Guest: Nikki Henderson, a world-class professional sailor. In 2018, Nikki became the youngest skipper to lead a team in the Clipper Round the World Yacht Race. At the age of 25, over the course of more than 40,000 miles of ocean racing, Nikki led a diverse team of mostly amateur sailors from 16 countries to an extraordinary second place finish. She's also skippered numerous transatlantic races and won the Race to Alaska.

In a Nutshell: How do you define your job as a leader?

Nikki Henderson says that what she does as a skipper is pull together disparate individuals, build them into high-performing amateur teams, and then compete in the most extreme sailing races in the world.

I experienced Nikki's leadership first hand a few weeks ago when I sailed with her in the Caribbean 600 as part of her amateur crew. This was a grueling 600-mile race around 11 Caribbean islands. Despite long odds, we ended up finishing third and celebrated on stage with our prize: a big bottle of rum.

On today's show, Nikki Henderson and I discuss making life transitions, paradoxes and polarities in leadership, and decision-making under pressure and uncertainty.

I discuss how well I executed on my 3 words from 2024 and then reveal why and how I'm changing the exercise for 2025.

For 2025, I'm going to explore polarities—pairs of words that represent the tension and harmony between opposing yet complementary concepts.

This shift feels like a natural evolution.

Just as life is a balance of contrasts—action and rest, growth and reflection, giving and receiving—polarities allow for a more nuanced exploration of the rhythms that shape us.

It's not about choosing one over the other, but about navigating the balance between the two, finding wisdom in their interplay, and allowing them to guide me in a more holistic way. This approach reflects where I am now—a stage of growth that seeks to integrate opposites and embrace the richness of life's cycles.

My 3 Polarities for 2025

• Horizon – Hearth: Pursuing dreams while not losing sight of what's amazing in my current day-to-day life.
• Slack – Flood: Adjusting my pace to optimize my energy.
• Control – Flow: Blending detailed planning with tapping into the universe's current.

There's an old quote from Richard Branson that has stuck with me for many years. He said, "I don't think of work as work and play as play, it's all living."

Similarly, in recent years, My 3 Words, and now My 3 Polarities, make little distinction between the personal and professional. I view them as a guide for living. That way, I don't have to ask myself, "Does this apply to work or to my personal life?' And if I do, the answer is, "Yes."

Here are some practical tips for creating a "My 3 Polarities" exercise:

1. Identify Key Tensions: Reflect on areas of your life where you feel pulled between two opposing but complementary forces (e.g., fear vs. courage, ambition vs. contentment, chart vs. explore, journey vs. destination, reinvention vs. continuity).
2. Choose Meaningful Pairs: Select three polarities that resonate deeply with your values and current life stage. Ensure each pair addresses a distinct aspect of your life, such as goals, energy, or mindset.
3. Define Each Side: Clearly articulate what each side of the polarity represents for you, including the values and behaviors they inspire.
4. Create Guiding Questions: Develop a key question for each polarity to guide your decisions and self-reflection (e.g., "If I wasn't fearful, what decision would I make?").
5. Track Progress: Use a journal or weekly reflection to assess how well you're honoring both sides of each polarity.
6. Integrate Into Daily Life: Regularly remind yourself of the polarities and apply them to real-life choices, whether at work, home, or in personal growth. Print them or have them on your computer screen and see them daily.

Now it's your turn. Take a first pass at your My 3 Polarities exercise for 2025 and then set it aside. Revisit what you wrote the next day and see if they still feel good.

Guest: Dr. Preston Cherry, AFC®, CFT-I™, CFP®, Ph.D., an entrepreneur, coach and speaker. Dr. Cherry is the creator of the Life Money Balance™ approach and founder of Concurrent Financial Planning. His new book is Wealth in the Key of Life: Finding Your Financial Harmony.

In a Nutshell: "Songs in the Key of Life" is one of Stevie Wonder's most famous albums. In a similar vein, Dr. Preston Cherry wants people to find that kind of harmony between their money, their values, and their lives. And advisors who can help folks create a financial life that really sings are going to connect more deeply with clients and empower them to live -- and plan -- with more intention.

On today's show, Dr. Preston Cherry and I discuss his new book and his unique perspective on how to bring purpose, balance, a "permission to prosper" and a little bit of rhythm to your financial planning process.