What makes someone an effective entrepreneur? I found one piece of the puzzle in an unlikely place recently: a series of airports.

The departure, day one

My beloved niece was getting married in Philadelphia, and I was flying direct from Ottawa. Unfortunately, the day of the flight there was a huge thunderstorm, in Philadelphia, bordering on a hurricane, and when I arrived early for my flight on Thursday, I was told the plane was delayed because we wouldn’t be able to land in Philadelphia.

Hours later, the storm moved out of Philadelphia and we boarded the plane. But by the time we were on the tarmac, there was a thunderstorm in Ottawa. We were told not to worry, as the tires were rubber, but it was genuinely terrifying to be sitting in a metal capsule surrounded by lightning. Of course, the ground crew couldn’t work during those conditions, and they waited until the final drops of rain had stopped. Finally, we could be on our way! Except…by then a second wave of the enormous almost-hurricane had hit Philadelphia, so even though Ottawa was clear, we couldn’t fly out.

We were deplaned and told us to see if we could be rerouted. I went to join the very long line at the counter; it was by now the end of the day, and there was not a single flight left to be found leaving Ottawa, Montreal, or Toronto the next day, Friday. There was a rehearsal dinner on Friday and the wedding itself was on Saturday, and we really, really wanted to make it—but it wasn’t looking good.

To make matters worse, my son had taken an indirect flight on Thursday, stopping in Toronto. His flight couldn’t get to Philadelphia either, and he couldn’t get back to Ottawa on the airline he’d taken to Toronto, so he changed airlines, retrieved all his luggage, and finally flew back to Ottawa at 2 a.m., two hours after I did. We’d each spent twelve hours on fruitless “travel” and we were exhausted.

The airline agent told us that if we could get to Watertown, New York, we could get a flight to Philadelphia on Friday. So I started calling around to find transportation to Watertown. We couldn’t rent a car in Canada and leave it in the US (we were still flying back from Philadelphia), and we couldn’t get a bus. I couldn’t figure out how I’d get my car back if I took my own. Eventually a friend of a friend of a friend who was a taxi driver agreed to take us (for $300 Canadian, plus gas. Desperate times!).

The departure, day two

I texted my son to say I’d pick him up at 7:15 a.m. to catch an 11:00 a.m. flight in Watertown. On Friday, we got to Watertown in pouring rain but no lightning—we were finally on our way! We boarded the plane and started to taxi to the runway when the plane started making a loud clicking, clunking sound. The pilot tells us we have to go back to the airport due to a mechanical problem.

So we headed back to the airport, and I was first in line for rerouting. They told us the mechanic would be there soon and we should leave by 2 p.m., but there were no other flights to Philadelphia that day, and I wasn’t taking any chances! I told the airline to get us in a taxi to Syracuse, and to get us on a flight to Philadelphia from Syracuse. They agreed.

Just before we got the taxi, I looked at the documents the airline has just given me and I realize they didn’t give me a boarding pass. My son jumped out to get us boarding passes. We were about to leave again when I checked and realized they had put me on the wrong flight, so he went back to the airline and got me another boarding pass—for the right flight this time.

The arrival!

Two hours later, we were finally at the Airbnb my sister had rented, and had just enough time to shower and get to the rehearsal dinner. The wedding on Saturday was beautiful, and we were both so glad to have made it. Those many hours of travel were worth it!

The stubbornness

 If it’s tiring to read about, it was absolutely ridiculous to live. I know that most people would’ve given up a long time before I did, and I have been trying to figure out what made me hang in there for so long. What character trait makes someone decide that nothing will stop them from their goal?

My son is a very persistent, self-made businessman doing very well for himself. He’s intelligent and hardworking. And even he was ready to give up entirely on the trip after the first-day debacle. So what’s the difference, what make someone so stubborn that they’ll only move forward?

Knowing when to let go is an important skill, knowing when you’ve learned a lesson and need to stop investing in a project because it’s time to move on. But there are also times when you need to stick with your idea and goal and make something happen no matter what. What’s the difference between the two? When do you stop being stubborn and realize that there’s another path, a better way, and when do you refuse to rest until you’ve reached your goal?

For me, I think it depends on the ultimate goal. In the case of this ridiculous travel adventure, my wonderful niece was having a once-in-a-lifetime occasion, and I wanted desperately to be there with her and the rest of my family.

If the goal is big enough, perseverance kicks in

So maybe if your goal is bigger, if what you aspire to is big, then you will make the sacrifices to get there. If your goal is to change your part of the world and to give opportunities to people or help people become better versions of themselves or help resolve conflict or make sure that art is an agent of transformation in your city or create a business that will make people’s lives easier—if you have that bigger goal—then you will stop at nothing to make it happen.

If the goal is smaller and doesn’t come from a fire in the belly, then it’s easier (and appropriate) to let go.

Right after I started out on the road to entrepreneurship, my husband got extremely sick. I looked at my husband in the ICU, my ten-hear-old son, and my mortgage, and thought hmm, maybe this isn’t the best time to go out on my own. When my old company found out about what had happened, they even offered me my old job back. But I couldn’t ignore the fire in my belly. I had a vision for how I wanted to affect the world, and I knew I had to see it through. With great support at home and with the business, especially from one wonderful sister, I moved forward with my plan. That was 23 years ago and I’ve never regretted it.

What’s your Philadelphia?

Check in with your own belly. What fire burns there? What makes you want to do it no matter what? What makes you come alive when you think about it? Which goal would you persevere to obtain no matter what? Whatever your answer, start doing that.

As Ellen Johnson Sirleaf said, “If your dreams don’t scare you, they’re not big enough.”

What’s the big dream you’d go to absurd lengths to achieve?

And what’s the longest it’s ever taken you to get to Philadelphia?

If you need help navigating the way to your goals, a good coach can help. Find out how to work with me.

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