Dazed & Confused: 13 Exercises to Clear the Confusion Surrounding What You Want Out of Your Illustration Career


Do what you love, right? I mean you either fall into this camp or you don't, I do.

I think one of the many critiques of this advice comes from this place: what if I don't know WHAT I love?

Whenever I'm trying to encourage someone it's a lot easier when they actually know what they want.

It used to be that if they didn't know what the wanted or what they loved, I was just completely stuck on how to help...but I've got some new ideas...and they feel like they are helping me a lot.

Whether you know exactly what you're shooting for or you're completely lost in the woods, everyone can get stuck in a cloud of confusion concerning their illustration or creative career.

I think it's important to mention that your career is often steered by the personal work you choose to do, which most of these exercises point to in some way.

Without anymore blabbing, here are 13 things that help me when I'm in that place of panic-busy confusion:


1. Examine Your Motives

Simon Sinek would say the first question to ask is: WHY am I confused?

Often my confusion comes from thinking I want a lot of things that I actually do not.

One of the easiest ways of sorting through this is to make a list of all the things you think you want, then try to explain to yourself why you want these things.

Then label them as you see them: pure motive, neutral motive, impure motive.

The only ones I'd get rid of are the impure motives. 

For me pure motives come from natural desires to create and express, from a place of passion or from a place to help someone else. (These motives often translate into the best personal work).

Neutral motives are usually more commercial focused, i.e. getting more editorial work by expanding the subject matter in your illustrations. These things are just fine, and often important things to address...not especially pure or impure, just necessary.

Impure motives are driven by things like jealousy, greed and insecurity.

Other than moral objections, I suggest you let go of the desires under the impure category because they don't tend to have great pay offs.

Usually following these impure desires gets you off on a side road that leads to a dead end, many false starts and a lot of wasted time.

How much better does it feel to listen to music that just purely moves you, than listening to a band for the impure reason of thinking other people think it's "cool". One feels amazing, the other a chore. Which will you most likely stick with?

Don't waste your life indulging these impure motives.

2. Set Time Aside Just for Thinking About This...and Actually Think About It

Go on an early morning walk, take a weekend trip or take a bath with one goal: to think about your career.

Often when I try to do this I end up finishing the walk, bath or trip, and realize I haven't thought about it at all.

One way of combatting this is forcing yourself to take notes as you go on paper or just on your phone.

Often this confusion cloud is just a problem that needs to be solved, that is not incredibly difficult, it just takes a little bit of effort.

If you're like me, you soak up information, thoughts and worries like a sponge. Often though we walk around totally saturated, carrying the weight of all this cloudy mess of info, and all we need to do is make an effort to sort through it.

3. Talk to a Peer and a Mentor

One of the most effective ways to process this cloud of confusion is to talk about it. I prefer to do the previous step first, just so I've done my homework and actually know what I want to talk about with these people.

It's important to talk to both peers and mentors because they give you different things. Both have the ability to enable breakthroughs in this area.

Peers are great for venting but also can point out where your thinking about our industry is skewed by your own misconceptions and insecurities. They also help you brainstorm.

Mentors tend to be better at having a birds eye view. Challenging you in one area and alleviating worry from another. They also tend to be able to connect dots in your thinking that you can't.

Sometimes it's just a case of fresh eyes.

When you are in the thick of it, it can get really convoluted. It's like working on a word search, and you can't find the last word, you've been starring at this thing for too long...and a friend walks up and sees the word straight away. Sometimes the answers are obvious we are just too familiar with the problems.

4. Write it Out.

Talking about your thoughts is giving form to the formless. Writing about it takes this a step further.

Think of it in terms of clarity: thinking = eyeglasses, talking = magnifying glass, writing = microscope.

Writing is getting down in the nitty gritty because you have to really pin it down and choose your words.

I think it works best after the thinking and talking, but I also think it's the most important part of the process. It's usually at this stage when you have a tangible breakthrough that you can actually follow through with.

Side note: writing about it on your blog can help others, which can act as incentive for people to come check out your work.

5. Have Faith

Ok. You may not like that word.

But here's how Steve Jobs said it:

“You can’t connect the dots looking forward; you can only connect them looking backwards. So you have to trust that the dots will somehow connect in your future. You have to trust in something – your gut, destiny, life, karma, whatever. Because believing that the dots will connect down the road will give you the confidence to follow your heart even when it leads you off the well worn path; and that will make all the difference.”

Sometimes the confusion comes from wanting something and we don't know why we want it.

At ICON8 (an illustration conference) this year the keynote was the lead singer for OK GO. His main point of his talk was to have the faith to make things that you don't know will work or lead anywhere. His band had a string of strange successes doing unusual things that bands usually don't do, eventually leading to their giant breakthrough.

That's why I always believed that following what you love is an act of faith, trusting this thing has been placed in you for a reason, and if you see it through, the dots will eventually connect to something bigger.

6. Compare Yourself to Illustrators Ahead of You

I know I often say comparing yourself to others is not a good idea, and in many ways it can go horribly wrong...but I think there are ways that it is a complete necessity.

Something that really bugs me actually is when illustrators say that they don't really look at anyone else's work or keep up with anyone else's work.

To me it sounds like you're saying: I've learned everything I need to know.

Imagine the same attitude in a different profession, like science.

