Leveraging Holistic Synergies

The Lie Freelancers Believe

Let's try something more exciting, like Comic Sans. And make it "pop".

There's a trope among freelancers that when something goes wrong with a client its because we're working with a "client from hell". The type of client who wants free work, a lower rate, who wants to butt in and micromanage everything, or overall is just a plain jerk.

Hell, you've probably even seen the eponymous website.

And sometimes - sometimes - this happens.

But most of the time it's not the case that you're dealing with a client from hell. The client from hell does exist, but most often acts as a mythical archetype to hide how we've selected our clients and managed relationships.

It's fun to commiserate with other freelancers just like it's fun to share successes, but you'll get more control over your business, your life, and your happiness if you stop kvetching and start taking responsibility.

The making of a sad

Let's start with a short list of things that clients do to freelancers that make us sad:

And this is not an exhaustive list!

Client from hell?

An obvious mistake I see freelancers make is uncharitably interpreting communications from clients. And yeah, I'm counting me too.

It can start as simply the client sending a terse email - and suddenly they're a terrible person.

"Wow, I can't believe they never write 'thanks' in their emails"

"ok"? Just "okay"?

What if - what if - they're just having a bad day? Or what if they misinterpreted something you wrote? Empathy is important for communication, being able to get into someone else's head and trying to understand where they're coming from so that you can plant into their head the idea you have.

This means considering the various possibilities for that persons's actions, rather than distilling down to your first reaction and projecting what you would think in their shoes. Instead try the most charitable interpretation to start.

Yeah I'm quoting my own tweet, sue me.

In practice what this means is be a little bit more understanding when someone says something to you that isn't obviously "bad" and be more careful yourself in communicating such that you leave little ambiguity in how what you say could be interpreted.

Never attribute to malice that which is adequately explained by stupidity

Let's be charitable and substitute ignorance - in all of its objective meaning - for stupidity. Did your client really know your payment terms? Did they know just exactly what kind of feedback you needed and why? Did they understand the specific goals you were working toward?

When you spend all your time on one side of the table it's very easy to lose sight of how the other side sees things. They don't have the answers you have about how things should work until you communicate these. And moreover, they're bringing their own expectations, often based on prior experiences with consultants and freelancers, which you may have to disabuse them of.

Of course this doesn't address malice, which you have no obligation to tolerate. But in my experience and that which I've been able to observe close up, malicious intent, and even outright callousness, is the exception.

Relationship triage

Let's assume you have a subpar client relationship, where malice is not the issue. You have two choices:

  1. Fix it
  2. Move on

In fact, these are your choices with any relationship that's not working out for you, business or personal. Whether you can "work it out" depends a lot on the nature of the problem and how both you and the client see it.

How do you fix it?

Upgrading a client relationship

A few strategies to consider:

Processes can help fix smaller problems, especially around payment - if you stick to them. Set up automatic billing reminders, require payment or at least a deposit up front, and stop doing work for the client until you're paid for work-to-date.

The communication one is a bit trickier, but it comes down to this: if you sound like a professional you're more likely to be treated like one. That doesn't mean you can't use emojis in your emails, but it does mean be confident, be clear, and address the client's needs.

The third option is the hardest but for all non-trivial issues this is what you need to do. Write down what you see as the problems and some possible solutions before this conversation. Don't enter the conversation without having given it some thought and allowing the client to do the same.

I'll give one strong word of advice here as a disclaimer: if someone is abusive, whether in a business or personal relationship, skip option 1 and go straight to "move on" as soon as possible. It is entirely possible that this person can change for the better, but that's not your responsibility. If a client belittles you or threatens to withhold payment unless you do something more, it's time to fire that client.

Saying 'adios'

There are a few ways to leave a client, and which strategy you take will depend on your tolerance for working with/communicating with the client and what's going on in the relationship.

One strategy that gives you optionality is to raise your prices - if and only if you really would continue working with the client at the rate you suggest. This will backfire if that's not the case! It's normal to raise your prices as your expertise and marketability increase, but this represents a significantly higher increase.

If you think they're good people who, for whatever reason, you can't work with anymore, explain to them to the greatest degree that you're comfortable why you're moving on. And offer a transition plan, including wrapping up any outstanding projects and documenting any processes they may need. Unless you're working away because they don't have their stuff together this is a great opportunity to refer them to someone else in your network.

Now if this is truly a bad client for you, send them an email letting them go. Never get personal under any circumstances. Just tell them it's clear you're not a good fit and wish them the best of luck in their endeavors. There are some good guides out there on how to approach this particularly tricky situation. But keep it short and don't engage in a why conversation.


Ideally you don't have to deal with these kind of client relationships. You may run into random jerks but you can select against these problems by taking responsibility for them.

Avoiding client projects requires a two-pronged approach in both client selection and expectations setting.

Be explicit from day one

This is from a cheese steak shop in Philadelphia (PA, US).

Why does a sandwich shop have such stringent and written expectations of their customers? Because when customers follow the process this grossly simplifies the work they have to do in quickly turning around orders and by making the rules written customers know up front what the process is.

Pat's King of Steaks

Do you want to know who fucks with these rules?

I'll tell you who: people who go home hungry.

Originally published 2018-12-05