Six common fears of entrepreneurship and how to overcome them

Now that I’ve been *officially* up and running with Hooligan’s Entrepreneurial Consulting services for a few months, I wanted to write about a common set of fears that I am beginning to see with almost every Entrepreneur. First, I’d like to say that being scared of entrepreneurship is suuuuuuper normal. In fact, I’d argue that if you weren’t scared even a little bit, that there’s something wrong. The degrees of which I am noticing each component vary from “gut-wrenching-fetal-position” to “meh”, but exist in everyone to some degree.

1. Fear of imposter syndrome

The imposter syndrome is “a concept describing individuals who are marked by an inability to internalize their accomplishments and a persistent fear of being exposed as a “fraud”.” Even seasoned veterans in their field seem to possess this complex in some way. Most often it occurs in people who are experts in their field, but lack the business background they believe it takes to start up their own company.

2. Fear of failure

I figured I could go one point without mentioning how important it is to have a business plan. I am a big advocate of the mantra that “you can achieve anything, if you plan for it”. One giant advantage to planning is that you put your current self in your future self’s position and think through what you would do before you do it. When you take this approach, you truly conceptualize the scope of your venture, figure out how you’re going to do it, and when that’s all said and done, create a list of all the risks and things that could go wrong. When evaluating risks you can adjust your plan to ensure they are covered, or you come up with risk mitigation strategies so you know exactly what you are going to do if one of the risks manifests into a serious issue.

Fear of failure comes from the unknown, which can be mitigated if you do yourself a favour and plan for it.

3. Fear of doing it on your own

While you may have been a Hair Stylist for 15 years, it doesn’t necessarily mean that you know how exactly to run a salon. But your desire to take a list of all the things you’d do differently if it were you running the show, could be the epitome of awesome.

If you’re in a situation where you are currently working in an environment similar to one you’d like to start on your own like the example above, I recommend taking 3 months to do an intense assessment of the current operations. Working while you are planning your startup is extremely advantageous as it relieves the financial pressure (see next point below) of knowing where your next paycheque is going to come from, while providing you with an opportunity to see things through another lens.

4. Fear of losing money

Money problems are the number one stressor in most people’s life. Again, if you plan your financial strategy slightly more thoroughly than on the back of napkin, I guarantee you the fear of losing money will slowly start to dissipate. When you know how much you charge and what your margins are, you can quickly and easily determine ways to make sure you are as successful as possible. You do not need to be a financial guru à la Warren Buffet to make money in your business. But it all starts with a plan.

5. Fear of commitment

This is one that unfortunately doesn’t take a plan to resolve. My consulting business includes a lot of tire-kickers who have a lot of ideas, but cannot commit to following through with them, or following through with paying someone to help them come up with a strategy (even though it might save them tens of thousands of dollars in the long run). Committing to your idea, vision, and eventually your business is a character trait that cannot be taught. If you are scared that you might get bored or disinterested in your business before you’ve even started it, chances are you will. The ventures that succeed are the ones that have incubated in someone’s brain for years and involved several iterations before they get to me to put them down on paper.

If you are not passionate about your business or idea, it shows and quickly turns customers away.

6. Fear of being too busy

People shy away from starting the business of their dreams, even if it’s an amazing idea, because they’re afraid of how much work it will take. The reality is that for the first six months to a year, you are usually the chief, cook and bottle washer until you get things up and running. Yes you will be busy, yes it will be stressful, but after time and success, you will be able to loosen the reins and bring on some people to help you out. But the fear of your own laziness shouldn’t stop you from achieving your dreams.


Starting your own business is a lot like becoming a parent for the first time (speaking from experience). While you can read every article on the internet and plan for every eventuality, things will come up that you could have never thought of or prepared for. And that’s ok. Having a strong support system and passionate following of people who believe in you and your venture will ultimately save you, and your business. In both babies and business, it really does take a village.

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