Thought Leadership

December 20, 2023

You've Sold Your Business. Now What?

You've spent years building and nurturing a successful company, and when the time finally came to move on and sell your business, you probably had mixed feelings.

R360 Staff

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You’ve spent years building and nurturing a successful company, and when the time finally came to move on and sell your business, you probably had mixed feelings.

Now that the sale has closed, what comes next? “This is one of the most common questions business owners ask,” says R360 Managing Partner Barbara Goodstein. “There is the excitement that you’ve accomplished something major, but there is also the anxiety associated with the unknown. Selling a business can be a little deflating.”

This post-sale period is a crucial time for personal reflection and strategic planning as you prepare to navigate the next phase of your life. Now that you’ve sold your business, it’s time to explore some key considerations and steps you can take to make a smooth and successful transition.

Celebrate Your Achievements

“Take a moment to catch your breath, reflect on your journey, and celebrate your accomplishments,” Goodstein says. Acknowledge the hard work, challenges overcome, and milestones achieved during your time as a business owner. Celebrating what you have achieved creates a positive atmosphere around the transition.

Prioritize Financial Planning

Evaluate your financial situation post-sale and work closely with your financial advisors to develop a comprehensive plan that aligns with your short-term and long-term goals:

  • Formulate a strategy for incorporating the proceeds from the sale of your business into your overall financial plan.
  • If you were primarily living off the salary and the profits from your business, you’ll need to establish an investment-based monthly income stream.
  • If you didn’t do this pre-sale, now is the time to understand the unique tax implications of the sale and consider strategies for minimizing your tax liabilities.
  • Revisit your estate plan. Update designations, including guardian designations, trusts, designated trustees, healthcare proxies, powers of attorney, and will.
  • Think about your legacy. If you aspire to philanthropy, make a plan for charitable giving. Consider options like direct gifts, donor-advised funds, family foundations, or charitable trusts to maximize impact and minimize taxes.
  • Hold regular family meetings. If you don’t already, get together as a family at least quarterly to discuss financial issues and any concerns. 

Define Your Purpose

Now that you’ve sold your business and solidified your financial plan, take some time to carefully consider what you want to do with your time and energy in the next phase of your life. Whether starting a new venture, pursuing personal passions, or taking a well-deserved break, having a clear sense of purpose will guide your decisions and actions. “Sometimes our identities get wrapped up in our work — we become our businesses. Selling a business can cause a bit of an identity crisis,” says Goodstein. “Just remember to look forward and think about things to come not the things that are past.”

Stay Involved (If Desired):

If you haven’t sold your business yet, but are considering it, also think about staying involved in the business in an advisory role. This can help ensure a smooth transition for the new owners and existing employees while allowing you to contribute your expertise without the day-to-day responsibilities.

Explore New Opportunities

“Post-sale is an excellent time to explore new opportunities and interests,” Goodstein says. “This might involve starting a new venture, investing in other businesses, or taking up a worthy cause. Embrace the freedom to pursue endeavors that bring you fulfillment and joy.” If you’re not sure where to start, try making a list of everything that sounds interesting. Go wide and then you can narrow in on things that really appeal to you.

Take Care of Your Personal Growth and Development

Now is a perfect time to invest in your personal growth, something you may have put off while you were running your business. Attend workshops and seminars or pursue further education that aligns with your interests. You’ll be enhancing your skill set and opening yourself up to new perspectives and possibilities for the future.

Maintain a Healthy Work-Life Balance:

Avoid the temptation to immediately jump into another demanding venture. Give yourself the space and time to recharge and strike a healthy work-life balance. Doing so can significantly contribute to your overall well-being and set the stage for sustainable success in your future endeavors.

Build a Support System

Surround yourself with a supportive network of friends, family, and mentors. Share your thoughts and concerns with trusted individuals who can offer valuable insights and guidance as you navigate this transitional period.

Reflect on Lessons Learned

Identify both successes and challenges you’ve faced along the way. Consider how these experiences can shape your future decisions. “This introspection can be a powerful tool for personal and professional growth,” says Goodstein.

Embrace Change

Sometimes embracing change can be more difficult than it sounds. It’s easy to get lost in the past and think about all the good times spent building the business. But adaptability is critical to navigating this period successfully. Maintain an open mind and be willing to explore new opportunities and possibilities that may arise.


Moving on from your business can be as disconcerting as it is exhilarating. But by carefully considering your next steps and taking intentional actions, you can ensure a successful transition to the next phase of your life, brimming with new opportunities and personal fulfillment.

Disclosure: R360 is not an investment adviser. Information provided within is for educational purposes only and should not be construed, nor is intended to be, investment advice or a recommendation to invest in any types of securities. R360’s views are subject to change at any point without notice. No investment decision should be made based solely on the content herein and only a financial professional should be engaged for providing investment advice and recommendations. Past performance is not an indication of future returns.

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