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#160 The best thing you’ve ever done is ahead of you and will always be ahead of you with Dan Kieran

Another Door Stories

Release Date: 09/18/2025

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Another Door Stories

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Another Door Stories

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“If you look back on your life and see that you would have done something differently, that means you’re wiser now than you were then. And that means, by definition, the best thing you’ve ever done is ahead of you and will always be ahead of you.”

 

What happens when you walk away from the thing that defined you, your job, your identity, your sense of success and step into a space of not knowing? 

 

In this episode, I speak to writer, entrepreneur, and all-around inspiring human, Dan Kieran. The co-founder of the pioneering publishing platform Unbound, Dan shares his story of closing the door and walking away from his creation, his vision, but knowing it was time to move on.

 

Dan shares the exhaustion of life as a CEO, the ego death that comes from letting go, and the unexpected joy (and financial precarity!) of redefining what success means on your own terms. 

 

So tune-in if you’ve ever wondered whether it’s time to move on, felt stuck in a life that looks “successful” on the outside, or craved permission to pursue meaning over metrics.

 

The Highlights:

 

04:07 How Unbound was created and the rollercoaster ride of startup life  

10:44 When the hot streak ends: pandemic, VCs, and knowing when you’re done   

14:55 Identity loss, ego death, and what’s left when the title disappears  

17:21 Carl Jung, two adulthoods, and why your second act is worth celebrating  

22:13 Why “not knowing” your next step is a huge opportunity  

24:05 Practical advice: preparing for change without a perfect plan  

27:49 Bringing your family (and your honesty) with you through change  

30:06 Autotelic living: doing things for their own sake, not just the external rewards. 



What helped Dan navigate change:

 

Soundtrack: Birdsong, especially blackbirds in the garden and forest. Dan recommends getting outside, into nature, as a grounding soundtrack for big transitions.

 

Book: The Middle Passage by James Hollis

 

One piece of advice: “If you look back and see that you would have done something differently, that means you’re wiser now. So the best genuinely is ahead of you, don’t let anyone (especially yourself) tell you otherwise. Back yourself.”

 

About Dan Kieran:  

Dan is the author of 14 books including the Business Book Award Winner - Do Start: How to create and run a business (that doesn't run you) where he tells the story of his own entrepreneurial journey with the publishing platform Unbound.

 

Having left the business in 2022, he now works as a Fractional co-founder with female founders and diverse teams who are building companies that will help create a more sustainable and ethical world.

 

Website: dankieran.com



Work with Eleanor:

Buy the Book - Another Door Opens out now. 5 steps for navigating change. Described as ‘Game changing’ ‘Brilliant’ ‘A must read’ ‘The best book on change’.

 

Eleanor supports individuals, teams and organisations through change. Whether it’s coaching or large scale organisational change through communications and training.

 

Work with Eleanor 121 as your coach, when you are starting something new, to develop the idea, to create the idea, to get it launched.

Book in a Change Mastery for a team session - when your team is navigating change.

Book in a 90 minute workshop - to think through change at work.

Join the Another Door Opens 5 Step Programme - a course and community to guide you through the mess of change to find calm, joy and opportunity.

 

 

Instagram:instagram/anotherdooruk

LinkedIn:https://www.linkedin.com/in/eleanor-tweddell/ 

Website: www.another-door-opens.com

 

Produced by winteraudio.co.uk