A few months ago, a high school senior, Samantha Cleveland, sent me a list of interview questions. Samantha is interested in a career in graphic design, and I answered as honestly as I could. I wrote quite a bit, so I figured that I would share. Enjoy.

Why did you decide on a career in graphic design?

I can’t recall any moment when I made a “decision” to have a career in graphic design. My parents recognized that I was artistic as soon as I was old enough to color and draw. Art was just always “my thing,” and it was only natural for me to assume that I would be an artist for the rest of my life. I think we often get side-tracked into thinking that we need to pursue the occupation that makes us the most money. I got good grades in school, and I knew there was an option to pursue a career in something like medicine, or law, or those other seemingly high-paying careers. But those options were never really options for me. I viewed them as boring, and I viewed art as fun. So I naturally kept art as my main priority, and always have. I think part of our purpose is to spend our time doing what we are best at. I was lucky that I found a way to make a living at doing art projects all day.

What tools and knowledge are most helpful in pursuing a career in graphic design?

I’ve found that having a responsible, task-oriented approach to a seemingly free-sprited field is extremely important. The biggest problem that I see in most artists and designers is that they are so self-absorbed and proud of how artistic they are, that they tend to be very irresponsible, unreliable, and slow. They prioritize self-expression over work completion. My biggest asset is the speed at which I do projects, the timeliness at which I deliver my work, and the organized workflow that I maintain. This has helped me to maintain good rapport with my clients, which has cultivated many relationships, and steady work that has lasted over a decade now.

What are some aspects of a great portfolio?

I’ve always been more impressed with a proficiency in a wide range of styles than expertise in one single aesthetic. The reality is that most jobs will require you to create work one day that may look completely different than the work you did yesterday. It’s the ability to bounce between these styles that will make you a valuable asset to your employer. However, if it’s strictly illustration jobs that you seek – then you will eventually benefit from defining your own style, and perfecting it. A career in Illustration has many different principles than a career in Graphic Design.

How did you start your career as a graphic designer (internships, job applications/interviews, etc.)?

I had an odd path to my current career in graphic design. Like I mentioned, I had always been artistic, and spent most of my time drawing. My friends and I started a band when we were thirteen years old, and I naturally created the logo and tape jackets for our band. As our band grew, so did the nature of the projects that I created for the band. I would find myself designing fliers, cd covers, t-shirt graphics based upon our need at the time. At age 18, my band signed to a record label and we started touring nationally. Most of the bands that we toured with liked the merch that I designed, and asked me to design merch for them as well. This snowballed into consistent paying work for me that I did from my Powerbook in the van and in hotels. Around age 22, there became an odd overlap between my income from design, and the income from the band, in which I was making more money designing t-shirts for bands, than I was performing in my mine. The decision soon came to take my design operation full-time. I’ve been completely freelance and full-time since 2005. I’ve never worked any design job other than my own freelance projects, which is quite rare. I’d like to think it came from an unwavering persistence to my work, but the truth is that I’ve been very very lucky.

What are the major differences between working free-lance and working for one company?

Since I’ve never worked solely for a company, I can only speak from the freelance perspective. The main difference, for me, is freedom. This isn’t the freedom of skipping around all day, and living a life-long vacation, but the fact that I have a freedom to do projects that I enjoy, and to do projects because I want to, and not because I have to.

However, I wouldn’t wish this level of stress upon my worst enemy. While most people can walk away at 5pm everyday, my job never stops. Working on several time zones, and crazy deadlines mean that you can find me tackling a mountain of work at any time of day or night. There is no one to delegate work to, only my own shoulders on which I carry this whole operation. From client interaction, scheduling, taxes, invoices, the work itself, revisions, etc – I do every single bit of it.

The biggest problem with freelance is that making a good living at it is extremely difficult, and in order to pull it off, you must exhaust yourself. I find myself both constantly exhausted, and constantly proud of the fact that I’ve been able to do this on my own, and make a great living at it. At this point, there is no way I would ever work for a company. Freelance is all that I know, and I plan on sticking with it for many more decades to come.

What were/are your career goals as graphic designer?

My biggest career goal is to make cool stuff. Plain and simple. There were never any income figures, or huge accounts that I wanted to obtain – just the ability to make the type of stuff that excited me as a kid, when I would get lost looking at all of the graphics in old skateboard catalogs. I get to do this stuff, all day, every day, and I know that the 12 year old version of me would be so excited to know what he’ll get to do for a living someday. My goal was, and continues to be, to maintain that youthful excitement for creating art. I’ve had it my whole life, this passion for making stuff, and I’ll do whatever it takes to maintain it for the rest of my life.

What do you do in your typical working day?

Ideally, I wake up early. Like, really early. Like 4:30am early. I make a protein shake for breakfast, I shower, get dressed, put on my shoes, make coffee, walk my 15-20 feet commute to my home office, and get to work.

