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Why You Should Start Pitching for Freelance Writing Jobs Even if You Don’t Feel Ready

If you have been thinking about becoming a freelancer and quitting your job or doing freelance writing as a side gig, I wanted to give an update on my progress toward becoming a full-time freelance writer and blogger. Did I feel ready to start pitching for jobs on job boards? Hell to the no! But I want to encourage you to get out there and start pitching once you have a few strong writing samples because you will get a feel for what is out there and you might even get a gig right away.

That was what happened to me the first week I started seriously applying for writing gigs using legitimate job boards. (Don’t settle for content mills because they will only wear you down.)

This article covers my transition from working a job full time to blogging and making enough money freelancing to start cutting back my hours at my job.

I cover

  • How I find well-paying freelance writing gigs
  • Portfolio sites I use
  • Courses I used to start my transition to a freelance career
  • My means goals and end goals
  • Why I am doing all of this anyway

It’s a bit long… but you can skip around and hopefully get inspiration for your own journey.

Changing focus from affiliate blogging to freelance writing

A couple of months ago I turned my focus from working on my affiliate holistic health site to get started with freelance writing.

After only one week of pitching, I picked up an ongoing gig doing product reviews for a company that has 2 large, successful niche affiliate blogs.

The pay is around 240-to 300 per article depending upon the length, not all that impressive, but not bad for my first freelance writing gig.

It was surprisingly easy to get my first well-paying freelance writing gig!

It wasn’t hard to get a steady well-paying freelance writing gig. I found the job listing on the Pro Blogger job board I think, or it might have been one of the other job boards recommended by Elna Cain and Jordan Roper and it was only my first week of pitching.

The job boards I use for finding legitimate freelance writing jobs

Online portfolio sites I use

If you want to become a freelance writer or designer or offer any kind of freelance service, you will need to show off your skills somehow. That can be done easily by using WordPress, Wix, Squarespace or Weebly to build a site or using one of the many free portfolio websites that have beautiful, logical layouts for posting your work.

I have my own freelance WordPress site at mindbodycopy.com. I also have my writing portfolio posted at a couple of professional freelance sites that are free:

  • LinkedIn Pro: I like it because of the linked in learning course library is extensive and it is a great place to network with other freelancers.
  • NDash sometimes has good leads depending on your niche
  • Clear Voice: a nice place to organize your work
  • CloudPeeps I have not heard a peep out of CloudPeeps since I put up my links last month.

Trustworthy courses on starting an online business

  • Elna Cain Profitable Creative: she has lots of actionable practical advice on freelancing on her site. I highly recommend her blog and courses.
  • B-school and the Copy Cure: Marie Forleo is such an inspiration. Her site and courses are crammed full of paradigm-shifting ideas to shake you out of your comfort zone and get you moving. Tons of free information and video and ideas.
  • Jordan Roper: Fuck Yeah freelance Blog Writing course. Jordan Roper is a favorite of mine, she has a potty mouth and tons of practical information on how to escape your job and become financially freer through freelancing.
  • Limitless: Vishen Lakhiani’s Mind Valley course is expensive but every now and then he gives a 700-dollar discount. This time I pounced. The ideas may seem a bit airy-fairy at first and I was skeptical but I really want to change myself completely, so I decided to dive in no matter how silly I feel at times doing all the airy-fairy exercises. Mind Valley is an incredible resource for transforming yourself so you can really do what you want to do in life instead of being stuck in the same old rut. There are lots of free resources deconditioning the mind, even if you don’t want to buy the premium courses. Vishen is an inspiration having come from an extremely limited background to become one of the most influential entrepreneurs on the planet.

I’m nibbling away at these courses bit by bit using, what I can as I go along, diving back in and going deeper as I find the time.

There is no law that you have to complete a course from start to finish the first week you get it. I know I probably need to rely on myself more and stop taking so many courses. But I see courses as an investment that you need to do from time to time for life.

