As the year winds down, I always find myself redefining success – not just by what was accomplished, but by how the year felt, what it required, and what it revealed. I’ve found that this time of year invites reflection—almost like tying a bow on the past twelve months before stepping into a new chapter. I tend to write more this time of year, think more, and make space for the kind of reflection that gets crowded out during the busier months.
Just this morning, I stepped out of a peer group I lead here in Harrisonburg. In that meeting, I admitted something I wrestle with often: it’s hard for me to celebrate the good. I usually fixate on the parts that didn’t go according to plan. That conversation is what sparked the thoughts behind this essay.
“Can I just go back to plowing?”
Last week I sat across from a business owner who has spent the last fifteen years building something remarkable. What started as a small idea has grown into a business now valued at $12.5 million. His company runs with efficiency most owners only dream of. Net profit margins have averaged 30% over the past five years. His structure is clear. His people are in the right roles. From the outside looking in, it would be easy to assume he’s living the dream.
And in many ways, he is. What his younger self hoped for has become reality. The long, exhausting years of building are now bearing fruit.
Yet, as we talked through his plan to exit the business over the next decade, He says these words, “can I just go back to plowing?“. This theme kept surfacing: he is overwhelmed. Deeply. He feels torn between the external success everyone can see and the internal pressure that keeps building. And for him, the scale is beginning to tip toward simplicity. Toward peace. Toward the quieter life of farming—the life he started in and still longs for.
Maybe you can relate to that story, over the years, I’ve noticed two common risks that show up when people finally reach the life they’ve been building toward:
We move the goalpost
I see this often with retirees. They spend decades saving diligently, working hard, preparing for the next chapter… only to arrive and immediately feel underwhelmed.
“This is it?”
If we continuously redefine “success” and never intentionally pause to celebrate how far we’ve come, the finish line will never be enough.
We get overwhelmed by what we’ve built
The business you once jumped out of bed to grow slowly becomes an administrative maze. There are employees to manage, structures to maintain, customers to serve, regulators to answer to—and woven through it all, the most important responsibilities of home and family.
A helpful indicator that something needs to change is exactly what my client expressed: a deep, persistent desire to do something else. Sometimes that longing is less about escape and more about alignment—an invitation to step back into what brings peace, purpose, and clarity.
As I’ve sat with this story over the past few days, I’ve found myself wondering what “plowing” looks like for the rest of us. For my client, it’s literal—quiet mornings in the fields, hands in the soil, work that feels clean and grounding. But all of us have our own version of that place where life feels simpler and more aligned. Maybe it’s time with family, a hobby you pushed aside during the busy years, a pace of work that allows you to breathe, or a calling you’ve quietly carried for years. As we head into a new year, it might be worth asking: What is the thing that brings you back to center? Where does your soul feel most at home?
I would encourage you to ask yourself these three questions:
- What part of this past year deserves honest celebration—and have you taken a moment to acknowledge it?
- In what ways are you redefining success in your life?
- If you were to define your own version of “plowing,” what would it look like—and what small step could you take toward it in the coming year?
I hope that as the year slows down, that you’ll be able to enjoy the moments with family and friends the Christmas season gives to you.
Best wishes my friend,
Stay the course.
