The Tightrope Act of Freelancing: Doing What Clients Ask vs. Doing What Would Be Best

Jim Dee
Jim Dee
Jul 20, 2020 · 5 min read

“Soon we must all face the choice between what is right and what is easy.” ~Albus Dumbledore.

This article discusses a problem that many freelancers face. While it uses web design as the context, I would invite readers to mentally replace web design/web development with whatever their service niche happens to be.

While many clients come to my company in need of a completely new web site (my favorite type of client, truth be told), quite a lot of clients I’ve encountered as a web developer fall into two additional, and really giant, categories:

In either case, I’m very happy to help. But, with these types of clients, there is usually something I tend to leave unsaid, yet which may be fairly important. In all of these cases, you’re not asking me (as a web designer / web developer) for an opinion on your web site’s design, structure, or functionality.

If I’m fixing something, adding something, or implementing a design of yours (not my own), then I tend to focus on those tasks alone, because that’s what you’ve asked me to do. I mean, sure, I try to do them in a way that looks good and functions as intended. But, it may not (and often does not) reflect what I’m seeing as best practices in terms of design or functionality in the grand scheme of things.

The Tight Rope

Web developers have to walk this tightrope daily. Do we do what the client requests, or do we push back and try to convince them to do what’s right? (Or, is it somewhere in the middle: Do we say, “What you want is fine, and I’ll do it, but that’s not necessarily the best way.”)

The answer can, and does, vary from client to client, and from web developer to web developer. You see, many clients have a strong vision for what they want, and nearly all of them have their own sense of design. After all, they know their business and industry better than the developer in nearly all cases, as well. So, it can be a tough sell for a developer to change their mind about a given approach, no matter how clear it may be to the developer.

On the developer side, proposing a completely different design or approach for clients like these (clients with existing sites and/or their own designs) can come off as self-serving. After all, if a client has a (possibly not well-done site) and wants new functionality, and you’re pitching a complete redesign that’s going to cost thousands (sometimes tens of thousands) more to realize, well, that can get awkward and can create a kind of resentment.

On the other hand, if you don’t say what you think, as a professional web designer / developer, and the site is ultimately unsatisfactory, chances are some other web designer will eventually convince them that they need to redo the site. And guess what? It ain’t gonna be you who does it; it’ll be that developer instead.

You’re kind of damned if you do, damned if you don’t. So, I don’t really have a perfect solution (though, in fairness to myself, I’ve gotten better at communicating this over the years).

It Does Happen (Though, Thankfully, It’s Rare)

I’m writing this today because it happened to me *today*, just now! I was going down my list of software updates to do on my client sites and, when I got to a certain one, it auto-forwarded to a new domain and a completely new, completely different web site. A complete surprise!

It looked good, too — cleaner, simpler, and clearly better design-wise than the one I’d done for them barely a year ago. But, thinking back on it, the site I’d done for them was absolutely 100% their design. They literally drew it out for me on paper with a highly specific list of specs, which I dutifully implemented without much push-back. (What am I going to say when they’ve designed the whole thing already? A good way to lose a job would be to say, “Wow, Bob, that’s awesome that you’ve designed your company’s site. But, it could be so much better if we did it differently.”)

In truth, that client never wanted my opinion on the overall design, and so I never gave it to them, aside from various routine topics that would come up during the development process. But those were more like, “What looks better, a 2-point orange line or a 1-point one? Center this thing, or left-justify it?” In other words, they’d ask me for opinions on aspects of their design, but not on the overall approach.

And so… Yeah, I guess they weren’t happy in the end. And I lost a client over it — a fairly long-term client, too.

My Responsibility

As much as I rationalize / justify my case here and distance myself from any responsibility, there’s clearly a lesson it it for me, even after doing fairly well in the web design business for a decade now. I’ve learned related lessons in the past, too. But here, the lesson seems to be that you can’t, and shouldn’t, hold back on pitching complete overhauls, especially when you know something is less than optimal.

In the end, I knew what they’d done last year wasn’t objectively great. I never especially liked the design myself, as it just wasn’t slick enough. I guess I just held back because it was what they wanted, and I didn’t want to come off as negative about it. Still, unless both you and the client are absolutely super-proud of a piece of work, perhaps that means that it’s not going to stand the test of time, and that maybe you should find a way to say something about it.

So, I’m going to try to consciously do that more — diplomatically, of course, and without being hard-sell about it — and see how it goes. It can’t get any worse than losing the client, anyway, which is what happened here.

✍🏻 Jim Dee maintains three blogs — Hawthorne Crow, Web Designer | Web Developer Magazine, and Wonderful Words, Defined — and contributes to various Medium pubs. Connect at, Amazon, FB, Twitter, Instagram, LinkedIn, Medium, or Jim [at] His latest screwball literary novel, CHROO, is a guaranteed good time.

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Jim Dee

Written by

Jim Dee

Web guy at; author of books & blogs. See:

Web Designer / Web Developer Magazine

WDWD Magazine features articles on web site design / development, internet marketing, social media, SEO, and topics like marketing, communications, business development, etc. Editor: Jim Dee of Array Web Development —

Jim Dee

Written by

Jim Dee

Web guy at; author of books & blogs. See:

Web Designer / Web Developer Magazine

WDWD Magazine features articles on web site design / development, internet marketing, social media, SEO, and topics like marketing, communications, business development, etc. Editor: Jim Dee of Array Web Development —

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