What I Wish I Knew About Taxes for Freelancers When I Started

I write about money for a living. You would think that fact alone would protect me against some, if not all, the surprises that come with paying taxes. But alas, the transition from salaried employee to employee with a side hustle and then to a full-time self-employed person came with a few stumbles.

Some were self-imposed. Some were lack of knowledge about the tax system. And some were based on down right bad advice. The truth is – taxes for independent contractors are never an easy thing to master when you’re first starting out.

To help you avoid some of the mistakes I made, here are the top five things I wish I’d known about paying taxes when I first started freelancing.

1. Not everyone will send you a 1099-MISC

When you work as a freelancer, the simple days of getting a single W-2 and filing taxes with one form are gone.

At the time I entered the freelance work market, I knew to expect to receive a lot of 1099-MISC forms from my clients. I understood each of those forms reported the amount of income I earned from each specific payer.

What I didn’t know is that your client isn’t required to send a 1099-MISC if you earned less than $600. And there certainly were times I earned less than $600 from a single client. However, when you’re freelancing, you still have to report the income when filing your taxes even without receiving any 1099 form.

I remember spending my first year waiting for all my 1099-MISC forms to arrive thinking I needed them before I could file my taxes. As I approached the filing deadline, I then realized some would never arrive. Luckily, I’d done a good job of tracking all my income, so I could accurately report it on my tax return without all the forms.

2. Save for city tax too

Common advice for those freelancing is to set aside 30 percent of each paycheck for taxes. In general, this advice is focused on paying federal (including Social Security and Medicare), state and self-employment tax.

But, unfortunately, that wasn’t all I had to pay. I live in New York City, so I not only pay a high state tax, but I also get hit with city tax bills. For that reason, I bumped my savings up to 40 percent of each paycheck to account for additional taxes. Any money I had left over beyond an emergency fund was put into a SEP-IRA for retirement.

3. Put money into a SEP-IRA

My career started in the traditional workforce where I had access to a 401(k). I contributed diligently to that account out of each paycheck. Additionally, I doubled-down my retirement savings efforts by putting money into a Roth IRA.

I started freelancing while working a full-time job, so my retirement savings strategy didn’t change in the first year. However, I quickly realized how much better a SEP-IRA was for my freelance income. And that became even clearer when I jumped to working for myself full-time.

SEP-IRAs have significantly higher contribution limits compared to the $5,500 allowed for a Roth IRA. I could put away the lesser of 25 percent of my compensation or $54,000 (TY 2017).

Right now, I’m not balling on over $200,000 a year (yet). However, 25 percent of my compensation is still a lot more than $5,500.

4. Paying a tax penalty doesn’t need to happen

The first year I needed to pay quarterly estimated taxes, I decided to ignore it until I filed my annual return for my full-time job. However, I always saved some of my freelance income to account for those taxes plus the anticipated penalty for not paying quarterly.

That’s right, I knew I’d have to pay a penalty and I still ignored filing quarterly estimated taxes.

This strategy was partly due to another self-employed friend telling me she found the whole thing a hassle. She said paying the penalty was much less painful than the time spent figuring out how much she owed quarterly. I went with that mentality and used the excuse of, “my time is worth more and I’ll just pay the penalty.”

Fortunately for me, the penalty wasn’t too painful. But that’s only because I was still paying taxes at my full-time job at the time.  But, in reality, that’s not the smartest excuse to use. Looking back now, my tax advice is to take the time to calculate your income and expenses as well as tax deductions and pay your taxes quarterly if you anticipate owing more than $1,000. That way you avoid a large tax bill next tax season and having to scramble to pay it.

5. Making estimated tax payments when freelancing is simple

Plus, it keeps me accountable throughout the year to monitor for deductions and track my expenses. Tools such as self-employment tax calculators make it even easier. I can’t imagine how big of a headache that would be if I waited until the end of the year.

So, the ultimate thing I wish I’d known about taxes when I started to freelance was just how simple it really is to pay quarterly estimated taxes.

Photo credit: Erin Lowry