Episode 554 | Thinking Through Your Exit + Grief and Entrepreneurship with Dr. Sherry Walling

Rob: Dr. Sherry Walling; clinical psychologist, founder, and CEO, consultant, and coach. Thanks so much for joining me on the show today.

Sherry: My pleasure. I know I’m like a hard ticket for you to get. Thanks for working with my scheduling team.

Rob: This was great—I had to talk to three of your assistants, use your SavvyCal link, do all the things. It’s great to have you here in the SquadCast room and just be able to chat it up. Been a long time since we talked.

Sherry: Yeah, like a good 10 minutes or so.

Rob: That’s right. It has been a long time since you’ve been on Startups for the Rest of Us.

Sherry: It’s been a long time. I was starting to get my feelings hurt.

Rob: Oh, I’m sorry to hear that.

Sherry: I need to set a calendar reminder is what I should do and bring you on the show every so often, because I think you’ve become such a staple in the broader startup space at this point, but especially in the MicroConf bootstrapper space people. I think you were, if I recall, the first one to get on MicroConf stage and not talk about marketing and growth, and to talk about feelings, burnout, and how to stay sane.

Sherry: The human side of the startup.

Rob: That’s right. I want to run through a few things today with you. I mean, there’s so much we could cover, and actually I want to have you back on because you are in the process of publishing a book through a publisher, and that will be out in a matter of months.

Sherry: Let’s try about a year.

Rob: So that’s how publishers work.

Sherry: April-ish.

Rob: Okay. So I’d love to have you back on to just go deep on that—both the publisher process because we self-published your first book—The Entrepreneurs Guide to Keeping Your Sh*t Together.

Sherry: Our first book.

Rob: That’s what I said.

Sherry: You get some of the blame. I heard you, I just want to rope you in.

Rob: Yeah, totally. I’m the with. It says Dr. Sherwin with Rob Walling. I’m on the side there. I contributed some content. Yeah, self-published that, and now you’re going through a publisher, which I think is super interesting. That book is about grief and your journey of the past several years actually, you lost your dad to cancer, lost your brother to suicide, you’ve obviously been public about this on your own podcast and other interviews. As we get to the point of the book, I’d love to have you back on and dive deep into that.

I have heard you say something that’s intriguing to me. What you told me was kind of an off the cuff comment, but you said something about grief is part of entrepreneurship that so much of what we do as founders and entrepreneurs involves grief in one form or another. I don’t remember if we’re talking about firing an employee, co-founder breakup, or selling a company.

Sherry: All of those things.

Rob: Exactly, plus some, like you work with so many founders—you see them go through hard things, as well as have amazing victories—you see all of that. So, talk to me a little bit about what you meant when you said grief is such an important part of entrepreneurship. Frankly, it sounds like if we’re going to be an entrepreneur, we need to learn to deal with, handle, and healthily process grief.

Sherry: If we think about grief as the emotional reaction to loss—often, we talk about it in the context of death. Of course, there’s a big grief process that goes along with the loss of life, but there’s all of these other little griefs, all of these other moments of having an emotional reaction to something that’s lost.

I think it’s such a particularly important conversation among entrepreneurship, because number one; we’re taking lots of risks, we’re trying lots of things, and we’re often operating just at the edge of our capacity. We’re learning, we’re trying new features, we’re exploring, experimenting, and a lot of those things aren’t going to work. We talk about that in the context of failure—which is good, that’s an appropriate term for that—but I think there’s also a little emotional reaction every time we hope for something that doesn’t work out, or we build something that we then lose.

There’s lots of little grief here. You named some—an employee that we’re excited about that doesn’t take the position, or leaves, a set of customers that we want to work with that we aren’t able to reach, or they no longer favor our offering.

I think one of the really surprising and really big griefs that goes along with entrepreneurship is when a company sells. I work a lot with entrepreneurs who are in transition—I’m helping people go through the process of deciding to sell, how to sell, and how to go through that process—sort of from the inside from their own mental health process. There is so much grief that goes along with that, even if it’s a great payday, even if it’s the thing that they worked for, and they wanted, it’s still this major shift, and there are lots of losses.

