Hello lovely people! I'm Paul, a successful freelance writer. I started writing full-time in January 2016 and will bill over $100,000 this year. I'd love to help you become a more successful freelancer (whether that's writing or something else) - Ask Me Anything!

Paul Maplesden
Jun 6, 2017

Freelancing is a great career choice for many people, but to be successful you have to approach it in the right way. I'd like to share my experience of starting and growing a freelance writing business, in the hope it helps others.

In my first year of full-time freelance writing (2016), I billed over $55,000. This year, I am on target to bill $100,000. I am happy to share details of my approach, background, how I work, and my tips and advice for anyone looking to break into freelancing or who wants to grow their freelance business. 

I am going to answer questions as thoroughly as I can to (hopefully) provide some insight and value for others looking to start or grow their freelance career. 

Please feel free to ask open-ended, difficult questions!

You can find out more about me at my freelance writing portfolio website.

If you want to write to me, I am at: paul.maplesden@gmail.com

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I'm a freelance writer on Upwork, but I haven't earned nearly as much. What's your secret? Joking, I mean, how you choose your clients, what are the topics you basically write about and where do you gain the info needed? How often and how much do you write? Also, do you work via a website such as Upwork, or you'd recommend something else? Thanks for the answer!

Jun 6, 5:22PM EDT0

Hey there, let's take your questions one by one.

I choose clients based on if I think I can offer them an excellent service - in other words, are they looking for writers with my particular skillset, experience, approach, and expertise? If they are, then I will apply to the gigs they advertise. If not, I don't. It means I don't apply to as much stuff, but when I do, I have a better chance of getting the role, and can request a higher price.

I write mainly about technology, business, finance, and related topics. In terms of getting the information, I already have a fairly good grounding in those areas (due to a previous career) and then I carry out research on the specific topics I have been asked to write about.

I write every day, and typically write around 2,000 - 4,000 words a day. 

I don't use any freelance platforms, I apply directly. I covered my approach in some detail in a few other answers in this AMA. Please have a read through and if you still have questions, let me know.

Last edited @ Jun 8, 12:36PM EDT.
Jun 6, 5:40PM EDT0

Thank you very much for answering all those questions!

Jun 7, 5:45PM EDT0

How do you get connected to freelance jobs? I've primarily used Upwork, and I've billed $5,000 in the past three months. But I'm struggling to build up my client list.

Jun 6, 1:13PM EDT0

I guess you could approach website owners?

Jun 6, 1:19PM EDT0

I apply to jobs I see advertised on places like ProBlogger. I have covered this in some detail in answers to other questions, so please have a read through. If you'd like further information, I am happy to provide it.

Jun 6, 1:23PM EDT0

Do you enjoy your work or do you just do it for money?

Jun 6, 1:01PM EDT0

I *love* my job! I get to research fascinating topics, work with awesome people, and take pride in doing what I do every day. I've never been a natural leader myself, but I love doing stuff that makes others successful. My work gives me a great sense of fulfillment and purpose. Of course, the money doesn't hurt!

I think it you're a freelancer though, there are lots of reasons to do it besides the money (since you can likely earn a good living using the same skills in someone else's business.) 

Other good reasons for being a  freelancer?

  • Freedom to work on what you want, when you want.
  • The ability to set your own schedule.
  • Puppers!
  • Knowing that everything you accomplish is down to your own skills, experience, and approach.
  • Having a great relationship with clients.
  • Being able to say "no" to work you don't want to do.
  • Puppers!
Jun 6, 1:11PM EDT0

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

Jun 6, 1:00PM EDT0

Excellent question...

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.

Jun 6, 1:15PM EDT74
Show all 4 replies

Hi Paul,

Are you active on any freelance platform, such as UpWork? If not, how do you go about finding your clients? Cold pitching?

Jun 6, 12:56PM EDT0

Hey there. I don't use any freelance platforms at all. A number of my peers have called out bad experiences, high commissions, and lots of competition, especially on Upwork.

My method of finding work is to apply to advertised freelance roles on places like ProBlogger and other job boards. I have automated notifications, Google Alerts, email subscriptions, etc. The secret to successful pitching to these gigs is:

  • Super relevant experience and expertise.
  • Perfect supporting writing samples.
  • A kick-ass cover letter.
  • A professional and friendly approach.
  • Being able to do something in addition to "just" being a content creator.
Jun 6, 1:08PM EDT1

What prompted you to start your own business?


