Most Illustrators Fail at Stage 2 (You Don’t Have To)

 

If you’ve been trying to make illustration work for years, posting your work online, improving your skills, watching videos like this one, and you still aren’t getting consistent clients, I made this video for you.

 

There’s a point a lot of illustrators reach where they’re no longer beginners, but they also don’t feel established or stable.

 

You’ve put in real time and effort, but the results don’t quite reflect that yet.

 

What often happens at this stage is people start doing more of everything. More posting. More styles. More platforms. More advice.

 

It feels productive, but it often creates noise and distractions.

 

In this video, I want to explain why this stage exists, where it sits in a typical illustrator’s career, and how you can get through to the other side.

 

I’m James. I’ve been making videos to help illustrators with their careers for more than five years, and I still feel like a beginner figuring things out.

 

This video was inspired by a newsletter title from illustrator and muralist Dave Bain, who’s been in the industry for twenty years. He asked a simple question: can I still call myself an emerging artist?

 

That got me thinking. When do you stop being a beginner? When do you become mid-career? And when do you actually feel established?

 

Is it about money? Fame? Your client list?

 

The truth is, the middle phase of your career is usually the longest part.

 

Most illustrators assume they’ll go from beginner, to a few clients, to feeling established fairly quickly.

 

But in reality, very few illustrators ever reach a point where they feel like they’ve “made it”, even twenty or thirty years in.

 

There’s always more to learn, and the better you get, the more your goals grow with you. The goalposts keep moving.

 

I’ve never met an illustrator who feels like they’ve done everything they want to do. That includes people who’ve been doing it for forty or fifty years with incredible careers behind them.

 

They keep working because they love the work.

 

Would you ten years ago be happy with the progress you’ve made, even if you don’t feel like you’ve made it yet?

 

Mine would be pretty proud, I think.

 

What do you think, 27-year-old James?

 

See… speechless.

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Stage 1: Learning

 

Stage one of your illustration career is the learning phase.

 

This is where everybody starts. You’re building foundational skills, figuring out what you enjoy drawing, experimenting with tools, influences, and styles.

 

There’s very little pressure at this stage, because the goal is improvement, not income.

 

Some people start in their twenties. Some start as kids. Plenty of people start much later.

 

Progress here usually feels fast. You can look back six months or a year and clearly see improvement.

 

That’s motivating. It feels like things are working.

 

There’s nothing wrong with being a beginner. Everyone has to go through it, and for many people it’s the most enjoyable phase.

 

Going from no skill to some skill is a big deal.

 

And going from no clients to one client is incredibly motivating.

 

Stage one is exciting and rewarding. But the approach that works here won’t carry you through the rest of your career.

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Stage 2: Trying

 

Stage two is the trying phase.

 

This is where a lot of illustrators find themselves for much longer than they expected.

 

You’ve got some skills now, maybe even a decent portfolio, and you start trying to turn illustration into something more serious.

 

You’re posting your work. Reaching out to clients. Applying for things. Seeking out opportunities.

 

You’re doing the things that feel like the right moves.

 

The frustrating part is that effort goes up, but results don’t always follow.

 

You might get a client here and there, but nothing feels consistent.

 

Progress becomes harder to measure, and it’s no longer obvious whether what you’re doing is actually working.

 

The quick progress you felt as a beginner slows down.

 

This is where self-doubt creeps in. You compare yourself to other people, question your skills, and wonder if you’ve actually got what it takes.

 

A lot of illustrators get stuck here. They stay busy, keep trying, but the momentum they had in stage one isn’t as encouraging anymore.

 

And this is also the point where a lot of people give up.

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The Dip

 

This stage is what Seth Godin describes as “The Dip”.

 

It’s the point where progress slows down, effort feels heavier, and it becomes much harder to tell if what you’re doing is working.

 

Early on, improvement is obvious. Later on, it’s more subtle. And that catches people off guard.

 

When illustrators hit this phase, they often assume something has gone wrong.

 

That they’re not good enough, or that illustration just isn’t right for them.

 

But that’s not what the dip means.

 

The dip isn’t a sign you should quit. It’s a sign that the easy progress is over, and the strategy that worked earlier needs to change.

 

And this is important: the dip isn’t about blindly pushing through at all costs.

 

Sometimes quitting is the right decision.

 

Getting through this stage often means quitting a few things that aren’t important, so the one thing that is can finally work.

 

If illustration is that important thing, this is the phase where focus and direction matter more than effort alone.

