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Why Failing Isn’t the Worst Thing to Happen to You When You Quit Your 9-5

Being the Boss

In the last few posts I’ve talked about two of the three most common reasons people give for why they don’t take a leap of faith – self-doubt and financial concerns. In this last post in our “Leap of Faith” series, I want to talk about the third reason – fear of failure upon quitting your 9-5 job.

Let’s Get Real About Failure

First, let’s get something out in the open. EVERYBODY FAILS. Yes, you heard me. Everybody. Even people who seem like they really have their lives together. They fail too. Their failure may be more private, or it may be smaller in form, but failure is a part of everyone’s life. The more that I’ve come to accept this, the more I’ve been able to embrace the failure.

Let me give you an example. When I quit my (stable (read: well-paying) job to start my own company, I spent months fearing what would happen if I failed. What if I didn’t sell anything? If I ran out of money? What if no one liked what I was doing? Failure felt as comfortable to me as a warm, soft blanket; as likely to happen as the sun rising the next day.

The Kick In The Butt That I Needed

After a few months of spending day and night seeing the failure in my thoughts and dreams, I gave myself a kick in the ass. I literally yelled at myself to get over it and stop living as though failure was a given. I let myself take the day to brood in my visions of failure, and then to imagine what would happen if I failed. At first, the picture I painted was bleak – we would run out of money, we would lose our house, we wouldn’t be able to eat. But as I forced myself to evaluate this picture, I realized how unrealistic my visions of failure were.

Unless I fell into a coma or was stupefied into inaction, I was never going to hit that black hole of rock bottom. Long before the money ran out, and we lost the house, and we couldn’t afford food, I was going to FIGURE IT OUT. Why? Because that’s what I’ve always done. Whenever faced with a challenge, I’ve always evaluated the challenge and developed a solution. I’m not special – this is just what we do, as humans, with an innate survival instinct.

Making It Work

I realized that before all hope was I lost, I would know that things weren’t going well and I would pivot. Maybe that meant I would have to take a salaried job in my former industry, or even work at the local coffee shop where half of my household income seems to currently go. It even occurred to me that I might be able to take my newfound “startup CEO” experience and use it to get a job in a new field or industry that interested me. Now that actually sounded exciting…

It’s not that I was giving up on my dream. I was just realizing that if I hit road bumps on my way to achieving it, I would be able to pivot and it wouldn’t be so bad. Yes, it would take me off course for a bit, but the “off-course” wasn’t so horrible and it by no means means that I wouldn’t be able to get back on the right path at some point in the future.

Lots of very smart people have said that failure is a great learning experience. That failure is required before you find success. That failure is in the eye of the beholder. Sure, that’s all true. But I also believe that failure doesn’t have to be HORRIBLE and it doesn’t have to be THE END. Failure after quitting your 9-5 job can simply be a pit stop on the way to achieving your dreams.


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