How to Stop Being a Stupid Freelancer


Nearly half the time, when I begin to interact with a prospective client, I learn that she’s had a bad experience with designers (or developers) in the past. Sometimes this history manifests itself as an honest disclosure, sometimes in a dominant communication style and apparent lack of trust out of the gate, sometimes just in learned habits to check in constantly and see if I’m “on track.” It makes sense; she is eager to detect any red flags she may have missed in the past, or avoid going down that road at all costs.

So I have to ask, What in God’s name are you doing to your clients, Other Freelancers? Beyond just the normal Life-Happens-Deadlines-Shift type of stuff, I’ve heard some real horror stories of Freelancers From Hell. In fact, I’ve experienced them firsthand when I’ve subcontracted out work to other designers, even ones I’d consider friends. It’s absolutely maddening, and totally unnecessary.

Real quick, though. A general, blanket disclaimer: I’m not perfect. You know, obviously. I struggle with my work occasionally (usually). Things happen. Ideas sometimes take longer and cost more. Building a website with a stranger on the other side of the country can be one long, complicated trust fall. We do our best to move, adapt and cross the finish line strong and on time. But things happen. They always do. I’m simply here to offer a few guidelines and suggestions for avoiding the avoidable, and managing the manageable.

But let’s get to it. Here are a few tips and guidelines—for pleasing clients, keeping productive, and enjoying your work from bidding to launch. 


On Clients

Write back soon

Do whatever you have to do–a system of post-its, iOS reminders, contact management software, writing on your hand–to follow up with your clients in a timely manner. Even just to say, “Oh, hey! I got your message. I’m definitely going to unpack it tomorrow and get back to you with a complete reply.” (And then actually do it). Prospective and current clients often judge you by this more than the quality of your work. They don’t always know about design, but they do know about customer service. So, give them both.

Schedule honestly, and reasonably

If you don’t already, start tracking how long it takes you to get things done. Give yourself the time it takes to get it done. And then, finally, get it done. (It’s honestly that simple. You’ll be more profitable this way, too.) If you’re constantly short on money and time, and always apologizing to clients and moving things around, it’s not working. Make it work. Or do something else.

Also, avoid taking that famous Friday stay of execution and eagerly promising you’ll have it to them by Monday. Your Monday self hates you already. You’re not being realistic. You’re being excited to get an extension of any kind. This will always, always come back to haunt you.

Over-promising from a place of despair (like saying, “Dear God, if you just get me out of this, I’ll go to church every Sunday for the rest of my life!”), and then failing to meet the extended deadline is 10 out of 10 times worse than a designer who checks in early to ask for an extension, asks for enough of an extension to get it done properly, explains the challenges and proposed solutions, and then meets or exceeds it.

Put another way, if you’re on a plane, waiting on the runway, which pilot do you appreciate–the one who says, “it’ll be about a half an hour” over and over, or the one who checks in, gives you information about the delay, and maybe even honestly says, “I don’t know how long we’ll be here, but I’ll let you know as soon as I have any information” and then checks back in with you at regular intervals. Which one calms you, and which one makes you want to freak out and flip soda carts?


On the Creative Process / Time Management

Avoiding the Oh Shit! moment

There’s something that happens somewhere between hoping you win a project, the excitement of winning a project, and the oh-shit moment of actually having to do it. That’s a shame, a waste of a cool opportunity, and a sign that your process is broken somewhere. It’s really important, and loads more fun, to carry that feeling of excitement from the bidding phase to the launch phase. (If you never have that, I’d suggest, you know, taking a bigger look at what you’re doing and why, I suppose).

Keep momentum

Momentum is the key to success and the meaning of life.
This is a big one for me. If you have a project that’s vast and overwhelming, you’ll be tempted to find yourself putting it off, dreading it instead of daydreaming about it, only to ultimately sit before a blank, white screen two nights before it’s due. The moment you get behind, The Project becomes your arch-nemesis. The nagging jerk waiting for you while you’re with your family on weekends, while you’re trying to fall asleep at night, while you’re driving down the road singing Justin Bieber songs like any normal person.

So? Stop getting behind, duh. Plan well, and keep moving. Always be moving.

It can be as simple as creating the Photoshop or Illustrator document right away with the proper specifications, setting up your guides, saving the file and creating your file structure to organize your project files. Keep the file(s) open. Work on it a little bit at a time. Glance at the work as you pass by it on your way to fix dinner. You’ll notice something with fresh eyes and can give it the nudge it needs. Create the file, keep it open, keep it moving. Goes a long-ass way, I’m telling you. Give yourself enough time, enough whitespace, and move forward each day. Like I always say, a journey of a thousand steps is a pain in the ass to complete in a weekend.

Make lists

If it crosses your mind in the work zone, write it down, and leave it behind. I’m not fancy with the note-taking; I just use the Notes app on my Mac/iPhone/iPad to do a daily brain dump and to do list. I’ve tried Evernote, ToDoist, TeuxDeux, and so on, but the simplicity of Notes just works for me. No features. No barrier to entry.

Anyway. I believe your brain needs to be clear to do good work. Clear it up. Keep your desk, your desktop, and your mind free of clutter. Keep your layers organized and appropriately named. Clutter is where ideas go to die. And if that’s not true for you, well you’re a magic little human and I want to speak more with you later.

Every little thing you need to do, write, say, or remember–it should leave your brain immediately and live in a list until you’re ready to deal with it. Period.