 

Most people don’t fail here because they’re not good enough.

 

They fail because they panic, change everything at once, or never stop to decide what’s actually worth committing to.

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Stage 3: Focus

 

Stage three is about focus.

 

This is where illustrators stop trying to do everything and start being deliberate about what actually matters.

 

Focus doesn’t mean doing less work, or drawing the same thing over and over.

 

It means being clear about what stays consistent, what can vary, and what you can let go of.

 

Your style becomes clearer. Your quality bar goes up.

 

The way you describe your work starts to make sense to other people, especially clients.

 

You might still draw a range of subjects, but there’s a clear thread running through the work.

 

Someone can look at it and understand what you offer and where you fit.

 

For one person, focus might mean spending a month improving one specific skill and doing direct outreach with no social media.

 

For someone else, it might mean leaning into visibility and building an audience.

 

This is also where effort starts to feel different.

 

You’re not just putting work out and hoping. You’re improving specific skills that help you get hired.

 

You’re choosing one main way to be visible, instead of spreading yourself across everything at once.

 

To get through the dip, we also have to bring some of stage one back.

 

Not the experimental chaos, but the learning, curiosity, and the sense that you’re working on something specific and getting better at it.

 

We need to feel progress again.

 

This is where people learn with intent.

 

Pick one skill to improve. Solve one problem at a time. Choose one clear goal for the next few weeks or months.

 

It’s not just illustration. People do this with marathons, degrees, new careers.

 

For me, 2025 was learning how social media works.

 

For a lot of illustrators, this is the stage where progress becomes more meaningful. Fewer random wins, but more signs that things are stacking in a clear direction.

 

That’s how you get through the dip. Not by pushing harder, but by changing how you apply your effort.

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Stage 4: Momentum

 

Stage four is momentum.

 

This is the stage many people want when they’re starting out, but you might not even notice when it arrives.

 

Nothing suddenly clicks overnight. You don’t wake up famous or fully confident.

 

What changes is that things feel less random.

 

Clients recognise your work. You get repeat enquiries. Conversations become easier because people understand what you do and why they should hire you.

 

You’re still learning and still pushing yourself, but you’re no longer guessing in the same way.

 

Your effort compounds instead of resetting every few months.

 

Your confidence stabilises, not because everything is perfect, but because you’ve seen evidence your work has a place in the world.

 

Getting to this stage doesn’t mean doubts disappear or the work becomes easy.

 

It means you’ve built enough traction to keep going without constantly questioning whether you should stop.

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Closing thoughts and a small exercise

 

If you recognise yourself in stage two, trying but not making as much progress as you’d like, that doesn’t mean you’ve done something wrong.

 

It usually just means you’re not a beginner anymore, but you haven’t taken the next step into stage three.

 

The middle of a creative career can feel uncomfortable, slow, and full of uncertainty.

 

Trust me, I’m right there in it.

 

But it’s also where some of the most important career decisions get made.

 

You don’t need to do everything. You don’t need to panic.

 

You just need to decide what’s worth committing to, and give it enough time to work.

 

And if you’re in stage three or four, you don’t need to go backwards, but there’s a lot to be said for keeping a beginner mindset for as long as you can.

 

Learning new things is what keeps life interesting.

 

Maybe there is a stage five. I don’t know what that looks like.

 

You could imagine everything is perfect. Plenty of work, great clients, everything is easy, and you know exactly what you’re doing.

 

Sounds nice, but if there’s nothing left to learn and nothing left to aim for, we lose something important.

 

Every illustrator, and honestly every person I respect with a long meaningful career, stays curious. They still have ideas and want to try new things.

 

On the other hand, I’ve met a few people who’ve achieved a lot, think they know everything, and aren’t open to new ideas. And they’re mostly boring, insufferable arses.

 

So if you’re not happy with where you are now, that can actually be a good sign.

 

It means you still care, and you’ve got a lot to learn.

 

And as long as you don’t quit in stage two, there’s still a long and fulfilling path in front of you.

 

Before you click away, here’s one small thing I want you to do.

 

Take a bit of time after this video to think about one skill you know is worth committing to right now.

 

Not forever. Just for the next month.

 

Then, if you’re comfortable, write it in the comments. Just one thing.

 

Not because you owe anyone an explanation, but because stating it publicly makes it real and gets it out of your head.

 

I hope this video helped you make sense of where you are right now. And if you’re in the dip, it can get better.

 

You might enjoy this video next.

 

See you next time.