Gratitude + Gifting: How One Business Owner Learned to Help His Family Without Creating Future Issues
At our estate planning firm, we meet a lot of business owners who look a lot like Cole.
We will start with the Monday before Christmas, when he was staring at a stack of holiday cards and a spreadsheet he refused to open.
He was very good at building his company. He wasn’t nearly as good at dealing with anything that looked like paperwork for his personal life.
Business had been incredible that year. The company hit numbers he used to only joke about. A national retailer signed a big contract. His leadership team kept texting him celebratory gifs.
His kids noticed too.
“Daddy, did the business really double this year?” his daughter, Caroline, had asked over dinner. She was twenty-four, newly engaged, and dreaming about a house that did not feel like a cramped rental.
His younger son, Luke, still in college, had his own wish list. “Tuition, the truck, the apartment. It would be nice if I could just focus on school,” he said one night.
Cole heard all of it. He also heard his older brother, Wes, mention “tight months at the shop” and his parents worrying about medical bills. Success was starting to feel like a weight as much as a gift. Everyone seemed to look at him a little differently.
So now he was at his desk with a pen in his hand, feeling uncharacteristically stuck.
He wanted to show his gratitude. He also did not want to make a giant mess.
“Fine,” he muttered. “Let’s just be Santa.”
He grabbed his checkbook and started writing: ten thousand for Caroline and her fiancé to put toward a house, eight thousand for Luke to clear his credit card and travel abroad, five thousand each for his parents and for Wes.
It felt generous, and it felt loving.
It also felt a tiny bit like panic.
He slipped the checks into holiday cards, wrote quick notes, and shoved them into a drawer for Christmas Day. The whole thing took twenty minutes.
Then he opened the spreadsheet he had been avoiding. It was not from his accountant. It was the asset worksheet from his estate planning file that our office had asked him to update and send back.
As he scrolled, he noticed a section he had skimmed right past the first time:
“Lifetime gifts to children: unknown, estimated six figures.
Informal loans to family: not documented.”
He stared at the words. Then he reached for his phone.
“Hey, this is Cole,” he told our receptionist. “I think I am about to do something dumb with holiday gifts. Is there any chance I can talk with one of the attorneys today?”
We found him a spot on the calendar.
The Story Behind the Checks
When he walked into our conference room that afternoon, Cole looked exactly like most of our business owner clients look in November. Successful. Tired. Carrying a manila folder full of half-finished paperwork.
“You have that face,” his attorney said as she sat down. “The I-did-something-but-I-don’t-know-if-it-was-smart face.”
Cole laughed and pulled the holiday cards out of his bag.
“I was going to hand these out at Christmas,” he said. “The business crushed it this year. I want to help. I also do not want to blow up my estate plan or have my kids hating each other in ten years over who got what.”
The attorney opened one envelope, saw the check, and nodded.
“Okay,” she said. “This is very on brand for you. Big heart, fast decisions. Tell me what is going on in your head.”
“I feel guilty,” he confessed. “Caroline is looking at houses. I know what is in my accounts. I can help. Luke is juggling tuition and odd jobs. My parents are stressed. Wes’s shop is struggling. It feels wrong to sit on this success and not share it.”
“That part makes perfect sense,” she said. “Your instinct to give is a good one. The only problem is the way you have been doing it and how it fits with your planning documents.”
Feel-Good vs Strategic
The attorney opened Cole’s estate planning file and turned a summary sheet so he could see it.
“Look,” she said. “You have been doing what we see a lot: feel-good gifting. It looks like this.”
She pointed to a section she had annotated.
- Big holiday checks based on how you feel that month
- Helping one person with a house, another with a business, without much record
- Paying tuition, rent, and random expenses directly, then forgetting about it
- Talking about ‘getting the business out of your estate’ in bits and pieces without a real structure
Cole read the list and winced.
“Fine. Guilty. That is exactly what I do. It feels nice, though.”
“It does,” she agreed. “For a while. Until someone asks a question like, ‘When you helped Caroline with the house, was that supposed to count toward her inheritance?’ Or your executor has to decide whether those ‘loans’ are real loans or gifts. That is when things get tense.”
She tapped another page.