What has been the biggest hurdle in your current career?

Jun 6, 12:54PM EDT0

Hey Scott, fancy seeing you here! 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!)

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).

Jun 6, 1:04PM EDT0

Do you think you'll enjoy being a digital nomad at some point? After all, freelancing allows you to live that kind of lifestyle ..

Jun 6, 12:26PM EDT0

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. 

Last edited @ Jun 6, 1:27PM EDT.
Jun 6, 12:59PM EDT156
Show all 3 replies

What do you think of fan fiction writing?

Jun 6, 11:48AM EDT0

I think it's a good way for people to express their creativity, so ultimately it serves a good purpose, and it may be the stepping-stone people need before they move into other writing. Like anything else, if it helps you learn your craft, I am all for it.

Last edited @ Jun 6, 11:58AM EDT.
Jun 6, 11:55AM EDT0

Looking forward to this AMA to start, what a great subject, should be shared everywhere. My question, I decided to get started, what am I doing for the first 10 days, 30 days, 90 days? Thanks in advance!!!

Jun 6, 10:27AM EDT0

This is an excellent, challenging question. Here are my thoughts...

First ten days

  1. Find the niches you want to write about - start with two or three. 
  2. Base your niches on your interests / passions, past work or academic experience, and areas where you feel you have a unique insight.
  3. If you don't already have samples of work, write on places like Medium, HubPages, and the like on the subjects you love. Come up with an interesting subject / point of view, and expand on it.
  4. You can start with just half a dozen portfolio pieces.
  5. Use good principles of online writing - short paras, good formatting, headings, logical narrative flow, etc.
  6. Create a portfolio website where you can share good information about who you are, what you do, the value you add, and the services you offer.

First thirty days

  1. Start getting good business processes in place, create a contract you can use with clients, get some good accounting software, understand how you can start to market yourself.
  2. Start signing up to job boards, Google Alerts, newsletters, and other places where you can find out about gigs. Listiller is also excellent for consolidating freelance writing opportunities.
  3. Start applying to roles you are well qualified for. Don't worry about charging a lower rate at the beginning, as the main purpose at the moment is to build up a portfolio of work.
  4. Write awesome cover letters that show you understand the niches you want to write about. Share relevant portfolio samples. 
  5. Don't be discouraged, it can take a while to land a gig.
  6. when you get interest, get a contract in place and talk to the client so you can establish exactly what they need.
  7. Do the work!

First ninety days

  1. Build on your success - your focus should still be on building your portfolio.
  2. Get a cash cushion in place as soon as possible (say around one to three months of expenses) - this can help you avoid the feast<>famine cycle so familiar to freelancers!
  3. Get a good productivity tool, schedule, and workflow in place. I recommend SkedPal, but choose what works for you.
  4. Continue to apply to new roles and market yourself.
  5. Cultivate existing clients, see what they do and don't like.
  6. Build your self-confidence and slowly start raising your rates.

Hope this helps!

Jun 6, 10:45AM EDT0
Show all 3 replies

Hi Paul, not sure if I'm doing this correctly (just signed up)...

I have 2 questions for you.

1.  Do you specialize in any niches? I'm currently working with marketing companies and they're only paying me ~$50/blog post. It's enough to pay my monthly bills....but nowhere near the mythical "6 figure a year".

The only specialties I have are SEO. I used to own an SEO company way back in the day, but sold it.

So right now I'm just writing random blog posts for the clients of the marketing companies I work for. It's kinda scary because these marketing companies could dump me at any time (I'm a commodity) and I'm unsure as to how to get legit clients (actualy companies) for blog posts/etc.

2. Do you use direct mail? Or cold emails?  I have used cold emails to get all my current clients.

Jun 6, 9:59AM EDT0

Tony, you seem to be doing splendidly (I only signed up yesterday, so we'll muddle through together!) To answer your questions:

1. Yes, I think specializing is really the only way to go as a freelancer, several reasons:

  • You can make more of a mark in a specific niche.
  • There's less competition, especially if you go super-niche (not that many people writing about organizational design and culture change for business transformation <shakes you awake>)
  • You can demand higher rates.
  • It's easier to build a focused portfolio, which is necessary for getting better-paying gigs.
  • That's why I do specialize - I write about business, tech, and finance, in the B2C and B2B spaces.

