Case Studies
Three stories about the questions people bring to us, and how we would work through them.
Hypothetical examples. These stories are illustrative, combine situations commonly faced by people like our clients, and do not describe any actual client. Individual circumstances and results vary.
Business Owner: Prep for Life After Exit
The situation
Consider Andrea (56) and Paul (54), who bought a small heating and cooling company seventeen years ago, when it had a handful of trucks and an owner ready to retire. Today it has a few dozen employees and a steady reputation, and its profit has paid for a comfortable life. It also holds most of their wealth and most of their calendar. Neither of them can remember a vacation that passed without at least one call from a dispatcher.
A business broker has given them a general sense of what companies like theirs sometimes sell for, and they can picture selling in two to four years. Their daughter is in college and has chosen a different career. Their son is a high school sophomore, and they are aware that the years when he is still at home are passing too. They want to know what a sale would leave them after taxes and transaction costs, and whether they could step away sooner than they have been telling themselves. After seventeen years of arranging family life around the busy season, they are also unsure what they would want an ordinary Tuesday to look like.
They do not see that last part the same way yet. Andrea is ready to be done. Paul suspects he would miss the work and might want a smaller role in something. The biggest risk they face is making a major decision about the sale before either of them understands what they need it to do.
At a glance
Who: Andrea, 56, and Paul, 54, who own a heating and cooling company with a few dozen employees
On the table: A possible sale in two to four years
Questions on their minds:
What a sale would leave them after taxes and transaction costs
Whether they could step away sooner
What an ordinary week would look like once the company no longer fills it
How much of their wealth and attention is tied up in one business
What the planning would cover:
Each spouse's picture of life after the company
Sale date and price scenarios
The timing of an earlier or later sale
Coordination with their CPA and attorney
Cash flow and investing after a sale
Insurance and estate documents
The work
Here is how we would approach it. The choices would be theirs. Our part would be to ask the questions and build the analysis, with their CPA and attorney at the table.
Start with each of their pictures of life after the company
We would begin with each of them separately, then together, on what they imagine for the years after ownership. If one of them is ready to stop altogether and the other wants to stay involved in something, that difference shapes what a good sale looks like, including how long either would stay on afterward.
Put a realistic range around the number
Next we would model several sale dates and prices alongside estimated transaction costs and taxes, their household spending, health insurance for the years before Medicare, and the larger goals they have in mind, such as their son's college costs and the travel they keep postponing. A price a broker mentions in conversation says very little about how much would be left to fund life after a sale.
Test the timing
We would compare selling in two years with working four more, including the effect of continued earnings and saving, and how much of their wealth would stay tied to a single company in the meantime. Seeing what each path costs and what it gives them, in financial security and in time, lets them weigh the tradeoff with both sides in view.
Bring in the CPA and the transaction attorney early
Entity structure, tax considerations, retirement plan contributions, and any charitable or estate-planning opportunities all take time to evaluate. We would bring their CPA and the attorney who would handle a sale, along with any other specialists, into the conversation early enough to look at those questions before a deal is imminent.
Plan the cash flow that follows
We would also map how sale proceeds could be invested and drawn on, separating the money they would need in the first few years from the money meant to support decades of living. The first covers near-term spending. The second belongs in a diversified portfolio built for the long term. We would also review the insurance and estate documents that were built for a business owner's household, since a sale changes what they would need to protect.
Make room for the human side
Finally, we would talk concretely about what an ideal week looks like for each of them after the sale, and which relationships with employees and customers they want to keep. We would also talk about what work Paul might take on and how Andrea wants to use the time the company now occupies.
Photo is a model, not a client.
What a good outcome would look like
Before serious negotiations begin, they would ideally understand a reasonable range of after-tax outcomes and the tradeoffs of selling sooner or later. They would also have a clear sense of what the life they want would require financially. With that in hand, Andrea and Paul can weigh an offer against their own priorities, and the largest number becomes one input among several. The decision would be theirs, made with the full picture in view.
Planning like this cannot predict what a company will sell for or how a negotiation will go, and no outcome is guaranteed. Its purpose is a well-informed transition, financially and personally.
If you own a business and have started to wonder what a sale would need to do for you, the Exploration Call is a relaxed 30-minute conversation to see whether working together makes sense. You don't need to prepare anything.
Hypothetical example. This story is illustrative, combines situations commonly faced by people like our clients, and does not describe any actual client. It does not describe results achieved and is not a recommendation for your situation. Individual circumstances and results vary.
Burnt Out Entrepreneur
The situation
Consider Caroline (44) and Marcus (46). Fourteen years ago Caroline opened a small-animal veterinary practice with one exam room and one receptionist. It has grown to three exam rooms and now brings in about one and a half million dollars a year, and it sits in a building that she and Marcus own through an LLC and rent to the practice. Caroline pays herself a salary of about $150,000 and takes profit distributions of $175,000 to $250,000, depending on the year. Marcus is a civil engineer for a county government. Their children are in second and fourth grade.