It is often said that you are the average of the 5 people you spend the most time with. Since I don’t have access to lots of successful people, millionaires, and geniuses, I try to soak myself in the closest thing I can get right now, the books, and online course versions of those people and the Facebook groups that go with them

Say NO to content mills

I know some people have found great clients and learned a lot about how to freelance using the content mills, but I have not even put up any profiles on those sites. I have heard a lot of negative things about how it feels to make a race to the bottom just to compete for clients on those sites.

I have stayed away from Upwork, Fiverr and the other low paying platforms Jordan Roper warns against. Instead, I have focused on sending out one or two pitches per day to legitimate job board listings for freelance writers. I have gotten lots of rejections, but I was expecting to pitch every day for a month or two and, tweaking my sample articles as I went along, before seeing results.

At first, I was only applying for work in my narrow niche of holistic health and plant-based nutrition. But I took Elna Cain’s advice and started applying for anything and everything that looked feasible just to start making some money and getting experience writing professionally.

How to apply to job board listings and land your first freelance gig

  • Write 4 or 5 great writing samples and post them online so you have clickable links.
  • Apply to every entry-level job or topic that you have background experience in
  • Follow the applications directions exactly
  • Check for responses often and be on the spot when a reply comes in
  • When you get a gig, be a self-starter and get the job finished on time or early.

For the company that hired me, (I’m a ghostwriter so I can’t reveal who it is) I followed the directions exactly the way they said to in the job listing, putting exactly the wording they wanted to see in the subject line of the email with exactly the number of words they wanted to see in the body of the email and the exact number of links to publishes articles on topics that where relevant.

Luckily, I had spent the last year writing articles for my own 3 sites mindbodyclarity.com, mindbodycopy.com and whatever doesn’t fit any of my niche sites goes on medium.com as well as a few articles for this more personal creativity site. I submitted the links along with a resume link and moved on to pitch to other companies listed on the job boards.

The guys that hired me got back to me within a couple of days and were surprisingly friendly. They said they were “impressed with my qualifications” and asked me to do a trial assignment at the rate of 12 cents per word for an 800-word article with a one-week deadline. I knew this was moderately low pay but I was so excited about the possibility of making a good impression that I spent a lot of time on the article.

It took the editor three weeks to get back to me with my next assignment because they were testing out 80 other writers! Wow! They admitted they had been really overextended. I was so excited that I had made the cut.

The workflow of freelance writing gigs

Every client does things differently, but the one thing they all seem to have in common is that they are busy and need self-starters who don’t badger them with endless questions. Be quick to learn the system, follow directions and make corrections quickly when prompted.

Often, you will never talk to the client by phone. This is especially true if you are working with a large, well-established company that has systems in place for working with freelance writers and designers. Email is getting to be the norm for corresponding with freelancers.

At most you may need to conduct an initial phone consultation to get an idea of what is needed for your client. If it is a small company or a single owner who has not set up a system, you may need to do a little hand-holding to get them into a workflow.

For my new gig, everything was done by email and then switched over to the Airtable platform to keep track of my assignments. I never even spoke with anyone on the phone.

I’m not sure how many writers they’ve kept on as regular contributors, but I was thrilled to be one of them. Since then they have given me one or two assignments per week and usually pay within a day or two of my submissions even before I have gone through the editing process.

Don’t be a needy freelancer

When you freelance you must learn to be a self-starter. There are several editors at the company I work with for two different sites in the same niche. Everything is done through the Airtable platform which is super easy to use.

I try to respond to messages promptly and don’t bug the editors with questions I can answer for myself. They have a writer’s guide with a lot of FAO’s so I turn to that first. They have been in a big overhaul of one of the sites for the last few weeks, so I don’t want to add to the workload by being needy.

Getting paid

A lot of times you are expected to invoice the client and they will pay within a few days. Or they may have a purchase order you need to fill out and they pay every 30 days.

With freelance clients for illustration and design, I have used quick books self-employed for sending invoices and have received payments through, PayPal, Venmo and Stripe. This job requested that I invoice them through PayPal at first, but they have streamlined the process so that they produce the invoice and pay me through PayPal once I submit the first draft of the article.

