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Six fears every entrepreneur faces

28 Oct 2019

Written by Simon Rogerson

The purpose of fear

The purpose of fear is simple. It’s about survival. Without fear, we’d play with fire, walk across roads without looking or eat ghost chillies as snacks. But we don’t, because it could be dangerous. Over time, and through experience, we’ve been programmed to respond in a certain kind of way when faced with fear.

Charles Darwin even carried out an experiment to prove the point. He went to London Zoo and put his face as close as possible to a glass enclosure containing a venomous snake. Every time the snake lunged at the glass, he jumped backwards in fright. The logical part of his brain (which understood that he couldn’t be bitten through the glass) simply couldn’t beat the instincts at play.

There are times, however, when we need to overcome fear to try new things. And, on occasions, this fear can even be exciting; that’s why we watch horror movies, go skydiving and ride rollercoasters.

Our brains carry out a constant balancing act between self-preservation and pushing the boundaries. This is particularly true for entrepreneurs, which is perhaps unsurprising given that risk-taking is a fundamental part of building any business. My own experience over the last twenty years suggests that there are six stages of fear an entrepreneur will go through:

#1: Fear of making the leap

Faced with overwhelming cynicism (from your inner voice, as well as outsiders), there will always be a part of you that wants to play it safe. The fear of failure, of looking foolish in front of your friends and family, or of losing your savings and having to start again are all big, scary reasons not to make the leap and try to start a business.

When faced with these fears myself, one thought got me through: you only have one life and it would be a shame to get to the end of it never having tried. If you’re still on the fence, there’s another good rule of thumb to consider: if you wake up every morning for a month or so thinking about your own business idea, that’s probably enough evidence that it’s time to get started.

#2: Fear of being an imposter

For those who make the leap and start their own business, the next fear will kick in almost immediately: imposter syndrome. Unhelpfully, your brain will probably have this mental image of entrepreneurs as smart, renegade and successful people, who seemingly glide along, effortlessly disrupting and reimagining the industries they’re operating in. You might feel as though you’re nothing like them, that you don’t really belong and that you’re not qualified for the task ahead.

The first thing to understand is that this picture of an entrepreneur is, for the most part, untrue. Most entrepreneurs have the same fears, the same worries and the same issues as everyone else. And they too will have felt their own version of imposter syndrome.

The second point is that the best medicine for imposter syndrome will always be generating some revenue. There’s nothing quite like the practical vote of confidence you’ll get when you land your first paying customer.

#3: Fear of being on your own

Once you land some customers, the imposter syndrome will give way to something a bit scarier: loneliness. As the business owner, you’re ultimately accountable for everything and this singular level of responsibility can be quite isolating. There are two suggestions I’d make here.

First, I’d encourage anyone grappling with this kind of fear to talk to someone about it. Talk to your co-founder, to your friends or family, or to a professional. There are some excellent services like Mind or Shout who can offer mental health support.

Secondly, I’d suggest sharing ownership at every level in your business. This will drive accountability among your employees and gives everyone a sense of togetherness.

#4: Fear of losing what you have

As your business becomes more successful your fears are, unfortunately, likely to continue evolving instead of going away. Even when things are working, you’ll start to worry about what could go wrong and about what you stand to lose, now you’ve built something.

In my opinion, these are good worries to have, in the same sense that actors welcome a little bit of nervousness before a big performance. Over the years, a little bit of this kind of fear has kept me on my toes, meaning I’m ready to react to changes and that I never get complacent.

#5: Fear of letting go

Most entrepreneurs like to be in control. That’s easy to do when the business is small but as it scales, a command-and-control style approach just doesn’t work. And the fear of letting go of control is very real.

The only solution to this is to hire great people. If you trust the people you’ve brought in, letting go of the reins will feel far less daunting. There’s another test here, and this can apply to anyone who manages people – if you look at your diary in the morning and silently groan at the prospect of a 121 with someone on your team, that probably means they need to go.

#6: Fear of standing still

Entrepreneurs are never short of ideas and they tend to want to keep moving, constantly. But this can become more difficult to achieve as businesses gets bigger. Process, governance and structure are all necessary parts of a larger business but, in some ways, they fight against the natural instincts of the entrepreneur. And they may lead you to worry that your company isn’t as ‘entrepreneurial’ or as ‘edgy’ as you’d like it to be, or as it once was.

The solution here, I’ve found, is to keep building. Keep setting up new companies, or new ventures, and give them the space and the flexibility to be successful. It’s what we’ve done at Octopus. We’re a group of companies, ranging from early stage start-ups through to quite large, established businesses. The key here is to keep the new and the old businesses quite separate, at least in the early days.

Fight the fear

Fear and worry are a huge part of any entrepreneur’s life, but the journey of starting a business is more than worth fighting through these fears.

I lasted two and a half years as a graduate trainee before I left to do my own thing. In my old job, I used to look at my watch at roughly the same time every day (1pm), not because I really wanted to know the time, but because I wanted to know how long I had left before I could go home. That was my prompt to leave. And I wouldn’t change the last twenty years for the world.

If you are considering starting a business, I’d encourage you to give it a go. Entrepreneurs, to me, are the agents of change. And when you look around at the environmental and social crises playing out around us, there’s no end of opportunity for them to make a difference.



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