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  • Caroline Ridgway

The Difficult Client Versus Hopes and Dreams

Updated: Apr 23


There’s that feeling you get when someone says you to, the self-employed person, gee, it must be so nice getting to be your own boss. And you know, deep in your soul, that the reality is more like having as many bosses as you have clients, except that there’s no connection or coordination among them, and each believes that their needs are at the top of your priority list. And part of you badly wants to accommodate that daydream, artfully sculpting your work day so that every little task is tended to. The further reality is that owning your own company is an exercise in mostly minor-scale crisis management. There is no routine. There are no two days that look like. It is getting the work done nights and weekends because that’s when the emails and meetings subside. It’s never going on vacation without your laptop in tow.

And amid the chaos and the desire to please and the appreciation for solid home wifi, there is the eternal question of how to best support The Difficult Client. You know the one. How do you manage the client whose expectations are so out of step with reality, and whose mode of communication seems to be largely grounded in condescension, and whose first word as a child many decades ago was probably “no”? How do you nurture your own self-confidence on the days when you find yourself speculating, maybe I am a failure? Asking for a friend.

I could give you some practical advice, like never respond right away to an email that feels inflammatory. Best to let it sit for a bit first, to allow your emotions to settle. Sometimes, I dare say, no response at all is the most productive approach. Sure, it’s about being responsive to your client. But your own self-preservation has to be on the priority list, as well.

If a specific complaint is levied, you can ask yourself, did I do everything I could in service of this expectation? Relatedly, were our expectations about this potential outcome aligned? Do I feel that I, in good faith, did my best? If the answer is at all no, then perhaps your approach needs to be modified. If yes, then give yourself credit where it’s due. In all cases, be transparent, and be courteous, but also be protective of your boundaries.

A tougher course to navigate is the potential of a fundamental mismatch in communication styles, or even personalities. Here’s where you need to do a personal gut check, and weigh the relative price of retaining the business versus staying true to your own sanity, or morals, or ability to honor the rest of your business if your attention is too divided. How do you know when to cut the cord? Firing a client is never an easy prospect. You can feel respect for them as an individual person, or for their business, and still conclude the professional match isn’t there. And, let’s be honest, making the decision to reduce your income is frightening. Here’s where I give myself advice: try to trust that the universe will provide. Client relationships end. Others will take their place.

Dare to have the hard conversations with yourself about what is too much. That could be an over-commitment of time that needs to be rebalanced. It could be the determination that, try as you might, there’s simply too much of a divide between what they want and what you can deliver. It can be a realization that, somewhere deep inside, your intuition is telling you to move on. Maybe one of these days it is because you’ve slogged and endeavored and now your business is sufficiently self-sustaining that you get the exceptional good fortune to be able to select your clients based on your passions and values. May we all get to that point.

In the meantime, when The Difficult Client has you questioning not just your talents but your very worth as a person, here’s to deep breathing exercises, friends to whom you can openly vent your frustrations, and the scraps of hopes and dreams that got you into this mess of being your own boss in the first place.


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