How to Navigate the Silence After Your Business Sells for $5 Million: Tips From a Financial Planner

Selling your business for a huge sum is a major milestone, but the silence that follows can be disorienting. It's essential to pause, redefine your identity and focus on purpose over profit before rushing into the next big thing.

By Dennis D. Coughlin, CFP, AIF

published 12 January 2026

in Features

A smiling older man relaxes on the sofa and looks at his laptop.

On the morning after the sale of your business, the wire hits your account. You open your phone.

There it is — $5 million.

For a few seconds, your shoulders drop. The stress, the deadlines, the payroll worries — all of it seems to fade into quiet. You think, "This is what I've worked for my entire life."

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But as the hours pass, a strange emptiness creeps in. The phone doesn't ring like it used to. The inbox is silent. There's no meeting at 9 a.m., no one asking for your signature, no fires to put out.

You've reached the finish line — but there's no tape, no roar of the crowd. Just quiet.

The space between 'sold' and 'what's next'

Every entrepreneur imagines what life will feel like after selling their business for big bucks. Very few prepare for it.

The moment you close the deal, you move from constant urgency to complete stillness. That kind of silence can be disorienting for people who are used to burning the candle at both ends.

About Adviser Intel

The author of this article is a participant in Kiplinger's Adviser Intel program, a curated network of trusted financial professionals who share expert insights on wealth building and preservation. Contributors, including fiduciary financial planners, wealth managers, CEOs and attorneys, provide actionable advice about retirement planning, estate planning, tax strategies and more. Experts are invited to contribute and do not pay to be included, so you can trust their advice is honest and valuable.

It's not the money that challenges you — it's the absence of motion. For years, your identity has been tied to building, managing, deciding and creating value for your customers or clients. When that purpose evaporates overnight, it leaves a gap no portfolio can fill.

So before you start investing, building or buying again, give yourself a little time to simply exist without a business attached to your name. It's harder than it sounds — but that quiet is where clarity starts.

Take a beat before you build again

Many former business owners rush to fill the void. They start another company, buy property or invest in a friend's idea — anything to feel that forward momentum again.

But jumping too quickly can blur the line between excitement and escape.

Take 90 days. Maybe six months. Wake up without a calendar full of calls. Relearn what you enjoy doing when no one's watching the clock.

Ask yourself:

What parts of running the business truly energized me?
What parts drained me?
Who am I when there's nothing left to prove?

You'll be surprised by how much clarity comes from doing nothing in a world that constantly tells you to do more.

Money isn't a goal — it's a tool

The number in your bank account is just that — a number. It can give you freedom, or it can give you anxiety, depending on what you do next.

Rather than focusing on investments right away, focus on structure.

A simple framework:

Security. Pay off what needs paying off. Keep enough liquidity that you can sleep at night
Lifestyle. Decide what comfort and joy look like now — not extravagance, just design
Growth. Create a plan for investing that doesn't depend on luck or impulse
Legacy. Think about the impact you want your money to have long after you're gone

Money has power. But power without purpose tends to drift.

Beware the 'second startup trap'

Most entrepreneurs don't retire — they reinvent. It's in their nature. The problem is, not every next move deserves your energy.

If you feel the urge to start something new, that's natural. But pause long enough to make sure it's not just nostalgia for the chase.

Ask yourself a few grounding questions:

Am I building this because I believe in it, or because I miss being busy?
Would I still do it if it made half as much money?
Does it make my life bigger — or just louder?

You earned the right to be selective. Exercise it.

Redefine what 'work' means to you

When the title on your business card disappears, you have a chance to rewrite your story.

You might mentor someone just starting out. You might invest in an idea that excites you but doesn't consume you. You might take on projects that pay nothing but matter deeply.

Fulfillment doesn't always look like another company. Sometimes it looks like peace, contribution or curiosity.

Purpose over profit

The happiest people I know who've sold their businesses didn't chase the next big score. They chased meaning.

They created scholarships. They funded community projects. They showed up for family events they used to miss. They used their money to build a life that was intentional, purposeful and meaningful.

As Viktor Frankl once wrote: "Life is never made unbearable by circumstances, but only by lack of meaning and purpose."

Purpose doesn't come from the sale — it comes from what you decide to do after it.

The bottom line

Selling your business for $5 million is an extraordinary milestone. But don't let that number define you.

You didn't just sell a company — you sold the story you've been living. Now you get to write another one.

There's no right answer for what to do next. The only mistake is to believe the story ends here.

Take a breath. Look around. Then decide what's truly worth your time, your energy and your heart.

Because this next chapter — the one without payroll, deadlines or investor meetings — might just be the best one yet.

Disclaimer

This article was written by and presents the views of our contributing adviser, not the Kiplinger editorial staff. You can check adviser records with the SEC or with FINRA.

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Dennis D. Coughlin, CFP, AIF, co-founded CG Capital with Christopher C. Giambrone in 1999. He has been in practice since 1996 and works with individuals nearing retirement and those whom have already retired. Proud of his humble upbringing, Dennis shares his advice with the same core principles that he was raised with. When not in the office, you will find him with his family enjoying the outdoors.