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  • Writer's pictureTiffany Philippou

Dear Tiff: Should I fire my client?

They're stressing me out, but I feel like I shouldn't walk away from stable income when everything feels so uncertain

This article was originally posted in my newsletter - the Tiff Weekly.

Dear Tiff,

I'm a fellow freelancer and I'm struggling with a difficult client situation.

I've been working with a client for a few months and I'm having some issues. My instinct is to fire them but I'm worried that I don't know if it's a me problem or a them problem.

My main frustration is that they don't give me adequate feedback, despite me repeatedly asking for it. And then inevitably this leads to a problem with the work. In a specific example, the client emailed me on the weekend to tell me off and said we needed a call the following week which really stressed me out because I hate feeling like I'm trouble.

On the other hand, the work brings in decent income and they always pay on time which I can't overstate how rare that is in my industry. I feel like I shouldn't walk away from a stable income right now when everything just feels so uncertain.

I told myself I would do this job temporarily while I take a leap of faith on a creative project. However, I'm concerned that I'm now just procrastinating on actually getting that project off the ground because of the stable income. Maybe I'm looking for reasons to fire them because I'm too scared to walk away in the hopes of something better.

Please help!


A self-doubting freelancer

Dear self-doubting freelancer,

I feel like there’s a part of you that’s written this wanting me to say ‘YES QUIT, you go girl, dance off into the sunset and launch your creative project’. But sorry, no. I’ve noticed there’s an increase in people self-diagnosing as self-sabotaging or procrastinating, probably thanks to the internet. However, these can often be surface-level issues, small talk, even, that can distract us from peeling back the layers of the onion and discovering the far more complex reality of being a human.

Telling you to fire your client now would momentarily make us both feel great and I’d love to give you that dopamine hit, but I’d love it more if you could pay your rent next month and afford your weekly food shop. Unless you have some stashes of cash that will keep you without earning for a while, which I’m guessing isn’t the case, otherwise, you wouldn’t be putting up with clients sending pissy emails on the weekend and mentioning how great it is to be paid on time.

Aside from the financial practicalities, there’s also the unsexy truth that we need a stable foundation to create from. The chaotic, mad artist or creator is a myth. I can only be creative when everything else around me is stable and calm. The last two years have been a major, major struggle in that respect. Before I can create anything meaningful, I need the basics covered: financially, romantically, in my home life and the outside world. We’ve all had these things shaken for us in different ways in recent times and creativity has suffered. So, in service to your creative work, I believe you need to keep everything else around you as secure and stable as possible. So yes, you go girl, launch the damn thing and get that creative project off the ground! Take the pressure off if there is some fear of failure (or fear of success?) going on there by seeing it as a trial and then, yes, fire your client once the project takes off.

And yes possibly, possibly, you’re using this job as a distraction because you’re nervous about launching the project. But my instinct is telling me there’s more going on here. I think what I’m seeing is the work relationship equivalent of when things get difficult and you have to deal with someone else’s shit (which in a work context often plays out as incompetence) and your impulse is to walk away. There’s a reason you’re freelancing. Yes, I’m sure it’s partly that you’re mega creative, but there’s also a part of you that can’t have a job. Possibly you can’t handle the emotional turmoil or being told what to do (this is me). Or the worst thing of them all about having a job - the fear of being told off.

Join the club, by the way. As my friends can get things like mortgages and are reaping the rewards of a consistent salary for over a decade, I’m still in lumpy income city with no idea how much I’m going to get paid month to month. AND now salaried people get to enjoy many of the perks of freelance life - working from home! So I’m often asking, what’s the point? Why am I doing this? I often wish I was the personality type who could just have a job. Because freelancing is hard. You’re constantly taking on new clients or work and having to form these new relationships and learn other people’s idiosyncrasies. Also, the reality of modern work and the way it’s set up is a total shit show and so I’m not surprised that you find yourself working with someone who a) doesn’t have the skills or ability to give you feedback and b) sends you emails on the weekend which are written in a way that makes you feel anxious.

I don’t think they intentionally wanted to cause you anxiety, it’s far more likely the problem here is poor phrasing. In fact, most people can’t write emails. Email sucks. Slack is even worse. People need to speak to each other more. Scheduling calls is tiresome, people should just make quick phone calls or I’ve started sending work VMs which is the best of both worlds. But anyway, I’m before my time.

When people start freelancing I have one piece of advice: fire clients fast. And I stand by this and I actually think you should still walk away from this arrangement. But not because of them or the situation, but because all freelance clients who serve as the backdrop of your creative work should be temporary.

