5 Things I Wish I Knew About Freelancing

I have been freelancing for a long time.

Not in the flashy, six-figure, time to make a course way, but in the holy cats, my job doesn’t pay super well, and I’d like some side money way.

This isn’t just about teaching. In high school and college, I worked myriad part-time jobs for minimum wage. And I would still try to cobble together extra pay by babysitting (one child thought she heard voices in the heating ducts) and tutoring (100% less creepy than babysitting). It feels like I’ve been freelancing forever.

In fact, if we extrapolate, I likely will freelance forever (waves at bosses clients who don’t like the word boss who read this blog!). Freelancing is fun. It’s fulfilling, exciting, and different from teaching. Don’t get me wrong. I love my full-time gig and there’s a lot of crossover of skills, but sometimes it’s really nice to work for people who don’t try to turn their friends into a mummy with your Scotch tape during passing period.

While I am not an expert freelancer, I do realize that there are some things that I have learned that I haven’t yet shared here. Usually I just talk about how I’m side hustling not enough or too much or have decided that I hate the entire concept.

RELATED POST: The Stupidity of the Side Hustle

But I know some truths about freelancing. I know that freelancing is fun, and it’s powerful. Give me a second income stream over an emergency fund anyday. I also know that even though I still have plenty to learn, here’s five things that I’ve already realized along the way:

Pay Yo’ Taxes

In the spirit of full disclosure, I often wonder at what moment I’m going to have to write the blog post How I Narrowly Avoided Jail. Just call me Al Capone. (To be clear, I do pay taxes and always have. I just don’t pay them effectively on my behalf. Uncle Sam, I expect a thank you card next April.)

Taxes are complicated, and they’re even more complicated when you freelance. Because I don’t freelance full time and I set up my full-time career tax withholdings to be generous (I like big tax returns and I cannot lie! Sue me!), I haven’t had to file quarterly taxes yet. But it’s coming. I hope.

Basically, there are two methods to filing your taxes:

1. Do what you gotta do to support society, pay your dues, and stay out of jail. (It me!)
2. Optimize with write offs and deductions. (Most definitely not me, says the person who recycled all of her FinCon receipts from last year. Whoops.)

This winter, I’m actually going to work with a tax attorney to get my act together once and for all. I know I could DIY it, but I’m willing to pay (once) to optimize and then just copy-cat until I get stuck again. I promise to keep you posted once I have unlocked all the secrets to optimizing my side hustle business and am most certainly not writing from jail.

Don’t Take It Personally

I get this advice all the time. I make a face and internally rage at the person who gave it. In the spirit of being helpful, here’s the face you should be making at me:

via GIPHY

When you work hard and give your all, it’s hard to not take feedback personally. I don’t care if it’s a traditional W-2 job, freelancing, or the barter method. But you have to try to distance yourself from the feedback. It’s the only way your work will get better.

Know When to Walk Away

If you want to freelance effectively, you have to separate yourself from your work at times. We know, Penny. You already covered this.

Hold your horses, partner. It’s worth repeating, I promise.

This concept of separating yourself from your work is especially important to remember if you ever come across a client that isn’t the right fit. This is not a romantic relationship. This is not a marriage. There was no exchange of vows, nor did your Aunt Cathy and Uncle Mike send you a personalized gravy boat. Not every gig is a good fit. Sometimes you have to walk away. And that’s OK. It’s hard, but it’s OK.

RELATED POST: Why I Quit My Highest Paying Side Hustle

Know Your Worth

You don’t need to work for free. Could you? Sure. Will lots of people ask you to? Of course. But should you? Absolutely not.  If you’re looking to freelance to replace a full-time income, let’s just say that $0 doesn’t replace anything. That, my friends, is called volunteering.

Even if you only freelance on the side like moi, your time is still valuable. You could be doing lots of other things. Catching up with family, visiting friends, exploring the outdoors, grocery shopping, meal planning, dusting, decluttering, napping. The options are virtually limitless but your time is not. Time is a non-renewable resource. Treat it as such.

Related Post: No, I Don’t Want Your $15 Writing Job

Be Priceless

If you think there’s a lot of competition in freelancing, this is not the part of the story where I pat your head and tell you that you’re wrong. You’re absolutely right. The competition is fierce, and it’s growing every day. Especially thanks to platforms that have people knocking down doors to work for $5 an hour. 

Of all the things that I’ve learned about freelancing, this is hands down the most important one. Once you land a gig that you love, make yourself priceless. Do the work. Do the work in a way that you’re proud of what you’ve accomplished. Give it 100%. That’s the best way to keep your current work and a surefire way to find more.

Ready to Freelance?

There are endless resources online to help you get started freelancing. One quick Google search of the word “freelancing” landed me 328,000,000 results in 0.6 seconds. Who has time to go through all that?

Nobody. Nobody has time for that.

Kara from Bravely put together an awesome freelancing bundle to help take some a lot of the guesswork out of the freelancing puzzle. Honestly, you could spend dozens of hours combing through the Internet only to find conflicting information. If you want to see freelancing distilled down into a neat workbook and two fun videos, check out the Bravely Freelance Starter Guide. (Not an affiliate link; just sharing a resource created by a pal!) The guide touches on everything from taxes (guess which chapter I need to revisit obsessively?) to setting wages to get yourself paid fairly (she breaks it down with actual numbers!).

You can also always visit my blog where I will continue to regale you with tales of my side hustling. I can’t promise that my stories will always add value, but hopefully they’ll make you laugh…or cringe. Plus, some really smart people do chime in down in the comments section.

Final Thoughts on Freelancing

Freelancing can feel like one giant cliche. The Wild Wild West. The vast unknown. It’s a path that no two people chart the same way. There will be starts and there will be stops. Still, there are plenty of resources and people you can learn from as you go.  

So Tell Me…Do you freelance? Why or why not?