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  • Kathryn Bailey

Then & Now: A Candid Look at an Online Business Over a 3 Year Period (With Real Figures)

Updated: Oct 27, 2022

Part One - The First Year


I’m writing this to you because in my first year as a Freelance Writer I read a random blog post by a woman called Denise Duffield Thomas who had written a detailed look at her first year in business which was completely transparent and covered all the issues she had including her real business statistics.  It was such a relief to read a real behind scenes look at what it takes to manage an idea through to a successful business so I thought I’d give you a look at my first year as a Freelance Writer, so you can see what you might be in for (it’s mostly good, but a steep learning curve). I’m working on a (3) years later post now so you can see the changes but for now – enjoy.

In this post I’ll share my:

  1. Real income statistics (month by month)

  2. The things that worked for me.

  3. The mistakes I made.

  4. Some of the business resources I have used – the complete list is here.

The First 12 Months as a Freelance Writer:

The Idea

Before I launched my online business, I’d been employed as an Employment Consultant for most of my working life. When I had my first child I knew I didn’t want to go back into the stress of Mon-Fri, 9-5 but honestly, I never even considered doing anything in this area. I’d been an astrology nut for years, so I really wanted to turn my hobby into a business.

I started an Astrology site from scratch and despite being published in some newspapers and building a small following I still needed a Bridge job to help pay my bills. Around the time I was thinking of heading back into the workforce on a part-time basis, a friend needed his resume done. With my background I was able to build him a resume and get him a job within the first week. This planted the seed idea of offering my writing services as my bridge job instead of going back into the workforce.

Testing Phase

I’d been fortunate enough to read ‘The 4 Hour Work Week’ by Tim Ferris prior to this so I knew the value of testing an idea before putting heaps of money into it. I used the testing formula outlined in his book to make sure the idea was going to be viable. And viable it was!

I set up a really basic website using Webs (which I highly recommend as a website if you are just getting started). It was pretty much a sales page and not much else. It was also really basic which proves that you really don’t need to freak out and hire a web designer straight off the bat. This clunky DIY website started converting sales straight away!

I used Tim’s strategy to test the idea and that’s how I got all my first clients. I nearly fell off my chair when in the first few hours of my site going live, my first client called through! Honestly, I was terrified. I knew how to write resumes, but this meant I was officially in business for myself and it was a whole new ballgame. For the first month during the test run, I made sure my work was priced really cheap (crazy, I know) and came backed with the best guarantee in business. This guarantee was that I wouldn’t invoice them, if they didn’t like my work. Talk about taking the risk out of doing business with me. I don’t at all recommend this strategy long term for a zillion reason (which I’ll cover later) but it was how I achieved all my first reviews so in the short-term I don’t regret this decision at all.

My first three clients were awesome but my fourth was a total nightmare. He wanted me to make up fake statistics for his work and when I refused, he didn’t pay me. The experience did help teach me a valuable lesson in screening clients for potential issues though, so it wasn’t all bad (more on that later).

First Business Quarter:

Website Revamp:

After the first month I decided to add some more pages to my website and fix my sales copy. By now I had testimonials from other clients, so I added these which made a big difference to the amount of sales conversions. I also added a FAQ page which cut down on the amount of time I spent on the phone responding to frequent questions.

The ‘No Risk’ Guarantee

The whole ‘no risk’ guarantee didn’t cause as many problems as you might think but it always had the potential to blow up in a big way (ie: word gets out on an online forum, scammers order resume, turn down other clients because work-load is full not realizing they are scammers and then not get paid for a single one). Thankfully this never happened to me, but it was always a little niggle in the back of my mind and I knew that it could happen at any-time.

About 90% of clients paid but the thing that eventually pushed me into requiring payment up front was because the majority of the time, the 10% that didn’t pay would go ‘Missing in Action’ and I’d never hear from them again. Without the feedback, I had no way of knowing if they were legitimately unhappy or if they just never intended to pay in the first place.

I had introduced a statement on the order form and in my first email correspondence with each client that feedback was required to be eligible for non-payment but it never happened. They would just disappear and never answer their phone or respond to emails. Frustrating! At this stage business contracts were all new to me so there was no way to enforce the feedback rule and the not knowing really sucked!

Every so often I would be able to surprise one on the phone by putting my phone on private and usually the reason given was batshit bonkers. For example, one customer told me he wasn’t going to pay because I used black text to write his work and he found black depressing which would make people think he was a depressed person. Did he think the text should be hot pink? I never managed to find out……..

I always sent out feedback forms to my clients (paid and non-paid) and the feedback was awesome. But not a single time did a non-paying customer ever fill out the feedback from which was kind of weird since they were the ones that supposedly had complaints.


Right from the start I was flat-out with customer orders and had to turn people away. At this stage I was still working on my astrology business and wrote  in the afternoon. My income was as follows:

Month One: $5093

Month Two: $6563

Month Three $6762

Note: this does not include any income from the astrology site – just the writing.

