Never be afraid to bet on yourself

Jon Gilman
2 min readMar 16, 2014

We live in a world where it’s very easy to find an “expert” for whatever field or career path you’re interested in exploring. There’s always someone with more experience than you willing to tell you the way it’s supposed to be done. Having all this information at your fingertips is as empowering as it is intimidating. It’s so easy to fall into the trap of taking what you see in a blog post, Quora thread, or tweet as gospel (especially when the author is a person you recognize and admire) because you fear that you won’t be able to match that person’s success unless you follow the same steps.

But the reality of life is that there is no playbook. Instead, we’re all just figuring things out as we go along. It can be very helpful to hear what has worked for other people but the notion that someone can give an exact recipe for success in any given field is just plain bullshit. We’re all making observations, recognizing patterns, and generalizing based on our own experiences. However, the rub is that everyone’s situation is different. The honest answer to any question about what it takes to succeed is, “It depends”.

To get into specifics of what it’ll take, you need to define what success means to you. But even after you make that decision, don’t sell yourself short in getting there. Just because you lack direct experience with a field or career path doesn’t mean that you can’t find your own path to success. There’s always a way to make it happen. All you have to do is bet on yourself to figure things out.

And that’s exactly I’m about to do. I’ve decided to move on from RunKeeper after an amazing 2 year journey. I’ve learned a ton and grown a ton but ultimately felt the time was right for my next chapter. It’s been my longstanding goal to build something from scratch but I’ve been held back from taking that leap because I felt I wasn’t ready. I had so many preconceived notions around what I needed to do before I was ready to be a founder. But what I’ve come to realize is that there is no one path to success. Life isn’t a serious of tasks to complete before unlocking the next level. We each have our own unique journeys to get to where we want to go in life.

Just remember, once you figure out your ideal destination, never be afraid to bet on yourself to get there.

Find me on Twitter (@jongilman) to follow along for my new journey.

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