Do your clients actually want you to succeed?
A freelancer’s litmus test for durable, mutually beneficial relationships
What does your dream freelance client look like?
Fast payer. Steady stream of high-profile projects. Positive feedback. Referrals galore. Responsive and easy to work with.
Sounds great.
But after 27 years of running my own business, I’ve found one question that cuts through the noise:
Does my client want me to succeed as a freelancer?
Obviously, that’s the sum of all parts rather than one piece of the freelancer–client relationship. And it’s often easiest to see in conflicting behaviors, such as a client who:
Pays well, but is consistently negative/nudgy/panicky
Is a blast to work with, but tends to be cheap
Provides endless referrals, but 50% are clients from hell
Hooks you up with fantastic projects, then bogs you down in bureaucracy
Mix and match your own examples, and you’ll recognize how the negative traits often drag you down more than the positive ones boost you up. Succeeding in a freelance business isn’t just about how much the client pays you.
Tell Me the Client, and I’ll Tell You Who Sold Them
My final corporate editorial job was at a custom magazine publisher with a client base of hundreds of hospitals, banks, and luxury brands, etc. We had a dozen salespeople, and the behavior of each client was directly related to whoever sold the contract.
Matt’s clients were businesslike and solid communicators.
If Todd cut the deal, they’d be nice but scatterbrained, and late on deadlines.
And if Andy sold them, you could count on them being a constant pain in the butt.
The editorial staff had no say in assignments. The clients paid big bucks, the salespeople made big bucks, and we needed to make it work. They cared about their own success. Ours? Yeah, right.
Succeeding Over the Long Haul, Client by Client
As freelancers, we’re selling ourselves every day. If you tell me who your clients are, I can tell you who you are. We actively choose, with every day and every project, how we spend our time and effort.
Over time, your success will depend on securing projects you enjoy working on, with people who respect and pay you appropriately. Anything short of that, and it’s going to be a problem. A few quick action steps that can help:
Run a quick audit on your current clients: List green flags (mutual respect, fair pay, interesting projects, clear communications, etc.) vs. red flags (scope creep/endless revisions, slow/late payer, energy drain, etc.). Do the pros outweigh the cons? Have you addressed the red flags? Are they even fixable?
Re-examine your positioning: If you keep attracting clients who give you headaches, what are the possible root causes? (e.g., website, pricing, proposals/contracts, lack of boundaries.)
Don’t feel guilty about saying no: Politely parting ways with prospects and clients who aren’t a good fit frees up time for the right ones.
Sure, there are sheep-clothed wolves out there, but if you’re getting burned on a regular basis, something is awry with your strategy, not just the prospects and clients themselves.
If you tell me who your clients are, I can tell you who you are.
As for me, I work best with people and businesses who include me as an essential teammate. It’s nice when they express appreciation, but they don’t even have to say out loud that they value my success, because there are a thousand indicators in how they act. In turn, the feeling of a mutually beneficial relationship isn’t the only reason I want to help them succeed, but it sure helps.
In the comments:
What are the client qualities that indicate to you they want you to succeed?
What’s your biggest red or green flag?
Tag a freelancer who needs to hear this.



