What is a Good Life? #88
Playing With The Edges Of Growth with Derek Sivers
On the 88th episode of the What is a Good Life? podcast, I am delighted to introduce our guest, Derek Sivers. Derek is an author of philosophy and entrepreneurship, known for his surprising, quotable insights and pithy, succinct writing style. Formerly a musician, programmer, TED speaker, and circus clown, he sold his first company for $22 million and gave all the money to charity. Derek is the author of Useful Not True, How to Live, Hell Yeah or No, Your Music and People, and Anything You Want. All his books, latest projects, and musings can be found on his website: sive.rs
In this insightful and engaging conversation, Derek takes us on a journey through his experiences as a musician, philosopher, circus performer, entrepreneur, and author. A journey spanning several continents that embraces, lets go of, and challenges multiple perspectives, and is underpinned by considerable explorations of growth, curiosity, joy, and play.
If you feel stuck in your way of thinking, stagnant in your current life, or tired of your perspectives, not only will Derek’s life serve as an incredible inspiration, but his thoughts and ideas may guide you to places you never imagined.
The weekly clip from the podcast (4 mins), my weekly reflection (3 mins), the full podcast (83 mins), and the weekly questions all follow below.
1. Weekly Clip from the Podcast
2. My weekly reflection
In this interview, Derek reflects on the process of writing his book How to Live, a book that lays out 27 ways to live. Each chapter suggests how you should live, and each chapter contradicts the previous one. For example, one chapter argues why you should be totally independent, keeping all options open. The next one suggests you should commit to one career, one place, and one person.
Now, I am a little torn about what I am about to write, as on one level, I suspect life may simply be living its way through us, and we can merely get on board with the flow of life and observe, paying attention to the present moment.
Yet, at the same time, there is undoubtedly a level at which I experience life where I feel there are different parts of me with different needs, and there are different chapters in my life, with different beliefs.
And it all seems true together. For example, I sense very deeply that we are all connected. And I am also very clearly aware of my own separate existence, dramas, experiences, and reactions to those experiences.
I often think our life encompasses a number of different chapters, or perhaps, more aptly put, lives within a life.
I was recently reflecting on my time working in corporate banking in my early to mid-20s, and the people I saw every day and with whom I built wonderful relationships, yet with whom I am no longer in contact. They almost seem like characters from a film I watched long ago.
Sometimes there are parts of this life that feel as though they belong to someone else.
When it comes to our beliefs and how we interpret this world, this life, it is as if we forget we are merely experiencing another chapter in our lives, and we fervently cling to ideologies rather than acknowledging that it is merely our latest interpretation of it all. Like everything that has come before, it will shift, twist, and turn again.
This made me think this morning of how, when I started meditating, doing silent retreats, and maintaining a fairly disciplined morning and evening practice for a few years, I began, in quite an irritating fashion, to suggest it to others as a cure-all, no matter what dissatisfaction they had just expressed with their lives.
That I would have found it inconceivable, almost a decade later, that I would rarely meditate, and that I’d most likely mock the silences I often inhabit and experience, and the extended times without a phone or distractions, as not enough.
How often do we cling to one way of living, convinced it’s the key to everything, only to find ourselves outgrowing it or it no longer being our way?
There is something incredibly human about clinging to a way of living and a particular unending life philosophy, as though it will somehow give us the answer, somehow protect us from the unknown and uncertainty of it all.
Whenever I meet someone new and mention this project —interviewing over 200 people on the question of what makes a good life— invariably they want to know what I have learned, and in some way, to glean an answer from it.
If you’ve followed this newsletter for long enough, you’ll know that offering a singular answer was never my intention. The only thing I can say with certainty is this: it will change. Even if you think nothing has changed, or that you haven’t changed, it will.
The following quote by Heraclitus always resonates deeply with me:
“No man ever steps in the same river twice. For it’s not the same river and he’s not the same man.”
Like the inevitability of the seasons, you too will experience phases in your life. From all the people I’ve interviewed, some plasticity of thought and beliefs, some openness to change, often allows this river of life to flow more gracefully. Rather than using all your might to build a dam that may burst or that cuts off your access to that river, this life, and to the possibilities of it all.
The capacity to hold our beliefs lightly, to be nimble and respond to our needs as they arise, and the humility to acknowledge that what we know now may not be all we know tomorrow, to admit we simply don’t know and are doing our best.
I don’t know about you, but that openness and looseness, the ability to eventually let go after I’ve once again clung on too hard (and knowing I’ll likely do it again), not only makes me feel more alive, more aligned to the moment, but it strangely brings me peace within the turbulence of this good life.
3. Full Episode - Playing With The Edges Of Growth - What is a Good Life? #88
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4. This week’s Questions
With any situation you presently face in life, what is the growth choice within it?
Is there anything you ever avoided or disliked in your life that you now find yourself loving?
About Me
I am a coach, podcast host, and writer, based in Berlin, via Dublin, Ireland. I started this project in 2021, for which I’ve now interviewed over 200 people. I’m not looking to prescribe universal answers, more that the guests’ lines of inquiry, musings, experiences, and curiosities spark your own inquiry into what the question means to you. I am also trying to share more genuine expressions of the human experience and more meaningful conversations.
If you would like to work with me to explore your own lines of self-inquiry, experiences I create to stimulate more meaningful group conversations, trust, and connection, or you simply want to get in touch, here’s my email and LinkedIn.
I agree wholeheartedly about change (it's taken me a lifetime to realise, sigh). I've been reading about Stoicism recently and it appeals. Oliver Burkeman's musings on time are good too, accepting that time is finite and that I'll quite literally never get 'everything' done is liberating.
I'm looking forward to listening to this one. Thanks.