I recently met a wealth manager named Amy who had that very reaction.  She asked me why I thought that made her lucky instead of cursed.  I invited her to join me for lunch later that week and promised she’d see what I meant.

She and I met at a local restaurant for lunch with a lawyer, a banker, and an accountant – I know it sounds like the opening to a bad joke or, perhaps, the most boring lunch you can imagine depending on your perspective (and no we hadn’t just walked into a bar!) but keep reading.

The four of us first met as the team of professionals involved in helping our mutual client, Jeremy, sell his business and we have continued to meet for lunch or a drink every other month since then, even though Jeremy’s sale has long-since successfully concluded.  Amy was surprised to learn that it’s an appointment each of us keeps, no matter what else might try to intrude into our calendars.  She wondered why we continue to invest this kind of regular time with each other even when we’re not working on a current deal together.

Here’s what we told her.

“Amy, remember when I told you that you’re lucky if you’re spending half your time as a part-time psychologist with your clients?” I asked.

“Sure,” she replied, “but I can’t imagine why you think that makes me lucky.”

One of the others pointed out that, in every single deal he’s ever been involved in, he realized someone was playing that role of “therapist” and, most often was someone who resented it and wished the business owner would “just get a grip on their emotions” and “act rationally.”

“The reason Denise says you’re lucky if you’re the person the owner has chosen to bring their emotions to is it means you’re the person they feel most safe with in the deal. It means that the other professionals AREN’T making the owner feel safe enough to let down their guard and share with them what’s really going on inside,” my banker friend said.

“That’s right,” continued one of the others.  “Once I realized that I was the one person the owner felt safe with, I recognized it was an honor, not a burden.  But, I also realized that with that honor came a greater sense of responsibility.  If they were trusting me with their emotions, I knew I needed to dial up my own understanding about how I could help them better.  I began to look for ways to bring even more of that sense of emotional safety into the relationships I built with my clients.”

My banker friend added, between bites of his burger, “That’s right, while it started when Denise pointed it out in this deal with Jeremy, once I caught on, it happened for me in other deals, too.  Clients started to tell me what was really going on under the surface for them, instead of making stupid moves and unrealistic demands.  I began to see how much easier it is to solve the issues that used to cause things to inexplicably unravel at the eleventh hour and I started closing more deals.”

Amy said she thought that made sense but that she was worried she wouldn’t know how to handle it if her clients started to get too emotional.  Several of the others admitted that, at first, they were worried about that, too.  But that it got easier with practice and as they continued to learn more skillful ways to show up for their clients.  Especially as the other professionals in Jeremy’s deal were also learning these skills.  They each started to notice that Jeremy was sharing more openly with all of them and not just dumping all of his emotion on one person in the transaction. They didn’t have to wonder what was going on and the chaos and drama they’d been used to virtually vanished and everything got easier.

I told Amy how we had used, an intimate conversational-style dinner event, with Jeremy when we wanted to deepen his sense of connection and trust with the deal team.  We talked about how it created the conditions for psychological safety and how it transformed Jeremy’s relationship with us and ours with each other.

One of them shared that, although his partners had initially thought this approach was a bunch of hooey, as they learned more about what creating emotional safety for their clients meant, they realized that their clients actually seemed to crave that kind of deeper connection with them.  They started to see that the deals which had inexplicably fallen apart before had signs which now seemed obvious and fixable.

“Who knew,” I added, “such simple things could help clients bond to us and bring us into the fold as their most trusted advisors, the ones they come to early when they’re considering selling their business.”

Amy shared that she had been caught off guard a couple of times in the past year when clients of hers had sold their businesses and she only learned of it when the client was moving their accounts to a new wealth management firm.  She wondered whether some of these tools and experiences could help her strengthen the bond with some of her own clients.

Over the rest of lunch, we talked with Amy about the different ways we had learned to build trust with each other and with our clients and how it had radically changed each of our businesses.  She seemed especially interested in exploring whether she and her partners could learn how to do this with their own clients and the referral partners she had been trying to cultivate relationships with.

Lest you think we’re just a bunch of lazy bums with nothing else to do but lounge around over lunch or drinks, let me assure you that each of us have busy professional and personal lives, but we’ve seen just how important it is to create the ideal conditions for psychological safety and unshakeable trust for our clients and each other.

Our commitment to our client Jeremy in that deal ad beyond it has been to deepen our respect and rapport so that we can collectively be the safest nest for our clients in the future as we help them weather one of the most challenging transitions in their lives.

Guess what, since that lunch, two of the five of us are already engaged in a relationship with a new client together and that client is already sharing the kind of information that shows us he feels safe.  And every one of us is confident that this deal will close with ease.  As it should when an owner is surrounded by professionals who care about their client and each other

Most Advisors don’t believe me when I share they can
consistently close more deals with ease.

