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.

***

CLOSING THE BOOK ON 2021

1. What did I embrace in 2021?
2. What did I let go of in 2021?
3. What changed for me in 2021?
4. What did I discover about myself in 2021?
5. What was I most grateful for in 2021?
6. When did fear hold me back in 2021?
7. Where did I demonstrate courage in 2021?
8. What surprised me in 2021?
9. What made me smile in 2021?
10. What were my 3 most significant accomplishments in 2021? For each, list the following:
    1. The skills that helped me to make it happen
    2. How my life changed because of it
    3. What I learned about myself
    4. How did I celebrate/acknowledge (or, if I didn’t, how can I do it for future accomplishments)
11. What were my 3 most significant challenges in 2021? There may be more than 3, use the ones that come to mind first.  They may have tested my limits, my patience or may be big or small.  For each, list the following:
    1. How did I deal with this challenge
    2. What new tools or allies did I uncover that I could use in the future
    3. How did my life change because of this challenge (even if it’s not yet concluded, what would feel good from the challenge in the end)
12. What was my favorite moment of 2021? (Get in touch with the sights, smells, sounds, who was or wasn’t there, what was I doing, what made it amazing?)
13. What were the gifts from 2021? What really stands out and mattered to me?
14. Is there anything from 2021 that I need to still let go of, say goodbye to or forgive myself (or someone else for) or just need to empty onto the page?

Summarize 2021 in 3 words

***

OPENING TO THE STORY YET TO BE WRITTEN FOR 2022

1. What am I looking forward to in 2022?
2. What am I feeling apprehensive about for the year ahead?
3. What life lessons am I taking into 2022?
4. What area of my life do I most want to develop in 2022?
5. What part of myself do I long to nurture in 2022?
6. Fast forward to December 2022.  I’m sitting in a café, musing over the last 12 months, where do I want to be …
   1. … in my work and wealth
   2. … in my relationships
   3. … in my free time and my sense of meaning
   4. … in my body and my home
7. 3 unhelpful beliefs I’m ready to release
8. 3 duties or commitments I’m ready to let go of
9. 3 interests, skills or hobbies I’d like to learn or improve
10. 3 things about myself I positively love
11. 3 ways I could be kinder to my body this year
12. 3 dreams to bring to life this year (personal or professional)
13. How can I bring more of a sense of calm and grounding into my life this year?
14. My secret wish for 2022 is …

My Blueprint for 2022:

This year will be the year I finally ….

I will nourish myself with …

I will make more time for …

I will recharge my batteries by …

I will open my heart to …

I will pay more attention to …

I will learn more about …

I will release my attachment to …

I will say no to …

I will say yes to …

And, because of this, in 2021, I will feel …

I fully believe in the possibilities that await me in 2021 and all that it holds for me.

Signed: _______________

***

The post Reflective Questions to Contemplate as You Turn the Page 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.

*****

“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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