How I Wised Up After 8 Years and Got My First Freelance Writing Contract

Freelance writer signs contractEight years is a long time to not know what you’re doing as a freelance writer.

But that’s exactly how long it took me to figure out how to get serious and treat my freelance career as a business.

I hope my story helps you figure it out a lot faster than that.


I’m a freelancer?

I did my first freelance writing in Seattle’s reality TV industry, when I was 23. During my interview with the production company, I was told the gig was temporary and would only last a few months.

It sounded great, so I accepted it — and the $13-an-hour salary that came with it.

But after talking with my coworkers, I found out I wasn’t a typical employee. In fact, I wasn’t an employee at all. I was a freelancer. And when they said the gig ended in March, they weren’t lying.

Over the next several years, I bounced around in gigs that lasted anywhere from three months to a year — with lapses of up to five months in between.

To survive, I took odd jobs doing everything from coaching soccer to selling cell phones. This hand-to-mouth cycle sucked, but seeing my name in the credits on TV made it seem worth it.

Not making a living doing what I love

Of course, reality (no pun intended!) eventually hit.

I was now 29, and had a six-week gig scripting TV. Talking with a fellow co-worker about money, I suddenly realized I made a higher hourly rate delivering pizzas than I did writing nationally broadcast TV.

That realization didn’t sit well with me, and I soon left.

I spent the next ten months in my hometown of Chicago, where my writing hit new lows. The only writing income I made was $25 from Fiverr.

Next, I decided to pack my bags and follow my girlfriend to Bangkok, Thailand. I took a job as an English teacher so I could survive while I figured things out.

The turning point

Last December, I read the book Eat That Frog by Brian Tracy. In the opening chapter, the author says the key to being successful at anything is to learn what other successful people are doing — and do the same.

This seemed obvious at first. But I realized that although I’d spent significant time developing my craft as a writer, I never cared to learn what successful freelancers were doing.

So I started learning. I joined the Freelance Writers Den. On my hour-long commute to my full-time job, I read blogs and e-books by Ed Gandia, Danny Iny, and others. And I set aside 5 hours a week in the evenings to learn.

One big realization is that I had to stop fearing failure. I’ve started looking at all my business experiments as practice. If I fail, then it’s not a big deal. It’s just practice, and I’ll get better as I go along if I keep going.

Taking action

Another thing I realized? My biggest challenge was marketing. It was scary, and I hated it. But if I was ever going to actually make a living writing, I needed to suck it up.

I started by asking family and friends for referrals. No dice.

I sent letters of introduction to hotels that had poorly translated English websites. But none of them could afford a writer, so that was a dead end.

After about six months, I began going to local networking events hosted by Meetup and the Chambers of Commerce in the embassies here in Bangkok. Once I took the advice of the freelancers I was following and started looking to make friends, not just find work, I started to really enjoy in-person networking.

That’s when I started making progress. I eventually found all three of my current clients through networking.

Finding clients

My first client came this past August. I used the lessons I learned — and the templates provided — in the Freelance Business Bootcamp offered within the Freelance Writers Den. It was the first time I ever created a freelance writing contract, negotiated the payment myself, and truly felt in control of my freelance destiny.

Eight years in, and I was finally acting like a real freelancer.

When I got three clients, I quit my full-time job. I have a great variety of work teaching writing to one client, writing video scripts for another, and writing content and web copy for a travel/backpacking site.

And even though some of the rates aren’t what I’d ask for now, I feel awesome that I negotiated them myself. My best rate — and my easiest client to work with — came when I entered the negotiation with a solid idea of what other people charged for that type of work and the knowledge that I could walk away if I didn’t get that rate. I’m actually prepping to re-negotiate one of my lower-paying clients, and I am ready to quit if they can’t meet my new rate.

Having a good problem

I’m drowning in work now, and I’ve turned down a few other clients already! I’m not sending out LOIs, but I am still attending networking events.

This whole “being swamped with clients” thing is kind of new to me. And it’s kind of scary.

So what am I doing? Same as before…learning how others handle juggling multiple clients, and doing the same myself.

When did you realize you were running a freelance business? Tell us in the comments below.

John Weiler is a Bangkok-based writer and editor specializing in video writing, with professional writing experience for networks incuding A&E and National Geographic.

