What's become easier about freelancing – and what hasn't

From emails and lunch breaks to money and colleagues, what's changed in my freelance life since I started out

I’m in a recalibration phase with my freelancing at the moment. More on the specifics of what that means in a future newsletter, but it’s brought up a lot of ~feelings~ so I wanted to reflect on them here. 

I’ve now been my own boss now for longer than I’ve been anyone’s employee. In the beginning, working for myself was a shock to the system, but now I can’t remember what it was like going into an office every day. Over these last four and a half years, some things have become a heck of a lot easier. While others, on the other hand, just haven’t. 

Let’s start with what hasn’t been any easier.

Not having a regular paycheque

While I don’t worry so much about never being able to find work (more on that below, though), the actual managing of my cash flow and budget remains a nightmare. 

This is partly due to late payments. It’s hard to manage your revenue when it … just doesn’t arrive in your bank account 🙃

But even when I do eventually get paid, the fact is that the world is designed for a regular pay cycle. Bills are due every month. And even if you try to get a handle on your budgeting system, nearly all personal finance advice assumes you have a fixed income. 

I get around this with a percentage system, but it’s an imperfect solution. The best I’ve managed to come up with is setting up a calculator in a spreadsheet that works out exactly how much I need to put into my tax account, savings, and pension accounts. While it’s automated the process of working out by how much to divide up my income, I still have to make those transfers manually every time I get paid. It’s what a tech dude might describe as friction-y. It’s tedious, frustrating and well, just stressful.

My emails

I simply cannot cope with my emails! My whole day can turn – for better or worse – on a single message. I hate how much of my mood is dictated by what’s happening in my inbox. 

When I worked for companies, my emails were stressful because they were the way you demonstrated that you were doing your job. I played a lot of email ping pong, performatively pushing a project along with a lot of cc’ing and circling back. But now, the inbox stress is a very different beast. 

At any given moment, I’m waiting on a reply that will either make or break my day, or even my entire financial year. There are messages saying yes – the commission confirmation; the interview request granted – and there are the nos – unfortunately, you were unsuccessful in your grant application; you didn’t get that gig. Then there are the unexpected and wonderful surprises – it’s rare but every now and then an amazing, well-paid opportunity does come out of nowhere and land in my emails. Every time I go to open my inbox, I brace myself against the weight of nervous anticipation. 

I was talking about it with a freelance friend recently who described it as a slot machine. It’s the perfect analogy – you refresh the inbox like you do pull the lever, hit either with the rush of a win or the crushing disappointment of a loss.  

Lunch breaks

I don’t take a proper lunch break! This was actually something I was great at when I worked for companies. I religiously took my full hour to myself. When I worked in New York, I tried to go out and savour the city (and the amazing lunch choices) as much as I could. Even on the days I didn’t leave the office, I would eat my lunch somewhere else and read until it was time to go back to my desk. 

But for some reason now, I just can’t get myself into a decent lunch break routine. I try really hard to not eat at my desk, but I often do (I did it this very day!). I do think this speaks to a bigger problem I’ve observed, which is that I don’t make as much use of the flexibility that freelancing offers as I’d like. For the most part, I pretty much work the same, if not more, hours I did in regular employment; I probably take less time off, and I definitely spend more time worrying about work than I used to. And yet, on aggregate, I’m still happier overall for some reason. 

This leads me to what has become a lot easier about working for myself:

Asking for more money

I really wasn’t used to talking about money when I first started working for myself. I negotiated my salary once, upon starting a job and that was really the only conversation about my pay that ever happened. 

As an aside: I only ever had two pay rises (outside of pay increases from changing jobs) in the time I was in regular employment. One was in my first job, a university that had a standardised pay review policy and at the end of my first year, I met the criteria for a small pay bump. Then the only other time was when I worked at VICE and the digital team unionised and my salary went up. 

Now, however, I have to ask for money all the time. This week alone I’ve had three conversations about fees. The first was a conversation with my agent about a project that came in. The second was a conversation with an editor I have an existing working relationship with about a new project. The third was another existing client coming to me with a quick turnaround commercial gig. 

I operate an “always ask for more” policy. In the case of the first one, that meant asking the agent to ask for more on my behalf (side note: something very few people talk about is that it’s SO MUCH EASIER to get better at asking for more money when you hire an agent to do that asking for you). In the case of the editor, I asked them directly for more. I did hesitate, but the discomfort was just that, a brief hesitation. I pressed send and then pushed it out of my mind. (I got the increase). And the third and last situation, I actually didn’t negotiate at all because I’d just successfully asked for a rate increase the last time we’d worked together. Present me was very grateful to past me.  

I don’t feel lonely

I have so many freelance pals now. I always got on with work colleagues and become actual friends with many of them, but I’ve never experienced the level of professional support that I do with my freelance coworkers. There’s just no bullshit. It’s as simple as that, really. When you pick your own colleagues, you don’t have to put up with office politics and all the rest of the nonsense that comes with working with others.

Now – I do still spend a lot of time alone, but crucially, I don’t feel lonely. In this regard, I really do feel like I’ve hacked the system. I get to do my work in uninterrupted, blissful solitude but when I have an issue, I have enough people in my orbit who I can connect with pretty much instantly and reason something out. 

Trusting that everything will work out

I don’t know if this is because I started freelancing unexpectedly, but I really struggled to trust that everything would work itself out. If I’m honest, I probably would have felt that way regardless. Either way, for the first few months of freelancing, I was a ball of worry. There were so many racing thoughts and difficult emotions swirling in me that it was, ironically enough, hard to pinpoint exactly what I was so worried about. 

Part of it, of course, was the practicalities of whether the finances would add up. But beyond that was the fact that I’d actually been desperate to be freelance for a long time and I was worried that – now I had this chance to do it – that I wasn’t capable of making it work.

I’m less worried about that stuff now. This is partly because I’ve clocked enough months of everything always being fine to feel confident that everything will continue to be fine. But I’ve realised this issue runs deeper than just being new to something – it’s about learning how to sit in the discomfort of the uncertain. We all have to do that, regardless of how we work but I do feel more confronted by that reality thanks to how I work.  

Of all the things that have become easier about self-employment, this has been the one area in which progress has been slow, painful and non-linear. I don’t profess to have this licked. But continuing to figure it out has had a profound impact not just on my job but my life outside of work, too.