I know that as a business owner, you’ve already accomplished something special.
And none of your success is by accident.
The fact is that you’ve made decisions when they weren’t easy. You’ve taken risks. And you’ve stayed with it when things got tough.
That’s what we business owners do.
Now, in your 50s or 60s, you’re facing a different kind of question.
What’s next?
The “What’s next?” question is the start of a conversation I have virtually every day with clients who own businesses. And yet, those conversations are rarely about whether they’ve built enough.
They are typically about whether everything they’ve built is integrated and working together. And how my role as a fee-only financial planner can help bring clarity to the bigger picture.
Your Business Is Your Biggest Asset (and Your Greatest Exposure)
For many of the business owners I work with, there’s a moment early in the conversation where we get to figuratively zoom out.
They’ve been so focused on running and growing their business, that they’ve never really stepped back to evaluate just how much of their financial life is tied to it.
And when we zoom out together it is often when they realize that your business isn’t merely an asset. It’s almost certainly THE asset.
And that realization changes how we plan.
At some point, we then need to ask:
- What is the business truly worth?
- What would it realistically sell for?
- And how much of your future depends on that outcome?
Those aren’t always comfortable questions, but they are incredibly important ones.
I often remind clients: Building wealth outside of your business does not mean a lack of confidence in your endeavor. It’s what thoughtful, protective wealth planning looks like.
Here’s what my ProsperPlan Wealth co-founder, Chris Grellas, CFP®, MSFA, had to say on the matter:
“My experience has been, that while more than 80% of a business owner’s net worth is often tied to their business, fewer than 30% have a formal exit plan.
That gap is where risk lives.
What we see in practice is that many owners assume the business will ‘take care of everything,’ but without a defined strategy around timing, valuation, and tax structure, that outcome becomes uncertain. Closing that gap by building assets outside the business and creating a clear exit path is one of the most important planning steps a business owner can take in their 50s and 60s.”
Exit Planning: The Conversation Most People Put Off
I’m going to start with the hard part, because exit planning is one of those topics that almost everyone agrees is important, but it’s also something that very few people feel a sense of urgency about until it’s close at hand.
And I understand why.
If you’re still engaged in the business, still growing, still solving problems, it can feel premature – or even uncomfortable – to think about stepping away.
But what I’ve seen over time is this:
The earlier we start talking about it, the more control you’ll have.
So, if there’s one thing I wish more business owners would do, it’s this: Start thinking about your exit before you need to.
Our clients who have the most flexibility – and the best outcomes – are usually the ones who start planning three, five, even 10 years in advance.
That kind of runway gives you options:
- You can structure the sale more thoughtfully
- You can plan around taxes instead of reacting to them
- You can choose the best possible successor and not just the available one
And, just as importantly, forward-thinking planning empowers you to make decisions from a position of calm and not urgency.
Because once you’re in the middle of a transaction, your options could start to narrow.
Working with a coordinated team, including a CPA, attorney, and a fee-only financial advisor, can make a significant difference in how that transition unfolds.
Tax Strategy Isn’t Just a Detail Anymore, It’s a Lever
Next up is tax planning. Because at this stage, it just starts to feel different.
Earlier in your career, taxes may have felt like something to manage yearly: something to minimize where and whenever possible, but not necessarily something driving big decisions.
In your 50s and 60s, that absolutely changes.
Now, your income is quite possibly at or near its peak. Your business may be more profitable (and valuable) than ever. And the decisions you make over the next several years don’t just affect you right now, they shape the long-term trajectory of your wealth.
When planning isn’t coordinated is where I see the most missed opportunity.
Because of that, we spend a lot of time helping clients think through:
- How to fully utilize retirement plan structures
- When Roth conversions actually make sense
- Whether their business structure is still optimal
- How charitable strategies can support both values and tax efficiency
And, most importantly, we make sure those decisions are connected and not happening in a vacuum.
Because throughout my two-decade-long career in finance, I long ago learned that your plan and your tax strategy should never feel like two separate conversations.
