A few years ago, someone emailed me some questions about going freelance, and I responded. Then I decided to turn it into a blog post, because it might be helpful to other people too.
It’s appeared on most of my blogs throughout the years, and I thought it was time to post it on this one, too.
So without further ado: How to go freelance: a Q&A
Did you meticulously plan what you wanted to do before you left work or did you just bust out of the office in a flight of fancy?
Actually a bit of both. I spent two years before I left planning to be a private investigator. I did training courses and went to conferences and stuff, and spent a lot of time studying the trade. I had been planning to leave in March 2013, but a few things coincided that meant October 2012 felt better, so the final decision to leave at that specific point was quite quick, if not exactly impulsive.
Did you move home or continue where you were?
Initially I stayed in the same place (until June 2013), then moved, partly because the rent is cheaper in my new place and so I didn’t need to do quite so much to make ends meet, therefore freeing up more time for voluntary stuff; and partly because I fancied a change.
Did you have a significant amount of savings to rely on (just speak in general terms not specific numbers)? Did you have a significant number of outgoings (again, I don’t want to know specifics just generalisations).
Oh hell no, I was terrible at this. I had enough for about three months’ rent. But I knew I had to make the jump. Outgoings-wise: well, I’d just quit a pretty well-paid job, so I’d become used to a certain level of outgoings, but I’d spent most of my life not having much money at all, so switching back to lower outgoings in terms of food, going out, etc. wasn’t too difficult from my perspective. The main pain in the ass was rent (ultimately one of the reasons I moved: managed to cut my rent from £900 for a 1-bed in London to £350 for a 2-bed in Sussex).
What are the biggest changes?
Not being around people. Personally, I love this. Don’t get me wrong, I had great friends in my old job and I loved hanging out with them (and still do), but I am so much more productive when I’m on my own.
My routine changed entirely. I am not a morning person and now that doesn’t matter at all, because if I want to I can get up at midday and work until 3am and no one gives a damn. It’s fantastic.
Money. Not so much whether you have enough of it (although I didn’t), but the fact that you don’t know you have a pay cheque coming at the end of each month. I’d freelanced before, but I’d forgotten the feeling of having no idea how long I had to last until the next injection of cash.
The one thing I miss is having a manager, which surprised me because I’m a very independent type. But I’d had a fantastic boss who was essentially my opposite in every way, and when I was at my old job I’d really appreciated the ability to just pull him into a meeting room and say “I want to do this with my team, is that insane?” and just have another senior person to bounce ideas around with.
You are every department. I’d come from a start-up, which by the time I left had grown into a corporation, so I was used to this to some extent – I’d done stuff for pretty much every department whilst there – but it’s different when (a) you are literally everyone and there’s no one there with more expertise than you, and (b) it’s your own business so you care about it so much.
In your opinion, what do you enjoy most about your new way of life?
The ability to structure my own time. The lack of necessity to communicate with people when I don’t want to (I am not quite as anti-social as I am sounding here, just a bit of an introvert!). Being able to ‘scale up’ and ‘scale down’ on certain projects whenever I want to. And also, if I’m honest, having some of that initial fervour back. When a company – or an individual – is just starting out, it eats up all my time and I become quite obsessive about it. I really like that feeling, and I’d missed it by the time my old job had got to the stage where I was just working 9-7 and performing a function.
On a side note, I have also found that I’ve become less apologetic about who I am in general. This is partly because I get to choose who I work with and turn down clients if I want to, so if someone says “What are you doing this month?” I can say “Working with Charity X on their social media campaign” instead of mumbling “Running an advertising campaign for Huge Corporation, I am very ashamed.” But it’s also just easier to define myself now – without wanting to sound too corny, working for myself has made me understand far more about who I am than working in someone else’s company ever did. I now have a really good idea of what motivates me and also of the things I tend to put off.
Which jobs did you consider when you left?
I’d been planning the investigation thing for a while. I briefly considered moving into another advertising company for a few months, just to get a taste of working in a place that wasn’t my old company for a bit, but then I decided just to strike out on my own. And investigation was the only thing I really considered.
