To Quit or Not to Quit? That is the question…

…that keeps every entrepreneur awake at night!


Whether it is wiser to struggle on in the hope of better fortune
Or, to cut your losses and exit now before all capital and
Reputation is consumed?

But what comes of such a retreat?
What unintended effects might be unleashed?

Ah! There’s the rub!
There is no quitting from the consequence.

No, Shakespeare didn’t write this, but if he were alive today, he might have…

The struggle of whether to continue with your enterprise; to raise the investment and increase the stakes; or to pivot; or to cut your losses, is a question that rises in the morning as you wake and dies each night as sleep finally overcomes your raging startup thoughts.

When trusted voices — from successful entrepreneurs and high profile figures — like Simon Sinek are re-quoted telling you to ‘don’t quit’. Should you heed this advice or discard it?

In this article, I will tease out the truth of the ‘don’t quit /never quit’ advice, share my own experience of both quitting and winning and ultimately surprise you with a better offer on how to make the quit / don’t quit decision.

(Okay, if you are in a hurry — just jump to the end — and get the answer — but for everyone else, onward…)

Simon Sinek

So what did Simon Sinek actually say?

Don’t quit. Never give up trying to build the world you can see, even if others can’t see it. Listen to your drum and your drum only. It’s the one that makes the sweetest sound.

In fairness to Simon, he is saying — never give up being who you are — a world changer.

He isn’t actually saying, you must never give up on a particular business or a certain path to that change.

Understanding this distinction means that we can see the decision to quit some businesses or enterprises as about remaining true to who we are and what we wish to create. It isn’t really advice about quitting, although it is often quoted as if it were.

For example, the CEO and co-founder of Monzo Bank quit his role at Startling startup bank in order to launch Monzo. And similarly, many successful entrepreneurs have done the same.

A lot of good things come from quitting…new paths!

I Never Quit

Another recent source of ‘never quit’ advice comes from the excellent Upscale book by James Silver and the UK’s Tech Nation.

As a book it is a series of conversations unpicking what it takes to succeed — in this case, grow from startup to large (and often international) scaleup.

There are many diverse voices and opinions but one view that comes through consistently is ‘never give up’.

The trouble here is that we are only hearing from entrepreneurs who have made it, who are already successful, and hence, we have a horrible survivor bias.

What’s Survivor Bias?

Think of Survivor Bias like this. Everyone decides to stop eating for 60 days. Many people die but at the end, you interview the survivors and ask what they ate? Nothing. And that becomes your recommended survival advice…

The better question to ask of this post-successful group is — how is this advice helpful for someone or some team that is still in the process of building a successful company for the first time?

In truth, the quit / don’t quit advice of the successful entrepreneur isn’t very helpful. But more on that below. First, let’s talk about other people.

The Other People problem

Why do we feel the urge to tell other people — particularly junior partners, investors and people that rely on us — that we ‘just won’t quit’? Why do we feel this demonstration of confidence is so important?

Perhaps we believe that they depend on our certainty? After all, if you don’t have confidence in your startup, who will?

But often, a brazen certainty will tell more experienced partners — investors for instance — that you just don’t know what you are doing! After all, they have often been there and got a range of T shirts, so they KNOW that often you have to quit — because they have!

Okay, they don’t boast about quitting and that’s a pity. But many investors prefer a quiet confidence that you’re prepared to solve problems that you have not met yet and that you recognise that you don’t have all the answers. This is certainly preferable to a swaggering ego brimming full of self-importance.

Why we don’t boast about quitting?


That’s why we don’t boast about quitting. We’re afraid of shame. Or being shamed.

After all, who boasts about quitting?

Well, actually, if we want to help the next generation of startup entrepreneurs, it would be a great help if we did boast about quitting — or at least mention it.

I quit from a business which 18 months prior was turning over £4m and had received an offer for sale at £12m.

When we decided to quit we did so because we believed that our business model had died and come to an abrupt end. We weren’t willing to put our own cash into the business to ‘rescue’ it.

I also know lots of fellow entrepreneurs who didn’t quit in 2008/9. What happened to them? They put everything they had on the line, they set themselves up to be the hero and they lost the lot.

Yeah, it’s good to quit. We walked away with nothing but great memories and some great years.

We walked away well because we quit early.

There’s an important lesson in that. Don’t let shame, or perhaps a desire to be the hero rescuing the failing mission, get in the way of making the right decision.

And make your decisions early.

The right decision… which is that?

Okay, I don’t know what your ‘right decision’ is — but, usually it comes with a message that says this is gonna hurt! Or, you’re not gonna want to do this, but…

Do you have the courage to take it?

The Answer to the Quitting Conundrum

Tututtuarrah! Here it comes:

Great entrepreneurs quit and they don’t quit — both together, all the time, and at the same time, morning, noon and night.

Yes! The question of to quit or not to quit is a false one. You have to do both. All the time.

You constantly choose between various options, turns in the road if you like, hence, making choices and leaving options behind and closing doors (deliberately or inadvertently) is a part of the entrepreneur’s journey.

Hence, at the same time — you need to be both willing to quit at any moment and simultaneously, determined never to quit.

Yes, its a paradox.

Let’s call it the paradox of quitting.

You need to be absolutely certain of success and to demonstrate that confidence of success whilst changing direction and quitting all the time.

Let go of the quitting question and ask this instead — how do I make better choices….

Here’s the advice of Oprah Winfrey

Do the one thing you think you cannot do. Fail at it. Try again. Do better the second time.
In other words, be brave and learn to quit well so that you can go again!

Now, let’s get on with making some of those choices, taking action and yes, let’s do some quitting too.

Have fun!