Life After the Exit: Finding Purpose and Prosperity Beyond the Business
February 12, 2026
By Bo Wilkins
The post-exit period presents a paradox that catches many business owners off-guard. After spending years preparing for and executing the sale, the moment finally arrives. The wire transfer hits the account. The celebration happens. And then, often within just a few months, a profound question emerges: “Now what?”
According to Bo Wilkins, Managing Director at Oxford Financial Group, the hardest part of selling a business isn’t the transaction itself—it’s figuring out who you are without it. Many owners spend enormous energy on exit preparation and financial planning but almost no time on the psychological transition that follows.
The Identity Challenge
For most multi-unit restaurant or retail operators, the business isn’t just a source of income. It’s a core part of identity. The business shapes how they introduce themselves, defines much of their social network, provides daily structure, and gives life meaning and purpose.
When that’s suddenly gone, the loss can be disorienting. Waking up on a Tuesday morning with nowhere to be, no morning meeting to attend, no paperwork to review, no crisis demanding immediate attention—for some people this is initially liberating. For others, Bo says, especially those who’ve been operating businesses for decades, the novelty wears off quickly.
A common pattern emerges. The first month post-exit typically brings relief. The second and third months are usually positive—catching up on everything that got neglected during years of intense business focus. But around month four or five, restlessness often sets in. That’s when feelings of boredom, uselessness, or lack of purpose can surface. These are accomplished, successful people who suddenly feel lost and just don’t know what to do with themselves each day.
The owners who navigate this transition most successfully are those who started preparing for it years before the exit. Part of the multi-year planning horizon should involve developing an identity that isn’t solely tied to the business. Reconnecting with old hobbies, getting involved in community activities, building relationships unrelated to restaurants or retail—all of these create a foundation for post-exit life.
Those owners who gradually reduce operational involvement while increasing other activities in the years before a sale, find the transition becomes manageable rather than devastating.
Common Financial Mistakes
While psychological challenges often surprise owners, Bo says he sees financial mistakes follow predictable patterns.
The first major mistake is spending too much too fast. Receiving a large amount of liquid capital—more than has ever been available at once—can create a sense that the money is infinite. The dream house, vacation home, luxury vehicles, extravagant trips—these purchases can consume millions of dollars in surprisingly short order. Eighteen months later, the realization hits that a significant portion of the proceeds are gone without much to show for it.
A useful guideline Bo shares with his clients: don’t make any major financial decisions for at least six months after closing, ideally a year. Let the money sit. Allow time to adjust to the new reality. Then make decisions from a place of clarity rather than emotion.
The second major mistake Bo often sees is the opposite of the first: feeling guilty about having money and being afraid to spend any of it. This particularly affects owners who grew up without money and built businesses through frugality and hard work. They simply cannot give themselves permission to enjoy what they’ve earned.
Finding the balance—spending enough to enjoy life but not so much that it creates financial stress—requires intentional planning. This is where working with a wealth advisor becomes valuable. Professional guidance can model different scenarios: what’s safe to spend annually, what major purchases are affordable, how to structure things for tax efficiency and estate planning.
One effective strategy is capital allocation thinking. Some portion of proceeds should secure retirement through conservative investments that generate income and preserve capital. Some portion can be more aggressive with growth potential. And some portion should be explicitly designated as “enjoyment money”—guilt-free spending on things that have been deferred for years.
Bo explains to clients that when there’s explicit permission to spend a specific amount on discretionary purchases, those purchases become enjoyable rather than anxiety-inducing. There’s no background worry about financial irresponsibility because the spending is planned and sustainable.
Estate Planning Becomes Urgent
Before the sale, estate planning is somewhat theoretical. Wealth is tied up in illiquid business equity. Post-exit, with liquid assets, estate planning becomes urgent. If something happens to the owner, there are immediate tax consequences for heirs. This means creating or updating wills and trusts, thinking about gifting strategies, considering life insurance, and ensuring wealth will transfer according to intentions.
Beyond the mechanics of estate planning lies the bigger question of legacy. Bo will ask his clients what they want that money to accomplish – how do they want to be remembered? Some people create foundations or donor-advised funds. Others become deeply involved in causes they care about. Some focus on ensuring children and grandchildren are well provided for without losing motivation.
Bo often sees that the legacy conversation with owners even extends to the business itself, too. Even after selling, many owners still care about what happens to it. Do the new owners maintain the culture that was built? Are former employees treated well? Is product or service quality maintained?
At some point, Bo explains, letting go becomes necessary. After the sale, the business belongs to someone else. New owners will make different decisions. Some of those decisions may be disagreeable, but they’re no longer the seller’s call. The job becomes focusing on the next chapter rather than obsessing about what’s happening with what used to be theirs.
