10 Things I've Learned While Freelancing

April 17th marked my 1-year anniversary as a full time freelancer. This month marks my 2-year anniversary as any kind of freelancer. During this time I've learned a lot of stuff that may or may not be useful to you.

1. The easy way is usually not the best way. Chances are good that if nothing in your career ever excites you, scares you, intimidates you or challenges you then you are doing it wrong.

2. Not all writers are created equal. You are probably better than some writers and worse than others. You may have a great voice for some work, and a terrible voice for other work. You might know a lot about some things and nothing about other things.You may be able to improve in some of these areas with hard work and study. You may not. Either way, it's not necessarily a career-breaker.

3. Not everyone is going to succeed. Don't feel guilty if you are one of the writers who does.

4. You need freelance writing friends. I know there are some people out there who are lurking. They read the blogs, work from home, write for a living--but don't make friends with other freelance writers. I think this is a huge mistake. My freelance writing friends are great sounding boards, terrific resources, awesome motivators and they understand my triumphs and setbacks like almost no one else.

5. Your mistakes will not make or break your career like you think they will.

6. Don't let fear rule you/ Good enough is never enough. If you are afraid and/or if you allow your career to stagnate you will never know what you could have been, what you were capable of and how far your career could have gone. Don't be afraid to put yourself out there, take risks, and really challenge yourself. If you let fear stop you or if you settle for "good enough" then that's probably the best you will do. Imagine knowing that the career you have right now is the best you will ever, ever do. You will never get better clients, better gigs, better bylines, better money, better fun, etc. Sad, huh? Is that what you really want out of your life?

7. Highlight what you want your potential client to focus on. On my portfolio, resume and cover letter, I focus on my licenses and experience in the financial industry. I do not focus on the fact that I have yet to finish college. There are almost no deal breakers in this business--you just need to adjust your marketing message so your potential clients pay attention to what you want them to see. Kind of like how I always show too much cleavage to distract from my love handles.

8. Don't be afraid of your voice.

9. You have to create the career you want not just by dreaming about it, but by deciding what steps to take to get it and then doing them there steps. Your career does not make itself--you have to make it. And proactively, I might add.

10. There are no secrets, no formulas, no gurus, no superstars, no guarantees. There is just you, time, your keyboard, your motivation and your determination. And even that is not a recipe for success.

So how about you? What things have you learned?

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Yolander Prinzel is the profit monster behind the Profitable Freelancer website. She has written for a number of publications and websites such as American Express, Covestor.com, Advisor Today, Money Smart Radio and the International Travel Insurance Journal (ITIJ). Her book, Specialty Ghostwriting: A New Way to Look at an Old Career, is currently available on Amazon.

55 thoughts on “10 Things I've Learned While Freelancing”

  1. Nice post. I learned that we all have to make the choices working best for us, even if others don’t approve. I think too many of us build our careers (freelance writing or otherwise) based on what others think we should do, instead of following our hearts. I don’t know that there’s a right or wrong way to be a freelance writer, and we only have to find the best way for each of our individual situations.

  2. Some fantastic points, Yo. 4 and 5 in particular I would pay extra care and attention to.

    I have a cilent who I do a lot of work, who I started writing for when I was just starting out. My rates were low and earlier in the year I wanted to increase them, but was, well, I was petrified of doing so If i’m honest because I feared that if I increased my rates with them, they would say no and that client, who I do a lot of work for, wouldn’t send any more work my way.

    After several e-mails to Jenn here, she persuaded me that I was most probably worrying about nothing – and she was right. I actually got a deal better than I could have expected.

    • It’s funny because I think 4 is overlooked the most–but is really, really important. Another thing that I did not mention is that when you make friends, you tend to get more referrals. That’s not a reason to start sucking up to people, but when you are good and dependable and you hang out with the right crowd, you will find many more opportunities coming your way. I have quite a few editor friends and they hire me for stuff often–it makes their life easier because they know I’m worth it and reliable and makes my marketing easier.

  3. Great post, I love your honesty. I agree, one of the most important things is having other writers in your life. It helps to have peers around that you can celebrate with and learn from on a daily basis, who can encourage you through the tough times.

    • I hear ya. As much as my hubby tries to pretend he understands what the heck I’m talking about re: my career…. he doesn’t always really get it. Writer friends always do!

    • Honesty is definitely one of Yo’s best qualities, so if you haven’t read her other posts, I hope you will (she writes here every Friday).

