About Me, How to, Portfolio

Can You Be a Freelancer? Answer These 6 Questions to Find Out


Can you be a freelancer and work from home?

YES! You can!

You need three things.

  • The want to,
  • The how to,
  • And the guts to say “YES”!

It was 1994. I was rocking some sweet black and white Adidas and my favorite pair of earrings; one side was a denim jacket, and the other side was a pair of jeans. That’s what I was wearing when I had my first kiss.

Hey, it’s me. Do you like permed bangs? 

His name was Lance. He ran the dart booth. He had a cute smile I can’t remember a single thing we talked about. (Balloons? Darts? Criminal records? Where the rest of his teeth went?) I was a bra cup-size away from getting a free stuffed animal so I had to rely on my teenage wit and my one-strap overall. We kissed on the fairway during the middle of the day, when the crowds were the thinnest and he was taking a break from ballyhooing. Nailed it.

My very first kiss was with a carny. True story.

I had no idea what I was doing. I couldn’t really go around asking people how to kiss in 1994, and I did check my Encyclopedia Britannica! I was nothing if not thorough. But I had barely even practiced on my own arm/Luke Perry poster.

My first kiss was a lot like my first blog. Scary, nerve-wracking, necessary, and left me with a killer (okay, interesting) story to share.

Luckily for bloggers and freelancers of all flavors, there is an unending supply of information and resources in 2017.

That doesn’t mean it’s easy. Hell no, it’s hard. Just because you live next to a Home Depot doesn’t mean you can build your own house. Beginner freelancers and online writers still sometimes need some direction.



These are six of the most common questions that all beginner freelancers ask themselves. This should give you a broad overview of what it takes to leave your corporate job and leap into freelancing freedom. 

Does anyone want to hear what I have to say?

Are you an expert in your field? Can you talk about your interesting hobby for days on end and offer advice to others? Have you been working the same job for a few years and feel like you have some cool tips to share with your internet brethren? Then YES! Someone, right now, is googling all of the exact things that you know about, want to write about, and can’t wait to offer advice on.  


What do I write about?

Anything you want! It’s the internet! But seriously, here are a few things to consider.

  • What does your ideal internet presence look like? Think about this carefully, because this is your brand. Are you putting yourself out there as someone who is silly, quirky, and funny? Maybe your brand is being sassy and serious. Maybe it’s a bunch of these things all at once that make up who you are.

  • What do you never get tired of talking about? It’s great if you want to write tutorials on coding or braiding hair, but if you only have three or four really juicy things to share about it, where will you go from there? That is not meant to be discouraging. I want you to map out some direction for yourself so if and when you get sick of talking about healthy habits or fishing lures, you’ll still be able to churn out fresh content.

What do you do for a living now? Whatever it is, be the expert!

Feel like you’re not an expert on anything? I’ve coached some professionals as they made a transition to freelance work. Here are some of their professions:

  • Roofers
  • Customer service/call center associates
  • Makeup artists
  • Teachers
  • Parents

Here is a list of things I did before becoming a freelance writer:

  • Internet Tech Support
  • Office Administrator
  • Loan Officer
  • Human Resources
  • Training and Development Coordinator

Anyone can become a freelance writer if they have knowledge and advice to share. Your next step is to understand how to leverage those skills into an online writing career.

The makeup artist, for example, runs a how-to blog.

The roofer tells funny stories on his blog. He has been hired to write for numerous websites. His writing style is unique and his voice is clever. It doesn’t matter that he doesn’t have an MFA in creative writing. He found his niche and laid claim to his audience.

You need to have an audience. Why are you different? What do you offer that no one else is offering right now?


How do I actually make money?

That’s a really big and broad question. There are a lot of ways you can start making money right away. Websites like Flexjobs, Upwork, and Fiverr are all places where freelancers can begin looking for work immediately.

Freelance Writing Gigs is a website that posts new freelance writing jobs every day. Visit often.

Mediabistro will hook you up with companies searching for freelancers in a number of fields.

ProBlogger was my go-to website when I was just starting out as an online writer. New job postings are aggregated and refreshed daily.

Also, check out my review on Contena to see if a pay service is something that will help you get your start.


What if I’m not a very good writer but I have a lot of knowledge to share?

You have two options. Get better at writing or start a YouTube channel/Podcast instead. If you aren’t comfortable with either of these options, freelance writing is probably not your bag.

Whether you work for yourself or for someone else, writing from home demands that you are an above average writer. There are a lot of free programs that can help you improve the skills you’re lacking. Check out websites like Grammarly or Skillshare, or just start Googling and be amazed at the number of free lessons that are available to you.

You can also shoot me a message and ask how I can help you with your writing.


How much money will I make?

I have no idea, but the good news is that you can plan, budget, and set goals now, before jumping into a freelance career.

If you’re looking for a great starter budget spreadsheet, look no further than Google Docs.

Here’s a simple personal budget spreadsheet.

This is another basic budget planner.

If you hated both of those, try this one instead.

You can always go to Mint.com and start there, too. It’s free, easy, and I’ve been using it for years.

If you haven’t already quit your full-time job, wait. Make sure that you will be making enough money to pay the bills. Which leads me to…

How do I even start?

Check out Part 2 here where I give you a breakdown of your first steps, and tons of resources to help you on your way.

(And find out what happened with my Carny Kisser.)



Comment below and tell me how you began your freelance writing career. More questions? Read part two!


Do you need a mentor or coach to help you begin living your freelance dream? Do you need some help with the written word? Do you want to hire a freelance writer for your business? Do you want to talk about how many shows Gordon Ramsay actually stars in?

Email me at Chandi@ChandiGilbert.com or subscribe to my bi-monthly newsletter for quick and simple tips on how to improve your writing.



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