For me, the real work happens when I can fully immerse myself in the project, without any distractions. This is that “in the zone” feeling that happens when you get lost in your art. I do whatever I can to get there. My usual methods include working when no one else in the country is awake, ( hence the 4:30 wake-up ) listening to podcasts or ambient music, running a fan or air purifier for white noise, and turning off all phone, email and social media distractions. Once you pinpoint the distractors in your work day, it becomes easier to avoid them, and only focus on work.

I will break when I finish a project, or reach a stopping point. I usually spend that time getting lunch, talking to my wife, running errands, etc. I get back to work until I feel okay about stopping. This is usually 4-6:00 pm. I can feel confident that I put in a good day’s work, and met all of my deadlines – and won’t feel guilty about watching TV. It’s not uncommon for a last minute request to come in during the evenings, and I do my best to oblige. Setting boundaries with loyal clients is overrated. If someone needs something, and you can do it, do it. I try to prioritize being good to people, not letting them know how busy I am.

I try to get to bed before 11:00 pm. I look over the next day’s projects, and try to fall asleep thinking about them.

What are the working conditions like (stress, pace, travel, environment, hours, etc.)?

There are days where I put in 13-14 hours of work, but some days that I put in 3. The workload is insanely busy some days, but then there are days where I can take my wife to lunch at 1:00, and not have to rush back. There are enough of those easy days to make up for the majority of high-stress days.

I’m freelance, and work from home, so there is no commute. But, that also means there are no co-workers and I have no one to bounce ideas off of. While I would consider myself an extrovert, I’m most efficient and productive in an introverted state. I’m sure being around co-workers would get under my skin pretty quickly, so I’ll stay solo.

What are some of the designs you have created and their successes?

I’ve designed thousands of pieces, for hundred of bands. It’s not uncommon for me to look back on my work, and not remember creating a piece. But I’m always excited to see some of the work that I’ve done for Pearl Jam, The Beastie Boys, Blink-182 and Mumford & Sons. I’ve been able to walk into Target, Wal-Mart, Hot Topic, Delias, Spencers, and several concerts, and see my work. I never get used to seeing work that I’ve created get sold globally. I’ve been able to have a tiny piece in shaping the visual culture of our time, and I’m so grateful for the opportunities.

What is your greatest accomplishment in your opinion?

My greatest accomplishment is making a job out of doing what I’m best at, making a good living at it, and doing it all on my own. I set out to prove a lot of things to myself, and to never stop trying to go beyond what I thought I was capable of. I’ve achieved all of that, and can honestly say that I’m proud of myself. I’m actually being what I wanted to be when I grew up.

In your opinion, what characterizes a good designer?

A designer is essentially a decision-maker. We’re often making decisions about elements and how they interact with each other, and with the viewer. A good designer is one that has tremendous artistic skill, but also the knowledge to know how to use it effectively. Being a good designer is very different than just being a good artist in general. A good designer must care about how someone will react to and digest a piece – so they must care more about that audience than they do about their own agenda. There is a selflessness needed to be a good designer – knowing that you’ll do whatever is necessary to get the message across, no matter how much or how little work that may take.

Would you choose this career if you could make the decision again?

Definitely. I would choose to do the exact same thing that I’m doing now. No question.

What (if anything) would you do differently?

I would figure out a way to involve other people in my life more. My work benefits from my isolation, but my mind and overall well-being benefit from community – which, unfortunately, I haven’t prioritized.

What are the most rewarding aspects of your job?

Any moment that I can look at something that I created, and be genuinely impressed by it. Also, any time I can see a client’s excitement for what I came up with.

What are the least rewarding aspects of your job?

Those times when I exhaust myself on a project, send it in, and the client is too caught up in the machine to reply with a “Thank you.” We are all cogs in a bigger machine, but it’s nice to work with personable clients, even if your only interaction is email.

How you respond to the notion that art is not generally considered a viable career option?

I would agree. It’s not. There is often some odd, winding path that successful artists went down to get them to the career they have. This path is so random, that there is no way to provide a student with steps or a guideline on how to get there. The majority of ready-made design jobs that most students get placed in provide little to no reward, making these artistic people hate design altogether.

The truth is that most people hate their jobs because they’ve never had the courage to break away from convention. The only thing the convention, or the suggested path tells you is how to achieve a mediocre, lower-middle class lifestyle. If the majority of America is unhappy, and hate their jobs, you can only assume that this suggested path laid before you will only lead you to that same unhappy life.

True happiness comes from finding your own path, and breaking away from the herd. You have to know that the herd is unhappy, and there is no logical reason to stick with them. It’s your youthful curiosity and tenacity that will eventually get you to a life that you can be proud of. You will never find true happiness in simply being somewhere in the herd.