Beyond the Exit: Crafting a Purposeful Life After Business Ownership

Over the last several years, one of Morton’s initiatives has been dedicating itself to improving outcomes for business owners by helping an owner craft an exit plan that aligns their business, their financial resources and personal life goals into one master plan through the Strategist offering.

For this whitepaper, we partnered with executive coach and strategic advisor David Dressler to get his insights on how owners can think about setting themselves up for success personally after the exit of the business.  While this might sound like an easy task, the truth is that many owners feel lost or disappointed once they are no longer the CEO.

As a co-founder and owner of Tender Greens, a company he grew from inception to $100 million in revenue and 1,200 team members, David’s first-hand experience in exit planning is particularly valuable especially as it relates to creating a personal identity beyond the business.

To read the full PDF version, click here.

Why do you think most owners struggle with creating an identity/purpose beyond the business?

As founders, it’s not that we can’t, or wouldn’t be able to craft a next phase identity for ourselves. It’s simply that we typically don’t do it proactively. In many ways, this limitation is in our founder's DNA - we either put everyone’s needs ahead of our own or we’re so stoic or headstrong that we think we’re exempt from any real personal needs.

As founders, we’re the embodiment of our company culture. Everyone looks to us as way finders for the company’s vision and mission. Our purpose is to create a prosperous brand and in doing so bring about the prosperity of our team members as well.

When founders transition to a different role through the evolution of professionalization, or leave their day-to-day involvement with the company entirely, there are two voids created that can be challenging. One for the business and its employees; the other for the founder. Here, let’s focus on the loss to the founder rather than of the founder.

Until we go through it, it’s easy to minimize the impact these transitions represent. We imagine that it’s going to be great to have more freedom and disposable time to focus on other pursuits, less pressure, more anonymity, and all of that is true. But, what at first feels like an act of magnanimity or higher calling can also quickly become both identity questioning and anxiety provoking.

Yes, founders may be authentically enjoying the idea of the proverbial handing off of the baton but most haven’t really and deeply considered to what personal end they are doing it. In other words, what do they actually want life to look like once the next runner has sprinted off, company in hand, and their minds begin to decelerate? What happens now that the first leg of the race is complete? Once the tearful goodbye party toasts have been made and everyone’s eyes have dried and are squarely fixed on the new runner and the next stage, what then?

A feeling may emerge that nobody needs us anymore, that despite our own legendary status as founders, we’ve effectively been replaced. There may even be a perception that things are running better without us or that what was once considered powerful wisdom from the founder now seems a little hokey compared to the “bigger, more pressing” issues facing the company as it scales. The business of running the enterprise continues and the people we once had endless access to are busy doing what their roles require. We now have that daily free time we so badly wanted but none of our daytime playmates to share it with! Our calls are going to voicemail. They don’t have time for lunch. We’ve gone from hero to zero.

As far as the company is concerned, we know that succession planning is an essential tool for the brand’s post-founder future. It’s obviously essential to be thinking about leadership transition well before it’s needed. But once the plan is in place, and the founder is carrying out a blend of orientation and skill training for the new #1, they are often primarily devoted to and focused on the ongoing continuity of the company’s leadership. And since they’ve typically made a career of ignoring their own wants and needs, that’s not likely going to stop by itself.

So, to put it in entrepreneurial terms, founders need to write a personal business plan - a life plan - for the next phase - unlike the last plan, this one gets to zoom out even further and consider, in addition to money and career and instead of departments like marketing, hr and ops, areas of life areas like health, fun, friends, family and spirituality. Founders need to envision what they want the major areas of their lives to look like over the next few years and then chart a course to get there. It’s not simply about their investment portfolio, their golf and travel plans but taking a more holistic look at what the purpose of this next tranche holds for them and those they love.

What are the consequences of skipping this step in the process?

