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This is the seventh Captn OffScript bonus, and the last one of Season 2. After a main episode spent in the trenches, I asked Simon Flöter one question that flips it all upside down: if you woke up tomorrow with complete financial stability, never worrying about money again, what would you work on?
It went to newsletter subscribers first as a private YouTube link. Today it's available here too.
His first answer: he'd finish things. And then he told me about the letters. His father found a bundle his grandfather wrote to his grandmother, from 1930s Germany onwards, love letters mixed with the small facts of daily life. Simon barely knew him. His dream is to turn them into what he calls an online timepiece: the letters sorted so they read like a book, searchable, with the old words and the history behind each moment explained as you read. Two people in love, talking to each other across the darkest of decades, with the human side of it, in his words, kind of beautiful. Also on the list: fusing his design, code and illustration into something that doesn't exist yet, a zine with friends, and the video game he's always wanted to make.
In this conversation we talked about:
The main episode this bonus extends: S02/E38 — Simon Flöter on Life in the Trenches & Not Making Decisions From Fear https://captnoffscript.com/s02-e38-simon-floter-life-in-the-trenches
Find Simon here:
Find me here:
If this resonated, listen to: Kristof Devos (S02/E31) — another conversation about making things for the joy of making them.
This was the final Captn OffScript bonus of Season 2. Newsletter subscribers get every bonus on YouTube a week before it reaches the podcast feeds. Subscribe at https://captn.myflodesk.com/newsletter to get them first when the show returns.
For the final episode of Season 2, I didn't want a victory lap. Simon Flöter is a German illustrator, designer and developer living in Amsterdam, and he told me early on: this is not a success story. This is from the trenches.
His commercial illustration work vanished this year, and he suspects AI swallowed it. Money got extremely tight. He just landed a job that should carry him through the rest of the year. And through all of it, he kept drawing, the way he has since he was a kid tracing Batman comics and getting rejected from every art school he applied to. We talked about the trenches most designers are actually in right now, why the anger at AI is really anger at corporate greed, and his advice that gives this episode its title: never make decisions from fear.
In this episode:
Find Simon here:
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The final Friday bonus of the season: I asked Simon what he'd work on if money stopped mattering tomorrow. His answer involves his grandfather's love letters from 1930s Germany, a zine with friends, and a video game. Newsletter subscribers get it first, a week before it's public. Subscribe at https://captn.myflodesk.com/newsletter.
If you enjoyed this episode, leaving a 5-star rating on Apple Podcasts or Spotify takes less than a minute and helps more people find the show. I'd be incredibly grateful.
If you liked this episode, listen to: Martyna Wędzicka (S02/E33) — another conversation about holding onto your own way of working when everything pushes you to compromise.
That's Season 2. Thank you for listening to every conversation, the big names and the trenches alike.
This is the sixth bonus episode of Captn OffScript. In Halli Thorleifsson's main episode we covered everything he's built: the agency he sold to Twitter and rebuilt, the almost 2,000 wheelchair ramps, the tax he chose to pay. This is the conversation about what he's been rebuilding underneath it all, himself, in his words, brick by brick.
It went to newsletter subscribers first as a private YouTube link. Today it's available here too.
When Halli stopped drinking, he stopped the numbing but never went looking for what he'd been numbing. It took more than twenty years to come back to it. The hard things in his life, his disease, losing his mother young, had each gone into a box he never looked into. A survival technique that worked as a kid, and quietly stopped working as an adult. So he opened the boxes: two to three years of therapy, physical and mental, and, gradually and with help, letting the numbness lift after two decades. He's honest that nothing is fixed, that he's holding himself together mostly, and that he's better equipped than he's ever been. This is his path, not a template, and he shares it with an honesty very few people manage.
In this conversation we talked about:
Timestamps: No chapters for this bonus.
The main episode this bonus extends: S02/E37 — Halli Thorleifsson on Building Ueno Twice & Designing Things People Actually Use https://captnoffscript.com/s02-e37-halli-thorleifsson-building-ueno-twice
Find Halli here:
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If this resonated, listen to: Andy J. Pizza (S02/E30) — another honest conversation about the slow inner work behind a creative life.
This was the sixth Captn OffScript bonus episode. Newsletter subscribers get future bonuses on YouTube a week before they reach the podcast feeds. Subscribe at https://captn.myflodesk.com/newsletter.
This is the fifth bonus episode of Captn OffScript. When Teresa Ferreira and I recorded her main episode, we got into imposter syndrome and self-worth, and it was honest enough that I kept it back for this.
It went to newsletter subscribers first as a private YouTube link. Today it's available here too.
Teresa's first point is the most reassuring one: imposter syndrome doesn't go away. Not with success, not with experience. You just get better at spotting it. Her tool for catching it is a question I've been repeating ever since, whose voice is that? Because the critical voice is almost never yours. It's usually something someone said to you growing up that you've disproved a hundred times since. We also got into why creatives tie their whole self-worth to their work, her brilliant line that nobody who looks after trees feels worthless when one doesn't grow, and the thing I admitted out loud: I check my stats most mornings before I've done anything else. The numbers don't measure you. They never did.
