5 Freelancing Lessons I Learned the Hard Way: Avoid These Career-Killers

Carol Tice

Freelance writer gets in troubleBy Erika Dreifus

Several years back, I was freelancing full-time. Or trying to.

With hindsight, I’ve realized I made several mistakes.

Some of them doubtless contributed to my return to full-time staff employment.

If I ever again attempt full-time freelancing, I’ll keep these lessons in mind:

1. Get it in writing

I know this. You know this. We all know this. And yet, sometimes the mere promise of a byline and a paycheck can make us so happy that we don’t insist on a contract, or at least, an email spelling out the specifics. Including that all-important kill fee.

Without those written assurances, we run the risk of doing the job without ever laying eyes on the byline OR the paycheck. Plus, there’s the lost opportunity cost: It may be too late to scramble and place the idea elsewhere.

2. Read the fine print—even with a repeat client

After writing print articles for one client many times, I got lazy. I stopped reading what seemed to be a “boilerplate” contract.

Thus, I failed to notice when the contract evolved from promising a certain extra percentage of my fee for material also chosen to appear online, to promising a smaller percentage, to stating that online rights were part of the deal.

Naturally, that’s when I started noticing more of my work appearing online, making it much harder to resell elsewhere. Definitely my bad.

3. Make negotiable demands

Several years ago, I pitched an idea to a major magazine. I’m not sure what possessed me, in the negotiations that ensued, to state brazenly the fee I wanted.

When asked what I was hoping for, I should instead have followed the smart advice I’ve since heard from a number of expert freelancers: “Answer with a question: ‘What’s the most you can manage?’”

That way, I might have sustained the negotiations, rather than giving the editor a reason to end them.

4. Run from the crazies

Ninety-nine percent of the people you’ll deal with in your writing career will behave in a perfectly rational and respectful manner (as you do, of course!).

But every so often, you may encounter someone—an agent, an editor, a fellow writer—who may be rude, threatening or simply incomprehensible in their correspondence or conversation.

LET THEM GO. You don’t need to have the last word (it may not be possible with some of these folks anyway). Move on.

5. Put your freelancing eggs in multiple baskets

I can’t help suspecting that my foray into full-time freelancing would have yielded better results, not to mention cash flow, if I’d diversified my income streams.

For instance, instead of focusing so intently on freelancing for magazines and newspapers, I should have acquired copywriting skills and experience.

I should have attempted to engage corporate clients. I should have investigated ghostwriting.

What freelance lessons have you learned? Leave a comment and share yours.

Erika Dreifus currently freelances on the margins of a full-time staff job. She blogs about writing and publishing (especially for poets, fictionists and writers of creative nonfiction) at Practicing Writing. Follow her on Twitter @ErikaDreifus.


  1. Lisa Romeo

    Number 4 may be the most important – for freelancing or anything. Walking away has lost me money sometimes, but always saved my sanity, and often left me with time enough on my hands to figure out how to make something better happen.

    • Erika D.

      Kind of amazing how powerful #4 is, isn’t it? Thank you, Lisa.

  2. Sue LaPointe

    My favorite is your #5… Walking around with all your eggs in one basket is a pretty sure way to guarantee you trip over a rock, skin your knee as you fall, then end up in a puddle of goo.

    Expanding into bigger, better, badder (in a good way!) clients took some confidence-building on my part (yeah, Peter Bowerman was right… as usual), but will make it much easier and faster to make my nut and more.

    • Erika D.

      What perfect imagery in that first paragraph, Sue. Thanks!

  3. Eleanor

    Great article. I think one of my lessons is ‘never say never’. Sometimes as a writer you have to explore other avenues, even if they scare you initially. Most of the things I have ever done are things I have said I would never do, and it is always worthwhile in experience if nothing else.

    • Erika Dreifus

      “Never say never.” That’s a good one!

  4. Amandah

    My biggest lesson is around contract. Make sure deadline dates are nailed down before you write. I didn’t do this with a screenwriting gig, and I got burned. It was my fault. I read the contract and re-read it, but the ‘light bulb’ didn’t go on in my brain. It was very clear to me that the project would become the ‘never ending’ screenwriting project. Lesson learned.

    • Erika D.

      There are definitely plenty of contract-related lessons to be learned. Agreed.

  5. Kevin Carlton

    For me, one of the biggest freelance mistakes you can make is to believe the prospective client who says “If you do this for lower price then there’ll be more work in the pipeline”.

    • Carol Tice

      Har…yeah, that makes me want to do a post like “The Biggest Lies of Clients” or something.

      • Erika D.

        That sounds very promising, Carol! 😉

      • Kevin Carlton

        I’m already looking forward to the post you have in mind.
        There is another one that clients try on, which I find equally insulting, although it isn’t a lie as such. This is where the prospect wants to pay you next to nothing and justifies it by saying ‘But this will be really good experience for you’.

        • Carol Tice

          And awesome exposure! Thanks, but writers die of that.

  6. Linda H

    I like the entire list. Number 3 reminds me of a scenario I remember like it was yesterday–it was over 10 years ago–I had a client negotiating price for a typing project he wanted done. I gave him my price and knew it was very fair. He said — “I can get it done for XXXXX down the street.” I handed the papers back to him and said, “Okay, I hope it works out for you.” He sat there amazed. I wouldn’t negotiate down because I knew I was better and could do it right. I wouldn’t work for peanuts back then either. After realizing he wasn’t going to get a price break he hired me anyway. He said it was the best writing job he’d ever seen. I negotiate pricing now, but still struggle with how much. I’m getting better at it though.

