People occasionally ask me what the secret is to what I do. I don’t think there is a secret to financial planning. In fact, if another firm took our exact playbook and tried to run it, it probably wouldn’t work. Every firm has different people, different leaders, different cultures, and different clients. Staying true to your strengths is foundational for success.

If there’s no secret, then what makes an effective financial professional? One study suggests that clients value many aspects of the client–advisor relationship, including transparency in fees, trust, and the advisor’s knowledge. However, topping the group is advice that “factors in all aspects of their lives.”¹

Over time, I’ve found that one of my strengths is identifying the factors in all aspects of a client’s life, and spotting what is most important to the client. It is not always the first thing they say, or even the clearest thing on the page. Often, it sits underneath the goal, the number, or the question they bring into the room. My job is to help find it.

Effective Professionals Focus on Experiences Instead of Outputs

I find that what matters in this industry isn’t a secret; it’s about having a principled approach to guiding the planning experience. One of these principles, I believe, is that our industry sometimes loses sight of what financial planning is supposed to accomplish. We become focused on plans, reports, projections, and deliverables.

My goal is to ensure those things never become the client’s experience of financial planning. They’re out there experiencing life, and that’s why I believe planning is a verb, not a noun, and this should guide us. It means the plan must keep moving with the client as their life changes, not sit still as a document that was more relevant one day six months ago than it is today.

The best plans are those that are updated constantly, revised, adjusted and re-examined. In theory, a great plan would continuously update with new data in real time, because then our work could truly shift to helping people use planning to make better decisions in the moments that matter. Put another way, planning should be about helping people live more intentionally.

Our Firm Doesn’t Count Plans, We Count Lives More Fully Lived

That is also why our firm does not measure success by how many plans we produce, and though we enjoy growing AUM, it’s not a key metric. A plan can be beautifully built and technically sound, but if the client never gains confidence, never acts, and never moves closer to what matters most to them, we have to ask whether the work really succeeded.

The plan matters. The experience matters more. And the math matters, too, but only when it applies to the human interaction, the human need, and what the human sitting across the table from me values and prioritizes.

The industry can get trapped in what I think of as the math checklist:

• Round numbers
• Return assumptions
• Retirement projections
• Monte Carlo outcomes

All of that is necessary, but none of it is sufficient. Because people do not live inside spreadsheets. They live inside families, careers, businesses, ambitions, fears, health events, transitions, and decisions that rarely feel as clean as the model makes them look.

We try not to count plans as if the number of documents created tells the whole story. We pay more attention to what the planning process helps the client do:

• Clarify what they want
• Understand the tradeoffs in front of them
• Make decisions with greater confidence
• Act when action is needed
• Recognize progress in their real life, not just in a report

That is the standard I keep coming back to. Not whether we produced an impressive plan, but whether the client left the process with a clearer sense of direction and a stronger ability to live the life they were planning for.

Helping People Run Their Own Race

We have a recurring idea I come back to often: we want clients to run their own race. This analogy matters to me because it is not theoretical. Running a marathon teaches you very quickly that somebody else’s pace can ruin your race. If you spend the whole time looking left and right, comparing yourself to everyone around you, you can lose the discipline to run the race you actually trained for.

I think the same thing happens in financial planning. Too many people measure success against neighbors, coworkers, friends, or the social circles they happen to be in. They see what someone else bought, where someone else moved, when someone else retired, or how someone else talks about money, and suddenly their own plan starts to feel inadequate.

But financial planning should not be about somebody else’s finish line. It should help clients define success for themselves—and build a plan around it. This is why personalization matters.

That requires the advisor to slow the conversation down and help the client separate comparison from clarity. The question is not whether the client is keeping up with someone else. The question is whether the plan reflects what they value, where they are trying to go, and what kind of life they want to build.

In practice, that means helping clients ask themselves:

• What race am I trying to run?
• What would success look like if I stopped comparing myself to others?
• Which goals are truly mine and which ones did I absorb from the world around me?
• What pace can I sustain without losing sight of the life I want?

When clients get clear on those answers, the plan becomes more personal and more durable. It is no longer a scorecard against someone else’s life. It becomes a way to stay oriented toward their own values, their own tradeoffs, and their own definition of progress.

Math Is a Must, But Meaning Is What Matters

Math matters. It has to—we’re dealing with money. A financial plan needs strong assumptions, thoughtful projections, and technical accuracy. But math alone is not the point of the work. The numbers only become meaningful when they connect to the client’s actual life—their decisions, pressures, relationships, and the future they are trying to create.

If a client tells me they want a certain dollar amount, I can run the numbers. I can show the path, the probability, and the variables that matter. But the better question is often what that number represents. Is it security? Freedom? The ability to sell a business? The chance to spend more time with family? A way to stop worrying? Until we understand that, we are only solving for a number, not for a person.

That is the difference between planning as a deliverable and planning as an experience. The deliverable may show what is possible. The experience helps the client understand what matters, what tradeoffs they are willing to make, and what kind of future they actually want to move toward.

Always ask yourself:

• What does this goal represent in the client’s life?
• What decision does the client need to feel confident making?
• What tradeoffs are they willing—or unwilling—to accept?
• What would make the outcome feel successful beyond the numbers?

That is why I believe great planning starts by putting the client’s need in front of the technical answer. The spreadsheet can tell us whether something is possible. The conversation helps us understand whether it is meaningful, whether it is worth pursuing, and what the client needs to feel confident enough to act.

The Best Discovery Question Isn’t Financial

Once clients stop measuring themselves against someone else’s finish line, the planner or advisor can ask a better kind of question. Not just, “Can we get you there?” but “Will you really be happier if you achieve that?”

If a client says the goal is to have $20 million, the real discovery question may be, “Is the $20 million really important to you?” and “Why?”

It’s also important to ask for context starting with discovery. Don’t wait until you build the relationship. Build the relationship through the process of discovery.

Now you’re not just solving for a number. You’re discovering what that number means to the client and what it means for the plan. In many cases these are what motivate clients’ financial decisions:

• Freedom
• Status
• Dream fulfillment
• Validation
• Time
• An opportunity
• A second chance

When it comes to these underlying motivations, the number is rarely the point; it’s about what that number means in relation to that client’s life.

Why Technology and AI Make Human Advice More Valuable

I am not fearful of emerging technologies such as AI. If technology can handle more of the mechanics, as I see it doing, great. Let it help with the spreadsheets, summaries, and repeatable work that often consume an advisor’s time.

That should give planners and advisors more room to build relationships; to ask better questions, interpret the meaning behind the numbers, and help clients make decisions they can live with.

Over time, the spreadsheet will not be the differentiator. The human connection will be, and the planner or advisor who can combine technical fluency with judgment, empathy, and context will become more valuable, not less.

The Future Is About Knowing Your Clients, Not Markets

Years later, I received a photo of the original plan from a client. Attached was a note: “As you predicted, I made it.”

That moment stayed with me. Not because the client remembered a report, a cash flow projection, or a set of assumptions. They remembered the experience of working toward a life they hoped was possible.

To me, that is planning at its best. It is not about being right, producing the plan, or proving the math. It is about helping someone move with confidence toward life behind the numbers. That is why planning will always be an always on activity to me, and a verb, not a noun.

Learn more about finding the meaning behind the plan in Helping Clients Find a Deeper Meaning for Their Money.

¹ Why Advisers Need the Humanity of Money, Financial Planning Association, 2024

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