Paying Taxes & Dental Bills as a Freelancer

how you can avoid making the same mistakes I did

When I was in my twenties, there were a couple of things that I thought were bullshit:

  1. Learning that I had to get my wisdom teeth pulled
  2. Paying taxes

First, the wisdom teeth:

Multiple times over the span of 10 years, dentists told me that I should have surgery to get my wisdom teeth removed. Even though I felt no pain or any indication of them causing a problem, the x-rays apparently told them otherwise.

I thought it was all a hoax: a money making scheme and an excuse for them to do surgery. Aren’t teeth a natural process that we shouldn’t interfere with? Plus, I didn’t have dental insurance and didn’t have the funds to easily fork over hundreds and hundreds of dollars.

So I didn’t get them taken out.

I turned 30 and at that point the teeth were growing in, but still not really causing a problem. Until December of 2013 when I started to feel an excruciating pain in that area.

And guess what the timing was?

ONE WEEK BEFORE my TEDx Talk.

What the dentists’ predicted happened: the teeth grew in funny and caused an infection. I was in serious pain, could barely eat or talk, and I was scheduled to give a career-defining speech just days later.

The magic of coconut oil pulls did wonders (google it if you’ve never heard of that) and I was able to deliver my talk pain-free. The following week I sucked it up and got those babies pulled.

this is me, post wisdom teeth surgery

(p.s. The laughing gas was well worth it, and I listened to a Janis Joplin album throughout the whole process because my oral surgeon was really cool. Epic.)

Another phenomenon happened with my taxes -

When I quit my 9–5 job with benefits and health insurance at age 23, I felt a rush of freedom and purpose because I was finally living the life I truly wanted! I became an “independent contractor” and made money via health coaching and other side jobs I found at the time. When my first tax season rolled around I was appalled that I had to fork over money to the government — my hard earned income!! There was no longer an automatic system that set aside that money every 2 weeks and paid it for me. Bummer.

I had to borrow money those first few years to actually pay the taxes, and later I went on to payment plans with the IRS to be able to pay the taxes back.

Being totally transparent with you, I’m probably still going to be back-paying my taxes from last year, but I have made leaps and bounds in getting support with my finances and am getting more and more organized every month. And I’m committing to paying taxes in advance this year!

(If you’re an independent contractor/freelancer/entrepreneur too and haven’t been paying your taxes in the current year, you can enroll here and pay them quarterly, electronically.)

It feels so great to know exactly what’s coming in and out of my bank account, and to have strategies in place to keep it flowing smoothly. It’s starting to feel better to pay taxes. I won’t lie and say it’s all a party, but I am starting to appreciate the fact that the more money I pay in taxes, the more value I’ve provided to the world that year.

So, I wanted to point out a few things that I learned so that maybe you can avoid some of my same mistakes:

1 — What you don’t address in the moment is going to bite you in the ass later.

Putting things off for “later” usually turns into an urgent situation that needs attention, whether it’s money, health, emotions or otherwise. Much better to handle it before it gets too extreme.

2 — Money comes and goes.

Forking over hundreds or thousands of dollars for an investment in your health, career, or personal life, can be a healing process. The thousand+ dollars I spent on my teeth was painful in more ways than one, as were paying my taxes, but in the end it helped me. I let go of need to hold onto things and trusted that the empty space — in my gums and my bank account — would be filled up again.

3 — You have the power. You are not a victim.

One of the biggest things I’ve been learning is this. It’s so easy to be a victim to the big bad government, to the medical system, to life circumstances. When you stay in victim mode, you draw in more catastrophes and feel helpless. It doesn’t help anyone. When you take your power back and look at every situation as an opportunity for growth and new ideas, it empowers you to take steps you never thought were possible.

As we near April 15th…

I hope that you embrace your taxes and other bills with power and purpose. Let’s continue creating and adding value to the world, all while dancing to the rhythm inside us.


This article was originally published by Jess Grippo on Creative Fridays, the weekly nudge for your creative spirit. To get these inspiring notes delivered directly from Jess to you each week, sign up here.

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