Will You Know When It’s Time?

“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.

Permission To Care

He told me, “Sometimes I just feel so lonely. Lost, in fact. Where did my friends go? I guess I just let work and family take up so much space that I’ve ended up feeling like a stranger in a strange land. I miss that I don’t have a universe of close men in my life. The worst part is feeling myself stuck in solitude as I try to navigate this place I’ve never been before.”

I could plug in the names or faces of hundreds of clients into that vignette. Men and women. A parent has just died or a child’s gone off to college. A divorce has left her stunned and reeling or he’s just found evidence of a child’s drug use that has escalated. A sudden diagnosis with a prognosis that feels unspeakable. Or relief that it was a false positive.  A “downsizing” that came from out of the blue or the successful sale of his company. Word that the bonus he was counting on won’t happen or that it did, but there’s no one to really celebrate it with. We all need someone to walk with us as we carry the joys and burdens of our lives.

One of the early exercises I do with each new client is to ask them to take a simple inventory of the current state of their life. A circle like a pie, divided into 8 slices. A snapshot of how full each slice of life presently is … work, wealth, health, family, fun, romance, friendship and meaning. You can do it now, yourself, on the back of a napkin or a piece of scrap paper. No one else needs to see it. Shade each slice to represent how full it feels for you. What do you see?

Friendship is often the place that has slipped for many of us. It makes sense that the demands of life have pulled our attention into other arenas. We can be so busy working and caring for our young families and climbing the ladder, just getting through the grind, that we look up and somehow we are alone.

I was on the massage table yesterday. I’ve seen the same massage therapist for years. We’ve walked through divorces, disappointments and injuries together – his and mine. It’s an interesting somewhat faceless intimacy that has developed between us. Sometimes I’m the one who talks through the massage. Sometimes he is. Sometimes we’re so busy laughing about some ridiculous thing that we both end up coughing.

He worked out the knots in my back as I processed the betrayal of old friends who had lied about the sale of a house to me. I’ve heard his pain when his ex-wife took his kids away on his birthday.

Yesterday we spent the ninety minutes meandering through updates about my vacation and his daughter’s upcoming birthday party. But, I heard something in his voice, something hollow. No, that’s not the right word. It was, perhaps, jagged. Like I thought he might cry. I asked. He said, yes, he felt like it was right there. He’d been watching sad movies trying to see if he could break it loose. No dice. I was worried.

He sounded like a client I’ve been working with whose father died recently, the one who has been so lonely.

I asked gently about whether he was spending time with friends. He said, no, he’d lost track of most everyone while he was trying to rebuild his life from the divorce and was sure none of them wanted to hear about this latest pain. He was sure he’d worn out his right to just say, “I’m lonely and I need some company.”  Besides, dudes don’t cry with each other. They don’t hug each other. He said “I just want to hear my dad or a friend say ‘It’s gonna be alright, pal. I’m right here with you.’”

Last week I was lucky enough to have lunch with another coach and we were talking about the unique thing that happens when we are willing to drop into the quiet space of caring for another person. How that intense poverty of loneliness can emerge in other people. Sometimes, when we are willing to meet it with kindness and a simple act of quiet care, it can heal – even, just a little.

I am always struck by how much a small act can impact that loneliness – the common human condition – that we are each holding, as if we are the only one, as if no one else could or would step into it with us.

I came across a funny little YouTube clip of this Mentos commercial. In it, children “mentor” adults (via an earpiece) to make conversation with a stranger, something most adults would rather avoid at all costs. It’s adorable and restores the simple humanity to both parties. Really, watch it, right now and come back.  I’ll wait.

While the kids have adults ask cheeky questions like “Can I tell you a story?” and say things like “I like your hair.” What’s more amazing is to watch faces relax and bodies return to ease.

Admittedly, I’m a little bit of a social experiment myself, but for years I’ve made it my business to ask the names of people who serve me – the busboy who fills my water glass, the housekeeper who makes up my room – and to look them in the eye, to greet them by name as I thank them for doing the simple service that eases my day.

