What's next for you after your startup?
Leaving the startup you founded, whether by selling it or stepping down, is a major transition point in your career. Regardless of whether you became independently wealthy by building your business, the question of what to do next still needs to be answered.
It is a rare opportunity to take your career in a different direction, should you wish so. You have fresh experience, a strong professional network, a deep understanding of your industry and, most of all, freedom to make the next move. Good moments to change career trajectory don’t come often because to get really good at something we need to spend at least a decade doing it.
When you leave your startup, assuming you ran it for years and achieved a degree of success, you have a personal and professional platform from which you can pivot to something new without losing the progress you’ve made in your career. It's almost like a career "save point" in a video game, where you can go in a different direction, but you still have all the achievements, experience and self-awareness you've gained so far. Many people have such moments only once or twice in their careers, so it makes sense to use this opportunity wisely.
(After you leave, you'll almost certainly need a break to rest and recover, and we'll turn to this topic in one of the future articles, because it's all too easy to either waste this opportunity by doing what's familiar and not thinking outside the box or by doing what's easy, watching Netflix in the morning before a 4pm pint, wondering where the time's going. However, today we'll reflect on how to think about what's next.)
What's your idea of a life well lived?
I often ask my coaching clients about their idea of a good life. Many, or maybe even most, are surprised by this question, admitting they haven’t thought deeply about it. Yet, how can we live a good life if we can’t articulate what we’re aiming for? Of course, our idea of what a good life is will be constantly changing throughout life, which is healthy and shows that we are growing and evolving. Yet, not thinking at all about it leaves us at mercy of following social conventions and our own unexamined assumptions.
My own idea of living a good life involves helping others, meaningful relationships, deep conversations, being close to nature, simplicity and peace of mind. My idea of a good life is having a positive impact on the world and on the people that I know.
I believe that nothing in our life is an accident, but not in a sense that there’s some divine masterplan. Rather, what happens, happens for a reason and we can look back at these reasons, to discover patterns and valuable lessons.
In hindsight, it’s clear to me that I started Makers a decade ago primarily out of a sense of insecurity, aiming to prove myself and win imaginary approval from imaginary others by building something valuable. But it quickly became clear to me that what kept me working at Makers was an opportunity to help our students change their lives.
In our first year I coached students to become software developers myself. I saw them going from writing their first line of code to signing their first employment contract as a software developer within months. It was only in retrospect that I appreciated how meaningful that direct, personal connection was to me.
Likewise, looking back it was clear that once the business started to grow and my focus inevitably shifted from working with students to working with numbers and strategy, I started to further drift away from my idea of a good life.
For years I tried to trick myself into thinking that my work had an impact on plenty of students as we kept changing more and more lives at Makers, which was objectively true (over 5,000 lives changed and counting!). However, deep inside I knew that I’m not living my idea of a good life.
What is your life telling you?
As Parker Palmer beautifully writes in his book Let Your Life Speak, before we tell our life what we want to do with it, we should listen to our life for what it has to tell us. My life was telling me that something was not right. In retrospect, my one and only depressive episode when I was a CEO was there to shake me awake and remind me that something needs to change.
It’s not a surprise, in retrospect, that what helped me better understand myself were my own founder coaches with whom I worked over the years as a CEO. Session after session, year after year, they helped me go inside, reflecting on the questions that wouldn’t go away.
Who am I? What have I learned about myself in my life so far? What are my strengths and weaknesses? What skills do I bring to the table? What do I value? What gives me energy, and what drains me? What do I value most, as evidenced by my actions? What were the real, deep reasons for starting this business? What are my hopes and dreams? What are my fears?
Jerry Colonna, the founder of Reboot who led a CEO Bootcamp, a five day immersive programme for startup founders in Colorado that I attended in 2015, shared a Buddhist tale of Milarepa with us, 14 startup CEOs, sitting in a circle around a fireplace on a crisp winter day.
Milarepa, according to a legend, lived and meditated in a remote cave. One day he returned to it only to find it filled with scary daemons. They were flying around the cave, big and small, all of them repulsive and unpleasant to look at.
Keen to meditate in peace, Milarepa tried to throw them out, running after them, shouting at them. But the daemons wouldn't leave. It even seemed that new ones appeared all the time.
Realising the futility of his efforts, Milarepa then decided to teach them Dharma, the Buddhist wisdom. The daemons started paying attention and became quiet, but still wouldn't leave.
Taking a deep breath, Milarepa decided to talk to them instead, asking, “What are you here to teach me?” One by one, the daemons started sharing their lessons and, once satisfied that Milarepa heard them, left the cave.
