Your Month-by-Month Guide to Starting a Successful Freelance Blogging Business

Are you thinking of starting your own freelance blogging business?

I was in your shoes less than 6 months ago, weighing the benefits of keeping my sales job with the potential gains of quitting and doing my own thing, in an area I was more passionate about.

It’s not easy to take the jump if it means saying goodbye to something with great benefits and stability — especially if you have a mortgage, kids, and other dependencies.

Starting a successful freelance blogging business is not something that should be done with haste. 

Instead, take some time to plan your course of action before taking the leap for a better chance at success and a lower amount of stress. Use this month-by-month guide to properly prepare yourself for what’s to come. 

3 months before quitting your job

You may choose to start thinking and acting towards starting a successful freelance blogging business many months before you quit, but it’s important to start taking action towards making it happen at least 3 months before quitting your job.

It’s at this point that you should start making an effort to fill the gap between what knowledge you currently have of both freelancing and blogging as separate topics, and what you still need to learn.

One of the quickest ways to fill this gap is to learn from someone who’s already successfully navigated the path, and there are no shortage of resources when it comes to online courses geared at prospective freelance bloggers.

Sophie Lizard has her own course for freelance blogging beginners that you can find here. Or Gina Horkey and Elna Cain are two other freelance bloggers who have found success and are willing to share their secrets with you!

Keep in mind that starting your own freelance blogging business is more than just writing a lot of content — it’s also about prospecting for new clients, account management for current clients, accounting, networking, and so much more.

When you work for yourself, you have to handle all the various elements of business yourself. Once you make enough money, you can outsource many of these tasks, but most beginning freelance bloggers won’t initially make enough money to justify that.

It’s not easy! And if you’re not willing to put in the work, I suggest you stop reading here.

If you’re ready to push through, then let’s continue.

2 months before quitting your job

After you’ve learned the basics of freelancing and blogging (both as separate entities and together), it’s time to put what you’ve learned into practice. Start creating some writing samples!

A personal blog is an ideal place to learn about blogging and business, and for testing a concept. Done well, it can even serve as a sample if you haven’t yet been published on other blogs.

While you’re practicing what you’ve learned, it’s also important to start familiarizing yourself with different places to find work so you’re not floundering when it comes to drumming up business when you quit your full-time job.

There are so many different potential places to find work, but here are some that have served me well in my first months of starting a successful freelance blogging business:

• Fiverr (just make sure you structure your gigs strategically)
• Your existing network
• Other freelancers with complementary service offerings, like a website design company
• Freelance blogging job boards
• Local businesses

Websites like Upwork and PeoplePerHour are hard to recommend, because they force you to compete with other freelancers on offering ridiculously low prices — consideration is not often placed on quality. If you’re just getting started, however, they could still be a good place to learn about pitching and to get some experience and samples.

Speaking of pitching, that’s another critical element of starting a successful freelance blogging business, as it is often the difference between consideration for a freelance blogging job or being completely ignored.

High-quality writing samples published on high authority blogs will get the experienced freelance blogger far, but new freelance bloggers will have to try a little harder and be more crafty in their pitch.

Ultimately, a potential client wants to know, “What’s in it for me?” What do you have to offer them that makes you a great candidate? Keep that in mind while creating compelling copy to convince them to hire you for the job.

1 month before quitting your job

If you’re a month out from quitting your job, it’s time to get really serious if you haven’t already. Start actively applying for jobs on the various mediums you’re targeting.

As the time from application to consideration, onboarding, and finally submitting your first client post (and getting paid!) can span from days to weeks, you’ll want to start this process before you quit to ideally line up some work for when you’re freelancing full-time.

This is also a great time for learning. Try different approaches in your pitch and see what’s getting the most responses.

If you have any published writing, it’s also an ideal time to start working on your writing portfolio website. I recommend WordPress, as it’s fairly simple to use and extremely customizable, but non-technical writers may appreciate the extra simplicity of portfolio platforms like Contently and Behance.

Portfolio websites make it easy for potential clients to learn more about you, your style of writing, and the industries you specialize in. Make sure that you also take a look at social networks where clients may find you — do they represent you as being a competent freelance blogger? If not, it’s time to think more strategically.

Quitting your job

Actually quitting your job is perhaps the scariest moment of the freelancing process. Not only are you saying goodbye to a sure thing, but also the people who comprise your daily life.

