Three years ago, I received the biggest promotion of my career. After spending 10 years selling Oracle's enterprise software--and working my way up from inside sales to sales director--I had proven to be a top performer in both my company and the industry at large.

My CEO pulled me aside and laid out the terms of the promotion. He was increasing my salary by an astounding 65 percent, and I was given a V.P. title for the first time. My territory would be the western U.S., my expense account was now uncapped, and I could work remotely whenever I wanted.

I signed the contract with a perfect signature--there was nothing to negotiate. 

Just three months after the promotion of a lifetime, I resigned.

The CEO was completely and utterly shocked. "Darren, I gave you everything you asked for," he said in disbelief. "What more could you possibly want?"

What I wanted was the one thing he could never give me: to be my own boss.

For several years, I had been moonlighting on the side, operating a startup in the film business with a business partner. We made all the first-time entrepreneur mistakes possible: starting a tech company without a technical co-founder, solving a problem in a niche market, and trying to monetize an audience that couldn't afford our products (to name a few).

After two years, we pivoted, first into a film distribution company, and then again into a marketing company. Fast-forward another few years, and we had marketed 80 Kickstarter and Indiegogo campaigns. While we were generating revenue at this point, it was nominal. 

Then, in early 2015, we were introduced to an automotive startup that wanted to raise capital using a new securities exemption. This new form of capital raising allowed private companies to raise up to $50 million, and with the ability to market to the general public.  

We bid the deal, and won. It was the largest contract we had ever signed.  

I always remembered the Eminem lyric in "Lose Yourself"--that "opportunity comes once in a lifetime." Intuitively, my gut was telling me that this deal could be a game-changer for my startup, but only if we made it a smashing success.

And this wasn't just any campaign: It was a marketing campaign for a car company, and we had full control over the creative. I also knew that I couldn't burn both ends of the candle forever. I needed to go all-in and commit 100 percent of my time and energy to make it work.

So I quit my job after the biggest promotion of my career, and never looked back.

We delivered the campaign, and made history in the process. Our client raised $17 million, and became the first crowdfinanced IPO ever. The success of the campaign set my company on a new trajectory, with millions in revenue and the most incredible clients imaginable.

I took a calculated risk by walking away from golden handcuffs--and it was the best decision I ever made. I now own and operate multiple businesses, and while being an entrepreneur is both challenging and stressful, I am fortunate to say that I am living my dream.

You too can make the move to entrepreneurship. While leaving a steady, good-paying job is scary, it may be necessary to succeed in your own business--it was for me. 

Ask yourself: If you left your company, and your startup didn't work out six months or one year later, would you still be employable in your old industry? If the answer is "yes," you have something to fall back on. Your experience, network, and reputation will still be there. 

Before you make your move, you can always start a side hustle, too. That way you can protect your primary source of income, learn as you as go, and build up your revenues over time. You'll need to work longer and harder than you ever have before, but that's what will make you successful in the long run anyway.

As Gary Vaynerchuk has said, "Without hustle, your talent will only get you so far." And at some point, your hustle will need to be fully focused on your business in order for you to realize your full potential. You'll know when the time is right. Then make your move.

Published on: Jul 16, 2018
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