Are You Playing to Win?

My college-aged son invited me to San Antonio for the Willie Nelson concert with his roommates and their dads. On the trip, he revealed some surprising news.

“The best way to predict the future is to invent it” ―?Alan Kay (American computing pioneer and inventor)

This Week's Edition

Does your approach to new things tend toward “playing not to lose?” Or do you lean toward “playing to win?”

Clarify Your Thinking

“Dad, I’ve started a business with my roommate, James,” he said. My first reaction was excitement. He wasn’t wasting his free time playing video games or any other senior-in-college-type activity. He was starting a business! I was the proud papa of a budding entrepreneur.?

The other dads on the trip began an impromptu strategy session fueled by a barrage of questions:

Q: What’s the business?

A: A junk hauling business.

Q: How will you do that?

A: We already bought a trailer.

Q: How much did it cost?

A: $5500 – discounted from $7000.

Q: How will you market the business?

A: We aren’t sure yet.

Q: How much will you charge?

A: We aren’t sure yet.

Q: How much time will this take?

A: We aren’t sure yet.

The two business owners withstood the firing squad by answering most of the questions. The questions they couldn’t answer did not deter them in the slightest. They just shrugged their shoulders and said they would figure it out.?

In the same conversation, I witnessed two different approaches to the new business:?

1. Entrepreneurial zest that was unfazed by what they did not know.

→ Their mindset was, play to win!

2. Somewhat skeptical counsel offering critical questions for every aspect of the venture.

3. Their mindset could have been interpreted as, play not to lose!

Old Thinking: Note: there was no old thinking in the minds of the new entrepreneurs. They had no previous “thinking” grid that was holding them back.?

New Thinking: We are in the game. We have the trailer. We are motivated. We will figure it out. In the worst-case scenario, we can sell the trailer and get our money back. At the end of the day, we will have learned a lot.?

The fresh, unadulterated initiative of the two entrepreneurs was a sight to behold. Nothing was holding them back. Their curiosity and fearlessness produced early results:

→ An understanding of insurance needs for commercial hauling?

→ The price per ton for the local landfill deposit

→ A clear desire for recurring revenue

→ Meeting a developer who wanted to sell them three more trailers

→ Finding two sophomores who would be laborers today and potential buy-out owners when my son and his business partner graduate

→ Additional revenue streams beyond hauling junk: inventory/supply delivery to construction sites, firewood delivery, etc…

Here are the takeaways I’ve come up with so far for us leaders:

1. Sometimes, we need to stop talking about (and analyzing) the idea and buy the “trailer.” Investing money commits you to the cause.
2. Once we’ve committed to the idea, striking out and talking to a vast number of other people (without hesitation) exponentially expands the idea.
3. When we get in the game, additional revenue streams (and benefits) materialize because we find opportunities not readily seen when we’re standing at the starting line of the idea.?

Most of us have seen what can go wrong. This makes us “wise” as we can see things a younger version of ourselves could not see. Conversely, young bucks like my son and his roommate can more easily see things our risk-averse eyes can’t – a love of learning new things and the potential of ideas that may sound ridiculous to others. ?

Both points of view are valuable. Do you have someone on your team who favors the approach of my son? If not, you might want to find someone who does and give them a seat at the table.?

Boost Your Performance

Watch this week’s video for more of the story about how fresh eyes can help you play to win vs. play not to lose.?

What’s Your Opinion?

What lesson did you learn from this week’s newsletter? Let me know: [email protected]

If you are going to be a leader, you might as well be a good one. Don’t let doubt count you out. Have a confident week!

Robin Pou, Chief Advisor and Strategist

We live to make bad leadership extinct so forward this newsletter to others who strive to be confident leaders.?

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What is “The Confident Leader”?

During the Covid-19 Pandemic, I began a video series called “Panic or Plan?” It was designed to equip leaders to navigate the doubt they experienced and to rise in the confidence they needed to lead during turbulent times. It took off. I then started this newsletter to equip leaders in the same fashion each week for the doubt that crashes across the bow of their leaderSHIP.