About Me, Being Authentic, How to, Portfolio

When I started my freelance writing business in 2016, I took notes every step of the way. I knew at some point, I would want to retrace my steps and share them with other beginners trying to become freelance writers.

This is not going to be a super long and detailed post. I have too many bullet points to do that.

This is literally every step I took from the very beginning when I was still working a 9-5 job.

The first thing I did was spend some time online perusing job boards like Flexjobs and Upwork. Everyone asks for your portfolio, sample works, URLs to published work. I had none!


Step 1. I gathered all of my creative stories and poems that I had. I began fine-tuning them to share with prospective clients. If you’re curious, this honestly never helped me land a gig, but it did help me get in an organized and creative mindset.

Step 2. I combed the web for ideas on what I needed to learn before applying to freelance writing gig postings. I also looked around for where job postings for freelance writers could be found. (Craigslist, ProBlogger, BloggingPro, Contena for a fee)

Step 3. I discovered that I would need my own website. At this point, I spent days buying a domain, figuring out hosting options, and beginning to learn WordPress operations.

Step 4. I offered my services for free in exchange for testimonials. I told everyone I knew to spread the news. Within a few weeks, I had gigs doing resume writing, writing an article for a hospital newsletter, some website copy, and some proofreading. I even helped an acquaintance write copy for her wedding planning brochure.

I really sucked. I had no idea what I was doing. But I did get most of them to give me the testimonials I needed.

Step 5. At this point, I knew I would need some help setting up my website. I also wanted someone to teach me WordPress intricacies. I paid someone from Upwork to help me get the basics set up.

I am still learning new WordPress processes to this day. I think all writers should at least know how to upload their own work into WordPress because many clients require their writing staff to do that.

Step 6. Then I got on Upwork to find my first gigs. I was still working full-time in an office, and I spent six or seven hours every evening in front of my laptop looking for clients.

I submitted hundreds of proposals in the first month. My first paid job was for $4 to proofread a memo.

Tip: You do not need to pay for extra credits to submit proposals on Upwork. You can submit to plenty of jobs with a free account.

UPDATED July 2019–Upwork has changed its pricing structure for both writers and for clients. Back in May, a big change took place. Freelancers are now charged anywhere from $0.15 and $0.90 to submit a job proposal, as opposed to being free.

If you’re curious about how this pricing structure works, here is a great guide to the Upwork Connects pricing changes.

To my surprise, my second client ever on Upwork is still an anchor client three years later. His work allowed me to eventually quit my 9-5 office job.

Step 7. I bought a lot of books I didn’t need. The only book I bought that I still use almost every day is a thesaurus; The Synonym Finder by J. I. Rodale. I bought a used paperback copy on Amazon for like five bucks, and it has never left my desk.

Step 8. I used my downtime to create a ton of mock-ups. I created fake wedding brochures, newsletters, articles, things I could add to my Upwork profile.

Step 9. I started understanding the importance of networking with other artists. Everyone always knew someone who was looking to have something written or created. Networking is one of the most important things I did, and still do, every day.

I have gotten nearly all my clients because of networking and forming relationships with other writers.

Step 10. Back to my website. Yes, this lovely website you are on now. It took me over three weeks to get my website together exactly how I wanted it. I repeatedly visited other freelance writers’ sites to figure out what I liked and what I didn’t. At the time it felt like my entire freelance writing business hinged on the launch of my website.

It cost me $$$, and I went through five designers before I got the perfect logo. In hindsight, my logo is the least important part of my business.

I love it, it reflects who I am, but no one has ever hired me based on the cool font my name is written in.

Step 11. During all of this, I was still constantly networking. I created a Facebook business page. I totally revamped my LinkedIn page. I joined Twitter.

I spent time on LinkedIn connecting with people and groups. I asked for recommendations from former co-workers. I spent time learning, listening, and asking.

Step 12. I enrolled at the University of Chicago to receive an official editing certificate. I use that information on my resume and in cover letters, but beyond that, it has literally never gotten me a job.

If you’re wondering if you need a degree or certification to get freelance writing work, you don’t. Clients will hire you based on the work you can show them. This is not accounting for certificates that promote SEO skills and things like that, however.

Step 13. I had been working towards building a freelance clientele for about a month, and I was still working my 9-5. I installed a landline and had fun creating business cards. I also bought a super professional headset.

Looking back, it was more exciting to plan than to actually do. I bought fun things, created logos, and business cards. It gave me the illusion of working towards my goals, but the reality was that I should have used that time and money to actually search for work.

I never once used my landline or headset, and I think I handed out ONE business card ever.