Sadly, sometimes, they look afraid when I ask their name – as if they are in trouble and are going to be reported for failing at their job. Sometimes they ask, “Why?” I meet their frightened eyes and tell them gently that I appreciate them, what they are doing, and extend my hand to say, “I’m Denise.” Almost always, they grin, their faces relax and they shake my hand. Sometimes shyly, sometimes vigorously. But, their bodies change. They are seen. Not spotted, but seen – acknowledged, appreciated. A small slice of humanity restored. For us both.

As the busboy fills my water glass, I catch his eye and say “Thank You, Daniel.” When I pass her in the hallway, I say to the housekeeper, “Thank you for making my stay so lovely, Ariella.” The groundskeepers in my community I know by name and sometimes stop just to tell them that I appreciate the way they care for the grounds and how the new flowers they planted make my home so colorful.” Over time, I often choose to learn about their families, their histories, their dreams. It makes my life full.

In the handful of restaurants I frequent, I know the servers, the managers, they sometimes come and sit at my table for a moment or two when I am dining alone. They ask about my life, they tell me they missed seeing me, I hear about their children, their lives. Not because they want something from me or because I want something from them – just simply because caring builds my sense of connection in the world and eases my existential sense of aloneness. I do it whether I will frequent that restaurant or hotel again or not. It brings my life and the people who are in it into focus.

What must it be like to work invisibly, to be in plain sight and yet ignored? Do you feel alone? Do you wonder if you matter?

It is amazing to me just how simply we can ease that sense of being alone. Yes, close friends matter. It is important to cultivate those friendships. Like any living thing, they need attention, care, to be watered and nurtured.

Perhaps you have drifted away from those friends. Your lives have taken other paths, you’re all busy. But, it is an act you can cultivate. With a simple smile, a simple greeting delivered with eye contact. With a phone call, a coffee, not with an email or a social media post or a like.  You really do have permission to care and to both give and receive that care all around you.

A while ago, I started carrying with me some small inexpensive glass hearts. I read a column about it and decided I would give it a try. I find one person each day to offer the heart to. I make eye contact, say “You have the most beautiful shining heart. I can feel it just standing next to you. This is for you.” And I hand them the heart – men and women.

I didn’t think of this, I read about it, and it touched me. What I’ve seen over time is that it can impact others in ways I couldn’t have imagined. It is a tiny token, a moment of feeling seen in their goodness.

Often my gesture is met with tears or an ask for a hug. It has changed me.

A client recently told me that he had decided to pull back from mentoring his team so much because he learned that their efforts weren’t going to be calculated into his bonus. He wondered why he should bother to invest time in their growth if it wasn’t going to count in his favor. I asked him to take on this task, to carry the hearts, to find one person each day to offer one to. To let his intuition guide him as to who. Can you guess what shifted for him? What could shift for you?

Yes, our work is important. Yes, working hard matters. Say yes, to allowing yourself to care. In fact, give yourself permission to care. Right now. We need you. We need it. You need it. More than you will ever know.

Building Your Courage Muscles

I was talking to my massage therapist the other night about a workshop called Courageous Choices that I led recently for a group of senior executives. I was preparing them to exit their companies and discover a legacy beyond just money.  Helping people make courageous choices is at the heart of what I do as a Transition Coach.

Our lives are filled with moments of choice that lead to transitions. Whether it’s taking a new job with a different company, asserting new boundaries within an important relationship or a significant transition like exiting your business – each step toward change requires moving beyond a well trod comfort zone and that takes courage.

