Self-mastery Nº104
Be in the arena
Recently losing my cat to illness taught me a lot about strength. I won’t go further into it as the emotions still sting. But seeing something close to me battle through so much pain, and try to carry on despite the stumbles, brought a lot of love out of me—and now, she has inspired a quality I wish to create.
The credit always belongs to the one in the arena, “who’s face is marred by dust and sweat; who strives valiantly; who errs, who comes short again and again, because there is no effort without error and shortcoming,” as said by Theodore Roosevelt. I feel blessed and sometimes a bit cursed to have faced such a mixed bag of “challenges” early in my life. Good and horrid relationships. Money troubles. Family conflict. Abuse. Bullying. I’m very far from the worst off in this world. But I feel now that I have some understanding of hardship that is at least a little bit special.
The world is designed to depress us as happiness isn’t very good for the economy. If we were happy with what we had, would we need more? This view from Matt Haig’s Reasons to Stay Alive moves me because the world thrives off of worry. We live in a world that preys on people who are less intentional and more impulsive, as well as those who fear failure more than the rest. People who’d rather sit and observe from a distance, in comfort, than be in the arena, building their point of view and working from there.
Observing the play and best practices from the outside can be useful. But this superficial understanding will never match the rate of improvement you gain from being in the arena where, in today’s world, failure often comes with minimal cost. But the arena is our greatest source of growth and learning.
Many people spend their lives over-analysing or finding potential flaws or merit in their arguments or ideas solely based on what others tell them. The same people that have never been in the arena themselves. But you need to be in the arena to see things for what they really are: where you observe the most profound challenges, understand the merit or potential of things, and accept what you don’t know yet. It exposes and exacerbates the flaws of ideas—but helps you spot the opportunities in the gaps no one else sees.
Becoming a parent for the first time is one example. No matter how much guidance you read, practice runs with baby toys, or products you buy in preparation, you’ll never be 100% prepared for the ups and downs of raising a child. It’s not something you can convey without the actual experience.
Let’s take another step and consider a tech company that brought something new and revolutionary to the world: eBay. It was founded in 1995 by Pierre Omidyar, a visionary trailing through the early internet with a vision to create the perfect open marketplace built on trust and the feeling of honest human interaction.
At the time, you had to be in the arena to truly understand what was so special about eBay. The community-first approach laid as bedrock and ensured it was trust-oriented, that voices were always heard, and that it could rival opposing businesses by making bets no one else thought were valuable.
It was a powerful demonstration of how sceptics or analysts—with a superficial understanding and without “being in the arena”—missed the generational opportunity with early eBay. You can never truly predict the future, but the arena is the best way to harness foresight. And this is why entrepreneurs rarely care what “analysts” have to say about their business.
This year I’ve committed to being in the arena more than I can think possible. I value advice and foresight from the people I trust, but I no longer want to make big judgement calls or changes in direction in my career or life without putting myself in the space to learn and build my point of view first.
Doing so offers tremendous insight and conviction in my beliefs and mental models—which I learn to build and trust in—that will help form my path going forward.
So here are four steps to being in the arena:
Never judge something too early, or listen to the opinions of people who are not (or never have been) in the arena. It’s easy to be a sceptic, contrarian, or someone who talks about something without having skin in the game. I learned the importance of avoiding the advice of people who give advice for a living; giving advice is easy by nature, but most of it tends to be suitable for the advisor and harm you without warning. Beware that they rarely ask themselves if they understand something enough or have been willing to develop a deep understanding.
Focus on building as much foundational knowledge as you can in order to have an informed point of view. If you want to learn something more deeply: develop as much knowledge as possible without taking any sort of “leap” in between. Give yourself a set of questions before you start a business or whatever it is you want to do. You’re at the superficial knowledge stage here, but at least you’re taking steps in the right direction.
Test and experiment with small and cheap endeavours that can get you in the arena without making big life decisions too early. Once you have enough foundational knowledge to be on the more informed side of superficial knowledge, try experimenting with small actions that get you in the arena. In this phase, you are actually in the arena—which is the hardest step for most people because they don’t know how to approach it. The solution: be permissionless. Don’t wait for opportunities to knock at your door. You don’t deserve that. Instead, ask how you can sneak your way into the back doors. Ask yourself how to leverage your skills to contribute to a field of work or community you’re interested in and gain insight.
When you’ve assessed the opportunity enough, get fully in the arena. At this point, you’ve crossed the chasm from a superficial to a deeper understanding. Based on your intentional experimentation before this point, you can decide whether to forge ahead and fight in the arena or back out—which you never have to feel bad about.
All of this will help you reach places you didn’t think you could—whether you lacked the confidence or preparation to get there. I learned a lot of this from something small but special to me. And now, it’s a quality I will work hard to build to keep what I lost—but also gained in memory.