A big part of I think going through a healthy kind of life cycle of an entrepreneur is having a lot of moments of grief. Hopefully there’s no big grief at the end when you have a big exit.

Rob: I think most of us aren’t naturally good at dealing with loss and at dealing with grief. How can a founder get better at that?

Sherry: I think it’s important to pause. If nothing else, I think grief is an invitation to pause, to notice this thing that’s lost, to give it a little bit of emotional attention, maybe to name it out loud, maybe to memorialize it in some way. You think of an employee who’s leaving, just the time to take and get a thoughtful gift, the time to say thank you, the time to say, hey, I’m really going to miss you around here. Those are small things, but they are grief processes. They’re an acknowledgement of the emotional reaction, and they’re ways that we extend appreciation and sort of honor the role that that person played in our life.

Rob: How about going through an exit? What have you seen some founders do really well? How have you seen some founders not handle it as well?

Sherry: We both know this, there’s so many logistical processes that go along with an exit—the paperwork, the negotiation, just the conversations with the lawyers—all of those things kind of eclipse the emotional part of like, oh, my gosh, I’ve been working on this company for 3, 5, 37 years, and now it’s not going to be part of me anymore.

When there’s no space or time to think about that is when people kind of get into some trouble. They don’t recognize this real metamorphosis that they’re going through. They do the paperwork, they go through the logistics, they turn in their keys, they sort of ‘not coming back to work on Monday’, but don’t really honor this huge change that’s going on in their lives.

Those are the folks who come into my office three, six, or nine months later, who are like, I’m lost, I don’t know what I’m doing, I don’t know what direction is my life, I had this big exit, I thought I had everything I wanted, lo and behold, I’m really miserable. The healthier alternative is to be very mindful and intentional about the external goodbyes that you’re saying, all the ways that you are leaving other humans, that you are disengaging or detaching from a brand or a business that you’ve built to outlast you to have a life after you.

I know where you sit in your office behind you is a picture of the Drip logo, and it’s framed, it looks very lovely, it was given to you by the staff at Drip. It sits there in your office as a reminder of this is a thing that I built, this is part of me, it’s a piece of me, and I’ve let it go. I have a new relationship, my relationship with this company now is one of memory, is one of reflection. It’s not my active business anymore. That sense of memorializing and being able to say I fondly remember this, but I’m no longer so intimately tied to it as I was before, is a little snippet of what healthy grieving looks like.

Rob: That’s really insightful. I hadn’t thought about that. In the video snippets folks will see of this podcast on social media, you’ll see the logo behind me with the original Drippy, the robot, and his head. After we sold it, he was subsequently discontinued and replaced.

Sherry: Sad. Drippy!

Rob: Bye, bye, Drippy! I still have the shirt with Drippy on it. You’re right, I look fondly at that logo now. It’s a good reminder.

Sherry: It’s symbolic.

Rob: Yeah, and I think symbols are really important. I mean, this is a tangent.

Sherry: Drip is also tattooed on your arm.

Rob: Yeah, an image of the original logo—it doesn’t look like a logo, it’s just a water droplet. There was a very deliberate reason that I did that—it was five and a half years of my life, it is the longest aside from this podcast and MicroConf. It is the thing in my professional life that I’ve worked on the longest. It has been the biggest part of my career so far.

It’s good to remember it. It is like memoriam even though it still exists. I mean, I can drive to the Drip offices, they’re like 15 minutes that way. I still keep in touch with a couple of people who work there now. I still use the tool every day. I’m in it, but definitely don’t have that connection I used to.

Sherry: One of the things that I was invited to do during the pandemic was to help a founder think through how to hold a funeral for his company. The company didn’t make it through the pandemic, so they needed to close down. We talked a lot about what ritual, what symbol helps people be able to grieve, sort of process like, man, this company is not going to make it.