Can you imagine a scientist saying, "I don't really read any of my colleagues papers." No way, they love their field, and their always looking for ways to advance it.

It's an imperfect analogy in some ways, but I think it holds some truth.

One of the best ways to unlock your confusion is to look at people you respect that are ahead of you, and ask yourself what types of jobs or output are they doing that would seem fun to you.

I do think it's important to look to those who have come before you and find your place in some sort of niche. It just gives you an edge of context, which provides that little bit of confidence and comfort to keep going.

Almost every really successful artist can gush over someone (or several people) that came before them, someone who to them, seemed to have it all figured out. Your path will in the the end look dramatically different to those you admire, but that will happen on it's own in many ways.

7. Then...Don't Compare Yourself to Other Illustrators 

This seems to contradict the previous point, but it's more of a next step to the previous point.

Looking at others will never be the final step in how to figure out where you want to go.

But, here is a kind of deep thought that gets to the core of this: you are more than what you like and don't like, but what else are you? It's hard to explain beyond that.

Here's an exercise that I think can solve this problem: take one of your main influences in illustration and juxtapose it with your biggest inspiration outside of visual art.

For me it looks like this:

My work is like if Alexander Girard was super into Fraggle Rock.

If you know my work, I think you'd agree that it's a pretty good description.

What's great about this contrast is it warrants something pretty unique to you.

Every since I created this analogy, it's been a tool for clarity. Whenever I start new work and I try to shoot in this direction...it just feels right.

8. Check When the Last Time You Ate Pizza Was

Sometimes I go weeks without realizing it...don't let it happen to you.

9. Don't Neglect What You Have

It's cliche to say that things move really fast now, but it's actually a fact. We see more ads, work more hours, connect with more people than we ever have.

It's effected our employment too. We don't stay very long at a job any longer.

When it comes to your freelance illustration career though this can have negative effects.

Sometimes I get a part of my career up and running, like editorial work, and when it's at a "good enough" level, I'm straight onto something new, like books. This mentality has lead me to sometimes have a portfolio that's not as good as it could be, because I'm neglecting to take things from "good enough" to "great".

It also means I'm always working on the future instead of stewarding and enjoying the present.

One thing that helps with this is take a break from social media and following other artists. Sometimes those things can cause us to chase 100 different things at once.

I realized recently I had achieved something in my work, started working really hard on a very different path, and as soon as that path looked like it might work out, dropped it and moved right onto a completely different path!

10. Ask yourself: What Do You Feel Like Making Today

Super easy, super effective.

Sometimes we start down a long road, that doesn't sound that fun initially, but we think once we get to the end, or just further on, we will get into it. Very rarely true.

What type of work sounds fun to make today? Take that road, you'll probably enjoy working on that type of work for long while.

11. Don't Neglect Your First Love...as Long as You Still Love it.

Recently I realized poster type - one off - images were almost completely absent from my portfolio, and I hadn't made anything like that in a long time.

Not only is this work why I became an illustrator, it's also still my favorite type of work to do.

I'd gotten so caught up with dreaming big, and future plans, I neglected my first love. I was stealing so much joy from myself, along with future commissions in this sector of work.

I know I don't have to convince you that I am by no means the Michael Jordan of the poster industry (heck I'd be happy being the Tony Kukoc) but it kind of reminded me of how Jordan must've felt coming back to the NBA after his baseball fiasco.

Or when Yusuf Islam, aka Cat Stephens, finally returning to the music industry. (Again, I'm no Cat Stevens of the illustration world, but maybe I could be the Boyz II Men)

Don't let anything steal that thing from you. Not pride, not artistic integrity, not other's crass insults. Maybe there's something you need to revisit?

12. Dream Big, Invest Small Experimenting

While you are sticking to your first love...I think it's important to continue to dream big and with that invest by making little bets.

I think the key word is little.

When dreaming big goes wrong: when you drop your first love and go all in on something giant and new.

AKA when that band that gets a little success and goes from lo-fi bedroom soft acoustic music, and takes the new budget into the sophomore album with a full on orchestra produced by Will.i.am!

Dream big but do like Bob and take baby steps.

Make little experiments in the secret, always be tinkering on new things, but don't hedge all your bets in completely uncharted territory.

If you do, this will leave you very confused.

13. Cool Your Jets

I love Pencil vs Pixel.

Recently I listened to the episode where Cesar interviews the great illustrator and letterer, Jen Mussari, who also happens to be a friend of mine. Jen's final advice was simple and also really brilliant "Cool Your Jets".

For some reason I think us artists can get pretty worked up...and I'd say I never get more confused than when I've really overthought things. 

I think all of these exercises are helpful for breaking through confusion, but at the end of the day, sometimes you just need to let go.

Often our best work and best decisions come from a place of peace, not anxiety.

One way this works is just to take a break from work and thinking about work. How often have you been laboring on a piece of illustration, really unsure about how you felt about it, but returned a day later and totally loved it with fresh eyes? At the very least, it's usually much easier to see what's wrong with it.

Sometime we just need to walk away, all the obsessing just increases the fogginess.

Go spend some time with your family, or with non illustrator friends. Get outdoors, and relax. Give yourself a buffer between you and your work. When's the last time you took a vacation... and didn't draw?

Often this is the most effective solution there is.