For most of us, the path from the Land of Wishing to the Land of Having requires us to step through the Gate of Doing. Typically, we step through that gate only when a) the pain of staying where we are is too great to stay put or b) the desire for that for which we have been wishing becomes strong enough to overcome the inertia of resisting. I’ve seen that pain come from any of a thousand different avenues for the people I work with – getting fired, not being able to raise the next round of financing, learning your spouse is preparing to leave you, a serious medical issue, death of a loved one, the empty nest or a gnawing restlessness that you just can’t put your finger on but you know you just can’t keep doing what you’ve been doing any longer.

Nearly everyone finds that “wanting” something to be different may be the starting point, but as the old saying goes “nothing changes if nothing changes.” Change requires action, plain and simple – there’s no avoiding it.

It is often fear that keeps us from taking the action we most need to take to see the changes we desire. Fear is not the enemy, inertia is. Fear challenges you to build your courage muscles and when you make friends with fear by stepping outside of your comfort zone, your comfort zone expands.

Too often we hold ourselves back from taking the steps that will improve our lives and fulfill us, hoping that our fear will go away. The fear that you might not make enough money or that you won’t be viewed as successful after you leave your company or that someone is going to be upset about your decision can keep you stuck where you are, hoping that “some day” you’ll wake up and feel the courage to try something new.

Believe me, courage is not going to find you, you’re going to have to tackle that fear and step into the courage whether you want to get a new job, give a speech or leave a relationship that just clearly isn’t working anymore.

Elizabeth Kubler-Ross, the pioneering psychiatrist in the work of grief surrounding the dying, found that the most oft-cited fear was the fear of death, even though we all know that it is inevitable and unavoidable. Her research showed that those who felt they understood and acted on their purpose in life or found special meaning in what they had been able to do were the ones who faced significantly less fear and despair in the final weeks of their lives than those who had not.

Identifying the work we are meant to do in this world and the strength of character to do something that frightens us and then deploying the physical or mental or emotional willingness to do it is empowering and exhilarating. It requires reflection, introspection, a willingness to look at things in a new way, and the courage to actually step out of one’s comfort zone and do something different and unfamiliar and yes, sometimes, frightening.

Often I hear “What will other people think or say if I (fill in the blank)?”

Self-esteem is frequently measured in terms of our perceived value to others.The fundamental question here is how you feel about yourself. What is the value you place on your very existence? I mean this as much in the deep dark of night when you might be alone, as during the day when you are actively serving a purpose, or some other time when you may have company around you.

What do you believe is the source of your value? We could cast this question many ways: economic value, intellectual value, emotional value, companionship value — or something much closer to the core of who you are.

I’ve suggested before that self-esteem is the single most important issue we face as individuals, and which aggregates into a collective situation that is holding back the progress of all of society. Imagine if we could all feel better about ourselves, love ourselves more, and be in close harmony with the fact of our existence. What, then, might you find the courage to really do with yourself?

In esoteric studies, the concept of death is synonymous with the concept of change. Without change, progress is impossible, and the resistance to change, progress and the mere consideration of death are the same thing.

It’s fair to say that most people avoid the topic of death, to the point of rarely if ever talking about it, thinking about it, planning for it, or seeking some true, personal understanding. Typically, the only time there are actual confrontations or conversations are when it’s right in our face.  Besides that, death is usually relegated to the realm of unspeakable inner fear of the unknown.

It is my observation that a significant part of the obsession around professional and financial success in society are rooted in struggles with both self-esteem and a sense that we can somehow avoid the inevitability of our own death by accumulating enough praise or resources.

A fellow I’m working with has become clear about the specific step that he needs to take to have the life of his dream, one he’s been dreaming of for as long as he can remember. He admitted that he was worried about what his family and friends would say if he took this step. He wasn’t sure he could stand up to their criticism of his decision, even though he knew that if he didn’t act soon his dream would really be beyond his reach. I shared with him a favorite quote: The opposite of courage is not cowardice, it is conformity. – Rollo May

Courage is the willingness to act in accordance with one’s beliefs, especially in spite of criticism or disapproval of others.

