4 retirement planning lessons I learned from ‘Everesting’

When I reached the summit of Mount Kilimanjaro in 2018, it felt like reaching the peak of a long-held goal. It turned out to be just the beginning. Since then, I have taken on five demanding climbs, including two “Everesting” treks. 

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Though not as well known as other endurance challenges, Everesting involves scaling the same chosen peak repeatedly until reaching a cumulative 29,029 feet — the elevation of the highest peak on earth, Mount Everest. Between Everesting expeditions, I set one ambitious summiting goal for myself each year, challenging myself on new terrains and in new settings. Last year, it was Snow King Mountain in Jackson, Wyoming. 

Looking back on my experiences, it’s clear to me that the lessons I’ve learned from my summits and Everesting climbs apply to advisors helping clients in or approaching retirement navigate today’s market volatility and evolving tax environment amid the largest wealth transfer in U.S. history. 

Everesting, in particular, offers advisors a powerful framework for guiding clients up their own retirement mountains. 

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Visualize the retirement climb

The Everesting journey begins long before you hit the mountain. Before Snow King I kept a photo of the mountain on my wall, visualized the effort and shared the goal with others. That clarity helped me push through physical and mental exhaustion as I ascended the peak. 

Imbuing clients with that same clarity becomes critical for navigating America’s “Peak 65” era, as millions of individuals turn 65 and retire each year. Many have broad aspirations for retirement, but without a defined vision, goals stay vague and risky. Financial professionals can help clients see their Everest. Visualization keeps clients engaged, supports decisions, builds ownership and turns abstract hopes into a plan that can endure the climb.

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Plan small, consistent steps

Everesting isn’t one massive climb. It’s a series of smaller summits, taken one at a time. Financial planning works the same way. Breaking a client’s plan down into manageable steps helps them progress with confidence.

Whether it’s establishing basic protection for their family, creating retirement income streams or ensuring they have funds to enjoy their pastimes in their post-work life, each step builds momentum and progress. 

For financial professionals, this means shifting the conversation from the whole plan to the next milestone while staying aligned to the long-term vision. In a changing environment, clients must trust the process as much as the plan. Consistency, preparation, transparency and empathy create the steady rhythm that builds confidence when decisions feel complex or high stakes.

Act as a client’s ‘community’

The support of friends, family and fellow climbers made the difference before and during my climbs. Financial professionals can be the community that keeps clients moving forward even when the path gets steep. 

With so many concerns weighing on clients, feeling alone can lead to hesitation that can compromise financial goals. The remedy is establishing regular communication rhythms in addition to annual reviews:

Connect clients with tools, specialists and resources that support life beyond finances.Encourage family meetings to discuss intentions, not just assets.Educate clients on insurance products and how they can help address some of their biggest concerns.

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Develop client trust consistently, over time

Build trust with clients the same way you develop physical strength — consistently and over time. More than 100,000 financial advisors — representing 42% of industry assets under management — will retire by 2034, according to McKinsey. 

That means clients will be seeking new long-term partners. Advisors who have built credibility and consistently — one conversation, one meeting, one thoughtful recommendation at a time — and who deliver value will be best positioned to earn the business of those clients. 

Even when a summit is reached, the journey continues. This summer I will embark on the 14,115-foot ascent of Colorado’s Pikes Peak. In financial planning, progress reveals new challenges and new goals. This is where financial professionals thrive, guiding clients with clarity and resilience as they move toward the next summit and the one beyond it.