Why entrepreneurs work with coaches to preserve their sanity and save precious time

Ellen Kate Donnelly
10 min readMar 12, 2021

Taking a look at the psychological toll of company building and the lifeline of support coaching can provide.

As both an entrepreneur and a coach who has their own coach, I have a few things to say on this topic.

The FT-backed startup publication recently posted results from their poll of readers, showing 50% of their respondents work with a coach, the biggest portion being Founders.

https://mailchi.mp/sifted/alternatives-vc-financing?e=465dd1c8f4

Coaching is popular for entrepreneurs for a key reasons, including helping with anxiety, improving critical thinking and saving crucial time and money.

Reason 1: The stigma around failure, stress and anxiety

We live in a culture that celebrates entrepreneur success.

People want entrepreneurs to be successful, its good for the economy, it boosts the belief that we can carve a path of our own and it feels good to be associated with or buy from a company that is doing well.

No one wants to buy from a struggling business desperate for your money.

Going into an empty store where the owner practically begs you to buy something is never a good look. People want to buy from the socially-approved companies and shiny brands that their peers are already buying from. Success is shiny. Look at cult brands like Nike, Glossier, Peleton, Apple. We wear successful brands as symbols of our own identity.

So when success is nowhere to be found, entrepreneurs are not exactly shouting this from the rooftops.

The ‘fake it until you make it culture’ becomes the marching beat for entrepreneurs precisely because it works. If we act successful to the public, eventually we will become successful.

They say you’ve only failed when you give up. Going for months on end with no money coming in and a depleting savings account becomes a badge of honour for those who eventually make it.

A for those who don’t? We rarely hear those stories.

Yet failure is inherent in the startup building process. It is listed loud and clear as as warning sign to anyone who considers starting a company — “9 out of every 10 new businesses fail within within their first decade.”

But for all the warnings of failure in entrepreneurship more and more people dive head first into it each day. These stats from the USA revealed a whopping 4.1m new businesses were registered in 2020.

https://www.oberlo.co.uk/statistics/how-many-new-businesses-start-each-year

It has never been easier to start a business, so many people do.

I believe this is a good thing. Yet imagine the person who has never stepped foot in a gym turning up to the IWF weightlifting championships expecting to survive.

You need to build up your emotional and mental fitness in entrepreneurship as the game is about your tolerance to challenging emotions.

What reps are you doing for your mind before you throw the towel in at your day job and launch a company?

Coaches are there to help absorb the almost inevitable levels of chronic stress and anxiety comes with company building.

Because our culture wants our entrepreneurs to be successful, talking openly about mental health challenges, or personal issues like debt or health issues, can get stigmatised. People building companies will often work through these challenges and accept them as par for the course.

In the 2019 Entrepreneur Pressure & Wellbeing Study from Weare3Sixty, of the 270 UK based entrepreneurs who were interviewed, 90% of respondents reported signs of mental strain, yet 93% said they were distinctly happy in their roles. Getting on with it basically.

But sooner or later these strains will wreak havoc. Founders who are burned out will become erratic, moody and less productive which, in turn, impacts not just their own but also their employees lives.

High stress seems like a common denominator in company building and stress is linked to poor decision-making, procrastination, insomnia, migraines, and even irritable bowel syndrome to high stress. Stress can sink a company when left unchecked.

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In this Inc. post “The Psychological Price of Entrepreneurship” we hear how world-renowned VC Brad Feld conducted a study into anxiety and depression in entrepreneurship and was flooded with responses from high profile startup leaders sharing their darkest moments. Many feeling that admitting their weaknesses did not feel like an option some even feeling suicidal.

Coaching is not the only solution to stress, anxiety and depression.

Building emotional fitness is about general self awareness building, tuning into your emotions and managing them appropriately. This can be done with therapy, meditation, journalling or mindfulness techniques too.

However the beauty of coaching is that a coach should be trained to understand the psychological toll, and support the client to reach the right solution to their problems. They will there through thick and thin, offering companionship through times of need.

I see it as a win when a client breaks down into tears during our sessions together. Not because I want to see them unhappy, but because it means we have reached a moment of breakthrough where they can be honest with themselves as much as anything.

Building a company is hard. The sooner we admit the need for help for the tough times the better equipped we can be to seek help where we need it, and prevent the emotional strain becoming intolerable.

Reason 2: Entrepreneurs need a sparring partner for their thoughts

Building a business is also a lonely road.

Solo founders especially spend a lot of time in their own heads, with conflicting thoughts and the feeling that they are going around in circles.

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I have been there so many times.

For example, the process of niching for me has taken me nearly 18 months and I’ve ended up where I first started. You go a little crazy with all of your thoughts and ideas each day.

Coaches help you channel these ideas productively.

I’ve never worked with a coach because I need more information. My brain is too full of ideas and inspiration without hearing more of this.

