Have you ever contemplated what your life will look like in retirement. Studies show that less than 60% have a retirement account. To make things worse, very few of them have them appropriately funded.
This is a conversation most entrepreneurs don’t avoid on purpose. It simply gets pushed aside while the business is growing, expanding, and demanding attention every day. When you’re focused on building something meaningful, thinking too far ahead can feel unnecessary, even distracting.
Over the next few pieces, I want to slow that conversation down and walk through it carefully. I’ll share how two different clients approached this question from very different places, made decisions that felt reasonable at the time, and ended up with outcomes neither of them fully expected. The contrast between their paths is where the story lives — not because one was right and the other was wrong, but because time has a way of revealing things effort alone can’t.
This is going to be a long walk where I share how two different clients tackled this in a very differrent eay and how the outcome was mayb e not what you’d expect.
When I talk with business owners about retirement, I don’t start with age or when they want to stop working or what they’ve heard they should be doing.
I start by asking them to picture a specific moment.
The day they wake up and there’s no paycheck coming in anymore. Not because something went wrong. Just because time did what it always does.
Then I ask a question that usually changes the tone of the room.
“If that day were today, how much would it take — right now — for you to live the rest of your life without constantly worrying about money?”
Not extravagantly. Not perfectly. Just comfortably. With enough margin that one unexpected year doesn’t undo everything.
That’s where this conversation started with him.
A Plan That Had Always Worked
Meet John… a successful business owner in his mid-50s. He had spent decades building a business that did exactly what it was supposed to do. When money came in, it went right back out into growth. New equipment, new systems, new ideas. He wasn’t chasing shortcuts. He was reinvesting in something he understood.
For a long time, the strategy paid off. When the topic of retirement came up, he didn’t hesitate.
“I’ll sell the business at sixty-five.”
It wasn’t said defensively or optimistically. It was said as a statement of fact, the way people talk about something they’ve assumed for years. The business had always been the answer.
So instead of questioning the plan, I asked him to walk me through his life after the sale.
Where he would live. What kind of home still felt like home at that stage. How often he expected to travel. What healthcare needed to look like so it didn’t rely on best-case scenarios. How much cushion made him feel like one bad year wouldn’t force uncomfortable decisions.
We moved slowly. Nothing about the conversation felt rushed.
Once the picture was clear, we started putting numbers to it. Monthly numbers, in today’s dollars. The kind of numbers that don’t leave much room for interpretation.
That’s when the question stopped being theoretical.
Where Social Security Actually Fits
At some point — it always happens — Social Security came up. Not as a plan. More like a background assumption. Something familiar that would help.
I asked him if he knew what it actually paid.
When I told him the number, I didn’t dress it up or qualify it. I just said it plainly. According to the Social Security Administration, the average benefit today is roughly twenty-three thousand dollars per year. Just under two thousand dollars a month.
He didn’t react right away. He looked back at the page where we had written down his expected monthly expenses, then back up at me.
“Did I really work my tail off my whole life for twenty-three grand a year?”
As you may have guessed at this point… I had to edit that statement quite a lot before it went into this article. Anyways, I digress.
He wasn’t being dramatic. Honestly, he didn’t even seem angry. At this point I think he was simply trying to reconcile two numbers that didn’t belong on the same page.
The Gap You Don’t See Until You Look for It
Social Security was never meant to cover everything. It was designed to supplement something else. In his case, that “something else” was supposed to be the business.
So we turned back to it.
What could it realistically sell for today? Once taxes have been deducted, what was the principle he could use for his retirement? Would that amount generate enough income once it was no longer tied to daily operations?
This is usually the part where people expect relief. Where the numbers come together and the gap closes.
Needless to say… this time — they didn’t.
Even using reasonable assumptions, the income didn’t support the lifestyle we had just mapped out. Not immediately, but over time. The kind of shortfall that doesn’t announce itself all at once, but slowly tightens.
He leaned back in his chair and asked the question that had been building since we started.
“So… what now?”
As shocking as this was… I could see why he had been a successful businessman. Let’s face the facts and find a way to fix it!
When the Plan Stops Cooperating
Nothing about his approach had been careless. Reinvesting in the business made sense for years. The returns justified it. The growth was real.
What changed wasn’t his work ethic or his intelligence.
What changed was the environment around him.
Technology moved faster than expected. The industry evolved. The business that once looked like a dependable exit was now worth far less than he had anticipated. Not because he failed, but because the world didn’t pause while he was building.
And his entire retirement plan depended on one outcome happening at one point in time.
When that assumption no longer held, the rest of the plan struggled to stand on its own.
Why This Question Matters
This isn’t an unusual story. It’s a common one.
Most people don’t sit down and work backwards from the life they want at sixty-five. They assume they’ll do it later, once the business slows down or the timing feels right.
The problem is that timing has a way of deciding things for you.
This exercise doesn’t tell you what to do next. It doesn’t offer solutions. It simply forces clarity where assumptions used to live.
Not long after this conversation, I walked through the same process with another client. We started in the same place, with the same question and the same constraints. On the surface, nothing about the exercise was different.
The outcome was…. that’s where this series goes next.
Welcome to the New Age of Accounting. Let’s begin.
P.S. If you found this article helpful, you’ll love my new book S-Corp Mastery: How Smart Business Owners Maximize Tax Savings & Build a Lasting Legacy. It’s now live and available in a sleek, easy-to-read PDF version. Grab your copy here.
Chris is the Managing Partner at Weston Tax Associates, a best-selling author, and a renowned tax strategist. With over 20 years of expertise in tax and corporate finance, he simplifies complex tax concepts into actionable strategies that drive business growth. Originally from Sweden, he now lives in Florida with his wife and two sons.
