The Hill You Will Gladly Die On
“Life is not a problem to be solved, but a reality to be experienced.” — Søren Kierkegaard
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Sooner or later, most founders encounter a life situation that feels so challenging, so painful, and so humbling that it brings them to a moment of surrender. As difficult as these moments can be, overwhelming struggle is a normal part of your hero’s journey. With the benefit of age and experience, I’ve come to see more clearly that the way I embrace my lows is what ultimately defines my fate. So I embrace those lows by welcoming the difficult emotions too. Pain can be the ideal teacher, if you let it be. Surrendering is not the same as giving up.
Expectations and Struggle
Although painful mistakes in entrepreneurship are guaranteed, I believe that founders can save themselves some emotional struggle by understanding how the expectations they create influence their emotions.
Given that you’ve become good at solving problems for a living, you might be tempted to approach everything as a problem to be solved. I love solving problems, sometimes even when there are no problems to begin with. With only a hammer, everything starts looking like a nail. But life is ultimately more than hammering nails. Life is a voyage, not a puzzle.
As crazy as it might sound, you don’t have to fix anything. If you’re seeing problems to solve everywhere, you might want to reevaluate how you form your expectations. Maybe that’s where a lot of these troubles are coming from.
Expectations are beliefs and assumptions you hold about the future. On one hand, holding high expectations can be a self-fulfilling prophecy. Expecting excellent work might help your team rise to your high standards and achieve something they didn’t know they had in them. On the other hand, low expectations can save you from the brutal sting of failure and disappointment.
When should you have high or low expectations? High vs. low expectations is another duality paradox. From my own experience, expectations should adjust based on the time horizon—the larger the time horizon, the larger the expectation. Finally, expect to be disappointed a portion of the time. That includes your expectations of yourself. Your expectations should leave a margin of error—we’re all flawed, complex, and unpredictable humans.
Positive Expectations or False Hope?
James Stockdale was held captive for over seven years during the Vietnam War. He observed that the most optimistic prisoners often fared the worst, because they were crushed when their expectations were not met, having falsely expected, for example, that they would be released by Christmas Day.
Stockdale maintained his will to survive by accepting the powerlessness of his reality while retaining faith that he would eventually prevail. This mindset, termed the “Stockdale Paradox,” involves balancing unwavering faith in eventual success with the discipline to face a brutal reality.
This paradoxical mindset holds high and low expectations simultaneously: high expectations in the long term, low expectations in the short term. It’s an attitude I’ve observed among outstanding founders too. They believe their success is inevitable, while expecting, even relishing, failures and adversity along the way. Managing your expectations effectively saves you emotional turmoil.
The Fruit and the Labor
Steve Jobs was famous for repeating the old adage “The journey is the reward.” To me, the biggest factor in Jobs being one of history’s most impactful founders was his ability to hold both extremely high and low expectations simultaneously.
He chose his journey for the journey itself, with no expectation of outside success, motivated intrinsically to “make insanely great products,” wherever that might take him, all while letting go of any expectations of specific results. Jobs held very high expectations in terms of the quality of design, but he focused on the act of creation itself.
Today Jobs is remembered for his successful products, but we forget he shipped a bunch of failed product ideas: the Apple Lisa, NeXT Computer, Newton handheld, Macintosh TV, and iTunes Ping to name a few.
“The journey is the reward” is a timeless and universal mantra. The Bhagavad Gita, an ancient Hindu scripture written around 200–400 BCE, explores a crucial paradox that founders encounter to this day: how to pour yourself into your creative calling while detaching from expectations of results.
“You have a right to perform your prescribed duties, but you are not entitled to the fruits of your actions. Never consider yourself to be the cause of the results of your activities.”
— Bhagavad Gita, chapter 2, verse 47
Embracing this philosophy made Jobs bolder and more tolerant of failure. When he returned for his second stint at Apple in 1997, he was looking at failure dead in the eyes. The company was weeks away from bankruptcy. Without pressure to conform to high market expectations, Jobs could see clearly what Apple needed and went on to lead one of the most epic turnarounds ever.
Unimpeded by fear, he felt more apt to make the concentrated, contrarian bets that gave us the iPod, iPhone, and iPad.
A Fearless Mind
A fearless mind free from expecting results is a powerful combination: this is the mindset of someone with nothing to lose. Think about this: What would you keep doing even if failure was assured?
If you are doing something hard and new, try starting with the assumption that failure is the likely scenario. Because it is. Assuming failure in this case is not pessimism; it gives you freedom to do your best work.
If you can find true inner motivation to pursue your path regardless of success or failure, then nothing can stand in your way. Choosing your “hill to die on” ultimately helps you clarify your deepest intentions.
Defining and owning your symbolic hill creates a healthy distance between you and your expectations for the future. Find something you want to create so badly, something that needs to exist so much, that it makes all your sacrifices worthwhile in the end.
Fruit Without Attachment
Paradoxically, when you don’t expect results and don’t buy into fear of failure, your labor might yield more “fruit” than you could ever get otherwise.
What should you do when all these bounties come your way? Help others and further your sense of purpose. These fruits were not for you to expect nor hoard. Sharing the abundance in your life will only multiply your wealth.
The Buddha taught that generosity brings happiness at every stage of its expression. We experience joy in forming the intention to be generous. We experience joy in the actual act of giving something. We also experience joy in remembering the fact that we have given.
“You have not lived today until you have done something for someone who can never repay you.”
— John Bunyan