Then, they experience it for themselves.

Once you experience an inbox full of referrals and both you and your sellers expect a trustworthy sale process…you never go back to seeing the work as a numbers game.

Want to learn more about how YOU can find this same success with your clients and referral partners? 

Reach out – I’d love to show you how.

The Legacy Dinner is an intimate, conversational-style dinner event that helps you connect with your circles of influence and clients. Learn more about how best to utilize it for your business.

The post Do You Want to Know What’s REALLY Going on With Your Clients? appeared first on Denise Logan.

We talked about how we had each heard similar stories from friends at the gym and even celebrities seemed to be posting about their angst on our respective social media feeds.  

I remarked how lucky we are to have a name for what we were talking about “Empty Nest Syndrome”.  He nodded his head and said, “Yeah, I guess you’re right, that IS what we’re talking about, isn’t it?”

As you read on, I invite you to think about the similarities our owners face when they sell their business and how our familiarity with the emotional journey of launching our children can help you to care for your client through this very similar moment of transition when letting go of their business. 

While much has been written about how to survive empty nesting and we’re all familiar with couples who, once the children are “out of the nest”, look at each other and wonder “Who are you?” and “Do I even want to find out again?” or “What the heck do I do with myself now?” Many of those relationships don’t survive the existential challenges of reframing the relationship when caregiving for children and mutual parenting responsibilities lay bare what remains of substance in their relationship. 

The same is true for our business owners.  It’s not a coincidence that so many of them think of their business as “their baby”.  They birthed this business, nurtured it through troubled times and watched it grow. When faced with the time to let go and launch it into the world, they understandably experience this same emotional arc of letting go and the concurrent question about their identity without it. 

One of the things that helps parents process the innate sense of disorientation and sometimes surprising sense of emptiness is knowing that it’s perfectly normal.  That what they’re feeling is what tens of millions of other parents are going through in the same moment and that others have survived and gone on to thrive in their post-acute parenting time.  Most people around them recognize what they are experiencing as a normal part of letting go of their children and find support in their family and friends as they work through these feelings. 

What if, as advisors, we helped to prepare our clients for this same perfectly normal period of adjustment.  Instead of ignoring it, shaming them for their feelings or telling them they’ll “get over it” – recognize the transition that they are experiencing.  Bring to your client conversations an awareness of how you have navigated similar emotions when your children launched (or if you haven’t yet launched children, you can draw upon your own experience of the period of uncertainty when YOU left home, or had to leave behind a favorite coach or even sold a home and realized you were leaving behind the oak tree you had planted all those years before).  Come to the conversation with empathy and help normalize the experience, validate their fears, anxiety and worries.  Help your client to reflect upon how they dealt with the similar experience when their children launched (or they left a home they loved, etc.) Because most parents know that what they are experiencing is “empty nest” adjustment, we can laugh about it when we come to the table with one more plate than there are diners that night.  “Oh, that’s right, she’s at college.” We remind ourselves or know to gently comfort our spouse who remarks, “It’s so quiet here now.  I miss him.” Even though just weeks ago he was shouting up the stairs, “Turn down the music!” or “Why can’t you remember to turn off the lights!”  Oddly now we feel a little lost longing for those same things that annoyed us so recently.  If we didn’t know this was normal, we’d feel crazy. 

That’s exactly what our business owner client feels when she finds herself about to turn into the parking lot of the business she already sold, when she was actually headed somewhere else.  Her brain was on auto pilot, going to work was such a part of her routine.  Of course, it feels jarring to suddenly find herself in the parking lot where she no longer belongs.  She might feel embarrassed and hope no one saw her.  Or she might want to just pop in and say hello to her former employees.   

Likewise, the owner who was absolutely fed up with all the employees’ shenanigans and swore they wouldn’t miss it one single bit needs our compassion when the nostalgia appears and they question “maybe it wasn’t really all that bad” wondering if they made a mistake in their decision to sell. 

As parents, we remember that it was always our goal to raise this child and launch them into the world.  That this was what we were working toward and is actually a marker of our success as parents.  We kept them safe until adulthood (or this reasonable facsimile of adulthood!) and instilled in them the basics to begin making their way into the world.   Such is true for our business owners.  Their goal was always to build something successful and sell it or turn it over to the next generation, a means to harvest the wealth from their labors to fund their future or that of their family.   

But, then again, we experience the emptiness of the space in our home and in our routine that the now-launched child or business used to fill and find ourselves surprised by the depth of conflicting emotions and loss. 

