Finish Well #5: Discover: Press Reset & Dabble for a While
Part 5 of the “Finish Well” series
Most founders spend years thinking about how to get out of their business, but very little time thinking about what they are going to do the Monday morning after they are out. That can be a lonely morning.
Recently, I sat with a chairman who had finally reached the moment he had been working toward for 40 years. His team had taken over; the baton was being passed and the succession plan was in motion. Yet, instead of feeling triumphant, he was exhausted.
The transition had taken more out of him than he expected and it wasn’t going as planned. Then, with the honesty that only a weary founder can muster, he says to me:
“I think I need to press the reset button.”
That phrase. Press the reset button.
He knew that to leave and do nothing meaningful with his life for the next season of his life was not acceptable. Without meaning, he would die. All he needed was to catch his breath and discover what his victory lap would look like.
And this is exactly what Step 5 of finishing well is all about.
Discover: It’s Okay to Dabble for a While
After spending decades building a business, leading people, solving problems, and carrying responsibility, you don’t always walk straight into clarity. Sometimes you walk into fog. That is why discovery matters.
This season is not about having all the answers on day one. It is about giving yourself permission to press reset, rest a little, and dabble long enough to discover where you still have joy, strength, and impact.
You are not lost or done. You are in discovery.
The Key Ingredient: Give Yourself Permission to Reset
Don’t make the mistake of believing that finishing your business transition means having to immediately lock in your next mission. Sometimes the wisest thing you can do is slow down long enough to listen.
When I was beginning my own third career at age 65, I had already given notice. I knew one season was ending, but I was still trying to understand what the next one should be. So I sat on a bench in downtown Thomasville with Don Ankenbrandt, co-author of the 210 Project, and asked him a question that many founders eventually face:
“If you were in my shoes — age 65, good health, wonderful marriage — how would you build the most impactful season for the rest of your life?”
His answer was simple and powerful:
Do what you love to do. Take others along. Demonstrate your faith.
That is a blueprint worth remembering.
The Measurement: What Gives You Life?
Peter Drucker said to build on your islands of health and strength.
For me, one of the most helpful tools in that discovery season was the 210 Project process. It helped reveal something important: my spiritual gifts were hospitality, generosity, and encouragement.
Once I had clarity about those, I could start letting go of things that did not fit.
One of the hidden gifts of discovery is receiving permission to release what is wearing you out.
Part of that may mean reconciling some relationships or pruning some responsibilities. Or maybe reevaluating some assets and obligations. This is not a season to just add new things, it should be about subtracting some wrong things.
The Timing: Dabble First, Decide Later
Discovery means not starting with a five-step plan or map with a guaranteed outcome. It is ok to just try some things, we call that dabbling. Maybe take some steps toward that idea you never had time for or volunteer where you have always felt drawn. Take a class or join a group. Revisit something that has always given you joy. You have likely spent your life learning where you thrive, pay attention to that now. It is okay to dabble for a while.
Dabbling is not drifting if you are paying attention. Dabbling is how you discover.
Real Life: The Cliff and the Fog
Starting a new season can feel like stepping off a cliff into fog. The old season is over and you know you are supposed to move forward but the road ahead is not clear. Our Breakthrough Groups seem to make a big difference in this season. It helps to have a trusted group, coach or friend who can say the things you need to hear and ask clarifying questions.
Finishing well is not just about exiting your business. It is about entering your victory lap season with purpose.
Action Steps: Press Reset This Week
If you are entering this discovery season, here are a few questions to help you begin:
✅ What have you always wanted to try?
What did you never have time for while building the business?
✅ When do you feel most alive?
When do you feel like you are on top of the mountain?
✅ What do you know you do not want to do anymore?
Clarity often starts there.
✅ Where have you found great joy that you may want to go deeper?
Look for patterns, not just opportunities.
✅ Who can help you clear the fog?
A coach, a group, a trusted friend — do not walk this season alone.
Reset is not retreat, it’s preparation. Sometimes the most important thing a founder can do after passing the baton is pause long enough to discover how to run the next leg well. Succession planning is not just about leaving well, it’s about living well after the handoff.
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