Many people stay in jobs they detest, continue to run companies they have outgrown and go to events with people they despise or behave in certain ways that violate their integrity just to please other people, all the while draining their life force into the pit of conformity for the poison pill of approval. To me, it is a sad waste of a life. After all, I often half-joke that if your friends think less of you for chasing your dream, you need some better friends! And, families often use the tool of guilt to manipulate their loved ones into conformity because of their own fears and wants.

While it’s easy to confuse courage and bravery, I think courage is not the absence of fear, but the resistance to fear and mastery of that which you have not yet achieved.  How long will you wait to claim the life that is yours alone to live?

Here are some questions I use to regain my courage:

1. What do I really (in my deepest heart) want? (Be precise)

2. What do I need to do to have that? (List every action)

3. What am I afraid of? (List every fear, no matter how silly it looks in writing)

4. What does avoiding this fear cost me?

5. What would I do if I weren’t afraid? (List every action)

6. At the end of my life, will I regret not having done this?

7. How will my life benefit from facing this fear?

8. What else might I be able to do if I faced this fear?

9. What specific actions must I take in spite of this fear so I may have what I want?

10. What one action am I willing to take today and who can I ask to support me?

We might come up with a thousand reasons why we are all unequal, and why some people are seemingly more powerful, though we all face the same fate, and we all live on Earth with limited time. Were we to admit that fact, we might want to have more fun and do something more meaningful while we’re here.

Dear friends, I want for you the life of your dreams. You deserve it, you’re worth it and as Christopher Robin said to Pooh, “Promise me you’ll always remember you’re braver than you believe, and stronger than you seem and smarter than you think.” If you need me to be your Christopher Robin, I’m here.

Can This Deal Be Saved? The Art of Asking “What Matters?”

Last week I was talking with a banker about how to save a deal of his that was spiraling out of control. It seemed the Seller had become less and less responsive over the past several weeks and then, suddenly, threw up a wacky deal term out of nowhere that threatened to kill the deal. The entire deal team was left scrambling wondering, “Where the heck did that curve ball come from?”

He had sought me out to see if I had any ideas about how we could get his deal back on track, as one of the attorneys involved had brought me in on a prior deal and told him I was “A CEO Whisperer.”

I asked the banker a single question… “What Matters?”


At the same conference where I spoke with this banker, I had the privilege of spending time with some first time attendees. I offered to each of them that they could use me as “home base” during the conference. I told them, “Any time you feel out of sorts or don’t know how to begin a conversation with someone new, come join whichever conversation I am engaged in and I will readily introduce you to the person I am talking to. You’ll meet some interesting people.”

One of these new people said to me later, “Denise, you rarely start a conversation with a question about what that person’s job is or what their company does. Why?”

To me, that’s inconsequential small talk that doesn’t matter. People get bored with repeating news, sports and weather – or its business version … “What do you do? What does your company do?” They’ve already answered those questions several hundred times during the conference before they meet me. You can tell by the way their voice falls flat and their eyes glaze as they give their standardized elevator pitch.

You might be saying to yourself, “But that’s what we do at conferences, we try to learn about each other’s business. It’s business development that takes us to conferences, after all, Denise! I can’t afford to spend time talking to every person who’s there.”

I’m going to challenge you on that before we return to my conversation with the banker. How much do you actually learn about the other person or their company with that standardized line of questions about “what they do”? And, how long do you stay involved in a conversation with that person once you satisfy your ulterior, yet unspoken, question “Can I make any money from this conversation with you?”

One of the newbies at the conference said to me, “These firms all sound the same to me. It’s hard for me to really suss out how they’re different from each other.” I just grinned. He was like the child who said “The Emperor has no clothes!” He had revealed a truth that few wish to acknowledge. Most of our businesses are not really that different from our competitors.

The reality is that most of us are more inclined to do business with people we trust, with those with whom we have relationships and with whom our “what matters” aligns.