We, and they, let go of the roles and routines and step herky-jerky into our new not-quite-so-clear and definitely less comfortable routines and roles.  We begin to discover who we are, other than Drew’s mom or Tory’s dad or the owner of XYZ Company.  Perhaps we pick up hobbies we enjoyed earlier in our life or had deferred because of our parenting responsibilities or realize we have no outside interests and feel ashamed and worried we won’t find anything to occupy our time.   

We try to navigate friendships that were forged with the parents of our children’s friends or with our employees and business associates. We discover those friendships drifting and realize that they were based on common interests we no longer share and question if those friendships were even real.  As empty nesters and former business owners, we are faced with the prospect of making new friends as adults and it can feel scary. 

Years ago, a close friend confided that she and her husband were thinking of having another baby since they missed their daughter who had just gone off to college.  I remarked, “But you’re finally free!” to which she replied, “It doesn’t feel free, it just feels … well … empty.  We loved being involved parents with our daughter.”  Sound familiar?  How many of your business owner clients dive right back into another business within a few months to avoid the emotions involved in forging a new identity?  Metaphorically, having another baby. 

Make good use of this season of launching to notice how you and the people around you are practicing the art of letting go and bring those lessons and that empathy into your work with owners all year long.   

I know I say it all the time but it’s true – it really IS a transition, not a transaction – and when we treat it that way, everyone wins. 

The post The Art of Letting Go: What Parents of College Freshmen and Business Owners Have in Common appeared first on Denise Logan.

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.

The post Building Your Courage Muscles appeared first on Denise Logan.

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 post Can This Deal Be Saved? The Art of Asking “What Matters?” appeared first on Denise Logan.

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.

The post Is Money Your Security Blanket? appeared first on Denise Logan.

Those four simple words and the answer they elicit could be a doorway into a meaningful conversation.  “About what?” I want to reply, but I know that isn’t the question he thinks he is asking me.  My thoughts were already falling back through time to the summer of 1998.

I landed in Bologna, Italy.  I planned to cycle.  Alone.  To slow down, enjoy the scenery and sort out what I was going to do next with my life shortly after a divorce from my husband/law partner.  No set plans, just a rough agenda of the areas I wanted to visit and a return ticket from Milan seven weeks later.  I was free for, perhaps, the first time.  It was exciting.  It was intimidating.  What have I done?  No schedule, no goal to reach.  Gradually, I eased into it.

Each day, I set my pace according to what caught my fancy.  Perhaps I saw an enticing cafe where I could while away the afternoon drinking Prosecco and enjoying the sights of passersby, making up a story about the handsome older couple walking slowly, heads down, like their frowns, but still holding hands.  My story drawn from what I could see, not so much what I overheard, since my Italian language skills were fairly pedestrian.

Another day, cycling on a red dirt road through a peach orchard, I was overtaken by the luscious ripe fragrance.  I decided to brave a little of my scrappy language on the farmer, whose door I rapped upon, and asked for a peach – with a lot of gesturing and smiles.  He filled the basket of my bike with those tender fragrant treasures and invited me to stay for lunch with his wife, who received me sweetly into a delightful farmhouse kitchen.  Didn’t need much language to display my appetite or my appreciation.  Let’s just say it was evidenced with gusto.

Over the next couple of weeks my language skills began to bloom a bit, as I had made it my business to try to learn ten new words of Italian every day.  Unfortunately, they didn’t always go together and I never quite mastered the art of conjugating verbs, but usually when “Me want juice” came out of my mouth, with the words “per favore” (please) and a full smile, me thankfully got juice!  I had begun to use my burgeoning language skills to acquire such things as an invitation to a Mozart concertina being performed by fabulous local musicians in the home of a newly made acquaintance from an inn I had stayed in.  What a treat to hear them play 17th century instruments!  They shyly bowed and then carefully stowed their instruments before accepting a glass of wine poured by the local vineyard owner, beaming over his own contribution to the pleasure of the evening.  They exchanged mutual admiration for each other’s talents.

I began to observe this interesting exchange again and again with people as I cycled from village to town and beyond, a certain respect for the offerings of each person to the other’s life.  It was even more obvious to me during a behind-the-scenes tour of an olive oil mill that a new English-speaking baker friend took me on.  The full-bellied olive mill owner, who was more than happy to pantomime words for me to help me understand all that he was gregariously explaining about his work, obviously loved what he was doing.  He called it his dance.  Not his work.  At first, I thought I had missed part of the conversation, but he explained that the way he coaxed the last drop of golden tantalizing oil from the olives was not by pressing them harder, but from engaging them in the dance of the mill, turning it round and round – just as he twirled me around slowly with my right hand in his high above my head, soon ending up wrapped in his gentle embrace with a peck on my cheek.  Ah, that explained a lot to me about what I was experiencing from him as he talked about his work.  It was as if he flirted with his work.

