Will You Know When It’s Time?
Denise Logan

“Now just feels like the right time,” said Steve Croft (age 73) on Sunday as he announced his retirement after 30 years at the CBS News show 60 Minutes.  He said he’d been considering when to retire at the end of each of the past four seasons and knew it was finally time.

Hearing him say that he wanted to leave while he still had the energy to enjoy life and the curiosity to explore different things made me think about how wise he was (finally) being.  I say “finally” because way too often I hear this sentiment – “I’ll retire when the time feels right.”

Google the phrase “when to retire” and you’ll be inundated by articles with titles like “Top 5 Retirement Mistakes Boomers Make”.

Most days I feel like retching when I read headlines like those because the articles focus almost exclusively on the financial aspect of retirement planning and play upon the reader’s fear of running out of money before he dies while completely ignoring the emotional preparation it takes to retire well or, worse yet, the utterly avoidable wreckage that follows when one is forced to retire unexpectedly or dies prematurely without a plan.

Those articles rarely say a lick about the ACTUAL mistakes people regret when focusing solely on the financial aspects of deciding when to retire or the consequences on their families and businesses.

Regrets like these I’ve heard from clients in recent months:

  • Retiring feels like “death” to me because I realized too late that I have no life to retire TO.


  • When I finally decided it was time to retire, I no longer had the health or emotional stamina to make it through a lengthy sale process and I had mistakenly assumed that when I was “ready” a buyer would magically materialize and cash me out quickly. Boy, was I wrong.


  • My health was a wreck and I couldn’t actually do any of the things I had put off forever in the pursuit of my obsession to be financially secure for retirement.

Is Dying at Your Desk Noble or Tragic?

I facilitated a retreat recently for a group of business owners to talk about how to know when it’s time to sell their business and retire.  One of them announced – “Not me, I’m planning to die at my desk.”  Another said he was afraid of running out of money.  A third said that he had heard too many horror stories about company owners who dropped dead right after selling their companies and he had no intention of becoming one of them who died of boredom.

I pushed back a bit on these fellows – what if the reason that an owner died shortly after selling his business wasn’t because he sold too soon but because he sold too late?  Perhaps he waited until his health was failing and “had” to retire.  As for dying of boredom, I asked them to consider the state of their relationships in the context of research that shows loneliness is as bad for your health as smoking or obesity.

Steve Croft shared a brief anecdote that his 60 Minutes colleague Morley Safer had warned him “Don’t stay too long, Steve”.  Morley died of pneumonia at age 84 one week after retiring after 46 years at the show.  Think he might have stayed too long? How is it that you think you’ll “just know” when he didn’t?

At this retreat, the executive who said he was planning to die at his desk said something that made his wife’s face fall in despair when I asked him why he was planning to die at his desk.  “Because it’s the only place I feel truly alive.”  Ouch.

Retirement Feels Like Death to Me

Retirement is 10th on the list of the top 43 most stressful life events (according to the American Institute of Stress) – 6 points above financial stress – but in the same decile as things like death of a spouse (or a child) and divorce.   It’s actually no surprise that we find retirement, death and divorce in the same stress bucket.  They’re all transitions and, transitions can feel stressful, especially when we don’t talk about and prepare for them.  But, the truth is, it doesn’t have to be this way.

More than sixty percent of business owners think they will “know” when it’s time to retire and will be able to plan for a sale when that time comes.  As a consequence, fewer than thirty percent of business owners have an exit strategy or succession plan in the event of their unexpected departure or death.  Many of them play the “One More Year” game, assuming that time is on their side assuming they can safely continue to delay the inevitable.

The problem is that there is a significant disconnect between when people THINK they’ll retire and when they ACTUALLY retire. Almost half of the population (48%) incurs an unplanned retirement event – often to cope with a health problem or disability of their own or to care for a spouse or other family member.   That’s a huge problem.

The reality is that every owner will leave his business, with or without a plan.

The result is that in an effort to maximize economic security by focusing our attention on “getting just a bit more” we perpetuate the twin myths of “Time is Money” and “I’ll Know When It’s Time” ignoring a huge risk.  Then, when an unexpected departure happens, the capacity and stamina of those who need it most to get through a transition is significantly diminished.  The result is that the failure to plan for an inevitable transition ends up leaving everyone affected traumatized and with an even greater loss of security and confidence in the world around them.

Take the case of Barbara, Brian’s wife, who told me “My husband thought it was a joke to say he’d ‘die at his desk and leave me wealthy and in charge of the business.’  It was no joke when my ability to grieve his unexpected death was sidelined by all the clients, staff and vendors who needed my attention.  The reality was that the estate received only a fraction of the business’ worth and, if he wasn’t already dead, I’d kill him for leaving me in this mess.”  The sad news is that this was avoidable.

