“A Good and Faithful Servant” – My Journey Toward Leaving a Godly Legacy By Living a Flourishing Life

by Matthew Lesser

As a coach and consultant, one of my favorite exercises to do with leaders and leadership teams is to have them evaluate the legacy they desire to leave. The exercise has them fast-forward to the end of their lives and ask what three things they would most want to be remembered for by those closest to them. If what they want to be remembered for does not align with the story they are currently writing for their life, I encourage them to put down a period, turn the page, and begin writing the story that will lead to the ending they desire…not the one they dread.

Having an end-of-life perspective is healthy; however, for years, I missed something in the exercise that pales in comparison: the six words on the other side of this life awaiting followers of Jesus Christ: 

“Well done, good and faithful servant.”

How I Wrestled With My Story of Becoming a Good and Faithful Servant

I believe God gives us the pen and the book to write our story in. Yes, He is actively engaged and acts directly in our lives, but out of His immaculate love for us, He’s given us the pen. 

For the first half of my career, my story was focused on three things: 

  1. Bigger

  2. More

  3. Faster. 

I took over my family business two years out of business school. The transition happened in one day, literally. I went into my dad’s office to resign. Instead, he left – literally! He moved 1,200 miles away, divorced my mom, and handed me the reins on his way out. 

Because I was successful in business school, I thought that meant “guaranteed” success in business. Four months later, near the time of my first wedding anniversary to my elementary school sweetheart, the business was facing certain collapse (business school didn’t teach me how to deal with a failing business). 

Six months after that, I was at rock bottom. I suffered from clinical depression, experiencing debilitating panic attacks; I was hopeless and helpless and decided it was time to end my life. 

At rock bottom–at the end of myself–God was there waiting for me. In a series of miracles, I was removed from the business to get mental and emotional help, and a friend sent in a team of professionals to assess what we had. We had just enough to start over. Nine months from rock bottom, the business started over, and it was profitable from the first month. Over the course of the next decade, it grew over fifteen-fold through organic and acquisition growth. 

Let Me Share a Story that Might Sound Familiar

After selling the business, I spent the next twelve years in private equity. I traversed the globe, meeting owners and leaders of businesses while looking for investment opportunities. 

Over time, leaders shared a story with me. I heard this story so many times that it became a pattern. Different storytellers. Same story. It went something like this: 

I sacrificed time with my spouse and kids. I missed important events like birthdays and ball games. I prioritized my business and ‘to-do lists’ building this business–this empire. For what? I have everything I could ever want–money, a nice home, vacation home, cars, toys, reputation, power, access to important people, and luxurious vacations. And now, my kids are grown and gone, and I barely hear from them, my spouse and I don’t know one another, and I am not satisfied. Not in the least. Why did I do this?

And I didn’t hear this on rare occasions; this was the norm! It’s still happening today. Leaders are writing their stories according to this old pattern. And they want out.

As I was picking up on this pattern, God was also awakening the same realization in me. If I had come to the end of my life, I realized I wouldn’t have called myself a good and faithful servant. This sparked an inner dialogue that went something like this: 

What am I doing? I have sacrificed time with my spouse and kids, I missed my little (and only) girl’s first steps; I missed my boys’ ball games, and I missed my kids’ concerts, performances, and awards ceremonies. For what? To travel the world, meet with important people, build a bigger platform, increase my reputation and name, climb the corporate ladder, have more influence and impact, make more money, buy more ‘things and stuff’...

Climb Down the Corporate Ladder. Live a Flourishing Life

In 2018, I left the world of private equity, but I did not yet know two critical pieces of information about me:

  1. My Identity

  2. My Why

So, I spent one year in the banking world and realized that it was not for me, and then I spent one year helping a friend build an executive team for his family business. It was during this second year that I started writing a book, which was something I had thought about for about a decade, but only seriously considered for five years. 

For five years, I literally prayed that God would take away the desire to write a book because I knew how difficult it was to write a book and get it published. It seemed every time I would pray, God would give me more clarity rather than release me from writing. So, I stopped praying about it! Three years before I started writing, God gave me what became the “The Flourishing Life Model,” which is the book's core. During the early months of 2021, I wrote what became the introduction to my bestselling book, unSatisfied: When Less is More. I finished the manuscript in January of 2022, and after my editor beat it up significantly, we finished the editing process in July; it was released in October 2022. 

While writing the book, I sensed God was telling me it was time to pursue what He had called me to when I was a teenager – to write, speak, teach, train, and equip others. I launched Uniquely Normal, LLC in July of 2021 out of the “collision” of passion, gifts, and skills, value contribution to others, and calling. While my first book was being wrapped up, I started writing my second book (release date of late 2023), which builds upon the foundation of the first book. The second book focuses on building healthy, flourishing leaders and leadership teams who desire to build healthy, flourishing organizations intentionally. 


Don’t Leave a Legacy Alone

When I burned my proverbial ships over thirty years after the initial calling and went all-in into this new adventure, I did not have full clarity on what I was to do; however, I believed God was calling me to surrender, trust, and have faith in Him. I launched the business with a four-pillar foundation: writing, speaking, coaching, and consulting. As I was launching, an 83-year-old mentor and friend encouraged me not to go on this journey alone. I asked him what he meant because I could not afford to hire anyone. He advised me to start a Personal Board of Directors. I did, and he became my first member. I asked my wife and two other men if they would be willing to meet with me for a half-day every quarter. The key criteria for serving were the following: 

  1. Love God

  2. Love me, my wife, my kids

  3. Speak the truth–especially the hard truth

  4. Experience launching and running businesses for Kingdom impact. 

I can honestly say that without my wife and these three men with me on this journey, I would have most likely abandoned this journey already. They speak the truth, encourage, counsel, challenge, love, hold accountable, and kick me in the rear end when I need it. Having these individuals in my corner has saved me from going off the rails, steered me away from questionable decisions, and kept me moving forward–even when it feels like I am trudging through wet concrete. I encourage every investor, business owner, and leader – regardless of the type of organization – to consider putting together a Personal Board of Directors.

Becoming a Good and Faithful Servant is a Lifelong Journey

My natural way of “doing” is to “do” while giving a perfunctory prayer of “And you are going to bless this, right God?” Today, I am focusing on living intentionally by focusing on being, belonging, and becoming while seeking Him to determine my doing. Scary? At times, however, I have never experienced as much peace, satisfaction, purpose, and joy as I do now…while making less money in my career than I ever have! Jesus has also been clarifying my “why.” My “why,” my purpose, is to provide inspiration and hope to catalyze others to intentionally pursue a flourishing life who are encouraging others to do the same.   

What about you:

  • What is your identity? 

  • Who are you? 

  • What is your “why”? 

  • What is your purpose? 

  • What are you pursuing? 

  • Who is it for? 

There is only one you in the world. You only get one life and one story to write. You have a choice: your story can be intentional–writing the story with the ending you desire; or your story can be unintentional–writing the story that may conclude with the ending you dread. I hope that you can confidently say that you have been a good and faithful servant in whatever God has called you to.

So, what story are you writing?


When writing your own story, it can feel overwhelming. It seems like all the pressure is on us to grow a business, love our families, and serve our communities. But really, it’s all God’s.

Check out this video that puts life, money, and success into perspective. Enjoy!