Staying Connected Versus Moving On
A frequent question Bo discusses with his clients is whether to stay involved in the industry post-exit. There’s no universal right answer—it all depends on exit motivations and future desires.
For owners who exited due to burnout, a complete break is often healthiest. If 80-hour weeks had become miserable, staying connected to that world doesn’t make sense. Moving on to find something energizing makes more sense.
For owners who still love the industry but were ready to step back from daily operations, there are ways to stay involved on different terms. Some become angel investors or consultants for other multi-unit operators. Some serve on industry association boards and help mentor the next generation of franchisees.
Private equity partnerships create their own version of this question. When equity is rolled and involvement continues as CEO or in another leadership role, there’s liquidity and reduced risk, but work continues. The question then becomes: when is the right time to exit from that role, and how should the relationship with PE partners be managed?
The Second Act
About 18 to 24 months post-exit, Bo often sees an interesting pattern emerges. Restlessness either evolves into contentment as people settle into retirement, or it transforms into hunger for a new challenge.
Many entrepreneurs find they cannot simply retire. They need to build something or pursue meaningful projects. Bo tells them this is perfectly fine—as long as decisions about new ventures are thoughtful rather than reactive.
The key is not rushing into anything. Starting a new business three months post-exit out of boredom often leads to regret in Bo’s experience. Taking time to figure out what this next chapter should actually look like is the wiser approach.
Some former owners start new businesses in completely different industries. Others get involved in real estate development or venture investing. Some pursue passion projects that would never have been financially viable but can now be done for fulfillment rather than profit.
Second acts should be about meaning, not just activity. The financial pressure is gone. This creates freedom to pursue what’s genuinely fulfilling rather than what’s merely profitable.
Family Relationship Dynamics
The post-exit period often creates unexpected pressure on family relationships.
For married couples, the challenge is suddenly spending significantly more time together. If a marriage has functioned with one partner working 70 hours weekly while the other has a separate life, what happens when both are home constantly? Some couples thrive with increased togetherness. Others discover they don’t actually have much in common anymore. Bo advises his clients that having professional support to discuss what life will look like post-exit, how time will be spent together, what individual goals are will help prevent considerable conflict.
For families with adult children, there’s often tension around wealth transfer. Adult children may have expectations about how much they’ll receive and when. Those expectations may not align with actual plans. Explicit conversations early are better than creating resentment later.
Situations where adult children were involved in the family business can be particularly complex. If they feel entitled to proceeds despite not being formal owners, difficult conversations become necessary. These family dynamics can severely damage relationships if not handled carefully.
Permission to Enjoy It
The most important message Bo has for owners entering post-exit life is simply this: it’s okay to enjoy it. The hard work has been done. Risks have paid off. Value has been created. This should be a rewarding new chapter.
It’s also important to understand that if the first year is difficult – feelings of being lost, some depression, boredom – that doesn’t mean a mistake was made. It means a major life transition is underway. That’s human and normal. Having grace with oneself, getting appropriate support, and trusting that adjustment will happen – all of these matter.
The money from selling a business can buy many things, but it cannot automatically provide purpose, identity, or fulfillment. Those must be built intentionally. Starting to think about them years before exit, rather than after, makes the transition dramatically easier.
The quality of life after the business may ultimately matter more than the business itself ever did. That makes the psychological preparation as important as the financial preparation. Both deserve serious attention and planning.
From all of his years of experience, Bo has seen that successful exits aren’t just measured by transaction value. They’re measured by whether the next chapter of life is genuinely fulfilling. With proper preparation – both financial and psychological – he has seen that outcome becomes much more likely.
This article is provided for informational and educational purposes only and should not be construed as personalized investment, legal, or tax advice. The views expressed reflect those of the author based on their experience and professional judgment. Past performance and experience do not guarantee future results. All examples are hypothetical and for illustrative purposes only.Please consult your financial advisor regarding your specific situation.
Oxford Financial Group, Ltd. (“Oxford”) is a Registered Investment Advisor (“RIA”) with the U.S. Securities and Exchange Commission (“SEC”) and is headquartered in Carmel, Indiana. Registration with the SEC does not imply a certain level of skill or training. Additional information about Oxford, including our Form ADV and Privacy Policy, is available upon request by calling 800.722.2289 or emailing [email protected]. OFG-2511-43
Written in collaboration with
Bo Wilkins
Bo Wilkins is Managing Director at Oxford Financial Group, Ltd™., where he works closely with colleagues and clients’ advisors to design innovative wealth transfer strategies for business owners and family offices. With over 30 years of experience in estate, legacy, and business succession planning, Bo is recognized as a published thought leader, frequent speaker and active board member in both professional and philanthropic organizations.
