You Can't Take It With You. Live Without Regret

Think Like an Owner-Entrepreneur

You Can't Take It With You. Live Without Regret

In June 2024 I published a post called Embracing Wealth and Life: You Can't Take It with You, But You Can Live Without Regret. It drew on a conversation Jordan Grumet had with the White Coat Investor about his book "Taking Stock: A Hospice Doctor's Advice on Financial Independence, Building Wealth, and Living a Regret-Free Life." The original post named the right ideas. It did not press them hard enough into the specific territory where the physician entrepreneur lives.

This version does.

The physician who has spent years in this community learning to build a micro-corporation, optimize their tax structure, diversify their income channels, and compound their retained income toward financial independence is developing a specific and genuinely valuable skill set. The risk that comes with that skill set is also specific: it is possible to become so competent at building the financial structure that the life the structure was supposed to fund gets permanently deferred. Not abandoned, not forgotten, but always one more milestone away. One more year of savings. One more income channel. One more optimization. And then the window closes in ways that no retirement account can reopen.

That is the version of the regret problem that belongs in a Wednesday post in this community. It is not the generic "money isn't everything" observation that appears in thousands of personal finance articles. It is the specific vulnerability of the physician who has figured out how to build wealth and who, in doing so, has given themselves a new way to procrastinate on living.

What Jordan Grumet Heard at the End of Life

Jordan Grumet is a hospice doctor who spent years sitting with people in the final weeks and days of their lives. His book is worth reading by every physician in this community, not primarily as a financial planning resource but as a clinical account of what people say when the financial planning is behind them and the life is almost over.

What he heard, repeatedly, was not regret about financial decisions. Nobody dying told him they wished they had saved more, earned more, or optimized their tax structure more aggressively. What he heard, in varying forms across hundreds of conversations, was regret about the things that money could have enabled and did not, because the accumulation of money had become the activity that crowded out the activities money was supposed to make possible. Relationships that were rationed. Adventures that were deferred. Work that was continued past the point where it was meaningful because the financial independence target kept moving. A self that was promised a life once the wealth was built, and who waited for that promise to be kept while the years in which it could have been kept ran out.

Grumet's phrase, which I return to regularly, is that money is a tool, not the end goal. It is meant to buy freedom and time. The physician who treats their solo 401(k) optimization as the end goal and freedom and time as the reward they will claim once the number is right has confused the instrument for the outcome. The instrument is excellent. The confusion is costly.

"Nobody dying told Jordan Grumet they wished they had saved more. What he heard was regret about the things money could have enabled and did not, because the accumulation of money had become the activity that crowded out the activities money was supposed to make possible."

Related resources

Blog: Embracing Wealth and Life: You Can't Take It with You (original 2024 post)

Book: Taking Stock by Jordan Grumet (White Coat Investor interview)

Blog: Building Wealth Means Nothing If You Neglect This

Blog: We Crossed Lambeau Off the List. Here Is What Happened.

The Specific Vulnerability of the Physician Entrepreneur

I want to name this more precisely than the original post did, because the physician entrepreneur's version of the regret risk is different from the general version of it.

The general version goes like this: people defer life in favor of work, and they regret it. That version is true and the research on it is consistent. But it does not quite capture what happens to the physician who has gone through the identity shift from employee to owner, who has built a micro-corporation, who has developed the discipline to max a solo 401(k) and run an accountable plan and optimize a salary-versus-distribution split. That physician has developed something that feels productively oriented. Each new optimization produces a real and measurable result. The retained income number goes up. The net worth meter advances. The retirement date gets closer. There is genuine positive feedback in all of it, and positive feedback is exactly what makes a behavior self-reinforcing.

The risk is that the owner-physician identity, which is a fundamentally productive and valuable identity to develop, can also produce a physician who is permanently in building mode and who treats the living of the life as the thing that happens after the building is finished. The building is never quite finished. That is the nature of building. And so the life that was supposed to begin when the building was done never quite begins.

I have had this conversation in coaching sessions more times than I can count, in one form or another. The physician who is deeply engaged with the financial structure, who has done the work in this community, who genuinely understands the retained income math and is executing on it, and who, when pressed on what the financial independence is actually for, gives an answer that sounds like a plan they have not yet made. "Travel more." "Spend more time with the family." "Pursue the things I have been putting off." These are real intentions. They are not a plan. And without a plan, they remain intentions indefinitely while the financial structure grows around them like a very well-optimized cage.

