29 Freelance Writing Challenges For The Next 12 Months

Updated: March 2017

29 Freelance Writing Challenges

The number is 29 because I turned 29 on June 17 (2014).

Yup! I have only one year left in my twenties and, as a writer, I want to get the most out of it. 😉

Are you up to the challenge, too?

Because you see, these challenges are not here just for myself as a reminder, but to inspire you to take action and work toward your goals with a bit of healthy spirit of adventure.

29’s the number, folks!

Here are the freelance writing challenges I took up to enter my thirties with a bit of glory and more writing opportunities under my belt. (More clients, too?)

1. Speed up that writing! Get to write 2 posts a day

Okay, maybe not two complete posts ready for publication, but at least two complete drafts with research.

I need to get faster at writing if I want to earn more. Also, since most of my slowness is caused by anxiety attacks, tachycardia and a fear to burnout, this challenge is a good push to take more care of my health.

2017 Update: definitely NOT 2 complete posts a day! But I found out I can write up to 1,500 words a day without overloading and risking a meltdown, 3-4 days a week. Sometimes more if my mind functions better, other times less if I shut down completely.

2. Kick those guts and go interview someone!

If you’re wondering– in English and yes, with THAT Italian accent!

Oh boy, you won’t believe how scared I am to speak English! I can write and read English, but my listening and speaking skills are still kind of raw.

I rarely get to practice in Italy (nobody speaks English home either) so I’m frightened that an interviewee may laugh about my accent and my “can you repeat that, please? Slowly?” and quit a phone call before I can even get a quote.

This fear is a never ending vicious cycle and I need to break it.

Now, I have a few English-speaking writer friends on Skype and I may just reach out and ask for help…

2017 Update: still working on this, and trying to find a ‘warm-up group’ of friends and writers to practice with. Interested? Let me know via email at luana@thepenthinker.com.

3. Dedicate more time to MY projects (not just clients)

I’m not sure when that started, but I realized that I’ve come to dedicate more and more time to clients’ projects and less or no time to my own projects.

Big fail. Seriously. If there’s something I always wanted to do on the Web since I made my first website back in 2003, that’s being myself, letting my voice speak up and get my slice of personal success.

But where’s my success if all I’m known for is blog posts for my clients (when I’m not ghosting)?

I have two grand projects to launch this year — Biz Character Blogging and Sponsored Circle (2017: now merged with n0tSEO) — and I’m not going to keep postponing them because of client work.

Reminder to myself: go make time for the two biggies, Luana!

2017 Update: I have kept my blogs on hold for a long time due to health issues – and the little energy and time I had was spent on client work. Now… back to business. 🙂

4. Write a White Paper for someone

That’s right. For a real someone– not just my beloved fictional characters and their world.

White papers are big projects and they still scare me a little, but I can’t overcome my fear if I never give it a try, right?

The worst a prospect can say is ‘no’, after all…

2017 Update: getting there, both with fictional and real projects.

5. Act! Be bold!

Pitch blogs and magazines I still feel to shy to even just fan mail. Go go go!

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No matter if the publication pays or not– this is about developing guts — and some additional writing, niche, industry experience. It’s about taking action!

I’ve been scared and filled with self-doubt for too long in my career. Time for a change.

2017 Update: I still have my ups and downs, but getting there.

6. Find US or European magazine I can use Italian sources for

Because these are the only sources I can interview in person. And I have to break the ice, sometimes.

For example, Italy Magazine might be a good place to start with. 🙂

Note: I can’t write for Italian magazines for profit because I’m not a member of the Order of Journalists, but I can contribute to local papers for free, and to blogs and online pubs. However, clips like these could help me land assignments with bigger (non-Italian) pubs like OSIA  in the future.

2017 Update: I still mostly work with clients outside of Italy and EU, but I’ve been copywriting a website for an Italian client since January 2017, so I’m slowly extending my client pool.

7. Record video tips for ProBlog and other blogs I run

Not just to break the ice, but also because it helps to see a face — and hear a voice — besides reading words on screen.

