In 1996 my friend Chad and I launched a site called “When I Was a Kid.” We called it WIWAK for short. The page consisted of one-liners about things we believed when we were kids like:
“I thought fish lived in my cousin’s waterbed.”
Or:
“I thought those green power boxes at the end of my street were where they printed newspapers.”
Or:
“I thought the little thing hanging down the back of everyone’s throat was to separate food and drink.”
We posted our email address at the bottom of the site for people to submit their own WIWAKs, but nobody ever did, except for my sister, who confessed that she’d thought all dogs were boys and all cats were girls.
So not including me and Chad, the site had one visitor.
In 1997 I teamed up with my friends Rob and Tom to launch LabelZero.com. Our plan was to have artists upload music to our site for free and then, before users could download music, they would have to watch an ad or fill out a survey. Unfortunately, after we bought the domain name, the site stalled on my basement ping-pong table as we realized we had no idea how to approach companies, approach musicians, program the site, or do anything site related, in any way, at all.
Call it a case of ambitions exceeding abilities.
And let’s pause on that idea for a moment.
Ambitions exceeding abilities.
Because the thing so often missing from the conversation around ambitions exceeding abilities is the fact that it’s a good thing. That’s what you want! Can you imagine if everything you did was easy?
Being ambitious means you have artistic vision. It means you can imagine what the end product should look like even if you don’t know how to make it… yet. It means you have that hardest thing to develop, that thing that no amount of money can buy, and that thing more difficult than anything else to learn.
Taste.
It means you have taste.
And at the end of the day, taste isn’t all that different from vision. Taste means you know what you want, you know where you’re going, and now you’re just somewhere along the muddy path to getting there.
When ambitions exceed abilities it’s a clear sign you’re on the right path. It means you want your podcast or your book club or the softball team you’re coaching or the piece of software you’re designing or the surprise party you’re planning or the big report you’re preparing… to be better.
And it means you know how much better it can be.
Wanting to be better is a real gift.
It means you’re going to keep trying.
It means you’re going to keep failing.
It means you’re going to keep learning.
Sure beats doing a crappy job and being happy with it!
When I got to Queen’s University I spent most of my time writing for the campus humor newspaper Golden Words. And when I wasn’t writing for Golden Words, I was building websites.
I teamed up with a few friends in my business program to launch Ghettohouses.com.
That was my fourth website and it was the first one that gave me a tiny taste of success.
Everybody was complaining about the student ghetto surrounding the university. That was the name given to the thousand ramshackle houses full of raccoons and rats and covered with collapsing roofs and plastic tarps. The neighborhood was infamously run by a slumlord oligopoly, so my friends and I made a website where you could type in your address and write about your slummy rental. Properties could then be searched by landlord or by address, and over time, data from past and current tenants would add up to cases against the landlords.
We were going to help the people overthrow the system!
The site was popular enough that we got a couple hundred submissions. “Do not rent from Bill Lee!” a commenter would warn. “Our fridge at 105 Cherry Street closes with Velcro, our bathroom sink has never drained, and the upstairs bedrooms are on such a steep angle that my roommates are dizzy for an hour after they get up in the morning.”
We sold the website to the university’s student government for $1000 and split the money five ways. The student government promptly neutered the page to avoid lawsuits and changed the name to Student Houses, where every comment had to be approved first and nobody could say anything defamatory.
I was happy with my $200 but felt like a sellout and was frustrated the site died in the process.
Then came my blog on LiveJournal called Taut Twisted Tightness where I rhapsodized about the virtues of Granny Smith apples, chocolate Popsicles, and barbecue lighters. Guess what? Another failed site.
I’m on website five by this time. It’s around ten years after I first got my dopamine hit from Neil’s Haven of HTML and JavaScript and I was still searching for that next great high. Ten years! And those were just the sites I actually launched, not the ones I thought about and talked about with my friends all the time.
Did the pain end there?
Oh no.
For site six, I partnered with a former Letterman writer I’d befriended online to start up The Big Jewel. This time I paid a fancy graphic designer to create a brand and logo. We had a legitimate posting schedule—a new article every Wednesday! The whole thing was a knockoff of The Onion, McSweeney’s Internet Tendency, or The New Yorker’s “Shouts & Murmers.” We used the site to market our humor-writing services to magazines, newspapers, and other websites. Turns out appealing to a dying industry doesn’t work. Over the next three or four years, while we wrote, edited, and posted submissions, we received a grand total of zero inquiries for our paid services and maybe a few thousand total hits.
Six failed websites over a dozen years. Six failures before I launched my next website.
My next website was 1000 Awesome Things.
I had no idea at the time that this site would be the one to hit big. But it did. It won three Webby awards under the “Best Blog” category from the International Academy of Digital Arts and Sciences. It had over 50 million readers. It led to The Book of Awesome and a whole slew of sequels and spin-offs, all the way up to this conversation we’re having right now
My point?
Lose more to win more.