5 Things I Wish I’d Known About Freelancing Before I Started

I started freelancing full-time in 2009. When I did, I was unemployed, bedridden with multiple disabilities, and typing on a five-year-old laptop in my parents’ basement.

That is not how I recommend anyone else get their start.

Now, nearly ten years in, there are some things I wish someone had told me when I started – things I didn’t get from all the “how you can has freelancing too!” blogs or the books on how to write. And here they are.

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1. Job posting quality is directly proportional to client quality.

You may be tempted, at first, to reply to every job posting you can find. You may be especially tempted to respond to the pathetic one-liners from late-night college students: I need some1 to rite my final xam email me plz.

Don’t. The clients you’ll actually want to work with are the ones who write organized, cogent job postings in standard English that summarize the job, its requirements, and its pay.

Why? Because those are the clients who have their business together enough to know (a) what they’re looking for, (b) how to explain what they’re looking for, (c) how to provide useful feedback (if any), and (d) how to pay you on time.

Speaking of your pay….

2. Sometimes you will have to shake clients down.

Life happens. Your contact at a client’s business leaves, their payment processing system collapses, their project management software eats your hours, you think you turned in your hours but turns out you’re remembering last month and not this month. Whoops!

When the problem isn’t on your end, you’ll have to get persistent. Re-send your invoice with a brief note: “Here’s a copy of last month’s invoice, which I sent ten days ago. Let me know when I can expect payment. Thanks!” If they skive off altogether or still don’t pay, a phone call may be in order. And never, never accept more work from a client if they have an outstanding bill.

(Tip 2.5: Make sure you’re getting paid slightly more than your usual rate if the client demands you learn a project management system of any kind. At one point, I had to navigate four different systems just to get paid. Not worth it.)

3. (Certain) lies are okay – even necessary.

“Samples” are the “experience” of the freelance world. You can’t get samples without working, and you can’t get work without samples.

But if you’re just getting started – in copywriting, say – you may not have relevant samples. This is especially true if you’re attempting to work as a freelance writer during or just out of college (not recommended).

The good news? It’s okay to fake your first samples. Write a press release for a fictional company. Write a blog post covering a how-to you already know how to do, like “How to Start a Student Organization That Gets Things Done” or “How to Do Your Laundry In Half the Time.” Ask a friend if they’ll let you guest post on their blog or write some web copy for their site.

Tip 3.5: DO NOT WRITE ON SPEC. “On spec” ostensibly means “you write this and if it’s good enough, we pay you.”  Increasingly, however, “on spec” is code for “we’re going to tell you this isn’t good enough and not pay you but we’re going to use it anyway.” Assume anyone asking for “on spec” work is asking you for free work, and skip them.

4. Don’t quit your day job.

If your day job has already quit you, you’re probably frustrated just hearing this. So let me say: don’t quit your day job if you can avoid it.And if you can get another day job while you boot up your freelance writing business, do it.

I started freelancing with no day job, and it sucked. The stress was incredible. People make bad decisions when they’re stressed, and I was no exception.

Because of the stress, I did some really stupid things in my first few years as a freelancer. I took work from clients who never paid me. I groveled to clients whom I should have quit outright.

Freelance relationships are a lot like other relationships: Clients are more likely to respect you if you respect yourself. Set boundaries around the time and types of work you take. Enforce them.

A Special Note for college students: Don’t plan on freelancing as your “job” when you finish your degree if you have no other type of career experience. Most places looking to hire freelance writers want someone who has actually worked in the field or industry about which they want you to write. Get a few years’ experience doing literally anything, then build your career on that.

5. Treat 50 percent of your income like it doesn’t exist.

I mean it. Set up a savings account. Name it “The Black Hole” or “Where That Half Of My Freelance Income Goes When It Does Not Exist” or even “Steve.”

Honestly, it doesn’t matter what you name it. What does matter is that you put $0.50 of every dollar you make in this business into that account. Put it in right away, the moment you get paid. If you get paid via PayPal, set up an automatic transfer that moves half of it into that account the moment it clears PayPal.

Why 50 percent?

Thirty percent, approximately, goes to pay your taxes. Taxes are the number-one thing that shock every new freelancer, and for good reason: Self-employment taxes are higher than taxes for conventional employment. Between self-employment tax and income tax, you’ll be paying a higher percentage on your income to the IRS than you ever have before. (Now is a really good time to learn what you can and can’t write off as a business expense when you’re a writer.)

The other twenty percent is your retirement fund. Remember, no one else is paying this for you: there’s no pension with this job, no 401(k). Once per year – ideally, right after you pay your taxes – take this other 20 percent and put it in an investment vehicle. A CD. A money market account. An IRA. It literally doesn’t matter, as long as you keep it where you cannot spend it.

If you’re like a lot of freelancers, right now you’re probably saying “but I can’t afford that! I need all that money so I can eat!”

….This is the other reason I highly recommend not quitting your day job. Do whatever you can to avoid relying solely on freelancing until you can live on 50 percent or less of your gross freelance income.

Your future self will thank you.


Freelancing is great once you know what you’re doing. Share this post, support my work, and help other freelancers learn from my mistakes.

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