Episode 44: Navigating life’s biggest transitions 

Oscarlyn Elder:

Major life transitions can affect us in ways we don't always expect. Maybe it's selling a business, becoming an empty nester, retiring, or the death of a loved one. Even when those changes are planned for, they can still disrupt our routines, our relationships, our sense of identity, and the way we make decisions about our money. I'm Oscarlyn Elder, head of investment management at Truist Wealth, and this is I've Been Meaning To Do That, a podcast from Truist Wealth, a purpose-driven financial services organization. I appreciate you listening. Today we're talking about how to navigate major transitions thoughtfully and intentionally. My guest is Dr. Sherry Walling, a clinical psychologist, speaker, and author of Exit Strategy: The Entrepreneur's Guide to Selling Your Business Without Regret. Much of Sherry's work focuses on business owners navigating transitions, but the ideas we'll discuss today apply much more broadly to anyone moving from one major chapter of life into another.

Sherry, welcome to I've Been Meaning To Do That.

Sherry Walling:

Thanks so much for having me, Oscarlyn. It's wonderful to be with you.

Oscarlyn Elder:

Well, let's get started. We both know that many successful people, they're definitely used to being in control and overcoming challenges. Why can major transitions still catch them off guard emotionally?

Sherry Walling:

It's such an important question. I love working with high-achieving people. They are such amazing humans, and one of their superpowers for most high-achieving people is the ability to forecast into the future, to make plans, to execute on those plans very effectively and to be able to just kind of anticipate what they want their life to be like two, three, five, 10, 15 years down the road. But the thing that successful people don't often account for are the non-goal-oriented aspects of transition, which is just how it's going to feel when everything that you built is changing. And when we really index for outcome orientation or goal orientation, it can be extraordinarily uncomfortable for high-achieving people, again, when the things that they have built begin to shift. And so one of the things that's really important to keep in mind is just the emotional quality of loss.

Even really great changes involve loss, involve the loss of the life that you had, of the person that you were, of the way that you operated in this previous version of you. So selling a business, sending a kid to college, going through a divorce, going through a transition in your business partnership, all of those things can be wonderful, but they involve a losing and a letting go of something that you built, which is painful and hard and unexpectedly emotionally challenging.

Oscarlyn Elder:

So that letting go, if you will, that actual transition, the loss is often what folks are processing sometimes after they've gotten through the transition, because maybe during the transition they may not have enough time or space to even process it in that moment.

Sherry Walling:

Yeah. Such a good point because a lot of these transitions take a lot of energy and time. If you think about getting a business ready for an exit process, I mean, you are in the weeds of the spreadsheets of your business, and you're thinking about the deal points and you're negotiating with lawyers; you're going to lots of meetings. The demands of that process are so absorbing of your time and energy that you don't have much emotional bandwidth to do the work of like, "How is it going to feel when I don't go to this office anymore? How is it going to feel when I don't sit around the conference table with these people anymore? How is it going to feel when I'm not the president, CEO of X company?" You don't have the bandwidth to do that until you're on the other side of the exit.

And sometimes it can kind of really sneak up on people and hit them like the sudden stop of a ... when a train engine stops suddenly and all of the adjacent train cars sort of pile up and push against the engine. I think it can feel like this accumulation of emotional energy that hasn't been tended to and be quite disruptive for people when it kind of all comes to a head.

Oscarlyn Elder:

Help us understand what makes major life transitions feel different from other difficult decisions that people make in life or in business.

Sherry Walling:

I think major life transitions often involve a shift in the identity of the business owner or the entrepreneur. We make lots of choices every day, and some of us make lots of big decisions in our roles, in our family lives and our jobs, but the bigger the transition, the more that it involves a shift in our identity and requires us not only to do something different in our day-to-day life, but to see ourselves differently. And that's a surprisingly tricky thing for humans to do.

Oscarlyn Elder:

So if your identity is wrapped up in the business or in, I'm thinking also of a number of friends who have sent children to college, right? And so they're beginning to grapple with empty nest life, if you will. But is there something that we can do to actually make it easier for us to envision or create that new identity?

