How to plan your career when AI is changing everything 🤖

This week, I’m in San Francisco, delivering a few workshops for a university. My client is helping its students plan their careers as AI reshapes the workforce and the world.

I’m a Designing Your Life Certified Coach, so I thought I’d bring in design thinking to help these students tackle the challenge.

The workshop centers on design thinking. In addition to facilitating this powerful technique in group settings, I often use it with one-on-one clients because it breaks a big career decision into bite-sized steps, so it feels far less overwhelming.

Product teams use design thinking to build and test new ideas. Applied to your career, it means sketching a few possible paths and testing them in small ways before you commit to one.

Design thinking also tackles a myth I cover in the workshop: that there’s one right career, and your job is to find it.

The average person holds roughly 13 jobs from ages 18 to 58, according to the U.S. Bureau of Labor Statistics.

Try this bite-sized homework from the workshop:

✏️ Define it: What do you need in your next role?
✏️ Ideate it: If your current path disappeared tomorrow, what would you do instead?
✏️ Prototype it: Who’s one person you could talk to about that path this week?

Hit REPLY and share your answers to any of these questions. I promise you that I read every single message.

If your answers point you toward a new path, think micro-pivots rather than massive leaps.

👉🏼 Ready to test a new path? Explore 6 steps to successfully pivot within the tech industry.​

Have a fabulous week!

~ Kyle | CaffeinatedKyle.com​

P.S. If this sparked something in you, and you’re at a career crossroads, I’d love to help you design what’s next. I’m currently booking new coaching clients for late October 2026 and beyond. Schedule a consultation now to explore whether coaching is right for you.