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I only have 50 summers left.
I’m approaching 45 years old. That’s not being dark or cynical. It’s being real. I likely only have 50 summers left. I welcome the reminder. It’s a screaming siren to spend my time well.
It’s particularly top of mind as I recently have had discussions with three separate CEOs (none of whom are members of ETW portfolio companies) who are seriously questioning their professional existence.
CEO 1: Do I want to do this anymore?
CEO 2: Is this worth it?
CEO 3: Why am I working this hard?
Startups are hard blah blah blah. That’s not the point. To me, everything worth pursuing should be hard. Want to get in great physical shape? It’s hard. Want to learn a new skill? It’s hard. Want to build a company from scratch? It’s hard. Want to raise a healthy, happy child? It’s hard (or so I’m told).
I empathize with the three founders. I’ve been in their shoes. It’s lonely. While the highs feel exhilaratingly high, the lows can be debilitatingly low. And when those lows occur, it’s natural to question whether you’re on the right path.
If all suffering stems from a gap between what is expected and what is real, then startup founders constantly suffer. Every early plan is based on f̶a̶n̶t̶a̶s̶y̶ nominal evidence, and achievement typically takes longer and at greater expense than ever expected. To launch a new venture is to be wrong often.
But what do you do when you can no longer handle being wrong? What do you do when you hit that dark place? Turning to your employees, loved ones, or investors falls somewhere between unhelpful and counterproductive. As a CEO, you’re meant to be the beacon of light which can feel impossible when your light (temporarily) dims.
So if you find yourself wondering whether your current endeavor is worth the pain and difficulty, I suggest asking yourself the following questions. The answers won’t save your company. But they may permit you to make your next decision — whether to carry on or graciously surrender — with a clearer mind and heart.
So often the founder loses her independence, confusing the startup with her own identity. What you do is not who you are. If the company vanishes tomorrow, who are you? You are still loving, intelligent, elegant, funny, and hard-working. You are still loved, respected, and powerful. I am not the companies for which I’ve worked or the schools I’ve attended. I’m the sum of so much more, and so are you. Remind yourself. Find the distance to be the dispassionate observer of your own life. Meditate, find a coach, see a therapist, and read an amazing book. Do whatever you must so that you remember that you are a human full of wonder and potential.
Have you asked yourself this question? If you have, I’m certain your answer includes more than just your professional pursuits. I recognize you love your startup though you may have conflicted feelings. But what else comes to mind? Force yourself to list that which you care about. Ask yourself why. If you can call forth that which you deeply care about and break free from your startup-induced blinders, perspective can return.
Have you ever stopped to ask why you’re pushing so hard? Sometimes, the answer is simple — you care deeply for the change your company wishes to affect in the world. But for many entrepreneurs, the motivation stems from a less healthy place. They subconsciously believe that startup success will lead to the acceptance and love they don’t feel in their hearts. I’ve met entrepreneurs who launched companies to win their father’s approval and others who believed startup fame would lead to the relationship of their dreams. If this is you, I’m sad to tell you that you’re wrong, and I would encourage you to go do some work (examples: here, here, and here) and then re-read this post in 6 months.
Humans are exceptionally well conditioned to identify the negative. From an evolutionary biology perspective, it makes sense. Focusing on the negative keeps us out of the (metaphorical) jaws of dinosaurs. But if you’re debating a decision as significant as whether to continue to pursue your company, you need balance. List what is going well. Extrapolate from what’s going well the same way and to the same degree you would extrapolate from what’s going poorly. Write it down — remind yourself that the world is not as hopeless as you feel.
When spiraling, we often whisper a little lie to ourselves… “I have no choice.” That sinister fabrication steals our sovereignty. Our words become our thoughts which become our feelings. Mantras are powerful, so switch from a statement to a question. “What are my options?” When approached honestly, there are always alternatives. They may not be attractive, but by simply reminding yourself that choice exists, agency returns, and victimhood ebbs.
Companies succeed. Companies fail. Wars start and end. Children are born, and our elders pass on. Life keeps moving, and our only choice is how we choose to show up. There are times, in the all-encompassing pursuit of something ambitious, when we can lose perspective. Humans are meant to be productive, to achieve and to explore. But that is not all we are, and when our endeavors consume us and we find ourselves at the edge of the dark place, before falling forward, I hope these questions can return a bit of perspective. I know I only have 50 summers left and want to spend as many of them in the light as possible.
Founded in 2015, Enjoy The Work is a San Francisco-based startup advisory firm serving startup founders and CEOs worldwide.
