Here’s How You Can Make Taxes Less Painful

Tax pain often manifests during tax season, in the form of stress, tension and anxiety. Entrepreneurs and freelancers may experience this pain many times throughout the year.

According to Jeff Brown at Psychology Today -

"...income tax season is the most dreaded time of the year for the average working adult. Headaches, heart palpitations, and anxiety plague many people as they worry about their tax returns. Looming fears of not knowing whether you’ve calculated your return correctly, the possibility of penalties, or frustration from simple math errors is enough to make some people obsess over filing. So they keep revising their tax forms over and over before they are satisfied with the result. This kind of obsessive behavior causes even more stress and anxiety and can lead to procrastination."

I wrote Tax Pain Relief to take some pain out of tax season.  Tax Pain Relief shows you how to make collecting your tax information easier and faster. You'll experience less stress, tension and anxiety if you spend less time on taxes . This results in an easier experience for you each tax season.

This relief is now available for free to subscribers of Just Rolling with It!

My Experience with Tax Season Pain

I'm an entrepreneur and freelancer.This makes tax time complicated and uncertain. The pain I used to experience at tax time compounded until it became almost unbearable.

I developed a strong aversion to tax time. This aversion caused me to procrastinate. Then I'd have to scramble at the last minute to collect my tax information.

My tax information was scattered all over the place. Papers were in various files and piles. Electronic documents were scattered across email inboxes and different websites. Piles of receipts were everywhere

I’d take deep breath and dive into the painful process of collecting the information. I would start with a checklist of what I thought I needed to collect. I'd realize the checklist was incomplete and abandon it.

Then I'd panic.

I'd start a panicked effort to pile all of the tax information that I thought I needed into one place. I'd mail and/or email the mess to my accountant and hope he could sort it out and tell me what was missing.

Stress, tension and anxiety were building the entire time. These difficult emotions built until I got the mess shipped out to my accountant. The stress, tension and anxiety lessened a bit after that.

This relief was only temporary. I then became afraid I might have forgotten a key piece of information. I was afraid my mistake could result in me overpaying my taxes.

The entire process took me at least 16 to 20 hours. The pain I experienced stretched out longer than that. It was also time I couldn’t spend on a million other things I’d rather be doing.

Feeling Tax Pain Relief

I began to think about how to improve this process. I came up with an initial system, then spent about 2–3 years refining it.

I'm now able to get the information over to my accountant in less than 30 minutes.

I realized this system, which I developed for my own use, works and works well by -

  • Reducing the time I interact with the entire tax information collection process
  • Freeing-up hours of my life to do things I'd rather be doing
  • Cutting short the time for stress, tension and anxiety to build
  • Preventing these painful emotions from building to an overwhelming crescendo

Sharing Tax Pain Relief

I decided to document the system and share it with others. I call the system Tax Pain Relief. Tax Pain Relief is available for free to subscribers of the Just Rolling with It newsletter.

Use the form in the sidebar to request your copy.

(The form is at the bottom of this post if you're on a mobile device.)

May it help make tax time less painful for you!

Disclaimer: This is not an offer of tax advice and I am not a tax professional. I just hope to ease your pain at tax time by showing you one way it is possible to collect the information someone else tells you that you need to collect to file your taxes!