Does continuing to own your business really keep ill health, death and boredom at bay?

Ironically, perhaps the best time to sell your business is when you don’t have to!  You cannot expect a good deal when your back is against the wall.  Most business owners hesitate to sell when the times are good or to even contemplate their exit.  Selling when there is no other option understandably gets you a less-than-enviable deal.  Any issue such as the business owner getting burnt out, the owner having health issues and/or the business losing a key customer can make a business virtually unsellable, or sellable at a much reduced value.

A burnt out or unhealthy owner does not have the energy and will necessary to keep the business growing and expanding.  Little effort is put in to seek new markets and tap into new customer bases.  The staff may become uninspired, the key customers may head elsewhere and the business may lose its wings.  Buyers aren’t interested in buying businesses on a downward curve.  Many business owners find themselves in similar situations and are forced to sell from a place of weakness, all because they thought they’d know when.

Your retirement plan may completely depend on a successful sale of your business.  If so, you cannot let your declining energies bring down the value of your business.  It is important that you recognize the right time to sell your business and put it up for sale when it is still going strong and you still have stamina.  Buyers are not only interested in stability; they are looking to buy businesses that are likely to grow in the future.  Think you’ll “know” when it’s time?

Don’t Let your Business Die with You 

Does that sound dramatic? Companies where the founding CEO dies are statistically more likely to go out of business.  They rarely survive and the family is typically forced to sell the business way below the market value compared to what the business was worth if the business owner was still there.  Even for those few companies that do survive, the ripples from sharp sales drops and instability continue or even intensify for 5 or more years after the founder’s death.

Think it can’t happen to you?  Stanford GSB did an impressive study that showed, on average, 7 CEO’s of publicly traded companies die each year (most commonly from cancer, heart attack, stroke or airplane, auto or other accidents)  The typical financial hit each company sustained was substantial, especially in the absence of a plan.  And, these were public companies with strong leadership teams in place to backstop the sudden loss of a CEO.

Paradoxically, Talking about Death, Retirement and Having an Exit pPlan Creates Resilience and a Sense of True Security

Talking about death and money have long been cultural taboos.  Interestingly, we’ve come much further along in our willingness to talk about money than we have in talking about death.  We live in a death-phobic society and look at death as something separate from our lives that we want to keep at bay, as far away from us as possible.  We avoid talking about it at all costs.  And the misperception is that if we avoid the subject we can avert the experience and avoid the fear.  Worse yet, we have conflated thinking about retirement as thinking about death, by focusing so heavily on the fear of economic loss.

We all know it’s crazy, but there is a reason why we look away from the topics of death (and now retirement.)  Psychology sheds light on it through the terror-management theory.  In a nutshell, it means that when we’re faced with the idea of death (and the loss of things we have conflated with death such as money or connection), we defensively turn to things we believe will shield us from death, literal or otherwise.  Currently, that thing society is using to focus our defenses on is the illusion of financial security as a way to shield ourselves from death (and financial loss to which the fear has similarly become attached).  The problem is that Time is NOT Money, Money cannot buy more Time.  The thing we are innately aware we will run out of is time.  We have moved our existential fear of running out of time onto a defense that falsely assumes that if we focus on running out of money, we can forestall running out of time.

The problem is that shifting our focus to money doesn’t work.  In fact, it simply makes us more afraid of the impending loss of time.  Think about that the next time you’re tempted to click on the stock ticker or an article that purports to tell you how to avoid the pitfalls of retirement, as a way to calm yourself.  The actual way to feel secure in retirement is to focus on your mortality and double down on your connections with people important to you.

An interesting study found that people who were naturally more mindful of the reality of their mortality had less fear and anxiety – both about death AND money – and were able to take in a greater sense of safety from being in connected relationships, purposeful community engagement in causes that they care about.  Even better, they experienced significantly less stress following illness, the death of loved ones, retirement and financial setbacks.

Death Doesn’t Send a Calendar Invitation – The average life expectancy in the US is 78.69 years. What does that mean for your mortality reality check? Most of us subconsciously believe we will live for a long time – no matter our current age or health, even though we all know someone who died before that statistical “average” number.  Thinking about and discussing our mortality forces a self-evaluation process and life review that is unnerving for many of us.

But talking about death is important, because it means we’re talking about life.

I’m lucky enough to have this conversation with clients – a lot – mostly because I prompt it, no matter the transition I’m working with them on – changing careers or selling their business.  I’m currently working with two clients who are actively facing terminal illness and one other who luckily only had a scare last year.  Each of them has told me that, when faced with his mortality, ‘You see life as you should see it.”  One told me, ‘It completely put my ambition and what matters in their rightful perspectives.’

Will you know when it’s time and what to do then? Don’t wait.  There’s a reason I named my company Chase What Matters.

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