I like to think that I’m not sexist, but my reputation may precede me.

At some point during my college years, I started using a reverse-psychology approach with women I knew (usually girlfriends) – telling them they couldn’t do something – in hopes that they’d be motivated to prove me wrong.

Ask my wife – this is the wrong approach. Reverse psychology only works on a certain type of person, usually enemies, and (hopefully) they’re not the majority. People want to be built up, not torn down. The other bad part of this reverse-psychology habit was that as I told women that they couldn’t do something, I was slowly and subconsciously telling myself that they couldn’t.

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Disclaimer: this is not meant to offend any Mormons. My wife’s family is predominantly Mormon (though we are not). However, I’ve witnessed several of her cousins announce their engagements after only weeks of dating. And their wedding date was typically 3 months out from there.

I would never plan a 3 month-long engagement because I don’t think it’s enough time to plan a decent wedding and maintain your sanity. Weddings only happen once (if you do it right). Get it right the first time.

Like young, naive lovers, WordCamp organizers also need to suppress their hormones. We tend to get over-excited about WordPress – like evangelists that have been given a free podium. Pocket your emotions, and follow the advice from those who have come before you.

This post could serve both groups as a guide on how fools rush in. It’s possible to plan something this big in 3 months, but believe you-me, it is much less stress to take your time. I wish we had followed this advice – but we didn’t. In 3 months, despite the odds, we still managed to pull things off.

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This article’s concepts should be considered independent from the layout of your business: whether it’s a sole-proprietorship, partnership, LLC, etc. We’re only talking about how you file your taxes. This article is also geared towards freelancers, subcontractors, and small companies.

Schedule C

For most people getting started on their own, there is the “Schedule C.” You pay your 15.3% Medicare & Social Security, plus your income tax quarterly, and hope everything works out on tax day. This is a great way for anyone to feel the “pain” of how much you actually pay in taxes. It can hurt so much that you’ll wonder if there’s a better way, and there is. Enter the S-Corp.
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I have the privilege of living walking distance from a bus route that has served me well for most of my time spent in the Twin Cities: The 10. When I was a kid growing up in Northeast Minneapolis, my dad would take me to Twins games downtown on the 10. Now in Fridley, I can still take it to any number of businesses along Central Ave. I can also head downtown and make any number of connections. The 10 runs late into the night, so I can even take it home after a long night of imbibing.

However, my closest bus stop (Central Ave. & Gardena Ave. by Moore Lake Beach) is a pedestrian SNAFU, no thanks in part to Fridley’s city planners.

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