The Happy Entrepreneur

Is a ‘happy entrepreneur’ a misnomer?

Being an entrepreneur is hard. Really hard. Or, in the words of Elon Musk, “Being an entrepreneur is like eating glass and staring into the abyss of death.” If that’s what it’s like when it’s working, given Elon is one of the most successful entrepreneurs alive, what hope do the rest of us have of enjoying it? Ouch.

I’ve spent a lot of my career recommending people become entrepreneurs, but sometimes I hesitate. At times I’ve coveted a 9-5, well-paid, corporate job. Admitting that, I feel a bit like a traitor to my vocation. Like David Attenborough suggesting he’d rather be an endangered species taxidermist. But the more I learn and talk to others, the more I learn that this is normal.

In this article, I want to address some of the things that I wish I’d known, or learned, sooner on the entrepreneurial journey. I believe there are ways to be happy as an entrepreneur, yet very few of us are and it requires even more work and focus to become one. 

Why Entrepreneurship?

Entrepreneurship is, in many ways, amazing. There’s something captivating about it; it’s empowering, creative, exciting and addictive. It’s a powerful, if not revolutionary, force in the modern world; with an intoxicating Schumpeterian ‘Creative Destruction’ occurring at rapid place in the music, media, hotel and taxi industries, to name just a few. As parodied in HBO’s fantastic Silicon Valley, entrepreneurs aim to “make the world a better place,” (and sometimes they even do)!

Despite how hard it is, it’s rare that people go back to a corporate job once they’ve tasted life in a startup. Yet for all of the media glamorisation, it’s often deeply unhealthy, stressful and – particularly in the tech sector – entrepreneurs have an extraordinarily low probability of success.

Probabilities and Hardship

By way of example, Google has 56,000 employees and more resources and freedom than perhaps any other company in terms of innovation. In 15 years it has come up with just one monetisation technique that contributes to ~95% of its revenues. Just one.

At the other end of the spectrum, 80-90% of startup founders that receive venture funding don’t exit with more than their (usually dramatically reduced) salaries. Just 0.1% of pre-funded tech startups ‘succeed’. That’s a terrible compensation for the stress and impact on their lives. The resulting psychological impact can be extreme, as these articles demonstrate:

Founder Depression by Sam Altman

Brad Feld, Depression 

Business Insider, Founder Suicides

The Journey

This photo, of the Wholi team on a retreat in Italy, fairly neatly sums up the journey...
This photo, of the Wholi team on a retreat in Italy, is a fairly good representation of the startup journey…

Given the difficulty and unlikely success, it’s important to try not to base all of one’s happiness on a result. One of our values at Wholi is enjoying ‘the journey’ – meaning that we want to enjoy the process and the day-to-day – regardless of the destination. Our values are aspirational as much as actual, a recognition of the things we want to be rather than necessarily the things we are. When things don’t go well – which they often don’t in a startup, it serves as an important reminder.

Mostly speaking, I have not been good at enjoying the journey, (Wholi’s journey is captured here on our Facebook page). I am beginning, slowly, to listen and act – to stress less and enjoy it more – with help from my team, peers and investors.

I am not transformed. The gulf between my ideal and actual self will always be there, but I am in the process of making some changes and I find writing one of the best ways to process, to understand and to set intention.

What follows is a (non-exhaustive) list of some things I’m working on and things I wish I’d done earlier, in an attempt to help others, or those starting out: 

Find out what you’re good at. Leave the rest.

I’ve only recently started coaching, so I can’t claim any Damascene moments just yet, but I am seeing glimmers. My coach tells me that his role is to find what people are naturally amazing at and help them find ways to focus those talents and leave the rest.

If there was a single piece of advice I could transmit to my teenage self it would, I believe, be this.

The issue is that what we’re good at often comes naturally, therefore we don’t identify it as a skill – we think it’s just ’normal’ – and as a result we don’t harness and enhance these skills into a super power.

One of my skills is empathy. I can often read a room, or a person, and am highly attuned to small cues, feelings, sensations and the emotions around me. Yet for many years – particularly throughout school – that empathy, or sensitivity was a weakness to be covered up, not a skill to be harnessed. I’ve spent far more energy trying to be tough than I have nurturing that skill and turning it into a superpower. Time to listen.

The ‘leave the rest’ bit is vital for entrepreneurs. The role often forces us to do a bit of everything. For me, I believe that has been destructive. Trying to be good at, or forcing the things that aren’t skills, has consumed a huge amount of energy in my life. Entrepreneurs often focusing attention on and believing that we must tackle every challenge. This is a mistake.