The baker had brought along a focaccia to share with his olive mill friend and me.  Before long, I found myself on a tour of local craftsmen and women in the town – each contributing a little morsel to my understanding of their local economy.  The farmer who grew the local wheat and red peppers in my tasty focaccia.  The olives topping it were from the same grower from whose olives the miller had created the oil.  Next stop, the cheese maker, disappointed that he couldn’t leave his little shop to take me personally to meet the owner of the cows from whom he acquired his milk, but assuring me it was always fresh and warm when he brought it home, which is why the cheese was so sweet and milky (decidedly unlike the hard, sterile shrink-wrapped Polly-O available in stores at home!)

Again and again, each of the many people I met along this afternoon journey by bicycle with my new friends, many of whom joined our little bicycle caravan to continue on to the next stop, touted the contributions of the others to the item they could easily have claimed as their own sole priceless creation.  Nope, this was a community of interconnected people, each fully engaged in the work they were doing, and nourished by the gifts of the other producers around them.  The olive grower saw himself as part of the miller’s business and of the baker’s and of the cheese maker’s.  Interesting.

Just as curious to me was how they spoke of their work.  They never called it work.  They used precious words of affection for what they were doing.  They called their peppers their “bambinos”, they called their cows their “darlings”, the miller called his mill his “old friend” – as in “my old friend and I dance our way into the hearts of the olive jewels”.  I loved how quaint this was, the people so engaged with their work and each other.  I chalked it up to village life.  Secretly, a part of me wanted to stay wrapped up with them and their pleasure.  I ached for it as I saw slivers of this connection to passion nearly every place I cycled.

Mid-way through my trip, I cycled to the ferry that took me to Venice, a bustling city that soon had me feeling more like my busy self.  I phoned back home from my hotel room and spoke to my office manager, checking in on what needed my attention after nearly three weeks away.  I was soon ensconced in my personality as an important lawyer again.

That evening, as I stepped out of the canal boat on my way to dinner, a little storefront window with a display of jewel-toned marionettes caught my eye.  My fingers wanted to touch the delicate rose brocade of the jester’s hat on the one closest to the door.  Passing through the narrow doorway admitted me to a shop laid out like a railroad house, a single narrow hallway with staggered rooms opening off the left and right all along the corridor.  Each room beckoned with handmade treasures that made me let out the involuntary sound “ooohh” as I reached out to touch an iridescent plum colored hand-blown perfume atomizer or a bronze and burnished copper sculpture mounted on a slab of veined green marble.

It was that sculpture that led me into conversation well beyond my language comfort with the sculptor who emerged from a room of laughter at the back of the shop.  She had a slender cylinder filled with limoncello in her left hand as she approached me.  How lucky to get to meet the creator, I thought.  I wanted to know more about the piece she had created and what the title card meant.  The piece stood about 18 inches high and 7 inches wide with a clock face mounted in the center.  Above the clock face, the bronze transformed into a spray of birds in flight, below the clock face the bronze and copper melted together and blended into a pile of tarnished copper and gold coins, with modern and ancient values embossed upon them.

She translated the words on the title card for me “il tempo e denaro e come si vola” … time is money and how it flys.  I had to have it.

She wasn’t done with me yet, even after I made my purchase.  As I followed her into the back room into the midst of laughter and overlapping conversation coming from the nine men and women gathered around a waist-high worktable covered with various ongoing projects, Nina introduced me as her new American admirer.  A salute of limoncello-filled drinking vials welcomed me into their midst.  And that is where I spent a good part of the next two weeks, building friendships with a collective of artists who had come together to share space, create and showcase their works.  I expressed appreciation for the intricate skills they each displayed – the marionette maker with her fine beading detail on the costumes.  “No,” she told me, “the costumes are made my Antoine, I only breathe the life into their strings and faces and hands and feet.”  The costumed jester made its way home to my niece.  Each of them, in turn, shared bits of their passions with me – how their work was not separate from that passion or from the heartbreak of their lives – but woven all together.

They were amused with my answer to their question, “What do you do, Denise?”  Because their English was still growing, as was my Italian, I answered, “Io sono una avocata” (I am a lawyer).  Donato chortled out the translation from Mariana’s quick outburst. “No,” he chided me, “they don’t want to know how you earn your money.  They want to know what you do that comes from here.”  Pointing to his heart.  Oh.  That.  Hmmh, more stammering on my part.  They chalked it up to my weak language skills.  Me, too, except that I knew the language I wasn’t quite fluent enough in to answer their question wasn’t Italian.  It was meaning.

I brought back with me many of their precious made-by-heart treasures.  But the gift I treasure most is the question they asked that still moves around inside of me.  What do you DO?

