Four years of freelancing: 20 things I learned the hard way

I’m celebrating my fourth freelancing anniversary today (hence the cupcakes), and after much reflection, I’ve compiled a series of tips–things I wish I knew ahead of time. Grab a drink and celebrate with me by taking some of these to heart, and feel free to leave your own tips in the comments.

Quality of life

Use good tools.

I got a smartphone my first year of freelancing because I realized that I was afraid to leave my house (due to lost assignments; editors would email me at the last minute and I couldn’t respond quickly enough). I also got my trusty MacBook Pro because my Dell, which had never worked properly, now had the added bonus of having keys from the keyboard falling off. (Shades of Gadsby.) My second year of freelancing, I started using Freshbooks for easy invoicing, and a recorder app for phone interviews. At the end of my third year, I started coworking, which has helped me a lot with networking and camaraderie. This year I’ve been madly in love with Trello (project management), Do it [tommorow] (daily to-dos), Draft (for collaborating) and Scrivener (for organizing long articles with multiple interviews and resources). Many of these resources are free or cheap; others are far worth the cost.

Take time off.

When you first start a business, you are glued to your computer screen 24/7. That’s okay. As your business becomes more solid, you’ll have to slowly wean yourself off this schedule. It’s okay to go out for dinner, go to the gym, go on vacation or have non-working hours in your day… or even to turn your phone off. Really.

Worst-case scenarios happen. It gets better.

Whether you completely lost audio footage from a once-in-a-lifetime interview (thanks, Retronyms) or got screwed over by an unethical website or publisher, chances are good that your career isn’t over and your reputation is salvageable. Explaining your situation (publicly or privately, as warranted) and eventually moving on is almost always possible. It’s okay to take a day or even a week off to recover, though. So much of freelancing is about your energy and mindset.

Learn journalistic principles.

If you didn’t go to J-School, at least read and understand the SPJ Code of Ethics. Know the difference between custom content and editorial writing, and learn about conflicts of interest. You may not follow all the “rules” of journalism, but you should at least know what they are and make informed decisions. Join professional groups, attend trainings, and soak up as much as you can from the people around you. Always keep improving your writing. A lot of this will happen on the job, but some will take your own initiative, research and even courses. Keep at it–you can always improve.

Go to conferences and take courses (but not all of them).

Some conferences will yield a high ROI (particularly ones with editor meetings);  others will be all but a waste of time. Similarly, some online courses will help you hone a skill you really need to develop–and others are marketing hype. Some trial and error is expected, but getting out of your home office is usually  more than worth it. Try travel hacking and AirBnB or HotelTonight (or stay with friends) to save some cash. Make sure to network and enjoy meeting other writers as well as attending informative sessions.

Let’s talk about money.

It’s not always worth it to write about things you know nothing about.

In my first year of freelancing, I wrote an article about bees for a trade journal. Yes, I made some money, but it took forever since I had to learn some material from scratch. Once I created templates to analyze data from complex financial documents that I didn’t understand. I pulled it off, but it took a very long time. I seem to relearn this lesson every year, whether I’m trying to learn a new style guide overnight or just accepting work against my better judgement. It’s always obvious to me when even the best editors of mine don’t understand the subject matter (and they usually don’t last long in that position); although expanding one’s horizons is a good thing, if you’re doing specialized work, it pays to be specialized.

Set a minimum-both for pay and for expectations.

It always seems that clients asking for work on the cheap are also the first to demand add-ons not normally included in low prices. It’s up to freelancers to explain to them what is and is not included. Remember: pay per hour is a thing. Someone who pays well but insists on long phone conversations, etc. may pay less per hour than that low-paying blog post where you don’t have to find images or do a lot of research, but when the person at the low-paying gig suddenly asks for you to find and crop photos, spend 15 minutes on their new SEO software, do extensive research or rewrites/revisions or learn a CMS, you can decide whether or not you think it’s worth it.  Setting a minimum is an option (and it can be a different minimum for leaving your house, or for a variety of tasks that you decide on.) We all want to do amazing work each and every time, but spending hours perfecting an underpaying post time and time again isn’t the best option since your hours are finite.

