Can you use regret to shape a better life? A countercultural provocation

I’m intrigued by books that take a counter-cultural stance.
 
I’ve recently been re-reading Daniel H. Pink’s best-selling book, The Power of Regret, in which he challenges the popular notion of ‘no regrets’.
 
Based on his World Regret Survey Pink categorizes regrets as:

• Foundation regrets – regrets where we opt for short-term gains over long-term payoffs, like not studying hard enough in school or not saving enough money. They often amount to: ‘If only I’d done the work’.
  
• Boldness regrets – regrets of inaction, such as not starting a business, asking someone on a date, or going on a trip. They often amount to: ‘If only I’d taken that risk’. Research suggests that people regret failures of inaction more than actions they took.
  
• Moral regrets often amount to: ‘If only I’d done the right thing’. Moral regrets are very context and culture-dependent.
  
• Connection regrets stem from when friends lose touch with each other over years, or families have a falling out. They often amount to: ‘If only I’d reached out’.

I often use the idea of boldness regret to inform some of my choices. As Pink puts it, ‘We are much more likely to regret the chances we didn’t take than the chances we did take’. So when I’m unsure or hesitant I often lean into opportunity, chance or just good ole action.

Pink finishes the book with advice on how to use regret as a force for good. Embracing regret, instead of avoiding it can help you grow and find more meaning in your life. One of my favourite tools included was self-compassion.
 
Pink’s mix of research, anecdotes and practical advice, make this book relatable and insightful.
 
If you’re interested in books that challenge conventional thinking, what are you currently reading?