Do you ever get the sense that no matter how much you do, you’re still running out of time? Like there’s something you should be doing, but you can’t quite figure out what it is?

In this episode of How I Work, we sit down with New York Times bestselling author Chris Guillebeau to talk about a feeling so many of us carry but rarely name: time anxiety. From guilt over unread emails to the pressure to leave a legacy, Chris shares the practical strategies that helped him stop chasing time – and start living with more calm and clarity.

In this episode:

• What time anxiety is—and why so many of us feel it without even realising

• How Chris let go of the pressure to leave a legacy

• A weekly “time decluttering” ritual that can clear your calendar

• Why “just prioritise better” is the worst advice

• The bold email strategy Chris swears by (even if it ruffles a few feathers)

• Why leaving 10–15 minutes of buffer time between commitments can change everything

Key Quotes:“You have to decide for yourself what is enough.”

“It’s not about being an email ninja – it’s about understanding what matters.”

Connect with Chris on Instagram, X (Twitter), and LinkedIn and his website, Listen to his podcast Side Hustle School, and check out his latest book Time Anxiety.