Entrepreneur Envy: Why We Can't Let Jealousy Over Others' Careers Get Us Down

Looking at Forbes' "30 Under 30" list makes me feel awful. I imagine it must be how a housefly feels looking at a bumble bee; far less impressive, and confused as to why she’s the one sitting in shit all day.

Maybe I’m being overly negative but reading that list (a who’s who of "entrepreneurs, innovators and game changers") doesn’t fill me with admiration, it fills me with self-doubt. I wonder to myself, 'Why don’t I have my own organically brewed coffee company/solar-charged sex toy business?' Why, at 24, have I not “changed the game”?

I love my job; I mean, I really love it and yet there’s this growing feeling that I can’t shake. It’s a sense of inferiority that in the past three years has reached a peak because of the time I’ve spent fruitlessly comparing my life to that of entrepreneurs. I’ve gone down a social media black hole, stalking the Instagram profiles of young business-owners. I’ve spent too much money on "how to run a business" books, which now serve as lovely coffee mats because reading them just makes me anxious. I’ve been too self-critical and allowed the nagging voice in my head to tell me that I’m failing, while knowing full well I have one of the best jobs going. Why does working a 9-5 now feel so second-class? I’ve wondered if I’m overly ambitious – and perhaps becoming an entrepreneur isn’t such a big deal for most people – but it turns out I’m not alone: in a recent study, 39% of millennials said they want to work for themselves.

So here’s the truth of it. I and many of my friends are sufferers of what I'm terming "entrepreneur envy". The symptoms include mental discomfort, a minimised sense of self-worth and a warped perception of other people’s working reality. It’s a generational epidemic fuelled by the filtered Instagram accounts of entrepreneurs and numerous articles that wax lyrical about getting rich quick.

While entrepreneur envy may be a relatively recent affliction, having your own business isn’t new. What is new is the ability to show the whole world the great perks that come with it. The days spent working on yachts, the branded baseball caps, the breakfast meetings with all the avocado toast we millennials could desire. Perks that make an outsider like me scratch my head and wonder where I’m going wrong.

There is, however, an antidote to entrepreneur envy, which I went in search of after reading an article claiming that one-third of entrepreneurs have work-related depression. Reading this made me realise that not only was I putting an unhealthy amount of pressure on myself but also that the lives of entrepreneurs can’t be as perfect as I had thought. So I decided to give myself a big cold dose of reality by speaking to three women entrepreneurs, to get a no-nonsense idea of what it’s really like to go it alone. As suspected, it’s not always as glamorous as it seems.

Rosie, a 25-year-old tech founder, has set up an extremely successful company which allows you to rent out your belongings for money. She isn’t taking home much of a monthly wage currently but is waiting for the big payoff when she sells. On the surface, Rosie’s life would be a classic trigger for entrepreneur envy. She loves her job, she’s young, successful and now living in San Francisco. However, she is the first to admit that being an entrepreneur has its downsides.

“Many people start a business because they’re tired of the 9-5 but you really don’t get any extra freedom. I now work 24 hours, seven days a week.” Chatting to Rosie reminded me of a time we were at a friend’s birthday party together and she showed me the hundreds of notifications on her phone from customers asking her questions. I remember watching as, glass of wine in hand, Rosie scrolled through all of them on Saturday afternoon. Unlike me, Rosie can’t just leave the office on Friday and switch off. Fifty-four percent of millennials who want to work for themselves say they want more flexible working hours and yet, in Rosie’s case at least, becoming an entrepreneur seems to result in less flexibility.

The second entrepreneur I reached out to was Katie, a 25-year-old designer. She studied design deliberately to give herself a practical skill to monetise and had always planned on having her own company. After working for a startup for a while, she now works for herself and has doubled her salary. She says, though, that she’s tired of friends thinking that she spends all day in interior design stores and at well-catered parties when in fact it’s the opposite.

“People beat themselves up for working in an office but being an entrepreneur still involves being tied to a desk. The obligation to be in front of your laptop is even stronger, if anything – only a tiny proportion of what I do is out of the office."