You think about a memorial service, there’s someone who facilitates it, they share memories, they share pictures, and often there’s a time for people to exchange memories. Different employees were then invited to talk through the things that they learned and the things that they will remember about being part of that company. Then, everybody went away with a mug of the logo of the company on it. It was a Zoom meeting, but it was the symbolism of like, this is ending, and we need a way to say goodbye.

To acknowledge that a company is kind of like a person in a lot of ways. We have a relationship with a company. There’s a lot of creative ways to think about grief in the entrepreneurial space that helps us honor the feelings that we do have about these entities that we call companies.

Rob: I like that you’re talking about an exit as perhaps an element of grief. Normally you think of an exit as a big celebration—you have a liquidity event—there’s just a lot of emotion and struggle around it. But I do think in the end, most of us consider oh my gosh, I just sold my company for millions of dollars. That’s a celebration, and to not also acknowledge the loss of that is a mistake.

Sherry: Well, it’s both. This category of emotional nuance that I’d love to bring into our conversations within businesses a little bit more. It can be a fantastic celebration, like good on you, you sold your company, amazing, but also there’s some other loss that goes along with a great thing.

Rob: This dovetails nicely into another topic I want to talk about with you. You and I have a lot of conversations around founders, entrepreneurship, and thought processes in your business as an entrepreneur, in my business, and in a lot of folks that we speak with through the podcast, through TinySeed and all that. Something that I’ve been having a lot of conversations about, and it seems to be accelerating, to be honest, is around selling your companies, around having an exit, and deciding when to sell.

This started happening organically, then I made an announcement on this podcast, like this is such a life changing thing to think through. If you’re going to sell your company, ping me and I will do a 30-minute chat with you. I just made kind of an open offer. Sure enough, people took me up on it. It was fantastic to hear from founders deciding, hey, I got an offer for a million dollars for this thing, and someone says I got an offer for $10 million for this thing and I don’t think it’s worth that, what are my downsides should I do this and fascinating conversations.

One thing that I have told several of these founders is just because you got an offer, it’s not a good reason to sell your company. It almost feels like some folks, hey since someone’s courting me, I should sell. Usually I’ve told them, that’s not a good reason.

Here are some good reasons to sell, you’ve gotten a huge offer that is perhaps above market or above where it should be, and it may be years before you get an offer that big again, and this is a good fit for you to sell. Like that, in my opinion, is a good reason to sell. Another one is if you feel like there’s some calamity that perhaps you could ride this business over the top, that it could plateau. Maybe you have platform risk, and you built you’re reliant on scraping Amazon or scraping Google and every day you wake up, and you think, man, they’re going to shut me down. If you think this whole industry is going to plateau, or my app is going to plateau or whatever, there are things mentally that you can get around there.

One of the other things I’ve told folks is, or if you’re just done with it. If you’re mentally done, you’re exhausted with it, maybe you’re burned out, but maybe you’re just like I’m so over this thing, and I don’t want to work on it anymore. I had said that in conversation with you when we were going back and forth, and you said, I don’t necessarily agree with that third one, because I think that’s fixable. I really like that perspective because I don’t like being backed into a corner and having to sell because I can’t handle this thing.

Walk me through your thought process there. What do you think about those reasons? I come at it from the founder perspective and now an investor advisor perspective, but you come to it from a coach, consultant, and a psychologist perspective.

Sherry: We want to be careful about making really big decisions when we’re tired, grumpy, burnt out, and dealing with some depression, because those are temporary states. I know burnout can feel absolutely overwhelming—I in no way mean to minimize its power—but it’s because it is such a powerful distortion of all typical neurological capacity, in that burnout literally makes our brains less flexible and less fluid. It’s not the best state of mind in which to make a really significant decision.

If burnout is the driver, if I’m just done with this, I think it’s at least worth exploring some other options. If you’re done, you’re done. You can sell your company wherever you want, but if it really is the sense of like, I don’t have the energy for this anymore. I think it’s probably worth taking a sabbatical. I think it’s worth bringing in a CEO or someone else to run the company, even on a short term basis. I think there are some other options that are at least worth exploring, so that you can clear your head enough to have that long term perspective of what I really want.

