By the time I finished working with both Mike and Amanda, the contrast between their situations was obvious — but not for the reasons most people expect.
It had nothing to do with how hard they worked, how smart they were, or how ambitious their businesses had been. Once we stripped all of that away, they were trying to solve the same problem.
They both wanted to retire.
Neither of them wanted to disappear or radically change their lives. They wanted to stop working on their terms, keep their homes, stay engaged with family, see their grandkids grow up, take a few trips each year, and live with the same level of comfort they were used to.
That shared goal is where the real work began.
Where I Always Start the Conversation
Before we talked about accounts, strategies, or exit plans, I wanted to understand what retirement actually needed to support. Not an idealized version of life, but the one they were already living.
We started with housing. Between property taxes, insurance, utilities, and maintenance, both households landed in roughly the same place. Just keeping the house running came out to about twelve thousand dollars a year.
Then we moved to food and everyday living. Groceries, transportation, household expenses, subscriptions, and the steady costs that never feel dangerous until you add them up. That number was closer to fifteen thousand a year.
Healthcare came next. Nothing extreme. Just premiums, deductibles, prescriptions, and the assumption that medical costs don’t get cheaper with age. Add modest travel and a buffer for the years that don’t go according to plan, and the annual cost of simply maintaining their lifestyle became clear.
None of this was extravagant. It was ordinary. That’s exactly why it mattered. Only after those numbers were on the table did we talk about income.
Why?
Unless you know what (or how much) you’re going to need in retirement — how can you know that you’re not going to run out of money at some point in the future?
Where Social Security Fits — And Where It Doesn’t
Social Security came into both conversations the same way, because the number is the same for everyone. Roughly twenty-three thousand dollars a year.
When you place that next to the cost of living we had just outlined, it becomes clear very quickly what it can and cannot do. It helps. It does not come close to carrying the load once salary income disappears.
That realization tends to land quietly.
For both clients, the question stopped being about benefits and started being about everything else. If the government check wasn’t going to support their lifestyle, then the rest had to come from somewhere — and that “somewhere” needed to exist before retirement arrived.
That’s the gap most people underestimate.
Same Math, Different Situations
Here’s where the stories diverged.
In Amanda’s case, much of that gap was already being filled. Over the years, she had consistently redirected profits out of her business and into retirement accounts and other income-producing assets. Those dollars had time to compound. They weren’t dependent on her working, or on selling the business at exactly the right moment.
When we ran the numbers, there was no scramble. The structure was already doing its job. Our work focused on making sure assumptions still held, adjusting for changes in tax law, and de-risking where appropriate. She didn’t need to reinvent anything. She needed to stay disciplined. If anything, she probably was taking too much risk and needed to re-allocate some of her retirement into more safe-guarded assets.
Retirement wasn’t a cliff for her. It was a decision she could make when she was ready.
Mike’s situation looked different once the math was on the table.
His lifestyle costs were similar. His goals were similar. The gap between Social Security and what he needed to live was similar. What wasn’t similar was how that gap was being handled.
Too much of his plan relied on one future event: selling the business. Until that happened, very little was being built outside of it. When we worked backwards from age sixty-five, it became clear that hoping the sale would solve everything was no longer enough.
So the focus changed.
Instead of asking how to grow faster, we started redirecting cash flow. Profits that had always gone back into expansion began moving into retirement plans and income-producing assets. The business still mattered, but it could no longer be asked to do all the work on its own.
Because Mike was starting later, the plan needed to move with more urgency. Contributions mattered more. Execution mattered more. Time wasn’t an abstract concept anymore — it was a constraint we had to respect.
That didn’t mean it was too late. It meant the plan had to be honest.
What This Means for You
This is usually the moment where the conversation changes pace. Not because anyone has been told what to do, but because the numbers stop being abstract.
When people finally see how little of their lifestyle is covered once salary income disappears, it becomes harder to push the question aside. That’s when retirement stops being a distant idea and starts feeling like something that deserves attention now, not later.
Both clients wanted to retire, had similar expectations for what retirement looked like, and faced the same Social Security reality.
The difference wasn’t desire. It was whether the gap between their expenses and guaranteed income had already been addressed — or whether it was still being deferred.
If you haven’t done this math yet, there’s a good chance your plan is still built around assumptions. Assumptions about how long you’ll wor, what the business will be worth, and how much you’ll really need to actually retire.
Those assumptions don’t usually fail all at once. They fail quietly, as time removes flexibility.
Being honest about the numbers doesn’t mean something is wrong. It means you’re finally working with reality instead of optimism.
For some people, that honesty confirms they’re on track. For others, it forces a change in direction. In both cases, action becomes clearer once the math is visible.
So… Can You Actually Retire at 65?
The answer isn’t tied to age. It’s tied to preparation… and in some cases your preparation.
If the years leading up to sixty-five have been used to build income that exists outside of your labor, retirement becomes an option. If they haven’t, sixty-five turns into a deadline that forces decisions instead of offering them.
Social Security won’t save you. It was never designed to. Its function is to supplement.
What determines whether you can retire is whether you’ve been willing to look at the numbers early enough to do something about them.
For some people, that work is already underway. For others, it needs to start now. Either way, pretending the math doesn’t matter doesn’t make it go away.
Being honest about it does.
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.
