B.D. Dalton II, Lazy Overachiever, deal-maker, author and podcast host of Grow Sell and Retire, Director at Rockfine Group.
Every year, I journey to the ancient Tuscan town of Cortona, where I meet with America’s top independent brokerage leaders to discuss wealth, longevity and what true success looks like in the modern age.
Sitting in centuries-old villas overlooking rolling vineyards, our discussions often center around a crucial truth: The most successful business owners never truly retire; they rewire.
Plan Your Next Chapter Early
The traditional model of “sell up and retire to golf” is as obsolete as a fax machine. One leader, who manages over $3 billion in assets, shared how his most successful clients are those who sell their businesses but stay actively engaged in the business community.
This is the new reality for successful business owners. I’ve watched countless entrepreneurs focus entirely on maximizing their sale price while ignoring what comes next.
They build their exit team—the broker, financial advisor, accountant and lawyer—but forget to build their next chapter team. The result? They achieve their financial goals but miss their fulfillment goals.
Building Your Post-Sale Life
Here’s what I find most successful transitions have in common:
• They start “test driving” their post-sale life at least two years before exit.
• They build a portfolio of interests and opportunities before the sale.
• They maintain their business network while expanding into new areas.
• They balance commercial activities with philanthropic work.
• They focus on health and continuous learning.
Think of it like upgrading your operating system rather than shutting down the computer. You’re not stopping work; you’re upgrading how you work. One client recently told me, “I now take six weeks of holiday a year instead of two, but I’m making more impact than ever through my advisory roles.”
The health aspect cannot be overlooked. During our discussions in Italy, we often return to this crucial point. I’ve watched too many business owners treat their exit like a finish line rather than a starting point. They stopped networking, lost their purpose and their health suffered.
The most successful transitions involve staying physically active, mentally challenged and socially engaged.
Turning Your Exit Into An Opportunity For Greater Impact
One of our regular Cortona attendees, after selling his technology company, took three months to travel with his family. But he also used that time to read extensively about areas that interested him: sustainability, artificial intelligence and education. Today, he sits on four boards, has invested in six startups and mentors young entrepreneurs.
Based on his and other examples, I see the key to a successful transition lies in preparation and mindset. Many business owners struggle after selling their business not because of financial issues but because they lose their sense of purpose. That’s why it’s important for owners to start planning their next chapter well before the sale.
Your business acumen and experience are valuable assets that shouldn’t be left on the shelf. The key is to leverage them in a way that gives you more freedom while keeping you engaged. This is a new chapter where you have more freedom to choose your projects and commitments.
But as already outlined, your transition requires careful planning. What percentage of time do you want to spend on paid work versus philanthropy? How many boards would you like to sit on? What skills would you need to develop to make this happen? These questions should be addressed while you’re still running your business.
Another crucial aspect is maintaining and expanding your network. Many business owners underestimate how much of their network is tied to their current role. That’s why, for your next chapter, building new connections in areas that interest you is vital. This might mean joining different business organizations, attending industry events outside your current sector or getting involved with charitable causes that align with your values.
In expanding on how your physical and mental health becomes even more important after a business sale, you should also plan on how you will establish healthy routines after the transition. This includes regular exercise, continuous learning and maintaining social connections. Many successful business owners take up new sports or hobbies, learn new languages or pursue long-held interests they never had time for while running their business.
Thrive In Your Next Chapter
Remember, wealth without purpose is like a Ferrari without fuel: impressive but going nowhere. The goal isn’t to stop working; it’s to work differently. Create a life where you can take a month off for travel, then spend a week mentoring startups, followed by board meetings and family time.
As our Cortona discussions consistently reveal, the most fulfilled business owners are those who see their exit not as a final destination but as a gateway to new opportunities. They’re the ones who maintain their business networks, develop new skills and find ways to make an impact beyond their original business.
Your business sale isn’t the end of your story; it’s just the beginning of a new chapter. Stay engaged, continue to learn and maintain your health while enjoying more freedom to choose how and when you work.
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