Sometimes, the best advice to give someone is to tell them to give up. Plain and simple. Stop. It’s not advice you can give without someone asking your opinion, or without the facts. When I think someone is in need of being told to give up, my main point is that by removing a bad project or focus, my friend will regain themselves, and in so doing, will enable their next thing to be a success.

Much has been written about the Art of Failure, to the point where it is held up by many as standard practice for those of us who work in an experimental way – failure is just a part of the process. I’m a pragmatist, not an idealist, when it comes to giving things up, however. Not everyone has read or been exposed to the idea that failure is okay, so sometimes you have to sit someone down and explain it right from first principles.

If you’re in a situation where your friend is doing something and you think that perhaps they’re on a hiding to nothing, or indeed if you’re feeling jaded, worn out, broke and downright depressed about what you’re working on, I hope the following will be useful:

Listen to yourself

A simple measure to know if you need to kill something, is to be aware of how you’re feeling when you’re talking about the thing you’re working on. In giving the latest in a long line of elevator pitch summaries to a stranger, how are you feeling? When you’re talking to friends, are you excited about other things, and when asked about how it’s going with your main thing, do you deflate, feel flat, change the subject? How’s your body language when you’re talking about it?

I had the realisation when I was running a small business a few years back, that when I spoke about it with others I was muted, stressed and not myself, but when I talked about other things I was doing in my spare time, I brightened up and was excited, interesting and a better person to be around. That’s a strong sign to give up.

The numbers aren’t adding up

The financials, or the key numbers for your project are upside down

If there’s more going out than coming in; if there’s no sign yet that at some point those numbers are going to work out; if the plan was to have profitability by this point, but it’s way off the mark; or indeed if any Very Important Number is off by an order of magnitude, it’s sign that change is needed.

If your Very Important Number is wrong, ask yourself if it’s time to change things around, reassess some core assumptions, plans and principles, or indeed to stop and do something else.

The “numbers” here might be financial – it could be some other metric around what you’re doing. Paul Birch, my co-founder often talks about things that he tried before the dot com viral success that was Birthday Alarm. His metric was a “viral coefficient above 1". As in, for each person that joined, for the product to be successful they had to get more than one additional signup. Get that number above one and you have steady growth. Get that number below one and you’ll be spending money on advertising, or indeed, considering giving up.

Get outside evaluation

When you’re focusing hard on a project, startup, idea, whatever it is, it is very, very easy to get into tunnel vision mode. Looking back on my past failures and the difference between how I thought about the world before and after I quit, it’s remarkable how strong an effect that is.

Each time, there was an important, influential conversation with someone who raised some of these questions, and it’s through having a trusted advisor there at the right time. If you don’t have that person, ask someone close to you to refer you to someone. Everyone knows someone, and people will want to help you. You’ll be surprised.

But, but, but…

Giving up is hard. “I can’t just give up!” is the obvious response to someone like me saying “why don’t you just give up?”

There are a thousand reasons for continuing with something past the point where you should. And failure can have serious downsides. It might be that it really is impossible to “just stop” – the bank might have a charge on your house, there may be serious repercussions, perhaps bankruptcy involved. If you think that’s the case, stop reading this and go and get some advice from a professional.

A case of mis-staken identity

However, many of the “buts” can turn out to be fictional. The main one being “but I’ve staked my reputation”. It’s the mis-staken identity. You, and your project are two separate things. People re-invent themselves all the time, and I’m often surprised when I hear of someone who worked on a business idea that didn’t work out springing back a little while later with something new.

Rip off the plaster

Many things are iterative – slight improvements here, incremental growth over there. Yet some things are step-change events, and there comes a point where something must be done. A “give up” decision is one of those, and for many people, it’s like ripping the plaster off a wound. Painful, yes, but if you don’t change the plaster, the wound will take a long time to heal. In giving up on something, and making a harsh, difficult decision, and doing it quickly, you may experience something similar – some pain now, but less drawn out over time.

Atychiphobia-light

Atychiphobia – the fear of failure is a real thing, and must be devastating to those afflicted. When I speak to family members, and to people who don’t, like me, read about experimentation and failure, or are just not exposed to startup culture, I often feel like I’m talking to people who have a light version of that phobia.

I often wonder what that effect has on people who are trying things, taking risks, or being experimental. Are people who don’t take risks the right people to listen to when things aren’t going well? Should you surround yourself with those people, or others who are more open to talking about things that aren’t working, as well as the success stories?

