Regret: your improvement catalyst

In my work with nonprofit organisations, and with mentees across a wide range of commercial and nonprofit settings, I see regret quite often as a drag on innovation, productivity, and improvement. One of the key steps involved in moving my clients forward, therefore, is to help them shift from feeling somewhat stuck in regret, to seeing the underlying cause of their problem as an opportunity or catalyst for a constructive response.

Daniel Pink’s bestselling book The Power of Regret: How looking backward moves us forward, is a helpful resource for those wanting to use their regrets as a strategic tool. Individuals may wish to do so for career advancement, professional development, or to enjoy a better life. Nonprofit organisations may wish to enhance their performance and/or conformance by harnessing regrets about targets not met, goals not achieved, or opportunities missed, to achieve more effective strategy execution.

If only …

Pink’s book notes that social scientists have often categorised regrets around school, work, sports/competition, and relationship settings. Having reviewed thousands of responses to his regret surveys, he discerned another pattern, which led to him identifying four core types of regret. These are illustrated in the header image above, and also in various other charts below. Pink’s descriptors and the associated ‘if only …’ statements are:

  • Foundation Regrets – “If only I had done the work” (e.g. studied, got a degree, applied myself, written the book, etc.)
  • Boldness regrets – “If only I had taken the risk” (and I would add ‘ If only I hadn’t taken the risk’)
  • Moral Regrets – “If only I/we had done the right thing”
  • Connection Regrets – “If only I had reached out”

While these core regrets are highlighted, two other ways of categorising regrets are offered:

  • regrets over the action taken versus those not taken, and
  • ‘open-door’ regrets (where the action is still possible) and ‘closed-door’ regrets (where the opportunity to act is no longer available)

Even with closed-door regrets, where say, the person you wanted to connect with has died, value may be found in reflecting on the gift of insight. In many cases, these regrets can lead to significant changes due to a commitment to never again make such an error.

Examples of regrets most of us experience as individuals, along with some commonly experienced by board directors, are offered in the chart below. Each in its own way is a catalyst for action, whether it be for personal improvement or for enhanced governance.

Catalysts for action

“If you would be good, first believe that you are bad”


As the title of Pink’s book suggests, his message is not to wallow in regret, nor to say you have ‘no regrets’, but rather to use regrets as a spur to the resolution of the problems or issues which were the key drivers, or root causes, of ‘error’ or ‘failure’. This approach is not dissimilar to the approach taken when an organisation is undertaking an incident analysis, or implementing a quality improvement process.

What’s ‘in the way’ IS ‘the way’

Risk Committees and senior managers know that failure to address the root causes of hazards will ensure that there will be future incidents or adverse events. Likewise, each of us can recognise that we will tend to keep encountering the same kinds of problems unless and until we identify the underlying drivers (or triggers) and address them fully.

Borrowing a Buddhist teaching about wake-up calls, the chart below expresses this idea about the root causes underlying personal regrets as the three poisons of craving, aversion, and ignorance. You don’t have to practice Buddhism to relate to these regret triggers and to recognise that they are a catalyst for action if you wish to improve your life or your organisational culture.

Your Failure Resume

Touch a hotplate and you learn not to do that again. Mistakes are often our best teachers.

A novel approach involving the cataloguing of regrets in a Failure Resume, invites us to reflect regularly on our failures and to capture what we have learned from them, as well as the action required to remedy the underlying causes. Pink argues that continuous small changes (reminiscent of BJ Fogg’s Tiny Habits) are his preferred approach, rather than expecting significant lifestyle changes to last beyond an initial short period of enthusiasm (much like the standard New Year’s resolution). This fits well with the continuous improvement mantra of the advocates for quality management.

The following chart suggests a format that could be used for a failure log or resume. Creating a record of what was learned from each so-called ‘failure’, will tend to reinforce the insights gained, and lock them in for future reference. Similarly, documenting how changes were made, or what action will be taken, ensure the greater likelihood that those changes effectively address root causes.

Regret: a reflective practice catalyst and strategic tool

“The unexamined life is not worth living”


In various earlier posts, I have advocated for the ‘So What Strategy‘ – in which a mentee, or a nonprofit organisation, uses the three prompts ‘What?’, ‘So What?’ and ‘Now What?‘ to look at the past, clarify its implications for future action, and then determine the action required to achieve the desired outcomes.

The steps recommended by Daniel Pink and Ed Daube Ph. D. echo the ‘So What?’ strategy by taking the reflecting party through a process of owning the regret, having self-compassion (rather than getting stuck in self-criticism), and committing to action that will improve the situation. The following charts are adapted from their work. They can be used by someone wanting to undertake a self-improvement process, a mentee working with a mentor or coach, or an organisation wishing to improve systems, processes, and/or risk management.

“The content of your character is your choice. Day by day, what you choose, what you think, and what you do is who you become.”


See also:
The Incident Analysis ‘Post-Mortem’: Fact, Causes, and Factors
20:20 Hindsight
What? So What? and Now What? – Your reflective practice guide

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