“Strategic gifting is not less generous. It just pays attention to the legal and family consequences. It looks more like this.”
She summarized.
- Gifts planned inside your bigger estate and tax picture
- Clear instructions in your documents about what is a gift, what is a loan, and how that should be treated later
- A framework to stay fair to your kids, even if the help looks different
- Coordination between your gifts, your will and trust, and your business succession plan
Cole sat back.
“So, in other words, I am already giving a lot. I am just doing it in the most chaotic way possible from a legal standpoint.”
“Basically,” she said, smiling. “The good news is you can clean this up. You do not have to stop being generous. We just need the generosity to match what your estate plan actually says.”
The Ghost Loans
She pulled a sheet from the file labeled “Family Gifts / Loans.”
“Let me show you something else,” she said. “When we first drafted your plan, we tried to tally the help you had already given your kids and your brother. These numbers are rough, because there was almost no documentation.”
Cole groaned.
“Hit me.”
“Caroline: help with moving expenses, a used car, some credit card payoffs, plus the ‘probable’ house contribution you mentioned. Luke: tuition for three years, a trip abroad, a car insurance fund. On top of that, Wes’s shop got a fifty thousand ‘loan’ that nobody has talked about in two years.”
He rubbed his forehead.
“I thought we were keeping it about even. Maybe a little tilted toward Caroline. She is older. That is what I told myself.”
“Which is fine,” the attorney said. “The problem is that in your head, there is a whole story. You remember the timing, the reasons, the context. If you are not here to explain it someday, your kids and your brother will see only numbers and very little guidance.”
Cole pictured Caroline and Luke arguing across a conference table while a stranger read his will. His stomach tightened.
“So what do we do?” he asked.
A Different Kind of Holiday Plan
The attorney slid the stack of holiday cards back toward him.
“Let’s press pause on these for a second. I am not telling you that you cannot give. I am saying we step out of panic mode and into plan mode.”
“Okay,” he said. “Tell me what plan mode looks like. I can do plans.”
“You handle plans all day in your business,” she said. “This is the same skill set, just pointed at your family.”
She held up a finger.
“First, for the checks you already wrote. If you want to give those amounts this year, you can. We will note them as gifts and update the internal schedule we keep with your trust. You will tell your kids and your family that you are being intentional about gifts, not random.”
He nodded.
“Second, any money that you want back eventually must become a real loan. That includes Wes’s shop loan if you want repayment. We draft a simple promissory note, set expectations, and reference that in your planning file. That way, if you later decide to forgive it, it is a clear decision, not a mystery.”
“Right now it is a mystery,” he admitted.
“Exactly,” she said. “Third, we need to decide whether some of the help you want to give should go through a trust instead of directly. Especially if you worry about draining their motivation or watching a future ex-spouse walk away with part of what you gave.”
He thought about Caroline’s fiancé, who was great but still new to the family.
“I had not even thought about divorce,” he said quietly.
“That is what your estate plan is for,” the attorney replied. “You are not trying to control your kids. You are giving them structure. A trust can say, ‘This money is for education, health, maybe a home purchase,’ without dropping the full amount in their checking account. It also gives some protection if life gets messy.”
The Business Question
Cole leaned forward.
“What about the company?” he asked. “I always hear people say you should gift business interests early to get it out of your estate.”
The attorney smiled.
“There it is,” she said. “One of my favorite dangerous half-truths.”
He laughed.
“So that is not automatically smart?”
“It might be smart for you,” she said. “We just cannot decide that in a vacuum. Before your estate plan starts giving away pieces of your company, we need to answer some things.”
She ticked them off.
“Do Caroline and Luke actually want to own part of this business? Do you want them as co-owners in any capacity? How would that affect control and decision-making while you are alive? What does your operating agreement or buy-sell say? If one child works in the business and the other does not, how do we keep the peace in your documents instead of hoping emotions sort it out later?”
He had no answer for any of that.
“I always assumed I would just figure it out later,” he admitted.
“That is most owners’ plan,” she said. “Here is what I recommend. For this year, your holiday gifts look like cash and maybe help toward specific goals. Next, we schedule a focused meeting on business succession. Once you know what you want your exit and your legacy to look like, any gifts of business interests can follow that plan instead of fighting it.”
