Two important lessons that have molded my life a bit only after failing at them many times:

  1. However good you think you are at something, there’s always more to know. And you should never stop trying to know more.
  2. Thinking you’re good at something is arrogance if you don’t walk the walk. It’s not about proving it to someone else, but avoiding the wither of a life out of sync with your estimation of yourself.

I think the saying “You are the sum of the five people you spend the most time with” is probably true. The most obvious reason is that we pick up mannerisms, thinking patterns, and beliefs from those closest to us. But in my opinion it’s also in how we see ourselves in the reflection of these people.

Not in a basic way like “I know smart people so it makes me feel smart.” More like how you challenge yourself and what degree of anything is good enough.

Here’s a personal example. When I first got into freelance writing and was busy sampling the business world, I fell in with certain people. I had vague aspirations about what it meant to be successful in business or what it would look like to have “made it.” This understanding drove where I spent my time. In that crowd, everyone was assumed to be a master of their respective industry (regardless of merit). It was nice at first to have that sort of pseudo-respect, but it made me lazy.

“As writing goes, I’ve got this,” I told myself. I thought all I needed to do was learn more about business in general and I’d be golden. Like an athlete arrogantly spending more time being proud of his fitness than actually maintaining it, my creative muscle grew fat and easily winded. Fresh out of college, putting way too much stock in that fact and innate skills.

That led to one of the longest dry spells of my life, and with it one of the deepest depressions. The same vanity that brought all that pride was quick to create a vacuum of self respect.

The Inner Circle of Walkers vs. Talkers

Years later it was clear why that was such a bad environment for me. I may have been the best writer and thinker in that bunch, but it wasn’t saying much. I’d been both an asshole and a coward.

The bar was low in places it needed to be higher, and yet my perception of their success really messed with sight of my own. None of us deserved the pedestals we put each other one, or at least paid lip service to. But the pedestals bred a lot of inferiority — often intentionally. Our respect for each other was as shallow as our willingness to walk our respective walks.

When other more supportive and more talented people came into my life it changed. Subtly at first, but at some point later there was a clarity that made my memories seem unrecognizable against the present.

It’s made me push myself far harder than ever before. For awhile I felt starved for information, and even when I hit some limits of the most I could possibly give per day it was inspiring. I was raw with myself and the limits illuminated how far I could stride. It’s easy to overestimate your limits if you’ve never pushed against them, and you might be pleasantly surprised when you do.

Having a stronger inner circle makes me want to do more, and not out competition or fear of inadequacy, but of a genuine inspiration to strive for things the way those I admire do. The bar is raised, but in a way that is inviting rather than threatening. The more I studied those ahead of me and learned from their struggles, the more human the whole thing seemed. The focus became how I could constructively push myself harder and reflect less on perceived failure.

I say perceived because with a lot of the things we think we’ve failed at the most, we succeeded more than we thought we did. And even where it was more loss than gain, the scar is more superficial than we imagined.

Embrace, But Let Go

We have to be fluid with our inspirations. There have been blogs, for instance, that I’ve followed for years because the writing was beautiful. I was envious of their ability to weave words and stir things in me. Eventually though, as some of them found success they became more about selling the idea of beautiful writing than actually creating it.

I’m not judging because hey — if that was the idea of their site all along really then by all means. But it no longer works as a source of inspiration for me, and that’s fine. For every writer or creative person I lose sync with I discover another that shapes me differently (and just as profoundly).

The takeaway is that it’s not in our nature to examine those closest to us or where we spend our time. But it’s important that the answers to those questions are in line with our dreams and our values, otherwise we compromise ourselves with the status quo. I believe that when we feel the most comfortable is when those questions are most important.

What do you think? How have your motivations changed over the years, and where did that inspiration for change come from?