Those who are compulsively attached to the results of action cannot really enjoy what they do. They get downcast when things do not work out and cling more desperately when they do.
I recently read the passage above and felt that it wonderfully captured one of the greatest challenges of company-building, one that seems so pervasive in the way many founders relate to their companies. When you commit to building a startup, you are wedding yourself to a path rich in ambiguity, rejection, and one that will never cease to remind you of all the reasons why things might not work out.
It only takes a quick skim through a couple of startup biographies, or conversations with a handful of successful founders, to realise that building a company is rarely a smooth ride. But, whilst the health of the company itself will inevitably fluctuate over its lifetime, I feel that one of the most pivotal questions for a founder is whether you allow your own personal well-being and self-worth to get dragged along for the ride.
Distancing from the spin cycle.
The metaphor I often have in mind is that of a washing machine. The intensity of the startup journey is reflected in each relentless wash cycle, and, as founders, we often find ourselves being thrown side to side throughout every successive spin. Since starting my company, I’ve been somewhat obsessed with the question: What would it look like and feel like to be able to step out of the machine, observe the events unfold, but feel fully at peace with whatever is happening?
The hardest thing about building a company.
Perhaps I’m naive at this early stage of our company, but I don’t believe that the hardest thing on this journey is to build a unicorn, or take your company public. From spending time with founders who have succeeded in doing both, I believe that the most challenging part of this venture is cultivating the ability to say: “My company had a bad day, and I had a great day.” I have met many founders who have indeed built incredibly successful ventures, but suffered deeply for years in order to do so, or worse yet, remain in a perpetual state of anxiety that their precious success will be stolen from their fingertips by any number of unforeseen or uncontrollable events.
“If you’re not anxious about your company succeeding, then it means you don’t care enough to win.”
One of the biggest hurdles lurking in the heads of most high-achievers goes something like: “I’ve only been able to achieve great things by consistently being hard on myself and using this state of anxiety as a fuel for greatness.” I’ve been a victim of this kind of self-talk for much of my academic and professional life, often subconsciously. I even feel this voice today amidst the discomfort of stepping away from work for a few hours despite a long list of to-do’s bubbling in the back of my mind.
It’s scary to imagine what exists on the other side of this anxiety: Fear tells me it’s a passive inaction that will stunt my (and my company’s) growth. Wisdom, however, tells me there is a force for greatness to be attained if one can dial down these sabotaging narratives. I am fortunate to spend a lot of time with a wonderful startup coach and dear friend, Alexander Volz. We frequently work on visualisation exercises of this nature which help me to feel and embody the ‘Jedi’ version of myself that exists on the other side of this fear. I’m increasingly convinced that the act of relaxing into whatever is happening can give rise to a state of focus, peace, clarity of mind, curiosity, empathy and creativity … which together provide a far greater driving force for building something outstanding than any fear-based motivations.
A less well-trodden path.
From my experience, there seems to be a severe lack of role models when it comes to entrepreneurs who have ‘let go’ of attachment to outcomes and yet continued to build successful companies. For many, this sentence alone will sound contradictory. But to be clear, I don’t think of ‘letting go of attachment to outcomes’ to mean ‘not caring whether or not you succeed’. I’m speaking to the dissolution of the belief that “my happiness depends on the success of this company” and how breaking this narrative can paradoxically increase the odds of ‘succeeding’.
I was deeply excited when a friend introduced me to the life story and work of Michael A. Singer – perhaps the single best example I’ve found of someone who dedicated his life to surrendering to whatever was happening at any moment and, in doing so, achieved greatness in many pursuits (including founding a software company which he took through to IPO). I love the following passage from his second book, The Surrender Experiment, which captures his commitment to using every challenge of his entrepreneurial journey as fertile ground for self-growth:
“I simply kept letting go. I used all these situations as a way of letting go of myself. I kept being pushed into strongly positive and negative situations, and I increasingly found myself in a very clear undisturbed state. It seemed that the more challenges life put me through, the less my inner energy flow was affected by outer conditions.
As long as I made getting rid of myself [his ego] my only goal, every situation was a fruitful experience. If I’d had any other goal, I think the constant pressure would have been overwhelming. I found that I actually got more peaceful inside, as I dealt with the ever increasing magnitude of challenges.”
Michael A. Singer
Easier said than done.
Over the past year, I’ve found myself sucked into ‘the washing machine’ on a number of occasions, and equally made my way out during several challenging moments. I wanted to share a few ideas and practices that I’m finding helpful in cultivating peace amongst the craziness of start-up life:
- Am I leading from above or below the line? In the book: 15 commitments of conscious leadership, the authors describe the helpful concept of leading from ‘above or below the line’. Leading from above the line is characterised by a state of openness and curiosity, often asking: What can I learn from this? It is the belief that things are happening for you. Leading from below the line means obsessing about ‘being right’. When we’re below the line, we remain closed-minded, often in a victim state, and hold the belief that things are happening to us. I’ve found the simple act of asking myself whether I am above or below the line in any given moment to be a very powerful first step in inducing a shift.
- Is there life outside of my company? Perhaps unsurprisingly, I’ve found very strong correlation between my tendency to get sucked into the ‘spin cycles’ with the length of time passed since I’ve taken a real break from work. Naturally, a startup will consume huge amount of a founder’s time and mental space. But, if weeks go by without truly switching off from work, it becomes easy to forget that there is in fact more to life than the startup venture. Committing to taking Saturdays as ‘free from work’ is playing a helpful role in breaking this otherwise dangerous pattern, and gives me more energy as a result.
- What kind of movie are you playing in? So many great films follow the classic heroes journey arc, characterised by inevitable challenge and ‘hard times’, but with an accompanying undertone of trust that things will work out. When you’re the main character, maintaining this broader perspective without getting sucked into the moment-to-moment is not easy. One exercise I’ve been attempting more frequently is viewing this journey, and my life my broadly, as a kind of film that I (my awareness) is watching play out. Imagine the book you want to write when you look back at the end of your life … through this lens, every challenge, drama and rejection add a richness and depth which make the path that bit more interesting.
- What is the most likely cause of death of your company? As my co-founders and I were reminded many times during Y Combinator, “Most companies fail because founders give up.” If my emotional state were to be tightly coupled with the rollercoaster of startup life, I feel pretty confident that the intensity could very easily become too much. If you then think about what it would look like to optimise for not giving up (and hence, in the eyes of YC, startup success), the importance of being able to remain at peace and free from a state of perpetual anxiety becomes very apparent. It’s always helpful to remind myself of this lesson during hard times.
Case in point: I wanted to share one moment from the Y Combinator programme this year that speaks to what I’ve written above. I remember going for an evening run along a beach in Marina Bay, San Francisco, after a day full of consecutive VC rejections. Through a combination of the ideas laid out above, I experienced a strong shift from a state of frustration and defeat, to one of real liberation. The feeling that arose was a deep sense of caring so much about my company, and at the same time a profound trust that everything was happening exactly as it should be. The feeling of moving from below to above the line was very apparent, suddenly allowing me to see the day’s events as a tremendous opportunity for growth. That day of relentless VC rejection was one of my happiest moments from the 3 month Y Combinator programme.
A note on meditation: Finally, it would be strange to talk of releasing attachments without acknowledging that the practice of letting go is essentially what underpins entire schools of spirituality, meditation and mindfulness. Meditation has played a significant role on this journey, which I will speak to in-depth in a later post.
Stillness & Scale 