Surfing the Future: Leadership Riding the Waves
Photo by Brandon Compagne on Unsplash
In my last newsletter, I used a surfing analogy to describe how businesses need to prepare for the future. The response was positive, and several readers asked how I guide clients through the process. My approach involves three interconnected conversations. Each one informs and strengthens the other.
What is your purpose? Why do you do what you do?
How would you assess your current state? Are you working towards your purpose? What can be done to improve?
What do you see for the future? In three to five years, how do you need to meet the future?
The How of Your Why
Your mission, the reason your organization exists, should remain steady over time. The ‘how’, your methods, models, and delivery must evolve. The world is constantly changing, and you have to step up to the challenge.
Hospitals exist to treat patients. Movie studios exist to entertain. While each enterprise defines its mission in its own way, the core tenets are the same.
Assessing Current State
You are on a wave of your choosing. Was it the wave you expected? s it carrying you toward your goals, or has it lost momentum? If the ride still feels strong and purposeful, stay on it. If not, it is time to paddle out and catch a new one.
Looking to the Future
All waves will end. As waves near the shore, they break apart and collapse. Deciding when to shift to a new wave can feel daunting. Two strategies can help you determine the right time to make that change: identifying paradoxes and conducting structured debates. Both require you to consider long, medium, and short-term trends.
Ask yourself:
What will your industry look like in three to five years?
What will your customers demand?
How will your products and services need to evolve?
How will your competitors adapt?
How long will your wave last?
Look For Paradoxes
A paradox occurs when two seemingly conflicting things both appear to be true. As business changes, things that seemed obvious become less clear. These sometimes subtle changes serve as early indicators that it's time to pivot. When you spot a paradox, don’t ignore it. This is when it is time to replan.
It is important to revisit the underlying thesis of your business plan regularly. When you see a paradox, it is time to replan.
Embrace Structured Debate
Formal debates are an effective tool for navigating uncertainty. They force a complete explanation of both sides of a question. In his book Good Arguments: How Debate Teaches Us to Listen and Be Heard, Bo Seo explores how debate sharpens thinking and can lead to consensus.
In a debate, you assemble two teams. After a hypothesis is formed, each team must argue for or against it. Participants must argue for their assigned position, regardless of their personal views. In fact, it's often beneficial to assign people to argue positions they disagree with.
Debate forces teams to articulate all of their assumptions clearly and vigorously challenge the other team. The result is sharper insights and a deeper understanding. Structured debate helps leadership to crystallize decisions and move forward with consensus.
The waves rise and fall, a journey never ending. Surf on, never stop.
Related Articles
The Evolution of Wealth Creation | Michael Megarit
Pre-industrial Age Seeded Industrial Revolutions | The Waves
Industrial Revolution and the Standard of Living | Econlib
The Great Stagnation | Widipedia
These 17 Paradoxes Will Change How You See the Universe | Up and Atom - YouTube
Chips and Salsa: Snack-sized news and posts
Never quit in anger. Let the anger subside. Then make a plan to move on. Make the move on your terms and make it strategic.
Revenge quitting: is it ever a good idea to leave your job in anger? | The Conversation
The quality of AI output is directly tied to the quality of its input. Building an LLM based on accurate, accredited, and unbiased data is incredibly hard. Maintaining it is harder. As AI updates its models, the risk of bad data creeping it is high.
AI Models Get Brain Rot, Too | Wired
Working together is the only way to play the long game. Congress is a house divided, and this will slow our progress.
Behind the Curtain: The ever-growing AI inequality gap | Axios
Learning about science is great. I need to think about how this concept applies to business models.
A radical reimagining of physics puts information at its centre | Aeon and Quanta Magazine
I have added two books to my ridiculously long reading list.
Trust Fall: How Workplace Relationships Fail Us by Sarah Mosseri; tt appears to touch on a major leadership failing: too many leaders use the words ‘trust’ and ‘loyalty’ when they really mean ‘blind obedience’. It will be released in the next few weeks.
The Compass Within: A Little Story About the Values That Guide Us by Robert Glazer. This book talks about harmonizing our behaviors across all of the personas we occupy, spouse, parent, employee, manager, consumer, neighbor. Defining our inner moral compass leads to this harmony.
AI can be of great value. To get the most out of it, we need to avoid confusing speed with effectiveness.
Want AI to make you more productive? Here’s the right way to use it | Fast Company
Discipline and flexibility go together, even though it sounds like they shouldn’t. Here are some books about habits and why they are important: Indistractable, Atomic Habits, and The Power of Habit.
How Smart People Maintain Discipline Without Rigidity | Psychology Today
In today’s world, it is hard to be a moderate. I am a moderate. I seek balance. Extreme positions leave little room for flexibility.
The perils of economic centrism in a polarised world | The Guardian
In defense of working 9 to 5.
Living 9-to-5 | The Daily Texan
Measuring what is easily measured is very different from measuring what matters.
An ‘always-on’ workplace always backfires — here’s what businesses should do instead | The Hill
We lived in Detroit for 13 years. It was never part of our plan, but it was a great experience. We say the early stages of Detroit’s rebirth. I hope to go back and see how it has continued to evolve.
An exceptional new park remakes Detroit’s riverfront | Fast Company
Quotes
“It's time to start living the life you've imagined.”
- Henry James
“The camera never lies… but you can take a thousand different pictures of the same scene.”
- Hector Macdonald
“Problems can become opportunities when the right people come together.”
- Robert Redford
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I write about leadership in business and life. I am a certified M&A Specialist and Leadership coach. My perspectives are based on my 40+ year career working with leaders from around the world at over 100 companies.
My goal is to make this newsletter as interesting and valuable as possible. Please share your thoughts and suggestions for improvement. If there are specific topics in leadership you would like me to focus on in future issues, please send them my way.
You can order The Leader With A Thousand Faces on my website's Recommended Reading Page. This page also has links to purchase the books discussed in this and previous newsletters.

