Winning is hard, really hard. Most people only win a handful of times each year, whether those are wins at work, in the classroom, at the theater, or on the court.
I’m reminded of a quote from Roger Federer’s Dartmouth commencement speech:
“In tennis, perfection is impossible… In the 1,526 singles matches I played in my career, I won almost 80% of those matches… Now, I have a question for all of you… what percentage of the points do you think I won in those matches?
Only 54%.
In other words, even top-ranked tennis players win barely more than half of the points they play.”
Federer is considered by many to be the greatest tennis player ever, and yet he lost 54 finals on the pro tour and barely won more than half the points he ever played. I’m sure he lost many more matches and finals off the pro tour that no one knows about. Winning is really hard because it takes a lot of losing and failure to learn how to win, and to win the right way.
Steve Jobs is regarded by many as one of the greatest visionaries + entrepreneurs ever, yet he failed early on more times than most remember. The Lisa was a failure, the first Macintosh was largely a failure, the NeXT computer, also a failure. Most people don’t know that the iPhone was technically not the first “Apple phone”; it was a Motorola phone (the iTunes phone) in 2005, and it was pretty bad.
But all of these failures, and the learnings that came with them, made Jobs into who everyone remembers him as: the “inventor of the iPhone” and one of the greatest visionaries of all time.
A few lessons I’ve learned over the years on what it takes to win.
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Consistency always compounds. In whatever aspect of life you are aiming to win at, you have to show up day in and day out, stick with it no matter how hard it gets, and eventually winning will happen.
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Failure is okay. Funnily enough I won the first ever competitive tennis match I played. But then I lost many, many matches before I learned how to win and truly understand the game. It’s okay to fail, there is no such thing as winning everything and never losing. Once you accept that, you will slowly start to learn how to win (and master) the game (whatever that game may be).
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“Be the first one to show up, and the last to leave.” My tennis coach growing up would always repeat this to me. If you want to be the best at anything in the world, it won’t happen by only doing 95% of the work, or being the second hardest working person in the room. To achieve anything great in life, I believe this is so important, be the first one to show up, and the last to leave.
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“There is no way around the hard work. Embrace it.” My favorite quote from Roger Federer. I ran my first marathon last year, I was not much of a runner before this, and in fact I had run less than 180 miles combined in 2022 and 2023. When I decided to sign up for the NYC Marathon at the end of 2024 (for 2025) I knew there would be no way around the hard work. I embraced it. I followed my training plan to a T and when I missed workouts or fell sick, I still got the mileage in. At one point last year, I ran more in one week than I had in the entire year of 2023. I ran over 1800 miles in my lead-up to the marathon and embraced the hard work, no matter how tough it got.
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It’s okay to learn from others and ask for help. The greatest entrepreneurs, musicians, and athletes in history did not do it all on their own. They did not magically turn up and create the most important technologies, musical pieces, or win the most important championships in history by never learning from others. Ultimately, your drive to build, learn, or accomplish anything has to come from within. Yet, that does not have to stop you from asking others for help.