I have worked with companies before as a freelance designer and illustrator and this has been the easiest company to deal with. The fact that they pay weekly instead of on a 30-day schedule is refreshing.

Learning about affiliate marketing by writing for a successful blog

It’s important to just get going even if you don’t feel ready. I wish I had had the guts to start pitching using freelance job boards a year ago.

The assignments are not earth-shattering, and I don’t even have a byline because the posts are ghostwritten, but I love the gig because I am learning so much. I get to research new products every week. I write one or two articles per week. Sometimes I update and older article with new information.

I am learning a ton about structuring articles for affiliate marketing. The company I work for has created writer’s outlines for each type of post they do, on what to cover, how many words for each section, with suggested headlines and bullet points. They upload everything for us and supply most of the photographs.

How I got here from working full-time jobs that sucked

I first started looking into having an online remote business when I was teaching Pilates in Sebastopol CA. I had gotten myself another one of my amazing free living arrangement with a 98-year-old woman who needed someone around in the evenings.

I was burnt out on teaching Pilates and looking for something new

The Pilates studio politics were frustrating, and I had never really enjoyed teaching, so after 15 years of teaching, I finally quit and took up a seasonal no-pressure vacation rental cleaning job while I tried to market my art online and tried my hand at selling used books on Amazon FBA.

Using time wisely at my no-pressure cleaning gig

I cleaned by myself about 4 hours per day, but sometimes I cleaned with a crew if we had a big house to get done in the 4-hour window. I have always been entrepreneurial and have sold art at fairs, and made a living selling hand-painted T-shirts in the past as well as freelancing as an artist.

I was the only one on the vacation rental crew to listen to podcasts on my smartphone while working. I thought it was odd that people would spend 4 hours cleaning houses 7 days a week all summer, without doing any kind of educational listening. I would listen to Steve Chuo from My Wife Quit Her Job, Side Hustle, the Fizzle podcast, Pat Flynn, and anything and everything about how to start an online business and become a creative entrepreneur.

I sucked at Amazon FBA

Amazon FBA was really fun. I loved searching through thrift stores for books, toys, and games to send to the Amazon warehouses to sell, but I couldn’t get enough momentum to do more than break even. If I wanted to make money I would have to start buying a lot of new stuff online to drop ship and this didn’t appeal to me. I wanted to do something more personal and more creative.

Trying things until I found something that worked

I wasn’t having much luck selling art on Saatchi Art and other online markets though I had ideas I wanted to develop. I really wanted to find a way to earn more money while being location independent while developing my creative ideas.

I sucked at coding

Next, I decided to learn to code. It seemed logical and I heard you could make a great living at coding and hey, I live in California in the heart of Silicon Valley. I took courses on Skillcrush, which is a female-positive platform for learning tech skills. I found that I was not learning fast enough and didn’t have enough math background to get beyond CSS. Though I really like coding I was never great at it and it didn’t come easily for me.

I have always been a decent writer

I was already a decent writer and realized there might be something there that I could build on. At Skillcrush they suggested looking into other roles in the tech world if coding wasn’t your thing. There are so many creative positions that support the tech industry. So I reevaluated my skills.

I saw an ad for the AWAI “barefoot writers” course on my Gmail feed and clicked on it even though I never click on those ads. I have always liked writing and freelancing and had worked as an illustrator and designer in the past, way before everything went digital.

Searching for legitimate freelance writing courses

Something about the AWAI images of people in bikinis sunning on the beach while tapping away on their laptops looked fake, or too good to be true. I kept searching for freelance writing information and found Joran Roper’s site and Ed Gandia, another favorite of mine.

I have since joined a B2B (business to business writers) LinkedIn group to learn about B2B (business to business) writing with one of the teachers from AWAI, Gordon Graham, and will probably take his B2B course soon. AWAI is legit but it has really dated imagery and headlines on the site which threw me off at first.

The first course I took was Jordan Roper’s Cold Emailing Course, which is excellent for beginners and gives you a lot of direction and structure.

