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Hell With This,
Let’s Do It Again

Justin Kemerling
Jun 30, 2015 · 8 min read

A Five-Year Self-Evaluation of a Self-Employed Graphic Designer

My apologies for not making one of these happen before now. I think it’s something we should typically do once a year.

That’s okay. The last five years have been a bit of a blur.

Thanks for understanding. So let’s get to it. What are your goals for the next five years? Well, actually, let’s hold off on that one. How about, on a scale of 1 to 5, how would you rate your current satisfaction with your current role?

Is 5 I love it?

Yes. 5 is I love it.


Why the asterisk?

Because rating scales are lousy ways to ask if someone is satisfied or not.

Then please explain.

Okay. On a typical day I wake up around 7 and take the dog for a walk. We head to the top of the hill to see my lovely wife off as she drives away to the office. After our walk, I do a little workout. You know, push-ups, sit-ups, mountain climbers, jumping jacks. Then I take a shower because I love showers. Then I make some exceptionally good coffee. All of which is amazing.

Okay, good to know. And the job satisfaction part?

Right. Well after the coffee is French pressed I sit down at my computer. I work for a little in the home office with my design assistant, a seven-year-old Wheaten Terrier named Jezebel. She’s my spirit animal. Then I typically ride my bike to a co-working space to really make progress on the projects I have going on. I work the morning away and then it’s lunch time. In the neighborhood where our co-working space is at, there’s your choice of pizza, falafel, or greasy diner food. At one place, the best pork belly sandwich in the city. And at another, a really amazing cauliflower sandwich. I mean this thing is one of the best foods my face has ever tasted. If I could, I would have this thing every day morning, noon, and night. But that’s probably way too much cauliflower. In the evening, there’s this amazing little French bistro. Or this amazing little Italian place. And the pizza again. That place also has amazing specials. On Mondays…

The job?

Right. The job. Just put down 5.

Moving on. In the last 5 years, what accomplishment(s) are you most proud of?

Good question. I think one thing would be a set of parties my wife and I hosted last year. We have a nice old house in midtown with a great deck setup. Lots of seating, a place for a little fire pit, and plenty of yard to play Bocce Ball. The trees back there are fantastic, too. And we have such amazing friends who are so great to hang out with. We’re getting to be pretty good hosts. My wife is a stellar cook and I can assemble an impressive grouping of beers and playlists. I’ve been way into beer in cans lately and there’s a small place not too far from us with a huge selection. I find that an ice cold can is one of the best things in life. And it’s easy to recycle. Great for the environment. Win-win.

That isn’t really what I mean.

The playlists! Those I’m really proud of. Twenty years ago last year is when a bunch of great music was released. Weezer’s Blue Album, Green Day’s Dookie, Pearl Jam’s Vitalogy. It was awesome to have those on a playlist mixed in with the new War on Drugs, Jagwar Ma, and Future Islands. Then you add some LCD Soundsystem, Bowie and Mercury, Pixies, and, of course, the Clash. That playlist alone made for some pretty special nights.

Let’s move on. What area(s) would you like to improve upon?

Yes, there are so many. It’s been so long since I was good at cooking anything. You know, the really great dishes with ingredients from a farmers market. I want to improve upon my repertoire there for sure. Maybe do a little more painting. I love scribbling a bunch of paint on a canvas with the lid or a drywall scraper thing like some kind of super resourceful Jackson Pollack. I used to be a lot more newsy, too. Now I can barely fit in The Daily Show with Jon Stewart. Ask me about any issue in any corner of the world five years ago and I’d have an opinion. (Thank you Democracy Now!) Paul Krugman still has a column right? Right now it goes current workload, new business, accounting, invoicing, emailing, team-building, IT, new fonts, new trends, software updates, statements of work, RFPs, portfolio updates, self-promotion, social media, collaborations, and new ideas and on and on until my brain is entirely consumed. I think I just need to read more books. Maybe get back into screen printing. And I don’t really know that much about whiskey. That too.

I’m sensing a work/life balance pattern here. This is good. Building on that, what things have disappointed you in the last five years?

That time I caught myself talking about kerning in public.

The space between letters?

Yes. Not foreign policy, voting rights, or whether or not President Obama has been making good on his campaign promises. It was embarrassing.