Through our carefull (it’s not a typo, I meant filled with care; not walled off, exploitive and deceptive) conversations, we have an opportunity to learn what matters to each other and discern with whom we will enjoy doing business.

I think I’m lucky that my business name opens the door to a deeper conversation. Nearly every time someone looked at my name tag, they would repeat back to me, “Chase What Matters. Huh, what matters?”

I live for those moments. The ones where we’re going to drop down a layer into something richer. It’s those conversations that are going to become doorways to relationships. Relationships are what drive our businesses. Without them, they are simply mechanical transactions, devoid of the essence of What Matters to either party. It leaves us stuck in roles, unable to bring our unique creativity to the equation of business before us.

If you check in with yourself, you can recall the differences between deals you’ve done when you were in a relationship with the other party and when you were simply a transaction to be done. How did it feel? Whose “what matters” ruled the interaction?

Learning What Matters

What matters to me? You’ve probably guessed, it’s depth. Deep relationships, conversations with substance, genuine connection and meaning. I’m wired for connection and service. But, before I can serve, I need to know what matters… to me and to the person I am about to serve. It’s no different for you and your business.

When I have the opportunity to reflect the question back … “What Matters to YOU?” … I’m often rewarded with a glimpse behind the façade. Often, what I hear is about their humanity and what gets in the way of them living the full life they crave. A deeper, meaning-filled life. The shallow “wants” fall away as we talk about What Matters to them.

That changes the interaction … immediately, we’re dropping into another space together. One filled with import and meaning. I always pause. As if we have our hand on the knob of a door and we are crossing the threshold of a room together, because that pause breaks the momentum of habit. It gives us a choice. That choice, the only choice we really have, is to be open or closed, to the meaning of what matters to each of us in what we are about to embark upon together.

Moments of meaning and depth define us. They shape our choices. They create new opportunities. But we must be open to a different kind of deeper conversation about What Matters as we become the authors of our lives or assist others in their businesses.

Applying What Matters to the Deal

The banker asked me, “Can you get this deal back on track so it will close?” I asked him if that was what mattered … and to whom.

I’m not clueless about the financial implications of having a deal not close. I get it, the entire deal team and all of its players have time, money and resources at stake in getting this thing across the finish line. But force alone isn’t going to make it happen, nor should it.

When I ask What Matters? I want to know many things – whether closing this deal, at all costs, even if it is to the detriment of their client, is what matters to him and the rest of the deal team. I want to know what matters to his client beyond this deal and what is getting in the way of it for him. I want to know where their mutual What Matters align – beyond just the financial elements – and whether we can get them to align in a way that will allow the deal to successfully close or whether everyone’s interests are best served by walking away sooner rather than later, without anyone feeling exploited.

The way we do deals leaves an imprint on us and our deal partners. It’s why understanding what matters (preferably, earlier rather than later) and being open to the deeper, care-filled conversations along the way is better for everyone involved. It leads to less strain, more satisfaction and better subsequent collaborations between deal partners. Facilitating those deeper conversations among deal partners is an art and it comes from a different place than the one we use in purely linear, “just the facts” deal making.

In my experience, this sudden curve ball in a deal typically means that there is an emotional need of the Seller that isn’t getting met. Perhaps he just got scared because he remembered watching his father die shortly after retiring and he can’t imagine what he’s going to do with himself after the sale of the business he’s spent his own life building. Perhaps he just learned that his dream of sailing around the world isn’t going to happen because his wife finally told him she has no interest in traveling away from the grandchildren. Perhaps his best friend told him he should hold out for more money and he’s afraid of looking like a chump.

What we know for certain is that What Matters, what really matters under the sudden curve ball, needs to be addressed. It probably ISN’T about what it looks like it’s about, either. And, the Seller isn’t going to tell it to someone whose What Matters isn’t aligned with theirs. Once I get to be with the Seller, to understand What Matters and we address the underlying emotional needs, then we can ferret out next steps toward resolving the deal.

