7 Time-Saving Lessons From My First Year as a Freelance Writer

Carol Tice

uphill climb business man runningBy Meaghan O’Keefe

As a newbie freelance writer, the learning curve during my first year on the job has been steep. Like Mount Everest steep.

I’m still climbing, but now I’ve got me some hiking boots and a backpack of beef jerky for the road.

These are the important lessons I’ve learned along the way:

1. Keep trucking

It took me a good long year to build enough momentum to feel like I was getting somewhere with growing a client base.

Every time I had a positive interaction with a potential client, I thought I had made it. But building a business takes time and can feel agonizing.

I kept thinking the opportunity I’d need was right around the corner. And it was….just a corner several hundred miles down the road.

2. Don’t take out loans from the worry bank

I had my first mentoring phone call with Carol Tice and Linda Formichelli while I was still working full-time and trying to jumpstart my freelance career. I also have two young kids, so I was really worried about balancing all of that work that I thought was going to be thrown at me.

When I voiced my concerns, there was a pause (and probably some internal laughter on the side of the mentors) followed by some good Carol Tice advice, both for freelancing and for life.

“Don’t take any loans out from the future worry bank,” she said. “Just focus on what’s happening now, and take it a step at a time.”

In other words, don’t worry about things that haven’t happened yet, dummy.

3. Hurry up and market yourself

Oh! The AGONY of writing letters of introduction.

How do you sell yourself without sounding sales-y? How do you pull off professional, interesting, and somewhat funny all at the same time? There’s only one way: practice writing them and expect them to bomb.

Only after about the 100th letter did the desperation and fear start to wear off.

You realize that one LOI can soar, while another might tank. You might even find yourself getting a little light-hearted.

Once you accept that the majority of LOIs go nowhere, the importance dwindles a bit. So just get those first hundred over with and get on to the good stuff.

Chances are, the potential clients you send those newbie LOIs to won’t remember you when you hit them up the second time around.

4. Define some ‘Store Closed’ rules

As a freelance writer, typical working hours don’t really apply. Which makes all hours fair game. Big bonus and huge liability.

If you check your email constantly, you can feel an immediate need to respond to whoever is emailing you — or if your mailbox is empty, you can develop major anxiety about no prospects.

Or if you have two hours at the end of the day without other life responsibilities, you can spend them treading Internet water for possible gigs.


You need to figure out when you’re “off,” because nobody else is going to do it for you. You’ll spin your wheels more than work if you let the business stuff leach into every aspect of your life.

5. Balance immediate needs with career goals

At this point, I’ll pretty much do anything to receive compensation for writing. Except for working with a terrible client (a bad client IS worse than no client.)

But long-term, I have plans for the kind of work I’d like to be spending my time doing. Balance those work decisions between your immediate needs and where you want to end up in two to three years.

6. Get a little arrogant

You’re a good writer. Seriously. Shout it, loud and proud.

You might get turned down because you don’t have the right clips yet or the client’s budget is tight. But if you start to think it’s because your writing isn’t any good, you might as well just give up.

Having faith in your writing skills is the only fuel you have when the going gets tough.

7. Don’t forget to write for fun

Marketing yourself is such drudgery. Blech.

After a couple of months marketing without much work I completely forgot that a) I loved to write and b) I was actually good at it. I don’t care how good you are at LOIs and queries, they’re never going to win you that Pulitzer.

So if you have your own blog, write for it. Or work on that novel of yours. Or write some poetry.
Just write something—get the passion back.

What lessons have you learned as a freelancer? Share your wisdom in the comments.

Meaghan O’Keeffe is a freelancer who writes about parenting, health, and wellness. 


  1. Alexandria Ingham

    Great post, Meaghan. I will second the write for fun! I spent the first few months or so of my freelancing career focusing on writing for money and marketing. I lost sight of what I loved about writing and started to wonder why I chose to do it. I now have a personal non-profit project that I work on at least once a week. It keeps the creative juices flowing and reminds me why I love writing so much, especially if I have a PITA client. I also have a few blogs and write for other sites on subjects that I just love to write about.

    • Jon Clayton

      Good advice. Timely too. Thanks!!

