When it comes to planning an exit from a healthcare company, much of the focus tends to center on the business: financial performance, valuation, deal structure. But one of the most overlooked elements of a successful transaction is the owner's personal readiness.
To explore that often-missed side of exit planning, VERTESS Managing Director and Partner Jack Turgeon sat down with Dr. Rikki West, a business psychologist, leadership consultant, and keynote speaker who helps entrepreneurs evolve beyond reactive management and lead with authenticity.
After building, scaling, and successfully exiting an eight-figure organization, Dr. West now helps business owners do the same, this time with a focus on aligning leadership mindset and strategy for sustainable growth and intentional transitions.
In this Q&A, Jack and Dr. West discuss what it really takes to prepare yourself — not just your company — for exit. Together, they share a practical, psychologically informed framework for navigating the emotional and strategic dimensions of letting go, along with a healthcare M&A perspective on how this preparation can directly impact deal outcomes and long-term fulfillment.
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Jack Turgeon (JT): As healthcare M&A advisors, we recognize that every transaction is both a financial and a personal journey. We see firsthand how closely a business becomes tied to its owner's identity and sense of purpose. While our role at VERTESS is to guide clients through valuation, diligence, and deal structure, the emotional side of a sale often requires a different kind of expertise — one that professionals like you, Rikki, as both a business owner and psychologist, are uniquely equipped to provide.
From your perspective, what's really happening beneath the surface as owners move through the experience of selling their business?
Dr. Rikki West (RW): Business owners should expect to experience a mix of pride, relief, anxiety, grief, and even identity confusion during and following the sale of their business. Over time, the company becomes intertwined with our sense of self-concept, so letting go can feel like losing a part of oneself. Psychologically, when business owners are not fully prepared for this transition, they are likely to experience emotional highs and lows similar to the complex grieving process often associated with divorce.
Jack Turgeon: That description resonates deeply with what we see throughout the transaction process. Even the most confident and well-prepared sellers can feel that sense of loss once the business they've built begins to exist independently of them. From our perspective, that emotional undercurrent often influences everything, from deal pacing to post-closing satisfaction.
Rikki, your phrase "Your business is for sale, but you are not" captures this distinction perfectly. Why is this such an important conversation for owners to have as they prepare to sell?
RW: The transaction transfers ownership of assets and systems, but not of the entrepreneur's identity, wisdom, or legacy. Fully understanding and acknowledging this separation helps owners emotionally detach from the business while preserving their sense of self. This is a step in the process that absolutely cannot be missed.
JT: That distinction between the transfer of assets and the preservation of identity is so important. In many ways, it's what allows a seller to move from being needed by the business to being proud of what they've built. From an advisor's perspective, that mindset shift often marks the moment when a client can truly begin preparing for life after the sale — not just financially, but personally.
When should owners begin working to detach themselves from their businesses, and how can they do that in a healthy, intentional way?
RW: As soon as owners commit to the sale process, they should begin detaching. It's always best to start with small steps; for example, they could practice introducing themselves beyond their ownership title. Rather than claiming the ownership or CEO role of a company, they could try referencing the general mission of the company with something broader such as "I build companies that increase regional access to XYZ". It may seem like a small shift, but any time we reference ourselves — any time we make an "I statement" — we automatically become more self-aware, and better yet, we activate the regulatory systems that allow us to processes, monitor, and regulate any of the associated thoughts and emotions.
As a business psychologist, I also have to state the obvious and make it clear that business owners must use this time to seek emotional and psychological support from mentors, consultants, and/or psychologists who are familiar with entrepreneurial exits. In searching for this level of support, I would encourage business owners to specifically seek mentors or consultants who have built and successfully exited businesses of their own. There are a lot of "coaches" out there with polished websites and attractive social media accounts, but the only ones truly qualified to lead owners through this process are either licensed psychologists or mentors/consultants of comparable experience. This is a significant life event, and it deserves the attention of a professional who has built a comparable business in real-time, not just someone who talks a lot about doing it.
JT: That's excellent advice, and it aligns with what we see from our side of the table. When owners begin to shift their language and mindset early, the entire process tends to feel less overwhelming, both for them and for their teams. Surrounding themselves with experienced advisors and mentors who have lived through a healthcare business exit makes a world of difference. It's one thing to prepare financially for a transaction, but preparing emotionally often determines how successful the transition feels after the deal closes.
You've talked about emotional detachment as a key part of this process. Is that the most important factor when separating from a business, or is it just one piece of a larger framework?
RW: Emotional detachment can often be the most complex, but it's only one part of a three-part process. To achieve the best possible outcomes, owners need to prepare cognitively and behaviorally as well. There are some ways owners can start doing this today.