And to stop fearing to get bullied for my Italian accent. Uhm.

2017 Update: I started publishing book review and opinion videos on YouTube – in Italian – as a warm up. Progressing from there, even though I won’t have a quiet environment to shoot until I move out (in a few months!).

8. Remember that being 29 or 30 is not the end of the world

This challenge might not appear strictly related to writing, but I can assure you that it matters– I tend to buy (emotionally) into the talk that a person’s thirties means we’re getting old and what’s been done, has been done. No more.

Well, I believe that I’m still young and there’s so much I can do, create, WRITE!

When I turn a century old, maybe, I can allow myself to say “Now I can rest and be proud of the things I’ve done”… or maybe not? 🙂

2017 Update: Going-32 is not the end of the world either! 😉

9. Learn to program and write about programming

I’m still afraid to program.

Yeah, I mean computer programming: PHP, C, Java, etc. I’m a Computer Science forced drop-out, but my heart never really dropped out. Yet, I still feel as if I’m never going to really learn how to program.

But how can I write about programming — especially tutorials — if I don’t learn how to program, first? Impossible, right?

Already got started on C and PHP, so get on with it! Program and write! 🙂

2017 Update: I published a couple of WordPress PHP programming posts in 2015, but going to do more as I learn (right now? I have intermediate skills at best).

10. Finish (and self-publish) at least one novel

There’s a Sci-fi/romance novel I started several years ago that I never got myself to finish. If something like a “fear of completion” exists, that’s what I have when it comes to fiction.

I think it’s about cutting the umbilical cord– these characters and their story are my children, so I’m scared to send them out in the world.

The poor characters are knocking hard inside my heart and mind to have their story finished, though, and people who were anticipating my novel are eager to see it written and ready to read, so… I made finishing this novel one of my To-Do Before 30s list.

2017 Update: I thought it was easier? LOL There is still plenty of work to get done on this novel, so my next self-imposed deadline for it is to get it ready for an editor by December 2019. Let’s see what happens.

11.  Publish case studies

Because I have several in the works but I seem to be scared to complete and publish them.

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Scared of what? To ‘upgrade’ my skills, it seems. To be called “the incompetent writer who was so arrogant to try formats that go beyond her skills”.

Silly me, just as silly as per #10 and #12 in this list.

2017 Update: I published one case study in blog post form in 2016, but that’s not the end of it. I’m gonna do more!

12. Stop thinking I write crap

My clients and writer friends say otherwise, so that means something, right?

No more self-sabotaging.

2017 Update: I self-sabotage every time my confidence and self-worth throw themselves into a pit – but I’m finally seeking help from a therapist, so that should improve in the future. I know much of that is due to childhood bullying; I must face my ghosts.

13. (Re)Learn to write an entire blog post on paper first

Start to finish. An entire blog post draft in one sitting, letting nothing and nobody stop the flow.

I’m so used to getting interrupted at home that I unconsciously interrupt myself every 15-30 minutes or so. I know why my brain does that (it tries to anticipate the ‘shock’ of interruption by provoking it on its own), but it’s frustrating nonetheless.

I have to (re)gain control over the flow of thoughts if I want to speed up my writing (see #1).

2017 Update: check! Mostly in the form of mind-map and bullet points, but yes, I do this kind of regularly now. Lessens the risk of sensory overload from the computer screen, too.

14. Remember that my short story collection awaits…

… and readers, too. 🙁

I had to self-publish my Lights of Metal and Sky collection around October 2012 originally, so that says a lot about how behind I got on those stories.

2017 Update: getting there 😉

15. Find a new work-study balance

It got messed up after I dropped out of university (not officially yet, but I no longer pay tuition, so I’m an “on hold” student).

Once again, I tend to buy into some people’s line of thinking that “you either study or work, you can’t do both”, exactly when my heart speaks differently.

I have to remind myself that I owe it to my love for Computer Science, Technology and other subjects if I can call myself a freelancer. If I don’t keep studying, I may quit freelancing as well.

