Welcome to the latest edition of Conversations with Simon, our weekly roundup of the best and most useful takeaways from Simon’s podcast, A Bit of Optimism.
This week features a special episode commemorating the 15th anniversary of Simon’s book, « Start with WHY. » To mark the occasion, Simon sits in the guest chair while renowned interviewer Cal Fussman takes over hosting duties. Their conversation covers a lot of ground, from Simon’s publishing journey to where his thinking is headed next.
Among the many exchanges was a particularly relevant discussion about AI and what it means for professionals like us who are figuring out how to integrate these tools effectively. You can view their conversation in full below, or listen here.
The Shortcut Temptation
Let’s face it—AI tools are getting impressively good at producing work that used to take us hours or even days. They can draft reports, generate code, create presentations, and even mimic specific writing styles with remarkable accuracy.
For busy professionals, these tools are tempting time-savers. But during the conversation, Simon offered a perspective that challenges our efficiency-first mindset.
« AI can only tell me what I’ve already thought, » Simon said. « It can’t tell me what I’m going to think. »
When discussing how AI might write content in his style, Simon noted that it would « go on and on about WHY this and WHY that and purpose. But I don’t talk about WHY anymore. That book came out 15 years ago. »
What Happens When We Skip the Process
When we create something ourselves—whether it’s a strategic plan, a presentation, or content for our teams—we don’t just end up with a finished product. We gain something more valuable.
« I am smarter, I’m a better problem solver, I am more resourceful, I am more curious, I’m a better pattern recognizer because I went through the awful process of writing the book myself, » Simon said.
He emphasized that « it’s not the fact that the book was written, it’s that I wrote the book. » This principle applies across all creative endeavors—the transformation happens through the struggle, not just in the finished product.
The Relationship Factor
This extends to our professional relationships in surprising ways. Simon shared a scenario about using AI to generate an apology after a conflict: « You go to ChatGPT and be like, ‘I’m an idiot. This is what happened. Please tell me what I need to say to do the right thing.’ »
Even if the AI provides the perfect response based on « all the therapy and all of the listening skills, » Simon pointed out a fundamental problem: « If she finds out that you got that from ChatGPT…it does not repair the relationship. »
The human element is too crucial. « I’d rather have a bumbly fumbly fight with you… imperfect because at the end of the day, I know we’re both trying to get to resolution versus you reading me the perfect script, » he said.
The Beauty of Imperfection
Simon introduced a concept that captures why human-created work remains valuable in the age of AI. « Wabi-sabi is a Japanese design concept that means beauty in that which is temporary or imperfect, » he said.
He described Japanese ceramics as « imperfect. They’re bumpy… the glaze is very often imperfect and messy. And they’re the most beautiful things in the world because you can see that it was made by hand. »
This applies to professional work too. Those slight imperfections aren’t flaws to be eliminated—they’re distinctive markers of authenticity that clients and colleagues respond to.
Finding the Right Balance
For those of us navigating careers in rapidly changing environments, the question isn’t whether to use AI tools—it’s where and how to implement them thoughtfully.
« Like everything, I think there’s positive and negative, » Simon acknowledged. « Any tool, and every tool comes at a cost. Sometimes those costs are worth it. Sometimes those costs are not worth it. »
This prompts us to consider which tasks benefit from technological efficiency without sacrificing valuable growth, and where AI might enhance capabilities rather than replace essential human development.
Playing the Long Game
For those focused on sustainable career growth, sometimes the journey matters more than the shortcuts. Simon’s framework of the « infinite game » applies perfectly here—distinguishing between those focused solely on immediate results versus those committed to continuous improvement over time.
« It’s the struggle that makes us a better version of ourselves, not the product, » Simon said. He posed a question worth reflecting on: « You are not growing as a person. And the question is, do you want to grow? Do you wanna be a different, better version of yourself when you’re 20, when you’re 30, when you’re 40, when you’re 50, when you’re 60? Or do you want zero growth? »
Professionals who thrive in rapidly changing environments aren’t just those with the most efficient tools, but those who maintain their capacity for growth and connection—even when technology offers an easier path.
What parts of your work have you found benefit most from the « human touch » despite technological alternatives? Your experiences help all of us navigate this balance more effectively.