And, if you don’t know what really matters to you or you don’t care about what really matters to your client, it won’t matter how many of those shallow networking conversations you have at a conference. No matter what your pitch is, eventually, others will recognize that the only thing that matters to you is forcing a solution that satisfies your needs. All that networking and business development will be for naught in the end and you’ll be left with the truth of your life and the way you conducted yourself – as a selfish player who didn’t really care what mattered to anyone else. I know you are better than that at your core.

We’re talking about your business and your life and those of the people who entrust their lives and businesses to you. So, do the work to get clear about what matters and chase that. I can promise you, it really is about more than whether you close this single deal.

The Legacy Dinner

The Legacy Dinner is a small curated dinner & discussion experience exploring the topic of What Constitutes a Lasting Legacy?

It is an informal gathering, along the lines of a Jeffersonian-style dinner.  For each event, I’ve chosen a variety of people I know who I think are open to discussion and would each bring a unique perspective to a shared conversation.  In advance of the evening, I will provide the address of the unique venue and LinkedIn listings for each of the guests, so that you may have a gander at who your dinner-mates will be.  Guests at prior events have said that it’s a dinner unlike any they’ve ever attended and that they made rich acquaintances that far surpassed any networking event they had ever attended.

The format for the evening is that once we all have arrived, I’ll ask each of you to share your answer to this opening question: If I could choose to take on the life of any other person (living, dead or fabled) who would I choose and why?   Your answer can be whimsical, lighthearted or deep.  You may wish to share an anecdote or two about how you came to that answer.

We will meander around the topic from there.  The only guidelines for the dinner are to have conversation as a group, to resist the urge to talk separately and to have fun with the topic.  We may disagree, but let us not be disagreeable!  It’s an opportunity to get to know each other and explore a common topic together.  There is no right or wrong answers, and I’ve chosen each guest because I know you can bring your full selves into the conversation, exploring a topic without any need to posture or prove anything – it’s why I enjoy each one of you so much!

At the end of the evening, you’ll each have an opportunity to share your perspective on the evening.  You may share what moved you, what (if anything) has shifted in your perspective, what you plan to do next, or any other comment that you wish to close with.  We will conclude by 9pm.

I’m looking forward to sharing this time with all of you!  Denise

Is Money Your Security Blanket?

In many of Charles M. Schulz’ Peanuts  comic strips, Linus’ security blanket is prominently featured.  Linus loves his blanket, carries it everywhere, often while sucking his thumb, and is not embarrassed by it.  He cannot survive without it and really suffers when it is being washed.  However, in strips from the later years, Linus seems to want to get rid of it, even though he knows he is a mess without it and the illusory comfort it has come to represent.

Several times a week I hear a client say some variation of this:

For me, money represents security.  Having money means being secure; not having money means that at any given moment my whole life could come crashing down.

I talk clients off the ledge weekly about their (typically unfounded) fear of impending financial ruin, no matter whether the amount in their bank account is in the hundreds, thousands or millions of dollars.

A small child tucked in their bed at night doesn’t feel safe if they believe there is a monster hiding in the closet.  But, the consistent, reliable, warm embrace of a mother’s hug may make a child feel safe.  We all know that a mother’s (and father’s) love alone is not enough to protect her child from the world which surrounds them, but it does go a long way toward creating that sense of safety that they will carry into the world with them.

Only when we are certain of our emotional and physical protection are we – in effect – SAFE.  So where does security come into play?

Think of SECURITY as if it were the overarching umbrella protecting our SAFETY.

Let’s take a look at how money and security became tied together in one of my client’s brains and see if it mirrors how you feel.


Like many people who begin to equate money with security, Mark formed an association between security and money early in life.

When Mark was a child, his father was consumed by financial worries.  His father put in long hours, often traveling for his work.  When he wasn’t working, Mark’s father was depressed and irritable, worrying about not having enough money.