In this conversation we talked about:
Timestamps: No chapters for this bonus.
The main episode this bonus extends: S02/E36 — Teresa Ferreira on Digging Her Way Into Design & Letting Go of the Perfect Day https://captnoffscript.com/s02-e36-teresa-ferreira-digging-into-design
Find Teresa here:
Find me here:
If this resonated, listen to: Andy J. Pizza (S02/E30) — another honest conversation about self-worth and untangling who you are from what you produce.
This was the fifth Captn OffScript bonus episode. Newsletter subscribers get future bonuses on YouTube a week before they reach the podcast feeds. Subscribe at https://captn.myflodesk.com/newsletter.
Haraldur "Halli" Thorleifsson built the design agency Ueno from nothing, sold it to Twitter in 2021, and made a decision almost nobody makes: he structured the sale so he'd pay as much tax as possible, in Iceland, on purpose. Because Iceland is the country that gave a kid from a poor family with muscular dystrophy the chance to build something in the first place.
Then he started Ramp Up, which has put almost 2,000 wheelchair ramps across Iceland and is now expanding to Ukraine and Panama. And six or eight months ago, he rebooted Ueno to work on design in the AI era, because, in his words, he was bored, and his brain needs a problem to chew on. This was not the lightest conversation I've had on the show. It might be one of the most worth your time.
In this episode:
Timestamps: 00:00 Meeting Halli Thorleifsson 00:40 Choosing to pay the tax in Iceland 06:40 Growing up poor with muscular dystrophy 09:29 Starting Ramp Up, and the world as decisions 12:06 Progress, and the case for impatience 14:52 The Musk moment, and perception vs reality 16:30 What he's building now, and getting humbled by users 18:59 Why he rebooted Ueno 24:05 What AI means for young designers 27:47 Sharing a studio with his artist wife 31:19 Getting sober, the decision that changed everything 33:13 New York, Tokyo and the cities that shaped him 35:03 What children force you to become 41:56 Creativity as building his own world 43:18 The sweater he can't unravel 45:54 What people should know about Iceland 49:15 Advice to eight-year-old Halli
Find Halli here:
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This week's Friday bonus: Halli and I go deeper into the rebuilding: rebuilding yourself brick by brick, the boxes he packed away as a kid and never looked into, and what surfaced when the numbness lifted after 20 years. It goes to newsletter subscribers first, a week before it's public. Subscribe at https://captn.myflodesk.com/newsletter.
If you enjoyed this episode, leaving a 5-star rating on Apple Podcasts or Spotify takes less than a minute and helps more people find the show. I'd be incredibly grateful.
If you liked this episode, listen to: Radim Malinic (S02/E34) — Halli says creativity let him build a world he wanted to live in; Radim's episode is the other side of that same coin.
Some people walk a straight line into design. Teresa Ferreira dug her way in, through archaeology. She was born in Lisbon, spent part of her childhood in Macau, has lived in London for nineteen years, ran design at the Financial Times, and now runs her own studio, Ferrgood. When I said she felt like the whole world in one person, I wasn't exaggerating.
What I didn't expect was how much of this conversation would be about slowing down and letting go. Teresa was talked out of art as a kid, found her way back through archaeological illustration, burned out twice, and eventually learned to release the idea of a perfect day that had been quietly setting her up to fail every single evening.
In this episode:
Timestamps: 00:00 Meeting Teresa Ferreira 01:25 Growing up between Lisbon, Macau and London 04:04 The unlikely path from archaeology to design 10:35 Moving into graphic design and the Financial Times 13:00 Building brands that last 16:50 Self-doubt, and leaving the safety of big brands 19:28 Burning out, twice 25:03 The perfect balanced day 29:48 Letting go of perfectionism 33:43 Choosing a slower life 40:24 Journaling and daily practice 46:13 The drawing she'd keep, and advice to young Teresa
Find Teresa here:
Find me here:
This week's Friday bonus: Teresa and I go deep on imposter syndrome, why it never goes away, how to catch it by asking "whose voice is that?", and why the numbers have nothing to do with your worth. It goes to newsletter subscribers first, a week before it's public. Subscribe at https://captn.myflodesk.com/newsletter.
If you enjoyed this episode, leaving a 5-star rating on Apple Podcasts or Spotify takes less than a minute and helps more people find the show. I'd be incredibly grateful.
If you liked this episode, listen to: Kristof Devos (S02/E31) — another conversation about slowing down, resisting the hustle, and building a calmer creative life.
This is the fourth bonus episode of Captn OffScript. When Gemma O'Brien and I recorded her main episode, we got into burnout and flow, and I held that part back for this.
It went to newsletter subscribers first as a private YouTube link. Today it's available here too.
