When (and why) to leave the business you built
In an extract from his new book, Do Start, Dan Kieran tells us — from first-hand experience as co-founder and former CEO of publishing platform Unbound — how to know when your work is done.
When I was making the decision to leave Unbound, I came across the Jungian idea that in life you have two adulthoods. The first is the one you live in reaction to your childhood and your upbringing where you work to prove to the world you are a success according to the definitions you accepted and absorbed when you were young. The second adulthood, which usually begins in midlife (I was 46 at the time I left the business), is where you develop the courage to reject the definitions and achievements of the first adulthood and decide for yourself who you really are and what those definitions should be.
I realised towards the end of my journey with Unbound that proving myself by being successful as an entrepreneur in other people’s eyes had given me the freedom to now define success on my own terms.
I don’t think it matters what the objective you set yourself is either. For some founders it’s a revenue milestone, for others it’s profitability, for some it’s selling and making a life-changing amount of money. Whatever objective you set yourself is the one that unlocks the truth of your journey when you reach it as long as you have prioritised your own growth as well as the company’s. Alongside evolving as an individual, my objective had been to get to profitability. Perhaps it was just a widely accepted benchmark in the VC-backed businesses around me that had stopped growing revenues exponentially, and needed to pivot to profitability. I don’t know. But when we started to be profitable on a monthly basis my daydreams returned. I realised then my own definition of success had been in my mind all this time. I just lacked the self-confidence to realise it. Being with my family, supporting the aspirations of the people I love, writing and teaching. I saw the business was not going to deliver those things for me. But I understood that the achievement of building it might if it had enabled me to develop the courage I needed to leave.
‘Proving myself by being successful as an entrepreneur in other people’s eyes had given me the freedom to now define success on my own terms’
You might take this as evidence that you don’t have to bother to make your ambitions come true because there is nothing meaningful at the end of them, but that’s not what I mean at all. No. It’s the process of setting yourself a goal and setting out to achieve it — the adventure, not the destination — that means you understand and recognise your own truth when you get to the end. However the end comes, which you won’t entirely be able to control. You have to push yourself beyond what you think you are capable of, to be able to believe the truth that is already inside you when you reach your goal.
Coincidentally — or perhaps not — working out our own definitions of success was the main bit of advice we got from Yancey Strickler, co-founder of Kickstarter, when my business partner John and I went to see him in New York on my second trip a few years earlier. He counselled making sure that we were going after our own definitions of success rather than anyone else’s. I had not seen the wisdom in his advice then, but I do now. And this, I have come to believe, is the real gold at the end of the entrepreneur’s journey.
Since leaving I’ve recognised that for me it goes further than that too. The urge to disrupt and open up access to the publishing industry was the vision for the company and was — and is — a burning passion inside me, but the desire to act and actually do it rather than moan about publishers in the pub was something more personal. I can see my aspiration to be an entrepreneur was another manifestation of my mental unease. Or perhaps dis-ease. When you think about it, most entrepreneurs feel inadequate. They don’t feel they are good enough in themselves. That’s why they have to ‘put a dent in the universe’ — in the words of the patron saint of tech entrepreneurs Steve Jobs — by setting off in search of these arbitrary milestones to prove themselves. They, we, are looking for external validation. We want to achieve something other people agree has merit. We want respect. Proof we are ‘good enough’ after all.
Living in the current version of the global economy, the path of being an entrepreneur seems to be the ultimate way to prove yourself that many people, like me, choose to set out on. But the external validation you were aiming for at the start doesn’t mean what you thought it would when you get there. And all the feelings you thought you would feel when you hit those metrics of success, which you are now not entirely sure you chose for yourself, turn out not to be there after all.
In the end I came to realise those feelings were always closer than I had ever thought. I can see and feel them when I look in the mirror right now, in fact.
They are in the smile of relief on my face. The peace I feel inside. And in the faces of the people I love, which I can now see, free of the prism of other people’s expectations I placed on the end of my nose in an attempt to prove myself to myself.
Which, I realise, I finally have.
I can also see that this state of mind I worked so hard to reach is just the current step on a journey I will spend the rest of my life progressing along. If you prioritise your own personal growth — pushing beyond the preconceptions you have of what you are capable of — in the process of building your business, you will arrive at this place too.
And trust me. When you get here, you are going to love the view.
Dan Kieran is co-founder of Unbound, the award-winning publishing platform that he led as CEO for over 11 years, taking the business from an idea on a piece of paper to a profitable, global company. Having stepped down in March 2022, he remains on the board as a non-executive director and now teaches on the Publishing MA at University College London.
He is the author (and editor) of thirteen books including the bestselling Crap Towns, The Idle Traveller and The Surfboard. He has given talks about his entrepreneurial journey at Google, The DO Lectures, Toronto’s Book Summit, London Book Fair, Hay Festival, Cambridge University and the EU Parliament.
Extract from Do Start: How to create and run a business (that doesn’t run you) by Dan Kieran. Text copyright © Dan Kieran 2023. Illustrations copyright © Mark Smith 2023. Published by The Do Book Co.
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