Ben Killoy

Ben Killoy

The Time I Forgot My Luggage

It was 2019; I was on my way to Washington D.C. for a conference; I had preplanned to arrive on the first fight in the morning so that I could have the entire day to enjoy D.C.

I arrived at the airport, parked the car, and at that moment it hit me. I don’t think I have my luggage. It was like the floor dropped in my stomach.

I was an hour and a half from home, and I would miss my flight and the opportunity to see D.C. if I went back for it.

I had a choice to make, go back home, get my luggage, reschedule my flight, and pivot my plans for the day, or do I wing it. Wing it was not something I had ever done, but all I had on me was my backpack, laptop, and jacket.

I sat in the car thinking through all the different angles I could work with and what kind of outcomes could happen either way.

I believe that life has meaning even when it doesn’t go right, and I knew, either way, it would work, but I had to decide which way to go.

I heard of a few stories about how people will add challenges like this to their travel to just getting used to change and figuring it out on the fly.

Well, I chose Wing It that day.

I boarded a Southwest flight for the first time since leaving for boot camp with nothing more than what I had on me. No clothes, no underwear, no socks, nothing but me.

We landed on time; I skipped right to enjoying the sights and got to do it with my good friend Kirby Scott Ingles. Because of that trip, our friendship has grown and is still growing today, but it wouldn’t have started as it did have I not gotten on that plane without my luggage.

After we saw the sights of D.C., we headed on over to Pentagon City Mall. I had no idea that the Pentagon was also a city, not just a building. However, my friend had been stationed at Arlington Cemetery, so he knew his way around.

It turns out they sell clothes in D.C. too. To this day, some of my favorite shirts were purchased on this trip. If you ever see me on video in a blue polo shirt.

The day wrapped up, and everything worked out the way it was supposed to; I even had a local friend Rich Cardona in D.C. give me some backpacks he had at home to carry my clothes back home. And because I was on Southwest, my bags flew free.

Two things stick with me from this story to this day.

First is that when you need help ask, I posted on social media at the airport what I was about ready to do, and the outpouring of people like Adam Braatz to fly my bags with them on a later flight if I could get it there or to bring some extra clothes with them was humbling. I hadn’t experienced such generosity from people like that online.

The second is that we don’t need to bring what we have with us. We don’t need to take what we have accumulated with us. At any moment of our life, we can WING IT and leave behind what we have and start fresh. This lesson hits me as I relate it to the generational trauma that I have talked about this week. We think we need to carry the burden of what we have accumulated in our life as we keep moving forward.

But like I did in the airport parking garage, we can always choose to leave it all behind and figure it out. We all have the opportunity to collect new things, collect new beliefs, collect new relationships.

We all have the opportunity to leave the past behind. But, realize each day is an opportunity to fly with just what we have on our back.

How high could you fly if you leave behind what you carry with you every day?

More Blog Posts

Kids Don’t Need Us to Be Perfect

Kids Don’t Need Us to Be Perfect Last year I decided to take my oldest daughter skiing; I had been a few times early in my life but not much as an adult, but living in Wisconsin, it had been on my mind for a while to pick it up again. I remember procrastinating the

Read More »

Are You Home Yet?

I spent the first 5 years after my Military service looking for the feeling of home.  I had a good-paying job, I had just built a brand-new home, I was a husband, I was a dad, but dam if I didn’t feel empty inside.   This early mid-life crisis led me precisely ​to where I am

Read More »

Subscribe to the Podcast

My FREE Guide on Five Proven Strategies to have a better connection to your family TONIGHT!

Unlock Your True North

Your life might look good on paper, but do you hear that inner whisper asking for “more”? Dive deeper, transform, and redefine your path. Remember, if you aim at nothing, you’ll hit it every time. And a dream without action? Just a wish. Let’s craft a plan together in a Breakthrough Session and find your True North.