By any outside measure the practice is a success. Caroline is the lead doctor four days a week, and she is also the person who reads every application when a technician leaves. Two associate veterinarians cover most of the other days, and a third position has been open for eight months. The vendor contracts and payroll reports wait until the children are in bed. She does each of these jobs well, and together they leave her tired in a way a weekend does not repair.
On a Tuesday evening in the fall, Caroline is still at her desk at 7:40 when Marcus texts a photo of the dinner table with her plate covered. The week before, a neighbor picked up their younger child from school because a surgery ran long. At home her phone sits on the kitchen counter, screen up, in case the after-hours line needs her. Some days the hardest conversations are with families facing the end of a pet's life, and by the time she gets home she is quiet. Marcus has learned to let her be. Everyone in town knows her as Dr. Caroline, and when someone asked her recently what she does for fun, she did not have an answer ready.
Marcus has watched this for a few years. He has never asked her to sell or to stay. A few weeks ago he asked what she would do if she ever had a full day to herself, and she found she did not know. Last month a letter arrived from a company that buys practices like hers. She has not answered it and has not thrown it away.
They work with a CPA who handles the S corporation and the LLC, and with an attorney who wrote the lease. Most of what they own sits in the practice and the building, and their insurance and estate documents were last reviewed before the children were born. No one has put the whole picture together. They both want Caroline to have more of her own days, and they want whatever they decide about the practice to be a choice they make together.
At a glance
Who: Caroline, 44, who owns a small-animal veterinary practice, and Marcus, 46, with two children in elementary school
On the table: A practice that takes most of Caroline's energy, and an unanswered letter from a company that buys practices
Questions on their minds:
What Caroline's days could look like if her role changed
What their household would need from the practice to support that
How much of what they own rests on one practice and one building
What answering the letter would mean for their taxes, income, and time
What the planning would cover:
Life Planning conversations
Household cash flow and Caroline's pay from the practice
Tax and entity questions, with their CPA
The building and the lease, with their attorney
Insurance and estate planning
Retirement and investing outside the practice
The work
Here is how we would approach it. The choices would be Caroline and Marcus's. Our part would be to ask the questions and build the analysis, with their CPA and attorney at the table.
Start with the week they want
We would begin with Life Planning conversations, with each of them separately and then together. What does a good week look like in a good year, and how many of those days does Caroline want to spend with patients? Caroline's identity as a doctor matters to her, and so does the person she is outside the exam room, and we would make room for both.
Lay out the whole financial picture
Next we would build the picture of their finances: what the household spends, what the practice pays Caroline and how much that varies, the debt on the building, and what they own outside the practice. Much of their wealth rests on one practice and one building, and we would show what that depends on.
Test the choices that would give her time back
We would model the ideas they bring: fewer clinical days for Caroline, a hospital administrator to take over staffing and vendors, higher pay to recruit and keep associate doctors, a triage service for after-hours calls. Each costs something in profit, and so in household income. We would show what each would do to their cash flow and long-term goals, so they can choose with the cost and the benefit in view.
Bring in the CPA and the attorney early
How much salary is reasonable for a doctor who works fewer days, and how that fits with distributions and the rent the practice pays their LLC, is a question for their CPA. We would make sure it gets asked while the schedule is still on paper. The lease and the building's role in any sale are for their attorney. We do not give legal or tax advice, and we would coordinate those conversations.
Protect the household and build outside the practice
Because the household's income passes through one person's ability to work, we would review disability and life insurance, along with an estate plan that names guardians for the children and reflects the practice and the building. We would also look at retirement savings and at how to invest outside the practice, sizing a long-term portfolio to what they would need and when.
Weigh the letter as one option among several
Buyers of practices often ask the owner to stay on as a doctor for several years, and offers can combine cash with notes or stock. The building could be sold with the practice or kept and leased to a buyer. Each path affects taxes, income, and flexibility differently, and their CPA and attorney would read the actual terms. We would help Caroline and Marcus set any offer beside the week they described. They could sell, or keep the practice and change how Caroline works in it, and the timing would be theirs to choose.
Photo is a model, not a client.
What a good outcome would look like
Ideally, Caroline and Marcus would be able to say in their own words what a good week looks like and how many of its days Caroline spends with patients. They would know what that life costs, which income would pay for it, and how each path would affect their taxes and their household income. They would have protections in place for a household that has depended on one person's health.
With the whole picture in view, they could decide about the letter with confidence in the reasoning behind it. They might reduce Caroline's clinical days, add an administrator, plan a sale for a date they choose, or keep things as they are, and any of those would be their decision.
Planning like this cannot predict what a practice would sell for or how any investment will perform, and no outcome is guaranteed. Its purpose is to help them make decisions with the full picture in front of them, and to keep revisiting those decisions as their lives change.
If you own a business that is going well and has started to take more of you than you expected, the Exploration Call is a relaxed 30-minute conversation to see whether working together makes sense. You don't need to prepare anything.
