Reinventing Yourself


Twenty years ago, the recognized path to success was to graduate college, get a good job with a good company and retire at 65. For successful business owners, most of whom bucked that trend by starting or acquiring a business, saw their success come from building that business. As owners approach age 65, they may begin to define success differently. It could include the successful sale their business, it could include lazy days at a beach home, or more often than not, it includes some kind of reinvention. But reinvention is easier said than done. Some of the unexpected challenges include:

  •  Deep identification with your role as a business owner and all of what comes with that.
  • A spouse who has different ideas about what the next chapter should look like, when it should start and what it will include.
  • Pre-conceived notions of what is or is not possible for you in the next chapter of your life.
  • Trouble balancing reinvention with family expectations, business priorities, and travel.
  • Too busy running the business to sit down with an expert and talk about the future.

Some Typical Questions

Here are some questions we hear as we work with business owners on their ‘reinvention’. Let us know what questions you have.

I am getting ready to retire. How do I encourage my spouse to consider their own “next chapter”?

You are wise to encourage your spouse to proactively plan for their own ‘next chapter’. Many couples don’t. Initiating conversations about their priorities and expectations in retirement will give you a sense of their interests and provide you an opportunity to share your priorities as well. We recommend sitting down with a financial advisor as well, so you can jointly review funding the next chapter. We have several financial advisors we recommend. One of them, Stearns Financial Group (SFG), has a financial independence roadmap that initiates future visioning discussions. By opening up regular communications, and focusing on what matters most to each of you, you can begin to map out a blended life pattern that nurtures and supports each of you.

It’s important to note that many people find they need a facilitator to have a productive discussion, either because their lives are too busy or because either husband or wife already has a set view of the next chapter and how it should play out. Consider hiring a professional. We can recommend a coach who targets your specific needs.

I think I want to volunteer more in my next chapter, but I’ve had some hit or miss volunteer opportunities with non-profits. My time is limited and I have some causes I’m really passionate about, but it seems like the entities I care about have poor volunteer practices. What should I think about for the best fit?

Thank you for supporting non-profits. If, as part of your "reinvention", your prime objective is to provide support for the causes you are passionate about, you may find it more rewarding to simply donate money, especially if you can designate that donation toward a particular need, such as updating a computer lab or hiring a facilitator to assist with board development. Depending on your goals, your financial advisor or your local Community Foundation can help you plan the best way to channel your particular philanthropic interests.

If you truly enjoy being hands on, talk to the director or volunteer coordinator about the kind of help they need and the kind of volunteer work you most want to do. Often you can carve out a role for yourself if you are clear on how to marry their important needs with your skills and interests. You have to be willing to truly listen for what the non-profit most needs, and you have to be willing to be clear on what your highest and best use would be. If there is not a match, move on. There are often several organizations in a region that serve a particular non-profit need. You may need to search a little wider to find one that also has a good match between their needs and your best use. In Greensboro, The Volunteer Center or the Guilford NonProfit Consortium might offer suggestions.

I am really struggling to stay engaged and not be bored after retirement. What advice do you have about figuring out what to do?

You are in the first generation that will likely be healthy for 15+ years in retirement. The blessing is a longer and better quality of life. The curse is what to do with all of that time! Harvard School of Public Health found that heart attacks/strokes are 40% higher in retirees, and the rates were highest in the first year of retirement. It is often triggered by loss of identity, community connections, lack of meaning, and changing life patterns. The shift can be very disorienting and stressful. AARP has created an on-line program called ‘Life Re-imagined’ that provides resources for retirees to re-imagine their life in retirement. also provides resources for those interested in a second (3rd or 20th) career. founder Marc Freedman, and others, have books out on the topic.

At The Leadership & Legacy Group, we work with business owners and CEO’s, who have spent the better part of their career driving business results. Our model seeks to help these driven professionals make a successful transition into ‘what’s next’. Clients work 1-1 with a CEO Succession coach through a proprietary model to discern their passions, clarify their favorite strengths, and identify their most important lifestyle priorities. The process uncovers what ‘reinvention’ will bring deep meaning, personal engagement and fulfillment. We recommend starting this process 1-2 years in advance of your proposed reinvention time.

Expert Abby Donnelly is the Founder of The Leadership & Legacy Group. LLG helps business owners recognize and proactively navigate the inevitable stress and uncertainty that comes with succession planning and exit and enables them to create a powerful and rewarding future. It’s Your Time.

photo by krosseel