Trying to Grow:

One of the biggest problems at the start was too many customers (which is an awesome problem to have). To fix the issue I tried (and failed) to hire an assistant to help me. I used Elance and was initially thrilled with the guy I selected because he had an awesome portfolio of work, but it soon became apparent that the ‘portfolio’ wasn’t his work and he had no idea what he was doing. This burnt me out of trying to hire again for a really long time.

That said, I did find a company to outsource my phone calls from. This was Laura who previously ran a remote reception company prior to becoming a business coach. She was a god-send. All I had to do was divert my mobile to her and she would answer the questions, book the appointments and take the orders. This freed up a LOT of my time.

Second Business Quarter:


I ended up pregnant with serious morning sickness for this quarter and only worked 2-3 hours a day as a result. This had a pretty impact on my earnings but was still pretty good when you consider that’s only 10-15 hours work per week.

Month Four: $3916

Month Five: $4522

Month Six: $2512 (included a two week holiday)


There is nothing like being sick day in and day out to want to make you put some boundaries into place. At this stage I had none – not even office hours because I would always respond to emails straight away from my phone and go above and beyond to service clients. For example, if someone called at 6pm and needed work the same night, I’d still pull it on. I’d also get calls at 2am because of different time zones and as a pregnant woman already with a baby, this was insane.

Laura with her reception service solved the issue of client phone calls and I started requiring at least 24 hours’ notice for any orders. I also took the email off my phone and implemented auto-responders letting clients know when I was available. I always imagined this would be an issue for my clients, but no-one ever questioned it, so I wish I’d done it sooner!

3rd Quarter:

The Most Horrible Client Ever and The End of the ‘No Risk’ Guarantee.

It was my 9th month of business that I reached the end point of the ‘No Risk’ Guarantee. At this stage I occasionally wrote selection criteria for clients as well which is a lot of work and effort on my part. The guy I wrote it for had told me he was really happy with the job I had done but when I sent him the invoice he told me he had found a competitor that had a cheaper price and therefore was only willing to pay me what the competitor charged. Even though it was me that had done the work, he was going to use it and he had no idea what sort of job the other writer could do for the reduced price!

Did it make a difference to my sales conversions? Yes.

Did it make a difference to my income? No

Basically, by cutting out the 10% that took advantage of the ‘No Risk’ guarantee. I was able to service the clients who were genuine and the 10% increase in payments offset the dip in sales conversions.

A (Slightly More) Pro Website:

By this stage I wanted a website that had a bit more functionality and could integrate with some of the other platforms out there. I’d heard great things about Wordpress and decided to give it a go.

This was the biggest technical nightmare of all time BUT in the long run it was worth it and if I’d discovered some of the themes earlier it would have made the tech side a whole lot less daunting. Anyway besides the integration facilities, the best part was being able to connect it with Leadpages which allows you to create really nice professional sales pages. This skyrocketed my conversion rating and Leadpages is really easy to use.

Marie Forleo’s B-School

Something that I wish I had done sooner because it would have saved me heaps of time through trial and error was to invest in ‘B-School’ run by Marie Forleo. It had everything I needed to know to cover my first year in business and had a really supportive group environment, so I wasn’t totally alone anymore and could always find help when I needed it. I really recommend B-School for people just starting out but if you have already survived and thrived after your second year in business, there is probably a more advanced course out there for you. But for beginners? It’s the bomb.

4th Quarter:

By now I had recovered from morning sickness but still wasn’t working full-time. I was probably up wot working 25 hours per week at this stage. I should also note that I took 3 weeks off to go oversees and didn’t work at all (didn’t even take my laptop). The holiday was great but shutting down the business completely for nearly a month did put a dip in my earnings.

Month 7 - $4850

Month 8 - $3730

Month 9- $4838

Thanks to B-School, I finally learnt the value in building an email list. I used Mailchimp which was super easy to operate and it meant I ended up with more referrals from past clients because they could always remember my details for their friends. I email my list about once a month with job-search tricks and tips to keep me in the front of their minds.

$$$$ It was going to be my best month ever ………………

Month 11 should have been my most profitable month ever and it was………..until I went into labour early and had to refund a bunch of orders that would have taken me there!  I’d just beat the $6700 mark with 8 days left when baby Nebraska decided to make an early appearance. I had mentioned the remote possibility of this happening to customers and only taken on work that had long deadlines so they were all super nice about it.

After Nebraska arrived I took four months maternity leave which was fantastic. At first I thought I wouldn’t need it but I’m glad I took it because I’d underestimated how challenging a new-born and a toddler were at the same time! That meant that I didn’t do any work at all for month 12.


Month 10: $5525

Month 11: $4178

Month 12: $250

Three Years Later:

I’ve just written the updated version of this post, so you can see where I’m at now (I’ll include stats again) and the new lessons, boundaries and experienced being a Freelance Writer has shown me since then. I’m currently editing it so if you want to read Part Two, follow me on Facebook, Twitter, LinkedIn or Instagram and I’ll let you know when its live. You can find the links to my online profiles in the top navigation bar.

If you enjoyed this post, please help me spread the word by sharing on social media or within your networks. It would make my day.

Much love and stuff


PPS: If you enjoyed this article I would LOVE for you to share it on your social networks.

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