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When entrepreneurs think about selling their business, they typically focus on the deal itself – valuations, terms, negotiations. But there’s a crucial conversation that rarely happens: What comes next for you personally?
Carolyn Nolan, CEO and Private Wealth Advisor at TNG Private Wealth, has spent over 20 years helping entrepreneurs navigate the often-overlooked personal and financial transitions that come with a business exit. Her perspective? The money is actually the easy part.
The Question No One Asks
“The big elephant in the room is why the heck are we doing all of this?” Carolyn asks. While financial windfalls are certainly part of the motivation, there’s usually a deeper pull, something entrepreneurs have been dreaming about but haven’t had time to pursue.
But here’s the problem: entrepreneurs don’t know how to take vacations.
Think about it. If you can’t unplug for a week, what happens when it becomes a permanent vacation? For most entrepreneurs, sitting on a beach lasts about 24 hours before they start getting twitchy.
The Framework That Changes Everything
Carolyn’s approach flips the traditional wealth management conversation on its head. Instead of starting with “What can you do with all this money?” she asks a more fundamental question:
“What do you unapologetically want?”
She’s so passionate about this concept that she literally has it tattooed on her arm. It’s about getting clear on what excites you, what scares you, who you want to spend time with, and what you want to do before everyone starts telling you what you should do with your windfall.
“Forget all of this, put it aside and let’s first just talk about what excites you, what scares the crap out of you, what are we trying to do here?” she explains. “Not with the money, but with your life.”
The Mistakes That Blindside Entrepreneurs
After years of collecting stories from clients across different stages of life, Carolyn has seen patterns emerge. The mistakes typically fall into two extremes:
The Spenders
Some entrepreneurs start “pissing it away really fast,” as Carolyn puts it bluntly. The most common culprits? Real estate and excessive gifting.
The critical error here is not understanding tax implications. “Your net worth is not net of what you’re gonna pay in taxes,” Carolyn emphasizes. You might see millions in your bank account, but half could be owed to the IRS.
The Frozen
On the opposite end, some entrepreneurs spend nothing. They feel guilty, undeserving, and paralyzed by their sudden wealth. The money that should bring freedom instead becomes a source of anxiety.
Making Your Financial Life Boring (So Your Real Life Can Be Exciting)
Carolyn’s philosophy is simple: structure your finances so you never have to think about them, freeing you to focus on actually living.
Her recommended approach for substantial exits:
The Workhorse Strategy: This is your foundation, not sexy, but reliable. It’s designed to work through market crashes, tax increases, and unexpected life events. The goal is to ensure you always have access to money when you need it, regardless of market conditions.
The Racehorse Strategy: Once your essentials are covered, this is where you can take calculated risks with more speculative investments, knowing that if things go south, your lifestyle isn’t threatened.
The key insight? What many people call “discretionary expenses” aren’t actually discretionary. If you golf every day, that membership isn’t optional, it’s part of your lifestyle. Factor that in as a fixed expense.
The Patterns of Post-Exit Happiness
Through observing countless clients, Carolyn has identified what makes people thrive after an exit:
Structure with flexibility: The happiest clients maintain morning and evening routines while leaving their days open. It grounds them without making them feel constrained.
Selective engagement: Spending time with people who energize you, avoiding obligations that drain you. Post-exit, you finally have the freedom to choose.
Continued learning: Many clients audit college classes, experiencing the joy of learning without the pressure of grades or papers.
Purposeful challenges: Even on vacation, entrepreneurs often benefit from having “something hard” to work on. It’s not about deserving relaxation; it’s about what brings genuine enjoyment.
The Multi-Generational Conversation
When it comes to passing wealth to the next generation, there’s no one-size-fits-all answer. Carolyn works with clients to think through critical questions:
- Do you want them to have access now or later?
- Should there be boundaries or full access?
- How do you protect assets from future divorces?
- How do you allow enjoyment without creating entitlement?
The shift Carolyn sees in modern wealth transfer is significant: “People want to be able to see their kids enjoy it now and not just wait for them to die.”
Don’t Wait for “Later”
When asked what she’d tell her younger self, Carolyn’s advice is immediate: “Don’t wait till later.”
Find ways to enjoy life now. Plan the big experiences you want to have. And critically, identify the people who can do the cool things with you because major transitions can bring unexpected loneliness.
The Bottom Line
An exit isn’t just a financial transaction, it’s a life transition. The entrepreneurs who thrive are the ones who do the internal work before the deal closes:
- Getting clear on what they actually want (not what they “should” want)
- Understanding the real numbers after taxes
- Creating structure that allows for both stability and freedom
- Building or maintaining relationships that matter
- Finding purpose beyond the business
As Carolyn puts it: “With the right advisor, this stuff can be really fun.”
But it starts with asking yourself the uncomfortable questions before you’re forced to answer them with a sudden windfall in your bank account and no plan for what comes next.
