When should I sell my business: four dated signals to check in the next 24 months

Before 55: can the business run without you?

Start with one name. Write down the manager, lead machinist or co-owner whose departure would change what a buyer pays, and next to it the date that person might retire, sign elsewhere or ask to be bought out. That is your first dated signal, and it costs nothing to gather.

If you can't name anyone, that's information too: a buyer will see a company that depends on you. Most owners under 55 have time to fix that, and the fix adds value whether you later sell, hand the shop to a daughter or son, or sell to employees.

In your 50s, dates start narrowing the window

Pull the lease, the bank loan, your biggest customer contract and each key employee agreement, and put the expiration dates on one page. Then hold them against a realistic window for marketing and closing, which a business broker and your attorney can estimate for your trade.

A renewal isn't automatically a reason to sell or to wait. A long lease renewal can help a buyer see stable occupancy. A costly commitment signed just before a sale can leave you with less room to negotiate, because the buyer may want different terms.

The screen below assumes you are weighing a sale within two years. Each row turns one signal into a number you write down and a next action.

Tax work comes after the date range. Once you have a likely closing range, Apollon Wealth Management estimates what the sale will owe in federal tax and sets up estimated payments (individuals use IRS Form 1040-ES) so an underpayment penalty doesn't surprise you. But that estimate shouldn't decide the business question by itself.

Moving a close from December to January shifts the tax cost into another year; it rarely removes it. What changes the number is price, deal structure and how the proceeds are allocated, and your CPA and attorney have to confirm that.

Renewals cut both ways

Tax work follows the closing range

How much is one more year really buying in your early 60s?

One more year buys another year of profit and a chance to raise the price, but it also adds another year of concentration, key-person and health risk. It's worth it when a dated plan, such as a successor taking over duties, improves the business that year; it isn't when you are simply hoping for a better offer.

Take Merle, a hypothetical person: 68, widowed, owner of a machine shop worth about $2.5 million. He has two adult daughters, one working in the shop, plus $900,000 in IRAs and a $90,000 taxable reserve for near-term spending. (He's past his early 60s, but the same screen works at 62 or 68.)

His measured net worth is $2,500,000 + $900,000 + $90,000 = $3,490,000. The shop is $2,500,000 ÷ $3,490,000 = 71.6 percent of that, below the three-quarters rule of thumb, so concentration alone doesn't force a sale. He has five years before required distributions normally begin at 73. Merle sets a decision date 12 months out and spends the time documenting his daughter's operating role and testing whether the employees can keep the shop running. If a new valuation comes in, he divides it by the updated total again before that date.

Merle weighs three paths on the same criteria, over a 12-month horizon.

Acting too early is the first timing error. Accepting a sale process before your records, operating roles and personal spending needs have been tested leaves you negotiating under pressure, and diligence will find the gaps for you.

Waiting is the opposite error. Owners who hold out for the top offer because that's what everyone tells them can end up at the table after a key operator has left, the lease has renewed or their health has narrowed the choices.

If you still earn W-2 wages through an S corporation, 401(k) deferrals come from those wages, not from shareholder distributions. The IRS employee deferral limit for 2026 is $24,500, plus an $8,000 catch-up at 50 and over, or $11,250 at ages 60 through 63. That can help the last operating years, but it won't make a weak sale date strong. Returns on any reinvested proceeds are never certain, and investments can lose money.

Merle's concentration check

Two timing errors and one tax-calendar note

At 68 and beyond, are you waiting for a reason or a date?

Waiting for a reason without a date usually means waiting for a problem to pick the date for you. At 68 and beyond, put three dates on one page: when required minimum distributions start, how many months your health lets you lead the shop, and when your operator could run it without you.

The IRS starts required minimum distributions at 73, or 75 if you were born in 1960 or later. That date alone doesn't require a sale; it only tells you when IRA money starts coming out whether you need it or not.

A large sale can reach your Medicare Part B premium two years later. CMS sets the 2026 standard premium at $202.90 per month, and the total reaches $689.90 per month at $500,000 of income for a single filer, or $750,000 for a joint return.

Choosing a January or December close only to shift income is the wrong-order error. You then discover the buyer, lease or financing deadline made a different date worth more. Timely estimated payments can manage the federal underpayment exposure, but they don't erase the tax cost.

The close date comes last

The two-year question for Apollon Wealth Management

Bring this one: what event in the next two years would make waiting to sell clearly worse? Add the lease and loan dates, the names and expected timelines of your key operators, a rough personal balance sheet and the latest business valuation. Apollon Wealth Management can put those dates and the estimated tax cost in decision order, while your legal, valuation and tax professionals confirm their own parts. A timing screen can't value the company or predict an offer, and it can't tell you whether a gift, family transfer or employee sale fits better.