Podcast Summary: "We’re Good at Failing (and You Can Be Too) 🤣 The Power of Experiments"

Podcast: The Good Ship Illustration
Hosts: Helen Stephens, Katie Chappell, Tania Willis
Date: November 14, 2025
Episode Theme: Embracing experiments and "failure" as a crucial part of a creative illustrator’s career.

Overview

In this insightful and lighthearted episode, the hosts of The Good Ship Illustration—Helen, Katie, and Tania—dive into the power and permission of creative experimentation. Sharing stories of their own "failed" projects, tangent career paths, and unexpected wins, they unpack how letting go of perfection and embracing short-term experiments is not just possible but essential for illustrators. Through candid banter and practical advice, they encourage listeners to try new things, drop what isn’t working, and treat the creative career as a joyous (and sometimes messy) lab.

Key Discussion Points & Insights

1. The Joy (and Reality) of Trying Ideas

• Excitement About New Ideas (00:30):
  • All three love the rush of new creative ideas, but dread the pressure of long-term commitment.
    • Katie: “If you tell me that it’s an exciting idea, but then I must commit to it for an indefinite amount of time—kiss of death.” [00:38]
    • Group consensus: Experiments are far easier to embrace than life-altering commitments.

2. Learning from Failed or Dropped Experiments (00:56—02:24)

• Katie’s Experiment with Running an Agency:

  • Tried scaling her business, having a big team, and realized it was not for her—felt compelled to try, but happier scaling back.
    • Katie: “It was an experiment I just didn’t like doing. It was stressful.” [01:00]
  • Undoing an experiment isn’t a failure: “Canceling the experiment and taking it back to how it was when you were having a good time again is good because then you’ve learned the thing.” [01:30]

• Tania on Generational Perfectionism:

  • Always taught to get things perfect or not try at all; learning from the others that ‘soft launches’ and time-limited experiments are healthy.
    • Tania: “You’re not married to it and you can just change your mind.” [01:40]

3. Experimenting Beyond Art: Repurposing Work

• Tania’s New Venture (02:42):
  • Shifting from seeking new commissions to selling prints of her existing work (maps) in shops—taking charge, not waiting for others.
  • “...I’ve realized, no, I’ll be in charge. I don’t have to wait for someone else to do it.” [03:12]
• Advantage: Greater control over print quality, copyright, and income streams.

4. Career Detours, Collaborations & Human Design

• Reluctance and Personality (04:16):
  • Tania jokes she was "dragged" into Good Ship by Helen and Katie, reflecting on her Human Design type (Generator: responds best to invitations).
    • “I’m much better if I’m invited to do something.” [05:00]

5. Personal Fails, Automation Gone Wrong (05:23–08:19)

• Helen’s Attempt to Automate School Visits:

  • Tried to digitize school visits during lockdown—a logistical nightmare for schools’ payment systems.
    • Helen: “It did not work. It just did not work. Because what I didn’t consider is schools cannot pay for anything online… So every time I had a school interested, they would say, ‘Please can you send me an invoice and we’ll send you a check.’ And it completely ruined the whole idea because it just took so much work.” [05:54]

• Pivot to Giving Value for Free:

  • Ended up giving away content for free rather than dealing with mountains of admin. Positive creative feelings outweighed practical hassle.
    • “Decided it was way better just to give it away for free than have to invoice a school and wait for a check and then take the check to the bank.” [07:41]

6. Technology and Process Experiments

• Digital Art Phase (07:41–08:19):
  • Helen got obsessed with digital art (Procreate, Photoshop), producing books—but eventually returned to loving traditional media.
    • “I’m out the other side of that experiment now and I’m really, really into doing paper again.” [08:15]

7. The Value of Following Through (08:30–09:46)

• Persistence vs. Flakiness:
  • Tania admires Helen’s determination to thoroughly explore experiments before pivoting.
    • “You’re not a kind of… you don’t drop at the first sign of trouble… So unflaky. That’s—I'm scared to death about being flaky about things.” [08:30]

8. Community and Free/Paid Content Experimentation

• Substack & the “Pay What You Can” Model (08:53–10:23):
  • Inspired by the Blind Boy podcast, Helen shifted her Substack to a pay-if-you-can model, aiming for accessibility and community.
    • “Those that can’t afford it can still listen because those who can afford it, pay for it. And that makes a nice community.” [09:08]

9. Pre-Good Ship Experiments & The Power of Partnership

• Katie’s “Bullet Journal Gang” & “Productivity” Course (10:23–12:10):
  • Early online experiments provided valuable skills for later collaborative projects.
    • “But all those experiments—you learn so many things.” [10:52]
  • Realized working collaboratively is less exhausting and more sustainable than solo efforts.