I began to think about a niche. I settled on holistic health since I have a background in teaching fitness and pilates and was a massage therapist for 20 years. I tried a couple of specialties before I ended up niching down to plant-based nutrition for my main focus with other related topics.

I sucked at affiliate marketing

I came across the Create and Go affiliate marketing courses while reading an eBook called Fast Track to Freelance by Amy Rigby, another great resource for beginning freelancers with lots of good ideas to get you started.

I decided that instead of freelancing, it would be more fun to write for myself and sell affiliate products on my own site using the Create and Go model of Pinterest marketing to get started.

I was worried about working with companies as a freelancer since I had experienced payment delays and other drama, as a freelance illustrator and designer in the past.

After working on my site ten hours a day and reworking my site and honing my writing skills a bit I began to be frustrated because I was not seeing a lot of results with affiliate marketing.

The Create and Go model wasn’t working for me though I had learned a lot about blogging from taking their blogging course. I had built up a nice Pinterest following by using their Pinterest course, but I still wasn’t seeing a lot of results with sales from my site.

I was enjoying writing and researching and building sites and designing graphics. Even though I was working on my business every spare moment it didn’t feel like work. And I loved learning about marketing.

But I was not bringing in enough money to quit my job and be location independent and have time to build my art projects, which is my dream.

It turned out that going directly into building my own platform, marketing affiliate products, and trying to come up with products and courses of my own was a long process.

I was spending money on hosting, tailwind, convert kit and courses so I wasn’t even breaking even. I really needed to start making some money.

Reevaluating my path…again!

I decided to spring for B-School even though I couldn’t really afford more course fees on top of my other expenses, and I had already bought a disgraceful number of courses over the past 6 years. I consider myself a course junky. But it’s better than heroin or crack.

I had been following Ash Aimbridge as well as Jordan Roper, Ed Gandia, Create and Go, Matt Giovanisci. Ash mentioned B-school in one of her entertaining potty-mouthed-yet-somehow-professional emails.

B-school was worth it because it made me see that I needed to offer a service and just get going with making money right away and then go back later and refine things as I went along. Marie Forleo is another awesome woman who is bushwacking a new path for us with tons of free resources on her site.

Jordan Roper also mentioned that freelancing was the easiest way to get started while you build your platform and become an expert in your niche. She wrote for tech blogs while she grew her niche as a writing expert.

I am not giving up on affiliate marketing and making money directly from my own sites and my own creations forever. I am still carving out time and working on those projects because I love doing it. But for now, my main focus is on becoming a high-earning freelance writer.

My free consult with Ash Aimbridge

Ash Aimbridge generously offered a free 45-minute consult to anyone who signed up for B-School using her affiliate link. She was wonderfully down to earth, funny, and sweet and really helped me to evaluate my freelance writing offerings and niche down.

After my consult with Ash, I spent a couple of weeks updating my sites, and moved the nutrition site back to SiteGround from Flywheel and audited the articles. I am still working on rewriting and refocusing my health site, so it works better. I began reworking my articles to include more research as a showcase for my expertise as a writer for freelancing.

I had spent a few months on the Fizzle.com monthly learning platform going through some of their business courses and had tried Flywheel for my health site because they were offering it as part of their monthly course package.

I found that Flywheel was too advanced and cumbersome for where I am right now. Siteground (my affiliate link) is easy to use and allows me to have multiple sites on one hosting platform. If my audience gets so big that I need to move to dedicated WordPress hosting I will deal with it then.

Around the same time as B-School, I found Elna Cain’s blog and course on making your first $1000 as a freelance writer. Cain encourages trying different niches when you are starting out and had a lot of good ideas on how to start getting work. As soon as I implemented her ideas for pitching, I got my first freelance gig and earned my first $1400 in a little over a month.

It isn’t in my exact “niche”, but the point is my confidence is up because I am learning on the job and getting paid.  This is giving me confidence and hope so I can continue to work toward my goals and continue pitching for more freelance writing jobs.

