Perspective: The Rolling Stone Mindset

March 21, 2024 | G. Derek Henderson


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"Rolling stones turn into sand if they don’t find a place to stand” - Passenger

Morning,

This time of year can feel busy, particularly as it relates to tax time……it’s a time when we tend to be more mindful of what life costs us, and it always gets us looking more closely at our plans.

This past week, I was fortunate enough to attend an annual RBC DS conference in the Bahamas for the last few days, which is always an insightful and delightful experience, to be around some of our peers and industries leader. We had some excellent speakers around a variety of topics, from intergenerational wealth planning to a speaker from the Cleveland Clinic around longevity and health, which will certainly be a trend we are watching closely, not only from an investment standpoint, but also, as we should, incorporating healthy practices and habits into our daily lives.

Of course, being an investment conference, we also touched on markets with lots of constructive discussion around the continued strength of the global equity markets, despite everyone needing to recalibrate expectations for the timing of interest rate cuts. As the central banks need to forecast, to plan, and understand the ever-changing environment around them, so to do we as investors. For us to preserve and protect wealth, while focusing on growth, it’s vital to have an idea of where we want to go – true wealth planning requires reflection, it takes time and it must, at all times, allow us to be agile.

The conference was excellent, but without fail, our travel experiences never seem to go as smoothly as planned. As like any planning in life, travel plans tend to test one’s ability to adapt, our resilience, our agility, and, of course, our patience.

Like a Rolling Stone

You’d have to be living under a rock to have never heard the reference Rollin Stone or, for that matter, not correlate the words with music. The words refer to the traditional proverb, "A rolling stone gathers no moss" and it’s the title of a song that was identified as one of the first songs of one of my favorite blues artists of all time Muddy Waters.….which, in turn, influenced a band from Dartford, Kent, to change their name from The Blues Boys to the Rolling Stones that we all know today.

A Rolling Stone gathers no moss is a proverb that has two opposite meanings, depending on the context.

One meaning is that a person who is always travelling and changing jobs cannot gain knowledge or wealth. The concept of a rolling stone can be romantic in the Jack Kerouac sense, rolling with the wind as it blows and taking life as it comes which has a certain condonation of someone that is perhaps leads a life without structure.

Another way to look at the phrase is that a person who is always moving, will never become stagnant and will always remain adaptive, creative, and able to continually grow. I’m going to propose that there is certainly something not only intriguing about the freedom the rolling stone way provides us, but perhaps it’s a mindset that can lead us towards a prosperous future and a purposeful life if its complemented by a specific fluid planning mindset.

“The wise will make more opportunities than they find” - Francis Bacon

The Rolling Stone Mindset

For a moment, step back and reflect on your life – our lives naturally become more complex over time, with a constant tug of war on our precious resources, our time, and our energy. This complexity also adds a specific tension around our finances, with ever evolving pressures around us. This burden, this weight of responsibility is heavy and makes it difficult, perhaps even impossible, to feel the freedom and breezey alure of rolling through life with flow.

Through our one precious life, the only real constant is change. What if we adapt a mindset that allow us to incorporate the benefit of being a rolling stone, but one with a plan or a path that allowed us to continuously change, while maintaining our momentum and direction. There are specific benefits of not restricting ourselves to a specific regimented framework. The Rolling Stone Mindset provides us perspective that enables us to focus on elements of life that are within our control and affords us the ability to flexible, nimble, opportunistic in our journey.

Historically, most of us have thought of financial planning as a thoughtful, in-depth process, a practice of careful deliberation. For years, we’ve focused our efforts on planning that is a practice that involves evaluating and using as much information as possible, to create a long-term plan. In our view at Henderson Family Wealth, our lives are much too complex, and the world around us is too dynamic, to only focus on the long term. In today’s complex world, the value of traditional forms of planning need to evolve and our plans need to be more reflective and fluid.

In a world where our strategy is becoming more fluid, it’s becoming imperative that we constantly revisit and reinvent our vision, incorporating the agile Rolling Stone Mindset. When you incorporate both vision and agility into your strategy, you not only get a powerful north star to direct your decisions with vision, but also the strength you need to make quick changes with improvisation too. The question is, how can you redesign your plan according to agile principles?

Here are a few simple steps that could help:

Begin by polishing a compelling and clear vision of what you think success means to you, reflect on what you really want to set out to accomplish. If you have a solid vision then you’ll be able to adjust your strategies and plans to approach the same outcome from a different angle when problems in your strategy begin to emerge, or it can uncover opportunities along the way.

  • Vision: Decades
  • Strategy: Yearly
  • Tactics: Quarterly
  • Effort: Daily

“To achieve great things, two things are needed; a plan, and not quite enough time.” - Leonard Bernstein

Sisyphus and the Stone

Greek legend of Sisyphus, who was condemned by the gods for eternity to repeatedly roll a boulder up a hill only to have it roll down again once he got it to the top….as a metaphor for the individual’s persistent struggle against the essential irrationality of life and as punishment for trying to stop death

The moral of "The Myth of Sisyphus" is that there is no greater meaning in life but what we give it. When we accept that there is much in life that we can not control, we can free ourselves from many external pressures that we may face, or adapt to the unexpected nature of life. French Philosopher Albert Camus’ perspective on the story is that life can feel like an uphill battle because we continue to try to impose order on existence and to look for answers to unanswerable questions.

However, in my view, if we can develop a mindset of understanding, of gratitude, and of joyful acceptance of change, we can turn the of the uphill struggle into a fluid rolling path.

Henderson’s Rolling Stone Mindset Rules

  • Courage over confidence
  • Simplification over complexity
  • Progress over Perfection
  • Presence over Power
  • Courage over Confidence
  • Creation over Consumption
  • Purpose over Pleasure
  • Discipline over Comfort
  • Inspiration over Ego

“As you start to walk on the way, the way appears." - Rumi

Yutori

There are several benefits that creating an agile wealth plan may provide us, including peace of mind and confidence as you work towards your vision goals increased control and protection.

As the Japanese concept of Yutori reminds us, give yourself the space to have peace of mind and, while you’re rolling like a stone, be sure to take the time to fully be present and immersed in your moments.

I recently heard the Passenger lyric I reference in the outset of this musing, it was in a song at my daughter’s Dilynn and Presley-Mae’s dance competition over the weekend. I found the lyrics inspiring, a message that there are perhaps benefits of being a rolling stone. If you can understand your vision while adopting this mindset, you can not only avoid tuning into sand, but you can create a beautiful all-encompassing life, a journey on which you can stand. Keep rolling on your journey, revisit, recalibrate, reflect on your vision and roll along my friend.

“Give me the place to stand, and I shall move the world” - Archimedes

Be well and enjoy the moments,

G. Derek Henderson

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