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Before Your Sell: Crafting Your Post Sale Vision

NoteThis is the second part of an eight part series that addresses the key questions that you, as a business owner, need to really focus on as you begin to think about the sale of your business.  This series will give you actionable insights on assessing your readiness to sell, what you need to do to be prepared for the process and what real success will look like post sale.  Happy reading!


Selling your business is one of the most significant decisions you will make—one that impacts not only your financial future but also your personal and professional identity. Surprisingly, many business owners experience seller’s remorse after the sale. According to the Exit Planning Institute, 75% of business owners profoundly regret selling their businesses within a year. This statistic highlights the importance of crafting a clear and thoughtful vision for life after the sale.

A well-defined post-sale vision ensures that every decision made during the transaction process aligns with your long-term goals, helping you avoid regret and transition successfully. As experienced business advisors, we’ve guided countless business owners through this journey. Below, we outline four key areas to focus on when envisioning life after the sale, along with questions and insights to help you navigate each step.


Personal Goals: Finding Fulfillment Beyond the Business

For many, a business is more than a source of income—it’s a core part of their identity. Without a clear plan for personal fulfillment, the transition can feel disorienting. Understanding what excites and motivates you beyond the business is the first step in crafting a fulfilling post-sale lifestyle.

Key Questions to Consider:

  • What kind of lifestyle do I want to lead after selling my business? Will it focus on relaxation, travel, or pursuing new personal challenges?
  • What passions or hobbies have I neglected while running my business? Identify activities or projects—whether creative, social, or adventurous—that you’ve been postponing.
  • How do I want to grow as an individual? Consider how personal development, such as learning new skills or engaging with your community, might play a role in this next chapter.

By addressing these questions, you ensure that your decision to sell supports a life of purpose and satisfaction.


Professional Ambitions: Defining Your Role in the Next Chapter

Selling your business doesn’t mean stepping away from work entirely. Some business owners find purpose in staying connected to their industry, while others are eager to explore new ventures or entirely different paths.

Key Questions to Consider:

  • Do I want to maintain a connection to my business? Roles like consultant, board member, or advisor allow you to stay involved without the pressures of day-to-day operations.
  • Am I excited about starting something new? Selling one business can fund your next entrepreneurial venture. What industries or opportunities spark your interest?
  • What professional goals have I yet to achieve? Whether it’s pursuing advanced education or mentoring others, consider how this transition could expand your professional horizons.

Your answers to these questions can guide your business broker and advisors to structure a sale that accommodates your professional aspirations.


Financial Considerations: Building a Strategy for Long-Term Security

The proceeds from selling your business are not just a payday—they represent the foundation of your financial future. Proper planning ensures these resources align with your personal and professional goals.

Key Questions to Consider:

  • How much do I truly need to net from the sale? Assessing your financial needs is critical and often reveals gaps between expectations and reality.
  • What is my investment strategy for the sale proceeds? Whether it’s retirement planning, funding a new venture, or supporting family, a clear strategy ensures your wealth is preserved and grows.
  • Am I interested in leaving a legacy? Consider how charitable donations, trusts, or estate planning might help you support causes or loved ones in meaningful ways.

Engaging with a business advisor early ensures you approach these financial considerations with clarity and confidence.


Transition and Downtime: Preparing for Life After the Sale

Transitioning from a fast-paced entrepreneurial lifestyle to something slower can be challenging. Many former business owners struggle with the lack of structure and purpose they once had. Preparing emotionally and practically for this shift is vital.

Key Questions to Consider:

  • How will I adjust to a slower pace? Without the daily demands of running a business, how will you structure your time and maintain a sense of purpose?
  • What steps will I take to stay active and engaged? From travel to wellness goals or volunteer work, staying mentally and physically active can ease the transition.
  • What does “taking a break” mean to me? Whether it’s a sabbatical or simply scaling back commitments, define what recharging looks like for you.

Having a plan for this downtime can help you embrace the change rather than feel adrift.


Your Vision Defines Your Outcome

Selling a business is more than a financial transaction—it’s a pivotal life event. Success isn’t just about the sale price or terms but about how well the outcome aligns with your personal goals, professional aspirations, and financial needs.

Take the time to consider these questions deeply. The clarity you gain will guide your business broker and advisors to structure the sale in a way that supports your unique vision for the future.

To further ensure your financial readiness, consider calculating your Freedom Score. This comprehensive assessment will give you insight into how much you need to net from the sale to fund the next phase of your life.

Get My Freedom Score

Take our free assessment to discover your freedom point. Once you’re done, you’ll receive your Freedom Score Report, a comprehensive analysis of your financial readiness to enter the next phase of your life.

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