Sherry Walling:

Yes and no. I mean, number one, I do think that it is an important part of a transition to just go through the hard stuff, to give ourselves the space to grieve the loss of a business or the loss of a child living at home. And that's, I guess that's not really a sexy message. It's not a thing that people ask for, but it is actually a thing that people need, and that is to allow the emotional quality of loss some space in your lives. It doesn't mean you have to sink into three months of depression, but it does mean that you have to tell the truth about what is hard and what hurts and the way that your life will look quite different on the other side of the transition. And I think when we do that, when we grieve, then it's almost like we're clearing space, we're clearing out some closets so that we can begin to reimagine what does it look like from the mid of my life when I don't have children that I need to feed every night.

Look at all of the social opportunities that open up to me. Look at all of the legacy projects I can be involved with. I can get a new hobby. So it's once we tell the truth about the loss that we can create some space for the new opportunities that are presented with this new version of our lives.

Oscarlyn Elder:

And what are some signs that folks may be struggling with this identity shift in a transition process?

Sherry Walling:

I work with one gentleman who was getting ready to sell his business and had an offer in process, and before that deal closed he bought another business. And the business that he bought was kind of like a reaction, like it wasn't really a business that he had deep expertise in. And the more that I spoke to him about it, he really wanted to prove that he could do it again. And that kind of flags a few things for me as a psychologist because it wasn't really a good business move. He didn't think it through and gave himself no space to rest or grieve or settle or regroup, to really be thoughtful about what he wanted the next phase of his life to look like. So I guess that's one red flag is when you see reactive responses. Another problematic pattern would be absolutely minimizing the effect of the change, like just sort of assuming that everything will go on.

This is the person who has sold the business and maybe has stayed on in their businesses in an advisory capacity, but is still going to the office every day even though they don't have a job there; they don't need to be there. So it's really a clinging to the past and the past schedule and the past set of assumptions. It's just a, we're going to continue on in the same patterns and really refusing to acknowledge that there's been a transition.

Oscarlyn Elder:

So these major transitions, Sherry, how can they start to affect family relationships in ways that perhaps the high achiever may not be aware of?

Sherry Walling:

There's quite a bit of data to suggest that these transition times are a really high-risk time for long-term marriages or long-term partnerships, and that happens for a few reasons. One is that the transitions themselves are quite stressful, and so there's a lot of emotional burden, as we mentioned, just getting through the transition. The second is that people respond to grief and loss quite differently. So for the example of a kiddo going to college, you might have two parents, one of whom who is like, "Woo-hoo, I've been waiting for this moment. Time to travel, time to party, time to hang out with my friends," and is kind of having like a retrospective experience as a 20-year-old, and then you've got another person in the same partnership who really doesn't want to move on and wants to keep kind of hyper-parenting their college-age child.

And so the difference in those responses can of course create quite a lot of strain. And one of the things that's so important in these transitions as much as possible is that people in a couple or in a family are really actively talking about the transition. What are our shared dreams now that we're not parenting young kids, or what are our shared dreams that we're not running the business? It's a bit of the conversation that people have about retirement. Now that our schedule and our lives are going to look quite different, if we want to continue on together, how do we proactively make sure that we have some things to talk about and some things that we want to do together and also bring in other relationships with friends and other family members so that people are not relying solely on their romantic partner or their marriage partner as their source of understanding and connection.

Oscarlyn Elder:

So what I'm hearing you say is there was a journey, and creating that next chapter also requires some pre-writing, if you will, if we're going to talk about chapters. It helps if you've thought about, with some intention, how that plot's going to develop, if you will.

Sherry Walling:

Yeah. You're highlighting something that's so important, which is that high performers tend to be pretty high-intensity people. These are people with a lot of energy, a lot of drive. This is not somebody who watches four hours of TV a night, right? This is somebody who's like, "I'm up in the morning, I've got energy, I’ve got something to do." And so helping people mindfully redirect that energy is a very important part of this process. So this is where we think about board work, we think about legacy projects, we think about doubling down on a really interesting hobby that someone can throw their energy into in a way that is productive and healthy for them.

Oscarlyn Elder:

Well, Sherry, something stands out in this conversation to me is that transitions don't just change someone's circumstances. They can affect the emotions, the relationships, and the way a person makes decisions. Let's talk about how transitions affect our judgment when we come right back.

