10 Years of Working Online – My Business Journey

I can’t quite believe it, but this August marked a decade since I registered as self-employed! It hasn’t always been easy, but I’m so proud of what I’ve achieved. Here’s a quick look at how my online business has changed since I started in 2008…

2008-09: Blogging & Freelancing

I finished university back in the economic crash of 2008 and was finding it really hard to get a job. Someone told me I might be able to make money proofreading, so I did a few Google searches and came across an online marketing forum looking for writers on all sorts of subjects. Little did I know that there was a whole online content world out there!

I got my first gig writing an article about ethical travel, and I had money in my PayPal account by the end of the day. I found it easy to find work with webmasters who were basically putting up content-based websites hoping to make money from advertising or information products, and turned it into a full-time income. I found a lot of the articles very tedious, but I was 21, I had no job, I was living with parents, and I needed the money.

I feel embarrassed to admit it, but I only earned a few dollars per article at this time – meaning a lot of writing to create a “full time” income from this (and it quickly led to burnout, which I’ve written about in a separate post – click here to read it). As my schedule got busier, I did raise my rates a few times, but not nearly as much as I should have. I was targeting completely the wrong market, and this was an important lesson that still serves me in my business today.

While I was freelancing, I was also blogging under a pen name. I’d started the personal blog while I was at university, and I found it an amazing creative outlet. I had a good base of loyal readers and made income on the side from sponsored posts.

2010-11 – Products & Website Flipping

As I mentioned, I quickly got burnt out writing day in day out like a machine. Although I found the work frustrating – it wasn’t anything creative, it was simply churning out content – it did open my eyes to this whole new world of online business, especially the “digital nomad” lifestyle I got my hands on “The Four Hour Workweek” by Tim Ferris, and was blown away by the possibilities. So I decided I needed to stop trading 100% of my time for (very few) dollars. This is when I started to create products.

First, I noticed that people would create content packs and then sell them to customers, so I started doing this too. I meant I had more control over the topics I wrote, and could do things on my own terms. As well as article packs, I also created entire websites and sold them as ready-to-go-packages on Flippa. I’d make several hundred dollars per website, which again was probably too low but was huge for me at the time and really turned things around.

It was all this that formed the foundations of my business and income for the next few years.

2012-13 – Travel & Outsourcing

I continued to read and be inspired by stories of entrepreneurs who were living less conventional lives and finding ways to earn “passive income” online (at the time I didn’t quite realise that passive income isn’t as passive or as easy as some make it sound). My income was anything but “passive”, but I started to see the potential of creating products that could be sold at any time, even in my sleep.

I experimented with courses and eBooks, where I taught people how to increase their freelance writing income, and to build a business as I had done. They were very popular, but I definitely undercharged (which is a recurring theme in my business!) I even self-published a book called “Online Writing Freedom” on Amazon Kindle which sold pretty well but didn’t make me much money, and has since been taken down!

I started to wind down the freelance writing a bit and planning a big trip around Asia in 2012. I left with my now husband on New Year’s Eve 2011 with a one-way ticket to Thailand (and a six-month visa), not knowing when we’d come back. He quit his job a couple of weeks beforehand and we decided he could help out with my business. We saved up a little money before we left, but the beauty of my business meant I could carry on earning whenever there was Wi-Fi (although sometimes it was almost unusably slow!)

Travel really opened my eyes to the potential of this whole online business thing! I wanted to spend more time exploring, and less time working, so this is when I started outsourcing. It was a great time to experiment since our living costs were so low (we spent an average of £21 per day each during this time – yes, I kept a spreadsheet).

I soon become more a manager of my business, rather than working in it all the time and being limited by the number of hours in the day. Outsourcing also had an added, more unexpected, benefit – it forced me to get more organised! I suddenly had people waiting for me to place content orders, so I had to do the work and plan in advance to keep things running smoothly.

We ended up travelling to 7 countries throughout the entire year of 2012. It was great to have such a flexible business as it meant we could stay in places longer than the average traveller and really get to know the culture. We visited Thailand, Laos, Cambodia, Vietnam, Burma, Malaysia and Japan and it was an unforgettable, eye-opening experience for me (who, when I was younger, said I was never interested in travelling!)