Rob: It’s perspective. The way to think about it, when you’re too close to something, or as you said, you’re upset, you’re in your own head, such a bad time to make a permanent decision. There are a lot of decisions we make day to day and 98% of them you can reverse—selling your company is not one of them. You have to be sure about this.

You’ve talked with people through burnout and helped them work through it. I was talking to someone who’s like, I think I’m burned out, and I need to take a week or two off. I was like, I think it’s longer than that. So when you detect someone is burned out, or whether they’re telling you that or you see the signs, what’s your go-to plan to get someone back in the state of mind that isn’t just exhausted.

Sherry: One thing that’s tricky about the terminology here is it’s not binary. You’re not sort of in a category of burnout or not, that burnout exists on a continuum. One of the things that I’m always assessing when I’m talking with someone is how burnt out they are. When we talk about burnout, from a clinical perspective, from a technical perspective, there are three kinds of clusters of symptoms or three components that we look at.

One is physical and emotional exhaustion, that’s probably the thing that feels most obvious to us like, oh, I’m just tired, I don’t have any energy for this. The second is a sense of cynicism and detachment—we just don’t care the way that we used to—there’s something sort of hardened in our heart or in our mind, toward our company, or toward the people that we work with. The last component is a sense of no longer seeing your own effectiveness. Really can be very distorted, can be totally contrary to any objective evidence—I’m working so hard and accomplishing nothing, it’s not moving anything forward, none of this matters.

The three of those together is obviously a really crappy way to feel like you’re working really hard, you don’t have any energy, it feels like it’s for nothing, and you don’t like anybody anyway—not a place anybody wants to linger for a long time. One of the things that does happen in burnout, we do see neurological changes in the brain, we can see it on a brain scan, we see certain parts of the brain being more active, certain parts of the brain, we see less neurons, fewer neuron attachments, neuronal attachments.

So we start to see changes in the brain that can become this kind of self-fulfilling prophecy or a cycle that keeps us in burnout. When we’re talking about true burnout—somebody who’s really quite fried—we have to take a long enough break to let the cells in the brain rebuild. That’s why often you are talking about probably a six-week break. Nobody loves to hear that, but it is on a biological level kind of what we’re looking for when we are hoping to see those brain areas rebuild the circuitry that is necessary for us to be creative, engaged in problem-solving, have energy, patience, and perspective.

Rob: Six weeks is a long time.

Sherry: It’s a really long time, and it’s really hard for founders. A lot of what I do is try to figure out how to make that work, but then also try to do a staged approach where maybe it’s a two-week vacation, and then we see how someone is. Did you really rest? Were you able to really detach from your business, is it okay to go back, maybe in some limited capacity? There are ways to get creative with it. Obviously, people figure it out. People do recover from burnout. I think the thing that is required is for people to take it seriously and understand that it’s not just a feeling, it does exist in your brain—the organ of your brain.

All that to say, like if you’re talking about making a huge decision, like choose to go home with when you’re super drunk, like you’re just like your brain needs to be healthy to make good choices. Your brain on burnout is not a super healthy brain, which is why we need to get back to a healthy brain before you really want to make a choice about selling your company or not. Sometimes the numbers just work out—you’re burnt out, and you got a great offer—cool, do that, but if burnout is the primary driver of a sale, I think it’s really worth some reflection first.

Rob: Easy to make a bad choice in that mindset.

To wrap us up for today, I want to dig into one other topic that you had brought up that I thought was interesting and pertinent for this time of year. You talked about changing up your work schedule for summer, potentially working shorter days, spending more time with family, picking up a hobby. We have two kids, our kids are on break for the next 10 weeks, and they have some camps, and then they have weeks with no camps. You, I, and the kids are going away for two weeks over the next couple of months—we have stuff planned. How do you imagine how our summer will be different, and how do you think founders and folks who maybe have some control of their schedule can and should look at the next few months of summer?

