Advice from someone who’s totally winging it

By Published On: May 21, 202314.4 min read

***originally posted on on July 9, 2015***

Some common sense tips for newly hatched graphic designers

I should start with a disclaimer: I suck at taking advice. I’m stubborn and independent and have this annoying tendency to prefer to do everything the hard way. For the most part, it’s worked out just fine and I tend to make good decisions. And when I don’t—well, I’m clever enough to learn from my mistakes (broken bones can be quite the motivator).

So as a human being who rarely solicits advice from anyone, I am constantly surprised by the frequency at which people come to me looking for advice. Somehow in the three years that I’ve been freelancing, I’ve managed to give the impression that I have a clue what I’m doing. Fascinating! So rather than dole out advice one email at time, I was encouraged by a friend to put this seemingly common sense advice out on the internet where everyone can publicly declare how silly and misinformed I actually am. Sounds great, let’s do it!

Figure out what success looks like for you.

Years ago when I decided to go freelance, I was on the usual agency designer career path: Junior > Senior > Art Director > Creative Director. I was a senior with no interest in being Art Director or Creative Director. I really liked putting my head down and designing. I wasn’t interested in managing other people, or directing someone else’s design. On the flip side, I was also a little tired of being micro-managed. Here I was a capable designer doing good work and keeping clients happy, but I found myself constantly struggling to stroke the ego of someone above me—always a man, in case you were wondering—but that’s a whole different article.

I needed a change. I decided that for me success wasn’t going to be found in a creative director salary, or a team of people I got to yell at whenever my boss yelled at me. To me success looked like working a reasonable amount of hours, getting paid for every hour I worked, and doing good work with good people (and having a say in who those people are). I wasn’t getting enough of those things in an agency. I also had no desire to make a big name for myself, to see my designs on national campaigns. I’ve always been far more content out of the limelight, so while others strove for fame and notoriety, I craved quiet and anonymity.

My point is this: it’s very hard to “achieve success” if you have no idea what success looks like for you. Figure out what it is and align your actions with that goal. And guess what—it’s okay if you don’t want to be a creative director. Don’t let other people tell you that success is strictly being at the top—I’ve seen firsthand how miserable a person at the top can end up.

Do good work.

Well, yeah, DUH. Sometimes new designers email me in exasperation asking what my secret formula to getting work is, and they’ll send me a link to their portfolio. Many of these portfolios are not strong. To be fair, when you’ve just finished school you’re still finding your style and figuring out best practices, so I wouldn’t necessarily expect a really polished portfolio. But it’s important to be able to identify your strengths and weaknesses, and be committed to working at improving. Some people have a hard time even assessing the quality of their own work. My advice? Look at tons of design. On Pinterest, on Tumblr, design magazines—wherever you can get your hands on it. The only way to figure out where you fall in the vast continuum of design skill is to see what the best looks like.

If your portfolio doesn’t currently have “good work” in it, or the kind of work you want to be doing, then make up projects. Make up logos, brochures, branding packages, websites, packaging, etc. Make sure you write creative briefs to work from— if you’re going to do it, do it right—act like it’s work you’re doing for a client. Practice areas that you’re weaker in—we have a tendency to work at the things we’re already good at because we’re guaranteed good results. You won’t grow as a designer unless you work on your weaknesses. Design is a trade, and just like any other trade, you need to practice and gain experience in order to improve. Ask for critiques from someone you admire, and don’t take criticism personally (I know—easier said than done). And if you’re lucky enough to get hired on at an agency right out of school, learn everything you possibly can from the people around you. Learn how the business works, learn how to do production on your own files, go to press checks, sit in on client meetings. Much of my success as a freelancer can be attributed to the learning I did working in studios.

Don’t be a dick, but don’t be a pushover.

