The Great Big Barrier and A Comfy Chair

Wenatchee in the winter from the top of Castle Rock

I imagined a barrier. Yes, this is going to be heavy on the metaphors. I apologize in advance. A Great Big Barrier, in fact, as the title suggests. An imposing, literal wall. We’ve all faced one, have stood in front of it. A job interview, for instance. A marriage proposal. Standing on skis for the first time as an adult. At least once, many times no doubt, we’ve all broken through. What pushed us to face it in the first place was something inside, us telling ourselves whatever the current Thing we were doing was no longer enough. We needed more. A different job. To share our lives with someone. A way of learning humility after falling on skis and looking up to see a five-year-old cruise past hollering ‘wheeee!’ 

So we stood up, faced this Great Big Barrier, and somehow broke through. What, then, was on the other side? To continue with the metaphors, just waiting all inviting-looking, was a chair. Hmm, interesting.

I needed to, what did I tell myself, decompress? Time for a trail run. The valley was half-covered in shade, half-bathed in sun. Shadows were growing longer. It was cold outside, crisp. 38 degrees. Gloves and hat weather. Our teenager had left for work a few hours earlier. The toddler was asleep upstairs. I kissed my wife as she shooed me out the door, herself bundled under blankets and a laptop, hard at work.

On every run, I like to give myself a theme. This usually comes in the form of a question. Today’s: What’s my biggest challenge? I ask this of everyone who shows up to a Sendline event, so it only seemed fair to ask it of myself. Not surprising to me, I answered in one word: Myself. Whoa. What did that mean? In my attempt to figure it out, I ended up imagining that barrier as I chugged up Castle Rock.

There are as many examples of this metaphorical wall as there are us. The one I thought back on was getting offered a job as a cashier for REI seventeen years ago. I had grander visions of becoming an REI photographer and figured this would get my foot in the door. I had just started climbing mountains and I wanted cheap gear. Oh, and I had just been laid off from Kodak after they missed the digital photography boat. Out of eight-hundred-some-odd applicants, I was one of the sixty-ish who got the good news. I broke through, and it felt awesome. I still remember.

Then, beyond it, was the chair. The Comfy Chair. I didn’t sit in it right away. There was a lot to learn. After all, I didn’t want to work in the store, I told Chris. Yep, there was that dream to be a photographer, which never ultimately happened. No matter. I ended up taking a different path, where I met a lot of cool people and learned a bunch of really fascinating things. Had tons of fun. Eventually, after a lot of work, it was inevitable. I sat down, in the Comfy Chair. Still a metaphor, in case that wasn’t obvious.

The chair, to be clear, represents mastery. Confidence. The hard-earned kind that only comes after years and years of experience, after doing something a thousand times. I had been at REI for nearly sixteen years, after all. That was an awful lot of experience, and with that, I had developed a great deal of confidence. That’s a good thing. Experience is pretty nifty that way. Even cooler: This is how it works for all of us. We gain confidence, reach mastery, and need to be challenged again. So at some point, we face The Great Big Barrier. With a delicate combination of luck and fortitude, we break through, to do it all over again. 

We all deserve to enjoy the expertise we’ve earned, the comfort of sitting in the chair. For some of us, at some point, that’s enough. For others, it’s never okay. And for those of us somewhere in between, it’ll hit us all of a sudden that we’re comfortable and need to do something new.

The moment I realized how comfortable things had become, I knew I had exactly two options: Sink into the chair deeper or get up. There wasn’t a third. There never is. Right there in front of me, though, was another Great Big Barrier. Hmm. Damn. Even so, I needed a new challenge. I had to get up. Outside of the metaphor, for me this meant saying goodbye to a lot of friends, the place we had called home for a really long time, and a way of life I had gotten used to. Back inside the metaphor, it meant saying farewell to the Comfy Chair.

Right away, I of course hit that stupid wall. Ouch. It hurt. Hmm, I didn’t remember it hurting that bad last time I ran into it. Oh wait, that was sixteen-plus years ago. I was younger then. But that wasn’t why it hurt more. That was the metaphor. It hurt more, I realized, because I still had the same expectation of mastery I had while sitting in the comfy chair.

Aha! There was my answer to the question I started with. Why I’m my own biggest challenge. It’s because I still expect to know all the things. The problem? On the day I left REI I had sixteen years of experience. That’s a lot. The day after, I had zero. Zero years, zero days. Nada. I had never run my own business. I was starting from scratch and expecting mastery. Yikes. So when I failed, which I have a lot since that day, it sucked. A lot.

I got to the top of Castle Rock. The sun, still warming the Columbia River below, Badger Mountain beyond, was just disappearing behind Twin Peaks. I watched it go. It was cold in the shade, not moving. Time to get going. It was all downhill.

Was there an answer then to my answer, I wondered? A way to be less of a pain in the ass to myself. Obviously, I needed to figure out how to drop the expectation I’m going to nail every conversation, every presentation, everything I do to develop Sendline. Duh. That’ll be tough. I can do it, I know, especially now I realize that’s what has to happen. 

Thinking back to my silly metaphor, I recognized there’s no definitive, dramatic thing that separates success and failure, comfort and awkwardness. It’s all an illusion, the Great Big Barrier. The breaking through is more often found in the little wins that happen every once and a while. A great proposal. A killer conversation. A goal I finally meet that had been on my whiteboard for a while.

Eventually, slow and sudden, there’ll be no figurative wall right in front of me anymore. I won’t have noticed it disappear. There’ll be a chair, though. I’ll sit down, at least for a little while. Enjoy the experience I’ll have earned. Drink some coffee. Just beyond it, definitely noticeable again, another barrier. What then?

Friday Randomness, Vol. 1

People aren’t afraid to fail. They’re afraid to fail alone.

This is a quote a friend of mine shared with me. It sort of stopped me in my tracks.

She’s right. No one wants to be out alone on a limb. In a culture that isn’t keen on risk, being the only one standing up for someone, or a thing in which you believe is that much harder. It takes guts. A lot of guts.

The thing is, knowing someone has your back or having someone with whom to share ideas, makes it a little bit easier. And a little bit is sometimes all it takes to become the one setting an example, inspiring others.