07 Signs It's Time to Transition From Employee to Entrepreneur

1. You’re passionate about your work, but not your job.

When I first started out in the world of finance, I really enjoyed my work. Helping people to get the funds they needed to achieve their dreams was rewarding, not to mention challenging. But I never felt passionate about my actual job. I had my own ideas for what lending should look and feel like, and I didn’t care to have my schedule and workload set for me every day. I needed more. And that should sound familiar to any successful entrepreneur.

Even seemingly interesting jobs may need to be sacrificed for your true passion. Branden Spikes worked at SpaceX for 10 years before striking out on his own with Spikes Security. When asked why, he said: “Through the years I kept a list of great ideas, and one day I realized that I had a couple of really good ones.” The message: Don’t leave your good ideas unexplored!

2. You’re sick and tired of just thinking about it.

Everybody dreams at least a little about what it would be like to be in charge at work, leading a team and following your own rules. Dreaming about it is enough for most people. But if you find yourself beginning to resent your own entrepreneurial dreams because you haven’t done anything about them, then traditional employment is never going to satisfy you. It’s time to take a risk.

McDonald’s founder Ray Kroc said, “If you’re not a risk taker, you should get the hell out of business.” The message: Achieving your dreams can’t be done from a place of comfort. 

3. You want to help others.

If there’s one thing that separates entrepreneurs driven to build large, successful enterprises, it’s the pleasure they take in building a team and giving opportunities to others. Job creation is one of the biggest, most rewarding responsibilities of entrepreneurship. In fact, the Ewing Marion Kauffman Foundation provided evidence that entrepreneurs who launch new businesses are the driving force behind a vibrant society, by the fact that they create new jobs, renew the economy and expand human welfare.

Giving someone a job he or she wants and needs is an indescribable feeling. The message: If you don’t want to feel responsible for the success of your team, stick with the cubicle.

4. You have support.

Dame Anita Roddick, the founder of cosmetics giant The Body Shop, once said that, “We entrepreneurs are loners, vagabonds, troublemakers. Success is simply a matter of finding and surrounding ourselves with those open-minded and clever souls who can take our insanity and put it to good use.”

That’s a great way to put it. Something a lot of people don’t understand about entrepreneurship is that nobody can do it alone. You need someone to have your back while you’re out risking everything to accomplish your goals. It can be a spouse, a parent, a committed investor, an educator or someone else -- maybe multiple someones. The message: Somebody’s got to help ensure that you have food and shelter and a shoulder to cry on while you’re trying something new.

5. You have a great idea.

It takes more than will to lead to be a great entrepreneur. You’ve got to have something to sell too, and it had better be an improvement on what’s already available in the marketplace. If you’re not obsessed with a new idea to build a better mousetrap and make it easier to get than ever before, you’ve got to find a great idea to rally behind before you quit your job.

Steve Jobs could have spent years building video games for Atari, but he had a vision for making the personal computer accessible and engaging to all. That was what made him succeed where so many solder-jockeys failed: The idea sustained him, even after Apple fired him.

The message: You've got to ask yourself what the point is of borrowing money and working day and night to become just another mousetrap salesman?

6. You’ve got a plan.

Big ideas are great, but they’ll get you nowhere if you don’t have a plan for realizing them. People called Sir Richard Branson crazy when he hocked his record-store chain to start an airline. And maybe he was!

But he had a plan to achieve that dream, based on careful market research, forecasting and financing. Without a solid, realistic plan, his wild vision could have never become a reality. The message: Have a plan. 

7. You also have a backup plan.

A lot of startup businesses fail -- most of them, in fact. No matter how grand your ideas, no matter how careful your plan, you’re putting yourself at risk of becoming another statistic when you step out on your own. Even most successful entrepreneurs don’t get it right on their first try -- I didn’t!

But I had a backup plan to pursue when my first venture failed, and it kept me afloat until I could try again. Never, ever put all of your eggs in one basket. Even Oprah Winfrey was fired from her first television job. The message: If you’ve got a backup plan, you’ll never be afraid to fail.