On Breaking In Shoes and Breaking Out of Your Comfort Zone

I recently bought a pair of plain-toe, leather, derbies (cognac). They’re lightweight, sharp and apparently well constructed. But they need to be broken in. Walking back to my office from lunch, they feel rigid and awkward. Life can be like that, like a new pair of shoes, especially when you’re trying something for the first time.

Early last year I started piano lessons. I’ve played for years, but I never really committed myself to formal training until then. For the first few months, my forty-something-year-old fingers had minds of their own. Despite my earnest effort, they did whatever they wanted. The process felt cumbersome, awkward, embarrassing. But my vision was so clear. I saw myself being able to one day play freely, and in doing so, feel a new kind of freedom. I wanted it so bad, as awkward and embarrassed as I felt, the process seemed worth it.

Three years ago I began the journey of opening a real estate agency. The opportunity to create a business, and build a business culture, that could add something truly useful to the lives of consumers was (and is) an incredibly attractive prospect. At the same time, it was impossible to know what waited on the other side of the decision to venture out on my own. People fear the unknown for good reason. Real pitfalls and boogie men hide in the dark. So one of the most difficult aspects of running the business has been the stress of uncertainty, which can at times feel overwhelming.

So often I feel like a child,
fumbling in the dark,
learning to see a new room
with new hands.

I sense mastery,
a new kind of freedom,
then I kick some hard, hidden thing,
all but breaking
my big toe.

But I keep moving. I keep groping and growing. I keep stepping. I try running. I struggle, catch my wind, find my rhythm and settle in. I adapt. I learn how to rest on my feet. I keep going because I believe the hardest lessons are indispensable, and the hardest progress is most precious. I keep going because if I quit on the things I care about most, I will never know the true extent of my potential. Plus, these dreams of mine seem bigger than me. So this work, and my sacrifice, has purpose, and the process feels worth the discomfort.

Side note… For those that don’t know, I hate to break it to you. I hated to break it to myself. There is no secret to success. There are no shortcuts. Real success, which is almost all about realization, is rare (and so valuable) because it’s so hard to reach. And despite what people say on YouTube, in self-help books and self-hype seminars, there is almost nothing worth having that doesn’t involve sacrifice.

Breakin’ ground invites sacrifice,
and pain.
And if you walk in ‘em long enough,
breakin’ shoes is the same.

But some shoes won’t break. Maybe it’s because they’re too small. Maybe it’s the material. You know, some fibers won’t give. But a good pair of shoes, made of the right stuff, will start out snug, and as you walk, find a way to fit your feet. You’ll never know if they’re good until you try them on. And even after you try them on, you still won’t know. You have to live in them, test them. You have to try to stretch them.

I’m not exactly where I want to be on piano, but I see progress. I’m stretching the figurative shoe and beginning to realize my vision. The same is true in business, and, I guess, with these shoes. They’re starting to give, but my feet hurt. Folk ain’t got to know my feet hurt. But maybe they should. Maybe you should know what I know.

Just because something don’t feel good,
don’t mean it ain’t good.

Leaving your comfort zone by definition invites discomfort. Life teaches me this over and over and over again. I can do amazing things, but like these new shoes, I have to be willing to give. Like these shoes, that doesn’t mean I have to give up the core components of my character, or the best parts of my personality. But to realize my vision, I must yield substantially to the inherently unpleasant process of having my thinking and behavior reshaped.

I can be in pain
and be exactly where I’m supposed to be,
on the edge of defeat,
on a road to victory.

Maybe I’m too idealistic. Maybe I’m naive. I admit it, in part I’m both. But I’d rather be too idealistic and naive than too safe. And I’d rather keep trying new shoes until I find a good pair.

I know what it feels like too,
‘cause I’ve owned a few.

I bought ‘em,
broke ‘em in,
put miles on ‘em,
that’s what I do.

With good shoes,
that’s what I do.

You won’t find ‘em in a closet,
lingerin’ bout.
I wear ‘em outside,
wear ‘em flat out.

With good dreams too,
that’s what I do.

I take ‘em out the closet,
chase ‘em out the house,
chase ‘em round the corner,
wear myself out.

With good dreams too,
that’s what I do.

I like these shoes. They look good. They make me feel good too. Or, better put, they make me feel good everywhere but my feet! But who knows, maybe they’ll break sooner than I think.


-Billy Ross

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