If This, Then That – The Key to a Successful Exit
Denise Logan

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.


“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.


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.


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.


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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