#59 / New Chapter, Same Curiosity
I'm stepping into the unknown (again)!
I’ve handed in my notice.
If you’re in Auckland, I’d love to catch up over coffee - no agenda, just a good chat about what’s next.
The real story isn’t one company’s drama; it’s a bigger theme: antifragility - thriving by leaning into uncertainty rather than avoiding it.
Nassim Taleb calls it the “Thanksgiving Turkey” problem. The turkey gets a free feast every Thursday and starts to believe life is certain - right up until the day before the holiday.
I’ve made a similar decision before, choosing to embrace uncertainty. Straight out of uni I quit a comfortable management role in China, stumbled through a rough startup year, wrote a book, built an app, spoke at Macworld, launched BearTalk, and eventually landed here in New Zealand. Tough choice, great return.
Now I’m at a new fork. After a rewarding spell in Auckland, the spark is fading and the market is shifting fast. I don’t want to miss the doors this moment might open.
The plan
Spend the next few months testing a handful of product ideas.
Level-up new skills - AI workflows, storytelling, you name it.
Meet interesting people, online and off. DM me if you’re one of them.
If nothing sticks, no drama - I’ll head back to the job market with fresh stories in my pocket.
Certainty is overrated. Here’s to the upside of the unknown.
Let’s connect - coffee in Auckland or Zoom worldwide.
video of the week: Never Lose Your Best ChatGPT Ideas Again With This Easy Trick!
Ever had a deep conversation with ChatGPT, only to forget everything the next day? You’re not alone.
In this video, I’ll show you how to turn your AI conversations into a powerful personal knowledge base—so you can save, search, and actually reuse the best insights from your chats. Whether it's research, creative ideas, or detailed reports, these conversations hold more value than we think.
I'll walk you through a simple 4-step system using tools like MWeb Pro, Calibre, and Readwise Reader. You’ll learn how to clean up your chats, export them as Markdown, convert them into ebooks, and store them in your favorite apps.
It’s a lightweight habit that gives massive returns—especially if you're using AI daily for thinking, learning, or content creation.
Hello, I’m Bear—a product designer, UX mentor and an award‑winning bilingual podcast host, currently living in Auckland, New Zealand. I enjoy sharing insights from my work, life, and study, helping all of us grow together.
Bear Academy Newsletter is my weekly email packed with thoughts on technology, design, and productivity—featuring book breakdowns, learning tips, and career reflections.
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