      Encouragement from colleagues is always a good thing to have, no matter how long you’ve been in the game. There will always be tough times — maybe slow work periods or just an occasional lack of motivation. And having someone to help hold you accountable never hurts!

  4. Great, great comments and observations. Meeting other freelancers is my No. 1 motivator. Almost everyone I have met through Twitter, friends of friends and on my own have been helpful to my career and are people I would want to be friends with anyway. At times I’ve found myself freaking out about moving into the freelance world, and those friends have been the ones to say it will be OK. It’s easy to trust them because they have been there, too. None of it has been easy so far, and I don’t believe the road ahead will be smooth sailing, but I’m looking forward to more challenges.

    • That’s key — having people in your life who have gone through the process of going freelance. Sometimes people outside of the freelance game just don’t get it (although some do). It’s nice having someone around to knows freelancing is a “real job,” especially in the beginning.

      • Yep, because the reaction I got from my parents was “you’re going to do what?????”

        Thankfully my husband is very supportive and so are my friends. Sometimes doing too much reading makes things more intimidating because it seems like everyone is already successful without any worries. It’s reassuring to know other writers who struggle, fail at times, get their feelings hurt, etc. Most people don’t want to share those details, but it makes them seem more human and real. Definitely reassures the rest of us that even though things seem hard now, it’s not impossible!

        • Oops, didn’t see the one about struggling. Everyone struggles at some point or other (and some of us at several points). Sometimes the struggles are real and sometimes they are just mental hurdles we must overcome. But no matter how glossy someone’s exterior is, never doubt that they struggle from time to time.

        • lol My mom didn’t stop randomly dropping off job ads until she needed to borrow a good deal of money and I was the only one of her kids with enough to give it to her.

          Really… we all fail sometimes. We’re big on sharing both successes and failures here. They’re both a part of life and freelancing.

        • Till the day he died, my father-in-law would always ask me, “So, when are you planning to start a business?”

          *insert sound of head slamming on keyboard*

          At first it really, really pissed me off, but eventually after about the 20th time, I just kinda went with it. “Yeah, I know I should, but I’m doing pretty well with what I’m doing.”

          He wasn’t trying to be a jerk, he just simply didn’t understand that I could support his daughter (a stay-at-home mom!) and grandchildren without wearing a suit and tie every day. He was a PhD in chemistry and worked for the same paper company for 20 years, so I suppose I was a wee bit outside his experiential zone.

          My dad always got it, because he was an independent, self-employed, stubborn S.O.B. like me.

          • I think that was a part of my mom’s issue too. She’s of the mentality that everyone should be with a single employer for most of their careers. Life just doesn’t work that way anymore. Hell, I remember back in college being told to expect at least 5 major changes / employers in your career. Someone I know who’s a bit younger was told to expect more. When employers cease to be loyal to their staff, it’s no wonder things are different now. Throw in the Internet and the ease of freelancing (compared to starting a brick & mortar biz) and is anyone really surprised that so many people would choose the independent route? Not me.

    • It’s funny Ashley because there will be things for you that are easy that weren’t for others and vice versa. That’s just how it goes. Sharing stories definitely helps because it helps you feel better and makes you realize where your strengths are.

  5. I’ve been doing this more than a few years now and it still stings every time I get rejected or criticized. Even for things that I know are completely false or misrepresented. Learning to constructively handle that criticism and moving to a place where I’m confident and sure of my position are key motivators for me.

    I also would love to show more cleavage, but toddlers keep grabbing my shirt when I pick them up so I guess it’ll have to wait a while longer – maybe I’ll spring for some new cleavage down the road anyhow.

    • Just wear a lot of eye make-up for now. That’s one of my other tricks 🙂

      Yeah, criticism always hurts a little. But when it’s right, it is really helpful in growing your career.

      • Nah, this isn’t even warranted a PG warning. Apparently I need some more eye shadow to really spice up my life.

        Good post, Yo, obviously it’s resonating with people. I agree that I learn the most from criticism, even if it’s hard to take at a times, but it’s a fact of life in any area that’s challenging. If you’re perfect all of the time, you’re not trying hard enough or pushing yourself far enough in my book.

        • “If you’re perfect all of the time, you’re not trying hard enough or pushing yourself far enough in my book.”