When his father was earning what he thought was “enough” money, there was a sharp reduction in tension and the subtle but palpable sense of impending doom that permeated family life.  Not only were there new toys, but sometimes Mark’s father would actually relax, smiling and laughing with the children, take them to a movie or tell them stories.  That’s when Mark felt most secure.

Over a period of years, Mark absorbed the fearful energy that emanated from his father about never having enough money.  It had undermined his sense of security and evolved into his own dream of someday having a lot of money.

Mark tells me that when he has enough money he won’t have to worry any more.  He thinks then he will be free of this insecurity and fear that plagues him.

In attempting to cope with the anxieties of life and never having developed the solid sense of inner security that comes from feelings of trust and dependency gratification from people, Mark narrowed his view of the world.  He has focused his entire attention and energy on one aspect of it – money.  Like Linus’ security blanked, Mark retreats from the anticipation of impending disaster (real or imagined) and relies upon the illusory protective power of more money to make himself feel safe.


The sad reality for Mark, and other “security collectors”, is that once money becomes the perceived source of your security, no amount of money is sufficient to allay the fears and provide enough security to stop pursuing the money.  It matters little if the numbers are in the hundreds, thousands or millions.  There is always the recurrent fear that tragedy could come along and wipe it all away which only adds to the person’s anxiety and distrust.

Not only does the money NOT reduce the feelings of emotional insecurity, but my clients like Mark admit that knowing others look up to them, providing them with respect and admiration, makes them LESS willing to allow themselves to seek avenues to satisfy their needs for emotional security.  Instead, they discover that using money as the measure of security fuels their fear and suspicion of others.  The more money they acquire, the more they worry about losing it.  And the fear of losing it makes them even less able to enjoy it, setting up a cycle of becoming ever more defensive rather than relaxed, thinking that when they have “enough” THEN they will relax.

Instead, they become further deprived of social pleasure and connection, ignore their physical symptoms, often sacrificing their physical needs to their financial compulsion.  The preoccupation with money leads them to work longer hours, even when it means enduring intense fatigue.  Happiness, relationships and health all suffer as they become secondary to the illusory security of money which they continue to pursue.

Many of these talented, well-resourced professionals suffer from a persistent poverty complex – I consistently hear a panicky distorted fear that they will end up eating cat food while living in a van down by the river.

Where Does This Fear Come From? 

If the dependency upon parents or others in authority does not provide a feeling of protection and safety, the child learns to distrust people and seeks something else to rely upon.  While Linus turned to his blanket, frequently, that something else is money.  If having money reduces anxiety by making the person feel less dependent upon others, money may replace people as the preferred source of security.

Without basic trust, safety and security is impossible and responsible adulthood is impossible.  Children who grow up with inadequate emotional and relational security become anxious and insecure and feel incapable of dealing with a world that feels overwhelming, overpowering and threatening.  Which leads them to seek an alternate form of security; like Linus’ blanket, money becomes the thing they use to soothe themselves.

People who develop a sense of distrust are constantly on guard to protect themselves from getting hurt – physically, psychologically, or financially.  Originally the fear is most likely physical – the fear of physical pain and suffering, possibly even the fear of death.  Very real for a child who is dependent upon adults.  Next the fear my be psychological – the fear of rejection, loss of love, humiliation and the like.  Eventually, however, as the person depends more and more on money for ego satisfaction and security, the fear of FINANCIAL loss becomes paramount and mimics those same physical symptoms of fear.  Preoccupation with the threat of losing one’s means of security does not create an environment conducive to pleasure, instead they end up substituting a psychological payoff to ease the anxiety and end up creating a cost to the self in unhappiness and emotional damage.

In one series of strips, Lucy uses Linus and his blanket as a science fair project.  She shows how Linus gets dizzy, nauseous, and eventually passes out when he is deprived of his blanket.  Have you ever felt like that when you got anxious about money?

