Eight years ago, I booked Jocko for a keynote scheduled the day after another engagement he had in Florida. At the time of booking, I called him and told him there was only one flight available that night that would get him to where he needed to be for the next morning’s event. We weighed the risk but ultimately decided to go ahead and BOOK IT, as Jocko would regularly say.
So, I did.
We signed the contract with the client for Jocko to deliver the closing keynote on Friday morning for a company-wide training event themed “Own It.” I coordinated the travel, confirmed the details, and moved on to other tasks.
A few months later, Jocko headed to Florida for the first engagement. Then he went to the airport to catch that single critical flight for the next day’s keynote. Meanwhile, I was at my kid’s baseball game when I got the first text:
“Flight is delayed. 45 minutes.”
Nothing to worry about. Delays happen. I checked the weather and it was clear. It was likely a minor mechanical issue or the flight crew running late. All good.
Thirty minutes later, another text:
“Delayed again. This time an hour.”
Twenty minutes after that, another delay. And another. At this point, I started running contingencies in my head. I checked drive times. Even if Jocko got in a car right that moment and drove straight through, he wouldn’t make it in time.
Then came the worst update yet. The flight was in real danger of being canceled altogether.
I scrambled. I searched every option possible, other airports, early-morning flights, red-eyes…anything. I reached out to the client to ask if they had any flexibility on timing. But there was none. Jocko was the only speaker that day, delivering the closing keynote before attendees left.
Jocko needed to be at that event. On time.
He texted me:
“Miles?”
Miles had contacted us months prior, offering private plane services. We had kept a good relationship, though we were not in need of his services, and we didn’t think we would ever would.
I texted Miles. He replied within minutes:
“Let me see what I can do.”
He scoured options. Nothing was available that night. But he found ONE option. A large private jet that could depart early the next morning, landing at 7:15 a.m., just enough time to get Jocko to the 8:00 a.m. gig.
The price tag: $40,000.
My stomach dropped.
We didn’t have that kind of cash lying around back then. I knew this engagement was a risk when I booked it, and now I was regretting that decision. I called Jocko and gave him the option. He quickly responded:
“Book it.”
I took ownership of the situation. But Jocko took it right back. We both owned it. We had discussed the risk and made the decision together. He wasn’t upset at all. No stress, no frustration, no panic. He simply said:
“We don’t miss gigs.”
Whatever it took to uphold our reputation and take care of the client, that was what we would do.
The cost of the private jet was more than the speaking fee Jocko was getting paid. But that wasn’t even part of the calculus.
Immediately following that situation, we created a Travel SOP. It included one crucial rule: No back-to-back gigs unless multiple flight options are available or the engagements are within driving distance. We vowed from that point forward to mitigate risk for the sake of our clients. And in over 11 years at Echelon Front, we have never missed a gig (knock on wood).
We have had some close calls. We have had to get creative. We have had to send another instructor at the last minute. But we haven’t missed one.,
The Leadership Lesson
Leadership is not just about making decisions when everything goes right. It is about staying calm, taking responsibility, and solving problems when everything goes wrong.
When things go sideways, leaders don’t blame circumstances, the airlines, or fate. They own the problem, solve it, and protect the mission.
Sometimes that means a $40,000 private jet. Sometimes it’s swallowing your pride and asking for help. Sometimes it forces you out of your comfort zone. But true leaders make the hard calls because the standard has to remain high.
