Switching from Freelancing to Employment in the WordPress World

Vom Freelancer zum Angestellten in der WordPress Welt
In this article, Inpsyder Willem gives a very personal insight into what it's like to switch from freelancing to employment.

Switching from Freelancing to Employment, that is the topic of today’s Advent Calendar post. Inpsyder Willem describes some of the differences he came across after transitioning from freelancing to being employed. Before he started working at Inpsyde, he worked as a freelancer for seven years, so he knows a thing or two about the struggles.

Switching from Freelancing to Employment

Hi. My name is Willem Prins and I am a perfectionist.

I think we all know what perfectionism looks like. In the case of this blog post, it isn’t hard to picture either: Imagine a cursor on a line, optimistically moving forward until it suddenly comes to a halt. A finger landing on a Backspace button, forcing the happy cursor to eat its own words like a Pac-Man in reverse. Slowly, it starts to move again, hesitatingly, leaving behind words that appear to mean the same, but sound different. Some added punctuation. But then once more – you guessed it – the cursor stops again, a pair of eyes blink, lips are pursed and a mouse click drops the cursor on a different line, where it is forced to perform its generative/destructive line dance once more: country and western meets character assassination moonwalk, if you will.1

So what does this have to do with freelancing? Or the differences between freelancing and employment in the WordPress world? Very little, at least at first glance. But for me, if we were to describe my freelancing career as a party (and I stubbornly choose to believe there are people whose professional lives resemble the music video for Miley Cyrus’ ‘We Can’t Stop’), perfectionism is that one ‘friend’ who always shows up uninvited, with his buddies Income Impostor Syndrome and Income Insecurity in his coat-tails. Turns out: as I finally made the switch from self-employment to joining Inpsyde, I soon found out that, with one exception – can you guess which one? – these uninvited party guests are persistent. Or they must really like me.

There are many different aspects to freelancing and working for a boss (at Inpsyde, our boss’s name is Alex and, among many other things, he likes to talk numbers). There are heaps of Painfully Accurate memes that illustrate the downsides of freelancing. But surely, there are probably just as many memes about life as an employee. But since the finished version of this post was due two days ago (Hello irony! And sorry Jessie!), I will limit myself to perfectionism and his two friends.

(Dealing with) Perfectionism

Perfectionism is a drag. Looking back, I wish someone had told me that before I start doing any paid work, I should learn to Get Things Done [tm] deeply. Had I ever been forced to write ‘done is better than perfect’ on a blackboard ten times, telling me that really, perfect scripture and vertical alignment are not part of the assignment, maybe I would have been able to develop a healthier work ethic early on. I would have developed a more pragmatic attitude towards creative projects in general and coding projects in particular earlier. As a freelancer, your clients do not usually tell you not to worry about details so much. So when push comes to shove, you are the only one who can stop you from pouring countless unbillable hours into tweaks and improvements the client never specifically asked for. So you would think, or hope, that this changes when you are part of a team, right? Right?

Yes and no.

For as long as I can remember, I have rather euphemistically listed ‘eye for detail’ on my resumé under personal qualities. And yes, I always hoped that no one would notice (Alex?). Because yes, it is great if you quickly spot things that are ‘not right’. As a front-end developer, it comes in handy when you automatically notice elements that somehow escaped the relevant media queries.

Acceptable and not-so-acceptable forms of perfectionism when Working for an Agency

When you’re a bit of a grammar-and-spelling nerd, like me, your first pull request on an official WordPress project will probably involve improving some wording in the documentation for Gutenberg. That’s cool. Or in the company Slack, your first project-related question amounts to double-checking whether the inconsistency in package naming is intentional. No biggie. As long as you are nice about it, colleagues will most likely appreciate your efforts to tidy up that one repository. Even when it’s almost abandoned. These advantages are quickly undone, however, when you find yourself crafting the perfect e-mail or Slack response to a question from a client or even a colleague. Or when you spend a day refactoring your own new code without committing any of it, only to come to the conclusion that really, that first version now lost forever really had its benefits.

When in good company, you don’t have to say no to overtime

But there is hope: if you work for an agency, there’s a good chance that you have a guardian angel in the form of a project manager. Whenever you’re unsure, your project manager will remind you what your priorities should be.

Employment will also reduce the risk of perfectionism-inspired overtime: clearly defined office hours make a world of difference. Inpsyde operates 100% remotely and grants its employees with a fair amount of flexibility with regards to when they start, take longer breaks and when they can have their Feierabend. Nevertheless the contract I signed specifically mentions that working late at night – or past midnight – is not okay. Which is the perfect antidote for those of us who, against their own better judgment, cling to romantic notions about doing CSS refinements by moonlight.

Different environments, same old Impostor Syndrome?

Just to make something clear: I could have linked most of the ‘symptoms’ mentioned above to (a very mild form of) impostor syndrome (or imposter syndrome), an affliction famously connected to software development professionals. It was a veritable a-ha experience when a programmer-friend/colleague told me that Impostor syndrome was a thing: suddenly, I had a label for the recurring thought that this whole ‘business’ of mine was, in reality, a shabbily executed dramatic solo performance, where I played the role of an entrepreneur dressed in a cheap costume made out of a VAT number and a domain name.

When you’re a typical freelancer, working alone, almost all of your feedback comes from clients. And yes, the client is Always Right, but you know that there is an exception to this rule: when your client compliments you on your technical skills. Because surely, in reality2, the client has No Idea. This is, after all, the foundation of your entire business model. You were only able to sell your services because your client does not know about certain WordPress plugins and modifying existing themes through a child theme. You won the pitch, simply because the client does not know any real developers.