Seems like a large target to hit, but sometimes it’s not. You’re going to end up having to defend your design choices. (Hint: “because it looks cool” is never a good defense.) Every design decision you make must be defensible. When you’re just starting out, sometimes it’s difficult to put this in words—you know that something feels right, but it’s hard to explain why. Think about balance, contrast, flow—all those things your instructors talked about back when you were learning the principles of design. “Why is there a bunch of empty space over here?” can be countered with “The white space around that section of copy allows it to stand out from the rest of the content”. (I don’t know why, but some people see white space as a thing to fill up. You will spend your entire career fighting this notion.)

So, be assertive in defending your choices, but don’t be a snotty asshole (this is something designers have become known for, unfortunately). You’re a designer, not an artist, so your explanations need to be grounded in expertise rather than personal preference. This doesn’t work 100% of the time, of course. You will have clients that don’t trust enough in you or your profession enough to accept your recommendations. You may be called condescending or defensive when you try to explain your design choices (this has happened to me a few times, while very gently trying to explain why a client’s suggestions won’t work). Always remember the goals of the project, and strive to meet the creative brief. This is how all work should be measured.

That leads me to the second half of this piece of advice: don’t be a pushover. Look, your job is to give your clients something that communicates effectively. If what they’re asking for goes against effective communication, do your best to guide them toward a solution that works. Remember that you weren’t hired to make them happy, you were hired to achieve the goals of the project. Sometimes making a client happy and producing effective work are directly at odds. Sometimes it’s a losing battle and you end up having awkward conversations and going your separate ways. It happens. And yeah, it’s frustrating—for your client too, because they didn’t get what they wanted either. Mike Monteiro has a great outlook on this kind of stuff, and I urge you to read/watch everything you can from him.

Make concessions where you can. If a client’s suggestion doesn’t hurt the work, but isn’t necessarily the way you’d do it, let them have what they’ve asked for. You have to pick your battles, and if you fight back every time your choices are challenged, you’re both going to feel frustrated. This isn’t being a pushover, it’s being smart and flexible. Learn to recognize when you can afford to be flexible and when you can’t. Remember the outcome: effective communication, not making things pretty. I can’t say this enough: you are not in the business of making things pretty. “Prettiness” is just a side effect of good design, the sum of effective typography, balance, contrast, flow, quality photography, visible hierarchy, and all those other considerations that flash through your mind as you’re designing. I see so many websites with decks like “I’m Leigh Peterson, and I make pretty things with pixels.” Gah! No! You’re doing a disservice by selling yourself as a cake decorator. You’re not just icing the cake, you engineered the cake, including the complicated scaffold underneath all of that pretty icing. It’s lazy to say that you make pretty things–you’re catering to what you think people want to hear, while selling your entire trade short.

Specifically for freelancers:


If you’re not naturally prone to being organized, use tools that will help with that (Evernote, Pinterest, Google Calendar, task managers, etc.)


I shouldn’t have to say this, but I will anyway.


To me it’s hugely important to be yourself if you want to attract like-minded clients. I’ve had many clients that approached me specifically because they liked my tone and sense of humour. My mantra is this: you get the clients that you deserve. Accept that there are lots of really good designers out there—the thing that sets you apart from them is your personality, so show as much of it as you dare and you have a better chance of attracting like-minded clients. But keep in mind that “be professional” bit above.


So you’ve managed to make a career out of something you love to do. Well done! Here’s the thing though: it’s still a job, and when you’re getting paid to do something for someone else, it does eventually become work. Do you think I sit in front of my computer grinning like an idiot and writing musicals about how wonderful my days are? If I’m being honest, the majority of my projects are “get it done, pay the bills” kind of work, and only occasionally do I get to work on something really fun/interesting. Why is this? Even though people talk about wanting “creative, out-of-the-box solutions”—when it comes down to it, most of them actually don’t. They think they do, but most of your clients will want to do what everyone else is doing. Few of them will want to take chances, and some of them have real difficulty handing over trust. So be prepared for that reality.

It’s still a really cool gig, though.


