Dare to Dream or Live Someone Else's Plan

Think Like an Owner-Entrepreneur

Dare to Dream or Live Someone Else's Plan

Every year, sometime in the late fall or early winter, Ellen and I get away together. Not a vacation in the traditional sense. A retreat. A deliberate withdrawal from the operational noise of our lives for long enough to think clearly about what we actually want those lives to look like in the year ahead and beyond. We have been doing this since early in our marriage, and it is the single practice I would point to if someone asked me what has most consistently shaped the direction of our professional and personal life across thirty years.

When we first started, it was a twenty-four-hour trip to downtown Chicago. Her parents watched the kids. We drove two hours, checked into a hotel, had dinner without anyone asking for anything, and spent the next morning working through the questions in the guide I had developed for exactly this purpose. We called it Dare to Dream. We still call it that. And the guide is the same one, updated over the years, that I have made available free to every physician in this community because I believe it is one of the most practical things I have ever built.

I published the original version of this post in December 2023: Dare To Dream: Goal Setting For Physicians. The framework has not changed. What has changed is everything around it. The enterprise has grown from one professional corporation to nine micro-businesses. The children are grown. The financial complexity has multiplied in ways that make the annual retreat feel less like a nice practice and more like an operational necessity. And two and a half years of coaching conversations with physicians in this community have shown me the specific places where the original post was too brief, where it named a problem without fully describing it, and where it left the most important question about equal partnership in the goal-setting conversation as a footnote rather than a full argument. This version corrects all of that. The original is still there and worth reading as the starting point. This is the version I would write today.

As the family grew and the businesses multiplied, the retreat stretched. Twenty-four hours became forty-eight. Forty-eight became seventy-two. Now, with what we call the Stillson Enterprise spanning nine micro-businesses and a family that has grown and evolved in its own directions, it takes a full week. We go to Simpli SoHa in South Haven, Michigan more often than anywhere else. The water helps. The distance from Plymouth helps. The complete absence of clinic schedules and administrative noise helps most of all.

I want to spend today's post on why this practice matters, what happens when physicians skip it, and what the Dare to Dream framework actually covers when you sit down to use it.

The Reactive Life Is the Default Setting

The reason most physicians do not set meaningful annual goals is not that they do not care about their future. It is that the clinical schedule fills every available hour with its own demands, and those demands feel urgent in a way that makes forward-looking thinking feel like a luxury. When you are between patients and behind on your inbox and your next appointment started four minutes ago, the idea of sitting quietly and thinking about where you want to be in three years does not compete well for your attention.

What happens instead is the reactive life. You accept the next contract because it arrives when you need one. You stay in the employment arrangement you are in because leaving would require a decision that would require planning that you have not had time to do. You defer the financial goals, the adventure list, the practice model you actually want, the structural changes you know you should make, until some unnamed future moment when things settle down. That moment reliably fails to arrive.

I have had this conversation in coaching sessions hundreds of times. The physician who has been meaning to form a professional corporation for two years. The one who has been intending to negotiate a professional services agreement since the last contract renewal. The one who knows exactly what they want their professional life to look like and has not moved toward it because the day-to-day clinical load has consumed every hour available for deliberate action. The reactive life is not chosen. It accumulates, day by day, in the space that intentional planning never filled.

The antidote is not willpower. It is structure. Specifically, it is a dedicated annual retreat with the people who share your life and your financial future, in a physical space removed from the operational demands of your ordinary week, with a guide that gives the conversation direction rather than leaving it to wander.

Related resources

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

Blog: Most Physicians Are Renting Their Careers. Here's What That's Costing You.

Blog: Saying Yes to Self-Employment Is Not a Career Move. It's an Identity Decision.

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

What the Dare to Dream Retreat Actually Covers

The guide I developed for this annual retreat is organized around eight domains. I want to describe each one briefly, not as a brochure but as a real account of the conversations Ellen and I have had inside each domain over thirty years of using this framework.

Domain 1

Your Vision as a Physician Entrepreneur

Not your job description. Your vision. Where do you want to be practicing in five years, in what model, with what structure, with what relationship to the institutions and patients you serve? Most physicians have never written this down. Writing it down is the first act of owning your professional future rather than being administered into it.

Domain 2

Your Passion Projects and Creative Life

What do you want to be building outside of direct clinical care? A platform, a book, a research interest, a community involvement? This is where the physician entrepreneur identity extends beyond the micro-corporation into the full picture of what a flourishing professional life looks like for you specifically.

Domain 3

Your Micro-Corporation and Business Goals

Where is your professional corporation in its development? What structural goals belong to this year specifically? Formation, entity layering, contract renegotiation, retirement account optimization, new income channels? These are the concrete financial and structural objectives that the retreat converts from vague intentions into dated commitments.

Domain 4

Your Personal and Family Wellbeing

What does a good year look like for your marriage, your parenting, your health, your personal relationships? The adventure list that Ellen and I maintain started in one of these early retreats and has been one of the most reliable drivers of the experiences that actually define our life together rather than the ones that simply happened to us.