Step 14(ish). I don’t want you to think I am discouraging you from reading helpful books or taking worthwhile I read everything I could find on building a good portfolio, cold calling, cold emailing, pitching, etc. But there was no need for me to spend thousands of dollars trying to prepare myself to become a freelance writer.

All the preparation you need is in practice. I always say that talent and passion cannot do what practice can do.

Step 15. I did sign up for a free trial of Profinder on LinkedIn. I found one small client on there for a one-off job. Then I forgot to cancel my membership before the trial was up and they ended up charging my card $99 for about six months before I caught it. They do not refund money.

I tried finding local businesses who might need copywriting services, but I live in a small town, in a rural area. I decided to turn my attention to the internet only. It was a good

Step 16. I used Medium to publish some sample work, and I even posted my samples on my LinkedIn profile. (In upcoming blog posts, I will share a list of places to publish your work.)

Step 17. I used a Contena coach to help me fine-tune my pitch and create appropriate samples for potential clients.

This was when everything finally started to click. I started getting responses from potential clients. At this point, I had no bylines and nothing I could show except for my Medium article/s and samples I created.

It was enough for most clients, and I finally got my first byline after about five months of starting the whole process.

I always say that talent and passion cannot do what practice can do.

Final thoughts/things I wish I knew then:

I wish I wouldn’t have spent so much time, energy, and money on things that don’t really matter. Those things were business cards, a landline, my logo, books about writing, and more.

Spend your time on networking and perfecting your pitch. If you really want to spend money on something, look into SEO classes, or learning about WordPress.

I hope my timeline helps you figure out what comes next for you. Are you stuck on something? Let me know in the comments.

How to, Portfolio

Specific Steps to Finding Your Niche as a Freelance Writer

Let’s get straight to it. There are two things you can focus on while trying to find your niche.

  1. Your profession

  2. Your passion

Working at Honda, I became friends with many Japanese men and women. They taught me all about Ikigai. It’s a bit more complex than two circles with Passion+Profession=Dream Job.

What are you good at?

Before we even dig into your career, what is something you are just really good at? It doesn’t mean you like it, love it, or want to write about it. It is something you want to take into consideration though.

I am really good at public speaking and leading large groups of people. Do I love it? Nope.

But I can write about it!

Ask yourself what you’re really good at. Make a list. Be general, be specific, be both!

Here are some ideas.

  • Baking

  • Scheduling appointments

  • Changing a diaper

  • Singing

  • Making coffee

  • Data entry

  • Coloring hair

  • Creating spreadsheets and macros

  • Predicting the winner of MasterChef

This is simply a way to get your brain thinking about how awesome you are. Start your own list. You may not like doing the things on your list, but you can write about them!

Your Profession

Or let’s just call it your experience. Before I became a freelance writer, I didn’t feel like I had a “profession.” In fact, this is the first time in my life that I can confidently say “I am a writer. This is my career.”

Look at your resume. What does it say about you? Are you an expert in writing classroom lessons for elementary-aged children? Maybe you know everything about public speaking. Whatever your expertise is, your resume should reflect that.

If your resume has a lot of different jobs, that’s okay too. Before I became a freelance writer, I was:

  • A waitress

  • A cosmetologist

  • Tech support

  • Receptionist

  • Office manager

  • Loan officer

  • Human Resources something-or-other

  • Training and Development Coordinator

So don’t fret.

What did all of those things have in common?


When people would ask me what my career was, I didn’t know how to answer it. Not until I was 35 freaking years old. But I was good at communicating which was an important part of my job in each one of those professions.

What is the underlying connection on your resume? Maybe your expertise is actually finding new career paths or writing killer resumes. Or you’re an expert extrovert.

If it isn’t obvious at first, take some time to think about what your resume says about you.

Your Passion

This one is probably a little easier. What do you wish you could be paid for? I would joke and say too bad you can’t get paid to lay out in the sun on a tropical beach, but companies are hiring traveling writers every day!


If neither your passion nor your profession is the direction you want to go, be willing to learn new skills. Be willing to get feedback. Be prepared to invest time and energy in yourself.

If you want to write in-depth, well-researched blog posts about cruelty-free skincare products (there’s a niche for ya!) be willing to learn proper research methods. Seek out companies that are at the top of their game in the skincare blogosphere. What is working for them? Follow their lead.

Dig Deep

Maybe you don’t have a lot of time to devote to yourself or to commit to making a jump into freelance. Parents who work full-time probably understand this.

You think to yourself, It’s been ten damn years since I had time for a hobby, or I don’t even know what interests me anymore!

Listen, even TV binging is a hobby, so don’t freak out. Do you know how many companies are seeking entertainment recappers and reviewers?