Work-life balance is huge for me. While I really like my job, I also really like my hobbies. I like getting outdoors, spending time with my dogs, reading, drawing, painting, watching movies. I find it difficult to be effective when I’m overworked—I need to recharge—and sometimes that’s through exercise or hobbies, but sometimes it’s through quiet time on my couch. I may appear outgoing through my writing, but I’m deeply introverted. I’m quite happy to spend my days alone in my little office with the world safely at a digital arm’s length. I recoil at the idea of in-person meetings. I have certain parameters that keep me comfortable and happy, and they’re my responsibility to maintain. Remember that—balance is your responsibility, especially when you work for yourself. Learn to say no, and learn to say no without excuses (there’s nothing wrong with telling someone you’re just not interested in their project—that’s one of the perks of freelancing—you get to choose!)


First let me remind you that all of this “advice” is just stuff that seems to be working for me. You are free to take what you want out of it. This next bit sometimes sounds extreme to people, but it’s working for me.

I’m pretty picky about what clients I take on. I’m more interested in what a client is going to be like to work with than what the project is. So I read a lot into that first email, that first point of contact with a prospective client. Here are a few things that I watch out for:

  • I know exactly what I want, I just need you to bring it to life for me. This usually translates to “I don’t have any respect for you as a design consultant, but I would like to use your knowledge of the software involved.”
  • I have a project for you. Call me. The contact form on my website asks for specificity—”Please give me as much information as possible so that I can best respond. Your time is valuable, and so is mine!” Ignoring that plea and putting the onus on me to call and hunt down the details of a project that I might not be remotely interested in shows a lack of respect for my time. Watch out for people who have no respect for your time from the outset—it’s very likely only the tip of the iceberg.
  • What is your rate? Seems innocuous, but directly above my contact form in bolded text is a link to information on my rate. I don’t reject these people flat out, but I am immediately concerned at their lack of attention to detail. People who miss details like this tend to miss details elsewhere, and as design is a pretty detail-dependent line of work, this can lead to problems in client relationships. You may find yourself repeatedly asking questions that go unnoticed/unanswered, or pulling an approved print piece off the press because the client noticed a typo at the last minute. These aren’t insurmountable issues, but they do introduce bumps in your (hopefully) smooth process.

These are just some specific examples that I get repeatedly. Ultimately my point here is that trusting your first impression of someone can be crucial to your process. Every time I’ve ignored what my gut was telling me and taken on a client that didn’t give a good first impression, I’ve ended up kicking myself for it—because I was right every time.

In general, be on the lookout for people who:

  • are afraid to sign a contract
  • don’t want to give you a deposit (hint: always get a deposit if it’s not a client you work with regularly)
  • want you to do work on spec
  • try to get you to do cheap work by claiming the project will raise your profile, or enhance your portfolio (students and new designers often get caught in this trap)
  • are disorganized
  • allow your emails to go unanswered for days or weeks
  • are unprofessional (casual is one thing, unprofessional is something totally different)
  • have the attitude that they are doing you a favour by bringing you work

And if a client/project just doesn’t feel right and you can’t quite put your finger on it? My advice is to pass. Never knowing for sure is better than being right and getting yourself into a bad situation.


You may have noticed I don’t have anything in here about networking or cold-calling. I don’t do any of that, and that’s my preference—it doesn’t need to be yours. As I said before, I’m intensely introverted, and shrink away when I even think about networking. Even the act of selling myself on my own website is a challenge for me (my main URL is because even using my name as my primary URL felt pretentious—which is absurd, of course, but that’s how my weird brain works).

So use a little common sense. If you’re having trouble with connections—network! I had quite a few connections going into the freelance world due to working at a global agency. I generally don’t need to cold-call because I get enough people either recommended to me or finding my site organically that I don’t need to go pounding the pavement for work. I also have a lot of regular, ongoing clients who make up the bulk of my workload. But that’s me, that’s my situation. You need to be flexible and smart and tailor your methods toyour situation.


As I said, these are things that worked for me. But you’re not me. If any of this advice makes sense for you—cool! Glad to help. And if all of this sounds terrible—also cool! Glad to provide a counter point of view to help you justify that you’re already doing things right.