Calypso Rose is an award-winning entrepreneur, author and co-founder of OffScript. She talks about the future of work, AI, entrepreneurship and why waiting to be picked is a terrible career strategy. Having started her first company at 19, she has built, sold and spectacularly flopped businesses. Nothing is airbrushed. Everything is useful.
Nine subjects with real stories behind them. Open one.
Why asking a 16-year-old to choose one career for life makes increasingly little sense. What "safe" even means now. And why not knowing what you want to do can be genuinely useful.
What happens when thousands of people submit equally polished, AI-assisted applications. How young people become visible without gimmicks. Why making and showing something beats endlessly polishing a CV.
What AI does brilliantly. What it cannot replace. Why AI should extend your thinking, not do your thinking for you. Use the tool. Keep your taste.
What happens when a young person moves from endlessly scrolling to actually making something. Small websites, newsletters, events, videos, projects, businesses: proof, in any form.
Not about everybody becoming a founder. Curiosity, initiative, problem solving, experimentation and not waiting for permission. Useful whether you start a company or never do.
Businesses working, businesses failing, recessions, running out of money, pivots and knowing when to stop. Calypso has done all of them, and will happily say which lessons only had to be learnt once.
Money as a tool rather than the entire point. Earning, choices, autonomy, and the online promise of quick money. What variety, adventures and hobbies are actually worth.
Networking without the horrible word "networking". Why opportunities usually come through people, and how to start building relationships before you think you have a network. Ask for 20 minutes, not a job.
Calypso speaks directly to teenagers about careers, AI and work. A useful window into what young people are actually worried about, excited by and confused about, straight from the room.
Please Don't Pick a Sensible Career is told entirely from Calypso's point of view. Her businesses, her mistakes, her opinions and the things she wishes someone had told her earlier. Along the way, she brings in entrepreneurs and people who have built things, changed direction, taken risks and got plenty wrong themselves.
She wrote it with her mother, Clare Hastings, who started her career working for Anna Wintour at Harpers & Queen and spent more than 30 years as a fashion journalist, stylist and costume designer before becoming an author herself. Calypso and Clare have also worked together, in one form or another, since Calypso was 14.
So this is not two generations taking turns to give careers advice. It is Calypso's voice, sharpened by Clare, with stories and opinions from entrepreneurs throughout. A book about work written by two people who have spent rather a lot of time doing it, changing it and occasionally getting it wrong.
Started her first company at 19. Since then she has built and sold businesses, won multiple awards, worked through recessions, raised investment, launched new ideas and started again more than once. Took investment for The Good Times Card and watched it fail anyway. Some lessons only needed learning once.
Now she runs OffScript, works with young people around work and entrepreneurship, and has written the field guide she wishes she'd had at 16.
She has done the thing. She has also got the thing spectacularly wrong. Both are useful.
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