Domain 5

Your SMART Goals for the Year

Specific, Measurable, Achievable, Relevant, and Time-Bound. This domain converts the vision conversations from the earlier domains into concrete objectives with deadlines. The number that matters more than any other: how many of last year's SMART goals did you actually accomplish? That number tells you more about your execution discipline than any personality assessment ever will.

Domain 6

Your Community and Your Generosity

Ellen and I organize our charitable giving during this retreat because our finances have to be structured to support our values, not just our goals. We use a donor-advised fund to automate the distribution of our charitable giving once we have decided where it goes. If you do not have a donor-advised fund yet, Daffy is the resource I most often recommend to physicians who are starting to think deliberately about this dimension of their financial life. Giving intentionally is a practice, and it belongs in the goal-setting retreat alongside everything else.

Domain 7

Your Learning and Development Agenda

What do you want to know by the end of this year that you do not know now? Which skill, which certification, which body of knowledge belongs to this season of your development? The physicians who stop learning outside of clinical maintenance CE are the ones who most consistently describe their careers as stagnant five years later. Growth is not a byproduct of busyness. It is a choice that requires allocation.

Domain 8

Your Milestones and the Discipline of Celebration

We file every year's completed retreat document away with the year labeled on the outside. The stack of those documents across thirty years is one of the most vivid records of a life being deliberately built rather than reactively endured. We read back through recent years at the start of each new retreat to see what we said we wanted and whether we got it. Celebrating what actually happened, specifically and with the full weight of having chosen it, is not a soft practice. It is the feedback loop that makes the whole system work.

"We file every year's retreat document away with the year labeled on the outside. Reading back through them is one of the most vivid records of a life deliberately built rather than reactively endured."

Related resources

Blog: The Third Kind of Income Most Physicians Never Think About

Blog: Transforming Your Earnings into Passive Income and Appreciating Assets

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

Affiliate: Earned Wealth Management: physician wealth management that coordinates financial goals with the full picture of your life

Why Written Goals Outperform Intentions by a Measurable Margin

I want to make an argument for the act of writing things down that goes beyond the conventional wisdom about journaling and reflection. There is a specific mechanism by which writing a goal changes its probability of being achieved, and it is not the one most people assume.

The assumption is that writing a goal makes you remember it better. That is true but it is not the main benefit. The main benefit is that writing a goal forces you to be specific about it in a way that keeping it in your head does not. A goal that lives in your mind as "I want to have more financial flexibility" can remain in that form indefinitely without ever becoming uncomfortable. A goal on paper reads: "By December 31, we will have reduced our consumer debt by $40,000 and fully funded the solo 401(k) to the $72,000 ceiling." That goal has edges. It can be tested against reality at the end of the year. It either happened or it did not. The specificity is what makes it real, and the act of writing it is what forces the specificity.

The research on this is consistent. A 2015 study by Dominican University psychologist Dr. Gail Matthews found that people who wrote their goals down accomplished significantly more than those who did not, and that weekly accountability check-ins produced even higher completion rates. The physicians in this community who do the Dare to Dream retreat and then schedule a quarterly check-in with a coach or accountability partner accomplish more of what they set out to do than the ones who do the retreat and then file the document away until the following year. The writing matters. The accountability structure around the writing matters more.

When Ellen and I complete the retreat each year, we do not simply file the document. We build a specific review schedule into it. A midpoint check-in in June where we pull the document back out and score each goal as on track, behind, or complete. A third-quarter review in September that allows us to adjust anything that the year has made unrealistic and double down on anything we are close to achieving. The document is not a wish list. It is a working contract with our future selves, reviewed on schedule and treated with the same seriousness we bring to our financial accounts and our clinical calendars.

Related resources

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)

Blog: The Burnout Inflection Point Is the Best Time to Incorporate

The Spouse Question Nobody Talks About Honestly

I want to name something that the original version of this post touched on but did not say as directly as I want to say it here. The annual goal-setting retreat is not a solo exercise. It is a couples practice, or if you are single, a practice you do with the most trusted person in your life who understands your full financial and professional situation. For most physicians, that means doing this with your spouse or partner. And doing it well means doing it with genuine equality, which is harder than it sounds.

The physician half of a couple tends to dominate these conversations naturally. The clinical income, the professional decisions, the business structure all orbit the physician's career in ways that can quietly make the non-physician spouse feel like a participant in someone else's financial plan rather than a co-author of a shared one. I have seen this dynamic damage retreats, and I have seen it damage marriages over longer timescales when it goes uncorrected.

When we had five children under five, I had the demonstrably easier job of going to the clinic every day. The work Ellen was doing at home was not a support role for my career. It was its own full career, carried with an expertise and stamina I genuinely admired. Her goals for that season of life deserved the same weight in our retreat conversations as my professional goals did. Making sure that was actually true in practice, rather than just in principle, required intentionality that I had to learn. I did not arrive at it naturally.

