Taking 11 Flights to Alaska and Back

Self-employment is scary. But so is life. That's okay. It's good to scare yourself sometimes.

I’m not a natural-born thrill-seeker, but I do try to live by the quote: “Do one thing every day that scares you.”

Being self-employed is something I talk about all the time, and many times, people say “I could never be self-employed. It’s too scary.”

I completely understand this. People love having a steady paycheck, a reliable work week, benefits, the opportunity for advancement, occasional raises in pay, and maybe a week or two of planned vacation every year. I don’t have a problem with that if that’s what they’re into, but at this stage of my life, that just sounds… so boring!

When I started my first company after losing my job, the illusory bubble of “security” popped for me, and I realized just how fragile life, employment, and safety are.

But this whole concept of “having a job” that can provide security is, in fact, a complete farce.

I’ve been laid off from three separate companies in my life, never with any warning, and my final conclusion from all those experiences is: “I was just really bad at taking the hint that employment simply wasn’t for me.”

I don’t know why I kept pursuing it so many times when I should have just accepted it and moved on. I think it took me so long because everyone else had a “normal job.”

Very few people I knew worked alone. Almost everybody in my social circle worked for other people, and I just figured I would—or should—be like them.

I chased the security of a steady paycheck and an office job where I got a door with my name on it, business cards with a company logo that said “director” on them, and all the trappings that came with it: gym membership, parking spot, and the like.

It was fun while it lasted, but it never did last, and I’ve finally gotten wise to that.

Losing your job is like going getting a root canal or going through bankruptcy: once the thing you fear the most finally happens to you, you say, “Well, that sucked… but it wasn’t so bad. I survived. I’m still here.”

In fact, the fear I had for “the worst thing that could happen” was worse than “the worst thing” actually happening.

Yes, it was very scary. But I survived, and I’m still here.

I’m not exactly “fearless,” but I’m really not afraid of much anymore. These days, I even get bored when things are too settled, so I do things to scare myself again.

One of the best things about being self-employed is that I have the ability to frighten myself on a regular basis.

For example, I’m afraid of flying: almost terrified, really.

But last year, I had an opportunity to take a work trip to some of the remotest areas of Western Alaska. This required 11 separate flights to get there and back, and that was a frightening prospect.

Six flights to get back

From Alaska to Arizona

Even though I felt sick in my stomach at the thought of what lay ahead, I said “yes” because it was worth it.

Going from giant jets on Alaska Airlines all the way down to tiny little single-prop utility planes landing on gravel runways out in the middle of nowhere was really pushing my limits.

But I said yes anyway. I took the trip and braved the flights, and I survived.

(The clip below is just one of the many flights I took on a tiny plane in a small, remote Alaskan village. They pretty much all look like this).

The whole thing was a good experience. It didn’t entirely cure me of my flight anxiety, but after flying something like 12,000 miles, I’m not really afraid of that anymore.

Do things that scare you.

Say yes to opportunities that come along, even if you’re afraid of what you have to do in the meantime. You can do it!