I haven’t quit my day job yet, but I can see the end of the tunnel

I am still working my air BNB job cleaning between 11- 3 seven days a week. But most days I only work 1 or 3 hours, except for a few days a month when I have to clean a larger house which can take 5-or 6-hours. So it is a pretty cushy gig.

I had a second housekeeping position that took up ten hours per week, but after a couple of months, of doing the ongoing freelance product reviews I had replaced that income and was able to quit the second cleaning gig.

I am living in Silicon Valley where rents are high. But I have been incredibly lucky. I have not had to pay rent in over 4 years because I have found alternative various situations. I have been able to stay in the vacant apartments at my BNB job for the past year and a half so I only end up couch-surfing once in a while.

A long line of RVs in Mountain View CA, where contractors live while they work in Silicon Valley

My three-year plan for earning and saving more money

I am learning to write white papers and do whitepaper layout and design using Gordon Graham’s book and linked in learning so that I can earn more per hour with B2B clients than you can with B2C (business to consumer) blogging.

Means goals and ends goals

Freelance writing for B2B is a means goal. I have other creative projects I want to complete but I know they may never be big earners or it may be a long time before they start bringing in money. I am working on a young adult novel and a line of art and figurines that I want to market just because those are my ends goals or creative passion projects.

But I learned from B-school that you don’t have to make money with everything you do and you don’t have to throw something out just because it isn’t profitable. Find things that are profitable that you enjoy that still give you the flexibility, funding, and time to do your passion projects.

My Skoolie short bus plan

I plan to get a “skoolie” short bus and convert it to veggie oil, gut it and put in a floor, bed, work area, and a kitchenette, like an RV, only way less expensive and a lot more durable.

If you have been thinking of going on the road as a location independent entrepreneur, Heath and Alyssa have an in-depth blog with lots of resources on how to get started with the RV lifestyle.

It turns out you can buy a used school bus for under $5000 at public auctions because schools get funding to upgrade their buses every few years. You still have to put in a few thousand to wire it for solar and build it out. But it still costs a lot less than an RV or a fancy stealth van build. (Everyone knows you are living in a stealth van anyway, because why else would there be a fan going and a roof vent anyway?)

Diesel is best because those engines last a long time and can be converted to biodiesel or run on veggie oil from fast-food restaurants. I plan on adding solar panels, and 2 or three types of redundant Wi-Fi so I can work from national parks and rural areas some of the time. In Silicon Valley, a lot of people live in RVs while they work in the area as contractors. There are a lot of public lands across the US where you can camp for free.

Government Agency Auctions

I am planning to visit permaculture and climate change sustainability projects around the US and write articles and post podcasts between my freelancing assignments. Eventually, I hope to find or build a sanctuary ecovillage or cohousing arrangement for creatives who want to live inexpensively, and sustainably with gardens and tiny houses.

Life balance can be a challenge

All in all, I am pretty happy with the process that is unfolding and with my progress over the last year or two. I am feeling a little isolated because of working so much on my own but I am enjoying life a lot.

I am a little out of balance because I have been so focused on building the business. I need to start getting out to meetups and start building more of a community. There are all kinds of great groups here, for toastmasters, entrepreneurs, hiking, dancing, etc.

I go to yoga class a few times a week and I just signed up to volunteer for a literacy program teaching reading skills. I live in a gorgeous area and get to go for long walks every morning in nature on local trails. I am on the waiting list for our community gardens at the local library.

Morning is my best time of day, so I plan to get 2 hours earlier from now on and work on my B2B samples while I am fresh and then work on more routine writing in the afternoons after my BNB job. It is great having my BNB gig even though I am on call 7 days a week because it gives me flexible work hours, a place to stay and enough money to survive on while I learn my craft and build my business.

Wrapping up

Going freelance can happen gradually or you can do it overnight or anything in between. There are so many different ways to do this and so many free resources out there to help you. I hope this helps you visualize how you are going to get where you want to go.

click for free crea tive  resource guide

Please share how your journey is going in the comments.

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I'm a digital and traditional artist at zoezuniga.com I write for mindbodyclarity.com and have a freelance health writing site mindbodycopy.com

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