Pre-Retirement Roadmap for the Entrepreneur

You spent years grinding. Maybe you ran a business, maybe two. Bought the building, sold the building. Took the risk, made the leap, caught your breath—and it paid off. Now the hustle’s slowing down, and you’re staring down the next chapter: the not-quite-retired years. So... what now?

Let’s talk.

You're Not Done—You're Just Switching Gears

See, wealth-building is active. Loud. It comes with late nights, real estate deals, spreadsheets, market swings, maybe even a few impulsive investments that either made you look like a genius—or nearly gave you a heart attack. Pre-retirement, though? It’s quieter. Strategic. Less thrill, more thought.

But make no mistake: this phase matters just as much. Because how you manage your money now sets the tone for how you’ll live in retirement—not just survive it.

So, where do you start?

1. Shift from Building to Fortifying (but Don't Get Boring)

Let me guess—you spent your 30s and 40s saying things like “I’ll take the risk, I’ve got time.” Now? That timeline’s looking a little tighter. Doesn’t mean you pull out of the market and bury cash in your backyard. It just means adjusting the mix. In preparation for what’s next

Asset allocation becomes the name of the game. More bonds, maybe. Dividend-paying stocks, perhaps. Real estate that cash flows, possibly. Maybe a few “fun” investments—but it all depends on your goals and needs.

And hey, you don’t have to kill your entrepreneurial spirit—just calibrate it. This is about sustainability, not adrenaline.

2. Get Cozy with Your Cash Flow

You’d be surprised how many successful folks can’t answer this simple question: “What does your lifestyle actually cost?” Not your theoretical budget—the real, messy, shopping-heavy one. And we CANNOT forget about health care costs and home maintenance.

Figure that out. Then build a plan that supports it without draining your principal. We’re talking about retirement income planning, which is way more than just withdrawing 4% a year. (That rule? A good start—but it’s not gospel.)

You’ll want to look at your Diversified Income Strategy:

• Social Security timing (yes, it matters)

• Required minimum distributions (and how to minimize taxes)

• Pension income (yes, some folks still have pension income)

• Investment income (retirement accounts, non-qualified, real estate, business income)

• Working part-time or consulting (your wisdom, knowledge, and skills can be in demand)

• Inheritances and trusts (even unpredictable inheritance absolutely need to be considered)

It’s a puzzle. But the picture is worth it.

3. Taxes: The Silent Profit Killer

Here’s a harsh truth—making money is only half the win. Keeping it? That’s the real skill. Especially when there are other hands in your retirement cookie jar.

Think about:

• Possible Roth conversions while you’re in a lower tax bracket

• Tax-advanced strategic philanthropy if you're charitably inclined

• Qualified charitable distributions (QCDs) after 70 1/2?

• Strategic withdrawals from tax-deferred vs. taxable accounts

• Potential tax-loss harvesting to minimize unrealized capital gain

A good tax strategy can save you tens of thousands over time. Maybe more. Talk to a pro—this isn’t the time for online DIY software and wishful thinking.

4. Talk Legacy Before It’s Too Late

Okay, let’s get a little uncomfortable. Do you want to leave something behind? Or do you want your last check to bounce?

Either answer is fine. What’s not fine? Leaving it all to chance and assuming your kids (or nieces, or charities, or golf buddy Steve) will just “figure it out.”

Get your estate plan done—really done. That means:

• A will (duh)

• A revocable living trust (maybe)

• Powers of attorney and health care directives (yes, now)

• Beneficiary designations (update them—please)

And talk about it. Seriously. Money secrecy is outdated. You don’t have to give your kids access, but giving them context? That’s respect.

5. Redefine What “Retirement” Even Means

One more thing—retirement isn’t a cliff you fall off. It’s a transition. And if you’re anything like the people I work with, you’re not dreaming of a quiet porch swing and 4PM dinners.

Maybe you want to consult part-time. Mentor younger business owners. Travel. Start a vineyard, who knows?

You’ve got financial freedom now. Don’t let it sit in a vault. Make it fuel something meaningful. Something fun. Something that gets you out of bed in the morning with a little grin.

Final Thought: Your Wealth Deserves a Plan—So Do You

This chapter isn’t about proving anything. It’s about helping protect what you’ve built, making informed moves, and deciding how you want to live—with purpose, ease, and maybe a bit of flair.

So yeah—you built your wealth. Now it’s time to build your life around it.

If you're looking for guidance, clarity, or just someone who won't glaze over when you talk about your entrepreneurial idea, I'd love to help. Because you've got options—and they're a whole lot better when you plan ahead.

Let's talk about what's next.