What To Do When You Feel Inadequate

There are times in life, usually when I’m struggling with a problem that I’m sure I’ll look back on as trivially easy, when I begin to feel a creeping sense of doubt in my own abilities.

I think to myself, “you are hoping to accomplish Big Dream X, and yet here you sit struggling to write a javascript program that prints out a chessboard”.

Concerns of this sort can be very difficult to brush aside, but when they happen to me, there are a couple of things I try to keep in mind:

1) Everything I’m good at I used to not be good at.

I don’t think it’s unfair or overblown to say that at the peak of my guitar playing abilities I was just a little shy of world class. Around the age of 21 or 22 I could easily handle Andy Mckee’s “Drifting”, and I even had a pretty convincing cover of Eric Johnson’s seminal “Cliffs of Dover” under my belt. But where I really dazzled was in my original compositions which, if you’ll permit me the indulgence of tooting my own horn a little, displayed a sensitivity and nuance that almost everyone who heard them found striking.

That’s not an assumption on my part. Back then it was a regular occurrence to perform at some college event and then be approached by a half-dozen people asking me questions and gushing about how they’d never heard anyone as skilled as me play in person.

Which is why it became easy, even for me, to forget how bad I was when I started and how hard I had to work to achieve what I did. I think I had been “playing” guitar for about two years before I even began to seriously practice. Even then, while my progress was fairly quick, it was far from spectacular.

The same guy who went on to excel musically spent many, many frustrating hours trying to get graceless fingers to coax something vaguely resembling music out of an uncooperative piece of wood. Perhaps the same guy who goes on to found a billion dollar company or helps reshape the foundations of AI theory will look back on those simple coding exercises and wonder why it ever seemed so hard.

This helps me put my struggles into context.

2) Constant failure is the price you pay for greatness.

A great way to avoid failure is to simply never try to do anything very hard. I could just start working at a Barnes and Noble, wait until I’m in middle management, and stay there for the next half century, and I bet I would experience very few embarrassing failures.

Since I’ve deliberately chosen not to take the easy way out, there’s no avoiding the fact that I’m going to bump up against my limits. I’m going to embark on a project that’ll wind up being too ambitious and at some point I’ll simply crash and burn.

But so what? Point me to anyone who has achieved great things, like solving a longstanding problem or remaking an industry, that also managed to avoid failure while they did so.

Can’t think of any? Me either.

The tricky part, of course, is remembering this when you’re actually in the middle of an ongoing crisis and you’re beset by self doubt.

3) Titans rarely feel like Titans

Sometime last year or so I was reading “Almost a Miracle”, a history of the Revolutionary War by John Ferling. It was fascinating overall, but one thing that stuck out was the insight it gave me into the personality of George Washington.

Washington is about the closest thing American history has to a mythical figure. And yet he spent his entire life feeling insecure because of his lack of formal education, and he repeatedly questioned his suitably for the role he was asked to play in the war.

This is the man that went up against one of the greatest empires in world history and won, all while unsure as to whether he had the personal resources, wit, and wherewithal to succeed.

Why should I expect my own accomplishments to come easily?


I’ll level with you: you’re going to fail. You’re going to feel inadequate. That’s what happens when you hold yourself to a high standard and reach for the best within you in an attempt to accomplish big things.

You have to know when to throw in the towel, of course; not every idea is worth pursuing. But the majority of people I’ve encountered err on the side of quitting far too soon. Finding someone with sub-optimally high levels of persistence and grit seems to be pretty rare.

There’s another thing I remind myself of, as a last resort, when I feel like giving up. It’s not something I say often or when I’m feeling depressed, but it’s nevertheless true, and sometimes you have to be the person who’ll say the tough things you need to hear.

After a while spent futilely groping toward a solution to a problem, when I want to just let go and sink into mediocrity, I’ll think to myself:

If this is all it takes to break you, you would never have been worthy of greatness anyway.

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