Related resources

Blog: Dare to Dream or Live Someone Else's Plan

Blog: Creating an Adventure List: Experiences that Forge Bonds and Create Lifelong Memories

Free guide: Dare to Dream: Goal-Setting Guide for Physician Entrepreneurs (subscriber free)

Free eBook: Business Mindset Shift: Mapping the Transformation of Your Professional Identity (PEA Explorer)

The Five Questions Worth Asking Annually

The original post offered five generic steps. These five questions are the versions of those steps that the physician entrepreneur actually needs to sit with, specifically and honestly, at the annual Dare to Dream retreat or whenever they have the uninterrupted time to give them genuine attention.

Question 1

What would I regret not doing if I had five years left?

This is Grumet's question, and it is a good one because it bypasses the financial constraints that most physicians use as a reason not to answer it and goes directly to the desire. The answer to this question is usually available to the physician asking it. The more common problem is that the answer has been available for years and the question has not been asked with the seriousness it deserves. Write the answer down. If you have been meaning to see the national parks, attend a Bears-Packers game at Lambeau, take your kids somewhere you have always talked about taking them, or simply be more present in the ordinary days of your life than the clinical schedule and the entrepreneurial build have allowed, those answers are the beginning of a plan. Write them as a plan with dates, not as aspirations with good intentions.

Question 2

Who has experienced my absence more than my presence?

This question is the one that requires the most honesty and the most courage to answer accurately. The spouse who has been supporting the career while the career has been consuming the household energy. The children who know intellectually that you love them and have experienced practically that your attention is divided. The friendships that have survived on insufficient investment because the schedule never quite had room for them. The physician entrepreneur who answers this question honestly and then does something deliberate about the answer, rather than resolving to do better in a general way, is making the most important investment available to them that does not appear in any financial model.

Question 3

Is my financial independence target a number or a life?

There is a meaningful difference between having a net worth target and having a picture of what the life enabled by that net worth looks like, feels like, and is built around. The physician who knows their number but cannot describe the morning of a typical day at financial independence, what they are doing, with whom, toward what, has a target without a destination. The Dare to Dream annual retreat is the right format for this conversation, and the question that belongs at its center is not "how much do we need?" but "what does the life we are building toward actually look like?" The number should follow from the life, not the other way around.

Question 4

What experiences have I been promising myself that I keep deferring?

The adventure list that Ellen and I have maintained for thirty years is the practical tool that prevents this question from producing only regret. Every item on the list that has been crossed off is an experience that did not get indefinitely deferred. Every item still on the list is a commitment we made to ourselves that we have not yet honored. The annual retreat is the moment to look at both lists honestly and decide what gets scheduled in the coming year with real dates rather than "someday." A Lambeau game that has been on the list for fifteen years and finally has tickets purchased for it is categorically different from a Lambeau game that has been on the list for fifteen years and is still on the list. The scheduling is the commitment. Everything before the scheduling is an intention.

Question 5

When did I last do something purely for the joy of it?

The physician entrepreneur who cannot answer this question without thinking for an uncomfortable length of time has allowed the productive identity to crowd out the person who inhabits it. Financial independence is not primarily about the number. It is about the recovery of a self that can do things for the joy of doing them without calculating their return on investment. The Coast FIRE concept, which describes the point at which retirement accounts already funded will grow to the target number without additional contributions, is relevant here not only as a financial milestone but as a permission structure. The physician who has reached Coast FIRE has earned the right to reduce the clinical schedule, take the trip, show up at the baseball game, and pursue the creative or community or relational interests that the building years compressed into the margins. They do not always give themselves that permission. That is what this question is asking them to examine.

The Retirement I Did Not Know I Was Planning

I want to close this post with something personal, because the abstract argument for living without regret is less persuasive than the concrete account of what it looks like when someone chooses it deliberately.