Hmm. This is one I got from a conference last year. What has stayed the same? What has been dropped or failed? What has surprised you most?

Those are 3 questions.


Okay, things that are the same. My very first client still kicks ass. My worst clients have all been dropped. And what has surprised me most is the cathartic nature of the word fuck.

I see. I’m glad you brought up clients. Let’s dig a little deeper there. When you say your worst clients, can you give an example?

Well, there have been a couple times this has happened. I’m working away on a project. Back and forth with the client. There are rounds of design and feedback. We’re working through problems and solutions together. And then, all of a sudden, the client is like, “yeah, we have this consultant we’re now working with and he/she had another designer work up some stuff as well, here it is, what do you think?” Not only is this other stuff complete shit but it isn’t held to the same rigid review process as the designs we had been working through. Double standards are no good. Shitty design work is no good. And that’s a process that doesn’t strike me as particularly honest, and that’s no good. All that leads to the Hell With This moments. When that happens, those clients don’t remain clients for very long.

The Hell With This moments?

Yeah, or the Fuck It moments. The times when you raise up your hands, throw in the towel, and just get it done.

So would you say a Hell With This moment is something that prevents you from moving forward?

Oh no, I move forward for sure. At lightning speed. Get that project out the door and move on to the next thing with the really great clients.

And how would you define the really great clients?

They have vision. They do what they do. They hire me to do what I do. They give you hugs, meet up for beers, never say “make the logo bigger,” and pay invoices within the allotted timeframe. You know, the simple things.

So would you say the search for great clients is something that keeps you up at night?

Actually, I’d say something that keeps me up at night is that scene from Game of Thrones where all the good guys and good ladies get locked in a big hall at a wedding and brutally killed. Or towards the end of Boyhood when Patricia Arquette says “I thought there’d be more” before Mason goes off to college. Fucking heartbreaking and powerful. Those keep me up at night for sure. And taxes during tax time. Such a pain in the ass.

Why do taxes keep you up at night?

There’s a joke out there somewhere about a CPA, a lawyer, and a financial planner walking into a bar. Let’s just leave it there.

Okay, how about, in terms of KPIs, how are those going?

Do you even know what those mean?

Not really. Let’s move on. Let’s look shorterm. What are your goals for the next six months to a year?

Maybe more Dribbble likes? But then I’m like, Dribbble, what a waste of time. And now Dribbblisation is a word and all of everything is going to hell in a handbasket. Follow me on Dribbble.

Not sure I follow.

Yeah, me neither. Have you thought to yourself everything is going to hell in a handbasket at any point in the last five years?

Certainly. After the first debate in 2012 when Barack totally bombed and Mitt looked like an actual human. I was terrified. When it looked like that dirty tarsands pipeline was going to get built right over the aquifer. Michael Brown, Eric Garner, Freddie Gray, and now with Charleston. Those very real, very serious issues keep me up at night.

Looking at the next five years, does anything get you stoked?

Lots really. Startups that are looking to make voting better. Foundations that are looking to solve community problems. Artshows that are bringing people together around issues of race, justice, and economic opportunity. People who are putting on rock concerts, hosting inspiring conferences, working for campaign finance reform, and looking at what’s next in higher education. So many amazing things are happening right now that the next year, two years, five years will be really interesting.

And probably a blur.

Probably a blur. Which will certainly be one of the challenges.

Indeed. It will be a challenge to not get consumed by work. To be better at creating boundaries around office time. Email can wait. Slack can wait. The corrections can wait. The next self-promotion social media post can wait. Make time to think. Make time to be weird. Make time to have more fun. There is nothing wrong with Hillary’s logo and she does NOT need you to redesign it. Although Jeb’s logo, that’s pretty terrible. Going all Office Space on an old printer that is the bane of your existence is a perfectly acceptable response for a self-employed business owner in his mid-thirties. If your friend says he’s watching the game at his place and he has pizza and beer, you go. Every time. When you have friends that move away make damn sure you go visit them as often as you can. A 30-hour work week and mandatory six weeks of vacation a year. Those are things I’m going to try to make happen at some point.

Those are great goals.

Damn right.

Well, I think now’s as good a time as any to get this wrapped up. Final comment?

Don’t go to concerts, stand in the front, and have conversations.

Okay, and the next five years?

Fuck yeah, let’s do it again.

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