I’ve never been taught how to do taxes. I’ve pieced it together from my parents, the Internet, and as of last year, my incredible financial planner Shannon Lee Simmons.

My taxes are complex and it completely overwhelms me. I have a full-time job, and had seven different income streams last year (motivational speaking/event hosting/TV producing/producing web content for an entrepreneur/I’m an affiliate for Tilt and Instapage).

Yes, it’s exciting to find creative ways to get paid, but goddamn it, it’s stressful as f*ck to figure out how to pay the government for your passions. Although I promised myself this wouldn’t happen AGAIN this year…I’ve again waited until the last-minute to take a look at everything.

Here’s my TERRIBLE strategy this year, as well as my new strategy I’m implementing now so next year won’t be such a shit show.

Gwen’s Tips for a Terrible Tax Strategy:

  • Try to do it all at once.

I have been sitting in the same spot for five hours, going through an insane amount of paperwork, highlighting and circling numbers. My brain hates me. This is NOT the optimal way to do this. (I thank Nicki Minaj and Drake jams for keeping me company through this challenging time).

  • Avoid looking at docs until the last-minute.

I’m missing an important document that I now have a minimal window to track down. This could’ve been easily avoided had I taken a gander at all of this tax stuff much earlier.

  • Avoiding in general.

I’ve suddenly found myself eating, drinking, and sleeping to numb out and avoid. It’s dumb, but it happened. As Tony Robbins would say: the pain of avoiding was greater than the feeling I’d get of accomplishing all of the tax stuffs.

  • Don’t keep documents organized in any way.

I envy those who are magnificently organized. I have receipts in a box, and random papers in a drawer. It’s kind of all there, but there’s no great organization strategy. Disorganization is a HUGE deterrent to gettin’ er done.

Gwen’s 100% improved Tax Strategy:

  • Have a monthly money date.

Instead of trying to tackle every expense and income stream all at once, I’ve scheduled a one hour money date on the last Friday of every month. I’ve created a simple excel doc where I can enter business expenses and income.

  • Organization: DO IT!

Organization must exist! This time around, I’m going to use the file folder system that’s been sitting around collecting dust. Instead of putting receipts in a drawer, I’m going to actually start filing them. This will be a serious game-changer.

  • Book my tax session in January.

I’m lucky that my gal Shannon is willing to fit me in, but this year I’ve GOT TO book early. I’ve actually put a note in my Google Cal to book next January 26th, 2016!

If you’re in a position right now where you have no idea where to start, my #1 piece of advice is DO NOT DO THIS ALONE! Research a financial planner in your area and reach out and take action. Yes, it may cost a pretty penny for the advice, but think of the mental energy you’ll free up!! You can do this. Start small, take action, and know that you’re not alone.

<3 Gwen



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