Why is Being an Entrepreneur So Difficult?

Photo via    unsplash.com

Photo via unsplash.com

You are playing two games, fighting two battles - the one going on in the office and the one going on in your head. Every entrepreneur has to solve the problem of how to make their business a success, whilst simultaneously battling the consequences of the scarcity of their time, attention, and energy. One of these problems is hard, the other almost insurmountable. 

Most of my efforts are directed towards solving the first - the easier - of these problems: i.e. how to create a vehicle to deliver on your business goals. I say its easier because it’s typically aligned with where you want to go anyway, plus we have a process for doing it. But the mental game - how you stay in the game - that’s your Everest. The best I can offer you is a diagnosis and some pointers for how to help yourself.

In a previous piece, The Five Curses for an Entrepreneur, I observed that there are five evil forces at work in the lives of most business leaders. Forces that conspire to hinder them and prevent them from achieving their goals. They are:

1. Stress

2. Overconfidence

3. Poorly understood business needs

4. Untested assumptions

5. Failure to communicate

If we wanted to create a simple model for a successful entrepreneur it might look something like:

good idea + skill + confidence + passion = success

But this belies the evidence, because passionate, skilful, confident people fail with their ideas all the time. I’ve already mentioned the Startup Genome Report and it’s rather horrible picture of failure. But I’ve been in the London startup scene almost 20 years, meeting a lot of new enterprises along the way, and can count on my fingers the number of entrepreneurs I met who didn’t blend most or all of these qualities.

So if a good idea, skill, confidence and passion are not enough - what else do we need? In developing a talk called ‘The Effective Entrepreneur’. I extended the model to include three further factors: presence, focus, and judgement.


Are we present in the moment? Or are we absent, distracted or unavailable?

If we are more present, we are more alive to the opportunities and threats that swirl around us. Success can often turn on a chance meeting - sometimes it is not the meeting that you anticipated or planned for.

Yet, so often we are not present and find our head is elsewhere. We’re in the middle of doing something but feel distracted; thinking about - or getting anxious about - our next meeting, tomorrow’s presentation, or next week’s pitch.

Mindfulness practice can help here. It can also be enough to remind ourselves, periodically, that there is no point in doing work that we’re not willing to be in. If you have a co-founder or team members, maybe you should challenge each other to be present?


This one presents an incredible challenge for smart, creative, people.

Can we focus on one idea, on one product, long enough to make it as successful as it can and deserves to be?

The trap is that smart people believe they can multi-task and that they are not cheating themselves or the opportunities they are working on. Maybe some can. Maybe you are one of those rare Elon Musk types? More likely, you’re like me and would be better off just doing the most important thing in front of us.

Try to remind yourself focus is good. Decide what is most important and do that. This means saying no to things that are less important. This is the right thing to do. If you’re struggling with that you might have a problem with…


Do we display sound judgement most or all of the time? Or is our judgement suspect, either in terms of being unable to make decisions, or making relatively poor decisions?

Presence, focus, and judgement are quite closely related to each other. As various factors affect our judgement and decision making, we are far less likely to be as present and focused as we should be. But the most insidious of the three is judgement because, as your judgement suffers, your ability to realise this gets diminished. People with poor judgement are often the last to know!

The only defence that I can suggest is that you need someone in your life who, when they tell you that your judgement is not A-1, you trust them enough to listen and do something about it. This could be a mentor, advisor or maybe even a navigator! But it shouldn’t be a family member or friend (they will find it hard to be objective about your ‘baby’). If you don’t have such a person in your life, or can’t find one, maybe that’s also a signal you should listen to.

Now, let’s be honest here - nobody is going to display 100% faculty across these all of these factors all of the time. That’s not human. So, we have to ask ourselves, “What should I be shooting for? What is achievable? What is good enough? And how would/will I know if I am achieving it?”

Again, this can be very hard to judge if you are on your own. So, find someone who can help you and, in the meantime - listen to your gut. It won’t steer you wrong. Accept that you will commit a cardinal sin from time-to-time,  don’t beat yourself up about it, move on and try to do better tomorrow.

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Rachael ChadwickComment