As anyone who has written a business plan knows, one of the best reasons to write one in the first place is to force us to look at all the areas of the business and carefully consider our blind spots. Just because we’re not experts in marketing doesn’t mean we can turn a blind eye to marketing’s importance. The same for a life plan. If, until now, we haven’t embraced the importance of health, connection to family, our relationship with our partner, personal development or fun, we have a new opportunity to do a deeper dive, a do over or even a full court press in the areas we may have been “too busy” to focus on.

Not thinking through what we envision for ourselves leaves us at risk. When the sparkle of retirement novelty wears off and the reality doesn’t quite live up to the shallow vision we had imagined, we’re vulnerable to boredom, to disappointment, to a lack of purpose, to impostor syndrome and even some depression which can itself lead to a sense of meaninglessness impacting both mental and physical well-being.

For some founders, particularly those who struggled with workaholism, there may be an added punch in the gut when they realize that while they were busy building the empire, some of their loved ones also built independent lives for themselves - hobbies, friendships and routines that they’re intent on continuing to enjoy despite the founder’s newly open schedule.

You are an advocate for a bite size process on formulating what you will do to give you meaning, purpose and fulfillment after the transaction.  Can you share what led you to this conclusion? And what your process looks like?

It’s based on my own experience. When I began my transition, my replacement was an experienced career executive. She had great pedigree working for Apple, Peet’s and Dry Bar. I knew I was going to spend the next two years phasing out. My plan was to support her cultural indoctrination, help her get acclimated in any way I could, and get out of her way. I’d spend my time on culture and development and so I anointed myself the company’s Chief People Officer and got to work. I also knew that part of my second mountain was going to involve executive coaching and so I took a coaching certification course in my off hours and on weekends. It was fulfilling and exciting. As the last of three partners standing, I was pretty crispy at the end of the two years. One of my co-founders told me to make sure to take some decompression time for myself. I had no idea what he was talking about. I figured I’d take two weeks to build a treehouse for my daughter and then slowly start my coaching practice. I was completely unaware of my own intensity level. Then two weeks later Covid hit.

With all of us on lockdown, I had some time on my hands. I also began to feel some pretty intense feelings about closing out this chapter. I was doing some trail running and listening to Chip Conley’s book, Wisdom at Work. I can vividly remember running up the Westridge fire road crying, his powerful experience of stepping away from his company, Joie de Vivre Hotels, and the transition to his eventual role as “guide-on-the-side” to the co-founders of Airbnb was so poignant. I decided then and there to map out my next ten-year plan. I had done it once, stuck to the plan and created a unicorn of a brand with $100 million in sales and 1,200 team members. I lectured on the virtues of a ten-year plan for businesses. Why wouldn’t I apply it to my own second act?

When we sit and ask ourselves what we want this next part of life to look like, there may be silence at first. We may not be accustomed to self-reflection at that level. That’s okay. No pressure. I found it useful to journal about it. I’d start with a prompt I got from my friend Paul Ford, “The truth is…”

Journaling was a good start to opening up a creative and cathartic process. I then used a framework that comes out of years of work with a men’s mentoring organization.  I have adapted, personally used and taught this process to over a thousand people. Of all the tools I’ve got in my coaching tool bag, the C.O.R.E. Framework is one of the most powerful because of its simplicity and usefulness in all facets and circumstances of life.

How does having a clearer vision of what one wants their life to look like after the transaction impact how a business owner might approach their exit plan?

C.O.R.E. is based on three truisms:

• You can’t get there if you don’t know where you’re going.
• You have to know where you are to know how to get there.
• A map will get you there faster.

C.O.R.E stands for:

• Context: it’s our attitude, it’s how we show up in any given situation.
• Objective: it’s the destination - where we’re going and why we’re going there.
• Results: what we want to achieve as a result of this endeavor?
• Execution: when will I take action and who will help me?

This methodology gives a founder a direction forward for the next 3, 5 or 10 years and a clear path for the next 12 months. I hear from founders that I work with that they don’t want to have a plan. They’ve been programmed and scheduled their whole professional lives. They simply want to feel into the next chapter and see where things go. I totally get that. That unstructured living can be part of the plan. It’s a mindful approach rather than a mindless one. It’s a plan based on purpose and meaning rather than based on not much at all. We were, at one time, so extraordinarily thoughtful about the vision for our businesses. Why wouldn’t we be just as discerning about our lives?

