Selling your agency is a big deal. After years of hard work, you’ve reached a major milestone, both personally and professionally. But a big question looms: What comes next?
The transition from agency owner to “what’s next” isn’t just about financial planning or career pivots: it’s about redefining your identity, relationships, and lifestyle. This process can feel overwhelming, in part because there’s no “right” answer. But with intentional reflection and planning, this could become one of the most rewarding times of your life.
This article is your practical (and compassionate) guide to help you navigate life after selling your agency. Follow these steps to prepare for life after agency ownership:
- Reflect on your ideal future
- Plan for family and caregiving responsibilities
- Address health and aging considerations
- Refine (and redefine) your identity
- Revisit your living situation
- Create a financial plan for the long term
- Secure your legacy
- Protect your social and emotional well-being
Read on for details on each step. And if your exit is still years away, get my Control (and Maximize) Your Agency Exit on-demand training today to help you get there faster and more confidently.
1. Reflect on your ideal future
Before diving into the logistics, take time to envision your future. What do you want your life to look like? For years, your schedule and identity have revolved around running your agency. Now, you have the chance to start with a blank slate (or at least a semi-blank slate; the rest of your life is still there).
Ask yourself:
- What activities bring you joy and energy?
- Are there passions or hobbies you’ve neglected while running your agency?
- What relationships or experiences have taken a backseat?
- What have you been dreaming about doing once you’re “free” from your agency?
Consider your lifestyle goals:
- Do you want to travel more? What’s your taste in travel? Do you want to do several small trips plus an annual $10,000 trip? Or do you prefer $20,000 luxury trips every quarter?
- How much income will you need to support your desired lifestyle?
- Would you prefer a simple, slower life—or an adventurous, fast-paced one?
- How might your goals change over time? People often look forward to playing golf every day… but it eventually gets old.
These questions can help you start to outline your priorities and clarify what “success” looks like for this next chapter.
Facing writer’s block? Consider writing an Advance Retrospective about your ideal future; the free tool gives you a mix of structure and flexibility. And if you’re weighing two very different options, write an Advance Retrospective about both options. In my experience, you’ll likely enjoy writing one of them a lot more—which is usually a sign about which one to explore further.
2. Plan for family and caregiving responsibilities
Your family situation impacts your post-sale life, too. The money and freedom from your exit create new opportunities, but also require some new juggling.
- Kids or no kids: If you have children, their ages and needs are key considerations. Are they still young and living at home? Are you paying for college or other major expenses? Do they have special needs that will require ongoing care? Is there a shared custody situation? If so, plan how your financial windfall will align with these responsibilities.
- Caregiving responsibilities: Are you helping aging parents or other relatives? Selling your agency might allow you more time to provide care, but it may also require rethinking your living situation or financial commitments. If you have siblings and you’re fully retired, they may expect you to do everything now.
- Partner or spouse work: If you’re married or in another long-term relationship, is your partner still working? Talk about your and their expectations. Will they keep working? Will they stop working after reaching certain thresholds? There’s a lot to discuss; if you don’t communicate, you risk creating resentment.
- Dating or not: If you’re single and dating (or you want to date), that might shift how you spend your future time versus being in a relationship. If you’re single but don’t like where you live, moving might be a change of pace (but not an automatic solution; the “geographical cure” is mostly a myth).
These personal responsibilities aren’t just logistical—they’re emotional, too. Be realistic about how caregiving or family priorities will impact your time and energy in this new phase of life. Want to do a test run before you sell the agency? Consider taking a sabbatical to get a taste of what it’s like to be away from work.
3. Address health and aging considerations
Health impacts your post-sale life, too. If you’re in your 30s or 40s, you might have decades ahead to explore new ventures or hobbies. If you’re closer to retirement age, health challenges might impact your decisions.
Here are key questions to consider:
- Health insurance: If you’re under 65 and not yet eligible for U.S. Medicare, how will you cover health insurance costs? Self-pay premiums are expensive. Does your spouse have access to group insurance through their work? Would you work as a part-time employee if it included health insurance? Would you work as a fractional executive to cover healthcare expenses?
- Healthcare arbitrage: Would you consider relocating overseas to take advantage of lower healthcare costs? For example, countries like Portugal or Mexico are known for affordable, high-quality healthcare for expats.
- Physical wellness: Are there any long-neglected health issues you want to address now that you have more time and resources?
Coupled with time, your health is your least renewable resource. Now that you don’t have the “I don’t have time; I’m running the business” excuse, make a plan to prioritize your health in your post-agency life.
4. Refine (and redefine) your identity
Consider how you might redefine who you are. For many agency owners, their identity is tied to their role as CEO. After stepping away, it’s natural to feel a sense of loss or uncertainty about who you are without your business.
In the live edition of my exit-prep training, I surveyed participants about what they wanted do after their exit. Here’s how they responded:
- Start a new venture: About 50% of agency owners wanted to start a new business after exiting. For some, it was a passion project. For others, it was a career change.
- Work part-time: Almost 20% of agency owners wanted a part-time role, such as consulting or coaching others.
- Fully retire: One in six wanted a full retirement.
- Not sure yet: A small portion said they didn’t know or weren’t sure about their post-exit goals. If this is you, that’s okay; take time to explore your options.
- Work for the acquirer: Notably, no one said they wanted to work for the acquirer. But the reality is that you might need to stay for 2-3 years to secure earnout payments. You can negotiate a ramp-down on your work; for instance, you might be full time for a year, half-time in the second year, and on-call in the third year.
Some agency owners report they want to start another agency. Others use their new chapter to try something new. If you want to work, hiring a life coach or career coach can help you navigate options.
