I want to talk to you about the F word.
No, not that F word.
The other one. Fear.
The F word
Fear is something that most entrepreneurs and business owners face at some time. Let’s be real, you’ve given up a job with a guaranteed monthly income to work for yourself, that’s pretty damned scary, isn’t it?
You don’t always know where your next clients are coming from or if you will work hard and then have to chase someone for payment. You have to deal with things like taxes and bookkeeping and marketing and all different skills that you have never had to think of before.
Fear.
Fear of failure, fear of success, fear of having to tell your family and friends that you couldn’t make it work. Fear of missing your children’s school assemblies still because although you work for yourself you just can’t tear yourself away from the laptop for an hour.
Risk taking is a huge part of running your own business, especially if you decide that you want to go all out and be hugely successful. Nobody ever made a hugely profitable business cautiously.
So if you’re going to carry on down this road of entrepreneurship, freelancing, self-employment or building a business – you need to be prepared to take some risks and overcome your fears.
I don’t agree with the hard masculine approach to overcoming your fears. You know that idea that you just plough through them and get on with it. While I believe that fears are there to teach us something and that we need to overcome them I think we can do this in a more manageable way.
The first step to overcoming your fears is to recognise when you are afraid. Sometimes fear hides itself behind anger, sometimes behind denial. Whenever you feel confronted, upset, angry or want to walk away from something ask yourself what you are afraid of.
And then when you know that you are feeling fear you need to ask yourself what you are afraid of. You might need to sit quietly and really think about this one as it’s not always going to be obvious and you will most likely be trying to deny your fears and won’t want to easily admit what is worrying you.
When you know what you are afraid of its time to overcome that fear. I like to do this by writing out 5 things that are not true about your fear, and 5 positive outcomes that you could achieve if you can get past it.
So if you were afraid that you were going to lose a client by telling them that you can’t start their project for another week then the 5 things that are not true could be : the client will be angry, they will tell other people that you couldn’t help them, you might lose the job, they might refuse to pay you, you might not get a second chance.
Then the 5 positive outcomes of you telling them that you are booked up for another week might be that they learn to respect your time, they see you as an expert because you are so busy, they are happy to wait, they offer to pay you more if you can squeeze it in sooner, or they refer you to their friends because of your honesty.
Being afraid of fear is not a good place to be. Instead, you need to learn to embrace it, accept that it’s part of life, and move on.
What Failure Costs You (And Why the Number Is Smaller Than You Think)
Most people avoid failure because they have never sat down and calculated the real cost of it. I did this exercise for the first time in 2019, after a product launch that brought in roughly 12% of what I had projected. I was mortified. I had spent around £4,000 on ads, six weeks of my time, and a considerable amount of pride. When I finally wrote out every single loss on paper, the total felt devastating in the moment. But when I compared it to what I had learned, and what I changed in every subsequent launch because of that failure, the return on that £4,000 was frankly extraordinary.
Here is the thing most articles about failure will not tell you: the cost of a failed attempt is almost always a fixed, finite number. The cost of not attempting, however, compounds quietly over years. I have spoken to business owners who spent three or four years waiting until conditions were perfect before launching something, and the opportunity they were waiting on had moved on entirely by the time they felt ready. That is not a £4,000 loss. That is a career-defining loss, and it leaves no receipt behind, so you never feel it the way you would feel a concrete failure.
When I coach clients through fear of failure, I ask them to do one specific thing: write down the absolute worst realistic outcome of the thing they are afraid to try, then write down what they would do the following Monday morning if that outcome happened. Almost without exception, they find that they would recover. They would pivot, refund customers, apologise, start something smaller, or find a new angle. The worst realistic outcome is survivable. The exercise works because it forces the brain to stop treating failure as an abstract catastrophe and start treating it as a problem with a practical response.
- Write the worst realistic outcome in one sentence, not a vague fear, but a specific scenario
- Write three concrete actions you would take the following week if it happened
- Estimate the actual financial cost, not the emotional one, and compare it to what doing nothing costs you over twelve months
- Identify one person who has experienced a similar failure and is still working, still earning, still building
I want to be honest about something else: some failures do cost more than others, and pretending otherwise is patronising. A failure that damages a client relationship, or that loses money you cannot afford, carries real weight. I am not suggesting you treat every setback as a gift wrapped in a bow. What I am saying is that most of us are not risking bankruptcy or serious harm. We are risking embarrassment, and embarrassment is the least expensive tuition you will ever pay for skills that stick.
The F word gets its power from vagueness. The moment you make failure specific, costed, and survivable on paper, it shrinks. It does not disappear, but it shrinks to a size you can make a decision about. That is all you need: not fearlessness, just a clear enough picture of the actual risk that your judgement can function again.
The short version: Failure is not the opposite of success, it is part of the path to it. Every entrepreneur I have ever spoken to has a failure story that shaped their biggest breakthrough. Stop treating the F word like a dirty secret and start treating it like the data it is.
Frequently asked questions
Why do so many business owners fear failure so much?
A lot of it comes down to identity. When you have poured your time, money, and reputation into something, a failed project can feel like a personal verdict on your worth. The problem is that this mindset makes you risk-averse in ways that slow your growth down.
How do you tell the difference between a failure worth learning from and one worth walking away from?
Ask yourself whether the core idea still has merit or whether the market has given you a clear and repeated signal that it does not. One bad quarter is data. Three years of the same bad quarter is a pattern, and patterns deserve honest attention.
Can talking openly about failure help your personal brand?
Yes, and more than most people expect. Audiences and clients connect with honesty. Sharing what went wrong, what you did next, and what changed shows real leadership in a way that a polished highlight reel never can.
What is the first step to building a healthier relationship with failure?
Write it down. Document what happened, what you assumed going in, and what the outcome told you. Turning a painful experience into a written record shifts it from an emotional wound into a business lesson you can reference and build on.