A initial closer analysis of my own ‘work’ has uncovered that many of the things that I’m best at, I don’t consider work and therefore I regularly feel guilty that I’m not working enough – even though by some measures I’m working a lot harder than I realise.

Certainly entrepreneurs will have to do things they’re not good at, but I believe that it is only by harnessing our natural strengths, focusing on them and recognising them – sometimes to the detriment of other ‘important’ things, or harnessing other people’s strengths to cover these – that we can truly be successful and happy; both in entrepreneurship and in life.  

Energy & Putting your own oxygen mask on first

Follow the advice about finding what you’re good at will transform (at least in my limited experience) one’s energy. If you harness a natural momentum, it’s easier to make progress.

If there was one measurement that would correlate with my being a happy entrepreneur (and therefore more likely to be successful), I believe it’s ‘energy’. Meaning how you feel on an energetic level — read this excellent HBR article for a better understand of what this means.

A friend (who’s also a coach) sent me this, claiming it’s one of the most important articles she has read when it comes to helping entrepreneurs. I agree. ‘Put your own oxygen mask on first’.

Entrepreneurs should be incredibly sensitive to their energy and foster it wherever possible. If you need to justify free weekends and evenings, just look at the HBR article in some more detail.

Founder Confidence

I’ve read a collection of articles recently about founder confidence and how often the brazen pitches and networking displays mask deeper, destructive insecurities that plague many founders.

Again, these tie into the previous two sections. If we find what we’re good at and leave rest, then focus on maximising our energy, we build confidence. Confidence is key. Entrepreneurs need to continually make decisions and hope they’re right. Often they won’t be. Yet we must have confidence. Study leading entrepreneurs – Elon Musk (despite how hard he claims it is), Steve Jobs and others and you’ll hear of a boundless confidence. I believe that confidence can be cultivated.

Get Support

Get help. Seriously.

Entrepreneurship is a lonely game, compounded by the need to present a positive, upbeat face to customers and your stakeholders. This exacerbates a failure to seek and ask for support.

Entrepreneurs need, desperately at times, to set up support mechanisms to help them. In my case a quarterly meeting with fellow CEOs where we ‘lift the kimono’ and describe what’s actually happening, provides some solace. Coaching, friends, team members, fellow entrepreneurs, networks, articles and other sources have too, but they need to be cultivated. Get over the issue of worrying that people will judge you because you have problems and ask for help. Lots.

I am still not very good at this, but trying to get better. Mark Suster wrote a great article about getting your mojo back here.

Finding Balance

Entrepreneurship is hard. So we put up with lots of hard things that don’t need to be so. A fellow entrepreneur I know gets up at the crack of dawn to catch early flights in order to ‘seize the day’. I believe it’s a huge drain on his energy and negatively affects his work. Another pulls an all-nighter once a fortnight, again, I believe, creating more of a deficit than a gain. As entrepreneurs, we should be looking for ways to make life easier, not harder.

I don’t schedule in early meetings, or fly late at night, or on weekends – even with an office in Romania. I spent a year carrying things to and from that office, before deciding to invest in two pairs of running shoes, two yoga mats, two sets of toiletries and so on. A small change, but my travel burden is a little easier. I try to ‘work like it’s the weekend. I worked from home for almost 2 years, before I realised it was much more costly to one’s emotional health than the expense of renting an office. My own battle with balance was the topic of my TEDx.

At Wholi, we have some role models who have found a semblance of balance. We love Richard Semler of Semco – his TED is here. Yvon Chouinard. 37 Signals, and Buffer. Whilst we at Wholi are in pre-product market fit phase, these companies have managed to grow into significant businesses whilst maintaining some balance and doing things differently. That’s truly inspirational.

If your life depended on it

There is a lot here, so much so that many of the topics could be an article – a book even – in their own right. Depression, stress, energy and so many solutions from meditation, sleep, diet exercise, therapy, coaching, holidays, avoiding things you’re not good at, mindfulness.

To sum up, if you were going on a polar expedition, you would be fastidious about your energy, your equipment and your health. While being an entrepreneur involves a lower risk of frostbite, it’s often a longer, harder journey.

If you’re an entrepreneur, treat getting this right as if your life depended on it. It does.

Sometimes we even go to cafes named after our values, just to remind us...
Sometimes we even go to cafes named after our values, just to remind us…