Dr. Sherry, in your book, you talk about transition fog and the effect uncertainty can have on people. What does prolonged uncertainty of the kind we might feel during a long or important transition do to our thinking and decision-making?

Sherry Walling:

Yeah, decision fatigue is real, especially in these really prolonged experiences. This became really alive for me. Part of the writing of this book came from my relationship with my husband, Rob, who sold a software company a few years ago. I'm a clinical psychologist; he's a software dude. And so I'm watching my kind and generous, wonderful husband. I married the best man, but I'm watching him through the course of this exit process sort of turn into this paranoid, sarcastic, like compulsively reading the line by line of the contract over and over, trying to figure out how the acquiring company was attempting to screw him out of money. And I was like, "Who are you? Who are you? Also, we have lawyers for this." But I think one of the things that he was experiencing, to speak to your question, is this idea of just decision fatigue of so many data points and so many small decisions, all of which have big implications.

And for some people, they really lean into the details of decisions when they're under stress. They become more rigid, and it's in that rigidity that you see anxiety really take root. So let's call that a rigid reaction to decision fatigue or to transition fog. Some people go the other way, which is to get kind of chaotic, like they're not reading anything. They're not coming to the meetings. They're losing their car keys. Their mind is all over the place because they're having trouble really settling down and sinking into the decisions at hand. And so someone can go chaotic; someone can go rigid. It's just kind of like our preferences when we're under stress. So however we are leaning in these decision processes, an exit process or a big transition just puts a lot of pressure on those tendencies.

And so it is really important to have some self-reflection or to be working with a coach or a therapist or be in a mastermind group or have some other external person who can very gently say, "Hey, you're doing it again. You're doing the thing again where you get really rigid and cynical, or you're doing the thing again where you're like really struggling to focus. So let's slow down the process."

Oscarlyn Elder:

I think my family, when I get into one of those states, it may not even be a major life transition. It may just be an intense work environment. They're like, "Hey, you need to step it down." So they often are not overly gentle with me.

Sherry Walling:

But they love you.

Oscarlyn Elder:

They know and love me, and they know that I will hear them if they are like, "Hey, time out. You're doing it again." But having that external force that hopefully can bring you back to center in some way helps make you reflective.

Sherry Walling:

Yeah. And often it's a theme, especially in the case of leaving a business, you need a variety of people. You need a wealth advisor, you need a lawyer, you need an accountant. Often having a psychotherapist or a coach or somebody who can kind of help you through the mindset shifts, and that's, I think, one thing that has felt really important in the writing of this book and having some of these conversations. We're very social humans. Even introverts are social creatures, and so we understand ourselves in the context of the community in which we operate. And so having advisors and trusted people around us who are helping us rewrite our lives is extraordinarily important.

Oscarlyn Elder:

When people are going through a major transition, where do you most often see people make decisions they later regret?

Sherry Walling:

These transitions really call forth our money psychology. So whatever our relationship is with money gets really pressed on and exaggerated in the context of an exit. So the person who runs out maybe before the exit's finished and buys a new Porsche versus the person who keeps driving their 25-year-old Toyota despite having $100 million in the bank. There's the dysregulation that we have about money and our own psychology and beliefs about money and its purpose in our life. All of that really gets triggered and comes up in an important way around these kinds of transitions. And so I think any of these big purchase decisions that happen in the first three months, six months, maybe a year after the acquisition of a big pile of money, to say it inelegantly, those are really fragile times because they're almost always reactive to some version of that person's psychology more than a thoughtful, intentional decision based on their new wealth availability.

Oscarlyn Elder:

And I think also within that time there's a fragility because you often have the wealth creator who spent often at least a decade, if not more, creating the wealth. Often there's some nerves around, OK, what is it going to take to sustain my lifestyle and the legacy that I want to create? And if the capital is deployed really quickly into other areas, it can create some risk down the road. And we've certainly seen that over time, which is why I think, especially for entrepreneurs who are listening, business owners, what we're really encouraging is creating the space to do the work as much as you can ahead of time is just really important.

