My first career was with the United States Army. My first experience with tax preparation was with the Volunteer Income Tax Assistance (VITA) program when I was a Second Lieutenant stationed with the 8th Infantry Division in Germany. Believe it or not, I enjoyed the process of preparing income tax returns! Nineteen years later as my time in the Army was winding down I decided to pursue the certified public accounting profession. I'm now a licensed CPA in Kentucky and Virginia and enjoy tax preparation as much now as I did back in my Lieutenant days in Germany.
I learned a great deal when I was in the military but one lesson resonates in the world of income tax and that is to have a plan. It is always better to have a plan - always. Very rarely in my Army days did I ever experience a plan that survived to the end without being modified in some manner. It's the same with income tax filing. If you establish a plan and follow it closely you'll know when it gets thrown off course and you'll know what to do to get it back on the rails.
Filing an income tax return need not be as painful as you may have experienced. A proper plan, methodically executed, greatly reduces the angst and pain at tax filing time. Compare filing an income tax return each year to a trip to the dentist office. If you've followed the recommendations to brush and floss regularly your visit will likely go very smoothly but the less you follow the dentist's plan the greater your discomfort the next time you find yourself in the dreaded dentist chair.
If you find that you can't enjoy March Madness because you owe a pile of taxes or you haven't filed your return when the championship team is crowned you need to find someone that can help you plan for next year. I'll happily help but if you don't call me, call someone. Your friends and family will thank you.