    I love #5. I’ve always been one to have many eggs in many baskets. Guess it comes from being fascinated by the movies and smitten with movie stars as a kid. I read alot about many and remember Richard Widmark’s comment about making a movie should be something you do on the side, not something you have to do to survive. Many movie stars did more than make movies, so I learned by age 10–always have your eggs in more than one basket.

    The entire list is fabulous. So many stories run through my head. The best thing though is run from the crazies. They’ll suck the life outta ya and leave you hanging, then refer others to you who expect the same price or the same deal. Never worth the headaches!

    • Carol Tice

      No kidding. My husband has like a fatal attraction to crazy clients in his videography business, and I’m always trying to cure him of it! Such a time-waster and earnings-cutter.

    • Erika D.

      Great story in that first paragraph, Linda. Thank you for sharing it.

  7. Joan Lambert Bailey

    Im sorry to say that I know these errors all too well. Things are going ok now, but my experience has been similar. There’s some comfort there. Any suggestions for turning these situations around? (Except for the irrational people, of course.)

    • Erika D.

      Hi, Joan. Well, I’m not sure what you mean by turning them around. The idea is to steer clear of the mistakes (or follow some of the suggestions mentioned in the article) in the first place.

      I’m sorry that the errors resonate so strongly! Thanks for commenting.

  8. Terri H

    My hard lesson goes back to contracts. I learned the hard way that it’s just as important to spell out the deadline of client deadlines as well as mine.

    About a year ago I had a situation in which I wrote a blog post that had several deadlines – one for the first draft, second draft, one for the final copy, etc. I turned in the first draft and requested the client to look over for it changes, corrections, etc so I could edit accordingly. The client didn’t give back their critique until the date that the final copy was due and still expected to receive the final hard copy on that day despite hounding them for the feedback for weeks. I still got the work done for them but it put me in a bind because I had other pressing projects lined up.

    Now, I am sure to spell out what date I will turn in things and a specific date they must get back to me. I also make sure they understand that successful project completion is dependent on my self and the clients ability to cooperate and be available to answer questions in a timely manner, etc.

    • Erika D.

      Great points, Terri. Thank you.

  9. Andrea

    I am now also thinking of making freelancing a full time living but isn’t it dangerous to rely solely on freelancing? I guess you can earn more but there are no benefits. What are the pros and cons of freelancing?


    • Erika D.

      Well, Andrea, I think we’d all agree that there are risks inherent in freelancing, and it’s not something for everybody. Hopefully, my post points to some ways to reduce those risks (for example, #5, diversifying your income streams). And some benefits–such as health insurance–can be obtained through professional writers’ groups. But yes, a benefits package is definitely one of the attractions of my current full-time staff job. At the moment, as the bio notes, I’m simply freelancing on the sidelines. There are pros and cons to almost everything in life, and freelancing is no exception. You’ve already identified some of the cons. I’d say that one big pro is the flexibility of the work schedule.

      • Carol Tice

        I personally feel at this point, there is more risk to having one job, where you can be fired and lose everything overnight, than there is in freelancing, where you have a variety of clients.

        • Erika Dreifus

          Fair point, Carol.

      • Vinil Ramdev

        well Erika, it depends on how you look at it, there are risks in everything.. i read somewhere – “security comes from competence.” I know some people who became self-employed and are making much lesser now, but that’s because they haven’t yet built important skills like sales and marketing to get ahead. I guess the answer differs from person to person, one strategy doesn’t fit all.

  10. Sarah L. Webb

    I just started freelancing full time four months ago, and I need to improve in almost ALL of these areas.

    I think it comes down to guts, having the courage to get a contract BEFORE I do ANY work. Because I’m new, as you said, I sometimes feel I have to compromise. I know I shouldn’t feel that way. I’ll have to compromise in other ways, but not on a contract.

    Contracts and proper negotiation also make you appear MORE professional, which is exactly what new writers need.

    Thanks for the practical advice.

    • Erika Dreifus

      What you say about appearing MORE professional by engaging in contracts/negotiations is so true, Sarah. (At least, I sure think so.) Good luck in your new freelance life!

  11. Clara Mathews

    This is such good advice. If only we all knew these things before we started freelancing. It would have saved so many headaches with crazy clients.

    • Erika Dreifus

      Exactly! I hope the post will help others avoid making the same mistakes.

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  13. Karen J

    Cordelia’s Link Love here caught my eye – I’m glad I came!
    I’ve never thought of myself as a Writer per se, more of a Freelance Generalist, but these points are valid for any almost sort of project. 🙂

    I’d add a #6: Know your Resentment Rate – and stay away from it!
    Shanna Mann wrote about it this summer: http://shannamann.com/blog/defining-your-resentment-rate
    It’s easy to fall into “I’ll do anything for money right now” when your plans (or wishes, if you didn’t really “plan”) aren’t working out like you thought they would. And, it never-ever helps for very long, because you’re very likely to get trapped by Crazies (see # 4) – they’re attracted like sharks to the desperation.

    Subscribing momentarily, Carol.
    Bright Blessings ~ Karen

    • Erika D.

      Thanks, Karen. That Resentment Rate is definitely something else worth keeping in mind.


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