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As we get older, our social networks tend to get smaller.
Old friends drift away, move to Florida, get absorbed in their own families or, sadly, die. The casual architecture of midlife — school events, office friendships, neighborhood dinners, business travel, pickup basketball, church committees — begins to thin out.
But as much as I sometimes complain about living too much of life online, I have come to appreciate one thing: LinkedIn can be a pretty good retirement tool.
Not for posting humblebrags about “exciting new chapters.” Not for collecting likes from people you barely know. But for keeping a thread of connection alive with people who once mattered, even if they were not close friends at the time.
Recently, LinkedIn helped me reconnect with Dennis Hoffman, someone I had always admired. We worked together almost three decades ago at Avid Technology, the company best known for transforming film and digital editing. I was in corporate communications. Dennis ran a small storage division. We did not work closely together and we were not friends in the traditional sense.
Yet 28 years later, we found each other again.
Thank you, LinkedIn.
A Strategist Enters Retirement
Dennis recently retired from Dell Technologies at age 63. What struck me first was not that he retired, but how deliberately he approached it.
Every January, he told me, senior leaders were asked about their retirement plans. What’s your runway: one year, three years or five years?
That may sound blunt. But there is wisdom in it. For a company, it is succession planning. For the executive, it is a respectful acknowledgment that a long corporate career does not end by accident.
The question gets asked clearly. The answer is treated seriously. There is no ambiguity, no pretending the topic will go away, no awkward silence while both sides wait for the other to bring it up.
Direct and plain-spoken is exactly the right tone for a conversation that consequential.
As a corporate strategist, Dennis began thinking about retirement the way he had thought about business: as a system with multiple moving parts. He had already mastered several artificial-intelligence tools, so he began using AI to help develop his own retirement strategy.
The result became a comprehensive online assessment called The Retirement Strategy, or TRS.
The framework is built around six retirement domains: wealth, health, people, place, passion and purpose. Those categories will sound familiar to many retirement coaches. They certainly did to me. When I became a certified retirement coach, I learned quickly that financial planning and retirement planning are not the same thing.
Money matters, of course. But money alone does not tell a client who they will have lunch with on a Tuesday, where they will feel at home, what will get them out of bed, how they will replace the identity work gave them, or whether they can actually enjoy spending the assets they spent decades accumulating.
That is where the best advisors can make a deeper impact.
AI as a Better Question Engine
Some advisors may look at AI retirement tools and feel threatened.
I think that is the wrong reaction.
The better question is: How can AI help advisors create richer, more human conversations?
Used poorly, AI can become another shiny object, another generic calculator, another automated output that tells clients what they already know. Used well, it can become a better question engine. It can help surface patterns, organize complexity, identify blind spots and give clients language for things they may have felt but never named.
That matters because many successful clients are fluent in the language of wealth but less practiced in the language of transition.
They can talk about asset allocation, concentrated stock, Roth conversions, tax brackets, estate planning and sequence-of-returns risk. But ask them what they are retiring to, who they want to become, how they will rebuild friendship after leaving work, or whether they can spend without guilt, and the conversation often changes.
Sometimes it gets quiet.
That is not a failure of the client. It is a planning opportunity.
What I Learned Taking the Assessment
I was one of the early participants Dennis invited to try the TRS assessment. I scored well across most categories, but not as strongly in People.
That did not surprise me entirely. Like many men in their 60s, I have plenty of professional contacts and friendly acquaintances. But deep friendships require more than a good contact list.
The assessment gave me something useful: a nudge to be more intentional about rekindling old relationships, building new ones and spending time with younger people who share similar interests.
It also reminded me of something I had underestimated.
Playing piano is not just a minor hobby for me. It is a real passion.
I do not need to play piano at a Holiday Inn on a random Thursday night. I do not need to be on stage. I do not need applause. But the creative act of sitting at the piano brings me a kind of joy few other things do.
TRS helped me see that my daily piano practice is not simply recreation. It is engagement, artistic growth and a form of identity.
That may sound small. It is not.
In retirement, small discoveries often carry big meaning.
For advisors, this is the opening. A client may come to you for investment management. But they stay with you because you help them feel seen, heard and better prepared for the life their money is supposed to support.
The Wealth Number Is Not the Whole Story
Advisors will naturally be interested in the Wealth section of any retirement assessment. That is familiar territory. Even if clients think their financial lives are in good order, retirement has a way of exposing doubts.
They may have a sound portfolio, a withdrawal plan and a long-term strategy. Still, the transition from earning to spending can feel strange.
Dennis is not a financial advisor. He is quick to say that. But his approach to wealth is thoughtful because it separates two kinds of readiness.
The first is structural readiness. Do clients have enough assets? Have they stress-tested their withdrawal plan? Have they modeled healthcare costs, inflation and sequence-of-returns risk? Is their income plan resilient enough to survive a difficult first decade of retirement?
These are the questions the financial planning industry has spent decades trying to answer. The tools exist. The software exists. The advisors exist. Many clients who have done the work have reasonably good answers.