For years now, each time I hear someone ask that question, to me or I overhear someone else being asked it, I realize my own heart is listening for the answer.  My ears may hear, “I am a doctor, banker, plumber, dentist …” but my heart is always hoping the answer will come from deeper within the person answering the question.  Something real, like “I give children more time with their grandpa” (the heart surgeon) or “I provide shelter to women who would otherwise be at risk for the sex slave trade” (the banker financing companies who pay living wages to workers) or “I make sure tradition stays alive” (the plumber who works on Thanksgiving Day at no extra charge) or “I help rebuild young men’s self-esteem” (the dentist doing implant work for refugees once a month).  By the way, those are actual answers that have come from the mouths of some of my clients as we’ve explored their questions about work.

I adored being in the company of my many friends there in Italy and they tried mightily to persuade me to stay and become their English-speaking business manager.  For a long time, I regretted coming back home.  Not anymore, because I have a real answer to that question now.  Ask me, I’d love to tell you and to help you find yours.

The post Whaddyado? appeared first on Denise Logan.

On the day I got married, I had a few blessed hours alone before the hubbub of the day began.  Given that I am bent toward reflection, I went for a meditative walk along the Potomac River.

Contemplating what lay before me that day and stretching out into the future, I noticed the fullness of the trees.  I can’t recall what type of trees they were now, but the branches spread wide and there were thousands of leaves offering shade as I lay in the grass beneath them, enjoying the slight breeze.  As I gazed up, glimpsing sky between small patches in the canopy, I thought about all that had transpired for these trees to become their majestic selves.

Two trees arched across the expanse of lawn, their farthest branches just beginning to intertwine to create an expansive canopy together.  Seeds planted long before had germinated and grown into a family of trees.  One that was about to join with another.  Symbolic.  Just like in my own life.  “A family tree,” I thought.

In the quiet of that morning when I returned from my walk, I sat at our dining room table and wrote a series of letters – some I mailed, some I tucked away to deliver later.  They contained my perceptions of the seeds and fruits and shades of legacies which had come before me.  I wrote one to my paternal grandmother, the oldest living member of the lineage I came from.  Another I wrote to my parents, at that point married 25 years.  One was for my husband’s parents.  Those I actually mailed.  I walked to the mailbox on the corner and held those letters close to my heart and then to my lips before I dropped them into that familiar blue box, imagining what those closest to me might think or feel when they read the words I had penned to them on that special morning.

Several others I did not mail.  I hand delivered to my husband the one I wrote to him.  The ones I wrote for the children I hoped would survive us, but never did, remain unopened still.  Others that were for relatives who, at that point, were already long gone were left graveside over the years or dropped into a mailbox somewhere without an address, stumping some poor postal worker while they sat unclaimed in the undeliverable bin.

What was in those letters?  My perceptions of the legacies that had been handed down to (or sometimes foisted upon) me, intentionally or otherwise.  Some words of praise and gratitude, some unanswered questions and dismay.  Some values and beliefs that I was giving back to those who handed them to me in words or deeds or silent mysteries I couldn’t quite recall, although I certainly felt their weight.  But those letters also contained words of love and of hopefulness for my future and for theirs and some statements of intention – my own legacy in the making.  Things I didn’t want to go unspoken.

Close to three decades and more transitions than I could have imagined have passed since that September morning in Virginia.

The Making of a Legacy

We have just passed out of the term of one President and into the term of a new one.  With this transition, there has been much talk about what each President’s legacy will hold.  What will be the marks of significance for each man?  As I have listened to the talk of legacy these past several weeks, I wondered what the people close to me would say their legacies are, whether they line up with my own perceptions and, of course, what my own legacy will be?

Tangible or Intangible – Which Legacy Have You Been Focused On?

So often the conversation around legacies is limited to only the tangible goods or wealth that are passing from one generation to the next.  In fact, some of the greatest wealth we can transfer comes with our stories of meaning attached – our values, beliefs and aspirations and how they were formed and carried out.

Our wisdom develops as we integrate the traditions of our families and cultures, blended with our own principles, values and beliefs and tempered by our own experiences.  The garden that succeeds us inevitably comes from the seeds we have planted and watered with our actions and our words.  Our children, our peers, our communities are watching us as we tend the gardens of their futures.  They are the recipients of our legacies, both intended and unintended, whether filled with glorious blossoms of congruent attention or the bushy weeds of neglected values.

Passing along the intangible parts of our wealth is an equally essential part in the planning of our legacies and what we bequeath to those who live beyond us – in our families, our workplace and our communities.  Those seeds take root or fall on hardened parched ground depending upon your words and actions every day.