Freelance Business Bootcamp

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46 comments on “How I Wised Up After 8 Years and Got My First Freelance Writing Contract
  1. Elke says:

    My initial problem in entering the field was not having enough work. It was more that I couldn’t keep up. The truth was that I wasn’t really up to it – though it took me a while to realise this. I couldn’t keep up with the workload and deadlines.

    My entry into freelance writing was purely by accident. I was writing fiction, and was offered some regular article work on the side.

    The publisher had other writers, and I assumed they must be experiencing the same problems as me. I was going to contact them and ask, then see if we could all ask for more time to write. The deadlines were killing me…

    First, I checked all their names out online, then realised that they had all been writing for many, many years. And had professional websites with long lists of referees.

    I decided to keep my mouth shut.

    After a couple of years slaving away, I managed to cut the time I took to write each article by about 50% or so – though I still missed a few deadlines. It was excruciating and I expected to be fired at any moment.

    It’s only in the last year or so that I have felt able to call myself a professional writer and to approach other publishers.

  2. Just joined! Thanks, Carol!
    Rachael Gingery recently posted…It Takes a Village…My Profile

  3. 95%!? That’s encouraging to hear!

    And I can’t wait to get into the Den. I was on a trip without my computer when you opened it up the other day. Patience is a virtue, they say.

    I’m confident I’ll be successful once I find my niche – that’s the hard part for me.
    Rachael Gingery recently posted…From OCD to Living in an RVMy Profile

  4. Carol, your blog and community are amazing! It’s so encouraging to hear stories from those who struggled to break into the freelance writing world but were ultimately successful.

    I know I’m supposed to write… I just haven’t figured out how I want to monetize my skills just yet. But thanks to your insight, what I DO know is that I would rather write pro bono than let a writing mill crush my spirit. You (and your guest writers) are so inspiring!

    As for me, I’m a 30yo full-time RVer who sold everything and escaped Indiana for the west coast.
    Rachael Gingery recently posted…Why I Decided That Less is MoreMy Profile

    • Carol Tice says:

      You know, with a half-dozen pro bono clips for real clients, you can go out and get real, paying gigs. It breaks my heart to hear about writers who slave on year after year for mills, thinking they’re getting valuable experience — but there’s little good-paying work out there in anonymous, SEO-keyword-stuffed quickie posts, and will be even less in future.

      I love my guest posters — we work hard to bring readers practical and inspiring stories of how writers are breaking in and moving up to earn more, right now, and I turn down probably 95% of what I’m pitched.

  5. John I liked your article because it sounds so real, and it is real I know. It teaches that once you cross the mountain, the other side awaits you with great awards. I have not still thrown myself fully into freelance writing and have been writing for about 6 years now for PPC sites. As you know, that’s not great money or satisfaction. I want to get away from the crowd and excel but haven’t been able to do so as of now. Your article has given me a shot in the arm. Let’s see…And congrats for a great article.

    • John Weiler says:

      Thanks, Rajesh!

      If you can get a few months worth of savings stockpiled, then I think it’s totally worth it to make the full-time jump into freelancing. Alternatively, try and get a few clients while still working your full time job and then make the jump. You can do it! It’s scary at first, but if you’re determined, you will make it.

      Also, one of the best things you can do is come up with a business plan. Not sure if you’re a den member, but there is a really good template in there that I have used. Regardless, have a strategy and practical plan. Then anything is possible.

  6. k. says:

    hi John; highly inspirational; would love to know how exactly, beyond negotiating your own contracts, you went from 3 clients to being swamped?

    • John Weiler says:

      Hi K,

      Actually the three clients are mainly responsible for the reason I was swamped.

      I wrote the first draft of this article back in October when things were crazy. I only had 4 days off that month at best. In addition to these three though, I did have two other small gigs on top of this. One which was completly non-writing that I had committed to when I was still teaching English at the school in Sepetember and then of course writing this blog post.

      In October, I also had two additional gigs that I turned down because of both lack of time and lack of interest.

      You asked “how” I got swamped with work though. And the answer is just very concentrated marketing. Spend more time marketing than writing (which is easy to do when you have one or zero clients). All my marketing efforts that I had done in August and September finally came through in a flood in October. In fact, at the beginning of that month, I landed two new clients and had two additional gig offers in my inbox, all in the same day. Was quite a shock for me.

      I should add, that my marketing efforts here were probably not the right way to do this. I’ve heard from way more experienced freelancers that you’re marketing should be consistent and steady, and in October I dropped my marketing completely…both November and this month have been quite slow for me.