Career - What’s next? How will you be paying it forward? What’s going to bring you purpose?

Money - What’s your personal relationship with money like?

Romance - What’s next for the two of you? Single? What does companionship mean to you?

Family - Moving forward, how do you want to show up so that you’re on track to living without regret?

Friends - What does meaningful time spent look like?

Fun - What’s on your bucket list?

Health - What have you been neglecting, ignoring? What do you want your body to look and feel like?

Spiritual growth - What do you want to discover about yourself and your relationship to the universe?

These questions and many more are deserving of our attention. We’ve worked so hard for our success. What do we want to do with it?

What tools or resources do you use to address this part of an owner’s journey?

This process is simple but not necessarily easy. Part of working with a coach like me is about having an impartial sounding board to talk through the feelings that come up before, during and after the transition, flesh out the different options and get clear on which are the most resonant. I have a wealth of tools I use to deepen these conversations, my own stories to share, as well as an intimate network of trustworthy wealth managers, equity specialized attorneys, health and spiritual allies and others where I’m not the expert.

Here are a few books that were very meaningful to me:

• Second Mountain, The Quest for a Moral Life by David Brooks
• The Earned Life: Lose Regret, Choose Fulfillment by Mark Reiter and Marshall Goldsmith
• Wisdom at Work: The Making of a Modern Elder by Chip Conley
• Man’s Search for Meaning by Viktor Frankl

Tell us about your coaching practice and what you hope to accomplish with it?

My favorite part of leading our organization was helping people succeed and grow into powerful leaders. I was honored to mentor so many managers, directors and vice presidents along the way. Many of those people started out as individual contributors, matured and took on greater and greater responsibilities. As they climbed they encountered new challenges and complexities. I loved being a resource for them. I loved that “go talk to Dave” became advice given in our organization to leaders who wanted to level up by transitioning, transforming or transcending their current situations.

After leaving the day to day at my company and using my own medicine on myself, I stripped away all the tasks that were part of my job description and kept what I love and what, besides my family and friends, gives my days meaning. That’s what I do now for directors through c-level executives.

I work one on one with leaders. I also lead retreats for their executive teams who want to go deeper into their alignment, their purpose and their servant leadership. I help partners resolve conflict. I act as a translator between boards and management teams. I do some group coaching as well.

With all my clients, the work is rarely just about the blocking and tackling of scaling career and business, but leading in all facets so they aren’t dragging their lives behind them.

Some of my most meaningful work is with founders; those still in the game and those ready (or almost ready) to move on. Together, we craft meaningful and proactive succession plans for their companies and transition plans for themselves.

In the 15 years I spent scaling my company, I refined the C.O.R.E. Framework which I now use to help my clients.

I’m industry agnostic. My main referrals come from attorneys, fractional CFOs, heads of HR and private equity folks. So discretion is very important to me.

If you know someone who’s in uncharted waters in their career, experiencing overwhelm or conflict with partner, boss, board or team or, simply coming to the conclusion (or needing to) that what got them here isn’t going to get them there, it might be a good time to have them call me. I’m happy and honored to help.

Conclusion:

When I think of exit planning, it's essential to have a comprehensive plan that aligns the three legs of the stool: the business itself, the personal financial plan, and the individual’s identity. From hearing firsthand about David's experience successfully navigating an exit, it's clear he understands the importance of not neglecting that third leg—one that often gets overlooked. His passion for helping others avoid this common pitfall is invaluable. We’re fortunate to have professionals like David who emphasize the significance of aligning personal fulfillment with financial success. In the end, true fulfillment isn’t just about the monetary rewards or the achievement of building and selling a business—it’s about being at peace with who you are and the legacy you leave behind.

Disclosure: The views and opinions expressed in this article are those of the interviewees and may not necessarily reflect the views of Morton Wealth. The above information may not be representative of the experiences of other clients, and do not provide a guarantee of future success or similar services.