Astute readers of OnMilwaukee.com may know that Sept. 1 is the annual anniversary of the day we launched. But before we flipped the switch back in 1998, we did a lot of work to get ready for that big day. I usually credit April 7, 1998 as the first day of OnMilwaukee.com, and that's exactly 10 years ago today.

April 7, 1998 was my first day of self-employment, and the idea of OnMilwaukee.com had been growing, in earnest, even before that. But I was the first of the three original owners to quit my job and make the Web site my primary career. Jon Krouse, who is still a business partner of mine but no longer works here, quit his job that summer. And the guy who sits in an office to the right of me, Jeff Sherman, joined in later that summer and quit workin' for the man about a year later.

I spent the first 24 hours of self-employment and OnMilwaukee.com at County Stadium, tailgating and enjoying Opening Day. I don't remember the details of the game, but I do remember that I was freezing and we sat somewhere behind first base. At that very moment, self-employment felt easy and liberating. I had lined up enough freelance gigs to hold me for months, and I actually remember telling someone that if everyone knew how easy it was to be self-employed, then everyone would do it and make me get a real job.

Ah, to be 23 and naïve again.

I also remember day two of OnMilwaukee.com, but the next couple years are a little bit of a blur. I woke up without setting an alarm, walked around the corner to Einstein's on Downer, and relaxed with a bagel and coffee. I didn't know it at the time, but that final relaxing week of bliss proved to be the calm before the storm. I had no idea what would lie ahead of me, and what it would take to build the city's second largest publication from scratch. I didn't know about investors or business plans or human resources or cash flow. I did know how to write, I had some PR and journalism experience, and back then, my Web design skills were as good as anyone's (which isn't saying a lot). I also knew I loved Milwaukee, and I wanted everyone to know it and why.

Most importantly, I just knew that it seemed like the right time to chase my dreams, and something good would have to come from it. My family and friends supported me fully, even if they didn't totally understand what I was trying to build.

Over the subsequent months and years, we transformed OnMilwaukee.com into a real business. We stopped holding meetings in my dining room and stopped keeping interns in Jon's basement. We eventually stopped making media calls from Jeff's employer's conference room, and gradually we started wearing pants to work. We hired great people, retained accountants and attorneys and signed leases and contracts. That little project we started from my apartment on Stowell began to grow up.

I guess, so did we.

On that cold afternoon at County Stadium 10 years ago, I didn't know where this company was going, but I figured that win, lose or draw, it would at least look good on a resume. I never really doubted that we would succeed in some way, shape or form, though most of the business community I encountered assured me that OnMilwaukee.com could never work in Milwaukee. Maybe I was just stubborn, because their doubt made me work harder. I know my business partners and investors feel the same way to this day.

I also didn't have an "exit plan" back then, which is something I now recommend to every new entrepreneur. At the time, we joked about selling the thing in six months and moving to the Caribbean. Obviously, that not only didn't happen, I quickly stopped wishing for it to happen. Now, I hope that if there's ever a further iteration of the product, it serves to make OnMilwaukee.com better, both for the city I love and for the employees I respect.

I used to say "work to live, but don't live to work," and while I still think that's a good mantra, it becomes increasingly difficult to separate my creation -- OnMilwaukee.com -- from my identity. There are a whole bunch of people who read my articles and blogs and know me because of my job. It's simultaneously flattering, stressful and eerie to be so public all the time.

That's the kind of stuff I didn't expect 10 years ago today. I didn't expect to have colleagues who would be working here for eight years. I didn't expect to ride in the limo with the president when he visited our office (and to receive the subsequent hate mail from people who never asked me how I felt about it). I didn't expect to have a few gray hairs at 33, and I didn't expect to still love Milwaukee as much as I do.

I'm fairly sure the next 10 years will look much different than the last, and this being the first thing I've ever done in my life for this long, I'm not ready to speculate on why.

Either way, it's been a good, wholly unexpected ride, and I don't regret one bit my decision to launch this thing. It's been a trip everyone should take, and I'm thankful that I've not only had my turn, but now I'm going on its second decade.