“So basically, I do not touch the company with holiday gifting.”
“Correct,” she said. “You keep control. Your employees are not surprised by new family co-owners. Your kids still feel supported because they see intentional generosity, not random checks.”
The Conversation at the Table
On Christmas Day, Cole took a deep breath before walking into the living room with the stack of envelopes.
His parents were on the couch. Wes stood by the kitchen, talking with Luke about football. Caroline and her fiancé were near the fireplace, scrolling through house listings on a phone.
Cole cleared his throat lightly.
“Hey, can I grab everyone for a minute?” he asked.
They all turned.
“This year was big for the business,” he began. “I am very grateful. I also know that each of you has had your own financial stress. I want to help where I can. I also want to do it in a way that is fair and makes sense over time, so I have been working with my estate planning attorney on a bigger plan.”
Caroline raised an eyebrow. This already sounded different.
He held up the envelopes.
“These are gifts for this year,” he said. “Not loans. You do not owe them back. I am keeping track of what I give so that later, if anything happens to me, there is a clear record. If we help someone with a house, or school, or a business idea, it will be part of an overall plan, not a secret side deal.”
Wes shifted.
“What about the loan for the shop?” Wes asked.
“I talked to my attorney about that,” Cole said. “We are going to put that in writing, just like I would with any other business loan. That way, if I forgive it, it is clear in my documents and nobody has to guess. For now, I want you to know it is not floating in limbo.”
There was a pause. Then his mom smiled.
“I like that you are thinking ahead,” she said. “We never talked about this kind of thing with our parents.”
Caroline looked at her fiancé, then back at her father.
“Does this mean if you help us with a house, it is going to be written down too?” she asked.
“Yes,” he said. “If I help, it is part of a bigger story, not a one-off. I am updating my will and trust so that the help I give during my lifetime and what you receive later all work together. It feels a little awkward to say all this out loud, but I want you to know it is intentional. No favorites. No secrets.”
Luke grinned.
“So I can still cash this?” he asked, waving his envelope.
Cole laughed.
“Yes, you can cash it. I will just make sure my lawyer writes it down this time.”
After the Dishes
Later that night, after everyone had left and the house was quiet, Cole sat at the table again with a yellow pad.
At the top of the page, he wrote:
“Gifts in the last three years.”
He listed:
- The car for Caroline
- The extra semester of tuition for Luke
- The loan for Wes’s shop
- This year’s holiday checks
- The times he had quietly paid medical bills or rent for his parents
It was not perfect. He knew he would miss a few things. Still, it felt like a start.
He drew a line under the list and wrote one more sentence.
“Next: send this list to my attorney, talk about trusts, and schedule a real business succession meeting.”
He exhaled.
For the first time in a long time, his generosity felt less like a pile of random receipts and more like the beginning of a plan that matched his estate documents.
He still got to play Santa. He just was not leaving behind a legal scavenger hunt for his family and his future executor.
The business could keep booming. His family could feel supported. And the story of his giving could stay clear and organized inside a plan that would outlast any single holiday season.
If Cole’s Story Feels Familiar, This Is Your Gentle Nudge
If you saw pieces of your own life in Cole’s yellow pad list, you are not alone.
Most successful business owners mean well. They help with down payments, tuition, medical bills, startup money for a sibling, all with a generous heart and a mental note to “sort it out later.”
The law does not see those moments the way your family does. Courts and executors pay attention to what is written, what is documented, and what your estate plan actually says. That gap between what you intended and what is on paper is where confusion and conflict usually show up.
The good news is that you do not have to stop being generous. You simply bring your giving into the same level of intention you already use in your business:
- Make a simple list of the gifts and “loans” you have given in the last few years
- Decide which ones are truly gifts and which ones should be treated as loans
- Talk with an estate planning attorney about whether trusts or updates to your will and trust make sense, especially if you own a closely held business
If Cole’s Christmas conversation sounded like something you wish your family could have, this is a good time to take the next step.
Our firm helps business owners turn scattered generosity into a clear, written plan that supports the people they love and protects the company they built.
If you are ready to make sure your holiday gifts fit your bigger legacy, contact our office at (615) 933-7636 to schedule a time to talk about your own “Cole list” before the next holiday season rolls around.