The Stanford d-School is generally credited (along with IDEO) for creating Design Thinking as a discipline. This is where you think user-first, come up with ideas, try stuff, get feedback, learn as you go and iterate your way to a new solution.

This is one of the best diagrams to illustrate design thinking, and is from the page I link to in the first paragraph.

As you can see, it’s a bit of a never-ending cycle, that focuses very hard on user empathy and trying stuff out.

And a couple of lecturers at the d-School used it to create a course called Designing Your Life. Needless to say, it was insanely popular, so they wrote a book.

Aaaaand, because they’re nice people, they’ve also made some resources freely and publicly available. Which brings me to the Designing Your Life Odyssey – prototyping your future. In the DYL Odyssey, you come up with three paths you could potentially take in the coming five years:

1. The Expected Path – what’s likely to happen if you keep doing what you’re doing?
2. The Alternative Path – if what you’re doing right now fell in a heap, what’s something else you might do?
3. The Wildcard Path – you don’t need money, and you don’t care what people think. What do you do?

You can download a copy of their worksheet/template here if you’re interested.

Given this is all free and public, I decided to give it a go, with some help and encouragement from Chat GPT. I don’t know about anyone else, but I freeze when I see these sorts of empty worksheets and can’t think of anything!

This was my initial prompt: I want to do an Odyssey 5 year plan as outlined in Designing Your Life. Starting with the Expected Path, please ask me a series of questions to inform this path, and provide advice, and a structure I can map onto the plan template. Once I tell you the Expected Path is complete, we can move onto the others.

I then got a bunch of questions to answer around topics such as:

• Current role and direction
• Personal life
• Finances
• Creative work
• Professional development
• Impact and meaning.

After I answered all the questions, Chat GPT did its thing, and dubbed my version of this path “The Balanced Builder“. A calm, productive life where I build digital projects, support creative learners, and grow my writing craft—one project (and one walk) at a time. And it gave me a five year timeline for the template.

I then asked it to look at The Alternative Path; what I’ll do if I can no longer live the life I’m living today. This threw up a completely different set of questions on the following topics:

• Default safety net
• Reinvented self
• Location and lifestyle
• Creative outlet
• Finances
• Meaning and fulfillment

So you can see some crossover in the latter sections, but the first part is pushing me to think about quite different areas.

My alternative path is “The Global Educator” When the digital marketing well dries up, I pivot to teaching and coaching—sharing my knowledge with the next wave of creatives, wherever in the world that takes me. It’s actually pretty attractive. I got my 5 year timeline, then went for Wildcard!

This was tough. To the point where I couldn’t dream up answers to the initial set of questions Chat GPT gave me. So I went back with this prompt: I’m so used to making my dreams small, to always being ‘realistic’ and ‘practical’, I’m finding this really difficult. Are you able to help with some more prompts or questions, based on what you know about me, to open my mind up to the wilder dreams?

And THEN I started having some real fun! These are the prompts it gave me:

💫 1. The Life Swap Game – If you could temporarily swap lives with anyone for a year (famous or not), whose life would you want? What about that life appeals to you?

🪄 2. The Wand Test – If I handed you a magic wand and said, “You’ll be amazing at whatever you choose,” what would you try doing that feels too risky right now?

🎭 3. The Dramatic Reinvention – If you had to completely rebrand yourself in 6 months, what persona would you take on? (e.g. best-selling author living in a cottage by the sea, global AI-for-creatives speaker, editor of a magical realism anthology…)

✈️ 4. The Living Postcard – Where in the world could you imagine yourself living a new chapter? What does your day look like there? Who are you meeting? What are you building?

📚 5. The Reverse Regret Test – Imagine it’s 2030, and you’re reading a version of your biography where you never did the Wildcard Path. What do you regret not trying?

🎙️ 6. The “Secret Life” Reveal – You’re on a podcast in five years, sharing how you totally changed your life. The host says: “Wow, what a transformation!” What story do you tell them?

So, after all that, I have a Wildcard path called “The Global Creative Catalyst” A visionary life built around storytelling, strategic transformation, and beautiful living—balancing travel, creativity, and connection with work that inspires both me and others. It’s pretty fab, I have to say.

It then suggested downloading pdf summaries and so forth, but these weren’t terribly good. It was the detail in the 5 year timelines (and frankly, the thought exercise in answering the questions) that made this a fun and valuable activity.

The final part of the Odyssey exercise is to look at the gauges on the worksheet and think about how possible, interesting, and likely each path is, along with any questions they raise. This is obviously a ‘you’ thing rather than an AI thing, and that’s exactly as it should be.

What do you think? Is this something you’re keen to try? If you do, please drop me a note at hello@aiforsquishyhumans.com and let me know what you found, and what your paths are!