When the Plan Doesn't Work - Pt. 1
Aug 28, 2026
Recently, Father Michael and I went out to Notre Dame for our annual meeting with our publisher Ave Maria Press. We always fly into Chicago and then drive east to get to the University. While planning the past trip I realized we would be in Chicago the same time as the annual Global Leadership Summit, which takes place at Willow Creek Church, outside Chicago. I attended it in the past and it always filled me up. I was excited to stay an extra couple of days to experience it. The conference was on a Thursday and Friday.
At the same time, I realized I had to get back to Philadelphia by end of the day Friday. I had tickets to a special Phillies game. The Phillies were inducting Chase Utley into their Wall of Fame. I was so excited that I had bought tickets for the game months in advance. If you don’t know, I am a big Phillies fan and I was a big Chase Utley fan because he played with such a hard-nosed style. As a player, he was the definition of Philly tough.
As I researched it, I found a 1 pm flight that would get me into Philadelphia at 4 pm. This was perfect. The Philly airport sits just a few miles from Citizens Bank Park where the Phillies play. My wife Mia and son Nate could drive up from Baltimore, pick me up at the airport, and then we would be there in plenty of time for the ceremony, which was going to start at 6:15. If you do any flying, you know that thunderstorms in Chicago often delay flights. I thought about just taking the morning flight, but then I would totally miss the conference the second day and I wanted to attend as much of the conference as I could. I thought, “Even if the flight is delayed 90 minutes, I should be fine. And if something else goes wrong, I’ll live with the decision.”
The big and very full day arrived: the conference in the morning, my flight home in the afternoon, and the game at night. As I was walking out of my hotel room to go to the conference, I got a text from the airline, “Your flight has been canceled.” If you have ever had a similar experience, you know how it feels in the pit of your stomach when you get that kind of message. Your stress level immediately spikes. I threw my bags down and immediately got on the app trying to find a flight to Philadelphia. I would find a possible flight - but then it would get booked or it was too late to make the flight. Finally, I called and got on the phone with an agent. After about 25 minutes of looking at different possible flights that just didn’t make any sense, I booked a flight back to Baltimore, which would get me in at 3:45. In good traffic, the drive from BWI airport to Citizen’s Bank Park is 2 hours and 15 minutes. This was a Friday afternoon in the summer. Getting to the event on time looked like it would take a miracle.
I then settled back into my chair, trying to figure out how to spend the time and trying not to be mad at myself for not booking the earlier flight in the first place. I said to myself, “You told yourself you could live with getting late to the game. Chill out. There are bigger tragedies in life than missing this event.” But then I struggled to listen to that voice and another voice started saying, “You are an idiot.”
I’ll finish the story in my next “Tom’s Take,” but for the rest of this one I wanted to share a couple things I have learned from the event that I think apply to life and leadership.
One is the importance of living with our decisions. Once we make a decision, we need to move on and simply live with it. It’s okay that we don’t make the right decision sometimes. While our decisions do shape our lives, it's a mistake to judge ourselves too harshly by how well our decisions work out. Some decisions will work out and some will not. We will never be perfect in our decision making. When we make a decision that doesn’t work, we need to move on. Lamentations 3:22-23 says, “The favors of the Lord are not exhausted, his mercies are not spent; they are renewed each morning so great is his faithfulness.” I have long loved this passage and realize I need to apply it to the times when I feel like I didn’t make the perfect choice. If we try too much to make the perfect decision every time, we will either never make a decision or we will live too much in regret.
Second, I’m contemplating what the full day I had planned says about me. Some people might look at that day and say, “You tried to do too much.” (And that would include my pastor, Father Michael.) And I hear that - but I have to tell you, I didn’t look at that day in dread. I looked forward to that day. I loved the idea of getting some leadership insights, working and writing on the plane, and then enjoying a baseball game at night. Oh, and then I was going to stay at my mom’s house that night so we could spend some time with her. For others it would be too much. For me, I loved how the plan came together in a way that maximized the whole day. I’m always trying to get the most out of the day. It works for me and against me. If you have the same drive then I think we have to acknowledge it is in there and be aware of the temptation to push too hard or to get too frustrated when plans don’t work out. We work to plan our days but then they don’t always work out. We need to trust God in those times.
How are you with living with your decisions? How do you like to plan your days? It’s worth pondering today as you come to know yourself better. The better we know ourselves, the better we can lead others.
Rooting for you,
Tom