Hypothetical example. This story is illustrative, combines situations commonly faced by people like our clients, and does not describe any actual client. It does not describe results achieved and is not a recommendation for your situation. Individual circumstances and results vary.
Pro Athlete: Maximizing Your Playing Years
The situation
Consider Caleb, a professional athlete who is 29 and in his seventh season. His wife Nora designs packaging for a handful of freelance clients, work she has built around the team's schedule and carried through two trades. They have a two-year-old daughter and a baby due in the spring. They rent, because they have learned not to assume they will be anywhere for long.
Caleb's salary is larger than anything either of them grew up around, and both of them know it has an end date they cannot see. Many professional athletes find their peak earning years are behind them by their mid-30s, with thirty or more working years still ahead. A contract can go unrenewed, or a body can stop cooperating. They already work with an advisor who manages Caleb's investments and an accountant who files his tax returns, which cover more than one state. Their financial goals and a spending plan for life after playing are still undefined, and no one is putting the pieces together.
They are unusually aligned about what they want. They would like to live in one place long enough to put down roots, and they want Caleb to have time to work out what comes next, a question he has not had to ask himself since he was eighteen. What they need is a plan for the financial life that begins after the final whistle.
Photo is a model, not a client.
At a glance
Who: Caleb, 29, a professional athlete in his seventh season, and his wife Nora, with a two-year-old daughter and a baby on the way
On the table: A career with no fixed end date, and a family that wants to put down roots
Questions on their minds:
What life costs once the salary stops
Which of their assets would pay for it
A large taxable account with a heavy tax cost if sold
What Caleb would want to do next
What the planning would cover:
Life Planning conversations
Household spending and future goals
Retirement accounts
The taxable account
Insurance and estate planning
A plan that can change when the contract does
The work
Here is how we would approach it. The choices would be theirs. Our part would be to ask the questions and build the analysis, with their CPA and attorney at the table.
Start with the life they want
We would begin with Life Planning conversations about what each of them pictures for the years after playing, then turn those priorities into financial decisions.
Put numbers around life after the game
We would work out the family's monthly spending today and map the expenses they expect ahead, including a first home, flights to see relatives, vehicles, and the other goals they care about. Because the salary will stop at some point, the aim is to understand how much of that life they would need their savings and investments to cover, and for how long.
Bring the retirement accounts into one picture
We would go through the retirement plan he has through the team and a rollover IRA from an earlier stretch, so that the long-term investment strategy is easier to manage.
Handle the taxable account with care
Caleb's brokerage account grew out of a few positions he bought early and never revisited. Selling them to start fresh could produce a large tax bill, so we would evaluate how a move toward a more deliberate allocation might be paced, with the tax cost of each step in view and his accountant involved. No single approach suits everyone.
Protect the family while the income lasts
Because the family's income depends on one person's health and one contract, we would look at disability and life insurance and at an estate plan that names guardians for their children. Caleb's advisor and accountant would be part of those conversations.
Adjust when the plan changes
Now suppose the team decides partway through not to renew his contract. A retirement date that was a few years away becomes a question about this season. We would treat the plan as something that can change, and rework it for one more contract and for none. The uncertainty in a career like this does not go away. The plan's job is to keep the decisions in a sensible order when the timing moves.
Make room for what comes next
We would also talk about what Caleb might want to do after playing, whether that means staying in the game in some form or something entirely different, and about what an ordinary week looks like with both parents home.
What a good outcome would look like
Ideally, Caleb and Nora would have a clear picture of what their life costs and which assets would pay for it, along with a plan for the taxable account that accounts for taxes. They would also know the order in which the decisions need to be made, whenever the final season arrives. Where they live and what Caleb does next would be theirs to decide, and the plan's job would be to make those choices workable.
For an athlete with a short earning window, much of the value in planning is in the details: decisions made in the right order, with room for the plan to change. Planning cannot predict how long a career will last or guarantee any financial outcome.
If you are earning at a high level for a limited stretch and building a family at the same time, the Exploration Call is a relaxed 30-minute conversation to see whether working together makes sense. You don't need to prepare anything.
Hypothetical example. This story is illustrative, combines situations commonly faced by people like our clients, and does not describe any actual client. It does not describe results achieved and is not a recommendation for your situation. Individual circumstances and results vary.
What are you waiting for?
This is your one life. You deserve to have a clear path to live it on your terms.
Lighthouse Planning LLC [advisory services offered through ... per Form ADV; CCO to supply the exact registration wording]. Registration does not imply a certain level of skill or training. The case studies on this page are hypothetical examples for educational purposes. They do not describe any actual client or any results achieved, are not personalized investment, legal, or tax advice, and the strategies mentioned may not be suitable for you. Lighthouse Planning does not provide legal or tax advice [CCO to confirm]. Investing involves risk, including the possible loss of principal. Diversification does not guarantee a profit or protect against loss. Planning does not guarantee any particular result. Photos are models, not clients.