Career Pressure | A Design Q&A

I try my best to answer all the comments on my YT channel, but some deserve longer explanations. So, a Q&A series felt appropriate. It gives me an opportunity to answer your design and career questions.

Here are the questions in this set:

1. I don’t have time to redo my portfolio, but I need to apply for jobs now.
2. I’ve been freelancing, but I feel stuck. How do I grow from here?
3. I feel like I’m always the runner-up for roles. What am I missing?
4. I just finished school, but I’m scared my work isn’t good enough yet.
5. I’m applying to big-name brands, but never hear back. What should I change?

Feel free watch the video or read below.

I don’t have time to redo my portfolio, but I need to apply for jobs now.

We’ve all been here and we promise ourselves it won’t happen again and it always does, but let’s not dwell on what you didn’t do and just focus on what you can do. I actually had to do this for 2 freelance jobs in the past year, which is a little different, but the same idea.

The first step is to get organized. I have a hard drive of all my projects. Each folder has high-res jpegs, which allows me to grab them very easily. Some of you, like me, have a lot of projects, you don’t need to review all of them because you already know which projects are your strongest.

Next, you just have to get something together, literally anything. If you have a website, regardless if the projects are old, just replace or add two projects, which can be easily done in a couple of hours. If you don’t have a website, I highly recommend putting together a capabilities deck. Don’t overthink it.

This approach isn’t as robust as a website, but it can come together pretty quickly. Work in whichever software you feel most comfortable. Even better if you’re using Figma, skip the PDF and send a prototype link!

Here is what I put together for my quick and imposter portfolio… I didn’t even have case studies.

I should caveat that this is a band-aid, not a solution. It’s not meant to be your official portfolio. I just buys you time to put together a more thought-out portfolio after. At the very least, your immediate problem of being able to apply for jobs is mostly solved.

I’ve been freelancing, but I feel stuck. How do I grow from here?

When it comes to freelancing, growth isn’t exactly linear. I think this depends on whether you define growth as bigger, more exciting freelance projects, or climbing the corporate ladder.

If you want bigger projects, there’s really no way around the portfolio. Clients can’t guess where you want to go next, they need to see proof of the projects that you want to be working on. This is where a passion project comes in. In particular, one that reflects the kind of work you want to be doing.

It should maintain or exceed the standard of your other portfolio pieces. And even though the project is made up, you need a brief so that you can present it properly. That means creating client goals, deliverables, etc. All the same things you would work with on an actual project.

Now, if you’re looking to climb the corporate ladder, the “easiest route,” (caveat on easy because of the current job market) but try to get a job in the same space at the level you’ve been working at. It is a much smoother transition, and from there, you can grow into new roles from there. This can lead to bigger and more exciting projects within the job or freelance if you decide to go back to that in the future.

I’ve gone freelance 3 times in my career. I will say, I wouldn’t have the projects I’m working on today had I not climbed the corporate ladder. I’m not saying you have to do that, but there are advantages like expanding your network, officially getting an art director or creative director title, and gaining exposure to projects that wouldn’t typically come your way as an independent freelancer.

No matter which direction you choose, as long as the work excites you and keeps you going creatively, that’s growth!

I feel like I’m always the runner-up for roles. What am I missing?

I have good news and bad news. The bad news is that the final hiring decision is completely nuanced and a lot of it is out of your control. Maybe the other candidate had an internal reference. If you had to do a design test, maybe theirs was slightly stronger? None of this is fair, but it definitely happens.

The good news, actually great news… if you’re getting to the final stages, that means your portfolio is clearly strong enough to get a job, which is a step ahead of a lot of other people. Most people don’t even get a callback, so I would say just keep applying. It’s only a matter of time until the wind, the moon, and the stars align for you.

I just finished school, but I’m scared my work isn’t good enough yet.

This is a classic case of imposter syndrome. A lot of us deal with this our entire careers, including myself. I think the best piece of advice I can give you is to not measure your work with someone else’s ruler. There is always going to be someone better. We can’t all be a Gail Bichler or Felix Pfäffli.

Something to keep in mind is that your portfolio doesn’t need to be perfect, it just needs to show potential. I’ve reviewed a lot of student portfolios, and the things I look for are:

a solid grasp of typography, layout and color. (These are foundational, and they can’t really be taught on the job.)
a breadth of work that shows you’ve explored different formats.
a point of view as a designer.

I would say these are good baselines for “good enough.” From my experience, I didn’t go to a big NYC design school, and when I saw the portfolios coming from graduates of RISD or SVA, I wanted to light myself on fire. What I slowly found out, your work can get you in the door. How you present yourself gets you the job.

I’m applying to big-name brands, but I never hear back. What should I change?

If you’re not hearing back, you might not need to change your work — you might need to change your approach. Again, it depends… Where are you coming from? If you’re working at the Herald in Piedmont, North Dakota, it’s going to be pretty tough to go to Weiden & Kennedy or LVMH.

(Piedmont, North Dakota isn’t a real place. Also, apologies if I offended anyone from North Dakota.)

Not the biggest jump, but I couldn’t build the publishing career I have, in Chicago, so location has some factor. Don’t get me wrong, some people do incredible work, get noticed and the big break comes. I don’t think that’s the norm though. And it’s not because of a lack of talent. I think it’s more that the leap you’re trying to make is too big, so you might need some stepping stones. The best stepping stone would be to get a job at an agency that works with big brands, even better if they’re the brands you’re targeting.

Your portfolio needs to speak their language. Have you worked on a large campaign before? Have you done in-store, activation, commercial, whatever have you. All of these are necessary to get their attention.

The other factor is that applying online seems to be where applications go to die. Are you able to find an internal referral or even a referral from a previous employee? You want to get in through the door before they open it up for online applications.

You can’t control who sees your application. You can control how much your work looks like you belong in the room, and that will definitely find you more success.

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