As you explore your new identity, reflect on how your social circle might shift. Some sellers find it challenging to connect with friends or acquaintances who are still working full-time. You may need to seek out new communities or activities that align with this phase of life.
Speaking of communities, I recently interviewed Carl Smith at the Bureau of Digital about his post-agency life. He bought the Bureau and wound down his agency. Now, he helps 1,000+ agency leaders create better firms, through community and events.
5. Revisit your living situation
Selling your agency creates opportunities to change where and how you live. Ask yourself:
- Is your house paid off? If not, will you use proceeds from the sale to pay it off? Do you want to downsize or buy a bigger house?
- Relocation: Do you want to move to a warmer or cooler climate? Is it time to buy the house at the beach, on a lake, or in the mountains that you’ve always wanted? Do you want to move closer to (or farther from) family? Consider both lifestyle and financial factors—like property taxes, insurance, cost of living, politics, healthcare facilities, and overall quality of life.
- Financing: If you’ve gotten a mortgage while owning the agency, you know it’s painful to get a mortgage while self-employed. Keep in mind that it will be harder to secure future financing if you don’t have a steady income.
Your home is more than just a financial asset; it’s impacts your day-to-day lifestyle. Take time to evaluate how your housing aligns with your future goals, including whether you’ll need more or less space.
6. Create a financial plan for the long term
The proceeds from selling your agency can create significant financial freedom—but only if you plan carefully.
- For example, a $10 million exit could generate approximately $400,000 annually at a conservative 4% withdrawal rate.
- However, a $3 million exit provides $120,000 annually; unless you have significant other income, this is likely a significant reduction from your current income as an agency owner.
Some of your exit payments might be contingent, too. Say you received $4 million down, plus an earnout of an additional $2 million in the second year and a final $2 million in the third year. You might not receive the second or third payments. Don’t spend money you haven’t received; earnouts are never guaranteed.
Work with a financial planner to:
- Budget for your desired lifestyle, including healthcare expenses.
- Plan for travel, hobbies, or other major expenses.
- Balance immediate enjoyment with long-term sustainability.
Proceed carefully if you don’t currently have a financial planner or want to change to someone new.
- If they’re in the U.S., I prefer fee-only CFPs who act in a fiduciary capacity. This eliminates the conflict of interest that comes when someone is receiving commissions and has an incentive to trade frequently on your account or to recommend expensive financial instruments you don’t need.
- Check disciplinary records at FINRA BrokerCheck, the SEC IAPD, and state authorities.
- Ask around your network for referrals. If you need to search from scratch, consider something like the XY Planning Network; that’s how I found my previous CFP (before he retired to focus on his SaaS product).
- They may charge a retainer plus a fee for assets under management (AUM). The AUM fee is negotiable; the higher your balance, the lower the percentage.
Also, consider the mindset shift from accumulation to spending. Many former business owners struggle with this transition—delaying retirement or avoiding large expenses because they’re used to building wealth rather than enjoying it.
A friend kept delaying his retirement from a job he’d grown to hate—until his financial planner pointed out that each extra year added almost nothing to his future income. He gave notice and retired… but didn’t tell most people right away, since he knew they’d start burying him in family and volunteer responsibilities.
7. Secure your legacy
For some, selling an agency is an opportunity to think about the legacy they want to leave behind. While this isn’t a priority for everyone, your exit creates a meaningful way to shape your future.
Some legacy-building options include:
- Philanthropy: Support causes you’re passionate about, through finances and time. You might enjoy serving on the board of an organization you support. If you want your name to live on, you might choose to create a named endowment.
- Teaching or mentoring: Share your expertise with agency leaders or entrepreneurs who are earlier in their careers. You can also do guest lecturing or even become an adjunct instructor.
- Writing: Capture your experiences in a book, blog, or other format. If you want to publish traditionally, you may need to secure an agent. But with self-publishing, there’s no barrier to getting started. If you want to write non-fiction, check out The Scribe Method and Write Useful Books. If you want to write fiction, that’s beyond my expertise—but look for adult education programs at the community college or something like the Redbud Writing Project in NC.
- Building something new: Now might be the time to launch a nonprofit, foundation, or personal project. If you want to start a non-profit, check out your state’s association of non-profits for resources. The NC group was a client at a past agency; they have a guide to starting a non-profit… which starts by advising to not do it.
Your legacy doesn’t have to be grand or public, although that’s certainly an option. It’s about creating something meaningful to you.
8. Protect your social and emotional well-being
Selling your agency is as much an emotional transition as a financial one. After years of high-stakes decision-making and constant activity, the slower pace may feel disorienting. You may also notice that people don’t call you for advice or help; it can sting to realize you’re more replaceable than you might have felt when you ran your agency.
Some strategies to support your emotional well-being include:
- Staying socially active by joining groups, clubs, or professional networks.
- Exploring new hobbies or interests to keep your mind engaged.
- Working with a coach or therapist to process the transition and set goals for the future.
There are books and courses to help, too. I recently started reading Learning to Love Midlife: 12 Reasons Why Life Gets Better with Age by Chip Conley.
Conclusion: Your next chapter awaits
Life after selling your agency is full of possibility, but it requires thoughtful planning. You aren’t a billionaire but you have options beyond 95-99% of the general population.
From redefining your identity to managing finances, health, and relationships, this next phase is about creating a life that excites and fulfills you.
Remember, there’s no single “right” path after your agency exit—only the one that aligns with your values, priorities, and dreams. Take time to reflect, explore, and plan. Your best years may be just ahead.
What will your next chapter hold? Only you can decide—but the possibilities are endless. Congratulations!
Question: What’s your ideal life after you sell your agency?
