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Taking rest after you step down as a CEO
Taking rest after your step down is too important to be left to chance
As a coach and a former CEO of a venture-backed business myself, I guide startup founders through the critical transition from founder to CEO as their startups scale — or help them exit gracefully with a renewed sense of purpose and peace of mind. Taking your seat as a CEO is not a path suited for every founder, but for a business to grow, founders must evolve alongside it.
In my essay What's Next For You After Your Startup? I wrote, "After you leave, you'll almost certainly need a break to rest and recover, 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."
A client of mine, let’s call him Oscar, stepped down after more than a decade running his business that is now led by one of his most trusted executives. When reflecting on his next step, Oscar admitted that his biggest risk is jumping into something new without taking time to reflect and recover. The habit and inertia of being constantly busy, productive and surrounded by people can be a very powerful force, pulling us back into a familiar environment.
The constant busyness of running a startup often prevents us from even realising how tired we are. We are so used to masking how we feel with being busy, being caffeinated and being focused on the next big goal, that we may even start forgetting what it’s like to just feel how we are in the present moment.
As founder CEOs, we are always focused on optimising our time, figuring out whether we’re doing the most impactful thing. Our sense of identity merges with the business we founded. We may feel guilty spending time on anything other than the business, including health, family and friends.
Tom Savage, a British serial entrepreneur, describes his experience:
The moment you take away the responsibilities of being a CEO, with the accompanying adrenal fuel, you realise quite how stressed you were. I look on at others running the show and wonder how I lasted so long. I feel, for the first time in a long time, like I have space in my life to meander, to talk to people in the street, to engage in relationships without feeling like I should probably head back to my desk to forge on.
Every startup founder who stepped down as a CEO that I know recommends taking time to rest, reflect and plan next steps after stepping down. How long? Longer than you think you need. If you spent years running a startup, anything longer than 2 weeks may feel like a very generous amount of time off, because that’s probably as much as you’ve taken as a holiday in one go as a CEO. However, whatever the right answer is in your circumstances, it’s probably measured in months, not weeks.
At first, you might feel the freedom — and maybe terror — of not having anything scheduled for the day and not watching every hour of your time. A few weeks in, if you let yourself rest, you may start becoming more aware of how tired you actually are and may feel itchy to jump back into action to avoid this discomfort.
Meeting your fears
You will meet some of your fears. Maybe there’s an inner voice that says that your next act won’t live up to the success your business enjoyed so far. Or, maybe there’ll be a fear that you’re losing status in your professional community, if you’re in between two stages for too long. These fears will also make it tempting to distract yourself with work.
If you resist these temptations and think systematically about what’s next, eventually you’ll find yourself in a place where you feel rested, clear about what you want to do next and energised to go for it.
For me, this period of rest coincided with moving to another country, from London to Portugal, and exploring what the coastline has to offer. Instead of jumping back into action, I gradually eased into it by first starting part-time training as a coach, which I long planned to do, and started coaching my first clients, part-time, gradually increasing my workload as I was getting more and more confident that it’s the right next professional step for me.
I’m yet to meet a single founder CEO who leaves their business after running it for years and is bursting with energy, ready to tackle a new challenge. Doing any intense job that involves long hours, stress, responsibility and risks will take its toll, unless we learn to make it truly sustainable, which — as I know from working with my founder clients, as well as my own personal experience — is easier said than done.
So, if you can at all afford it, allow for time off after you step down. Whatever you choose to do next, it will benefit from you feeling like you’re ready for the challenge and are not simply avoiding feeling how you really feel by being busy.
Reflecting on our coaching conversations with Oscar after he stepped down, I noticed that we started talking less about managing his relationships with the board and more about how to be fully present to his family on holidays, after years of being glued to his work inbox at all times.
Making space for deep rest
A warning sign that you may need some deep rest is inability to stay still and do nothing for a while. By doing nothing I don’t mean watching Netflix and then going clubbing with friends, but being able to enjoy slow, quality time in nature or in meditation, in the presence of your own thoughts and feelings and without trying to distract yourself from them.
It can be difficult. We spent so many years working on the business, thinking about the business, thinking about ourselves as the founder and CEO of our business, that not doing it can feel like looking into a deep abyss. It’s ok to be disoriented as we’re learning how to reconnect with ourselves and discover who we are when we are not running a company.
This process of recovery can take time, reflection and deep conversations with others who’ve been there. We can’t know how much time it will take, but the promise is that in time we’ll start to rediscover ourselves and get comfortable in our own skin.
