Like most of us, I’ve felt fear and anxiety when approaching something difficult or unknown, whether speaking in front of crowds or taking on unfamiliar physical challenges. For most of this time, I’ve treated these feelings with a tried and tested tonic: a ‘man up’ and a stiff pat on the back.
Cutting edge stuff, I know.
In late 2025 I started a company for the first time, and I’ve found myself a bit lost. I know that we will succeed. Nevertheless, nagging thoughts sit in my mind:
What more could I be doing? I’m sure I’m messing lots of things up…
In some ways I think these thoughts are healthy, at least as fuel.
When we take risks, we risk feedback, criticism, and maybe even ridicule. And our critics may be completely correct.
This is especially hard medicine for a chronic perfectionist like me to swallow. To combat this tendency, I’ve been drawing on two wells of personal experience:
I grew up a huge tennis fan, particularly of Roger Federer. This was not just because he shook my hand at the 2008 Cincinnati Masters, and arch rival Nadal did not, breaking my then-tiny heart. I fell in love with what David Foster Wallace coined ‘Federer moments’: when he hit a shot so brilliant your “jaw drops and eyes protrude and sounds are made that bring spouses in from other rooms to see if you’re O.K.” (a favorite example).
Against the backdrop of Federer and Nadal, there was a distant third wheel who grew to outshine both: Novak Djokovic. I couldn’t stomach the defeats he handed Federer late in his career. Djokovic was too young, too fast, too strong.
But I’ve realized over the last year that I respect Djokovic more philosophically. He won, he wins because he is mentally stronger. Because he could shake off doubts, fears, and failures better than the rest. He was written off as third string to two otherworldly titans. He was told to quit. He didn’t care. Crowds booed him, pundits dismissed him, and he won anyways. In the words of the 26th US President:
It is not the critic who counts… The credit belongs to the man who is actually in the arena, whose face is marred by dust and sweat and blood; who strives valiantly… who spends himself in a worthy cause; who at the best knows in the end the triumph of high achievement, and who at the worst, if he fails, at least fails while daring greatly
Djokovic teaches us that everything good is on the other side of trying, failing, trying again, and failing better.
I’ve also started to consult Buddhist and Hindu philosophy. In Buddhism, when confronting a negative feeling (fear, anger, etc.), our goal is to accept fear or anxiety as a conditioned, bodily reaction — an anticipatory feeling of a future which may or may not come to pass. I adapted the Buddhist concept of samatha-vipassana to this situation to construct a runbook of sorts:
I found the last bit of advice confusing. Irony normally connotes cynicism, which is not what I’d expect from spiritual teachings. Buddhism, however, has the notion of upāya, which encourages a practitioner to pursue the noble path through means appropriate to their circumstances, even if the reasoning isn’t “perfect”; in other words, something is better than nothing.
When we replace fear with an ironic inner state, we are detaching ourselves from the outcome of our actions, which is a net-positive in the Buddhist lens.2 Attachment disrupts “the sense of embodied freedom” that Zen provides. We can achieve this detachment by acting in one of two ways:
All of this is easier said than done, but these ideas provide some tools for a better 2026. Let me know your thoughts or feedback!