10. Serendipity, Geography & Creative Chemistry

• The coincidence of all three hosts living in the same town, with complementary skills, is likened to forming “The Beatles of illustration.” [12:29–13:12]
  • “We had the starter, we had the main and the dessert together and it’s a dinner party.” [11:56]

11. Small Experiments That Stuck: “Art Club”

• Tried a one-off live "Art Club" on Friday nights during lockdown. It was so fun and popular they ended up running weekly events for years.
  • “We did it. We were so nervous… Realized something like 500 people had been watching. And then we said, should we do it again? And we’re still doing it.” [13:53–14:19]

12. Challenge: Do Your Own Experiment!

• Tania considers herself unexperimental, but the others disagree and challenge her (and listeners) to try something new for a set period—specifically, three months, even something as small as one post a month.
  • Katie: “If you give yourself three months and even if you only did one post per month for three months and just saw what happened.” [16:20]
  • Tania accepts, with Katie as accountability buddy [16:31–16:46].

13. Permission to Change Your Mind (17:10–17:17)

• The look and content of your creative output (website, newsletter, etc.) can be tweaked and updated anytime—nothing needs to be perfect at launch.

14. Resistance to Being Told (18:26–19:17)

• Hilarious group realization: If someone else tells them to do something, immediate resistance follows, even if they were about to do it anyway.

Notable Quotes & Memorable Moments

• On the power of trying:

  • Katie (on ending failed experiments): “Canceling the experiment and taking it back to how it was when you were having a good time again is good because then you’ve learned the thing.” [01:30]

• On experiments vs. perfection:

  • Tania: “Maybe because of my generation where everything had to be set up perfectly… But you just give it a go. Maybe give it three months, put a deadline on it. If it’s not working the way you want it to, then just rethink it and cancel it, start again in a different direction.” [01:40]

• On digital school visits and admin nightmares:

  • Helen: “It did not work. It just did not work. Because… the council will send the illustrator a check. Like they do it in such old fashioned ways… it completely ruined the whole idea.” [05:54]

• On collaborative magic:

  • C: “All of those things are quite spooky, actually. That they were already in place and each of us had a different input into what we needed to make a course. It was like we had the starter, we had the main and the dessert together and it’s a dinner party.” [11:58]

• On the spirit of experimentation:

  • Helen: “Experiments are important because sometimes they work better than you can even imagine.” [14:33]

• On commitment to an experiment:

  • Katie: “For an experiment, you kind of have to get married to it for a set amount of time… That’s not a real experiment otherwise.” [15:19]
  • Tania: “That’s being flaky. And that’s the scariest thing of all. This has to be a commit for a bit.” [15:31]

Important Timestamps

• 00:30 – Excitement about new ideas versus commitment dread
• 01:00–01:30 – Katie’s “failed” agency experiment
• 01:40–02:24 – Tania on perfectionism and learning to experiment
• 03:12 – Tania’s new plan for selling existing work
• 05:23–07:41 – Helen’s failed automated school visits experiment
• 08:15 – Moving from digital to paper art
• 08:53–10:23 – Experimenting with pay models on Substack
• 10:23–12:10 – Pre-Good Ship experiments and realizing the value of collaboration
• 13:53–14:33 – Art Club: spontaneous experiment that became a tradition
• 16:20–16:46 – The three-month experiment challenge for Tania
• 17:10–17:17 – Permission to update your creative "brand" anytime
• 18:26–19:17 – Group laughing at their resistance to being told what to do

Actionable Takeaways

• View your business, creative projects, and even social media as experiments with optional expiry dates—none are final.
• Try something new for a set short period (e.g., three months), then honestly review.
• Working in community or with accountability partners helps experiments last and feel less daunting.
• It's okay to change your mind, rebrand, or pause—no creative effort is wasted.
• Let fun (not just market logic) lead your experiments—and share your results!

Community Invitation

The hosts close by encouraging listeners to share their own "mad experiments" and results, whether triumphant or quietly faded away.
“Let us know what your experiment is as well, because we’re all really nosy.” [19:40]

Instagram Replay: @thegoodshipillustration
Missed Art Club or want to see previous experiments? Replays are available on their Instagram.