Most entrepreneurs are big thinkers and they are not lacking ideas but lacking methods to clearly refine the ideas they already have.

This is an important distinction between coaching and mentoring, as a coach is not there to tell you what to do, but to ask you the right questions so you can reach this conclusion on your own terms.

The whole essence of a startup is that you are building something that has not been done before. In a new venture there are no guarantees. There is no one guru out there with all the answers about what you should do (and if someone is telling you they are this person, run a mile.)

And so it is precisely because there are no set answers that you as the entrepreneur, need to strengthen your own thinking capacity. You need to become better at finding these answers for yourself. Building a business is an accumulation of decisions after decisions. The better you can think the better you are able to execute.

A good coach should motivates their clients to believe in themselves and their ability to solve the problems they are facing by drawing on their own unique wisdom.

I’ve observed many clients ‘forget’ about knowledge they have gained in the past, only to remember it at the right time to make the right decision for their business when push came to shove. I have helped them to develop more trust in their own decisions, through knowing their values and strengths and refining their mission more clearly so that answers become obvious in the heat of the moment.

The main reason entrepreneurs, like most people, have problems with thinking clearly is that we are conditioned to believe we do not have the answers. We are fed marketing materials that tell us we need to be more and do more and buy this or that to succeed.

We have negative recurring thoughts that we are not good enough, or that other people are doing better than we are. According to the National Science Foundation, an average person has about 12,000 to 60,000 thoughts per day. Of those, 80% are negative and 95% are repetitive thoughts.

A bit depressing?

The good news… we are not our thoughts. Realising this fact means that we can separate our thoughts about ourselves from the actions we choose take.

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If you believe you are not good enough you are unlikely to send that proposal, connection request or post the video that will give your business the boost it needs. The entrepreneurs who do well in this world are the ones who are able to separate their beliefs from their actions. Doing the hard thing that your business needs you to do often involves putting your ego, pride, fear, shame, or vulnerability to one side.

So sitting with your thoughts all day long is a recipe for disaster.

The remedy to our crazy brains? Getting thoughts out of your head.

A calm mind is a mind that’s been listened to.

You need to think out loud for your sanity, so you can get out of your own way. A coach is trained to support you in this process, and do the work with you about what might be triggering you as well as unblocking obstacles in your way (real or imagined).

Coaching is designed to help you think better for long term transformation and mental clarity, beyond just solving short term immediate problems. Studies have shown coaching as one of the few professional development approaches that can truly bring about long-term change.

Reason 3: Entrepreneurs need short-cuts

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I often tell people during our discovery call that they don’t need a coach.

People are shocked to hear me say this, but they are thinking this anyway. No you don’t need a coach.

The average person will never work with a coach. But who really wants to stay average?

Investing in a coach is a big investment in time and money. I may write another piece on why this is the case and why it will always cost a lot of money to work with a great coach (my coach is charging me £7k over six months).

But what hurts your bank balance in the short term can pay back dividends down the line. Coaching saves you time, which is really saving you money.

Each month, like you, I have fixed expenses. To keep a roof over my head, to eat, to drink enough wine to get through lockdown… you get the picture. Time on this earth costs you money just to live. Unlike salaried employees, entrepreneurs are tasked with the daily question of ‘how am I going to pay the bills this month?’.

Precisely when you have no income coming through is when you need to invest in a coach, because something clearly is not working.

A coach will help you overcome your blindspots, change behaviours that are holding you back and find creative solutions to old problems.

If nothing changes, nothing changes.

I think of working with a coach a bit like a cheat-code on the game Sims. You still have to play the game (eat, sleep, work, repeat) but you’ve got a leg up and are operating in a different mode to everyone else.

Coaches help you find answers to your most pressing questions. They help you stop going round in circles, and keep you accountable to doing what you said you will do. They help you make quantum leaps in your thinking and decision making processes that might otherwise take you months or deliberation and analysis paralysis.

You can work with a coach with speciality supporting in things like sales, networking, productivity, social media, marketing otherwise. But the all rounders, those coaches who are professionally qualified in the discipline of coaching itself do not need deep subject matter expertise. They shine a light on your situation and help you see clearly what needs to shift, through asking the right questions, or sharing stories about what they have seen in their other clients.

As we can see, many of the best founders will have their coach on speed dial.

When you remain stuck for too long you begin to lose faith in your ability, and problems begin to seem insurmountable. An hour with a coach can unlock a week’s worth of progress. I believe this because I have seen it time and time over with myself (you can read about my own coaching experiences more here) and with my clients.

This post was originally written for The Ask newsletter — offering professional development resources and coaching for the tech startup ecosystem.
Subscribe here for bi-weekly editions.

And to find out more about The Ask’s Founder Ellen Donnelly or apply for 1–1 coaching visit www.the-ask.uk

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Ellen Kate Donnelly

Founder & Chief Coach @ The Ask | Design your entrepreneurial path around you |