      Besides a nice vacation, during this slow time I’ve again been doing intense concentrated marketing (sending out LOI’s, going to networking events, linkedin). And it’s starting to pick up again. I have three meetings with prospects this week and another the following Monday. I certainly need to find a better balance in my marketing, but I’m still learning. I’ll get there eventually.

      Hope this response helps answer your question.

      • Carol Tice says:

        Yeah, I think you’ve self-diagnosed there John — you want to do marketing in a sustainable way, rather than a burst and then nothing. That way you hopefully have a steady stream of prospects instead of the feast-or-famine cycle.

  7. Caleb says:

    Thanks for sharing this John! It’s a reminder that persistence does pay especially when you aim to become a freelance writer.
    Caleb recently posted…Our Best Season Is NowMy Profile

  8. Carol Boe says:

    John, Thank you for your great article and the advice of how to make contacts and enjoyably find potential writing gigs in Bangkok. I found your story and advice particularly interesting because I am an American living in Kayseri, Turkey. My day job is English Instructor at a local university. I have been trying to figure out how I can advance my freelance writing career in Turkey. Your article and website are inspirational. Like Thailand (which I visited while teaching in South Korea), Turkey is a cultural and business development goldmine. Thanks again!

  9. Thanks for sharing your journey. It gives me lots of hope and inspiration.☺

  10. Steph Weber says:

    “One big realization is that I had to stop fearing failure. I’ve started looking at all my business experiments as practice. If I fail, then it’s not a big deal. It’s just practice, and I’ll get better as I go along if I keep going.”

    ^^^This, John. 1000%.

    Once you kick down fear, it’s amazing what you find on the other side. Usually clients 🙂

  11. Sajib Mannan says:

    At first, I also thought that I would do a regular job but when I got introduced to freelancing my whole career plan changed. Then I got started with it and after three months I got my first job. It felt great. I helped my client with his E-book, wrote a few blog posts for him, wrote transcripts and wrote articles on health issues.

  12. I’ve been a freelance for several decades and made a living getting by with a couple of stable clients who hired me to write conference reports and newsletters.

    Then, the unthinkable happened.

    One of my clients stopped hiring writers to cover conference.

    Yikes! It had been so long since I looked for work that I had no idea what to do, where to look or what to even write about. Plus, the terminology of the freelance market changed during my blissfull years of work without marketing and I didn’t know what anything was called.

    While everyone was aggressively selling “content,” I was still peddling brochures, website features and newsletters.

    I didn’t know how to navigate social media and still thought I could get work by just picking up the phone and calling around. (I signed up for an online social media class but without a teacher breathing down my neck I never felt motivated to do the work).

    In other words, I was totally out of it.

    Everyone told me to network, network, network. I had to buy a couple of nice outfits (can’t network in sweats) and get out there to mingle with groups I previously made fun of because they seemed so stodgy and dated.

    Worn down with realization that I have to change my mindset or die, I started going to women in business networking events and found other like-minded people. I’ve since joined a few groups. Tomorrow, for instance, I’m going to a Chamber of Commerce workshop to learn to make 1-minute video promos.

    It’s all part of the “attending at least 4 networking events (workshops count) a month.”

    I think I’m coming around.

    After all, I just posted this comment.

    • Carol Tice says:

      Your story spotlights why one of the things we warn against in the Freelance Business Bootcamp e-book is getting too reliant on a single (or pair of) client. You shouldn’t ever stop marketing — because all freelance gigs end one day.

      You probably have a great portfolio, so it shouldn’t be too hard to put the word out and find new clients. In-person networking can be a great way to go about it — but be sure to aim for clients who’re big enough to have ongoing work.

    • John Weiler says:

      Thanks for the comment, Marcela. I used to make fun of network events too. At 22 in LA, everyone told me to network, network, network. I stuck my nose up at it with this kind of “I’m above that” artist attitude. I really hated the idea of going and trying to sell myself.

      But as I said in the post, once I got over that mindset, they’re actually really fun. And I’m rarely trying to sell myself. All I ever do is get to know others, knock back a few drinks, and just tell people what I do when they ask (And they always ask:)).

      Regardless of whether or not they need a writer, I always hand them a card before they leave. Never had an objection to that.

  13. Pete Boyle says:

    Great piece John,

    Exactly what I needed to read.