People like Mark who are security obsessed are consistently turning a distrust of people into the trust of money and trying to find a feeling of safety in money to offset a feeling of emotional insecurity.

The most sinister aspect of using money as your source of security is what you’re unwittingly doing to your kids.  When you convince yourself that there’s no harm in allowing money as your substitute for emotional security/relational connection, never forget that they are watching and learning about the world from you.

What parent hasn’t responded to a child’s complaint about how much the parent is working … “Yeah, well where do you think the money comes from for this roof over your head, the food in your belly (or fill in the blank)?”

The message your child receives as they watch you is “If I didn’t have to provide for you/your future, I wouldn’t have to work so hard.”  It is unintentionally shaming and leaves their plea for connection with you unmet, showing them that the true source of security they can rely upon is what you provide through money and things, not affection, time, attachment.  Even when you think you are indulging them, they receive the underlying message that money is what matters and on what they can depend most.  Your children learn to deny themselves the security of connection in favor of money as their substitute sense of security.

When the amount of affection is in short supply because of time, family conflict or detachment, kids turn away from people as the source of affection and security, and seek gratification in the collecting of things/money.  They learn early on that they cannot depend upon their parents for consistent, reliable relational security as they are given things instead of love/time and so their sense of identity begins to come from attachment to possessions.  Dozens and dozens of my clients admit to attaining their sense of purpose and warding off the feelings of isolation and loneliness by pursuing money.  Money has become safer than people because it can’t abandon you, make you angry or make demands upon you.

They admit that their primary goal is not to become happy or successful (although that’s what they tell the world) – it’s to be safe.  The answer to all their problems is to get more money which will make them impervious to any potential catastrophe.  When they feel anxious or threatened in any area, they seek security by increasing their money supply.

The problem can’t be solved with money, it’s about trust.  And it’s not about trusting someone with their money, it’s about trusting someone with their emotional safety.  But, repeatedly they withdraw from people, putting their trust in money.  They resist becoming dependent upon people, hiding their craving for dependency and connection.  They view people as being unreliable and undependable, insisting instead that money can always be relied upon.  People can reject or abandon, but they can hang onto money.

These same brilliant professionals tend to continue to lodge themselves in the trap, so it becomes increasingly difficult to get out of it.  Despite any pretense to the contrary, money is more important to the security collector than people.  Money becomes an aspect of almost every decision they make.  Not only is it a consideration, it becomes the primary   consideration.

How to Find Real and Lasting Security

It’s not hopeless, but to be certain it is difficult to break out of this trap because it’s long rooted and socially sanctioned.  Having learned to reduce anxiety and vulnerability by relying on money, not people, means shifting the dynamic around trust – and choosing trustworthy people who value relational and emotional connection and safety.

Since relying on money seems to work, and is in its way reassuring, it becomes self-reinforcing – although it is an illusion.  Having learned how to relate to people in ways that ensure they will appear as untrustworthy as you believe them to be, you must watch for the unconscious motive to justify and perpetuate the distrust.

My client, Richard, is a prime example.  After 40 years of instilling in his children the idea that money is the only thing in the world that can be trusted, and therefore should be accumulated at all costs, Richard learned that he was dying.  He bitterly bemoaned the fact that his children’s only interest in him seemed to be related to their inheritance.  He took no pride in the fact that they had learned so well the lesson he sought to teach them.

It takes time to learn to trust others, to return the focus on relational safety.  Trusting, becoming involved, loving, being dependent, needing – these all involve risk.  The person who devotes every waking moment to being safe essentially avoids living.  One of the unexpected benefits of developing trust in others is an increased trust in yourself and your abilities to cope effectively with the problems of everyday living.

Reclaiming intimacy with others after one has been hiding behind the illusory security fortress of money is not simple or comfortable.  The alternative, however, is the annihilation of one’s humanness and its replacement with the empty, dehumanized despair that comes from trying to find emotional nourishment and satisfaction in things.

Of course, you could always just buy a nicer blanket.