When I first began exploring value — and experimenting with value-based questions — I often battled a sense of not feeling entitled to ask them. For many years, I assumed it was simply a matter of mustering courage. That belief partly inspired the book I co-authored back in 2012, “The Courage to Ask”.

With hindsight, I can see what I couldn’t then: my own self-worth had far more influence than I realised. My search for external validation kept tripping me up.

But one thing remains true: asking value questions does require courage.

Even a simple line such as, “Before we wrap up, what was most useful about this meeting for you?” demands a moment of bravery. So do many of the questions we’ve been discussing lately — including the ones people now practise on AI.

In The Courage to Ask, we emphasised that courage grows through action, not rumination. It’s a “from the legs up” process. Like going to the gym, you build the muscle by showing up, starting small, and repeating the reps.

And courage is going to matter even more in the years ahead. There are plenty of sophisticated ways to avoid it:

• Endless scrolling and fact-gathering instead of deciding. (AI now makes this an even bigger temptation than social media ever did.)

• Isolating behind screens. I regularly meet professionals who haven’t spoken to another human all day.

• Using AI as a substitute for human brainstorming. I’ve noticed how quickly I now get ideas from ChatGPT instead of picking up the phone.

• Avoiding the discomfort of social interaction — especially when not everything (or everyone) suits our preferences.

Homework: Building Your Courage Muscle

As we wrote back in 2012, courage only exists when apprehension is present. No discomfort, no courage. Which means building courage inevitably requires leaving the comfort zone — ideally in small, frequent steps.

Here are a few ways to train that muscle:

• Have more value-focused conversations — perhaps to test or refine a value proposition.
• Ask context questions at the start and end of meetings.
• Schedule a regular “AI Power Hour” (or half-hour) even when you don’t feel like it.
• Make a decision you’ve been putting off.
• Post or comment on social media.

And if you want to explore these ideas further, the reprint of The Courage to Ask is now available on Amazon.

Looking Ahead

In The Outstanding Professional in the Age of AI, this month is all about looking ahead. To succeed in any field, we must anticipate where the market is heading. After all, you can’t plan your own future without understanding the evolving needs of the people you serve. Fortunately, we can use AI itself to illuminate what’s coming.

For this module, we take a 3–5 year perspective—a timeframe in which AI’s trajectory is visible enough to guide practical decisions. The 10–20 year horizon is another matter entirely, which is why the Renaissance Mindset (January’s theme) remains indispensable.

We begin by envisioning a day in the life of a professional five years from now, surfacing both opportunities and blind spots. We then use AI to uncover emerging trends and client needs. Alongside this, we introduce “Explorer Conversations”—a deliberate practice of engaging key decision-makers to spark fresh thinking and build strategic, future-shaping relationships.

The webinar “Anticipating how AI changes your market” is on March 26th, 2026, at 12noon UK / 13h CET.  We cannot predict our own future without taking account of our client world. In this webinar we take a look at what’s on the horizon and examine:
– How AI will impact some current business functions e.g. HR / Marketing etc.
– What this means for your value-proposition
– Practices to guide your own career navigation: introducing Explorer Conversations
– Some classic pitfalls to avoid
– Bringing Explorer Conversations to life

You can register for the next webinar here.

“The Outstanding Professional in the Age of AI” is also available as a topic for conferences and events. Email John@SelfWorthAcademy.com with your event details.