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. 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.

  2. 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?

  3. 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

  4. 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.


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