The second kind is psychological readiness.
Can clients actually spend the money? Can they stop measuring their worth by their income? Can they handle the anxiety of drawing down a portfolio, even when the plan says they can afford it? Can they give themselves permission to spend on the experiences and people that matter most?
That is where many retirement plans go quiet.
And that is where advisors who understand the human side of retirement can differentiate themselves.
The Industry’s Uncomfortable Blind Spot
Dennis’s own experience with financial advisors has been mixed. He has worked with a number of big-name financial services firms, both through employers and on his own. None of those relationships lasted.
Too often, he felt he was being sold a product or service. The conversation circled back to assets under management, insurance or a recommendation that seemed to serve the firm’s business model as much as his life.
He did not feel that anyone was asking the deeper questions or listening carefully enough to what mattered to him.
That critique may be uncomfortable. But advisors should not dismiss it.
Dennis does not see himself as a victim of poor retirement planning. In some ways, his platform is a kind of financial services anti-hero — not because it rejects advisors, but because it challenges the industry to reset the conversation.
He is not beholden to a product shelf. He does not have to sell annuities. He is not trying to gather assets. He is trying to help people think more clearly about the transition itself.
That should not scare good advisors.
It should energize them.
Because the best advisors already know this truth: a portfolio can be well-built while the life around it is underbuilt.
Tradeoffs: Place Has a Cost
Dennis learned that firsthand when he and his wife moved from Massachusetts to Jackson Hole, Wyo., in 2017.
They chose Place very intentionally. They wanted a certain geography, rhythm and lifestyle for the next stage of life.
It was the right decision on Place. But it came with a cost on People.
The move severed much of the social architecture they had built over decades in the Northeast: the dinner rotation, the casual encounters, the people who were part of the weekly flow without needing to be scheduled.
Deep friendship, Dennis came to believe, is not built mostly through occasional flights and well-meaning texts. It grows from repeated contact, shared spaces and unplanned encounters over time.
That is a hard lesson for many retirees. We assume friendships will resume when we have more time. We assume purpose will appear once work stops crowding it out.
Often, neither happens automatically.
For advisors, this is not outside the planning conversation. It is central to it.
Where a client lives affects spending, taxes, healthcare access, family connection, transportation, social engagement, longevity and quality of life. Place is not just a lifestyle preference. It is a retirement risk factor.
People and Purpose Need Architecture
TRS has been in the market only a few months, but Dennis says more than 350 people have completed the 25-to-40-minute assessment. The biggest surprise, he says, is how often People and Purpose score lower than the more structural categories.
These are people who spent careers building businesses, managing teams and solving complex problems. They know how to execute. But they often have not applied the same discipline to friendship, community or meaning.
Purpose, too, is misunderstood.
Our culture likes to say you “find” your purpose, as if it were hiding under a rock. In reality, purpose is usually built. It comes from sustained contribution, experimentation, reflection and repeated engagement with work or service that feels worth doing.
That is what I like about Dennis’s larger argument. Retirement is not a finish line. It is a transition.
And like any major transition, it deserves architecture. The financial services industry has overlooked this to date.
AI may help with that architecture. It can organize information, surface patterns, ask better questions and help people see gaps they might otherwise avoid.
But it cannot live your client’s retirement for them.
It cannot make their friends, choose their community, practice their instrument, repair their marriage, strengthen their body or give them courage to spend money on the life they say they want.
Those are still human tasks.
The Advisor’s Opportunity
The advisor of the future should not be afraid of AI retirement tools. The advisor of the future should be curious about them.
Not because AI replaces the advisor, but because it can help expand the conversation advisors are already trying to have.
Imagine using AI-supported assessments before a retirement planning meeting to identify where clients feel strongest and where they feel exposed. Imagine seeing that a client’s financial readiness is high but their People score is low. Imagine learning that a client who looks fully prepared on paper is anxious about spending, lonely after leaving work or unsure where they belong.
That kind of insight can change the tone of a meeting.
It can also deepen the relationship.
Clients do not always need more charts. Sometimes they need better questions. Sometimes they need permission. Sometimes they need an advisor who is willing to say, “Your money looks solid. Now let’s talk about the life this money is meant to support.”
Dennis told me he does not see TRS as just another retirement product. He sees it as the start of a broader argument: that the six domains of retirement are really a framework for any major life transition. They apply to executives leaving corporate life, athletes leaving professional sports, military officers leaving service, founders exiting companies and parents stepping away from paid work to become caregivers.
That seems right to me.
Retirement is a 19th-century word for what has become a 21st-century project — one that may last 25 or 30 years.
The better question for clients is not simply whether they can afford to retire.
It is whether they are prepared to build a life that still feels like theirs.
And the better question for advisors is not whether AI will disrupt retirement planning.
It already has.
The real question is whether advisors will use these tools to make planning more human, more personal and more useful — or whether they will defend an old model that too often mistakes financial planning for retirement planning.