Katie admitted her own Instagram account is misleading: “Followers will only see one side to my work, which is the side I think the world cares about seeing.”

While this might seem obvious, it’s so easy to forget that we can crop, filter and edit our work lives. All those breakfast events are no doubt followed by many networking emails and even longer to-do lists.

“You should look a little harder at the photo of the guy working on a yacht and ask yourself, 'Why is he having to work there in the first place?'" Katie says.

And she’s right.

Next up is Camilla, a recent convert to the entrepreneurial world. Camilla is still working full-time at an advertising company but manages her own business selling Persian and Moroccan rugs on the side. She deliberately hasn’t taken the risk of making her business her sole income yet and she’s only just turning a small profit.

She says the process of setting up her own business was, at points, a lonely affair.

“I didn’t tell my work colleagues that I was setting up the business – to be honest I didn’t want them to think it was a joke. When I launched the website I actually just celebrated by jumping around my living room with my boyfriend.”

The idea that being an entrepreneur might be lonely seemed at odds with everything I’d read. What about hiring a team of your pals to work for you, or all those networking soirées at trendy hotels?

Rosie agrees that this is not a representation of your wider life. “Your friends find it very tough to understand why you can’t meet them at 8pm for dinner because you’re having to work until 10pm every night. It completely changes your life and you’re going through that journey on your own.”

Now, it should be said that some of the most successful companies in the world were founded by one or two people with a vision. If Ed Catmull had been scared of spending time alone then we wouldn’t have Pixar, and Steve Jobs would never have created the iMac. However, if you’re like me and love to be surrounded by a big team then think twice about striking out on your own – you’re embarking on a long solo journey before you can add more seats to your office.

One of my main reasons for envying entrepreneurs is the money they seem to earn for doing what they love. Ninety-two percent of millennials agree that money is a main consideration when looking for a job. However, we need to change the narrative about entrepreneurial cash flow – 90% of startups fail, that’s the reality and that makes becoming an entrepreneur one of the riskiest financial career moves you can ever make. As Katie says: “You won’t have the security of sick pay, pensions and a steady income for a long time. Don’t let this put you off – we need more female entrepreneurs – but don’t make any rash decisions.”

If you still want to start your own business, then Katie advises creating a buffer for yourself. “I would save around three months' salary before you quit your job. I made sure I had enough money to cover my rent for the year in case I couldn’t turn a profit.”

A recent study revealed that the average startup costs £22,756 to run in its first year. While it can be done for less (Julie Deane, founder of The Cambridge Satchel Company, started with just £600), realistically it’s going to be a long hard slog before you’re back to financial security.

Probably the most important thing I learnt from chatting to these women was that entrepreneurs are still envious of each other. Rosie puts it bluntly: “I absolutely still get jealous of other people and I have my own business. Now I just look at other people who own startups and think, 'Why are they doing better than me?' I have a friend who always seems to be promoting her business at festivals… I’m sitting there thinking, 'Why am I not always partying?'"

This may sound a bit like Beyoncé comparing herself to Taylor Swift, however, it’s an important point to make. Becoming an entrepreneur can be extremely stressful – it’s a move that many people consider and calculate, and only a few people succeed. An article by Inc. magazine gives a rather brutal look at the psychological effects of socialising and working in the startup scene. In it, the CEO of a successful startup describes eight months of constant anxiety, sharing $5 bottles of wine at dinner and preparing for his wife to give birth to their first child before he got his business to turn a profit.

As human beings, we will always find someone else to compare ourselves to. It’s an inferiority complex that is bad for our health. Right now, I might envy people who own their own business but only 10 years ago I would have envied the lawyers and doctors who had a steady supply of customers throughout the financial crisis. In 50 years, I will probably envy the people who were smart enough to buy property in Newcastle, which will no doubt be a London borough by then.

So this is my final ask: let’s try and eradicate the dark side of entrepreneur envy. Let’s remember the grass isn’t always greener. It’s okay to have a career – you can flourish and succeed in a big organisation and going it alone does not always equal success. I would still love to own my own business one day but now I can approach doing so with all the facts, and so can you.