How did you decide on the jobs you are now working? Did you look at your strengths or was it more based around what you had a passion for?
…and then it all changed! Well, not so much changed, more just evolved.
I had decided on investigation because I wanted to take the skills I’d learned in my old job – finding out where networks of people hang out online in order to target them with ads – and use them for something I cared about. I did a lot of thinking and came up with internet crime, specifically child protection. Did all the required training courses, worked on a couple of cases before I left, then struck out on my own. Quickly realised that, whilst I was good at solving cases, I had no idea how to sell investigative services. This came as a surprise, because I’m not bad at selling advertising/social media/marketing services, but somehow investigation was something I just couldn’t work out how to sell. I’m working this out as I go along, but it’s still going slowly.
People who already knew me or had worked with me before also seemed to want me to help them with digital marketing. I wasn’t really hugely excited by this prospect, but by this point was going to do pretty much anything if it meant avoiding going back to a day job and still making rent. I started helping people out with social media stuff, and then quite late on (only over the summer) realised that this would be a plausible business plan in itself. I then realised that what I’d actually done in my old job – setting up new departments specialising in international briefs and then eventually moving them to other offices/letting them run themselves – was probably even more of a sought-after specialist skill. Also, I knew a lot of freelancers who spoke different languages.
These things sort of coincided in my mind, and I decided that setting up a ‘freelance collective’ might just be the way forward. I did a bit of tentative market research, speaking to a few potential clients about how all this might play out, and then when I had a few people interested, decided to set it up. A chance encounter with a friend who I hadn’t realised was in fact running a very similar business but in a slightly different industry was very useful here, as I’d been worried about the logistics of setting it all up and she has been massively helpful.
50% planning for ages, 50% purely by chance.
What’s the worst bit of your daily routine?
Good question! I don’t really have a daily routine… and I’m not actually sure. I think I can honestly say that I don’t have a worst bit, because I love the fact that everything is changing all the time and I never know where I’ll be next. That was one of the things I wanted when I started out: I missed the times when I was freelancing before and I’d wake up in Leeds with a sudden realisation that I had less than twenty-four hours before I had to be doing something completely different in Bristol. I love that level of adrenaline rush.
With multiple jobs do you get much time to relax/enjoy hobbies?
Well, kind of, in that my jobs basically are my hobbies. In my old job, it made me sad that I didn’t get time to read as much as I used to, or perform on stage anymore, or do anything creative. When I left, I realised that I could turn these into (admittedly far less lucrative) income streams as well. I now review books on my blog, which means I get a fairly steady stream of new releases dropping through my door, and also that I can justify reading time as working time. Likewise, I spent a weekend in my friend’s bedroom putting together a very sketchily-recorded EP, sent it out to a load of venues and started getting gigs. I am just reaching the stage where I’m being paid enough for them that I not only cover my transport costs but actually have money left over as well.
In much the same vein, one of the main things I used to do as a “hobby” (odd word for it, but true I suppose) when I worked at my old job was investigating things that were happening online. I find it fascinating and I love the process. I love that I can do this as a job now.
If anything, I’d actually say that I get more time to relax now, even outside of these hobbies, but that might be because I was working insane hours in the city. At one point I was averaging a 71-hour week (yes, I do mean “averaging”). I often slept overnight in the office. And it was difficult because I felt constant pressure to make sure everything was perfect, and because it wasn’t my own company I was never 100% sure what ‘perfect’ meant.
Now, I know that if I take time out to do something else (sitting by the sea writing poetry, climbing trees in my local woods and spending weekends around a bonfire at my friend’s farmhouse are three examples of proper ‘time out’), it will be time that isn’t being spent on the business. But because I know what my own business goals are, and also I have a good understanding of how I work, I can structure my time sensibly, e.g. I can say “OK, I will go to my friend’s house this weekend and will take two days off, which means I have to move deadline X back by a day.” But that’s OK, because I am the boss, so I can say that.
It’s worth noting, however, that if I have a client project that I’ve already committed to, I never move these for recreational reasons. But I do move around inessential admin for the sake of chilling out sometimes. Because the spreadsheet is not going to die if you update it in three days’ time instead of tomorrow.
