The hardest thing about entrepreneurship

Everyone tells you that starting a business is tough, but until you start it’s impossible to appreciate what a complete mental wrench it really is. Two and a half years in, we’re finally getting a handle on exactly why – and more importantly, what you can do about it.


Every day, I spend about a minute logging what I’ve done that day into idonethis. When I receive my daily “prompt” email, the service also includes a snippet of what I was doing exactly three, six or twelve months ago. And more often than I’d like, it makes for depressing reading.

While it’s great to be reminded of where in the world we were and what we got up to, the depressing part is what I entered for the “work” part of the day: often, it reminds me that I was working enthusiastically and diligently on something that turned out to be a complete waste of time.

It has the same effect as those “your domain name needs renewing” emails: they remind me of a project where I registered a domain in a flurry of excitement and maybe worked on it for a day or two, but it went nowhere and a year later had forgotten it ever existed.

This uncertainty and wasted time is exactly what makes entrepreneurship such a draining mental experience.

The uncertainty of entrepreneurship

When we’re asked about our lifestyle by people who’ve never done anything similar, they always fixate on how difficult the travel part must be – the logistics, expense, decisions and exhaustion. But as we always tell them, the travel part is easy, relatively speaking – even when you’ve managed to book an itinerary involving a Ukrainian budget airline that makes Ryanair look like the golden era of Pan Am.

The tough bit is building a business – which I’d always thought was because of the mental burden of being responsible for your own income, or lack thereof. But in fact, I now think the reason it’s so hard is that at any given moment, you have no idea whether you’re on the right track or pouring effort into something that will come to nothing.

Related reading: “Is my business a dud, or just taking a while to build momentum?”

Wasted time

The feeling that you might be wasting your time isn’t just a case of wondering whether there’s any demand for a speculative new business: even in clearly established markets, or in a business you’ve been running for a long time, many of your efforts won’t pay off. And although you might have an inkling one way or another during the process, it’s not until you’ve finished that you’ll find out whether your plans will fail or succeed:

  • If you’re a freelance designer (which there very clearly is an established and enduring demand for), you’ll need to work on ways to find clients. Some of those attempts will fall completely flat.
  • If you’re trying to build an audience through putting out useful educational material (”content marketing”), much of the content you create will go unnoticed.
  • Even if you’re creating a new product for an audience you’ve already established, you can’t be sure that your audience will end up buying it.

Like the old John Wanamaker quote that “50% of the money I spend on advertising is wasted; the trouble is I don’t know which half”, no business is immune from failed projects and initiatives. Even at Fortune 500 companies with the smartest people and decades of history to draw upon, tens of thousands of hours are collectively spent on projects, products or initiatives that come to nothing.

The difference is that as an employee of one of these businesses, although failure is still demoralising, you get paid at the end of the month regardless.

As an entrepreneur, an unsuccessful initiative means that you’ve invested your time, energy and emotions into something with nothing to show for it at all. It affects your bank balance, but also your self-worth and your confidence in your ability to succeed next time.

And, unlike a job where you need to show up for eight hours a day in order to get paid, it’s depressing to realise that you could have spent the entire day in bed instead of working hard and ended up no further behind.

Turning failure around

Actually, that’s not true – no failure is a total waste. At worst, you’ve at least eliminated one thing that doesn’t work so you’re more likely to pick something that does work next time. You’re also likely to develop or hone a skill in the process, learn something new about your market or audience, or have some kind of insight that increases your odds of hitting on a winner.

Over time, guided by our failures, we’ve become better about making educated guesses in advance about what will work and what won’t. Even the world’s greatest entrepreneur will never have a hit rate of 100% (Virgin Brides, anyone?), but ours is creeping up.

There are tactical things you can do to reduce the probability that you’re wasting your time – like pre-selling a product before you create it, developing an MVP so you can find out as quickly as possible whether people care about what you’re building, and relentlessly testing and tracking so that you can learn to focus on the elements of your work that make the biggest difference to the outcome.

But more important than tactics is learning to deal with the mental fallout of failed projects and wasted time.

Expect from the outset that entrepreneurship will be hard. Accept that like a company’s ad spend, 50% of your time will be wasted – but re-frame your failures so you’re focusing on what you’ve learnt from them. Don’t derive too much of your self-worth from how much money you’re making or how well your business is doing.

Understand that the correlation between effort and reward is extremely shaky, and entrepreneurship isn’t linear: you can spend years going nowhere, then hit upon a sudden “overnight” success that changes everything.

And when you do find something that works, recognise it for the rare and special moment that it is. Double down on it – and most of all, don’t forget to celebrate it.