Old School

Sometimes Old School Rocks

Breakin' by Ms. Phoenix, on Flickr

I'd like to tell you a story. Every January growing up, a little cardboard envelope would come in the mail addressed to my dad from Intuit software. First it was a floppy diskette. Then later a CD-ROM. The arrival of each of these signaled that annual process dreaded by most Americans: filing their tax return.

Once I found my first job in high school and needed to file my own taxes, my dad showed me how to use the TurboTax software that he purchased each year, and for many years this is how I filed my own taxes. CD-ROMs turned into a turbotax.com, and the service fee seemed to increase a little each year.

Then came 2010: the tax year that I had two sole proprietorships, a contract employee, a home office, a transition into a new day job, and a significant amount of miscellaneous income. And all of a sudden TurboTax wasn't going to cut it. Actually, it's more that I didn't trust TurboTax to get everything done correctly. So I sought out a tax preparer. The fee was much higher, but the peace of mind knowing a human had done my taxes and made sense of my chaotic income was well worth it. I also owed a significant amount of money, and labeled my file Death By Taxes in reaction.

Do it [old school] Yourself

IRS 1040 Tax Form Being Filled Out by kenteegardin, on Flickr

Enter tax year 2011. A few months ago, I got a friendly reminder from my tax preparer that she was still available to file my return, but I didn't have my act together enough to turn everything over to her. My procrastination set in, knowing that I'd need to spend a couple hours recording all of my expenses. It's not just enough to save your receipts, people!

So last Saturday I sat down with last year's return, all of my expense files, my computer, and printed copies of form 1040, two Schedule Cs, and more. It was time to do my taxes—the old school way.

It couldn't be that hard, right? I had last year's professionally prepared return to refer to, all of my receipts to be categorized and added up, and a pen full of ink. It turns out, it really wasn't that hard at all. I spent a total of five hours on Saturday preparing my tax returns, and a good chunk of that was totaling up my expenses and categorizing them according to IRS standards.

procrastination by D'Arcy Norman, on Flickr

In fact, doing my taxes by hand was INVIGORATING. EXCITING. It bolstered my self-confidence. "I can do this!" I thought. "I AM doing this!" I got through the first round of number crunching, then went back through to double-check my math. (Did I mention that I can still do math, too?) Wait a second, what was I thinking? I forgot to re-add those numbers. I'm $1200 off on my business expenses!

Scribble. Rewrite. Recalculate. Scribble some more. Carry it all the way through from the Schedule C to the 1040. Whoa. My refund just jumped a hundred bucks. Triple-check. More errors (in my favor). Quadruple-check. Lookin' good! Now time for the state return. Copy the numbers over. Refund again! Yes! Double- and triple-check. Everything looks good. Walk away for an hour, clear my number-addled brain, then check them all one more time.

Print off the PDF, write out the envelope, attach the right forms, and send them off. I just did my taxes by hand for the first time in my life.

Tech Isn't Always Best

OldRacingBus by JayCMiller, on Flickr

I know what you're thinking. Either a) I'm crazy for thinking that was fun, b) you're jealous because you've never done your taxes by hand either, or c) you've just balled up in to the fetal position and are rocking back and forth because you still haven't filed your own tax return yet. Regardless, doing my taxes was absolutely liberating. I felt like I could accomplish anything after that five-hour session spread across the dining room table.

In reflecting on the experience later, I realized how much I learned in the tax-filing process. There are actual tax tables. You can't claim a home office credit of your business is operating at a loss. Employer retirement contribution credits fizzle out after a certain threshold of gross income. But, more importantly, "old school" is sometimes where it's at. There are more ways than one that technology either gets in our way or enables us to be lazy, stupid, or apathetic. Sometimes it's better to turn the clock back 30 years and do things by hand.

Now, I'm not advocating that we all dump our precious iPhones into the river and walk around barefoot. Nor am I implying that technology is all bad. I don't know where I'd be without the Internet, for example. But there are plenty of ways that we can actually consider doing things the old school way as a means of breaking ourselves out of our technological compulsion.

The Old School–Tech Balance

bringing it back by John Chevier™, on Flickr

When was the last time you talked on the phone to a distant relative? Do you use a physical recipe book, or are you constantly running back and forth from the kitchen to consult epicurious.com? Do you look at a map instead of consulting your GPS device, and could you get from one end of town to another without any navigational aids at your side? When was the last time you mailed invitations to a party instead of creating a Facebook event? When was the last time you walked instead of driving?

Some people insist on taking notes with pen and paper, not on a tablet or a smartphone. Others might simply handwrite letters, play an acoustic instrument, or press "0" to talk to a real live person. Sometimes technology complicates our lives instead of making it better, but we rarely notice it because we trust it too much to solve all of our problems. Sometimes our brains just need to work for something. Be put to the test and problem-solve. There's no app for that.

Take a moment, think about what it means to go "old school," and identify something that you do now that tech doesn't do better. How does it help you? Now, what one thing are you letting tech do for you that you could do the old school way? Try it. You might like it.

I'd love to hear your old school methods. Share in the comments below or tweet at me with the #oldschool hashtag.