Addicted to social media whenever you have a spare moment? If you know the ins and outs of Snapchat, Twitter, Insta, you’re already ready to write social media posts for money.

Do you spend your spare time budgeting your bank accounts on spreadsheets and researching the best apps or credit cards? THERE. ARE. CLIENTS. LOOKING. FOR. YOU.

You like writing Yelp reviews, or Amazon reviews, or talking about every book you read…all of these things count.

Now, I will give you one warning. Personally, I never believed anyone when they said this. I did find out for myself though.

When you hear, “Make a living doing what you love, and you’ll never work a day in your life,” please know that it is utter bullshit.

Anytime you monetize doing what you love, it can become tedious and stressful. Suddenly I have to write about how to split up finances during a divorce and the deadline and looming and why oh why can’t I focus?!

So, my warning is this: You may end up trading your passion for a paycheck.

You can avoid this by properly structuring your time and keeping some things separate. (I’m going to post a blog soon about how to schedule your days for maximum happiness.)

I may have veered a bit off topic, but let’s keep going.

Ask Yourself Why

  • Why do you want to be a freelance writer?

  • Who do you want to help with your freelance writing?

My want came from desperation to leave a job that was injuring my mental health and killing my spirit. Now, that’s obviously not something I would tell a potential client. However, it is part of my story, as you can see here and here.

But it created a motivation to find clients and put myself out there.  (That’s hard enough, amirite?) I wrote a bunch of sample articles on being a good customer service representative, and how to create lasting leadership in the workplace.

I realized I wanted to help ME and people just like me! I discovered that I love writing how-to blogs like this one, and like this.

As you create these lists on paper, or in your head, you should start to see a recurring theme. This should get you headed in the right direction.

Your Niche Must Be Relevant

Relevance is subjective, but what I mean is this. If you plan on pitching your writing to potential clients or publications, they probably don’t want a piece on Y2K. You have to keep up with trending topics.

However, if you’re looking for content writing, you’ll need to make sure you understand the basics of what most clients need right now. Understand what search engine optimization (SEO) is. Have a basic understanding of how driving traffic will help a business grow. Learn a little bit about WordPress. (Some clients want their writers to be able to upload their own articles onto their website. My next blog will focus on websites and WordPress.)

Go to Glassdoor or Indeed. Search for “writer” and take a look at qualifications and requirements. You’ll start to see a recurring theme there as well. It should give you some indication of the relevant knowledge and skills you’ll need moving forward.

You may get hired for a job that, at first, doesn’t seem to interest you. Perhaps you find that as you write more on the subject, and learn new things, you actually really do like it!

For example, my friend Amy was desperately seeking any freelance writing job that would pay her. She found a client who wanted her to write about toilet paper.

Oh, how we laughed!

But you know what? Three years later, she still writes for the same client, and she knows everything about toilet paper! She truly loves being a toilet paper guru! And now she is an expert in eco-friendly supply products, cleaning products, janitorial services, and more. She has so many high-paying clients now all because she took a job writing about toilet paper.

So if you are just jumping in head-first, you might find your niche without trying. If you can’t figure out where you belong, try everything!

Let’s Recap!

What am I really good at?




What do I know a shit-ton about?




What kinds of experience is on my resume?




What could I talk about all day long?




What are my hobbies?




Okay, so where is the crossover? Is there a theme coming forward?

I want you to comment and tell me if this was helpful. If it wasn’t, tell me exactly what you want to answer, and I’ll make the edits to this post and give you credit!



Maybe a niche isn’t for you. Maybe you are a generalist like me. Don’t let anyone tell you that it’s a bad idea. The people who are telling you that you must find a profitable niche are the people who are already making big bucks in their niche! Of course, it’s working for them!

Never compare yourself to any other writer. It’s poison. Do what works for you and fuck the rest.

How to, Portfolio

First Steps to Becoming a Freelance Writer

Do you feel it? I felt it!

It’s the freelance writing life, whispering your name.

I have tons of advice and info to share with you on getting out there and making it happen. With clients of my own, sometimes it’s hard to find time to sit down and reply to emails that don’t require my immediate attention.

But I want to let you know something important. Your emails this week, and last month mean the world to me. I read them all. Every single one warms my heart.

I see you. I hear you. I am here for you!

The very first thing I did when I decided I needed to leave my corporate desk job was TELL. EVERYONE.

I told everyone that I was attempting to make a jump into the world of freelance writing.

Tell people about your plan and ask them to share the news.

First, that’s what’s going to make it feel real. You’ve put it out into the world, and now you can’t take it back.