Sherry Walling:

Yeah, your audience can't see me nodding vigorously, but I just so second this idea that to take some intentional space away from big decisions is very important, and to let the dust settle on who you are and what you want. And it sounds like we've probably seen very similar stories of people moving quite quickly to make a big investment in something that feels maybe mildly adjacent to their area of expertise but is not a good bet for them at that time. I guess maybe one other thing that feels important to mention here that is particularly taxing in those early days after the acquisition of a big pile of money, what do you call it, capital? Let's call it a big pile of money.

Oscarlyn Elder:

Big pile of money works.

Sherry Walling:

Is the relational impact of that. Certainly I've worked with many entrepreneurs who are scrappy and have acquired so much wealth because they didn't grow up with wealth. They came from nothing, and so they were hungry and driven and turned out to be very successful, but it's often that success that separates them from their friends and from their family and from whoever they came up with. And so there can be in those early days post-exit people coming out of the woodwork asking for loans and money and donations. And suddenly, the people that were friends and peers and family members see the entrepreneur who's completed the exit as a financial resource in a way that can be very isolating and leave them feeling without peers or that they have now just become this sort of transactional machine instead of like a beloved parent or cousin or whoever they are to the people in their lives.

Oscarlyn Elder:

Yeah. And that's a unique isolation that they may experience that adds additional emotional stress to the business owner, to the entrepreneur. And so again, just like building that network, beginning to build the community, beginning to make contact with folks who can understand that unique journey is really important.

Sherry Walling:

Yeah, exceptionally important. I think, too, some of this can happen in the pre-planning and in the early exit, which is to sit down with a wealth advisor, sit down with your coach or your therapist and think out what is my philosophy of generosity? What is my, like, template answer to the family members or friends who are asking me for money? And just thinking through some of the questions before they're asked so there's a guiding principle or a philosophy or sometimes even an email template that can help people know how to handle those questions.

Oscarlyn Elder:

I'll just point out, we're talking about this in the context of a business owner, but you could experience the same thing if you inherit wealth from a parent or from a loved one. And so that pre-thought that, again, that pre-write is just really important, especially if you have the space to do it ahead of time. Well, after every transition, there's something that comes next. We'll talk about rebuilding a sense of purpose, identity and meaning after a big change when we come right back.

Dr. Sherry, you worked with many people who've achieved significant success professionally. What have you learned about the difference between achievement and meaning?

Sherry Walling:

Meaning is an interesting and somewhat difficult to define by-product of a good life, but I think achievement are the things that we list on our resume. They're the things that come after our name on our LinkedIn profile. "I'm a clinical psychologist, I do this, I do that, I'm these things." But meaning I think is really the juicy connective tissue of our life. It's the thing that helps us to feel content and happy and that we are generally leaving the world a little bit better because of our presence here. So meaning can be in our children, it can be in our creative, it can be in the ways that we employ people or create opportunities for people, but meaning is really living a life that aligns with what we most value.

Oscarlyn Elder:

And as we think about transitions, do they sometimes offer the opportunity for folks maybe to explore the difference between those two concepts?

Sherry Walling:

I think they do because in many of these transitions, you may be moving away from the achievement mindset, moving away from the academic achievement, moving away from the business-building achievement, the acquisition of wealth achievement. I mean, at some point there's a level of wealth that you have acquired that it's just no longer an achievement anymore. It's kind of done. It's crossed off the list. And I think meaning allows us to ask really different questions, not only what can I do, I'm proving my value, I'm proving my ability, but meaning is, like, what can I contribute?

Oscarlyn Elder:

Are there characteristics that people who are moving through major transitions in a healthy way have in common?

Sherry Walling:

The thing that pops up first for me is a sense of humor. That's such a valuable asset throughout any part of our lives, but I think we as humans are amazing and creative and brilliant and all those things, and also we all started naked and crying, and we're probably going out that way. So this idea of not taking it so very seriously and having a balance of humility and pride I think is very, very important. Another quality, of course, that we've talked about already is a sense of connection, of having relationships with people where the core of the relationship is not about the success or not about the transition, but a group of people that you go play pickleball with every Wednesday and they don't know if you're worth $50 million or if you're just living paycheck to paycheck.