    I’ve been debating whether to get myself down to local networking events after the last one i went to didn’t go so well. After reading this i’ll be spending this evening seeing which one is best for me to attend!
    Pete Boyle recently posted…My Top Writing Pet PeevesMy Profile

    • John Weiler says:

      Good to hear, Pete. Carol has said it before…go out there and explore. You’ll find a networking event that works for you. Glad the post was helpful!

    • Carol Tice says:

      You have to keep circulating until you find the best networking event for you, Pete. I went to about 5 different types before finding one that was a good pool of leads for me — in my market, it turned out to be MediaBistro’s events.

  14. Liesa Malik says:

    Great article and topic, John. Thanks. My New Year’s Resolution? No more barter deals or “sure I can help you outs.” I will be successful–with practice.

    • John Weiler says:

      That’s the spirit Liesa! I used to teach snowboarding to beginners. And so many people want to give up at first. I always would tell them “everyone sucks in the beginning.” That’s why you don’t take your mistakes to seriously and keep going. That’s when you get better.

      Years ago I heard of a gold medal Olympic athlete talk about the secret to his success (don’t remember who it was unfortunately)…he said he looks at competition like practice. It takes the pressure off. And when you remove the pressure, you generally perform at your best and actually get better!

    • Carol Tice says:

      My rule is if you’ve got a half-dozen samples, you should be done with the trades and freebie things, Liesa. 😉 Time to market and find paying clients!

  15. John Weiler says:

    @Luke. You’re welcome, Luke! I started to realize networking was key when I read from more than 1 marketer that this is an easy way to start getting clients.

    As Carol has mentioned before, people are more likely to hire others that they know.

  16. Dave Burnham says:

    Thanks for sharing your inspirational story, John. Networking is something I need to work on at the moment and your story underlines its importance.

    • John Weiler says:


      Just get out there and do it. I found I’ve been getting better as I go along. I’ve been regularly attending different networking events since this past April and go anywhere from 1-10 times a month. You start to see what is working with potential clients and what isn’t.

      I just look at it as one giant experiment.

      • Carol Tice says:

        I was fascinated to hear there was good in-person networking to be had out where you live! Everyone should look around and not assume there isn’t any good networking. And if there really isn’t any — start a group!

        • John Weiler says:

          @Carol. Yeah, there’s a huge expat community and bustling networking scene full of people from all over the world. Of the three clients I mentioned…one is German, another British, and the third Thai.

  17. Erica says:

    Great post, John. And inspirational. My first foray into freelancing didn’t work for much the same reason: I didn’t treat it like a business.

    Best thing to remember is that yes, failure is often just practice. And that’s okay.

    Glad it worked out for you.
    Erica recently posted…10 crackerjack proofreading tips, and then someMy Profile

  18. Elna says:

    Thanks for telling us your journey! I’m finding that marketing is the key to getting your brand known, becoming credible and to growing your client list!
    I hope to be in the “being swamped with clients” boat soon!
    Elna recently posted…6 Foolproof Marketing Tips to Help You Become a Better Freelance WriterMy Profile

    • John Weiler says:


      It is! And seriously, all my marketing efforts I’d been doing for 3 or 4 months all decided to hit at the same time. There was one day in October I had 5-6 opportunities to take gigs. I turned down half of them out of overwhelm.

  19. Mateeka says:

    It’s great to hear from a new freelancer. Thanks for sharing your story!

  20. Luke Sprague says:


    Thank you for sharing your networking experiences with others. I know I appreciate it.


    • John Weiler says:

      @Luke. You’re welcome! I started realizing networking was key for newbie freelancers when I read from other successful marketers that this is an easy way to get started if you don’t have clients.

  21. Allen Taylor says:

    Some of us are slow learners. Glad to see you’ve finally made it. Keep plugging away. It keeps getting better.
    Allen Taylor recently posted…How To Start A Freelance Writing BusinessMy Profile

  22. Great article John! I felt the pain of the struggle and the relief, joy and growing confidence of success! Every freelancer has their own personal journey to success – some just take a bit longer than others to reach it! I’m glad it all came together for you in the end. 🙂

    • John Weiler says:

      Thanks, Deevra! My main problem was I never embraced the idea of freelancer. I always wanted to be an employee! But I’ve seen that many writers are expected to be freelancers. And if I’m going to be successful at this, I need to know what I’m doing. And learn from the best while I’m at it.

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