This is going to sound really cheesy, but one of the things that keeps popping into my head is this, which I pinned on Pinterest ages ago and I think is very true:
If you live by that rule, then you end up doing your hobbies as a job, and it’s great.
If you had another chance at leaving work would you have done anything different (no matter how small?
Yes. I would have spent less time studying the bits that are easy to learn “on the job” and more time studying the business side of things. I went into it with an attitude of “I’ve never been an investigator before, I must learn ALL about that”, when actually a lot of it – particularly in digital forensics – changes all the time anyway, so you end up having to Google answers to lots of stuff even if you’ve theoretically done the training course.
I didn’t read any business books and went into it with quite a ‘well, I’ve freelanced before, I can do it again’ attitude. This was true, but previously I’d been happy to just have bits and pieces of everything and hadn’t wanted to build a career out of any one of them. I’m still a bit like that, but there are a couple of strands that I want to properly pursue, and that means things like professional indemnity insurance and proper bookkeeping and cold-calling to sell services and things. That’s difficult, and I underestimated it.
I would try to find a mentor. I have one now (my friend with a similar business), but it gets very difficult very quickly when you have to make all the decisions. Bouncing ideas off someone else is really useful.
I also read Start Your Business In Seven Days by James Caan a few months in and really, really wished I’d read it sooner.
Any general advice?
No one tells you about the swirling pit of terror.
The swirling pit of terror happened to me and to two of my ex-colleagues who also struck out on their own this year, yet none of us had heard about it and none of us were remotely prepared for it. Worth noting that we are all un-emotional people generally (the word ‘robot’ is often applied by my friends).
There came a point for all of us a few months in where it just seemed interminably difficult. We’d been doing everything by ourselves, making money was hard and we weren’t sure where the next bunch of clients were coming from. For me, this happened over the summer when all my clients simultaneously took holidays which they’d forgotten to tell me about. Unfortunately my landlord hadn’t forgotten to charge me rent, which was a problem.
In general, I look at things logically and find solutions pretty quickly. I’m an INTJ on the Myers-Briggs scale (actually, I recommend doing that test at some point as well, partly just because it’s interesting but it does also give a useful insight). And yet somehow, after a couple of months of having no clue exactly what I was going to do next, I entered this state of complete… I don’t even know what to call it. It’s probably best illustrated by what I did, which involved solely: sitting on my living room floor, clutching my landline and staring into space, wondering whether I was actually losing my mind. For one of my friends, it involved exclusively eating soup and bread for six weeks whilst sitting on her sofa in a permanent state of panic. For my other friend, it involved lying on the sofa watching reruns of TV shows despite knowing that he was soon going to be without a TV and a house to watch it in if he carried on doing nothing.
Again, we are all driven, logical people, not the kinds who bring their personal problems to work, or even get particularly wound up about personal problems in the first place. But the swirling pit of terror is a horrible thing and you just have to sit it out. For all of us, it lasted between 8 and 12 weeks. And then it was fine again – my clients came back from holiday, Friend 1 finally got paid for the invoice she’d been chasing, and Friend 2’s app got a review in Mashable and suddenly everyone was interested. At the time, it’s terrifying, but it’s worth sitting it out.
The only other piece of advice might sound weird.
Don’t get too caught up in productivity.
You’ll find lots of things online telling you how to be more productive, and using them to an extent is helpful. But actually, a lot of them will take up more time than you realise. One of the best ones I found was “exercise daily”. It’s a great tip and it genuinely helps. I started running every day, and it’s a great way to clear my head and get the day off to a good start. But it’s quite easy to suddenly realise that you’ve been running for an hour and you were supposed to finish that brief a while ago, or that you’ve colour-coded your folders like the website told you to but you haven’t submitted an invoice on time.
All things in moderation, and timing is your friend.
Now I run for half an hour in the mornings, and then if I want to, I go for another run later in the day when I’ve finished all the urgent pieces of work.
I think that’s everything. Can basically be summed up in one sentence:
It’s fucking terrifying, but it’s totally worth it.