          Amen to that! Of course, if the occasional client is easy to please and they pay my rates, I’ll take that too! 😉

  6. I double, triple, quadruple…uh, you get the idea…the comments here.

    Another thing I learned, is be selective – in many ways. Be selective in your clients, be selective in your gigs and be selective in the freelance writers you hang out with (even if virutally).

    It is very easy to get overwhelmed, abused and get caught in whining & complaining ONLY (hey, we all need to some do it sometimes). It takes way too much of your energy and is a mental and physical drain. So, as Ben Bailey says on Cash Cab for street shout-outs: “Choose wisely.”

    That’s why I hang out with AFW. 🙂

    • Be selective in your clients, be selective in your gigs and be selective in the freelance writers you hang out with (even if virutally).

      Very good point. And it’s about more than being selective pay-wise. Who you associate with affects your professional reputation. Taking a porn gig when you’re a parenting writer is probably not a smart idea. Neither is associating with others in your industry that you consider “bad apples,” especially if it might be construed by your own readers or colleagues as support or a recommendation of that person, site, or whatever they’re “selling.” You need to be true to yourself, and you have to be able to make responsible decisions — even if it doesn’t make everyone happy all of the time.

      As for why you hang out with us… we’re not naive. We know it’s just because we slip you chocolate under the table. 😉

    • Seriously. There are always emotional and business “drains” out there. There are takers who never give back, people who put self-interest above everything else, those who run away from different opinions and those who would want to complain and become martyrs. Boooooorrrriiiinnnnggg. It is very rare that I actually dislike people (especially those I’ve only met virtually) but there are definitely individuals that I’d rather not associate with because they drain me and don’t add anything to my life’s experience.

      • Same here — most other people in the niche are rather pleasant, regardless of whether or not we agree all the time (hell, you and I don’t agree all the time, and I still put up with you!). 😉 But every industry has its bad apples, and I think you covered a few great examples. I’d add one from the recent SI conversation too — the newbies masquerading as experts. That’s something I don’t have much patience for now that it seems to be “the thing to do,” especially online.

  7. I think I gave an example of Not all writers are created equal we all need to some do it sometimes Say what???

    Make that – we all need to do some of that sometimes **Phew**

  8. Hell yeah!

    I realise I’ve kind of entered the conversation at the last minute. I was a bit hung up on the whole Clint-porn-low-cleavage thing a few comments back.

    Us English can blush easily, you know.

    • Oh I know – I’m of Scottish and English descent – dating back to the Mayflower, no less, and still my whole family is pale as ghosts and turn beet red rather easily.

      But why would you be embarrassed? You crazy Englishmen have the most outlandish, dirty slang I’ve heard in my life. 🙂 Not you in particular, but you know what I mean…

      Maybe that can be #11 – Learning about written expressions and cultures from around the world. 😛

      • Dirty slang? Queen’s English with no profanities all the time for me, darling.


        I didn’t realise how bad we were until recently, when my Girlfriend told me she didn’t think I could go half an hour without swearing.

        I failed. Miserably.

    • lol Have English and Irish blood too, but the German in me wins out so I avoid the apple-cheeked look. And she’s right… the Brits I know are some of the most vulgar little things. Can’t imagine them getting easily embarrassed.

      Damn Rebecca. Sounds like you have me beat by almost a decade. My English line came around 1629, so not quite the Mayflower period. They founded a couple nice cities up in CT though, so they didn’t do half bad. I’m still shocked that I’m descended from a Puritan minister who was apparently a big deal at the time. He’d be so ashamed of me…. 😀

      • Nope – we’re descended from Miles Standish, captain of the Mayflower. At least I get the sea captain ancestor to help defend my lifestyle, but I also get two presidents (the Harrisons) in the direct line, so bummer. LOL

        Puritan minister…LOL…I hope he wasn’t in Salem. *wink*

        • lol No. New Haven, then Milford (gorgeous town btw). No witch trials that I’ve come across yet. And if there were, then I’d just be equally ashamed of him, so we’d be even. 🙂

          I wonder if your sea-faring ancestor ever came across the Irish pirate side of mine in any of his voyages. (I have a colorful family history. lol). The O’Flaherty clan. Still trying to determine if there’s a direct line to Grace O’Malley or not. As for your Harrisons connection… could be worse. You could be related to Bush. 😛 (and now I’ll quietly slink away hoping you weren’t a Bush supporter lol)

  9. Respect knuckles, Yo. You’ve gotta keep fighting the good fight and rely on your own strength, in writing and in life.