Gemma has talked about burnout in a lot of other interviews, so I didn't want to rehash it. What I wanted, as someone who leans towards overworking, was the thing underneath it: how she sees it coming, and what she actually does about it now. Her answer was calmer than I expected. She's made peace with burnout by treating it as information about her process rather than a catastrophe. She talks about a sweet spot, too much work and you burn out, too little and you're bored and understimulated, and about looking after the foundations: sleep, rest, human connection, nature. Then we got into flow, which she's now studying formally, reading neuroscience papers on the very thing she's spent her life inside. Her line on it: she's like a chef who cooks an incredible meal for someone else, then comes home and eats McDonald's.
In this conversation we talked about:
Timestamps: [Awaiting confirmation]
The main episode this bonus extends: S02/E35 — Gemma O'Brien on Getting Bored of Herself & Refusing to Pick One Thing https://captnoffscript.com/s02-e35-gemma-obrien-bored-of-herself
Find Gemma here:
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If this resonated, listen to: Radim Malinic (S02/E34) — another conversation about overwork, the cost of doing too much, and learning to look after yourself.
This was the fourth Captn OffScript bonus episode. Newsletter subscribers get future bonuses on YouTube a week before they reach the podcast feeds. Subscribe at https://captn.myflodesk.com/newsletter.
This is the third bonus episode of Captn OffScript. When Radim Malinic and I recorded his main episode, the conversation about fear came near the end, and it was good enough that I kept it back for this.
It went to newsletter subscribers first as a private YouTube link. Today it's available here too.
It's short, and it's the most reassuring thing I've put out in a while. Radim used to think you could unlearn fear, get rid of it entirely, and then realised you can't. Fear isn't a fault in the system. It's the system doing what it was built to do. We've been wired by evolution to look out for things that could kill us, and that wiring hasn't changed even though the threats have. So when you think about sharing your work with a thousand strangers, your body runs the exact same programme it would run for a sabre-tooth tiger in the bushes. Same mechanism, same flood of fear. The line I'd want you to keep: when you freeze, ask whether the tiger is actually coming. Most of the time, it isn't.
In this conversation we talked about:
The main episode this bonus extends: S02/E34 — Radim Malinic on Creativity as Escape & Becoming More of Who You Already Are https://captnoffscript.com/s02-e34-radim-malinic-creativity-as-escape
Find Radim here:
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If this resonated, listen to: CJ Cawley (S02/E32) — another conversation about doing the work and putting yourself out there even when everything tells you not to.
This was the third Captn OffScript bonus episode. Newsletter subscribers get future bonuses on YouTube a week before they reach the podcast feeds. Subscribe at https://captn.myflodesk.com/newsletter.
Gemma O'Brien is a lettering artist, a fine artist, a muralist, and most recently a student of neuroaesthetics. She's painted a billboard in Times Square, had work acquired by a museum, and she has a public Strava profile on her website, because running is as much a part of her as the lettering is. I'd been trying to get her on the show for a long time, and the hardest part was knowing where to start.
So we talked about how someone ends up doing this many things at once, and why she has no intention of narrowing it down. The line that stayed with me: after ticking off every career goal she'd ever dreamed of, she went back to university because she'd grown "almost bored of myself."
In this episode:
Find Gemma here:
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This week's Friday bonus: Gemma and I go deeper into burnout and the flow state, the hidden cost of doing this much, and what it takes to protect your focus. It goes to newsletter subscribers first, a week before it's public. Subscribe at https://captn.myflodesk.com/newsletter.
If you enjoyed this episode, leaving a 5-star rating on Apple Podcasts or Spotify takes less than a minute and helps more people find the show. I'd be incredibly grateful.
If you liked this episode, listen to: Jessica Hische (S02/E21) — another lettering artist on building a creative life on her own terms, and why imposter syndrome never fully goes away.
This is the second bonus episode of Captn OffScript. When Martyna Wędzicka and I recorded her main episode, we spent most of it on the past and the present. But right at the end, I asked her where she's heading next, and the answer was so warm and so hopeful that I held it back for this.
It went to newsletter subscribers first as a private YouTube link. Today it's available here too.
It's a short one, and a lovely one. Martyna noticed a pattern in her own career: roughly every four to five years, she rediscovers herself and her style. She thinks she's at the edge of one of those cycles right now, and the next thing turns out to be knitting. Her husband calls what she makes "her posters, made of yarn." She talks about fabric as another canvas, the same design thinking carried out in a different material, and about choosing the handmade on purpose as a counterweight to AI. And then the line I can't stop thinking about: graphic designers don't retire.
In this conversation we talked about:
The main episode this bonus extends: S02/E33 — Martyna Wędzicka on Being Weird, Polish Design & Why You Can't Rush Your Style https://captnoffscript.com/s02-e33-martyna-wedzicka-being-weird-style
Find Martyna here:
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This was the second Captn OffScript bonus episode. Newsletter subscribers get future bonuses on YouTube a week before they reach the podcast feeds. Subscribe at https://captn.myflodesk.com/newsletter.
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