Yet, one daemon stayed behind. It was the largest, scariest daemon that Milarepa was afraid to even look at. Realising he was powerless against this daemon, Milarepa went to him and put his head into his ugly mouth, saying, “Eat me if you wish”.
At this moment the daemon disappeared.
For me, the daemon that I was afraid to face for years was the realisation that my professional trajectory is taking me further and further away from something that’s deeply important to me, and that the business might be better off if run by another CEO.
"The only choice that doesn’t destroy you is to bring forth who you were meant to be"
In his book, Reboot: Leadership and The Art of Growing Up, Jerry writes about facing his own daemon, acknowledging that he wasn’t and didn’t need to be as rich as Bill Gates:
I wasn’t and—importantly, had no need to be—Bill Gates. Indeed, I often think of the teaching of Jesus. It’s a lesser-known teaching from the one of the Gnostic Gospels, the Gospel of Saint Thomas:
“If you bring forth what is in you, what is in you will save you. If you do not bring forth what is in you, what is in you will destroy you.”
Jesus taught a truth: the only choice that doesn’t destroy you is to bring forth who you were meant to be. The alchemy of becoming yourself is the ultimate magic act and fullest expression of leadership.
In all these thoughts I read a steady, consistent wisdom: the wisdom of knowing yourself and your own beliefs and living them. Enduring the alchemical crucible requires developing the capacity to reflect, to turn the pain of the everyday life as a leader into lessons. Every wisdom tradition I’ve ever encountered demands the same thing: we must go inward.
My own way of saying “eat me if you wish” was the decision I made in 2019 to take action: to start the transition to a new CEO at Makers and to a new career for myself.
Meeting my own daemons
Going inwards, reflecting on my own beliefs and when I lived or betrayed them, exploring who I was meant to be helped me realise a simple truth: I thrive when I have an opportunity to make a difference in someone’s life through a deep, meaningful connection.
Looking at what it means in practice, brought me time and time again to the idea of training as a coach myself. The simplicity and joy of being able to make a living by helping other leaders become themselves and live a life aligned with their inner truth brought forth another big daemon: What if I’m not good enough to be a good coach?
And that’s the daemon I’ve been courting ever since I started coaching others. My own way of putting my head into its salivating mouth is admitting that yes, I am not perfect. I’ve plenty to learn. I keep making mistakes. I don’t have all the answers.
And yet, I am walking my own path, waking up every morning aiming to bring forth who I was meant to be, living it through mistakes and successes, wins and losses, remembering that if I want to be a good coach by the time I’m fifty, I did well by starting this journey before I was forty.
My way of putting my head into the daemon’s mouth is trusting my own sense of who I am and what work I should be doing, instead of hoping that achieving a certain goal or making a certain amount of money is what will constitute a life well lived.
While there’s no easy framework to think about what’s next for you after your startup, I hope that these two questions will prove to be a good starting point. What is your idea of living a good life? What daemons do you need to meet on your way there?
Startup CEOs in transition peer group
Nearly every startup CEO thinks about stepping down at some point. Yet, almost everyone faces these two questions in solitude, because admitting that you're considering leaving your business is still taboo:
How can I decide to step down?
How do I prepare the transition?
I'm building a peer group of startup CEOs where we'll explore these questions together. This is for you if you are:
A startup CEO trying to decide whether to step down
A startup CEO preparing the transition to a new CEO
Here's how it works:
Meeting bi-weekly for 90 minutes
No advice giving, only sharing experience to see how others are navigating questions that torment us
Strict confidentiality expectations
No more than 5 founders and me as a coach and facilitator
Join and drop off at any point
Monthly fee invoiced discreetly (so that your finance team doesn't know you might be considering stepping down)
If you are interested in joining, drop me a line on email@example.com. And if you know someone who might need this, forward them this email, they'll say thank you.
Become a beta reader of my book
I'm writing a book on Startup CEO Transitions, helping startup founders decide whether to step down as CEOs and if so, have the best possible transition to a new CEO, because they have only one shot at getting it right.
The draft is embarrassingly rough, which is why I'm looking for beta readers to give me feedback on it and shape the direction of the narrative. Massive thanks to Victoria, Ian, Rob, Claudia and others who already signed up. Your comments and contributions have been invaluable so far!
Needless to say, you'll get a signed copy from me when the book is finally out with your name being acknowledged there :)
Email me on firstname.lastname@example.org if you'd like to get involved!