Gambling On Myself Was The Best Decision I Ever Made, ‘Cause No One Else Would

gambling on yourself


As I’ve gotten older, I’ve come to some conclusions. One of the most important ones is that gambling on yourself is the way to get to where you want to be. I know, it sounds simple right? But isn’t it funny how people are willing to drop hundreds or thousands of dollars by gambling on their favorite sports teams and not reinvest that same amount on themselves?

Whether you’re job-hunting and can’t seem to catch a damn break, you’re stuck in a dead end career that’s leaving you unfulfilled and underappreciated, or you feel as if you’ve got plenty of good ideas that are worth putting some passion and energy behind, I can tell you firsthand how gambling on yourself gives you the control in your life. It allows you to find balance and, in a way, be proud that you’re not doing the same basic sh*t that all of your other buddies are doing.

Personally, my moment came back in April, when a men’s lifestyle magazine I was overseeing folded because of a decision from upper management. For about a year-in-a-half, I poured all of my energy into that job, rebranding the legacy website and creating a new audience through multiple platforms. I worked 12-hour days, waking up at 6 a.m. every morning since I’m on the west coast and wanted to be on the same schedule as my east coast colleagues. However, rather than stop at 3 p.m., I was still working all night and weekends. Did it burn me out? Possibly. But the opportunity was so big that I had a responsibility to do what I could to keep it going.

Unfortunately, when the hammer came down that the publication was going to fold after over two decades, I felt… relieved. Sure, the uncertainty of what was coming next crept into my mind, but I had hustled before and am still alive, so I’d do it again. Except this time would be different, because I was gambling on myself.

Rather than continue the lifestyle of going out to bars, being part of the rat race and spend hundreds of dollars on wasted nights being, well, wasted, I made the change to invest in what I believe in. It wasn’t, and still isn’t, easy. It’s hard telling people “no” when they expect you to host friends or go out every Friday and Saturday. But the long-term success outweighs the short-term endeavors.

In the time since I lost my job in April, I’ve had a few moments of “whoa is me,” where I freak out and compare myself to others, wasting time applying to jobs I don’t really want, but think I need. When I remember what it was like to make a regular, hefty salary. But, why bend over backwards and give everything you have only to be told one day that it’s all over?

By now, I’m sure you’re asking yourselves what the hell I’ve been doing with my life to, you know, make money. I’m in the process of raising money for a sports bar, which, if you’re ever in Seattle, I expect you to take me up on a free first drink. I’m putting together an outline for a book. I’m consulting with a few different men’s lifestyle sites. I’m creating a podcast and a new website with a former colleague. Overall, I’m working just as hard, at odd hours of the day — but it’s for me.

Gambling on yourself isn’t easy. It requires thick skin and adaptability, understanding no day is the exact same. There are no days of mailing it in by sitting at your desk hungover, knowing you’re getting a paycheck even if you only send a few emails and B.S. your way through some meetings. It’s exciting, nerve-wracking and fulfilling all at the same time.

People talk about the Sunday Scaries, well, when you invest in yourself and your interests, the only scaries you have are the ones your create in your mind. Have confidence in your abilities, stay the course, understand the twist and turns of this journey and refuse to take the easy way out by taking a full-time job because it’s a simple paycheck.

Your focus becomes your reality, so shut up and hustle your way to what you want; I know I’m doing it and have never been happier.

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