So, you want to make money from home.

You want to be a freelance writer and blogger.

You see all the success that other awesome bloggers have and you envy their lifestyle.

I get it. I do too.

So, how do you get started? Most of the time, if you ask a successful blogger how you can become successful, like reaching their level of success, or how you can make money and quit your day job, they’ll tell you to

• Build a website
• Get Ads on your website
• Sign up for Affiliate marketing
• Network
• Cold Pitch
• Create a product, or the more complicated…
• Make freebies and then create a sales funnel (whaaa!? I know.)

But they’re leaving something out and it’s the absolute most important step to becoming a freelance writer or blogger. If you want to quit your day job and get paid to write, you need to gain confidence in your writing abilities.

Yeah. That’s literally, step one.

It’s a major change, going from someone who writes pretty emails at work or who updates the company newsletter, to interesting blogger or killer copywriter.

If you just start cold pitching, you’re going to second guess your samples, you’re going to re-read the email you already sent at least 5 times.

I know because I’ve done that.

You need other people to read your writing and either compliment you or pay you. Now the compliments are nice but they don’t do anything for your growing stack of bills, so skip sharing your latest post with your mom or your favorite cousin.

Go find a writing job that pays. When you get paid and finally feel that your work is worth something, you will be able to write your pitches with confidence.

You’ll be able to tell people you’re a writer.

Once you’ve done more than post on your blog, you’ll feel totally legit.

Aaand this is where it’s going to get controversial…

Most bloggers will not recommend this, in fact, some of the most well-respected bloggers will drill into you, via their freebies, their paid memberships or their email campaigns (those auto emails that pop up in your inbox every 2-3), that you should not do this.

But I’m telling you to do it.

Join Upwork. Yup. That marketplace with bidding and crap pay and even crappier assignments…Do it.

Image result for upwork

First, here are some bad thoughts on UpWork:

Why Freelance Writers Should Avoid UpWork at All Costs (+ Where to Find Work Instead)

5 Reasons Freelance Writers Should Avoid Content Mills and Bidding Sites [VIDEO]

But I don’t agree with them.

I joined UpWork and that’s where I

• Made enough money to purchase my domain
• Landed by biggest client
• Gained confidence in my writing
• Learned invaluable lessons (I talk about those in this post)
• Found my niche

UpWork does not work for everyone. If you’ve majored in journalism and written for established newspapers or magazines, you probably already have confidence.

So, skip this step and start cold pitching.

But if you’re like me; someone who was desperate to pave a different path, someone who saw people working 20 hours a week, making $5,000 a month, someone who needed to ditch the alarm clock and gain freedom of time and freedom of finances, then join UpWork.

Now, don’t misunderstand my message.

Do not remain on UpWork.

Once you’ve gotten a few assignments, your clock starts. If you’re still on UpWork after 3 months, you’re doing something wrong.

I’m not saying I never go on anymore. It’s fine to browse every so often. You can find some great clients or supplement your income in slow months but you will eventually have to follow the advice of those totally successful bloggers.

You will have to cold pitch.
You do need a website.
You should do affiliate marketing.

Now that we’ve gotten that ugly and controversial truth out of the way, how can you land a few gigs on UpWork and boost your confidence?

First, create a profile. Keep in mind,  if you’re not yet established and don’t have a premium designation, there won’t be many people looking at your profile so you don’t have to go nuts making a video or anything.

When you send pitches, they’ll read your cover letter and your samples and (hopefully) send you an offer.

This doesn’t mean you shouldn’t spiff up your profile though! For the first few months, I was bidding like crazy and eventually, people started coming to me with offers (which was nice because it saves you connects).

So, give yourself a great description. Talk about your skills; this doesn’t need to focus solely on writing. In my UpWork profile, I talked about my professional background and my education. I also mentioned that I was good at writing (because duh, I’m looking to get hired, for writing).

Then create some sample pieces. You will attach them to your UpWork profile but you’ll also use them to include in bids. Most clients will ask that you provide samples with your cover letter, these will be those samples so make them good.

If you don’t know what your niche is, it can be hard to figure out what to write.

My first pieces
1. Research article on the Peregrine Falcon
2. OpEd on the Cutest Quokkas
3. 10 Ways to Move On

So random and really not my best work. But guess what? I didn’t know at the time. I do now, and oh goodness, do I laugh at my pre-blogger self with embarrassment.

They weren’t amazing, but they helped me land jobs.

Here are some ideas to help you with your first samples:

What is your favorite local restaurant? Write an Op-ed about the food, the service and why it’s the best place to eat.

What’s your favorite product? Maybe your iPhone 7 or your Nikon D610 camera? Write a product description, the specs, the pros and cons, the value.

Do you have any advice? Write some # of ways to do something (be happier, more organized, master dating).

Write a couple articles and then edit, edit, edit. These pieces are going to people who will consider whether you should be paid to write or not. So, did I mention that you should make sure they are super-duper edited? Edit them.

Even after you’ve sent 10 pitches, go back and re-edit. Now don’t change the content so much that your article becomes watered down or piddled into 150 words, but make sure you don’t have any grammar mistakes or spelling errors.

Most writing software has spell check, which is great, but use Grammarly. It’s better.
I cannot say enough good things about Grammarly. Like truly, I don’t always speak good, so it catches me and makes suggestions.

I’ve even added a browser extension so it edits my cold pitch emails, posts on my blog, and InMail and messaging in LinkedIn. It’s fantastic. It’s free to download and I cannot say enough good things about it, so get it.

Last step, take some tests. UpWork offers free tests so you can showcase your skills. And don’t worry, if you flop, you can hide the results from view and then retake the test in 30 days.

Once you’ve landed a few paying jobs, you’ll start to recognize your worth. You’ll feel good. You’ll know you can be a paid writer.

It’s such a liberating feeling.

Then, get off UpWork and follow these steps

  • Create a website (You might want to start with managed, which is a lot easier than self-hosted so go with, if you do want self-hosted, go with SiteGround.)
  • Create an email address for your writing only (it makes organization much easier)
  • Create a PayPal Account for your writing only (we’ll talk more about this in another post)
  • Create social media profiles for your writing only (again, I’ll talk more about this).  Hopefully, you’re seeing a pattern. For writing only. That keeps your stuff organized and professional, it streamlines your image

Join FB Groups, these are my absolute favorites:

Writing Revolters
Blogger Insights
Freelance to Freedom Project
Cult of Copy
ProBlogger Community
Freelance B2B Writers
Pinterest Pals
Copywriting Training Wheels – for beginner and rookie copywriters

Being a part of a community of freelancers, in all stages of their careers, is so helpful.
I learned where to find jobs, how to stay organized and monitor deadlines, how to increase blog traffic, where to cold pitch and what to say. It’s a wealth of information.

I’m part of groups on FB, LinkedIn, and Pinterest.

I learned about Pinterest Group Boards and LinkedIn Groups, from my FB Groups. I’m telling you, these people are incredibly helpful.

It also really helps to keep good company, people may not always understand your vision. A freelance lifestyle is definitely not everyone’s cup of tea so your friends and family might think you’re crazy.

Being part of a network of people that not only encourage but live this lifestyle, helps to boost your confidence even more, (which again, is the absolute most important step to becoming a freelance writer or blogger).

And bonus, most groups have promo days where you can share your blog posts and further your exposure, super helpful!

So, bottom line, gain confidence before you do anything else. I did that by starting with UpWork and I recommend it 110%.


*This post contains affiliate links but I promise, I would never recommend a product I haven’t purchased myself.

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