The impulse to communicate what we think matters is as old as time.  Centuries ago, instructions on how to live a life that matters were handed father to son, mother to daughter.  Now our focus is on ensuring they receive the goods.  Important planning, to be sure.  But, if you were not here tomorrow, what is the most important thing you would not want left unsaid?  What would you want your loved ones and colleagues to know and have in writing, to reflect on and to cherish?  The reach of your words and of your actions, as the intangible part of your legacy is unknowable.  Are you incorporating this other part of your legacy into your wealth transfer planning?

How Do You Want to be Remembered?  Has Your Life Been Significant?

Starting with this question “How do I want to be remembered?” opens the gate to the garden where you will plant the seeds for living your life as if you matter.

In a prior column, we considered the questions: What is important to you?  What are your values?

I invite you now to ponder: How do you want your life to touch others?  What would make you proud?  If you had to do one thing to improve your world, what would your contribution be?  How can you increase the well-being of those who depend upon you?  How can you leave your mark on whatever you do?  How has your life mattered?

The answer to these introspective questions will help you develop a meaningful philosophy of life that goes beyond just creating financial wealth.  Your words and your actions are the building blocks of your legacy.  Knowing what’s important, what drives you and how you want to be remembered creates tremendous clarity in how you should live your life.  In fact, it IS the measure of your significance.

Leadership’s Role in Your Legacy

“A leader’s lasting value,” leadership expert John C. Maxwell says, “is measured by succession.”  What are you doing to develop the leadership pipeline in your company and in your family?  To ensure your legacy lives on?

Develop a plan that not only passes on your tangible wealth, technical mastery and knowledge but also your wisdom and your leadership philosophy.  Teach people about creating lifelong customers, balancing profit with ethics and doing well while doing good.  These lessons are some of the most valuable teachings you can pass on to equip your company’s leaders to carry the torch into the future.

What Would YOUR Letter Say?

Think about what you would say if you had time to write just one letter?  To whom would you address it?  What would you include?  What would you leave out?  Would you chastise and rebuke?  Would you thank, forgive or seek to instruct?

Your legacy is as much in your words as in your actions – a legacy that you leave for your children, your family, your friends and associates.  I’ve worked with hundreds of men and women to craft their own letters.  Think of it as an important document which captures the essence of who you are and what you stand for by writing about your life lessons, values, accomplishments and hopes.  It’s a way of recording significant milestones and defining moments in your life, something you leave for those who matter to you.  And which guides you as you continue to live.

Success, Significance and Legacy

To be certain, you can be successful without having a significant life, but success without significance is hollow.  A legacy of significance transcends one’s lifetime, influencing the lives of generations that follow.

We will all leave some sort of a legacy, even if we did not plan for it.  Our legacy may come in the form of our children, a business we can pass on to others, or an estate that we leave behind.  It also comes in the form of caring words and actions that bring your wisdom and values to life long beyond when yours ends.  It really is a choice you make, day by day.

There is much talk about what the new President’s legacy will look like.  Of similar significance is the question “What will be yours and how will you pass it on?”

The post Legacy as the Measure of a Life of Significance appeared first on Denise Logan.

*****

“When we close these next two deals, then I’ll have the financial security I need to be able to leave and retire comfortably.  I just need to see this thing through.  I mean, it would be foolish to leave without bringing it through the goalpost at this point” said Vince.  Meanwhile, while he waited to get these two deals through the closing process, he was continuing to actively advance other relationships and areas of the business that would make it likely he would repeat this “just one more thing …” cycle he seemed to stay stuck in.  He had confided some months earlier that his closest friends had begun prodding him, because he always had another thing he needed to finish before he could contemplate leaving.  To anyone observing his behavior, there was no evidence that he was ever planning to leave.

Marion was on the same path as Vince.  She had repeatedly told her family she could slow down and take some time for herself once the kids were through college.  But now two of the four were signaling their desires to pursue advanced degrees and, instead of downshifting as she had planned, she was about to begin an arduous fundraise that would likely commit her to another several years at this harried pace she had long ago become accustomed to, despite the toll it was taking on her and the many years it had kept her from exploring her own interests.  Although she had set several markers for herself that when THIS thing happened, she would leave, she still hadn’t.  Each time, she set a new “when THIS happens …” for herself.  She often complained, “When is it MY turn to enjoy my life?”  Yet, still she labored on, doing exactly what she’d done for decades in the business, with no real plan to change while life continued on without her.

Jackson’s plan had always been to transition the family business to his sons, but each time they approached him for more responsibility or to begin effecting the transition, he told me he wasn’t sure they were ready.  I finally told him that I thought HE was the one who wasn’t ready – they had long ago, and repeatedly, proven their capabilities at running the business.  He just couldn’t seem to get himself to let go.  In fact, he seemed to sabotage their efforts by refusing to bring them into key relationships, making customer agreements without involving them and keeping everything in his head, effectively stonewalling an active transition.  One son had finally drawn a line, either Jackson began participating in a transition with a definitive end date or he’d leave and start a competing business.  He wasn’t waiting any longer.

