My first quarterly tax bill

Panic, fear, etc.

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When I first became a freelance writer in 2014, I thought of it as an experiment. I had just been laid off at an awful, very short lived job for Ken Freidman and April Bloomfield (I wrote a little about the experience here, if you’re interested.) I had always done some freelance writing as a side hustle, so I had a few clients and a few projects going. I told myself I’d give it six months, and then reevaluate.

What if I could actually make a living doing the thing I loved to do?!

A few months in, I was feeling pretty confident. I was working hard, but also taking breaks for a spin class or a walk or a coffee with a friend in the middle of the day because I had brand new freedom, and I was embracing it. I planned a six-week long trip with my bestie to visit her in Berlin and then travel to Istanbul JUST BECAUSE I COULD. I got new assignments and made myself a spreadsheet for all my invoices and to keep track of money.

And then!

I had a chat with a friend’s finance person, just to make sure I had my ducks in a row. And they told me about a little thing called estimated quarterly taxes.

(If you expect to owe more than $1,000 in federal taxes for the tax year and you are self-employed, you probably need to make estimated quarterly tax payments. That was me; that is me.)

I logged into TurboTax.

My heart sank.

Here I was, feeling all self sufficient and organized and competent. And then suddenly, I owed a few thousand dollars I wasn’t planning on, and I owed it stat.

I remember the bubble of panic that rose from my belly and into my chest. It felt like such an injustice! I was so carefully planning and yet I had missed such a big thing. I had a little, very hard-earned cushion in my bank account that was going to disappear in the blink of an eye. Rent was due, too.

It was a bad day, but it ended up working out ok. I scraped the money together. I got a pep talk from a more experienced freelance writer friend. And I joined QuickBooks Self-Employed, which I highly recommend, to plan for these payments going forward. (They have a great app, too.)

I’ve had a few full time jobs since then, but I’ve mostly worked as a freelancer. Writing has always been at the heart of my work, but I also edit and.teach, coach and strategize, copywrite and copyedit.

I absolutely have enormous privilege. I also supported myself for many years in the most expensive city in the world (one of ‘em, anyway, love you forever NYC). Every year, I’ve done a little better than the year before. I’ve learned a lot of lessons along the way.

Quarterly taxes are due June 15 and I’m not even nervous.

One of my writer heroes Hannah Selinger and I are teaming up to teach a class about MONEY. We’re going to dive into all the things we wish we knew when we started. I’m so excited to share what I’ve learned.

There are still some spots left, and we hope you join us!

xo,

Hannah

PS I heard this and I’m sharing it because I love it! Don’t feel (too) bad about paying a lot of taxes, because it means you’re making a lot of money. Cha-ching.

PPS Here is baby freelance writer me, working from the roof of my hostel in Istanbul. Oh, the life!