Posted on Tue 19 July 2016

The ups and downs of freelancing

I've been freelancing for most of the time since I left Buffer a couple of years ago. Freelancing comes with some unique perks that make it a good fit for me as I try to spend lots of time building Hello Code, but lately I've been noticing a lot of the downsides that make me miss working full-time as an employee.

Everyone's experience is different, but so far these are some of the best and worst parts of my experience working on content marketing as a freelancer.

Upside: Flexibility

One of the main reasons I chose freelancing was because I can choose my own schedule. Assuming I can get enough work, I can work as little or as much as I want. This gives me the freedom to spend more time working on Hello Code, which doesn't pay me a salary yet. It also gives me the opportunities that come with a remote job: going to appointments during the day, choosing my hours, working around other people or commitments in my life rather than 9-5.

Downside: Being an outsider

As a freelance contractor, most of my clients don't give me the kind of information I'd have if I were an employee. I don't get access to analytics to see how well my content's doing. I don't see numbers on which content's working best, or which posts are driving more conversions. I don't get access to internal discussions or documented goals that relate to what I do.

This can make my job harder, as I don't know the business and its goals as well as I would as an insider. It can also make it harder for me to make myself indispensable to the company, as I never know whether the content I'm writing is working for them, or what direction they're thinking of going in next.

Downside: Lack of reliability

As a freelancer, you have the extra concerns of making sure you always have enough work to pay your bills, and getting paid for that work. As an employee, (mostly) not worrying about those things is a perk of the job.

Handling this part of my job is definitely one of my least favourite ways to spend my time. I'd love to have someone else take care of finding new clients, sending invoices, and pitching new content topics to existing clients, so I could just write all day.

But apart from the hassle of all this busywork that takes me away from writing, there's also the constant stress around whether I'll have enough work this month. There's very little reliability in freelancing, even when you work as I do, with ongoing contracts for regular work (as opposed to contracting per project). This was painfully evident when my biggest client suddenly went silent and started ignoring all my communication a couple of months ago. After months of relying on this client for half my monthly income, I had to scramble to fill those gaps with no warning.

That stress is a huge downside, and makes me miss the comfort of a regular job.

Upside: More control

In some ways (not all) I have more control over my work as a freelancer. The main difference is in deciding what work to take and which potential clients to turn down. I'm picky about my work, and I turn down a lot of clients who want content I'm not interested in. In fact, I left a well-paid, supportive job at Buffer because they wanted to me to write more about social media, which I'm not interested in.

These days one client could be the difference between paying rent or not for the month, but I'll still turn them down if the work is something I can't get at least a little excited about.

Balancing my values and my need to eat can be tricky, but it does feel good to have control over the work I do.

Upside: Building my name

Though it's not always the case, it's a lot more common for my freelance work to help me build my personal reputation than working for a company, where the business is more important than me personally. For instance, I usually get a short author bio for freelance articles that includes a link to my own website, or to Hello Code.

This helps me build a personal brand and audience I can take with me when I stop working with freelance clients.


If you're in the market for content marketing, I'm currently taking on new clients.

I tend to write about productivity, psychology and human behaviour, life hacks, communication, remote work, and company culture. In the past I've had my work published on Lifehacker, Inc., Entrepreneur.com, Salon, Time.com, Quartz, The Next Web, and Fast Company. I've written single articles that amassed over one million readers, and increased the Buffer blog's monthly unique views by 59% in my first month on the job, and doubled them in the second month.

You can see an ever-updating list of my previous work here.

If I sound like a good fit for what you need, send me an email.

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