Next, you have to make it happen. The second thing I did was go through my Facebook friends list and ask anyone if they had any writing that I could do for them.

I offered to write or rewrite wedding brochures, website content, newspaper articles, anything at all that I could put in my portfolio.

I offered them my services for free on one condition: They had to leave me testimonials. I needed proof that my work was good!

This led me realizing I wanted a website of my own.

I am going to write another piece next week on how I built my own website with no experience, but for now, we’re going to skip ahead to your portfolio.

Your Portfolio

This is a collection of your work that you will use to showcase your skills. If you have no bylines* (and if you’re brand new to the industry, you probably don’t) you can create sample work.

When I started, I created a fake wedding brochure, an article about the customer service industry, and a pop-culture piece on Tyra Banks. I put these in my portfolio.

I would recommend you choose one lane and stick to it. I was all over the place in the beginning. 

*A byline is exactly what it sounds like: A BY line. By Chandi Gilbert. There’s my byline!


Finding a Niche Versus Being a Generalist

If you’ve been googling how to become a freelance writer with no experience, you have probably seen a dozen articles on the importance of finding your niche.

If you have a niche, that’s great! If you don’t, that’s great too!

Are you an expert in anything?

Many freelance writers have a niche or an area of expertise. Some writers call themselves generalists and are open to writing about many topics. There are pros and cons to both.

How to Find Your Niche as a Freelance Writer

Answer this: What subject do you know a lot about? Be very specific. (For example, I love jewelry, but I really love talking about how certain gemstones look on different types of metal.) You know more than the average person when it comes to THIS.

And now: What subject do you love to talk about? You could happily write about THIS and never get bored.

Your next step should be to visit websites that appeal to your niche. Find out what they are missing. For instance, you might find that a company doesn’t have a blog. This is where you make your move. You’ve successfully found a gap in the market.

If you find that your niche seems too specific, and you aren’t finding gaps in the market, it’s time to broaden your search. OR this could be the perfect opportunity to create your own market for your specific niche.

Your Expertise + Your Passion + Gaps in the Market = Your Niche



Being a Generalist Freelance Writer

This is who I am. A lot of people out there will tell you that you won’t succeed unless you have a niche.

That’s not true.

Many clients seek out generalist writers who are comfortable writing about any topic.

I have a long list of credentials and areas of expertise now that I’ve been a generalist writer for a while.

I can look at a job board and comfortably apply to five or six jobs in different areas because I am a generalist writer. I love learning new things all the time.

If you don’t enjoy researching new subjects, being a generalist writer is probably not for you.

Either way, there is plenty of work for both types of freelance writers.

Do I Need a Blog to Become a Freelance Writer?

No. But could it help? YES!

I get clients simply because they like my blog. 

If you decide to start a blog, focus your efforts on creating content that shows your writing style. There are a lot of clients that don’t care if you have nothing in your portfolio as long as they can see something you’ve written. Also, keeping an active blog shows that you work consistently on your craft.

What if I Don’t Know What to Write?

Ask yourself what your ideal workday looks like. If you like the idea of working virtually with others during set times (like Monday through Friday, 9 to 5), there are lots of clients who are looking for you.

Maybe you want to be able to take a break every hour, noodle around the house, only work from midnight to 3 am…there are plenty of clients who don’t care what you do or where you are as long as you get your work done.

There are lots of different types of writing for freelance writers.

  • Whitepapers
  • Press releases
  • Blogs
  • Social media posts
  • Ghostwriting
  • More!

(If you want me to explore all these types of writing jobs, send me an email or leave me a comment!)

Your Internet Presence

I’ve said it before: I have a love/hate relationship with social media. I just don’t get pleasure from those kinds of interactions. HOWEVER…as a freelance writer, you must have an internet presence, specifically on social media. Eight times out of ten a client will request that you include social media links in your resume or cover letter.

It’s time to take a serious look at your internet identity. For instance, if you want to be a serious, white-paper-writing professional, make sure your public persona reflects that.

My persona is really just me being me. That’s how I sell myself. My smile is my tagline. My whole brand focuses on being genuine.

Whatever you want to convey to potential clients, make sure your photos, bios, tweets, etc., reflect that.

The other significant reason I keep a social media presence is for networking opportunities. I have a wonderful network of friends in some of my Facebook groups. I’ve found a lot of work that way.

To wrap up this blog post, I will leave you with some links to my favorite job boards.




Craigslist in your local area

Upwork (Where I got my start and still find work)


My next post will go into whether or not you need a website as a freelance writer.

What else do you want to hear about? I want to hear all about it! (Ya’ll have been great about emailing me lately and telling me exactly what you want to know! I LOVE IT!)