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Every two weeks, I share my writing about investing, career transitions, parenting, and other topics that engage me. I'm just trying to figure stuff out.

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A Near Miss

The bus from Portland pulled into Boston’s Logan Airport at 12:25 p.m., leaving plenty of time to catch the 1:45 p.m. flight to Toronto.

I texted my friend to set him at ease. He’d been anxiously waiting at the gate for 10 minutes already. He didn’t explicitly ask for regular updates, but since my lateness introduced the stress, it was the least I could do.

We were heading to Toronto, a city we loved, to meet our mutual friend for a 48-hour visit. The usual demands of September forced a short trip. We planned the agenda carefully. Every minute counted.

I checked my watch. It was 12:35 p.m. as we gently rolled into Terminal E. Plenty of time! I was ready to speed walk to the distant gate, E3.

Preparing to depart, I reached for my bag to grab my passport. And that’s when it hit me.

Noooooo!!!!!!

I actually used a different word, but you get the idea.

Yep. That’s right. Until that moment, I hadn’t even thought about my passport, which isn’t shocking. I left myself fewer than 7 minutes to pack after forcing one last Zoom meeting into the calendar. Maybe that wasn’t the best plan.

With my heart pounding, I told my friend I wouldn’t make the 1:45 flight and then power walked to the ticket counter.

It’s not 1985, so a driver’s license doesn’t cut it. No passport, no entry to Canada. Of course, I knew that, but I still had to try. I was desperate.

And here’s where the story gets interesting.

It was 12:50 p.m. Porter had one remaining seat on the 5:05 p.m. flight that would land in Toronto at 6:30. It was technically possible to get there in plenty of time for our 8 o'clock dinner reservation.

But I hadn’t solved a fairly large problem: that 5:05 flight was boarding in less than 4 hours, and my passport was still 2 hours north in Yarmouth, Maine.

I had one shot.

There was a 1:30 bus leaving from Portland. If someone could get my passport from my house to the bus driver, he could take it to Logan, where I’d gratefully meet him as he dropped off his passengers at Terminal E.

I had roughly 35 minutes to get the passport on that 1:30 bus. Our house sits roughly 25 minutes from the Portland bus station, without traffic. Tick tock.

Since my wife was working in Portland, she couldn’t save the day this time. To be fair, she has saved me in this exact situation at least once before, maybe twice.

Instead, I called my dear friend Sasha, who lives in Portland. He was eager to help, but there was no way to get to my house and still make the 1:30 bus.

To keep things moving, he said he’d call the station to confirm the driver would even transport the passport.

After a moment or two to think, I called Chris, a good friend, neighbor, and retiree. The odds weren’t great. He’s usually busier than most people with a high-paying W2. But just before noon on a Thursday, my options were limited. I dialed.

Amazingly, he picked up.

I explained my dire situation and promptly delivered my ask. Chris loves a good challenge, and he sprinted into action. Within 7 minutes, he had left our house with my passport in hand. It was 12:57.

With Chris en route, I next called Sasha to alert him that the plan was in motion.

And that was when Sasha delivered his news. Bad news. Concord Coach refused to deliver the passport - something about liability.

But that wasn’t Sasha’s only news.

Next, he told me that he was heading to the Transportation Center. He’d already bought a ticket for the 1:30 bus. He’d meet Chris at the station, grab the passport, deliver it to me, and then ride the bus back to Portland. That’s a 4+ hour round-trip adventure at the drop of a hat.

“No problem. I’ll bring my computer and get some work done,” Sasha calmly explained.

With less than 5 minutes to spare, the plan came together exactly as he described it. Almost two hours later, at 3:45 pm, I returned to the Porter counter, passport in hand, and collected my boarding pass.

I was on my way to Toronto in time for dinner.

Most of that short flight was spent reflecting on the past twelve hours. As the adrenaline dissipated, I was overwhelmed with gratitude for those who stepped up on my behalf.

At the intersection between the friends who enabled my departure and the friends who patiently awaited my arrival, I felt a deep sense of appreciation and also helplessness. If you’ve been there, you know it’s easier to give than receive.

It’s not lost on me that this problem was entirely of my own making, entirely avoidable, and comes from a place of privilege. I messed up and was bailed out by others so I could enjoy a fun trip to Toronto. Still, my lack of planning and forgetfulness inconvenienced people I care about, which I regret.

In hindsight, the root cause seems clear; I’m probably doing too many things, and it’s taking its toll. When we’re spread too thin, lower-priority tasks can distract and often dilute our efforts on higher-priority activities.

As Gary Keller and Jay Papasan wrote in The One Thing, “Success is about doing the right thing, not about doing everything right.”

There's never a perfect time for a proper reset.

September is a great time to take stock. For me, it’ll always feel like “back to school,” and for many parents, it still is. It’s a perfect time to take an inventory of commitments and pick my spots.

Many prefer to wait for January’s traditional flurry of resolution setting and annual reviews. For others, October can do the trick. We’ve reached the fourth quarter and the sprint to year-end.

It’s funny how we rely on the calendar, independent and static, to determine when we need a reset. The calendar imposes discipline, but it also enables avoidance.

Instead, there’s a better, dynamic way to respond. The universe sends us messages when we’re off-kilter. But we must be willing to listen and respond accordingly.

I received one such message last Thursday.

Two weeks from now, I’ll be back in Logan’s Terminal E en route to Switzerland to see business partners, friends, and former colleagues. I’ve also blocked off ample time for rest and contemplation.

In case there’s any doubt, my passport is already packed and ready to go.

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And a Farewell Photo...