I think it comes down to promises – you’ve made a promise in some way that what you’re working on is The Big Thing, and when it’s clearly not working out, it’s very hard to say “it’s not working” to the same people to whom you’ve made that promise. Personally, I’ve stopped making those kinds of promises, and I’m telling my family that “well, you know it might not work out, but I’m going to do my best to make sure it does”.

Because if you’re thinking about quitting, perhaps you don’t need a conversation where you’re encouraged to carry on going, by people who are scared of failing themselves. In the past I’ve been wanting to quit something, but because of the influence (or encouragement) of those around me, I’ve kept going. Yet what I should have done was to have given up earlier.

What if?

As well as “but… but… but…” there’s “what if?”. What if I gave up now and then someone else did the same idea and got rich? What if I just keep going another month – that important contract might come in? Sure.

Nobody can see the future, but how realistic are those things? If you think about it coldly, it might be that you’re clutching at straws, and next month you might be in an even worse position.

Opportunity cost

Doing the wrong thing in place of the right thing means you’ve missed out on that opportunity. What has it cost you?

I spent several years working on a company – a little design agency. It was stressful, it was hard, we measured our success on winning a bunch of awards, yet we weren’t making enough money and it was a good candidate for “give up”. The trouble was, that politically those around me were all trying to make small businesses like mine a success – I’d fallen into an agenda about the city that I was in. And the one piece of advice I needed to hear was “Stef, what the hell are you doing? Just give up”. Perhaps some people did tell me that, and I didn’t listen.

Perhaps I needed someone to give it to me straight. In the end, it comes down to opportunity cost: if you spend your time on the thing that’s not working, you’re not spending time on the thing that might.

I don’t think I “wasted my twenties”, but I do wish I’d ejected earlier.

In the end, I did quit. And gosh is it hard. It’s horrible to shut down a company, to tell your friends it didn’t work out, to do a deal with the bank to pay off a loan from your personal account for years to come.

It turned out that, in the city I was in, that there were a fair few failure-phobes, but not as many as there are people who respect you more for trying and failing than taking the easy, dull path.

And much more horrible than the experience of failure is the prospect of being locked into something that’s not working out, and just keeping on going, getting more and more dragged down in the process.

Zombie fails

The thing is, once you’ve made that tough decision to stop doing something, that’s it. You can move on. The act is complete. Conversely, if you continue, the effects of staying stuck, and doing the wrong thing are with you every day until you finally do quit.

My other co-founder Nick Marsh pointed something out to me the other day. It’s not the mega-fails that you need to watch out for. It’s the zombie-fails. It’s the things that you do, that aren’t quite working, but are always showing a bit of potential. The things that always require of you to just do one bit more because that’s the thing that will make it go big. Except you do it, and it maybe improves a bit, but there’s another just one bit right around the corner.

Building failure into the plan

I’ve had a couple of “give up” occurrences since, and a win or two, because I’m being deliberately experimental in the way I work. Failure is built into the model at Makeshift – we try stuff out, we kill things if they’re not working, we follow through on the things that do. Our process is that we come up with a series of ideas, pick one that we think might be a useful digital service or product, and then we do a short hack. Each hack being a one- to two-week piece of work to build the smallest part of the idea (The Little Big Idea).

We try to get that little hack in front of people quickly to get feedback. At the end of a few days or weeks, while trying to see if people like the idea, we coolly look at the results. Are we getting any good feedback? Do people like this thing? Is it really something we want to invest our time and money in? Or do we kill it?

Sometimes it’s the latter. We say “that was an interesting experiment”, and go onto the next thing. Or if it’s looking promising, then we invest in building it into a real thing. And repeat. It’s learning by hacking. In order to do that you really have to be able to care about something quite a lot, to work hard on it, and then quite abruptly be able to quit.

Your biggest asset

It is, in my opinion, wise to hedge your bets until you find something worth spending your time on, and then have the required laser-like focus to jump on it and follow it through. Until then, it’s about making sure you use your limited assets wisely.

And that’s the main thing. If you’re stuck, it’s important to try to regain freedom, time, and space to do the next thing. By giving up on something that’s not working, you regain your biggest asset – yourself.


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I’m @stef on Twitter. Written with the help of #sundaypost, the kind folks who reviewed my draft and everyone who voted for this post on Help Me Write.