Sherry: I think there are two components to this conversation. One is the sense in which our time with our families is really precious. I know, it’s really easy to say that, but to really think about how to put that in action, to recognize that you have only 18 summers with your children when they’re at home with you. My friends Jim and Jamie Shiels wrote a book called The 18 Summers in which they kind of outline this case for really diving into that summer season–especially if your kids are in a traditional school schedule—to let it be this time of really connecting, making memories, building traditions, like all of the really fun, juicy parts of being in a family.

Obviously, as entrepreneurs, most of us are really busy, and our businesses don’t stop just because school’s out. But there are some creative ways to redo the schedule or plan those trips, plan those movie marathons, even the things that become family lore, and shared family experience. Summer is a really good time to just take more pauses—as families, as people in any kind of relationships—to really enjoy the ability to be together in a different way and to prioritize that in your business. Even for the people that work for you, to make that more possible for them. That’s one of the reasons, sort of the relational reason, that I think summer is a really good time to really consider changing up the schedule as a founder.

The second reason—we have a lot of wonderful research around how healthy and good it is for brains to have diverse exposure and diverse experiences—so like you and I, we spent the pandemic in front of our computers in our home offices, kind of not leaving the house, not even leaving the room that we’re in very often. Now that that is easing, the weather in Minnesota is lovely, what a treat for our brains to have them be exposed to a variety of different settings and activities. This is a great time to jump on a hobby, to learn something new, to go on a canoe trip, to just do something different with your body, and your attention to solve different kinds of problems, to be in different kinds of spaces.

I won’t go into a deep dive lecture on this, but there is so much evidence that is incredibly helpful to your business, because, again, a brain that’s exposed to a diverse variety of stimuli, is healthier, has richer connections, is better able to solve problems, be creative, and do all of the wonderful things that help us to be great entrepreneurs. Your brain wants a little vacation time, a little hobby time, and a little fun.

Rob: As entrepreneurs, it’s funny, a lot of us have the ability to make things happen and the motivation to go out and do things really well with our business. What I found for myself and I think some other founders do is that I really don’t have a lot of motivation or get up and go to go out and do a kayaking trip or to drive an hour each way to a water park on a Friday. Yet, when I’m forced to do those things, or are invited to, as I usually am, I really enjoy them.

Once I’m out there on the canoe or once I am at the water park, I think to myself, this is so cool, this different environment and these three hours off of work that I would otherwise be sitting at that same desk are really rejuvenating. I think that’s the key, to be able to take that break, take that first step, and force yourself out the door. Whether you have a family member who is able and willing to do that, or whether you have to essentially through sheer force of will or discipline or whatever it is, get yourself out the door to go do those things. It’s important.

Sherry: It’s also why most of us do this, we have chosen a path that allows for a lot of freedom—theoretically, if it’s going well, a lot of freedom. Many folks don’t enjoy it, don’t exercise that freedom. I mean, nothing makes me want to sort of reach through the computer screen and whack someone gently on the head than them having a conversation about how they feel too busy to go out and ride their bike in the middle of the day.

It’s like, you don’t have a boss, you don’t have to check in check out, you can schedule your meetings around a one-hour bike ride once a week—make your life work the way that you want it to. I think that should probably include a lot more play than most of us give ourselves time and space for. I will also make the case that it’s good for your business.

Rob: Dr. Walling, thanks so much for joining me on the show. Once again, I want to have you back here when your book is ready, and we can do a deep dive into that. If folks want to hear you talk about the mental side of entrepreneurship and how to stay mentally healthy while doing these hard things, they can check out the ZenFounder podcast, as well as sherrywalling.com.

Thank you for joining me on the show this week. As always, it’s been a pleasure talking to you. It’s great to have Sherry on, it really has been too long, like we live in the same house. I didn’t do that in the intro, but I’m figuring since our last names are the same that you picked up on that. I really enjoyed our conversation today. I hope you did as well.

I will see you on Twitter, we are @startupspod, come follow us there, and I’m @RobWalling, and if you want to follow Sherry, she’s @ZenFounder. Thanks so much for joining me again this week, and I’ll be back in your earbuds again next Tuesday morning.