When I asked my business partner Chris Grellas to comment, this is what he said:
“In peak earning years, the right retirement structure can shelter $200,000 or more annually. Most business owners simply have not been shown how.
When you combine defined benefit plans, profit-sharing strategies, and forward-thinking coordination with your CPA, the impact compounds quickly, not just in tax savings, but in long-term retirement security.
The difference over a five- to ten-year window can be seven figures in additional net wealth, and that’s where proactive, fee-only planning really pays off.”
Retirement Income: Replacing the Engine that You’ve Built
For many business owners, income has pretty much been tied to effort.
You solve problems, you create value, you lead, and then your business generates income as a result.
So, when we start talking about retirement, there’s an unspoken question underneath it all:
What replaces that engine?
That transition – from generating income to designing it – is one of the most important shifts in this stage of life.
We walk you through questions like:
- Where should income come from first?
- How do we reduce lifetime tax exposure?
- When does Social Security fit into the picture?
- How do we bridge gaps before Medicare?
But to be sure, there’s no universal formula here. No one size fits all.
The right answer depends on your life: your goals, your spending, your health, your priorities.
But when it is done right? It replaces uncertainty with structure.
And that changes how retirement feels.
Chris summed it up perfectly when he said:
“In many cases, 70% to 90% of a business owner’s net worth is tied to a single asset. That level of concentration would never be acceptable in a traditional portfolio. Vanguard research suggests that disciplined diversification and planning can add up to 3% in net returns annually – not by outperforming markets, but by improved decision making.”
Legacy Planning: Moving From Intentions to Structure
This is usually one of the more personal parts of what is a personal conversation.
By this stage, many business owners have a powerful sense of what matters to them, including who they want to support, what they want to pass on, and what kind of impact they want to have.
But there is sometimes a gap between those intentions and a clearly defined plan.
And that is entirely normal.
Translating values into structure takes thought, coordination, and the right guidance.
At some point, those ideas need to become actionable:
- How business interests transfer
- How assets are divided fairly
- How taxes are managed
- How your expectations are actually carried out
And for business owners, those layers tend to be more involved.
That’s why we approach estate planning as part of the overall system, and not a separate task to merely check off.
Why Fee-Only Advice Matters More at This Stage
When everything starts to come together – your business, your wealth, and your future plans – the quality and kind of advice matter more.
And just as importantly, how that advice is delivered can be crucial.
A lot of people don’t realize how advisors get paid can influence their recommendations.
Because if you glean nothing else from this topic, I hope it’s this: At this stage of your career, even small misalignments and biases can have meaningful consequences.
At ProsperPlan, we are a fee-only financial advisor and planning firm. That means we do not earn commissions, referral fees, or compensation from products.
Not. Ever.
When I recommend something, or give you advice, it’s what’s best for you and your financial situation, and is never influenced by what’s best for my firm or me.
So, the conversations we have are grounded in one thing: What makes the most sense for you?
As a fiduciary, 100% fee-based advisor, that’s not just a philosophy, it’s a responsibility.
And I believe it’s the standard every client deserves.
Bringing It All Together
At the beginning of this process, things can feel fragmented.
You have a business. Investments. Tax considerations. Retirement questions. Estate planning decisions.
And all too often, each of those areas is being handled separately, or, at the very least, not fully connected or integrated.
One of the most valuable shifts I see is when those pieces start to come together.
When:
- Your business decisions
- Your personal financial plan
- Your tax strategy
- Your investment approach
…are all aligned, things start to feel different.
Clearer.
More intentional.
More manageable.
You are no longer reacting.
You are making decisions with context.
A Final Thought
You have spent decades building something.
This stage is not about starting over. It’s about making sure everything you’ve built supports you fully, and on your terms.
And when that alignment happens, something changes.
Not just financially, but personally.
If you have any questions, or you are ready to learn more, I encourage you to reach out.
With the proper planning, you will start to feel more confident and excited about what’s ahead.
