising star in the Pacific Northwest.

He’s booking shows and being featured in different cities. An agent now wants to take him on a comedy tour doing fifteen shows in thirty days. It’s good money, but he asks if I think he should make the leap now, or give it another year to hone his skills and grow his reputation. My comments are in (bold parenthesis like this below) in the body of his email.

Hey Coach,

I’ve been following you for about a year, and I have to say, I’ve never been happier. I went from pursuing a career I had no passion for and dating one awful woman at a time to pursuing my childhood dream and seeing multiple great women. (That’s awesome dude. It’s your birthright. We have a much bigger impact on the world when we do what we love.) I feel like I’ve done a complete 180. I decided that I couldn’t go to my grave without attempting to get on stage and tell some jokes. (People on their deathbed always say they wish they had taken more risks. When you get to the end of your life, you’re out of time.) I got up a year ago and dove in head first. I went from a new open mic comic to a potential rising star in the Pacific Northwest. I’m booking shows and have been asked to feature in different cities.

Here’s the problem. A fellow comic has a booking agent who likes me, and wants me to go on tour with him this fall. It’s 15 shows in 30 days. The money would easily get me through the month but I have two kids and responsibilities. I don’t know if I should take this leap and try to fulfill my dream of just doing comedy, or if I should give it another year of honing my skills before I take a leap. Any advice would be appreciated! (All I see here is that you have a guaranteed income for one month. It’s totally possible they book you for another month after you do these shows, but what’s your downside risk in this situation? You have kids that depend upon you. It’s not like you’re single and can focus 100% on your comedy. If you love and value yourself, and you have a lot to offer, negotiate a deal where you can keep your job and work on the weekends.)

Bob

“In every business deal, investment, career move and personal relationship, you should always know your downside. In other words, what is your downside risk if things do not go as you planned? It’s essential to be optimistic and go for the things you want in life in order to be successful, but you should do it in a balanced way, with minimal risk to your career, business, health and emotional well being. Making progress towards your grandest goals and dreams always involves risk, but you should never risk more than you are willing, or can afford to lose. Incremental progress is a smart, steady, sure and balanced way to succeed, but recklessly gambling in hopes of an instant payoff is like thinking you can “beat the house” in a casino where the odds are never stacked in your favor.” ~ Coach Corey Wayne

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