On dreams and privilege.

At Brooklyn Beta earlier this month, I had the opportunity to participate in a conversation led by my good friend Wesley Verhoeve about the relationship between privilege and the ability to follow one’s dreams.

It was jumpstarted by a talk that Elle Luna gave (based on this great post), in which she extols the virtue of following our passions — of, as she puts it, choosing the things we “must” do over the things we “should.”

Must is who we are, what we believe, and what we do when we are alone with our truest, most authentic self. It’s our instincts, our cravings and longings, the things and places and ideas we burn for, the intuition that swells up from somewhere deep inside of us. Must is what happens when we stop conforming to other people’s ideals and start connecting to our own. Because when we choose Must, we are no longer looking for inspiration out there. Instead, we are listening to our calling from within, from some luminous, mysterious place.

She concludes:

Because there is a recurring choice in life, and it occurs at the intersection of two roads. We arrive at this place again and again. And today, you get to choose.

So, a dozen or so of us — techies, designers, VCs — sat around with Wesley and Elle and discussed her experiences along with the benefits (and risks) of pursuing one’s passions. I enjoyed talking with Elle. She’s smart, passionate, and persuasive. And she’s not the only one. Hers is just one in a growing chorus of voices celebrating self-fulfillment.

For example, in his opening statements from the conference, Chris Shiflett touched on a similar note. He mentioned that in addition to simply crafting solutions for our clients, we had the ability to do something else, something more:

We do a fair amount of client work ourselves, and we have a great deal of respect for everyone who focuses on solving other people’s problems. But, there’s room and opportunity to work on your own ideas, too.
I love the Internet. I think it’s the opportunity of our generation. I just think that it would be really great if this room full of amazing people had a hand in where we go from here.

I don’t know Chris personally, but he seems like a good guy. And I genuinely applaud the ambition behind that statement. But “generation,” I think, is a really poor word choice there, and he even sort of hits on that. It’s not the opportunity of our generation; it’s the opportunity of the sorts of people who happened to be in that room. It’s the opportunity of the folks who can shell out $300 for a conference without thinking twice (or whose employers will do it for them).

This hits at something I’d felt throughout the conversation that Wesley led. It seemed to me that we were largely glossing over the fact that it takes a heck of a lot of privilege to have the time and resources to chase after your dreams. For a large segment of the population, the word “unfulfilled” simply isn’t in their lexicon. They’re too busy trying to make rent, or to feed their kids, or just to hold down a job. There’s often not a lot of time for dwelling on ‘what if.’

Despite best efforts, I will, unfortunately, never play for the Boston Red Sox.

I’m not for a moment suggesting that dreams are a right reserved for a select few. What I am saying is that for many if not most of us, there’s a point at which you age-out of certain aspirations. You might have wanted to make pottery or go to Juilliard, but if that didn’t happen by a particular age, chances are it never would. And, as you took on more responsibilities, you had to learn to accept that unfortunate fact and find another path.

Now, a certain level of privilege, or success, or — let’s face it — money can afford you the ability to either extend that runway, or recapture it. It gives you the freedom to wonder. Simply put: It’s a heck of a lot easier to chase after your dreams when you’re not worried about keeping the lights on.

We’re not breaking any new ground here. I know.

And that’s sort of my point. Why can’t we just admit that? Perhaps I’m wrong, but it seems like a lot of the time, the folks telling you to follow your dreams are in pretty sweet positions that have allowed them to do so. I certainly don’t begrudge them that, but we fortunate few tend to all too easily forget the fact that we’re fortunate.

Rather than so quickly ascribing our situations to everyone, can’t we just take a breath and be thankful for a minute?


“Fuck it. I’ll just go and make axes.”

— A surprising number of people


I’m not sure if it’s a backlash to the last decade-plus of grand-scale corporate malfeasance (see: Enron, Madoff, that whole global financial crisis thing), but there’s been a noticeable move among the creative class towards artisanship.

More and more often, we hear of someone we know leaving their job to focus on something less governed by staring at screens in the search for a more “authentic” experience. Folks are becoming butchers, or leatherworkers, or brewers. And I’m a huge supporter of that. But it seems that we’re so wrapped up in this kinfolking of existence that we’re losing sight of the fact that the people who have historically done those jobs weren’t necessarily pursuing their passion; as often as not, they were just trying to pay the bills.

Is that a reason for someone with a little bit of money in her pocket not to pursue her dream of making the best damn whiskey you’ve ever tasted? Of course not. I’m merely contending that those of us who are blessed with the requisite combination of luck and determination to make those sorts of changes need to stop acting like we’ve seen the light, that we’re somehow superior.

Like anything else, it’s not the belief that gets you in trouble — it’s the proselytizing. One way of existence isn’t necessarily better than the other. Similarly, having the guts to quit your job to focus on making bags, or bikes, or booze is amazing. But it’s not an opportunity that’s open to everyone.

My grandfather’s father used to gather us around the fire and tell us, “Never miss a perfectly good opportunity to shut the fuck up.” Okay, maybe that wasn’t great-grandpappy Ippolito. Maybe that was someone else. But it’s still true. (And, yes, the irony of using 1,400 words to say this isn’t lost on me.) Basically, I love that some folks are able to follow their dreams. I guess I just wish we’d stop pretending we’re doing God’s work.

(Okay, in retrospect, making whiskey was a bad example. That is absolutely God’s work.)


Can everyone make that choice?


Back to Elle and our group discussion.

One of the things I most appreciated was her understanding that simply quitting your job and storming off into the sunset isn’t necessarily for everyone. In fact, she mentioned that having a nine-to-five can be a fantastic way to finance the pursuit of a passion.

But I can’t help but wonder if that leaves us back at the beginning. Do most folks even have that freedom? Once the day job is done, how much time and energy is left? Don’t get me wrong: Some people have unbelievable amounts of hustle. But some also have unbelievable amounts of responsibility as well (family obligations, a second job, etc.). You often hear that “you’ve just got to want it bad enough,” but it’s almost always said by someone who already has whatever “it” is. The simple truth is that it’s not that easy for most people and our reductionism is myopic and unfair.

Again, it’s not that everyone shouldn’t have a dream; it’s that those aspirations often end up taking a back seat to more practical matters. And that’s okay.

We tend to take our positions for granted. And I’m just as guilty as anyone. Every time I catch myself complaining about my comparatively cushy job in one of the world’s great cities, I think “Right. Working in tech is really rough. And they don’t make good yachts anymore.” The point is: I do it, too. I just wish we‘d all do it a bit less.

Of course we should follow our dreams. But for many of us — the digitally-minded, conference-attending, Medium-reading design & tech set — the words can fall a touch too easily from our lips. I’m sure we don’t mean to naval-gaze, but it can come off that way. It’s a message with a good focus; we just need a wider lens.

We’re so damned lucky. Do we need to be so egoistic to boot?

During her presentation at Brooklyn Beta, Jane Ní Dhulchaointigh, the inventor of Sugru, had a slide that simply said: “You don’t need to be an expert. Learn it.” And perhaps she’s right. I don’t know if any of us will ever be great at it, but maybe while we’re doing all this self-actualization, we should at least try to invest some time in learning a bit more self-awareness.