Disconnect completely

Turn off social media. Turn off your wifi. Go somewhere people can see your screen
If you struggle with time wasters, the siren song of someone putting off a scary mountain of tedious work, do one or all of these things to babysit yourself:

  1. Set a time limit, and then hustle to meet it like you’ve got a plane to catch.
  2. Leave your laptop unplugged and then race yourself to finish it before you run out of battery.
  3. I’ll sometimes use an app to block certain sites or just straight up turn off my wifi (or at least set my iMessage app to do not disturb in the notifications panel).
  4. Sometimes, when I’m working on something I’m really dragging on, I’ll go to a coffee shop or coworking space and just plow through it. Something about working around others can keep you really aware of and honest about your focus and tasks.

Deal with your issues

Building a website is a marathon. One I insist on running back-to-back-to-back like a complete psycho.
I honestly love the creative part, more so now than ever before, but I truly feel the process of actually making it is a huge bottleneck that I have to carefully manage. Photoshop, specifically, takes the creative energy and excitement I have for a project and convolutes it into a seemingly endless list of tedious production tasks. A real, nasty bummer.

So, after a few too many miserable moments, I now recognize about myself that I have a pretty big “stuck” point about 30% of the way in, just about every time. Say I’ve delivered a brand board and production ready homepage design that I’m obsessed with. The client is excited. We’re moving forward. No one’s asked for Papyrus, or to make anything pop, the logo has not been made bigger, I’ve proposed big changes and gotten everything passed. Things are looking promising.

And then? I actually have to build out the single post template, or whatever, complete with threaded comments and link styles and hovers and I start thinking about the rest of the things I need to design and build and measure and duplicate and streamline and double-check and before long I just want to go into Witness Protection and start life over as a bank teller. The Honeymoon is over. I want to stop. I cannot possibly go on (but totally am contractually required to).

Like a lot of people, I also have a small potential stuck point around the last 5-10% of a project, when all that remains is tying up loose ends, and applying the final fit and finish. But at least in this case, the glowing light of that sweet, sweet finish line is enough to pull me through.

The only cure is momentum. You can’t stop or you’ll die get behind. So, when I need a break from one type of task (tedious), I move to another (brainless, or creative).

Divide your tasks, identify types

When I finish one complete template and can’t muster the strength to immediately create another, I’ll move to a more menial production task like organizing the files in the project folders/subfolders/desktop and make sure everything’s square. I’ll go through the design files I’ve created so far and name the layers, group them into sensible groups, check my guides, grids, and measurements. I’ll make a list of any design elements I need to create along the way, anything I need to circle back on, questions I need to clarify with the client.  Just as long as I’m moving. And, as a result, achieving a greater sense of order and clarity by getting things cleaned up is more encouraging to continue with the heavy design lifting.

There are a few types of tasks in my typical web process. I’ve listed them in order of my enjoyment. Clearly.

  1. Creative, Conceptual (creating the mood board, initial design concepts, first page design; it’s all love and rainbows and butterflies in the belly)
  2. Brainless (naming Photoshop layers, deleting unused objects, organizing file structure, admin stuff in Basecamp like turning a rambling client email into an actionable to-do list; not rocket science but necessary and clearly appealing to the side of me who considers The Container Store a proper vacation; a web design palate cleanser)
  3. Production/Foundation Work (building out page layouts and type hierarchy in Photoshop, creating style guides for development, anything heavy on Photoshop work, low on creative design; makes me want to pout and whine and mop my floors just to avoid it for one more hour because I just cannot)
  4. Horrifyingly Awful, Feet-Dragging Shit™ (site launch details like preparing site documentation with screenshots, recording video walkthroughs of a site, designing complex features that are heavy on UI and low on visual design, manually creating a mobile design by resizing elements from the desktop view, generating assets for retina)

Simply put, the more I hate something, the longer it takes me. That’s my signature move weakness, no two ways about it. So in order to work around my special quirks, rather than let them derail my timeline and budget, or drag me by the hair all the way to Burnout Town, I have to implement a sort of healthy rotation of tasks.

Any web design project is like a well-balanced meal. How you get it all down is up to you, but you find something that works reasonably well. (My design process is not unlike the way I have to manage my child, I should note.)


On Self-Awareness

Design around yourself

All of this to say, if you are a human, there is probably a point where you reliably fall down or get stuck. Recognize it. Allow for it. Plan around it. A couple of ideas for getting unstuck by the thing that sticks you: Hire it out, trick yourself into doing it by making it more fun, invent a process that doesn’t require that part. But don’t fail to note it, and let it derail you or piss off your client.

For example, my ideal project is one in which I get to work with a design-leaning developer who can take over somewhere soon after I’ve got the concept fleshed out, the design language established, some layout and design patterns down, and doesn’t need me to dive deep into the Photoshop mine for every view and inch of a site. We keep momentum, we don’t waste hours or dollars. That doesn’t always happen, though. Not yet. It might become more common in the future, things are always shifting and turning upside-down, but this is where I am today. 100 layers deep in Photoshop.

Before you tell me about Sketch or whatever else, I’ll say that, for me, eliminating Photoshop doesn’t remove all pain points of web design. It just changes them. When I do more of the work in browser, or use a different app, I have new and different pain points I try to work through to keep the momentum. It all comes down to momentum in a marathon. The rest is just details.

When the process is too broken

What if you’ve tried everything above, but routinely find yourself stuck and hitting walls? When your process is so broken, so consistently flawed or stressful, it’s important to look deeper. You might find you’re so far from the place and thing you’re meant to be doing, that your mistakes will be bigger, more frequent, and harder and harder to recover from. If that’s the case, as I know it was for me when I worked at an agency, identify the problem, and deal with it quickly. Get to where you need to be to do what you need to do. The mistakes will only get bigger, your work flatter, and your enjoyment of all of it less and less—you risk burning bridges or losing internet friends, zero fun.

The House of Grays Shelter for Abused and Disillusioned Clients is over capacity. So please be kind to your people, play to your strengths, and plan for your weaknesses. The world needs more people who are doing what they love, but they need even more people who get the job done well and on time.