How to Self-Sabotage Like a Pro

Ah, success. That terrifying, mythical beast lurking just beyond the safe, cozy realm of artistic struggle. We spend years pining for it, yet the moment we get a whiff of its approach—maybe a big commission, a viral post, an email from someone important who isn’t the electricity company —we suddenly find ourselves gripped with existential dread.


W is for Water Deer

Whether your name starts with W, you have an inexplicable fondness for fanged wildlife, or you just think water deer might be your long-lost spirit animal, this mug is for you. Featuring my quirky hand-drawn illustration of the elusive water deer—also known as the “vampire deer”—this design brings a touch of the wild (and wonderfully weird) to your morning coffee or tea.

What’s the thing you’re most scared to do? What would it take to get you to do it?

Succeed…

What if I can’t live up to expectations? What if I hate the person I become? What if I make a lot of money and have to learn how taxes work?

It’s funny how artists spend so much time fearing failure, only to discover that success is equally (if not more) horrifying. Failure, at least, is familiar. We know how to scrape by, how to romanticize the starving artist struggle, how to justify working for exposure because “one day it’ll pay off.” But success? That’s uncharted, uncomfortable territory.

What Does Success Even Mean?

Before we start spiraling, let’s define the enemy. Success isn’t one-size-fits-all. For some, it’s making enough money from their art to quit their soul-sucking day job. For others, it’s simply having the freedom to create without worrying about bills or algorithms. Some people want fame; others just want to be able to afford the fancy brand of coffee instead of the sad discount sludge that tastes like regret.

The point is: success is whatever you decide it is—but beware, because your brain might try to trick you into thinking it’s something unattainable. If your definition of success involves winning an Oscar, a Pulitzer, and becoming the Supreme Ruler of the Art World by next Thursday, you might want to scale things back a bit.

Why Are We Afraid of It?

The fear of success is sneaky because it doesn’t show up wearing a name tag. Instead, it disguises itself as procrastination, imposter syndrome, or a sudden, overwhelming urge to clean the entire house instead of working on that new project. It whispers lies like:

  • “If I succeed, I’ll have to keep succeeding.”
  • “People will realize I’m a fraud.”
  • “I’ll lose my artistic integrity and become a sellout who paints the same thing over and over because it pays the bills.”
  • “I’ll have to do public speaking.” (This one is particularly horrifying.)

At its core, the fear of success is the fear of change. Even if your current situation is miserable, at least it’s predictable. Success means stepping into the unknown, and the unknown is terrifying—especially for an artist whose comfort zone includes existential dread, caffeine, and staring at a blank canvas for hours.

How to Overcome the Fear (or at Least Outsmart It)

  1. Redefine Success in a Way That Doesn’t Make You Want to Vomit
    Instead of aiming for world domination, aim for something smaller and more sustainable. Maybe success is selling one print this month. Maybe it’s finishing a new piece without having a nervous breakdown. Set goals that don’t send you into a spiral of panic.
  2. Accept That Success Is Just Another Problem to Solve
    You think success means all your problems vanish? Ha! No. You just get new, shinier problems. Instead of worrying about whether you’ll ever make money, you’ll worry about keeping up with demand. Instead of struggling for recognition, you’ll struggle with expectations. Accept that problems are a part of the process, and no version of success will free you from occasional meltdowns.
  3. Get Comfortable with Discomfort
    Success means growth, and growth is uncomfortable. If you feel like you’re out of your depth, congratulations! That’s how you know you’re doing something right. Every successful artist was once a terrified mess who had no idea what they were doing. (Some of them still are.)
  4. Remind Yourself That Selling Art Isn’t Selling Your Soul
    You’re not a sellout for making money. You’re not a fraud for wanting recognition. Your art doesn’t become less meaningful just because people actually want to buy it. (And if you’re still worried, just make a side project that’s pure chaos and keeps your artistic soul happy.)
  5. Visualize the Worst-Case Scenario
    No, really. Imagine you succeed wildly beyond your dreams. What’s the worst that could happen? You have too many commissions? You get an awkward award speech moment? You become an eccentric millionaire who owns a pet peacock and only communicates in riddles? Most of these “terrifying” outcomes aren’t actually that bad. (Except for public speaking. That’s still terrible.)
  6. Take the Next Step Anyway
    Fear doesn’t go away just because you understand it. The trick is to move forward despite it. Feel the terror, the imposter syndrome, the existential nausea—and keep going. The more you push through, the more you’ll realize success isn’t a monster; it’s just another weird, unpredictable chapter in the artist’s journey.

Final Thoughts

Success isn’t some perfect, glittering endpoint where you’ll suddenly have it all figured out. It’s messy. It’s weird. It’s full of ups and downs. But it’s also proof that you’re doing something right—that your work means something, that people connect with it, and that your childhood dream of making a living as an artist wasn’t as ridiculous as everyone said.

So, the next time success starts creeping up on you and your instinct is to run, self-sabotage, or disappear into the comforting arms of procrastination—take a deep breath, laugh at the absurdity of it all, and remind yourself: this is what you wanted, remember?

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