  10. Geez, I guess I’m a little late to Yo’s 1st Anniversary Party. Someone pour me a margarita already!

    Not surprisingly, I think your 10 things are right on the mark.

    The only thing I’d add, and maybe it’s 6a, is to “Let it go.” You aren’t your job or your creative output or the checks that come in the mail. As a creative person, you have to be really objective about how your work is received, almost to the point of not caring at all. Don’t get too high when you get rave reviews, don’t get too low when someone is a hypercritical a-hole. It’s a game, folks…maybe a high-stakes one, but it’s a game.

    Congrats, Yo! It’s good to have you as part of the Freelance Mafia.

      • Have you read 10-10-10 by Suzy Welch? I had the pleasure of interviewing her for an article in Speaker magazine a few months ago.

        The basic principle is looking at what the impact of an event or decision is going to be in 10 minutes, 10 months and 10 years. I figure most of the mistakes we make *don’t* have an impact 10 months down the road, even if it seems like the end of the world at the time. By then (usually) I can laugh at them from the “what-a-stupid-I-am” perspective; or, the educational value was the price of misplaying my hand.

        It’s not rocket science, and it’s similar to things we’ve all heard, but Suzy packaged it in a very accessible way, with lots of good anecdotes.

        • That said, when we DO f* up royally we have to be prepared to own up and fix it or be ready to leave.

          I remember a freelancer (oh maybe 1-2 years ago at this point) who was caught taking advantage of their sub-contractors, trying to get out of paying them (with no legitimate reason). As if that wasn’t bad enough, while defending themselves they tried to say “I never said ….. to clients.” Only, they did. There was a public record of it because they said it to clients in a public community. They were called out. They had no way out, that information still ranks highly for their name in Google when potential clients would search for them. And they vanished off the face of the earth — couldn’t recover the branding.

          So while most of our little screw ups won’t affect us in the grand scheme of things, what seems like a little complaint can snowball when you’re exposed. That’s why it’s so important to always be honest with people (rethink those client excuses!), especially when so much is publicly documented — and on other people’s sites where you can’t delete it later.

  11. I’ve learned to celebrate what I call the little victories. I’m still in the process of getting my business off the ground. But I have these little victories that have happened, such as getting my guest posts published on some well-established blogs, that keep me going strong.

    I really appreciated this post. It gives me more motivation to continue with my pursuits.

  12. Here’s one thing I’ve learned.

    Don’t believe everything you read. When I started out a few years back, I bought a couple of so-called web writing books. Taking the advice I learned, I started out in a keyword stuffing mill position. Worst experience of my life. To this day, I cringe at the word-keywords.

    Long story short- I had to rebuild myself as a Freelance Writer. I learned more about getting started from various blogs then I did from buying those books. There’s nothing wrong with buying books on Freelance Writing, but make sure you’re getting a good one from someone who’s been there and actually knows what they’re talking about.

    I agree with what you’re saying about making friends with other writers. The only problem is some people make friends for the sole purpose of getting you to help them get started. They don’t want to do all the research and sweat it takes to build their own business. They want you to do it all for them and you should have done it yesterday already!

    • There are definitely some people like that. But they’re usually easy to identify early on, so the more experienced writer sees they’re being used and can decide whether or not to “become friends.” That said, I don’t think asking for help necessarily puts someone in that group. I don’t mind helping people out, but only if I can make the time (during work). If they’re asking for a blueprint, they get ignored or they get links to the blog. If they have a more specific question about their own situation, I always try to answer if possible. That’s also how I met some of my current favorite writer folk.

      I agree about Web writing books. I’ve yet to find a single decent book on Web content writing. Frankly, I’d say any pushing mills are from the inexperienced or sell-outs, so I could never take them seriously or recommend them. And then you have the IM ones you mentioned, where it’s usually very old school SEO advice that isn’t even relevant anymore (nonetheless ethical).

      • My start with the mills was very organic. I actually got my first gig with a local paper and then started looking into web writing which brought me to Helium and so on. I don’t actually regret this start–it was sort of like baptism by fire. I just wish that I hadn’t thought it was the only way. It’s certainly not a required start–or even a good start–for a newbie.

  13. Quote: “Not all writers are created equal.” I totally agree. Writing must be all about passion in what one knows best. Not everyone has the same ideas and writing style. For me, I’ve learned that freelancing is all about resourcefulness. I set my own metrics on my own performance and it is a continuous journey of learning. Thanks for the lovely insights, by the way.


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