2. The main way I find new work is to apply to gigs and job adverts on places like ProBlogger and other job boards. A few tips here:

  • Only apply for jobs you are super-qualified to do, and can back up with relevant portfolio samples.
  • Write an excellent cover letter - tailor it to each position you apply for. I try and find out the founder's name and address it to them personally. also state specifically what you have been able to accomplish, how you will work with them, and don't be afraid to use humor.
  • Research the busienss you are applyintog , and reference that in the cover letter.
  • Always mention your rates in your cover letter.

I just won a piece of work this morning, here's the cover letter I used (the gig is for writing articles around accounting software).

Hi Jon and everyone at ***, 

I know it might be a little bit weird, but I really enjoy writing about accounting and bookkeeping. It's not something I bring up in conversations at parties, but I'm a bit of a data nerd (pivot tables FTW!)

What better use of data than to save money and manage your business a little bit better? I was a UK business owner from 2006 through 2013, and kept tight control of every part of my business. I used (and continue to use) FreeAgent, and was amazed at how much time it saved me - accounting software pretty much revolutionized how I ran my business. 

I moved from the UK to the US in 2014, so now it's all about the IRS, state and sales tax, and other esoterica. Of course, other accounting principles are the same, so I still manage expenses as efficiently as possible, reconcile all my transactions and accounts at least twice a month, and have a day-to-day understanding of all my tax liabilities. To say nothing of the 453 row spreadsheet of every line item I have billed since the start of the year! 

All this is to say - I get it. When it comes to accounting and financial management, it may make some people's eyes glaze over, and I see my job as shaking them awake. This stuff matters - a lot. Making accounting and bookkeeping accessible and useful is one of the best ways to empower business owners. That's why it's vital to use empathy, humanity, and humo(u)r to turn a dry subject into something people can engage with.  

Reading through your website I can see that *** offers lots of excellent features for small businesses, startups, and freelancers. Intelligent banking (yay for automatic imports!) real-time reporting, categories / chart of accounts, and more are all essential for fast-moving, rapidly growing businesses. 

This is all very well, but the proof is in the pudding, what have I actually written? Well, I've written for or about various accounting services like FreeAgent, 1-800Accounting, ZipBooks, Wave, and Kount. Here are links to some of my work: 

Reviews of accounting software

- https://www.cardfellow.com/intacct-review/

- https://www.cardfellow.com/the-complete-zipbooks-review/

- https://www.cardfellow.com/wave-review/

- https://www.cardfellow.com/kount-review/ 

I've also (just) written a 5,000 word review of ZipBooks at their request that's yet to be published. (My fingers are just nubs after that!) 

Good financial management

 - https://www.cardfellow.com/before-profitability-how-long-until-you-run-out-of-money/

- https://www.cardfellow.com/braintree-vs-stripe-which-is-better-for-online-payments/

- https://www.cardfellow.com/true-cost-of-hiring-employees/ 

I have plenty more samples and more about me on my website at www.PaulMaplesden.com 

I hope I have the right mix of skills, experience, expertise, and approach for you to consider working with me. My job is to make your job as easy as possible. My fee for this type of work is a flat rate of £0.** per word, that includes research, writing, and reviews.

I can also work on knowledge base articles, white papers, guest posts, and anything else you need. 

I look forward to hearing from you, Paul.


You can see from this that I have tried to stand out from most other cover letters, and it worked. We're signing the contract today.

Last edited @ Jun 6, 11:02AM EDT.
Jun 6, 10:32AM EDT0

Do you work seven days a week?

Jun 6, 9:43AM EDT0

No, I work Monday to Friday and take weekends off. I typically bill around 3-4 hours a day (the rest of the time is admin, management, seeking out new work, client comms etc.)

It's vital for freelancers to have a good work / life balance. Working from home means it's easy to let those boundaries slip, and that can lead to burnout. 

I wrote about the importance of developing a daily routine here.

Jun 6, 9:56AM EDT0

Do you do any creative type writing?

Jun 6, 7:50AM EDT0

I think most writing is "creative" in one way or another, but if you mean fiction specifically, then no. I think it's much harder to get noticed or earn decent money as a fiction writer (not that those are the only reasons for doing it of course!)

It's also a completely different route to market - writing a book, self-publishing, promotion, Amazon, Kindle etc. Those are not skills I am very strong in, so I tend to stick to what I know.