I’ve learnt this through getting it very wrong myself. I used to do long term projects with startups and get deeper and deeper into a company. One time, before I knew it, I was in the office five days a week and presenting to their board and then one day I work up and realised I hadn’t written anything in months and I had to leave.

Since then, I am RUTHLESS about client work. I am very project-based, very clear on the scope and very boundaried in my communication. I also move on quickly if it becomes apparent that it’s not going to work. I’m often working with clients on a commission basis, rather than being paid for my time, which is not for the faint-hearted, but forces me to be very practical about the relationship.

The problem with your current situation is that you’re getting irritated, you’re getting sucked in. It’s a sign that it’s time to plan to leave! However, my advice is to launch the creative project first. So now it becomes a question of how you can tolerate your situation in the meantime. How to not let it drain you and steal the energy you need for your true purpose in life, which is to share your creativity in the world, NOT to think about how best to reply to poorly phrased emails.

You seem like someone who’s interested in growth and learning and holds high standards for themselves. It’s why you’re frustrated by the lack of feedback and why you’re really writing to me - there’s a deeper part of you that is aware that there’s something going on here.

I’m going to presume the client work you’re doing is pedalling your craft to an extent and so it’s important to you that you do it well. But! I think you need to divorce yourself from it a bit. Hold an awareness that you are the sort of person who cares about doing a job well, which is great, but your identity and worth isn’t tied up with how well you perform within the commercial constraints you’re operating in. You’re not doing your craft in optimum conditions or context. Save your worth for that creative project that is purely yours.

You’ve literally articulated the worst thing about work - an afflicting that we carry into our thirties and possibly beyond: the fear of being told off. I’m not a therapist, but we’re all traumatised from childhood, where for many of us, getting ‘told off’ was scary ASF. It also wasn’t necessarily the telling off itself that was the problem, but the confusion that came with it. We rarely intentionally do something wrong and so when we’re met with a telling off, it takes us to a horrible place of being misunderstood. My main memories of primary school are teachers YELLING at me and I didn’t understand what I’d done wrong. Or I sometimes did eventually get it, but hadn’t intended to cause trouble.

In your work, I’m sure you had the intention to do your best, so when you’re met with something that feels like a telling off, then it’s really horrible. Really, really horrible. Especially on a bloody weekend.

Let’s talk about this email from your client. Practical note first, please set up a different email address for your clients and turn it off on the weekend. Train them to use the new email by not replying to them if they email you at the old one.

It’s very rude in the era of ‘schedule send’ (where you can write emails and schedule them to automatically send at better times) to send emails to someone who’s working for you on the weekend. Emailing a subordinate on the weekend communicates to me three possible things:

1) you don’t know how to use schedule send

2) you have poor time management so have to email on the weekends (or maybe you don’t have anything better to do, but we live in the era of Netflix as well as schedule send, so…)

3) THE WORST - you WANT people to know you’re working on the weekend.

So let’s presume based on that email that you’re dealing with someone who’s a bit incompetent. They don’t know how to give feedback and they don’t think about how their email lands with you. That’s fine to suggest a call, but to suggest it alongside a negative comment and to allow it to be read in a way that implies that the call is going to be negative is not good.

This is the problem with work. Everyone spreads passive-aggressive anxiety around via email and it’s just not nice for anybody.

You also shouldn’t be in a situation where you’re ‘asked for a call’, there should just be a regular check-in call scheduled. I find less experienced people shy away from the phone more, whereas more senior people know how important it is to set that up. A weekly check-in is something you should push for when you take on new clients. It also forces your work to be a priority for them so they give the time that’s needed to give you feedback and to flourish.

This person isn’t giving you feedback because they want you to fail or they want to tell you off, they probably just don’t know how to give feedback. Good feedback is an art form, which most people don’t have a clue how to do. Another problem with work.

You need to step out of the employee mindset and into the mindset of the hired expert. Freelancers are often hired as experts and have more experience in our field than those managing us and we need the relationship to reflect this. We need to teach them how to best support us. We need to show them what good feedback looks like and why it’s important. We need to see ourselves as strategic advisors. When something isn’t working, we need to discuss as a team why we think it isn’t. If I’m struggling to get good candidates for recruitment, it could be that the salary on offer is too low. If we’re not getting PR for the client, it could be because the company is boring. If the copy isn’t liked, it could be the brief isn’t clear. I could go on. This is the energy you need to bring to the REGULAR calls. If they’re still choosing to blame you and to not be collaborative then yes, fire them. Instantly and quickly.

But I think that fear of getting into trouble thing is never going to go away and neither is the need for a stable income in an uncertain world. So I think sticking this out for a bit and getting some exposure therapy to the pains of working with people could be a growth opportunity. Now get back to that creative project.

With love,

Tiff x


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