Whether you have a massive exit or a less-than-stellar one, it can feel less like a cause for celebration, and more like a loss of self. Shortly after the joy that comes with an exit, many founders feel a loss of identity, muddled sense of self, and diminished self-worth once the business no longer belongs to them.

As Dane Madsen and I discuss on the Unmessable show, this was his experience after he sold YellowPages.com, the business he co-founded, for $100 Million to what is known today as AT&T.  You would think that after successfully selling his business, the last thing Madsen would feel is lost, but this is a shared experience for many founders because who they are no longer who they knew themselves to be.

In a culture that is constantly looking for the next achievement and accomplishment-- a culture where we define ourselves by what we do-- being unsure of our place and purpose in the world can drive us straight into an identity crisis.

How can you navigate this transition? Madsen and I suggest trying these jump-starter activities:

Do a completion exercise.

Once you are fully out of the business, privately do a post-mortem or completion exercise. The intention of this experience is to create an occasion to reflect on your journey.

What went well? What didn't go well? What have you learned? Are there any loose ends that need to be tied? Are there any conversations with people that need to be had? Look to see what it will take to powerfully complete that chapter for yourself. If something is incomplete, it will show up in your thoughts and your space. That's your cue to complete it.

Discover who you are and what you value.

As Madsen shared on the podcast, "In order to reinvent yourself, you actually need to know who 'yourself' is."

In the absence of a built-in purpose that your company filled, Madsen recommends giving yourself time to think about what to do in your next chapter and avoid jumping straight into something new, like he did. Take time to reflect on your values and what you would like to accomplish in your life.

Answer the questions: What is important to me? Family? Travel? Being challenged? Working with people I deeply respect? Giving back? Working from home? Flexibility?

Clearly list what is non-negotiable for you and what must be present in your next chapter. Then, within those parameters, begin to explore what excites you. Make a conscious effort to stay in the inquiry as opposed to getting to an answer. You will see new possibilities open up.

Connect with people who had similar experiences.

You're not alone. This experience of loss, grief, and confusion is one that plagues many of us in the entrepreneurial space. If you can't find a support group in your area or online, you can either start your own or reach out directly to founders that have gone through this same experience. You could find it therapeutic to talk with someone that knows exactly what you've been through and can share what they did to powerfully set themselves up for the next stage.

Explore what you like to do.

Intentionally give yourself permission and a set period of time to explore new interests. Perhaps there's a subject you always wanted to learn about, a sport that you've always wanted to play or a type of art that you've always wanted to create.

Test new ideas to discover what you like and what you don't like. The exploration part will be refreshing and infuse you with new energy.

Schedule at least 20 exploratory conversations.

When you're finally ready to leap back into the workforce, before taking the plunge or honing in on one path, reach out to other founders whom you respect. Use these discussions to explore potential synergies and get their input on what they think you should do, based on your interests and skill sets.

When I sold my business, that's exactly what I did and interestingly enough, in the conversations themselves, my next chapter became clear. I noticed that I naturally gravitated to a passion of mine, which is people, and most of the founders I connected with suggested roles that would allow me to do what I love. It was a total eye opener and I would not have come to it by myself, in the absence of those discussions.

Remember -- after an exit, you're unveiling and discovering a completely new side of yourself. It's a journey. Be patient and try to use your newfound flexibility and freedom to your advantage in order to guide your exploration.

Published on: May 24, 2019
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