Small work can add up.

On the other hand, low-paying work with a good pay-per-hour can be totally worth your while, if it’s not one-off assignments. Especially if there are other perks involved, or you’re really enjoying the work. I would probably cover tech for less than I typically charge if it was for a high-traffic site and I had a lot of say over the angle, for example, and I do some non-profit work for practically free. Just make sure you’re not accepting underpaying, tedious work out of desperation. If you’re not having fun and you’re not getting good exposure, then you damn well better be getting paid a decent amount. And if you’re writing for something other than money (self-promotion, etc.) be very clear and upfront about it. It’s disappointing when you don’t get what you expected.

Have an anchor client.

If you can find just one client (or even a part-time job) that will help you assure your rent and bills are paid, you’ll be far less likely to pitch out of desperation or take work you really shouldn’t accept.


I started freelancing by doing writing, editing and SEO work. I’ve since gotten paid for writing test items, helping with research, editing manuscripts and academic papers, consulting, teaching classes, and even social media marketing. I’ve sold reprints, proofread transcripts, written ad copy, etc. Now I’m learning how to code. The more you can offer (within reason), the better.

It’s okay to ask for more money.

Very few professionals get upset if you do, and they often say yes (or at least work with you on scope). Oh, and don’t write on spec. Don’t write for pay based on page views. Don’t write for free or for “exposure” (beyond, say, one single article to get a single clip). Editors are not scouring the web looking at articles written for free to try to find writers to pay.


Thinking of selling a product, an ebook, an online course or a new service? See how many people you can get to sign up and pay before you create it. Otherwise, there’s no point.

Look at your contracts very closely.

That “all rights” contract means a magazine can reprint your article as an ad, which could make you look like a corporate shill. A lack of contract may not hurt in small claims, but it might. And some bozo might think that writing articles “as staff” means that he can take your name off your own work, or replace it with his own, even if your worst work is a million times better than anything he could ever write. The percentage of bad people in this industry is relatively small (almost all of my clients, past and present, are amazing people with integrity), but getting signed copies of contracts, asking for clarification and negotiating out bad terms helps you protect yourself.

Get health insurance. Dental insurance, too.

Before you need it. Trust me.

Soft skills

Rejection is a good thing.

It took me over twenty tries before I ever wrote for Men’s Journal, and Wired turns me down every month. You have to aim high. Pitching more often, and being persistent with follow-ups, is crucial for freelance survival. One of my biggest wins this year was writing an unpaid piece on spec for Lifehacker, which they rejected (despite green lighting the original idea), and immediately turning around and selling it elsewhere for $300. Another win in my career is getting rejected from a tiny no-name site and writing for one of the biggest sites in said industry. If your pitches are on-target, your writing is solid and you keep trying, you’ll get there eventually. Just don’t avoid pitching the places you really want to write. The worst they can do is say no.

People are really nervous about being interviewed.

I used to think they were acting all weird because they thought I wasn’t good at my job. Now I know that “are you sure this angle is actually interesting?” or “do you think anyone will care or understand?” isn’t an insult towards me, but just someone being self-conscious about how they’ll look in print. Had I known that earlier, I would’ve responded a lot differently.

Don’t make promises you can’t keep.

A magazine may sit on an article for a year or longer (as Black Belt did to me) or even decide not to publish an assignment, whether they paid for it or not. They might use an embarrassingly off-topic image for the piece, edit in errors, rewrite something poorly, or even completely re-spin an article to make a source look bad (in which not writing for the site any longer is completely warranted), even if they have no history of doing this (that you know of). Just be aware that you can never know for certain, so don’t promise a source fair coverage unless you get to review revisions before a piece goes live (for example).

Just because someone else had a bad experience with someone, doesn’t mean you will.

Right now, two of my best clients have reputations for being difficult, but we work very well together because I’m good at setting boundaries and they’re good at responding. People have different work styles, so make sure to use your own judgement combined with what you’ve heard or read.

Sometimes you need to be loud. No, louder.

Even if you’re brash and abrasive like me, sometimes you need to set your boundaries even more clearly. If you’re collecting on unpaid, past due invoices (or something like that), you can even hire someone to do it for you.

