Careers rarely go according to plan. In Job Hacks, we shake down experts for the insights they cultivated on their way to the top of their field.

Name: Brian Lessin

Original hometown: Stamford, Connecticut

Job: Pilot for FedEx

How did you get your start?

My father was a general aviation pilot, so from very early on, I was around them. I decided that’s what I’ll do for a living. The first time I was ever in a light airplane, I was 4 years old. I have pictures of me with my hand on the wheel. But I would say 12 years old was the first time I actually controlled an airplane by myself without outside intervention.

Is that common or unusually young?

That’s young. Unless you have a family member that owns an airplane, you just don’t have the opportunity. My father flew airplanes and owned an airplane, so I wasn’t flying by myself but I was controlling the airplane without him touching anything else. Think of it like when you’re in the car and your parent lets you control the car, sitting in the other seat, that type of stuff.

What made you decide to go FedEx as opposed to commercial flying?

One, I was interested in flying for cargo. FedEx was, at the time, one of the more popular ones. But in commercial aviation it’s really who’s hiring at the time and a little bit of the luck of the draw. Part of it was they were one of the first ones to interview me so I got to make that choice first.

Do you get to spend time in the places you fly to?

A domestic system is anywhere from 12 to 24 hours off and sometimes there’s a weekend layover. I fly the international system, which generally is 18 to 24 hours off every time, and then once or twice within a two-week trip, there will be a longer layover, about 48 to 72 hours. So depending on where you land that’s a nice feature. Generally the airline tries to get efficiency by not leaving you in a place for very long.

What’s the longest you’ve been left in a place?

The longest I’ve been somewhere is five days. The best place was Hong Kong. I’ve had three days in Paris, I’ve had a couple days in Cologne, Germany. Most of them are pretty good. Singapore is another popular city.

Is that your favorite thing about the job — the opportunity to travel and see these places?

My favorite thing is actually just flying the airplane itself. I enjoy doing that. The travel is neat, and I’m a city person myself, so I do get to see some neat cities. Shanghai, Hong Kong, Paris — those are a lot of fun. But, personally, that’s not my major thing about it.

Have you had any scares or challenging flights?

Ninety-nine percent of them go smoothly. Once in awhile, you’ll get something where the weather might make it a challenging landing or takeoff. In the 16 years I’ve been at FedEx, I think I’ve had two occasions where something is broken on the airplane in flight where it made it a little challenging to land, but none of them were life-threatening and it worked out OK.

It’s not rare for something to break every once in awhile, but it’s pretty rare to have a major event where there’s a problem that might be life threatening. The landing gear is a hydraulic system.

There are actually three systems on the airplane and the main one that’s in charge of the landing gear was broken. The other two systems can pick up the slack for that main system breaking, but it just made it a little challenging. The gear comes down for a one-time deal and that’s it: You land and the airplane has to be fixed before you can do anything.

Most situations are accounted for when things go wrong, and there’s checklists for that. You basically follow the checklist. It makes it safe to get the airplane on the ground, then maintenance can takeover and fix the situation.

How do you deal with jet lag to stay alert in different time zones?

That actually is a very big problem in flying. What we do is we try to get our companies to make trips that allow for our circadian rhythm to work properly. An example of that would be if you’re a daytime pilot, you only fly in the daytime. If you’re a nighttime pilot you only fly in the nighttime — and you limit how many nights you do.

For me, I know what I’m doing the next few days in advance and I try to sleep properly so that I’m alert when I’m actually flying the airplane. Sometimes you may have a 24-hour layover, which means I have to stay up a little bit when I land so when I finally do go to sleep, I get a full night’s rest and I’m ready to fly. The wrong way would be like if I went to sleep right away because I’m tired, and then I wake up eight, 10 hours later, and now I’m up 12 hours before I actually fly. So now I’m actually going to be flying when my body wants to go to sleep. It’s a combination of making trips work well for our circadian rhythm and then just knowing how our bodies work and trying to sleep properly so that you’re ready for the flight.

What personality traits makes someone a good pilot?

I would say the most important thing for being a pilot would be common sense. Just being able to evaluate what’s going on and making decisions from that: not getting yourself into a situation where you actually need to run these checklists or you’re there when you shouldn’t be there, like a weather situation. Being calm is part of it, also. The ability to calm down, slow down, look at what’s going on around you in order to make decisions makes you a better pilot than someone who is excitable.

What’s the most unexpected part of your job?

I don’t think there are many jobs where the actual work itself is fun all the time. There are some days where it’s not fun to deal with stuff, but the actual flying itself — the actual work — is always fun. So even if you don’t have a good job, if you’re flying an airplane, you get enjoyment out of that. We’re one of the few industries where if you work in aviation, you almost never change careers, because flying is that much fun.

As technology changes, is the prospect of learning new systems good or annoying?

I’m more from a generation of computers and video games, so getting technology is exciting and actually relieves workload when we do that. For somebody who has been flying a little longer, from the analog age of flying where it was no electronics helping you out — for them, it’s a little harder. But I enjoy learning new stuff and the challenges with technology.