2017 Update: self-learning FTW! Back to uni someday, too. 

16. Learn some electronics and circuit logic

See #15. 🙂

And then, there’s no way I can write for those fabulous electronics magazines I read all the time if I don’t learn some electronics first!

2017 Update: doing this for a personal robotics project, and I’m pretty sure it’s going to turn out useful for my writing business, too.

17. Write and publish all the ebooks in my To-Do list

Because I have many, most of which are started or half-written.

Doesn’t matter if I can’t get to finish and publish them all, but I should at least try.

And if you read the above Challenges, you’ll notice a pattern. 🙂

2017 Update: ticked one off the list! Now on with the next… 😉

18. Practice Catalog and Direct Mail Copywriting

With fictional characters, of course.

And my business websites.

The soonest I learn the crafts, the soonest I can add these forms of copywriting to my list of services.

2017 Update: work in progress!

19. Publish Press Kits and Press Releases

For my blogs, services and projects, to start with. Maybe one or two for my friend Lia Dospetti’s Robocity World (2020 update: now renamed into Rolamaton The Robocity) too.

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I need to get faster at planning and writing these pieces.

2017 Update: I published one press release in 2014 for my ex-project Sponsored Circle, now merged with n0tSEO. Press kits are still difficult for me to create, but hey, getting there! 🙂

20. Learn to write Business Plans and Corporate Profiles

Probably with Characters only until I feel confident enough, but it’s a start! 🙂

2017 Update: got started and so far it’s fun!

21. Add columns and monthly features to Writer’s Mind

I want to make this blog even more interesting to creative and freelance writers!

2017 Update: as per Italian law, I can’t turn this blog into a magazine without registering (and paying, ugh!) it as such, so I will be reworking all the categories in 2017 to be more similar to columns, but without set days and no permanent editorial calendar. I wish the law made it easier for Italian bloggers. 🙁

22. I script and draw comics, right?

Then I should definitely add comic book/strip/cartoon writing to my range of services!

How silly of me, how could I not think about this before? 🙁

2017 Update: definitely working more on this! Aiming at growing the art business in 2017 alongside the writing.

23. Find more trade magazines and niche blogs to pitch

I like trades more than glossy or consumer mags/blogs and TradePub is my daily (or weekly) joy. So I think I found a match, here.

2017 Update: it was probably too early for this in 2014 and I gave up very soon. Doing it again for my going-32, working on mastering the LOIs craft!

24. Re-pitch rejected ideas

Often I just post them on my blog, but I should re-pitch them instead, to other blogs and publications.

I’m learning to love rejections and use them to find new (and better) opportunities, but sometimes my emotions betray me.

That’s an area I need to work on.

2017 Update: oh, I think I mastered this one by now. Check!

25. Get some niche clips from guest blogging

For niches I want to experiment with. I think this is the easiest way to break in and get a clip.

2017 Update: This one needs more work, so I’m having it as a going-32 challenge as well.

26. Remember to enjoy the writing craft while I’m at it…

… and forget the money.

Yep! Money is a big distraction and it usually leads me to produce lower quality work, so I better forget what people around me say (“Do it for the money!”) and enjoy the craft instead.

Money comes as a consequence. 😉

2017 Update: Check!

27. There’s freelance fiction, too

I should get back to writing short stories in my spare time, and try to get them published in literary magazines and newsletters, like Daily Science Fiction.

2017 Update: I haven’t tried any literary magazines yet, but I’m definitely going to self-publish as soon as both writing and artwork are ready.

28. Raise my rates– not BUTs!

Pretty self-explanatory, right?

2017 Update: I did it! As one of my toughest freelance writing challenges, I’m quite proud to have grown out of the low-pay range. I charge pro rates now – and they might go up again as I grow as a professional and my writing becomes a stronger asset for companies.

29. Come up with another freelance writing challenge for [year]

Just because. 😉

Of course, there will be a follow up post to this challenge.

What freelance writing challenges are you taking up this year?

Photo Credit: prettyinprint (cc)

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