How to Start a Freelance Writing Business — Your Questions Answered

Paul Maplesden
Nov 11, 2017 · 10 min read

It’s not as daunting as you think.

Business editing by Tara Foss.

I am a successful freelance writer who has been writing professionally for the last two to three years. This year, I will be invoicing around $100,000 to clients, and am delighted that writing is my full-time job. I want to help other freelance writers launch their business and find success.

I took part in an “Ask Me Anything” Q&A session and have categorized the most popular questions and answers here, in the hope it can provide some examples and context for other people wanting to grow their own freelance businesses. Although the Q&A focused on writing, many of the techniques and answers here can be used by freelancers in any field.

You can find further answers here.

How did you take the plunge to go freelance as a writer?

I went into the “why” of how I went freelance in another question, so I am happy to go into the “how” (the process) a little more. It went (sort of) like this:

  1. Decided I *really* needed to do something to earn good money!
  2. Looked at my experience and skillset and decided writing was a good option.
  3. Researched and analyzed the freelance market for writers, including topics, rates, freelance platforms, etc.
  4. Decided early on to not use the platforms — too much competition, low rates, and commission.
  5. Decided to focus on writing for businesses rather than individuals, due to budgets, etc.
  6. Created a freelance writing portfolio website and shared some pieces I had written previously through websites like HubPages.
  7. Used the same approach to business as I did for my wife’s freelance editing and proofreading work.
  8. Gathered together all the places that post jobs online, set up automation to get notified about new postings when they happen. I used the RSS feed to email setup in “If This Then That.” Since then, I have found another website (Listiller) that does an excellent job of gathering together all the new freelance writing job postings.
  9. Reviewed all the jobs I saw to see if I would be a good fit. I only applied for gigs where I thought I was very qualified and could add good value.
  10. Started my rates out relatively low (8c — 10c a word) and have raised them over time.
  11. Was successful in getting jobs from places like ProBlogger, Reddit’s “For Hire” and “Hire a Writer,” and various other places.
  12. Started to get work with marketing agencies.
  13. Continued to build my portfolio and expertise.
  14. The current mix of work is around 80% existing clients, 20% new clients.
  15. Try to keep clients happy by communicating well, being professional, and producing high-quality work.
  16. Profit!

What do you attribute most of your success to?

Excellent question. There’s a slightly glib answer and a slightly deeper one.

Glib answer first — I attribute my success to deciding to become a freelance writer. What I mean by that is that you’re *never* going to be successful if you don’t actually get out there and *start*. “Boldness has genius, power, and magic in it.” So, the thing is to not have excuses not to do it. Have a plan, make the step, just get out there and do it!

The slightly deeper answer is self-confidence. Having the confidence to market yourself, apply to gigs, speak to clients, and ask for money. Essentially, you are selling yourself as the product, and if you’re not confident in the product, why should a client be?

On a more practical level, I think it comes down to proving you’re *really* good in your narrow niche, that comes in several flavors:

  • Creating a laser-focused portfolio that shows exactly what you can do.
  • Applying for gigs that are completely in your skillset.
  • Selling yourself in the cover letter or application.
  • Convincing the client at interview that you understand exactly what you need to do.
  • Not applying for stuff you’re not good at.
  • Being professional and friendly — communicating, being flexible, and having a no-drama approach.

Do you regret not starting your career as a freelance writer sooner?

Absolutely! I was made redundant at the end of 2010 and spent five years trying to make bad ideas successful! It taught me a lot, and fortunately, I did help out and grow my wife’s business, but my own ideas were, frankly, terrible!

So, I do sometimes think “I wish I’d started this five years ago” but that’s followed up very quickly with “But I am glad I started when I did.”

There’s an old proverb that says “The best time to plant a tree was 100 years ago, the second best time is now.” That’s how I see the choice I made.

The message here is any career choice you want to make, do it now. have a plan, and make sure you have everything you need in place, but do it! The one thing we can never get more of is time, you may as well enjoy what you do!

What prompted you to start your own business?

I have actually started numerous businesses, but a fair number of them failed (who would have thought you can’t make a decent living from writing poetry, eh? I tried. You can’t!)

The business I had that succeeded was my wife’s freelance editing business, so transitioning into another freelancing field wasn’t a huge wrench. I already knew many of the business basics — client relationships, admin, accounting, financial management, marketing, etc.

My background in technology and communications meant that writing was a natural career move. I’m a big believer in developing skills you already have, rather than trying to learn something completely new at the same time as building a business. That way, you’re not trying to do twelve things at once (instead, you will only do nine!)

What is the most surprising thing you’ve discovered about freelancing?

Probably that people are willing to pay for my expertise! When you are in a full-time, employed position, you’re insulated from that. Your employer makes money and pays you. When you’re freelancing, there’s no buffer zone between those things. A client is saying “I trust this person enough to give them $250 in exchange for a blog article.”

Now, I realize that blog article is going to be more valuable to them than $250 (otherwise they wouldn’t pay me), but I still find it surprising that clients are willing to do that. It’s why it is so important to continue cultivating good relationships with everyone — customers, colleagues, clients, and peers.

What has been the biggest hurdle in your current career?

The hurdles have changed as time went by. Early on, it was finding work, now it is balancing the time I spend looking for work vs. the time I spend actually doing it. That pipeline can be tricky…

If I could change one thing though, it would have been to have started earlier. The rest you can make up as you go along (assuming you have at least a rudimentary plan).

