I had the good fortune of being allowed to be a mentor at the Unreasonable Institute this year. If you ever get the chance, it’s something you should definitely do. In my two days at the institute, I got to meet a bunch of amazing people who are making a real difference in the world.

One of the people I met was Paseka Lesolang, with whom I had a fascinating conversation on a Saturday night. Paseka, who was the youngest fellow in the program, was certainly wise beyond his years. Rather than pitch his enterprise or ask my advice, he simply asked me to talk about what I thought mattered.

This somewhat unorthodox beginning led to a two-hour conversation which touched on quite a number of topics, including real-life superpowers and how to make the woman in your life a priority when you’re an entrepreneur. But perhaps the most interesting point came up when Paseka talked about how accomplished us mentors were. Here’s what I told him:

“What you’ll find when you talk with people that are ‘successful’ is that most of us feel like we’re imposters. Even someone like Neal* probably thinks he’s not that successful.”

* Neal Baer, one of my fellow mentors, was the executive producer of ER, and of Law and Order: SVU. If being a famed Hollywood showrunner wasn’t enough, he’s also a graduate of Harvard Medical School, and in his spare time, travels to Africa at his own expense to treat sick children. Damn, that’s quite a personal history.

We have a strange and conflicted relationship when it comes to accomplishment and the accomplished.

On the one hand, we love to build up our heroes. Think of the hero worship we see of athletes, entertainers, and moguls. We want them to transcend human limits because on some level, that kind of achievement lifts us all.

On the other hand, we also love to tear down those heroes. Whether with tabloids (“They’re just like us!“) or unauthorized biographies, we seem to delight in finding feet of clay.

This ambivalence comes from trying to reconcile two conflicting ideas: One, the great are better than you or me…they have a special something that enables them to do great things. Otherwise, use normal folks have no excuse for our lack of achievement. Two, the great are no better than you or me…we’re not ordinary or inferior, just unlucky.

I suspect that the balance of this attitude shifts as we get older. The young, who are still bursting with possibility, prefer hero worship. There’s a reason that pre-pubescent boys and girls believe in heroes–for the most part, such achievement is still within their reach The trajectories of their lives are fluid, and their talents are just waiting to be discovered.

The mature have seen the possibilities of their lives crystallize. Many of the dreams you dreamed at 15, however unrealistic, are simply impossible at age 35, and might be laughable at 55. When that happens, it’s tempting to use the sour grapes approach. When Jon Ronson set out to interview Americans of all income levels, one of the things that stood out for me is the millionaire who tells him, “The trick is not to be too rich.”

I was reminded of this when I read Dave McClure’s essay, “late bloomer, not a loser (i hope).” Dave (very bravely, I think) tackles this issue head on. His opening line gets right to the point:

“most of the time I think of myself as a failure.”

He goes on to talk about his youthful dreams, his college experiences, and the ups and downs of his life in Silicon Valley. This section in particular I think helps capture the effects of the imposter syndrome:

so after twenty years in the valley, I had made only a little bit of money, and had some modest accomplishments as a programmer, as an entrepreneur, and as a marketer. meanwhile my peers at PayPal had gone on to create incredible businesses like LinkedIn, YouTube, Yelp, and Yammer, and other kids half my age were seemingly much more ambitious. most folks thought I was a decent fellow, but over the hill with my best days behind me… and I kind of thought so too.

Let me point out that we’re talking about someone who had worked for an enormously successful company (PayPal) and played a significant role at a number of other enormously successful companies (Mint and oDesk). By any reasonable standard, that’s success.

Yet we humans are unreasonable. And Dave had the odd misfortune of having worked at PayPal, which may eventually rival Shockley Semiconductor in its ability to generate entrepreneurs. It’s hard to feel successful when your friends have two or three more zeros in their bank account, along with a bevy of magazine covers.

The funny thing is, while the imposter syndrome harms its sufferers, it may help humanity as a whole. Our inability to prove ourselves to…well…ourselves seems to drive us onwards. Consider how Dave ends his essay:

and so here I am: still standing in the arena, in hand-to-hand combat with demons mostly of my own making, aiming to make a small dent in the universe. nowhere near a great success story, yet fighting the good fight and perhaps helping others to achieve greatness as I attempt a bit of my own. I’ll be 46 in a month, well past the age when most folks have already shown what they’re made of. but I’m still grasping for that brass ring.

I’m not giving up yet. I’m still betting my epitaph will read “late bloomer”, and not “failure”. wish me luck 🙂

I’ve known Dave since his PayPal days, because we were both SDForum (now SVForum) volunteers. And like most of the people I’ve known who’ve experienced success (regardless of whether or not he’d accept that assessment!), he hasn’t changed much.

Back in 2006, I wrote about another friend, Jeff Clavier. Jeff had just seen the first major successes for SoftTech, yet was working harder than ever before. At the time, I thought this was simply a matter of career optimization. Now, I suspect that the same thing drives us all.

So if you feel like a failure at times (despite what your friends say), don’t despair. Everyone feels like an imposter. And yet, this inability to consider ourselves “successful” may be the very trait that helps us (and you) keep succeeding.