And then of course we want to have some relationships with people who are really on the inner circle who can help us, who can guide us, who are here for the play-by-play, whether that's our spouse or our best friends. And so not devolving into isolation, not devolving into taking it all so seriously and believing that the outcome of this deal is the only thing that matters in our lives.

Oscarlyn Elder:

Well, if somebody's listening today and they anticipate a big transition and maybe have a future retirement that's not that far away, or they could be caring for a loved one who is ill and there's a transition coming down the road, what's the one step that they can do now to help them start to navigate that uncertainty that's ahead?

Sherry Walling:

One very practical tactical behavior and activity, 10 to 15 minutes a day, is to journal. I think that is a very helpful way for us to be in touch with our own selves, to be self-reflective, to be self-compassionate, to practice some gratitude that can help us navigate a transition over time. So just spending some time with oneself in the quiet, maybe morning hours, 15 minutes of writing. And hey, we live in an era of AI. You don't even have to write. You can just talk to the robot, and it will write it for you and clean up your language and make you sound like a poet, which is wonderful.

But the power of journaling is in staying present to what's happening in all of it, in the grief of it, the trickiness of it, the disappointment of it, the drama of it, and in the magic of what it looks like to be present for someone in the last years of their lives, the privilege of what it's like to raise a child, all that people can be grateful for in the successful closing down or ending of a business. Journaling helps us be self-reflective, helps us practice gratitude, and that's kind of like a, next to sleeping well, the highest bang for your buck mental health activity that I suggest to people.

Oscarlyn Elder:

And that's what we want certainly for our clients and the people that we're advising and for all of you who are listening, right? We want you to be able to live a life without those regrets, to really live your best life.

Sherry Walling:

That's kind of the point here, that our lives and these transitions, we don't want to miss any of it, even the hard things. And so to be in a practice where we're listening to our own voice or we're writing our own thoughts helps us just to show up, I think with more intention and thoughtfulness in the ups and downs of the rollercoaster of these big journeys, and that's what we're going for as humans. We're not going to do everything right. We're not going to make all the decisions perfectly, but to be thoughtful and intentional generally is the thing that is going to lead us to the least regret and the most satisfaction.

Oscarlyn Elder:

Well, Sherry, before we wrap up, we have a tradition here on I've Been Meaning To Do That where I ask, what's the one thing that you've been meaning to do that you haven't done yet and that you're willing to commit to do now with our audience listening?

Sherry Walling:

OK. I feel really called out by this question. So I had a brother that died in 2019, and my mom has been wanting to go to Montana to the place where he died since then, and she has some mobility issues and just can't go by herself. And so I've been meaning to take her to Montana for a number of years. And I saw that this question was coming in the pre-show notes, and I reached out to my mom and I was like, "I think we should go this August." So I am going to take my mom to Montana so that she can do this important work for herself.

Oscarlyn Elder:

That's beautiful. Well, we wish you just an incredible trip with your mom and hope that she and you find that connection to your brother.

Sherry Walling:

Yeah, thank you, and thank you for the question.

Oscarlyn Elder:

Well, Sherry, thank you again for joining me today. I've really enjoyed our conversation, and I know that our listeners are going to take away specific action steps that can help them move forward through major life transitions.

Sherry Walling:

It's been a pleasure talking with you. I'm so glad this podcast exists. I know it's a gift to your audience, and I'm happy to have been a guest. Thanks so much.

Oscarlyn Elder:

And, listeners, I want to thank you as well. If you liked this episode, please be sure to subscribe, rate, and review the podcast and tell friends and family about it. I also invite you to listen to the new podcast from Truist Securities, Navigating Beyond the Expected, at Truist.com/BeyondPodcast. If you have a question for me or a suggestion for this podcast, email me at DoThat@truist.com. I'll be back soon for another episode of I've Been Meaning To Do That, the podcast that gets you moving toward fulfilling your purpose and achieving your financial goals. Talk to you soon.

Speaker 3:

Oscarlyn Elder is an investment advisor representative, Truist Advisory Services Incorporated. Any comments or references to taxes herein are informational only. Truist and its representatives do not provide tax or legal advice. You should consult your individual tax or legal professional before taking any action that may have tax or legal consequences.