Why I became a freelancer - and three reasons why I can't go back

My journey to being self employed as a freelancer has been a long one. Ten years ago, I first started thinking about going freelance. It all started when my friend Milla gave me Tim Ferris’s book ‘The Four Hour Work Week’. It is full of ideas and examples of how to structure the working week / month / year differently. I devoured it in one day, on a Saturday, and then on the Monday I went into my 1:1 with my manager and asked if I could spend the winter working remotely, on reduced hours. A kind of mini sabbatical / part time remote work gig before remote work was a thing. This was when Skype was the best thing we had to stay in contact - for some context! To my amazement, she said yes. I walked out of that half hour meeting wondering where I would do, and what I would do.

I ended up working remotely from Colombia over the winter of 2013-14, and having the time of my life. I would spend the mornings writing up a research report that was my task for the seven months, and then I would finish around lunchtime and head to a Spanish class or a salsa class, or to meet a friend and sit in the sun. I landed back in London at the end of the trip in March 2014 and knew that I needed to make this a more regular pattern. Freelancing seemed the only way. I couldn’t see a way that organisations could offer me the flexibility I wanted, but at the time freelancing wasn’t that common. I only knew two people who were freelance.

It wasn't until 5 years later, in March 2019, that I finally left the world of PAYE and entered sole trader territory as a freelancer. I’m glad I waited. In that time, I took on two other jobs which gave me great experience, and a strong network, which has been so important in my freelance life. I also had the chance to try my hand at a senior role in Government, and I realised quickly that I missed doing the ‘doing’. In between reviewing hundreds of pages of Mayoral briefings each week, and filling in seemingly endless budget forms / recruitment requests, I realised that I missed what I had done earlier in my career: research and writing. And the more senior I became, the further away from this I got.

There were lots of things which were tempting about going freelance, but in the end - for me - it boiled down to three main reasons.

Reason number 1: I like to be in control

I wanted to have ultimate control over how I ran my life, and my day to day work. This was a little deluded as the first five years of my freelance work have been spent saying ‘yes’ to everything for fear the clients won’t come back if I don't! Where I am able to exercise my control is usually when and how I work. I wrote most of this newsletter from an airport in Lisbon, where I spent 8 days working abroad and visiting my partner's family and friends. I often stop work in mid afternoon to go for a run, or to the pottery studio, and then come back and do an hour of admin in the evening. Sometimes I take a Tuesday off and work a Sunday morning. This control suits me, and speaks to my need to balance different interests in my life without feeling curtailed by a 9-5.

Reason number 2: I live for holidays

When I first went freelance, the pandemic hadn’t yet happened, and so virtual work wasn’t nearly as possible as it is now. My initial objective was to spend the winters abroad. I thought I might do contract work, for example doing a 9 month maternity cover contract and then taking 3 or 4 months off, and then doing the same thing again. The world of work has changed so much since then that I can do more typical project based / consultancy work, and take holidays when I want to.

Excluding 2020 and 2021, when the pandemic made it very hard to take holidays, I have taken between 9 and 12 weeks holiday each year. Mostly between November and March, although last year I took all of August off and it was great. This is the single biggest reason why I value being freelance, and the thing which means I would find it very very hard to go back into an in house job. I never, ever, wanted to have to ask someone’s permission to sign off my holiday time again.

Reason number 3: I do my best work when I have a blank sheet of paper and a goal

And that's what freelancing often is. A goal. A deadline. And often - in my case - a lot of creativity over how the work is delivered. As I said earlier, a big reason for me going freelance is that I wanted to get back to the doing. To the content. To doing research and writing reports, rather than reviewing someone else's work. I wanted to be hands on, rather than feeling as though my time was being spent fulfilling the needs of the organisation I worked for.

I often feel that as a consultant, I get to do the most interesting parts of people’s jobs which they don’t have the time or capacity to do because they are so busy servicing the organisational beast. I spent the first ten years of my life in consultancy and I love project based work, and spinning a few plates at the same time. I love the hustle of chasing down new work and winning contracts, all of which is a big feature of my freelance life.

There are lots of other reasons why I think I would struggle to go back into organisations, but those are the big three. I’ll probably be working for another 20 to 30 years, so I won’t say it would never happen, but organisations would have to get a lot more flexible for me to want to jump back in.

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