The Things Only You Can Carry

It is really hard to take a step back when you are “the boss.”

After 25 years of wearing every hat under the sun, I have grown so accustomed to carrying everything that setting something down can feel like I might lose it altogether.

For a long time, being involved in everything felt responsible. I knew the clients, the projects, the systems, the problems, and usually the solution. Stepping in became second nature.

But I’m slowly learning that delegation and trust need to be part of my managerial blueprint too.

Did it take me this long to learn that? Yes.

Is that okay? Also yes.

This lesson arrived at exactly the right time.

For the past few weeks, JHD has served as the emergency team on a large online marketplace following a failed rebuild. Our team has been embedded with the client and other developers, troubleshooting problems, navigating releases, and joining daily 9 a.m. post-release updates.

It is exactly the kind of project that would normally make it difficult for me to step away.

But right in the middle of it, I left for a six-day family road trip.

I stayed mostly hands-off, and the team handled everything cleanly. I had faith in them and they did great. It reinforced something I have probably known for a while but needed to see in action.

I do not need to be involved in everything all the time. Letting go of what others can carry frees you to build the things only you can.

I have a capable team that I trust, and I can leave the fort in their hands when I need to take a step back. That is what healthy delegation looks like to me now. Trust and capability moving in the same direction.

So yes, we took a Father’s Day road trip.

Wilmington to Charleston to Beaufort to Hunting Island, then home through Savannah. Three kids, one dog, and no itinerary.

Somewhere along the way, I had a rare one-on-one moment with my son Dylan. He told me that he hopes he looks like me one day. I found this especially funny because, of our three children, he resembles me the least.

Peyton spent most of the drive drawing in her sketchpad, which made me incredibly proud. That is exactly what I would have been doing at her age, and I love seeing her find so much joy in art.

Then there was Ryan, who simply could not stop dancing in his underwear in the pool at his uncle’s house.

One moment will make you misty. One proud. The other will make you laugh. Together, they are the whole point for me as a father.

My kids won’t remember whether I nailed the itinerary. They will remember how they felt. They will remember the laughter, the conversations, the freedom to be silly, and the time I gave them.

What I’ve ultimately come to understand about this is that stepping away is not the same as abandoning responsibility. Sometimes it means trusting the people you have spent years preparing while giving your full attention to something that cannot be delegated: Family.

It reminded me of a session I recently taught on finding hidden bottlenecks in business. I openly admitted that, after 25 years, clarity remains JHD’s biggest bottleneck.

Because sometimes the person trying to solve every problem becomes part of the problem.

A bottleneck is not always a broken process or an overloaded employee. Sometimes it’s a leader holding too tightly to decisions, information, or responsibilities that someone else is ready to carry. 

This is why leadership requires the clarity to recognize where you are truly needed, where someone else is ready to lead, and what deserves your energy.

I’m still learning how to take off a few hats without worrying that I will lose them.

As it turns out, they’ll still be there when I get back, and I have a team that can wear them well.