2014-15 – Stepping Things Up

Despite starting to outsource, I had let my business slide a little during our year of travelling thanks to lots of distractions and low living costs (which, I want to emphasise, was more than worth it). 2013 was a bit of a catch-up year, but by 2014 I was ready to get serious again. By then, I was managing an entire team of writers providing content to website owners around the world.

Chris and I got engaged at the beginning of the year and it was then when I started to see how important mindset was to my business success. I realised how expensive weddings can be! So I started to get a lot smarter about my work. I outsourced more and more and spent more personal time on the bigger picture of growing my business and planning for income from my products. I found that planning in advance really helped to keep me on track, and my income had a pretty big jump this year!

The next year was the same. We decided to start saving for a house, and I can honestly say I thought this was impossible. Even if I could get a deposit together, I never thought I’d be able to get a mortgage approved due to unhelpful rules for self-employed people. I was so wrong! As well as having yet another massive jump in income when I put my mind to saving for a deposit (mindset really matters!), I also learnt another important lesson throughout the whole home-buying process: that getting the right help can make a huge difference. Instead of struggling to find a self-employed-friendly mortgage lender ourselves, we used a broker who knew who to go to straight away. It made the process so much easier, and we ended up moving into our first house in October 2015.

2016 – More Money, Less Satisfaction

For the first time in my life I was earning good money and feeling like everything in my life was so much easier as a result. I could afford to take regular breaks away – some “working” holidays, and some for pure relaxation. I worried far less about how much money I had, but that opened up a lot more mental space to worry more about the fulfilment I was getting from my work.

After coming back from my travels in 2012, I had a growing dissatisfaction with my business. I’d previously always enjoyed it, probably because I was constantly learning and changing what I was doing. But my focus was more on just earning the money, rather than any long-term legacy. I felt like I was contributing to the online culture of churning out content, rather than putting out something truly useful into the world. But I didn’t yet do much about it, feeling a bit “trapped” by having a good income and wanting that to continue.

It was 2016 when I trained for and ran my first (and, as of writing, only!) marathon, and started taking a way more relaxed approach to my days. I also started to realise that endless “hustle” wasn’t as great as it’s made out to be, which you can read more about in this separate blog post.

I’m also really pleased to say that my business allowed my husband to quit his job in 2016, which had been a goal of mine for years. (He is working on a business that also has the potential to have a very positive effect in the world (in a very different way), as an ecopoet helping adults and children connect more to nature and the environment.)

2017 – Big Changes

Something I should’ve done years ago, but was too scared to until February 2017, was to start working as a limited company. I got everything in order and hired my accountant, and it was one of the best moves I’ve made for my business. I can’t believe I’d been trading for eight years, worried I was doing my tax returns all wrong, before I had the courage to pay somebody else to do it for me.

I also got myself into a bit of a mess by not saving up tax money as my income shifted upwards, ending up with a huge bill at the end of the year. In 2017, I started setting tax aside as soon as I earnt the money – and it felt good.

I spent a lot of time thinking about my next move. As entrepreneurs, we tend to come up with new ideas really quickly, work on them with 100% enthusiasm for a few weeks, before moving onto the next great idea. I didn’t want this to happen again. Unfortunately, I spent too long thinking, and let fear get in the way of taking action many times.

But I do cut myself some slack for not making massive changes during 2017, as it was in March that year I found out I was pregnant. Through the nausea, tiredness and mental challenges of pregnancy I got really serious about organisation and business systems and started planning a 4-month maternity leave from my business. And on December 2nd I welcomed baby Rowan into the world.

2018 – Balancing Work & Motherhood

So this takes me up to where I am right now, I’m back at work and trying to create something more meaningful. Since Rowan was born, I have a deep desire to do work that matters, and something that he will be proud of his mummy doing. And I want to spend my time away from him doing something I really care about.

Of course, I am still in the very early days of balancing business and motherhood. The journey hasn’t been easy at all, and I often feel guilty when I want to work (because work is a welcome break from the very difficult job of entertaining a baby!) But I feel ready to tackle the challenge. One thing I know for sure is that being creative in my business, and starting new things this year like my Instagram account and my podcast, Creatively Human, have been a lifeline during the difficult early days of motherhood.



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