Home Advice For The Young At Heart Take The Jump! Overcoming The Mental Barriers Of Becoming An Entrepreneur

Take The Jump! Overcoming The Mental Barriers Of Becoming An Entrepreneur


taking the leap jump

Image credit: Taking the leap from Shutterstock

by Rob Villeneuve, CEO of Rebel.com

Making the jump from a traditional career is terrifying. I found that leaving behind a predictable income in favor of following my passion wasn’t dissimilar to jumping out of an airplane with a questionable parachute. Starting your own business is filled with obstacles, fear, and crippling self-doubt; it seems crazy that anyone would ever choose that life.

But every jump, terrifying moment, failure, and success is absolutely worth the blood, sweat, and tears. And you’ll have plenty of all three.

What’s the Worst That Could Happen?

There are countless fears associated with starting your own business. What happens if I fail? Will future employers care about the “gap” in my résumé? And, scariest of all, what if I succeed?

By starting at the “worst,” I worked backward and created a plan for every situation.

In the case of future companies questioning my employment gap, I chose to focus on how much value I could offer as an entrepreneur. I had to remind myself that building a business was an experience that would allow me to relate to leaders in a way that other employees couldn’t, which ultimately put me ahead.

I often considered the financial stress of not knowing how much I would earn (and understanding that it will, at least to start, be considerably less) and decided that a properly constructed savings plan could give me plenty of time to give the startup world a try.

I wasn’t immune to self-doubt, but considering solutions for what I feared most let me concentrate on the business itself rather than what I was scared of. So if you’re thinking about getting an entrepreneurial education like I did, here are a few ways to find your courage:

1. Prepare your finances.

The financial barrier to entrepreneurship is real and should be given serious attention. Starting a company is scary enough without personal finances looming over your head. To overcome this barrier, I’d recommend taking the savings you have to find a financial runway. Then, find a way to double that time. I learned this the hard way a few months in.

Remember: You will naturally adapt your lifestyle to your income, whether it’s an annual income of millions of dollars or $15,000. Be real with yourself about your finances, and decide what you need to truly sustain your lifestyle. Avoiding financial stresses by preparing a runway will give you the room you need to really make a go of it.

2. Check your passion.

You can’t go into this thinking you’ll be Elon Musk. If you’re attempting to start a business you’re passionate about, get feedback and mentors who will be honest with you about the likelihood of your passion evolving into a viable business.

Passion alone won’t get you to the finish line, so it’s important to be honest with yourself. Mark Manson does a great job explaining the reality check that’s necessary to stick it out through the rough patches. Even real passion projects — what Elle Luna would call pursuing your “must” — can serve up some pretty rough days. Double-check to make sure your inner fire is prepared to survive the storms ahead.

3. Ask for feedback, then ask for some more.

Many entrepreneurs are fearful of someone stealing their idea, so they go stealth and keep it a secret. But they’re protecting the wrong thing. The idea isn’t the gold nugget; the execution is. Share your idea with as many people as possible, and be open to really hearing their thoughts and feedback. Spend extra time with the people who think it’s a bad idea. These conversations will be exceptionally valuable to you.

4. Realize that your time is worth something.

Believing that your time is actually worth money is hard. In the beginning, I did a lot of work for free because I lacked the understanding that doing so actually devalued my work.

Overcoming this idea took a while. I started by asking for too little. Then, I slowly learned that I could ask for more. It turns out that most people were not only willing to pay for what I was offering, but they were also happy to do it. Knowing my value — and gaining the art of “selling myself” by speaking authentically about my passion — led me to ask for the money I deserved.

In the end, the worst-case scenarios, the gap in my résumé, and the possibility of failure were absolutely my career accelerators. Finding the courage to expand myself through entrepreneurship taught me more than any book or lecture ever could.

If you’re considering making the jump — questionable parachute and all — know that it won’t be easy, but it will be worth it. Just prepare yourself for the mental blocks, and take the leap.


Rob Villeneuve

Rob Villeneuve is the CEO of Rebel.com, an expert in creating simple, useful tools to empower participation in the world’s bravest communication space: the Internet. With hundreds of domain endings available, Rob and Rebel.com are experts in crafting the right identity.


  1. This is excellent advice Rob, thank you for sharing! I am going through this process now and it is terrifying but yet I cannot seem to let go of the drive and determination to make things happen. Implementation is key.

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