  2. Jessica Flory

    Really great post! I especially love the “define some store-closed rules” because it’s soooo easy to ignore this one. When you work from home, there’s no specific point when you “leave the office.” You know, when you get on your coat and drive home to relax. But relaxing and taking breaks is very necessary to being able to do your best as a writer, so setting a time when you’re done for the day is great advice.

  3. Erica Ellis

    Thanks! I needed this one today! Especially the “worry bank” part. I am a frequent customer there. 🙂

    • Carol Tice

      Well, I’m the queen of it — I got that saying from my sister, who used to tell ME to stop doing it. 😉

      • Jeremy Wiebe

        I need to take that and frame it. Or stamp it into my contact lenses (wouldn’t work, I know) or SOMETHING. Thanks, Meaghan and Carol, for the indispensable advice.

        I like to think of Stephen King whenever I get a rejection. He stuck every rejection letter on his wall like he was collecting them. Makes me feel like Rocky or something when I can just stand there and take a beating.

        • Carol Tice

          When I was a kid, Jeremy, I had a teddy bear. His name was Teddy Yussell Dog. And what I used to like to do was punch him! My dad said that was good — I was “toughening him up” for the real world. And that is how we have to be. Life’s tough, and then it’s over.

          Be an unstoppable force and keep going in the direction you want. Don’t let anybody tell you you can’t. That’s all there is to success in freelancing.

  4. Deevra Norling

    Ah…thanks for this post. I am feeling the drudgery and pushing and straining for that breakthrough. I haven’t got around to the marketing bit yet because fortunately i had a few clients come my way from a referral. I sometimes wonder what the hell I’m doing as money is not exactly flowing in at the moment and I wonder if I’ll ever make a decent living from this. But like I said, I haven’t done much marketing yet so will see how things go once I start putting myself out there – which I have to admit I am not looking forward as it is about selling yourself and I hate sales!

    • Meaghan

      Hi Deevra. I totally get where you’re at! I find the drudgery comes in waves. Sometimes the only thing I can feel optimistic about is that “this” wave will subside, because it always does!

  5. Rohi Shetty

    Thanks a ton, Meaghan,

    My biggest takeaway is to write more than a hundred LOIs.
    Pure gold!
    Reminds of “Everything is hard until it becomes easy.”

    Thanks also for sharing Carol’s admonition about taking loans from the future worry bank. So true. I’m looking forward to her training on affiliate marketing in the Den tonight.

    Life is good.

    • Carol Tice

      Rohi, that training recording already went out to the members, you can watch it anytime — check the recordings page or your email for the link.

      Then if you have any questions post them in the “Questions for Den Meetings” forum thread in the Den for this week’s event.

  6. Rohi Shetty

    PS My best productivity tip:

    Stop watching TV.

    Just. Stop.

    • Carol Tice

      That’s exactly what I did when I was building this blog. I just didn’t watch TV. Had no idea what shows were hot.

      It’s more fun to get them on Netflix and watch a series all at once anyway, once you’ve got the time to catch up, I say! Doing that now with Mad Men, which we had never started.

      • Meaghan

        Carol, I’m jealous of your Mad Men innocence. There’s nothing like finding a new great series.

      • Meaghan

        Yes! Facebook is one of my worst enemies.

  7. Robert

    Looks like you learned quite a bit! I definitely agree with you when it comes to having “off” hours. You have to have balance in business. Of course, you still have to meet customer expectations, so depending on your industry, you have to figure out how to operate. If that means bringing on help – that’s what you have to do. Great post! Thanks for sharing!

  8. Erica

    Thank you so much for this post! It’s just what I needed to hear, especially about taking out loans from the worry bank. I’m up to my ears in debt to the worry bank right now but you (and Carol) are right. So very very right.

    Two more tips: Exercise regularly; make it part of your routine. And don’t let other people push themselves into your schedule just because your hours are “flexible.”

    • Meaghan

      Erica, exercise is a really good one. I’m just learning that one myself. It helps my mood and helps create a sense of structure!

  9. Sheila Bergquist

    Always such great advice Carol! These were all things I really needed to hear right now. The inspiration we get from people like you is what keeps us going…seriously! I especially needed the “get a little arrogant” advice. Others tell me I am a good writer, but deep down, I sometimes wonder! It is so important to believe in your talent. Thanks for the reminder.