What do these three clients all have in common?  A pattern of setting and resetting markers for their transition out of their business and into the richness of their well-earned, and long-anticipated post-work life.  If you asked them, they’d tell you they were looking forward to retirement and enjoying their success.  But they were each deploying a recurrent pattern of delay.  Repeatedly, they would say, “When THIS happens, THEN I’ll leave.  I’m sure of it!”  Only to find another reason to stay.  Often citing needs for greater financial security, an unwillingness to leave while something is pending or fabricated uncertainty in the capabilities of those who would take over when they leave.

It doesn’t matter if you’ve just made a huge windfall in your 30’s, turned 50 and hit your original financial “freedom” goal or are nearing 70 and have achieved the external markers of success.  Leaving is harder than it looks.

WHO AM I IF I’M NOT THIS AND WHAT WILL I DO NEXT?

I often call my clients the “What’s Next-ers”.  Make no mistake, the process of leaving something you have known takes preparation.  Even when you’ve been looking forward to the day when you have enough saved and can take it easy. It’s hard to leave. Doing it actually takes some strategy, some innovation and some courage.

It’s not an uncommon experience among high achieving professionals whose self-esteem and very identity has become blended with their careers or businesses.  Under it is a fear that their sense of importance will falter.  As one client put it to me “What will I do when no one seeks me out for my advice or wisdom anymore?  Who will I be important to?”  He had become accustomed to being called off the golf course for “urgent” business matters that only he could solve.  The thought that wouldn’t happen anymore was, frankly, terrifying.  Another confided, “I just can’t imagine what I will do with myself with all that free time.”  Others have told me that they couldn’t stand the thought of that much time with their spouse, after all these years of living their independent but essentially estranged lives while work and children had occupied their respective time, except for a few weeks of vacation interspersed throughout the year.

“NOT ME!  I’M LOOKING FORWARD TO THAT DAY!”

Typically, when I talk about the difficulty most people have in leaving their jobs and transitioning to retirement, my listener will tell me “That’s a high class problem to have!”  They frequently assure me that THEY will have no problem leaving their business or career when the time comes.  When asked when that day is scheduled to occur, most answer “When I have enough.”  Although when pressed, nearly everyone isn’t quite certain what “enough” will look like and financial advisors regularly confirm that the closer their clients get to the number they originally set, the more likely they are to add a zero or a multiplier, continuing to worry about whether it will, in fact, be enough.  So they often keep working long past the time they thought they would.

When I’ve gotten under that initial “enough” question and ask what they will do in their retirement, more than two-thirds of respondents tell me they will travel and/or play more golf.  Of course you will.  Perhaps for a year.  Or three.  And, then, you’ll want to be doing something else with your time.  Something that feels like it matters.

When asked for the list of places you’ll travel to, how long you’ll stay and what you’ll do there, most answers fall flat – stuck in the standard “oh, lots of places!”  Most of these folks I’m talking to have rarely, if ever, taken an entire week off completely unplugged from their office, email or cell phone, let alone an extended vacation of a month or (heaven forbid) six months.  Travel as a retirement goal will only take you so far into the future.  At some level we each know it, so we keep working, uncertain of what’s next.

I’m reminded of an attorney I was guiding in his career planning.  He was a partner at a law firm that awarded all ten-year employees with a paid six-week long sabbatical.  He was contemplating changing firms before the ten year mark because he was terrified about what he would do with six consecutive weeks off.  Eventually, I talked him off the ledge and we found enough interesting things for him to do with his sabbatical; though he did not stay with the firm through his fifteen year anniversary, when the sabbatical increased to three months.  If was too frightening for him to even contemplate – instead, he left a perfectly fine career at a firm where he was rewarded and respected to move to a firm that had more standard vacation benefits which he could tolerate.  I watched the lead-up where he terrorized himself into a job change, all couched in language about how we wasn’t being compensated well enough.  Not true, he was scared to death at taking three months off.  In his mind, he’d go crazy with that much time off and he was afraid he’d become dispensable and easily replaced.

Before you say, “Not me, I’d embrace that gladly!” ask yourself this – what are you doing right now to make it possible to take a six week unplugged sabbatical in the next year?  Perhaps even between jobs or deals.  If you tell yourself that is completely unrealistic, I’d challenge you to a call with me to talk about how to make it realistic.  I’ve done it and so have many of my clients.  In fact, it’s good preparation for an actual transition out of your business or career later (whether you think that transition is two years or twenty years from now) and it will teach you a lot about how to plan for the real deal.

