The Generational Cost of Regret

How conquering difficult moments in life will define us

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 If you think the price of winning is too high, wait until you get the bill for regret; it’s generational.

 

Context

Two nights ago, I awoke at 3 am to nurse an unwell crying child. Awake, I scrolled through my phone and stumbled upon a podcast with Tim Grover, the world-renowned personal coach to CEOs and star athletes, including Michael Jordan and Kobe Bryant.

What he said hit me hard as I was holding my daughter:

“If you think the price of winning is too high, wait until you get the bill for regret – and that bill is generational. A lot of individuals are passing that bill on from one generation to the next to the next to the next.

“There’s a moment in everybody’s life as a dark forest and a dark moment. How you handle that dark forest, how you handle that dark moment, determines everything.”

What Tim calls “the dark forest” is a time of profound challenge. It is within the depths of these woods that our mettle is tested, our spirit is forged, and our true potential is unlocked.

The price of winning is steep, but the cost of regret is far greater.

We often encounter moments when we’re made to choose between an easier path and a harder one that we know will pay off.

Having helped iconic athletes such as Michael Jordan and Kobe Bryant develop their skills and realise their full potential, Tim knows very well how individuals who transition from good to great, who become unstoppable in their field, share a common thread: they did not flee from their dark moments.

We find the rawest form of our potential, waiting to be shaped by will and action. The question is not whether we will encounter these dark forests but how we will navigate them.

Will we become prisoners of regret or architects of a future written by the hands of courage and dogged resilience?

Real Life Story

Since 1989, Tim Grover has been on the frontlines of elite athletic training, having mentored legends like Michael Jordan and Kobe Bryant.

Tim’s illustrious career highlights the value of harnessing one’s mental and physical capacities to confront and overcome “dark forest” moments. 

His philosophy – rooted in a relentless drive, result-driven performance, and unwavering mental toughness – illustrates how moments of grit lead to unparalleled excellence in sports and entrepreneurship.

PostScript: Once, he asked the late Kobe Bryant to describe the concept of winning in one word. The NBA legend, known for his gruelling practice routines, replied: “Unapologetic.”

Practical Tools

Let's take a closer look at how to overcome “dark forest” moments:

  • Value Persistence Over Regret: Recognise the long-term cost of regret from not pursuing goals and ambitions, and see persistence as an investment in your legacy for generations.

  • Define High Personal Standards of Success: Set and live consistently by your own high standards of success, ensuring they align with your values and are not solely influenced fleetingly by external expectations. I call these points of celebration, and I often say we need to set the bar high.

  • Focus On Quality of Workload: Rather than be overloaded with the volume of work, be strategically focussed and prioritise the intensity of your efforts to produce quality outcomes.

  • Embrace Tempo with Intensity: It is not humanly possible to play a long game running at 100% full speed all the time but learn how to combine tempo with intensity.

Find Out More

Do you want to learn more about the practical tools noted above? Are you aiming to find the right support for scaling up your business?

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Until next week, may the force be with you.

Kevin

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