    • Carol Tice

      Well, it’s Meaghan’s post, Sheila…but I thought it had great tips, too. 😉

  10. Ahlam

    Definitely don’t forget to write what you love. Otherwise, writing professionally can drain your creativity.

  11. Kimberly Jones

    I love this post! Last year was my first year on my own and I learned a lot from seasoned professionals (including you, Carol). One big thing I learned was to never under-value my services and I have passed this lesson on to many of my small business clients. If someone doesn’t want to pay me my going rate, then I can send them on their way and open my schedule up for someone who can afford me.

    Also, a shout out to “The Renegade Writer” who gave me a very important tool to be happy with my freelancing career: Decide what I really enjoy doing and make that my focus. I really like working with small businesses and, therefore, I focus on small business clients.

    Also, until the clients start rolling in, spend the time you have free to focus on learning as much as you can, reading books on freelance writing, joining reputable and beneficial freelance writing communities (such as The Writer’s Den), signing up for freelance writing mailing lists (Firepole Marketing is a great one that I haven’t mentioned yet, as is Copyblogger) and reading blogs on the subject. Reaching out to experts can help you navigate your way through the process of building and growing a freelance business, which can be daunting at first.

  12. Josh Brancek

    Don’t forget to write for fun – One of the best rulles I can relate to totally!!!

  13. Jessie Kwak

    Thanks for including “Don’t forget to write for fun.” For the last several months I’ve felt like every available moment I had to write should be spent on projects that would advance my freelance career. That fantasy novel I’ve been plucking away at didn’t seem to fit the bill.

    But lately I’ve been carving out an hour here or there to write it, despite my limited time. It’s so rejuvenating to be spinning stories instead of churning out LOIs! I just spent the morning working on it, and now I feel refreshed and eager to tackle those more mundane freelance projects I’ve been putting off.

    Thanks for the great post!

  14. Darlene with BlogBoldly

    Well, I’m not a freelancer.. but a lot of your tips work for any home based business owner.

    For example #4 Closed Doors. I work full-time online and if I didn’t implement a closed door policy, I’d go crazy.

    What tips can I offer? Hmmmm..

    1) Have a plan and treat your business like a biz.
    2) Schedule your tasks so you will work your biz consistently.

    ~ darlene 🙂

  15. J'aime Wells

    Oh, wow, I was putting off reading this, not thinking that I really needed “time-saving” tips, but this is actually a much deeper post than the title implies. Thank you, this is really helpful and encouraging. I need to write down “Just get the first hundred LOIs out of the way” and stick it up on my wall.

    • Carol Tice

      Seems like that piece of advice really struck a nerve around here!

      I do think a lot of writers don’t understand the volume of marketing that’s needed, or how important it is to get good at it. Repetition is pretty much the main teacher, too…loved that tip.

  16. Jawad Khan

    Hey Meaghan,

    Great point, specially no. 3 and 5.

    Theres no other choice but to market aggressively and on a continuous basis. You need to keep new leads coming in.

  17. christa sterken

    Good post! I loved the part about taking out a worry advance. Thanks for a piece that encouraged me today, I needed it

  18. Bob

    After cutting through the fluff, this confirms what a tough slog freelancing is.

    There aren’t many real opportunities out there, clients are cheap and difficult to work for.

    Writers need to be dogged.

    It is rational to be discouraged and to worry.

    Forget about writing for fun.

    Gordie Howe wrote a book called “Hockey is a Battle.”
    Freelancing is a Battle.

    • Carol Tice

      Hi Bob —

      I don’t share your negative viewpoint and believe there are MANY great opportunities out there, particularly pent-up demand in the small business sector for online writing help such as web content and blogs.

      Worry is like rocking in a rocking chair — you feel like you’re doing something but you don’t ever get anywhere.

      You do need to be dogged though…agree with that part.

      And DO NOT forget to write for fun! Otherwise what’s the point?

  19. Amy J.V. Atwell

    Great post. I am six weeks into my first year as a freelancer, and the ebbs and flows have already started to get under my skin a bit. I have been writing for fun during the ebbs – keeping up with my garden blog and such – and that is really a sanity saver.

    • Carol Tice

      I think that’s a terrific idea.

      The trick is to go out and enjoy the down time and not be sitting around biting our nails. Last night as it happens I was actually out slacklining with my kids instead of working on book marketing for my book launch day today. Because sometimes you just have to do that.


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