How to avoid Business Owner Seller Remorse and an Unhappy Retirement

Being a business owner can be all-consuming with no time to think about life-after-business.

And yet, when you exit the business you find those 60 hours weeks are now left with…what exactly? Those highs and lows you get from the business are replaced with golf and…

It’s said that people retire and go through the five of seven stages of grief, their lives seem over. This “seller’s remorse” covers two situations.

One where the business owner is about to sell their business but, when forced to think about retirement, changes their mind, cancels the sale (even if at a high price and good terms), and takes the business off the market.

I’ve had direct experience of this. As an M&A Advisor, I presented a good offer to the two owners. Forced to consider the offer, the owners changed their mind and decided that one could keep working while the other retired. They withdrew the business from sale. Frustrating and embarrassing for them and the prospective buyer.

The other situation is where they sell the business and suffer real dissatisfaction for several reasons including:
– not being sure what they’ll do in retirement
– believe they were underpaid
– sold it at the wrong time in the business cycle.

Surveys of business owners show that 75% of business owners become dissatisfied with the result post-exit.
(“State of Owner Readiness Survey” report, Exit Planning Institue (EPI), 2013).

They sell their business and then are disappointed with their life thereafter even if they received a great price and terms.

This is a well-recognised issue with selling businesses and one of the reasons why the exit planning approach was developed 30 years ago. Indeed, “the Original” of exit planning Peter Christman once said,

“figuring out what to do after you exit, is the most widely neglected of the three [tasks, the other two being business readiness and personal financial planning]. It stands to reason; we spend years thinking about and working toward our professional goals. Few of us stop to consider anything beyond their attainment. And yet the failure to address this third pillar can delay and complicate the exit planning process, causing people to fall short of their goals and objectives.”

(What will you put on your business card after you’ve exited your business? and other tough questions regarding the next phase of your life . . . Larry Gard, 2013).

Christman in this article with a business psychologist talks about how people can’t conceive of a life without a full work schedule—they feel such a life will feel aimless and unsettling.

Their work contributes to their sense of identity and also shapes how others view them. They worry about their roles in the family, what will they be doing at home, what their status is? If they retain equity, debt or an advisory role at the business, what will their role and status be? Lastly, they worry about their firm and employees and how it may affect them.

A business owner will probably face seller’s remorse. I say probably because the EPI 2013 survey shows 48% of all respondents stated that they have either “no plans,” or the general goal of “retire” post-transition, and only 4% of respondents have a formal written “life after business” plan.

Peter Christman writes about a three-legged stool in an exit:

  1. Maximizing the value of the business.
  2. Tax, estate, and financial planning at the personal level.
  3. Determining what you’ll do next.

If one of these legs fails then the stool—i.e. the business exit—falls down.

Note in exit planning we refer to exiting a business as a “transition”. This is because a sale to a third party is only one option, others include family succession, management buy out, employee trust ownership, recapitalisation etc.

“Personal Envisioning”

The rest of this article is about approaches to plan life-after-business so that you do not suffer seller’s remorse and an unhappy retirement but rather have a fruitful and happy 30 years on your terms. The jargon is “Personal Envisioning”.

Goal Categories

One simple way is to list the categories or themes of what is important to people:

  • health
  • family
  • money
  • travel
  • location and housing
  • personal assets e.g. boat
  • charitable work
  • business involvement

Then break these out into needs (required) and wants (desired).

This is the normal approach of a financial planner. They want to know your goals and then will help you assess what retirement fund you need at your retirement age to achieve the goals.

Let’s see if we can go deeper though to help you work this through.


S.T.E.P. stands for Spiritual, Things, Experiences, and People.

Also, a simple approach to think about retirement goals, I like the bucket list idea especially.

Spiritual. What motives and inspires you, where does your passion come from?
Things. What possessions do you want?
Experiences. This could be a bucket list including international travel, or it could be those experiences you have most treasured in the past.
People. Who do you wish to spend more time with? Wider family and friends of course but are there also people you need to thank, help or mentor?

These two approaches don’t really stretch you, the next two approaches require some real navel-gazing but may also be a more comprehensive approach to enjoying your retirement.

The E-Myth Approach

Michael Gerber, the noted small business management guru and author of E-Myth, talks about having a Primary Aim. He says,

“To identify your Primary Aim, start by forgetting about your business. This has nothing to do with your business. It’s about your life and what you want that life to be like. Remember, your business is a means to support your Primary Aim.”

Ask yourself some probing questions:

  • What do I want in my life? What don’t I want in my life?
  • How do I want my life to be on a day-to-day basis?
  • What would I like to be doing two years from now? Ten years from now? Twenty years from now?
  • Of all the things in my life, what has given me the most satisfaction or pleasure?
  • What if I had everything I ever wanted; what would get me out of bed in the morning?

Use those answers as a “springboard” to write more about the essence of your purpose in life.

This takes a less material and people approach than STEP.

He uses this process to ensure your business is put into perspective but its equally good for putting the next chapter of your life, retirement, into perspective too.

Stephen Covey

Lastly, and perhaps the most soul searching exercise is from Stephen Covey.

In his famous book, “The 7 Habits of Highly Effective People”, a success and time management book, he says one of the habits is to Begin with the End in Mind.

“In your mind’s eye, see yourself going to the funeral of a loved one. Picture yourself driving to the funeral parlor or chapel, parking the car, and getting out. As you walk inside the building, you notice the flowers, the soft organ music. You see the faces of friends and family you pass along the way. You feel the shared sorrow of losing, the joy of having known, that radiates from the hearts of the people there.