Jun 6, 8:38AM EDT0

Whose writing style do you admire or emulate?

Jun 6, 6:40AM EDT0

It's people like Tim Ferriss (he is excellent at using context and examples to explain points), Neil Patel, who writes extraordinarily insightful posts, Malcolm Gladwell, Jon Ronson, and others of that ilk.

When it comes to emulating a style, I try to write to whatever the style a client prefers - some want very straightforward, to the point copy, others want inclusive copy, others want lengthy explanations, others want humor and a tongue-in-cheek approach.

My natural style is:

  • Have an overall plan for where you want the piece to go.
  • Use descriptive headings and short paras that cover one or two points each.
  • use bullet lists, numbered lists, and formatting to break up the copy.
  • Use plenty of white space.
  • Speak to the reader directly - I use a lot of second-person in my copy.
  • I prefer active over passive tense.
  • Keep copy accessible, inclusive, and friendly.

That approach seems to work for most of the writing I do.

Jun 6, 8:36AM EDT0

Can you imagine yourself doing erotic writing?

Jun 6, 6:31AM EDT0

You mean bring out the salacious side of pivot tables, the heavy breathing involved in data analysis, or the forbidden fruit of project management? 

In all seriousness, it's just not my genre. I know what I am good at writing, and what I am not. Erotic writing most definitely falls into the second category!

I hear it's very popular on Amazon / Kindle though, especially for self-publishers, so more power to them!

Jun 6, 8:27AM EDT0

Do you have any expenses have a freelancer?

Jun 6, 6:19AM EDT0

Oh yes! Our biggest single expense is healthcare, which is over $10,000 a year (U.S. Health system FTW!) After that it's bank charges, software subscriptions, marketing, utilities, and charitable donations.

It's vital to have an excellent grasp of expenses as a freelancer. That includes all the sundry expenses, plus payroll, and tax (In the U.S. that means self-employment, state / local taxes, and federal taxes.)

It's definitely a good idea to get a good accounting package like FreeAgent or ZipBooks. They can help you to understand your expenses better so you can plan for and pay for them.

Jun 6, 8:24AM EDT0

Have you done any professional writing before freelancing?

Jun 6, 5:33AM EDT0

I had done a little, mainly on writing platforms like HubPages (which is a good way to start out a portfolio.) My previous career was as a communications manager, which meant I wrote communications strategy, messages, websites, etc. for the IT department of a large financial business, so that gave me some good skills and experience.

In terms of new writers creating content for a portfolio:

  • Do write for online platforms like HubPages - although the revenue share is low, it will help you develop your writing style and build your portfolio.
  • Look at doing pro bono work for charities and non-profits. It's altruistic and it gets you exposure!
  • Start a blog - Medium is a great place for getting an audience and developing your style.
Jun 6, 8:20AM EDT0

Where do you find the bulk of your work?

Jun 6, 4:52AM EDT0

The bulk of my work comes from repeat clients, probably around 80%. The remaining 20% comes from new gigs and clients that I apply to. 

My best clients have been marketing agencies, they probably account for around half of all the work I do. I also have a few other clients who use me on a monthly basis.

When it comes to finding new work, I have IFTTT feeds setup (RSS to email) for most of the freelance job boards, and subscribe to email newsletters for freelance writing jobs. I also have Google Alerts setup for various freelance writing related terms.

The best website I have found for consolidating freelance writing opportunities together is definitely Listiller, it's very thorough.

Last edited @ Jun 6, 8:09AM EDT.
Jun 6, 8:04AM EDT0

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

Jun 6, 3:47AM EDT0

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, setup 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!

Hope this helps!

Last edited @ Jun 6, 9:30AM EDT.
Jun 6, 7:58AM EDT0

More than you think!

Jun 7, 12:39PM EDT0

How do you categorize the genre of your writing?

Jun 6, 3:28AM EDT0

Non-fiction, specifically business, tech, finance, and related topics like project management, IT, productivity, software, automation, that sort of thing.

I think it's important for writers (and other freelancers) to work in genres they are very comfortable with. That way you're not having to learn new topics while going through all the other activities involved in growing a business - marketing, admin, accounting, etc.

Having a narrow focus means it's easier to build up a relevant portfolio, share good, representative samples to prospective clients, and build up a reputation as an expert.

Jun 6, 7:43AM EDT0
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