In the first part of this series, I walked through a conversation I’ve had more times than I can count.
It starts simply enough. A business owner assumes that years of hard work, reinvestment, and growth will naturally lead to a comfortable retirement. When we slow the conversation down and work backwards from what life actually costs, however, the numbers begin to tell a more complicated story.
For many people, Social Security — roughly twenty-three thousand dollars a year — turns out to be far less supportive than they expected, and a plan built around selling the business doesn’t always stretch as far as it needs to.
If you haven’t read that first piece yet, I’d encourage you to start there before continuing. It sets the context for everything that follows.
What matters here isn’t that one client’s plan fell short. It’s what happens when you run the same exercise again, with the same constraints, and arrive at a very different place.
That’s where this story begins.
The Same Exercise, A Different Starting Point
It was a gray October morning when Amanda and I sat down to talk about retirement. She had built a successful recruiting business, one that helped companies fill hard-to-place roles in niche markets and overlooked locations. The work was demanding, but it was steady, and for years it had done exactly what she needed it to do.
I did so with my previous discussion with Mike fresh in my memory. At first, I didn’t mention the outcome my previous conversation and how nervous I was to bring this up with her.
Regardless… based on her situation and goals — I knew it was time to have this discussion.
This exercise works best when it stands on its own, without comparison or expectation. So we started the same way, by talking about the end instead of the beginning.
I asked her to imagine the day the paychecks stopped and to describe what life needed to look like after that point. Not the idealized version and not the bare-bones version. Just the one that felt realistic.
She thought about it before answering.
She talked about where she lived and why it mattered to her. About flexibility and how important it was to feel like money wouldn’t dictate every decision as she got older. Travel wasn’t extravagant, but it was part of how she wanted to spend her time. Healthcare needed to be predictable. There needed to be enough cushion that one unexpected year wouldn’t force uncomfortable trade-offs.
Once the picture was clear, we started putting numbers to it. Monthly numbers, in today’s dollars.
The process was almost identical to the one I had just walked through with Mike.
A Business That Was Never Asked to Do Everything
Her business was solid, but it wasn’t enormous. It didn’t dominate its market or grow at a pace that made headlines. What it did do was evolve. She stayed current, even when that meant higher costs and thinner margins in certain years.
Innovation wasn’t cheap. There were stretches where growth felt slower than she would have liked, and years where reinvesting back into the business would have been the easier emotional choice.
But she had always been intentional about separating growth from security.
When money came in, some of it stayed in the business. Some of it didn’t.
Retirement contributions happened consistently. Employer plans were funded when they could be. Health-related accounts were used deliberately, not as an afterthought. None of this felt dramatic at the time. It was simply how she operated.
She planned, and then she followed through.
Where Social Security Fits When There’s a Plan
When Social Security came up, the number was the same as it always is. Roughly twenty-three thousand dollars a year. Just under two thousand dollars a month.
The difference wasn’t the figure itself. It was where it landed in the conversation.
Instead of trying to make it stretch or relying on it to fill a gap, we placed it at the bottom of the stack. It wasn’t the answer. It was the baseline.
Everything else was built above it.
As we laid her expected income next to the lifestyle we had just mapped out, the tone of the room stayed steady. The numbers weren’t perfect, but they were workable. There was room to adjust. There were options.
She didn’t lean back in her chair. Instead, she leaned forward.
Planning That Turned Into Momentum
What stood out wasn’t the size of her accounts. It was how they had been built.
She didn’t describe planning as something abstract. She talked about years where contributions went out even when cash flow felt tight. Years where skipping would have been easy and defensible, but wasn’t done. Years where adjustments were made instead of avoidance.
The plan didn’t live in theory. It lived in execution.
Over time, that execution compounded quietly. The accounts grew. Pressure eased. The business became something she could choose to continue, not something she needed to depend on for survival.
By the time we finished the exercise, she was in her early fifties with roughly six million dollars set aside and a succession plan already taking shape. She wasn’t eager to retire, but she didn’t need to wait either.
The option existed.
Why the Outcome Felt So Different
What stayed with me afterward was how similar the starting points had been.
Both clients were smart. and had worked very hard to gain success. They had made decisions that felt reasonable when they made them.
The difference wasn’t intelligence or effort. It wasn’t luck.
Rather, it was intentional planning carried through with consistent execution.
One plan relied heavily on a future event lining up at the right time. The other was reinforced year after year, even when it wasn’t exciting or convenient.
As we wrapped up, she asked a question that sounded almost casual.
“So I don’t have to decide anything right now, do I?”
She didn’t.
That, more than anything else, was the result of the work she had done years earlier.
Where This Leads Next
These two conversations happened close together. The questions were the same. The constraints were the same. The math didn’t change.
What changed was what had been put in place before the exercise ever began.
In the next part, I want to slow this down even further and look at what actually happens when planning is executed over time. Not in theory, and not in abstractions, but in real dollars. How money compounds when it’s given room to work, and why starting earlier changes the outcome more than most people expect.
That’s where the mechanics come into focus.
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.