What else will you do with yourself when you retire?  Sometimes the answer I hear is that you will do some angel investing or help some small companies in which you can take a stake and keep generating income or you’ll consult.  Other frequent responses are that you will teach some classes on entrepreneurship or investment strategy as an adjunct professor or sit on a board of a community or non-profit organization.

These, too, take some planning and preparation.  You’re not likely to simply leave your work and be asked to teach, guide businesses or sit on a board right away.  Some planning to explore and line up these options is in order in the years leading up to your exit.

All of these options are good ones.  Most of the people who utter them to me actually want to do these things, too.  But few of them actually will.  Most of them will simply keep working at their jobs, long after it makes sense to leave, convincing themselves that they just need to garner a little more cash, bolster their retirement assets, or any of a hundred other seemingly legit reasons to keep doing what they’re scared to leave since they don’t have a tangible thing they’re going TO.

One client put it succinctly, “How can I leave my safe but-not-so-satisfying life when I’d be headed out to sea, completely adrift?  At least, if I had a framework of the new thing in place, then I’d feel safe in leaving.”  Did you recognize the “If this, then that” dialogue?  I did.  Especially since I’d watched him refusing to transfer responsibility to his staff, continuing to enthusiastically invest the bulk of his energy in the ongoing development of the business he said he wanted to leave – all the while keeping himself from devoting energy to the supposed framework he claimed he needed to be securely in place before he could leave.  I recognized it for what it was.  Delay.  And so, I challenged him, to set clear defined markers he was willing to stick to and to identify the tools he could use to keep more “if this, then that” delays from creeping in and stealing his life away.  We’re working on it, defusing his fears and keeping him accountable.

It’s not easy work to leave.  If it was, you’d do it.

WHY IS IS THAT YOU KNOW HOW TO CREATE AN EXIT, YOU JUST DON’T KNOW HOW TO LEAVE?

It’s because you don’t have a plan.  No, I mean a REAL plan.  Someday is NOT a plan.

The companies in which you invest have a life cycle.  If you are an investor, you know when the company needs more money than your investment strategy calls for, you will exit.  You will prepare the company for the market and you will pass it along to the next investor or take it public.  When you enter the deal, you have some pretty clear ideas of what it will mean to let go and exit.  You have a plan.

While you may miss the time you spent with a particularly engaging leadership team, your colleagues on the Board and even the co-investors in the deal, when the time comes, you will let it go.  You would never think to say, “Just give me a couple more Board meetings, ok?  I’m not ready to stop hanging out with you and I’m not sure what I’ll fill this time with going forward.”  At some point, you know it makes sense to shut it down or sell it.  You don’t hold those companies for endless decades.  That’s because you have a plan and you set clear defined markers to help you exit and you prepare your portfolio company for what’s next.

Likewise, when your children are born, hard as it is to imagine at the time, you know there will be a time when they must launch into the world and enter adulthood and your relationship with them will change. For some it will be easy, for others, launching takes longer.  But, almost no (healthy) parent I know endlessly resists the process of preparing themselves and their child for leaving.

You begin early to equip your teen with the skills and resources necessary to leave the nest.  Even those who are anxious typically begin to step forward toward their exit when they can begin anticipating “what’s next”.  Loving parents don’t simply make an abrupt transition and assume their children will know what to do in this next stage on the day they turn 18.  The prepare their children for months or years in advance so they can begin this transition, providing connection and mentorship as it takes place over time.

The reality is that the reason your portfolio companies and children launch is because you have a plan and you have established markers along the way to ensure they are ready for the transition.  Your career transition needs one, too.  Successful transitions happen gradually toward “what’s next”.  Abrupt transitions are scary and unnecessary.  And, contrary to what you might think, sorting out “what’s next” takes some planning and a good guide can help you navigate the terrain, even years before you’re at the doorstep.

Make no mistake, this is as emotionally unsettling for a 35 year year old who hits it big and cashes out early as it is for a 54 year old whose firm makes unexpected layoffs or a 68 year old who is contemplating retiring after a satisfying career.  And, what you’ll do with yourself doesn’t suddenly get clear on the day you reach your magic “enough” number that your financial plan says marks when you can retire.

You’ve been meeting with your financial planner for years, relying on his or her guidance as you set and adjusted the milestones for your exit.  You wouldn’t dream of leaving the financial piece of your “What’s Next?” plan to chance.

Aren’t you worth the same care you give to your children and your portfolio companies?  I think so.

Why not give yourself the same mentorship, even if it’s just a quarterly check-up, on the practical and emotional aspects of your “What’s Next” plan.  Call me and let’s have a little chat.  I promise you, with a little boost, you’ll look back on this launching pad into the next part of your life and wonder what took you so long.

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