Reflections on a Quiet Failure

A week ago I posted “The Quiet Failure of Good Advice.” More than two dozen of you replied with experience, candor, and care. Thank you, sincerely. I’ve been thinking about what you wrote, and I wanted to come back and share what I took from it.

A few patterns kept surfacing.

The first is structural. Several of you named the same diagnosis: financial planning as a profession is calibrated to serve the wealthy. Mike Lynch, a retired CFP and longtime industry educator, put it more sharply than I would have dared: most financial advisors are not, in fact, advisors. They sell products or services. Their economics reward selling and managing assets, not educating households. The result is that people without significant assets, those just starting out, or those navigating financial transitions on their own are economically uninteresting to most of the profession. In a follow-up that I keep returning to, Mark Crothers described how the UK system handles this differently — automatic enrollment, payroll-handled tax compliance, free government-provided retirement guidance through Pension Wise. His phrase for the population the UK system tries to serve was “the disengaged majority.” That’s a structural reframe worth sitting with. The US system arguably offers more for those who actively engage with it, but it rewards financial literacy and punishes inertia in equal measure. The UK system, by contrast, is designed around the people who aren’t reading Humble Dollar.

The second is a use case I didn’t expect to see emerge so strongly. Several of you — Mike Lynch, Akhil Lamba, John Verlautz, and others — engaged a financial advisor specifically to protect a spouse who isn’t financially active, often after a health scare or as part of late-career preparation. Bob Drahushuk named a related but distinct motivation: an awareness of his own potential cognitive decline, and a desire to set up his sons for the eventual onboarding of an IRA inheritance. Even highly capable self-directed investors recognize a moment when planning is no longer optional. Marion Morton’s story illustrated the same truth from the other side: after her husband’s death, a fee-based CFP became invaluable in what she called a brutal administrative period. The financial planning a family needs may be most visible at exactly the moments when one partner has to navigate alone.

The third is a word I kept hearing, whether written or not: holistic. Rick Connor named it directly; several others described it without using the term. The form of planning many agree has real value is not investment advice in isolation but a coordinated view across investments, insurance, tax, estate, retirement income, and cash flow. The planners who do that work seem to be in the minority, and they are rarely the ones available to households without significant assets. S Sevcik’s experience with her father’s care complicated this further: even a salaried fiduciary advisor can produce blinkered recommendations because the institutional model doesn’t see what isn’t in its view. Bias, as she put it, is everywhere and entirely unavoidable.

The fourth observation came from Rick Connor and was echoed by Mike Lynch and Steve Spinella: there is no pro-bono planning equivalent to the volunteer tax preparation programs (VITA, AARP Tax-Aide). Tax compliance has a volunteer infrastructure; planning does not. Several of you mentioned volunteering — for taxes, for SHIP, for community boards. The infrastructure to do the same kind of work for basic financial planning simply isn’t built yet. Mike Lynch’s pro-bono ministry work and Steve Spinella’s thinking about combining therapy and financial coaching point to where some of that infrastructure might emerge, but they remain individual efforts.

And then there is the avoidance loop — D.J.’s phrase, but a theme several of you named in different ways. People are most uncomfortable talking about money precisely when they have not managed it well, which is, of course, when they would stand the most to gain. The longer they put off the conversation, the harder it becomes. DrLefty named the simpler version of this: if you’re living paycheck to paycheck, you’re not thinking about planning. You’re just surviving. Stacey added a generational dimension — folks aren’t thinking of their 60, 70, 80 year-old selves when they’re trying to make it to the next payday.

John Thieme offered the deepest version of this insight, drawn from his Habitat for Humanity work: the difference between households that escape generational poverty and those that don’t often begins with the discipline of setting a goal at all. He shared an illustration his local affiliate uses — what item can be found in every wealthy and middle-class home but is much less likely to be found among those in poverty? A calendar. The first step for many people in breaking generational patterns is learning to set a goal, develop steps toward it, and accept coaching and accountability. The financial planning conversation, framed this way, isn’t really about products or portfolios. It’s about an orientation toward the future that some households have inherited and others haven’t.

And yet — as Ormode reminded us — even when good advice is offered freely and directly, it isn’t always accepted. The 65-year-old he tried to warn, taking 5% withdrawals and paying 1% AUM, didn’t want to hear it. She needed the money to stay in her retirement community. Sometimes the barrier isn’t on the delivery side. Sometimes it’s on the reception side.

What I take from all of this is twofold. The problem is real and structural — not a matter of individual responsibility or financial illiteracy that more reading could fix. And several of you have been thinking about this gap for longer than I have, often from inside the planning profession or from adjacent disciplines. The pro-bono and ministry-based efforts you described, and others I’ve learned about since, are early signs of a quiet movement trying to extend planning to people the existing market overlooks.

I’m working on something in this direction — a tool, in software, that tries to make the work of comprehensive financial planning available to households who would never engage with a traditional planner. What it does, and whether it works, is a conversation for another day. But the conversation in this thread has sharpened my thinking about who it is for and what it has to do. For that, I’m grateful.

In all this thread has said about the means and barriers of financial planning, it has said very little about its purpose. That absence may itself be revealing. Two questions, then, if you’re willing.

First: What do you think the goal of financial planning should be? Not its tools or methods — but the thing it’s ultimately in service of.

Second: Whether your financial planning has been self-directed or purchased, how do you measure its success?