Do you think anybody can be successful as a freelance writer?

No. For some people, it’s just not in their skill set. Some people are better at expressing themselves in the written word, others using design or art, others in code, others in music, others simply are not that creative, but they might make great leaders, or managers, or team members.

Don’t try to *force* yourself to be good at something if it doesn’t feel right. Freelancing is enough of a struggle without having to struggle with your craft as well! Now, people with latent talent can certainly bring it out through the right experience, exposure, and advice.

But, don’t be fooled into thinking “anyone” can be a freelance writer by doing a course or two. Being a successful freelancer in any field requires much more than just completing an online course on writing.

You have to be good at sales, analysis, marketing yourself, accounting, communications, having self-confidence, lots of stuff. That goes for all freelancing. Writing is not an entry-level job!

Do you think you’ll enjoy being a digital nomad at some point?

I was a digital nomadette (hey, I like that word!), in that I moved my entire life from the UK to the US just over three years ago. In terms of wanting a digital nomad lifestyle now, probably not.

I am lucky enough to live in one of the most beautiful places in the world, Asheville NC — mountains, good people, and good beer, and our lifestyle pretty much revolves around dogs. This all means I probably won’t be backpacking around the world anytime soon — no regrets, though!

I think freelancing *is* a great idea for those who do want the digital nomad lifestyle though — you can work from anywhere, and technology means we’re never more than a notification away.

Do you have tips for new or established freelance writers?

Key points I have learned:

  • Having a plan is vital — you can’t just “wing it” as a freelancer. Think about how you are going to present yourself, the areas you’re going to specialize in, how you’re going to market your services, etc.
  • If you can, get a financial buffer in place before making the leap. Getting established can take time, and you don’t want additional stress of not knowing if you’ll make the mortgage payment this month.
  • Always ensure you back everything up in writing — contracts, agreements, briefs, collaboration documents. It keeps everything clarified.
  • Get a productivity system in place so you can always meet your commitments. I use “Getting Things Done” and Todoist to manage all my projects. Trello is pretty great too,
  • Always, always, always be decent, honest, and transparent with clients. If you’ve made a mistake, own it, apologize, and solve it.
  • Don’t think of yourself as “just” a freelancer. You’re a business owner, and the services you provide are valuable. Treat what you do as a business.
  • Never be afraid to ask what you think you’re worth. I have almost doubled my rates since I started out.
  • If you can, have a project price, rather than an hourly price or a day rate. Clients prefer to work to fixed costs. Look into “value pricing” if you can.

What do you consider some of the best and worst freelance platforms?

The best freelance platform is the one that you build yourself:

  • Create a reputation as an expert.
  • Be courteous, friendly, and professional.
  • Always, always, always meet (or exceed) your commitments.
  • Create a kick-ass portfolio website.
  • Apply for stuff you’re really qualified to do.
  • Stand out by being a bit different in cover letters etc. Don’t be afraid to use humor and be slightly audacious.

How do you find job security as a freelance writer?

I’m not sure complete job security is possible. The process of writing and much other content creation is starting to become automated, so all freelancers and content creators have to adapt. Although I have a fair bit of work in the pipeline, there are always quiet periods!

The best thing I have found is to build up an “emergency budget” that can cover all your costs for a specific period of time. That really helps with peace of mind, and also the confidence to ask for a good rate. I also regularly spend time searching for new work — in fact, the balance of spending time doing (and charging for) work, vs. the time spent seeking new work is a tough one to manage.

In terms of an emergency budget, working out all of your costs and then putting aside three to six months worth of money does tremendous things to reduce your stress levels! It helps you get out fo the feast <> famine cycle that so many freelancers find themselves in.

Do you have tips for freelancers to save on their tax burden?

Oh yes!

  • Get an accountant who understands the ins and outs of freelancing.
  • Make the most of your retirement account — you can set up a 401(K) as a small business.
  • If you’re in the US and not on the ACA, and buy your own health insurance, that’s tax deductible.
  • If you’re an LLC (in the US) ask to be taxed as an S Corp, that way you can take some of your income as disbursements and save paying self-employment tax of 15% on some of your earnings (talk to an accountant).
  • Remember to claim your home office income, you can also claim a portion of your mortgage interest payments, property tax, insurance, etc.
  • You can also claim *some* utilities (in addition to the home office), we claim communications, broadband, cellphones, etc.
  • Don’t forget to claim for things like website hosting, software you use. etc.
  • You can also claim business meals (myself and my wife, my business partner) go out for a business meal once a month.
  • Don’t forget bank and PayPal charges, and things like currency exchange if you take money internationally.

I hope you find these answers useful.

I hope you enjoyed this article. If you did, please click the “Applause / Clap” icon to let me and others know. I’d also be delighted if you wanted to follow me, or follow this publication, “Trust Works” — all about working better.

I’m a professional freelance writer, creating content on business, finance, and technology. You can read more in my freelance writing portfolio.

Originally published at

Trust Works

The art and science of working more effectively, connecting with others, creating beautiful content, and building trust.

Paul Maplesden

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Freelance writer at, editor at and ethical vegan at

Trust Works

The art and science of working more effectively, connecting with others, creating beautiful content, and building trust.

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