One question that I’ve gotten many times over the years is how exactly I got started in web work. There are several ways to skin that cat, but for the purposes of what is actually useful to my Young Lions looking for their first real job, I will go about the strategy and situation in which I got mine, maybe it can help you with starting out.

The fast wiki is that I come from a small business background, family owned situations, and had been in the culture of self-employment and independents from the age of 12. My parents are good midwest folk with a solid work ethic, and I was encouraged from a young age to hunt out odd jobs and create my own situations.

I was in my 3rd year of college at my 2nd school, majoring in Sound Engineering and Acoustics at Columbia College of Chicago. Big dreams of the hip hop world, very active in a community of artists, musicians and creators. In 1999, the internet was a much smaller and simpler space, primitive by today’s standards, but the sense of it being The Future was ubiquitous in our culture at the time. And I knew that I wanted to be a part of it.

Lots of kids I knew were jumping into proto digital creative roles, when “web designer” was the blanket label that covered a dozen skills and disciplines. Many of these had no analog in the era of analog, it was a while before a common terminology came into play. There was the wonderful feeling of it being a wild west, a frontier that belonged to our generation.

Research and Development

Looking at everything happening in this baby internet and this emergent web designer culture, I must have reviewed two hundred websites. Search engines were a shallow pool then, you’d find the best work via the best work, there was a practice of cross linking and cross promoting. Web talents were proud to show off their peers as much as themselves. It remains a beautiful practice, more should adopt it. I educated myself on the market that I was jumping into, and figured out which niche I wanted to attack — the quirky oddnick.

I had no real work to show, everything in my folder was experiments and tests. I decided that my first web presence would be a demonstration of what I had learned in these proof-of-concept builds. I planned a pronged attack of presenting my starter content through 3 distinct, cross-linked websites. The user experience was much like the portals of the time, microsites that felt felt like a single piece of a larger network.

So, the first three sites that I pushed into the market with?

• Untitled aka “Box”, the first site I designed had a boom box for navigation.
• Peyuco’s House of Sin, a parody of early porn sites (build what you know).
• Syndicate University, a parody of college websites (attack what you despise).
• And a landing portal for my root url, three options for three channels.

On each, the overall frame is a separate pseudo site, but with enough shared content that it wasn’t all lorem ipsum. They were nothing exceptional, definitely limited, but I had the confidence to put them out there with my name attached to them, and start hollering at companies with nothing but my balls and my word.

“Do you see the beast? Do you have it in your sights?”

The criteria in my mind for pitch-worthiness was very simple, and became a basic precept that I retain to this day: the question of whether or not the site I am looking at is something I could build. If the answer was YES, I put that company in the “contact first” pile. Design companies whose sites were more impressive than anything I could do went into the “contact second” pile.

The pitch for team Contact First was fairly straightforward:
1. I’m a young web designer looking for regular work
2. I’m a student and may need morning / afternoon flexibility
3. Here is the work that I have done

No mention of their work. It was a form letter that I sent to approximately 60 companies.

The pitch for Contacto Segundo was a little more meaty:
1. I’m a young web designer looking for regular work
2. I’m a student and may need morn / aft flex
3. Here’s the work I done and chekkit
4. What I LOVE about your website
5. What I LOVE about this one thing you did
6. I really want to work with your team
7. I know I’m not jack shit but please gimme a shot

Acknowledging their work but trying waaay too hard to sell myself.

Zero surprise that the bite back that actually lead to my first job came from the Contact First pile… nature abhors the overeager puppy. It is good to swing high and hard though, you never know what can connect.

The company that I went in for was, like many at the time, a traditionally based services provider that was trying to transition into an online entity. My head was full of 19th century concepts about employment, in my interview I was all of the things that they would not see again in my time working there: clean shaven, in a dress button down, enthusiastic about being in their office. But I was hungry and I wanted it. They hired me.

I got in on sheer confidence and an ability to bubble about the potentials of the internet. They had a need to go online and wanted a young lion that they could quickly bring up to speed on the particulars of their business. Together we were going to figure out how to best build websites in the B2BR market, it was a learning experience and uncharted territory for all involved and we all knew it. It was the first and last job that I had in the internet as a full time employee, in the time since I left them in early 2001, I have worked as either a straight up freelancer or a per-term / per-project contractor.

Looking back on it 15 years later and seeing both the tight footwork and missteps in that particular dance, I remember all of the pressure and excitement to get that first claw in the cliff. It’s such a great time in your career, everything is wide open in front of you. And I can’t lie, it’s cool to be young money and shine a little bit. We had fun.

But in a full post mortem of the experience, I bring the following to the attention of my Young Lions.

1. Learn your market, see who the local talent is. Know that your colleagues and your competition are one in the same. If you want to work as a designer, see what top design looks like, then try your best to emulate it. We all find our voices through mimicry, all great guitarists start out playing their favorite songs.
2. Don’t be a dick about whatever little thing you’ve achieved. If you’re cold-calling on a company that is clearly in a higher league, be humble. Do some research into what they’ve done, express interest and intelligence. Do not brag. Nobody cares about your _____.
3. Have confidence. This is not an industry that rewards the timid. If you feel like you can do cool and interesting work, make your online presence your project. Show the world what you can do, starting with yourself. If you can actually do the work, people will notice.
4. When all else fails, bullshit and ramble. Show that you think, you live and breathe these projects. People love passion, and a lot of the time you can get yourself a spot just by showing a lot of drive and motivation. You can get a six month or a full time off of sparks in an interview, just be careful to keep hubris out of the conversation.

Good luck!