So does this get any better when you’re working for an agency?

Yes and no.

Especially when you’re new to the job, it is easy to be intimidated when you have highly experienced, very talented colleagues who use the company-wide dev-channel on Slack to casually discuss PHP principles at an abstraction level that makes your head spin. In that sense, you run the risk of isolating yourself in a way that may feel familiar. At least in my case, one of the side-effects of freelancing was that I would often feel very lonely.3 Especially when faced with a difficult programming challenge, I was afraid to ‘expose’ my own ignorance on WordPress Stack Exchange, so I rarely discussed the problems I had with Actual People. If you notice that this is an issue, tackle it. Because this problem will not leave the minute you join a team.

How to handle your Impostor Syndrome when Working for an Agency

One thing is very important to keep in mind. If an agency hired you as a developer, there’s a good chance that you did a code test and that you performed well. You got hired for a reason, and it’s not (just) your friendly smile. Or your immaculate CV. Or the sweeping argumentation for hiring you that you brought forward in your cover letter. And it’s also not that Oscar-Winning performance during your first interview. You have skills. Actual People have looked at your work and yes, they may say that it needs improvement. But the fact that the agency hired you means that they have faith in you and your abilities.

Luckily, working in an agency means that you have direct colleagues who will not only try and help you whenever you’re stuck, they will usually help you realize that they too get stuck sometimes and forget how things work. In the end, what matters is that the feature gets shipped or the bug gets squashed. The client does not care whether you solved it all by yourself, and neither should you.

Income (in)security

I have no doubt that it is possible to rake in heaps of money as a software consultant. I am not sure how many of those consultants operate in the WordPress world (or ‘sphere’ or ‘game’ or ‘scene’ or whatever you want to call it). But I think that, considering the nature of both the developer community and the target audience, it is safe to assume that the real money-raking happens elsewhere – at least when it comes to freelancers. That said, there are some really successful one-person WordPress operations. They usually focus on a product – with ACF being a mind-blowing example.

If, however, you are anything like me, you’re an overly friendly, moderately skilled developer who has spent several years as a jack-of-all-trades, master-of-none service provider, delivering and maintaining tiny-to-small-sized websites for cultural organizations, trying to combine development with design, assisting with content editing and general WordPress support, even dabbling with server administration and hosting, this means that the money isn’t always great. Yes, the freedom that comes with it is ‘worth’ something, but in my case, a tremendous weight (read: a debt-fed dragon smelling suspiciously like instant noodles) fell off my shoulders when I received my first salary and realized that the exact same amount would be deposited in my account one month after.

So to maintain the rhythm of the previous sections let’s just answer the question once more. Does this change when you move to an agency?


Simply put, if you were struggling with income security as a freelancer, employment is going to get rid of that for you. Unless, of course, you accidentally applied for a job with a startup that disrupts your paycheck by cutting it in half and paying the other half in equity, fresh fruit and a flat-white flat-fee. Admittedly, if you were a freelancer before, this is a very unlikely scenario, and at this point I’m going to assume that maybe the income thing is not your priority anyway. I dig it, I was an Erasmus student once, too.

But wait, there is more: you can combine income security and flexibility by working remotely, you say?

Furthermore, when your employer allows you to work remotely, wink wink, nudge nudge, this newfound income security does not even have to cost you your freedom of movement since you’re not bound to an office in a particular city. As I learned from my esteemed colleague Giuseppe a few weeks back, remote work is pretty much the standard among the more important WordPress agencies. So finding a remote job as a WordPress-anything might not be as difficult as you think. As mentioned before, remote work is not without its risks and it is not for everyone, but if you are considering a switch, remote work might very well be the easiest kind of employment to adjust to. Sort of like a gateway drug.4


So there it is. Needless to say, these thoughts, considerations and even some of the embellishments are based on my personal experiences. Still, I hope that you have found some of the above either entertaining or useful. Or both. And just to make sure that you don’t leave this place with some hot takes, here are some hot takes5:

  • read about Wabi-sabi
  • if you’re not sure if employment is your thing, simply start by applying for a job. Then see what happens in the interview. If you don’t feel comfortable going in, you don’t have to take the job. And if you do, they ask you about your experiences in those first few months. There you have room to provide feedback and say what you need.
  • asking questions is difficult for you? maybe you can force yourself to ask one question per day to learn it.
  • be as specific as possible in your own tickets. Define sub-tasks so you are not tempted to do all the things you can think of. In other cases, maybe you can ask your PM to be *more* specific if you feel that vagueness often leads to ‘doing all the things’
  • be as open as you can with your team-mates, so that they know what’s going on (this is vital when you’re working remotely)

1 Yes, I went there and if we’re lucky, this darling survives later editing. Fingers crossed everybody!

2 Note that I am repeatedly (and, arguably, somewhat pretentiously) turning on its head that which we usually mean when we say ‘in reality’

3 In early drafts of this blog post, loneliness was to be Perfectionism’s third friend, under the alias of Isolation for alliterative purposes only. Arguably a relevant theme in freelancing as well as in remote work. I hope I can follow up on it since it is a topic close to my heart.

4 Did you notice how Inpsyde’s logo is a green leaf? A coincidence of course, so let’s just attribute this footnote to my having lived in Amsterdam for fourteen years.

5 Hot takes means ‘tips’, I think. I heard it on a podcast. That said, I’m pretty sure that some of these takes are lukewarm, at best.

* Many thanks to Shridhar Gupta for the photo we are using in this blogpost header.