First, redefine success by moving attention from financial growth metrics to fulfillment and impact. Owners should start delegating decision making tasks, especially those that are directly tied to revenue. They can use this vacant cognitive space to plan for their post-sale identity and explore new roles as an investor, mentor, or philanthropist.
Second, they should develop non-business anchors. Identify hobbies, family time, or personal pursuits that excite them — and start pursuing them now. Make time for these activities by stepping back gradually at the office. Allow your leadership team to take ownership before the sale and experiment with days off and unstructured time to practice post-exit living.
JT: I really like how you frame this as more than just an emotional exercise. In our experience, the owners who approach their exit with that same cognitive and behavioral discipline — redefining success, delegating early, and testing what life after ownership looks like — tend to have smoother transactions and more confidence in their decisions. Those adjustments also make the business stronger and more transferable, which is something every buyer values.
You've mentioned a broader framework that helps owners evaluate their overall readiness. Can you walk us through what that looks like and how business owners can use it to prepare for a healthy transition?
RW: The transition framework that business owners can use to evaluate their readiness across all three dimensions is a simple self-reflection exercise that looks like this:
- Emotional: Do I have the right support system to help me fully acknowledge and move through the grief and pride that I will experience throughout this transition?
[Will my identity remain intact?] - Cognitive: Do I have a new vision of success for myself beyond ownership of this company, and have I imparted the knowledge and leadership skills needed for the company to survive without me?
[Will my legacy be known?] - Behavioral: Have I built new anchors outside of the business and am I excited about spending more time doing these things?
[Will my time be valuable?]
JT: That framework is such a powerful tool. It mirrors what we often assess from a transactional standpoint — financial readiness, operational readiness, and personal readiness — but you've captured the internal side of that equation in a way that most owners never articulate. When clients take the time to reflect on those three questions, it not only helps them prepare emotionally, but it also gives their advisory team a clearer sense of how to guide them through each stage of the process.
From your perspective, how can we as healthcare M&A advisors better support our clients throughout the sale process, helping them stay balanced and confident without crossing into areas that may require a deeper psychological or mentoring approach?
RW: Continue working to integrate psychological readiness into your clients' exit planning. A hands-on approach may be incorporating a psychological readiness checklist to help clients recognize when professional mentorship or consultation may be necessary.
Another noninvasive yet productive approach is to normalize the emotional challenges and identity shifts while encouraging mentorship or consultation and championing post-sale, legacy-building activities that bring meaning to each client.
JT: I appreciate that perspective, and it really reinforces how multidisciplinary a successful exit can be. When we build an advisory team around a client, each professional plays a different but complementary role — legal, financial, operational, and, as you point out, psychological. Normalizing the emotional side of selling doesn't just make the process healthier for the owner; it often leads to clearer communication and stronger outcomes for everyone involved.
As we wrap up, is there any final advice you'd share with owners who are preparing to sell — something they should keep in mind as they take those last steps toward letting go?
RW: Selling your business does not mean selling yourself. Preparing emotionally, cognitively, and behaviorally will allow you to complete this process with clarity and confidence. Your experience, identity, and future potential will remain intact, and you will once again feel the energy, excitement, and drive that inspired the vision, mission, and business that brought you here.
On a personal note, I want to share that I built and sold a business — with amazing support from you, Jack, and the VERTESS team — and experienced each of these data-driven thoughts, behaviors, and emotions myself. Even as a psychologist, I was in no way above or otherwise immune to these challenges. I followed my own systems and came out even stronger than before. Still, it wasn't until a few weeks after signing, when my mentor kindly said, "You have nothing left to prove," that everything suddenly became clear.
You must have a mentor or consultant to help you move through this process. Nobody is immune to the difficulty of this transition. If you don't have access to an appropriate professional, ask a trusted friend or family member to support you. Use the reflection questions above as a starting point. Then allow yourself to deeply explore the meaning behind each response and allow your trusted partner to hold you accountable to each new commitment you make.
Finally, I want to share my gift-of-clarity moment with every reader preparing to sell their healthcare business. Just as my mentor did for me, I want to assure you that you have nothing left to prove. You have fought your good fight and won your race. My hope is that what you choose to do next allows you to become the person you always needed but never had — and that your success gives you the opportunity to pay it forward. Most of all, I hope you feel a deep sense of pride in all you have accomplished so far. The best is yet to come!
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Dr. Rikki West is a business psychologist, leadership consultant, and keynote speaker who helps entrepreneurs and executives evolve beyond stagnant revenue cycles and reactive management styles. After establishing, scaling, and successfully exiting an eight-figure organization, she now teaches business owners how to leverage their natural leadership traits to build trust, scale sustainably, and lead with authenticity. Rikki’s evidence-based frameworks bridge psychology and strategy, guiding leaders to align who they are with how they operate—creating organizations that grow with intention, integrity, and long-term success.