Upstartist Diaries

Don’t Lose Two in a Row

From age 9 to 22, I played competitive tennis, practicing every day for 2-3 hours. Tennis was my life and identity.

Last Sunday, I stayed up until 3am to watch the Rafael Nadal vs. Novak Djokovic French Open semifinal. Both men were chasing history, to win the most Grand Slams ever. Djokovic had 18 titles, and Nadal 20 had titles, tied for most ever with Roger Federer.

This match would play a huge role in determining their legacy. Tennis nerds use things like number of Grand Slam titles, head-to-head record, and winning percentage to answer the Greatest of All Time debate. By winning this year’s French Open, Nadal would surpass Federer and hold the most Grand Slams as a male player. And if Djokovic won, he would close the gap and be the only one among the three to win 2 of each Grand Slam. Djokovic already owned a winning record against both rivals.

I say all this to give you a sense of the massive stakes at hand.

After splitting the first two sets, the two battled for 93 minutes in what became the decisive third set. The level of play was at an all-time high, the tension unbearable. 

What I found most jaw-dropping was each player’s emotional resilience. After devastating breaks of serve, each player raised his level of play and broke back the next game. And after unlucky net cords or bounces that lost them a point, each player would play even better the next point.

I was so impressed by each player’s mental toughness that I photographed my TV screen, when the score was perfectly tied. I wanted to lock in the lesson of these two champions: don’t lose two in a row.

Novak Djokovic and Rafael Nadal battling to a stand still during their French Open semifinal in 2021

Djokovic won, calling it a “top 3 match I’ve played in my career” and later captured his 19th Grand Slam. I wouldn’t be surprised if Nadal wins their next big match.

Last year, my hometown basketball team, the Los Angeles Lakers, won the NBA championship. The team’s mindset the entire year? Never lose two in a row. After a discouraging loss mid-season, Lakers star Anthony Davis said, “We don’t want to lose two in a row. Ever. So there’s definitely gonna be a bounce back game. We want to make sure that we correct everything that we did poorly tonight.” Role player Alex Caruso agreed, “That’s just something as a good team you don’t want to do. You don’t want to let stuff carry over from one game to the next.”

One essential practice in The Fail-Safe Solopreneur is to score each day from -2 (horrible day) to 2 (fantastic day), and jot down why you scored your day high, low or neutral. Over time, you start to understand the core ingredients of your perfect work-day. 

Losing is normal. Having an off-day is normal. Feeling like shit is normal. Not even the greatest in history win every game. But the greatest learn when they lose. They don’t carry their failure to the next game. They bounce back stronger.  

Don’t lose two days in a row. If you scored your day a “-2” or “-1” ask yourself why. What can you differently tomorrow to get back to a “0” or “1” or “2”?

For me, this often means spending more time on activities and relationships that compound long-term. Playing Catan online against AI robots (it happens too often) feels fun in the moment but always leads me to score my day less. I’ll never get back those hours wasted on an activity that has no positive effect on myself, others or the real world.

Is this realistic though? After all, Djokovic, Nadal and the Lakers still lose two games in a row. I still slip and play Catan for hours like a zombie. It happens. That’s life.

But the mindset should never change. Learn from the loss, let it go, and then compete again with confidence. I’m convinced this is a practice of top performers and artists of life. Damming negative momentum and generating positive momentum at all costs. Not losing two in a row. Ever.

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