Make sure to give your current employer at least 2 weeks’ notice before your last day, but be prepared for the fact that they may not want or need you to stay the full 2 weeks. I was in a sales role when I quit my full-time job, and there just wasn’t much for me to do after I quit (and was no longer prospecting new business).

I ended up only giving 1 week of notice after seeing how other sales people transitioned to new jobs. Reach out to a trusted colleague who’s been there for a while for advice if you’re unsure how to go about quitting.

Use your last moments at your current job to end things on a good note. A couple of suggestions:

• Get some LinkedIn recommendations from your boss and coworkers
• Assemble all the information they’ll need to complete your current projects
• Quantify all the great things you did while you were there

Finally, no matter how disappointed you think your boss or coworkers will be to see you go, don’t let anyone else’s emotions affect your decision to leave. Following your passion is rarely easy — but it is worth it!

1 month into full-time freelancing

Ideally, your first month of full-time freelancing involves pitching for work 90% of the time.

If you land a dizzying amount of clients, congratulations — you’re better off than most new full-time freelancers.

And if not? Don’t sweat it. This month is about working hard to build up your roster more so that, eventually, you spend an increasing amount of time completing client work instead of seeking it.

Even if you do have a full roster of work, that’s no excuse to stop looking for new clients. One of the most important things to learn about freelancing (and life) is that you should never count on working for anyone forever.

Things can change at the drop of a hat for reasons that may have nothing to do with you. Don’t be a victim — be resilient. Think ABC: “Always Be Closing” deals for new business.

Besides pitching for paid client work, now is also a great time to try to secure some guest posting gigs (like on this blog!). You can take a few different approaches:

• Guest post on blogs on a topic you’re passionate about, to get general writing samples
• Guest post on blogs in an industry you’re interested in writing about, to create writing samples that convey expertise
• Guest post on blogs that clients looking for freelance bloggers read, to drive them back to your portfolio website

Regardless of what approach you take, guest blogging will help you perfect your pitch and create writing samples in what’s usually a lower-risk, higher reward environment than going directly for paid client work.

2 months into full-time freelancing

By the second month of starting a successful freelance blogging business, you should be starting to get the hang of things. This month is really about learning from how far you’ve come and refining your processes for the future.

Start thinking about productivity and efficient use of your time. Starting a successful freelance blogging business is a time suck when you consider that you’re not just executing the writing work, but doing many sales and administrative tasks (to name a few of the roles you’ll be taking on).

Here are a few processes you’ll want to create:

• A list of prospects and clients and where you are in the sales process with them. Include client name, contact information, where the conversation last left off and when that was. This will help you to determine appropriate follow-up times in an organized fashion.
• Client projects, relevant details and due dates. You could create a spreadsheet, use a task management app like Asana, or a to do list app like Todoist (or a combination of multiple software solutions, if you like). Some clients, especially those with an established editorial department, may want you to use their system. Just make sure you create your own, too!
• Templates for proposals, contracts, and emails you frequently send out. There’s no sense in re-writing these for every client.

In general, think about the tasks you do over and over again and think about ways to standardize or automate them. I waited til more like 5 months into starting a freelance blogging business to give this the attention it deserved, but I wish I’d started sooner!

3 months into full-time freelancing

3 months into full-time freelancing is a major milestone. I’m willing to bet there have been some tears, a lot of sweat, and maybe even blood from a paper cut or two.

Starting a successful freelance blogging business is not easy, and it’s not for everyone. At this point, take a critical look at how far you’ve come and if you’re still excited to continue the journey.

If you’re still excited to get up every day and pour yourself into the hustle, then I have all the faith in the world that you will find success. If you’re anxious and nervous — that’ s OK! I’d think you were crazy if you weren’t.

Here’s a little secret: I’m 6 months into freelancing full-time (with years of freelancing as a side-hustle before that) and I still get imposter syndrome almost every day. Ultimately, you can own your feelings or let them own you, and I choose the former.

So take a critical look at what’s working and what’s not. Maybe you’re trying to write for an industry and it’s just not a fit — but you could be the best writer in something else you’re passionate about or knowledgeable in.

The next important thing to ponder is your long-term plan for growth. Are you going to continue with freelance blogging or are you willing to consider additional services or revenue streams?

It’s not necessary to add them in at this point, but it is beneficial to start thinking about how to position yourself accordingly on your portfolio website and with clients, not to mention how to fill any current knowledge gaps!

Congratulations on reading this post and taking the first steps towards building a successful freelance blogging business. By now, you may have some questions and I’m more than happy to answer them! Tell me about what’s on your mind in the comments below.