I retired from a twenty-seven-year clinical practice in Plymouth, Indiana earlier this year. I did not retire because I ran out of clinical capacity or because the work was no longer meaningful. I retired because the financial structure I had spent twenty-plus years building had produced the freedom to make professional decisions without the income requirement driving them, and I made the decision to use that freedom rather than continue accumulating in the absence of a compelling reason to do so.

Ellen and I spent this past fall at Lambeau Field for a Bears-Packers game, something we had been talking about doing for years and had never quite scheduled. We drove through the changing leaves in northern Wisconsin. We spent four days in a football town that organized itself around a hundred years of one institution, watched 81,000 people in the same building at the same moment, and came home with a memory that belongs to us now in a way it did not before we went. We are already talking about the next one.

That trip happened because the financial structure made it possible and because we made the decision to do it rather than add it to the list of things we would do when the building was more complete. The building is never more complete. The decision to live the life the building was supposed to enable is a decision, not a consequence of the building. You have to make it deliberately. And if you wait for the building to be finished before you make it, you may find that the window for some of what you wanted has closed.

Grumet's hospice patients did not regret the things they tried and did not get quite right. They regretted the things they did not try at all. That is the version of the regret that the physician entrepreneur, of all people, has the resources to avoid. The financial structure exists to give you choices. Make the choices.

Related resources

Blog: Coast FIRE: A Strategic Path for Self-Employed Doctors

Blog: The End of an Era. What the Exam Room Gave Me.

Free eBook: Design Your Career Around Your Life: The Physician's Guide to Professional Freedom (subscriber free)

Affiliate: Earned Wealth Management: physician financial planning that integrates life goals with wealth strategy

Case Study: Dr. Abramowitz's Permission Problem

Dr. Abramowitz (name protected) is an orthopedic surgeon who came to a coaching session at age fifty-six with a net worth of approximately $4.8 million, a solo 401(k) he had been maxing for eleven years, a real estate portfolio producing meaningful passive income, and a question that surprised me by how long it took him to articulate. He had done everything right financially. He knew he had done everything right. He was asking whether he had permission to stop.

He had three children he described as growing up faster than he had expected. He had a wife he described as "incredibly patient," which is a specific kind of compliment that carries a specific kind of freight. He had a list of things he had been meaning to do that he had maintained in his head rather than on paper, because writing them down would have made the gap between intention and action visible in a way that was uncomfortable. He had reached Coast FIRE approximately two years earlier, which meant the retirement accounts already funded would grow to his target number by sixty-five without additional contributions. He had not reduced his clinical schedule by a single hour after crossing that threshold.

We spent the session not on financial planning but on the question of what he was waiting for. The answer, when it finally came, was that he did not feel like he had earned the permission to step back. The financial structure said he had. His own sense of what he was supposed to be doing had not caught up with what the financial structure was telling him.

He reduced his clinical schedule by 0.2 FTE within sixty days of the session. He and his wife took a trip they had been talking about for eight years. He attended his youngest son's baseball games for a full season for the first time since the boy had started playing. He told me in a follow-up conversation that none of those things had required any adjustment in their household's financial situation, because the financial situation had been ready for them for two years. He had not been ready.

The financial independence is not the destination. The willingness to inhabit the freedom it buys is the destination. Those are different things, and the distance between them is a decision, not a financial calculation.

Build the wealth and live the life

The physician entrepreneur who has done the work in this community, who has the professional corporation in place and the retirement accounts growing and the income channels diversified, has built something real and worth building. The argument in today's post is not that the building is wrong. It is that the building has to be in service of a life that is being lived, not a life that begins after the building is complete, because that day tends to arrive later than intended and shorter than deserved.

The Dare to Dream guide is where the annual conversation about what the wealth is actually for belongs. It is free for every subscriber to this community. The CME Away program is the structural tool that converts professional obligations into shared adventures. The Coast FIRE post covers the financial milestone that, when you cross it, gives you structural permission to reduce the clinical schedule without compromising the retirement trajectory.

Book a $500 Business Strategy Session when you are ready to have the conversation about what the financial structure you have built is actually supposed to enable, and to make a deliberate plan for enabling it rather than continuing to defer. Join the PEA community at $99/year for Explorer membership for the full resource library. Grumet's patients did not regret the things they tried. Make the list. Schedule the trip. Cross something off. That is what the wealth is for.