A multi-step process for clarifying your Retirement Strategy

Consider, 75% of business owners were dissatisfied selling their business after finalizing the deal, or expressed seller’s remorse, according to the Exit Planning Institute’s Readiness Survey.

After Business Plan

Based on my experience I suspect retirees that arrive at their retirement date, plus one day, without planning for “the next chapter” may suffer similar issues.

There are 5 steps we use to frame, clarify, and quantify retirement strategies so you can avoid being in the remorseful cohort and pursue your vision.


Vision planning processes for businesses are well known and frequently produced. For retirees and post-sale business owners, less frequently to just not executed effectively, as the statistic above suggests.

Stephen CoveyClarifying your vision. In a perfect world of retirement, or the next chapter, what does it look like? What do you do each day, what do you look forward to, do you have a bucket list, what does your spouse want, what is your relationship like with your family or friends, what impact do you want to make, are but a few considerations. If you were to roll the clock forward 5,10,20 years in the future and look back what did you do. What do you want to be remembered for? Consider Stephen Covey’s advice to get started on your vision.


Based on your context, which is what matters to you, what do you want, in detail. What do you have that will fund the pursuit of what you want? What is the source of that funding and how durable is it? How long till you embark on the next chapter, what are your gaps? If there are gaps what is your strategy to fill those gaps? Is what you want aligned with what your spouse wants, where does that coincide, where does it diverge, how do you compromise, in what order do you want to pursue your goals and who sets those priorities?

I like to think of this human impulse towards order as a kind of window frame: It helps us to make sense of what we are looking at, but our attention must always be on what’s on the other side of the window, not the frames themselves, which after all tend to exclude more of the total vista than they include. From Simeon Dreyfuss on framing


Get specific. There are 8 categories that come to mind. We’ll deep dive into each one in other posts but for now. Vivid Vision, Values, Goals, Relationships, Assets, Advisors, Process and Interests. Make a page for each, or schedule some time with your loved ones, ask them what their vivid vision looks like and record it on your phone. You might be surprised.


If it is important measure it. Actually track your progress, did you do what you set down as a goal. Clarify what looks like success to you and use SMART goals to keep score. Look at what you said was important to you and your family specifically. Establish a system, prioritize, schedule, and execute. You must execute and successful execution momentum matters. Simple, is it done or not done, no in between, no excuses.

Stress testing

Stress testing, commonly used by the Ultra Wealthy(those with $500 million net worth or more) can help you make sure you have another set of eyes on your plan or strategy to ensure you aren’t making any serious mistakes with respect to your wealth management process. It also provides a process to make sure you aren’t overlooking risk management, an opportunity or strategy. The stress test may identify simple errors from miscommunication from your planning team or just a rethink and reorientation on what’s important to you and your family. Systematic periodic stress testing can assess how your strategy may perform in different scenarios. It may be there is a better solution currently that was just not available in the past. It makes sense to put your plan through its paces periodically in a formal process.

Next steps

Clarifying you vision, framing, quantifying, measuring and stress testing are steps you can take yourself. After all that you have accomplished you deserve a Wealth Management Operating System that helps you pursue your vision of success in the next phase of your life. Commitment and execution are critical ingredients for the 5 step system to be productive. We will explore in depth each of the steps in additional blog posts.

It can be overwhelming at times if you have not gone through this process before. If you prefer another set of eyes to help you with designing and implementing your strategy for achieving your vision for your “next chapter” schedule a call.