Taking a trip down memory lane is always special, and as a nostalgic person, I enjoy it more than most. This past weekend gave me a double dose—my oldest daughter turned 15. She’s now old enough to drive (and work!), which is both exciting and surreal. To celebrate, she wanted a family hike, so we packed up two carloads and headed to one of my favorite places: Lullwater Park.

Lullwater holds deep meaning for me. It’s in the heart of Emory University, where my wife and I met, had our first kiss, and got engaged. It’s also where I grew into adulthood, navigating some of my most formative years.

Looking back, those memories seem entirely positive, but my old journal entries tell a different story—one of excitement mixed with uncertainty. Will this work out? What happens next? I didn’t have the answers then (and still don’t now), but I kept moving forward.

Today, I find myself in another season of uncertainty—raising teenagers, nearing my 20th wedding anniversary, and growing our company. But was there ever a time when I really had more answers? Or did it just feel that way because of my younger, narrower perspective?

It’s fascinating to look back at the questions I asked myself years ago and see a version of me that often seemed more confident. Where did that confidence come from, and where has it gone?

In the spring of 2017 when I was in the middle of an election for city council, our family was dealing with the loss of a child, and the world just felt like it was in turmoil I wrote these words:

It’s all coming together now, and I for one am so happy to see where the next phase of this ride forks.  I don’t know what’s exactly going to happen in a few days, it’s probably why I’ve tried my best to control every other outcome in my life, but I know that whatever happens it’ll be for my good.

I lost that election (badly I might add), but things did ultimately turn out for my good. Soon afterwards I launched a brand new company and it ultimately led me down the path where I am today in my career.

Years later, at the onset of the pandemic in 2020 when we found ourselves homebound with the rest of society I was having a difficult time with the transition. I wrote this in my journal:

One interesting byproduct of this unique season I find myself in where I’m essentially homeschooling my kids and needing to spend so much time with them, is that I have to develop a new emotional calibration. Gone are the days when I could lose myself in work and hide out in planning or productivity because that’s comfortable or familiar. Now I have to be more consistently intentional about dealing with the emotions of my daughters.  

I think this is going to be hard for me. But I think it’ll also be good, ultimately. But it begins with acknowledging this soul tie that binds each of us, and how to successfully modulate our connectedness. 

There’s that theme again. Hope. Confidence in the future, regardless of knowing the outcome.  

Last year around the same time as I was completing another run for office, this time for a state house seat, I wrote:

Yesterday I had a good conversation with my friend Yusef where we both encouraged each other that we do in fact have what it takes to be in the arena. We’re putting ourselves out there and it doesn’t matter what other people say or think, when you’re the man in the arena, you’ve got to believe in yourself.  

I needed that advice then, just like I need it now. One of my favorite quotes is: It’s slow work building a life, but the future always comes. The future always comes. We can’t control when or how, so our best bet is to adopt a posture of hopeful expecancy while appreciating what’s happening right now.

Back to our walk down memory lane this weekend. As we strolled through Lullwater Park, I pointed out the waterfall where I proposed and shared memories of our time there. But then it hit me—my mother-in-law, who was with us, remembers that season of life very differently.

For her, it was the time when she had to let her daughter go, knowing she would never truly come back home. It was bittersweet. Every parent wants to see their child grow, but watching them leave is never easy. I get that now.

Every year, as part of our birthday tradition, we rewatch Riley’s baby videos, including her birth video. And even though she’s now 15, I still see my little girl in those moments. But she’s not so little anymore—she has a whole lifetime ahead of her.

What happens next? I don’t know. But I do know this—things will work out for her good and ours as well. Now, in this season of life, the questions feel bigger, the stakes higher. But as I’ve learned, confidence isn’t about having all the answers. It’s about trusting myself to keep moving forward, just like I always have.

SDW3