Help other writers.

It’s good karma. And be nice to people, even if you can’t get anything in return. Especially if you can’t get anything in return.


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  1. Yeal, I just PROACTIVELY started my first year of freelancing, so your article has perfect timing for me. (I say proactively, because I have been passively freelancing for 10 years) Your “soft skills” seem to be my everyday beast to be slain, and it’s so nice to be reminded that yes, indeed, these things plague the entirety of the self-employed world. Keep rocking the free world, my dear!

  2. So glad it’s helpful! And yes, I seem to have to relearn many of these lessons every year. 🙂 Best of luck in your journey!

  3. Thanks for this article, some very useful tips. I especially like your advice for using good tools – an absolute must – and setting boundaries in order to avoid problems.
    Risk management is a biggie when you’re a one woman (or man!) show, and it definitely pays to be pro-active in setting expectations.
    Thanks for sharing!

  4. Thanks for reading!

  5. 4 years is amazing. It’s a whole Olympics and World Cup and presidential election period 😉 Congratulations!

    By the way, which recorder app do you use for your phone? I’m looking for one as well…my old digital recorder has its days numbered.

  6. Haha, thanks!

    I’ve used Retronyms, but I wouldn’t recommend it. They have lost audio footage of mine too many times.

  7. This is a great post! I’m at three years freelancing, and I think you hit the nail on the head with everything (oops sorry to use a cliché, ha!) I also wanted to comment that this is the nicest looking blog. It really caught my eye. Visually this is fantastic! Great job.

  8. Thanks for the Trello tip. I’ll look into that. I’ve had Asana, but never really use it. Still trying to figure out my to-do list system holy grail.

  9. I second the vote for Trello – it keeps all my big ideas (and little ones) in one place with freedom and flexibility to move them around.

    Your journey is a great example for entrepreneurs in general – and I love your transparency about finding an anchor client or part-time job. There seems to be quite a bit of shame around “where our money comes from” as we identify so closely with it – but if it gives us the freedom to build our businesses the way we want to rather than desperation, it’s better to simply see that part-time job as an “angel investor.”

  10. Let me know what you think!

  11. Yael, I don’t even know where to start with how much actionable and interesting information is in this post. I wish I would have found your blog sooner. I love the bits on rejection and the practical business and money making advice. I can tell that you’ve been around the block, so to speak. Thanks for all of the great first-hand knowledge.

  12. I’m so glad it is helpful!

  13. Hi Yael,

    Your post was great and I wondered if you could please answer or help me in some of the questions I have asked in the following sentences. I have been writing for six months or so and I would like to write about technology because I did my Bachelors in Computer Science, but the thing is I really don’t remember much of it which worries me because you said that we should write what we specialize in. Please tell me what should I do to help myself recall so it becomes a little easy for me to write.

    Also can you please tell me what other skills should I learn that can help improve my writing because as you mentioned in your post that we must diversify our skills. Another thing I would like you to please mention is if you know of any free or online courses that can improve my writing and that can also help me develop those other skills in order to diversify my services.

    I hope I’m not asking too much.

    Thank you.


  14. I’ve been a freelance graphic designer for 5+ years now. Many of your lessons ring true to me but I would like to add to some of them.

    One crucial lesson that I refused to learn for a long time is SHOW YOUR WORK TO OTHER PEOPLE. It’s easy to think that by doing a good job you’ll be discovered by word of mouth, that you’re some hidden gem, spoken about by the lucky few that got the opportunity to work with you and that’s sometimes true. However, nothing has propelled my career more than taking time to create a nice looking website with case studies and lifestory FOR MYSELF. People don’t look for portfolios they look for somebody to work with. You have to come first and have some good case studies in the pocket to close the deal once you have their attention. Make the brand from yourself not from your work. It’s so much easier.

    I also couldn’t agree more on the right tools. That’s not splurging, that’s necessary. Get a good chair, good display and a computer with ssd. If you don’t feel like you deserve it now, look at it as an investment. The guilt will make you work harder.

    Karolis Masilionis
    Design and Branding

  15. Yes! I put my portfolio in my email signature–definitely agreed!!!

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