As you walk down to the front of the room and look inside the casket, you suddenly come face to face with yourself. This is your funeral, three years from today. All these people have come to honor you, to express feelings of love and appreciation for your life.

As you take a seat and wait for the services to begin, you look at the program in your hand. There are to be four speakers. The first is from your family, immediate and also extended —children, brothers, sisters, nephews, nieces, aunts, uncles, cousins, and grandparents who have come from all over the country to attend. The second speaker is one of your friends, someone who can give a sense of what you were as a person. The third speaker is from your work or profession. And the fourth is from your church or some community organization where you’ve been involved in service.

Now think deeply. What would you like each of these speakers to say about you and your life? What kind of husband, wife, father, or mother would like their words to reflect? What kind of son or daughter or cousin? What kind of friend? What kind of working associate?

What character would you like them to have seen in you? What contributions, what achievements would you want them to remember? Look carefully at the people around you. What difference would you like to have made in their lives?”

Covey calls this The Funeral Exercise. You can replace the funeral with your 80th birthday to make it a little less uncomfortable…

Stephen Covey also takes a role-based view of personal envisioning. By looking at each role you have in your personal and business life you can have more balance in your goals.

Personal roles include husband/wife, father/mother, friend, son/daughter, sibling. Also Individual/personal development, your role in developing yourself.

Wider personal roles include political, volunteering (Rotary), churches, sports clubs and schools. This can be done for your business roles as well e.g. shareholder director, manager – operations, manager – finance.

The other relevant Habit Covey talks about is sharpening the saw. For the purposes of this article, it is about ensuring a breadth of view of personal envisioning. Covey says you need preserving and enhancing yourself including your physical, mental acuity, social/emotional, and spiritual.

Physical is about your health, fitness, relaxation and sleep.

Spiritual is not just religious but also things like great literature or music. It could be nature as well, as a younger man I tramped many of NZ’s great walks and still remember the pleasure on entering a beautiful valley.

Mental is really continuing education. This could be reading autobiographies, history or sport. It could be attending lectures or speeches that stimulate the mind.

Social/Emotional is about your relationships with others. The obvious one is your life partner and truly understanding and developing that all-important relationship.

Post-Exit Themes or Goals

Whatever Personal Envisioning process you’ve used you should now have a good idea of what you want to do post-exit. We’re pretty ruthless in the exit planning world in that we don’t just want visions and plans we want action, in fact, its called “ruthless execution”. We do it for personal and financial goals as well as the business goals. Here’s how it works for the personal planning side.

From this list of personal goals from the personal envisioning process above, we choose 3-5 personal goals for the next year. The goals may include personal financial planning as well as personal planning.

We then split a goal into projects that can be completed in 90 days (“90-day sprints”). Each project is SMART—Specific, Measurable, Aspirational, Realistic and Time-based.

We then create an action plan for each of the goals which include a list of tasks and milestones at 30 days and 60 days with 90 days being the completion date. Each project has a deliverable—an outcome to be achieved. It’s on top of your current workload and so needs to be realistic.

The first projects are usually to do with de-risking. This is often about the 5Ds—death, disability, disaster, divorce, disagreement. Or it may be simply finding and briefing a good financial advisor. It could be seeking family alignment in the case of a family business.

You’ll likely be also running the same process for your business—but that’s another article.

Other Considerations while Personal Planning

I’ve purposely kept to the personal above but many business sales require owner assistance post-sales, part equity sale (e.g. PE fund, MBO), and vendor’s note. All of these options may lead to your receiving a higher price for your business but you may not be able to achieve your personal goals.

You also want to think about the desired level of confidentiality you have during the business sale process including with key managers, advisors and family.


Surveys of business owners show that 75% of business owners become dissatisfied with the result post-exit. A successful business exit or “transition” ensures each leg of a three legged stool is planned: 1. Maximizing the value of the business; 2. Tax, estate, and financial planning at the personal level; 3. Determining what you’ll do next. If one of these legs fails then the stool—i.e. the business exit—falls down.

We avoid this seller’s remorse by planning life-after-business as well as the business exit process itself. It often involves the family and certainly the spouse.

I’ll leave you with this poem from Peter Christman’s book The Master Plan: Exit Strategy For Successful Business Owners: Discover A Strategic Planning Formula for Maximum Company Value, Strong Asset Protection and Work-Life Balance (pp. 15-16). 

What Will Matter 
by Michael Josephson

Ready or not, some day it will all come to an end.
There will be no more sunrises, no minutes, hours, or days.
All the things you collected, whether treasured or forgotten, will pass to someone else.
Your wealth, fame, and temporal power will shrivel to irrelevance.
It will not matter what you owned or what you were owed.
Your grudges, resentments, frustrations, and jealousies will finally disappear.
So, too, your hopes, ambitions, plans, and to-do lists will expire.
The wins and losses that once seemed so important will fade away.
It won’t matter where you came from or what side of the tracks you lived on at the end.
It won’t matter whether you were beautiful or brilliant.
Even your gender and skin color will be irrelevant.
So what will matter?
How will the value of your days be measured?
What will matter is not what you bought but what you built; not what you got but what you gave.
What will matter is not your success but your significance.
What will matter is not what you learned but what you taught.
What will matter is every act of integrity, compassion, courage, or sacrifice that enriched, empowered, or encouraged others to emulate your example. What will matter is not your competence but your character.
What will matter is not how many people you knew but how many will feel a lasting loss when you’re gone.
What will matter is not your memories but the memories that live in those who loved you.
What will matter is how long you will be remembered, by whom, and for what.
Living a life that matters doesn’t happen by accident.
It’s not a matter of circumstance but of choice.
Choose to live a life that matters.