An even bigger promise is that the next big step in our career that we’re about to make will be informed by this understanding instead of being made on autopilot, without having had a chance to deeply think how we want to spend the next decade and even the rest of our lives.
A sign of deep rest is inner peace that we enjoy when we are simply being, without doing anything or going anywhere. This inner peace is the foundation for freedom, because we experience peace when we are not being compelled to do this or that. This inner peace allows us to face our thoughts and feelings, even if they are challenging. Then we can choose what to do next from a place of strength.
Two common traps to avoid
Rest doesn’t happen on its own if our minds and bodies are used to the fast pace of a startup environment. There are two common traps to fall into. One is to continue doing what’s familiar: reading industry news, networking with other entrepreneurs or joining panels at events — things you never had enough time for as a CEO, but which are familiar to you.
Another is to drift off into sloth and torpor, watching Netflix in the morning and then wandering aimlessly around the golf course, wondering why it feels empty inside when you’re having a 4pm pint.
Either would be a mistake. Rest may be the opposite of work, but it would benefit from discipline and a structured approach. It’s easy to imagine that once we are not running our startup we’ll finally have time to exercise, learn a new foreign language, travel to see our friends and go on a meditation retreat, but the truth is that unless we plan what we want to do and how we want to do it, we run a risk of slipping either into what’s familiar or into what’s easy.
Taking deliberate rest
So, how would you like to rest? What is most important to you about this period of your life? How would you like to balance health, learning, self-care and pursuing dreams you never had time for?
What would you like your self-care routine to look like? What things like, maybe meditation or tennis, you always wanted to learn, but never had time for? What books have you wished you had time to read? How much screen time would you like to have per day?
Schedule things. You ran a startup for years, and so you are skilled at setting goals, reflecting on desired outcomes and following your schedule. Make use of your professional habits to apply them to this period of your life. As founders and CEOs, we set goals, execute strategies and reevaluate them based on the results. Exactly the same approach can and should be applied to rest.
For example, for me it was important to enjoy a daily outdoor activity, e.g. a long walk, something I didn’t always have time for as a founder. It was also important for me to start training as a coach, so I signed up for my first coaching course and started working with my very first clients. Oscar, the founder who stepped down as a CEO to rest, recover and choose what’s next, started a big DIY project at home, rediscovered his passion for sports and spent more quality time with his kids than he ever did as a CEO.
One area that often doesn't get enough attention when we're running our startups is relationships. What would it be like to really spend more time and be present with our children and our partners? When was the last time we came to visit our parents and had as much time as necessary to listen to their stories? When did we last take time to take our nephew or a niece for an afternoon or a weekend in a theme park? Would some of our friendships benefit from late night conversations or weekends away?
The reason to ask ourselves all these questions isn’t just to give ourselves an opportunity to enjoy and strengthen our relationships, but also to discover who we are. Our identities, the way we experience ourselves are shaped by what we do and who we spend our time with.
We understand ourselves through our relationships
Our sense of self is deeply relational. I challenge you to say much about who you are without making a reference to something external: founder of a company, citizen of a country, expert in some field, fan of something or someone, parent of a child, partner of someone else. I can't even explain that I'm a man without talking about how different people have different genders. We define and experience ourselves as a reflection of our activities and our relationships.
This is why there’s a world of difference between navigating the transition as a CEO without reflecting on yourself and your values, and doing the same while being immersed in old and new relationships, making new experiences.
When we step down as a founder CEO after a decade of running our business, we may feel that this is the only thing we can do now and the only path forward we see. Our sense of identity and possibilities is limited by the intensity of our experience. Taking rest and proactively taking steps to reignite our relationships and expose ourselves to new experiences can be a mirror in which we may better see who we really are and what’s next for us.
What are some of the big things that you never had time for? Have you ever dreamed of walking the Camino de Santiago de Compostela in Spain together with other pilgrims? Or riding your motorcycle across a continent? Or dedicating a lot of your time and energy to helping a charity? Or taking a long meditation retreat? Or taking your family on an incredible adventure that you always said you’d do one day? Or maybe taking a sabbatical to write a book?
However you decide to rest, my invitation for you is to be deliberate about it. Resist the temptation to jump into something familiar, like accepting the first decent job offer coming your way. Resist the temptation to do what’s easy, because you might not even notice how this incredibly precious period of your life might slip through your fingers. Approach it with care, positive intention and a sense of gratitude that you have an opportunity to stop and ground yourself while you are thinking about what’s next.
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 firstname.lastname@example.org. And if you know someone who might need this, forward them this essay, they'll say thank you.