If the non-physician partner in your household has drifted into the role of administrator of someone else's life plan, the annual retreat is the structural intervention that most reliably restores the balance. But only if both people come to it with an equal claim on what gets decided.

Related resources

Blog: Should You Hire Your Spouse in Your Professional Micro-Corporation?

Blog: The Home Operating System That Made Locums Work

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

The Practical Logistics That Make or Break the Retreat

I want to spend a few paragraphs on the operational mechanics of the retreat, because in my experience the physicians who have tried this practice and abandoned it most often failed not because the framework was wrong but because the logistics were not set up in a way that protected the time and the space.

The physical location matters more than most people think. The retreat needs to happen somewhere that has no operational claim on your attention. That rules out your home, which will produce an unending series of small tasks and domestic obligations that compete with the reflective work. It rules out your clinic or office. It ideally rules out any location where you are likely to run into patients, colleagues, or anyone else from your professional community who might create a social obligation that fragments the focused time. South Haven works for us partly because of the water and the beauty, and partly because no one there has any claim on our attention that would not exist in Plymouth.

The guide should be read before you arrive, not for the first time when you sit down together. Both partners reading through the Dare to Dream questions individually in the week before the retreat makes the conversation substantially more productive when you get there. You arrive with reactions already formed rather than reading a question cold and generating a first-draft answer in the room. The preparation converts the retreat from a brainstorming session into a synthesis conversation, which is a meaningfully higher-quality conversation.

The budget belongs in the retreat. Ellen and I do our personal and business budgets during this time because goals that are not financially resourced are not goals. They are wishes. If you want to take the family to Europe next summer, the budget has to show where the money comes from. If you want to max the solo 401(k) this year, the cash flow plan has to support the contribution schedule. Separating the goal conversation from the financial conversation produces aspirational goals that the real financial structure of your life cannot support. Integrating them produces goals that are genuinely achievable because you have already worked through how they get funded.

Finally: protect the time with the same discipline you would protect a surgical block or a board examination date. The annual retreat that gets rescheduled once gets rescheduled indefinitely. Put it on the calendar for the same window every year, communicate it to anyone who might otherwise claim that time, and treat a conflict as the conflict's problem rather than the retreat's problem. Twenty years from now, you will not regret having protected this time. You will regret every year you did not.

Is This Deductible?

The Annual Goal-Setting Retreat as a Business Expense

Deductible: business planning and strategy expense

The scenario: You and your spouse take a three-to-five day annual retreat to conduct strategic planning for your professional corporation and the micro-businesses that operate within your enterprise. You review the prior year's financial performance, set the coming year's business and professional goals, create the operating budgets for each entity, and make structural decisions about your professional corporation. The total cost including lodging, meals, and travel runs $2,000 to $4,000. What portion is deductible through your S-Corp?

The ruling: The portion of the retreat that is genuinely dedicated to business planning and strategy for your professional corporation is deductible as an ordinary and necessary business expense under IRC Section 162, paid through your S-Corp and documented with a written agenda, meeting notes, and receipts. The personal and family-goal components of the same retreat are not deductible and should be proportionally excluded. As your enterprise grows, the business planning proportion grows with it. At the scale where nine micro-businesses require a full week of strategic review, the business deductibility case for the full week is substantially more defensible than it would be for a sole proprietor with a single S-Corp reviewing one income stream.

The practical note: Keep a written agenda that documents specifically which hours were dedicated to business planning, which entities were reviewed, and what decisions were made. This documentation is the difference between a defensible business deduction and a personal vacation dressed up as a business expense. Work with your CPA to establish the appropriate allocation ratio for your specific enterprise.

For guidance on S-Corp business planning expense deductibility, see the free eBook Tax Deduction Guide for Micro-Business Owners (PEA Explorer) and connect with Cerebral Tax Advisors or IncSight.

Start this year

The Dare to Dream guide is free for every subscriber to this community. Download it, read through the eight domains before your next conversation with your spouse or partner, and find a weekend in the next sixty days to get away together. You do not need a week in South Haven. You need twenty-four hours away from your ordinary environment with the questions in front of you and no agenda other than to answer them honestly together.

The physicians in this community who have done the Dare to Dream retreat consistently report the same thing: it is not the goals themselves that change their trajectory. It is the act of writing them down, together, in a dedicated space, that makes them real in a way that the intention to do so eventually never achieves.

If after the retreat you find yourself wanting a thinking partner to help translate the goals into structural action, the PEA Business Coaching program at $2,000/year is where most physicians in this situation go next. Four sessions annually with a coach who understands both the professional and personal dimensions of physician entrepreneurship, designed specifically to hold you accountable to the goals you set rather than watching them slide back into the reactive life that every unexamined week tends to produce. Join the PEA community at $99/year for Explorer membership to access the Dare to Dream guide, the Mindset Shift eBook, and the full resource library that makes the retreat more productive before you even arrive.