Still searching for purpose? Regret already knows
The most useful focusing tool you didn't know you had
Purpose. Vision. Values.
They’re supposed to guide you, anchor you, help you decide what really matters.
But what if they don’t?
What if you’ve done the journaling, the workshops, the life-design canvas, and still feel foggy? What if your so-called 'clarity' hasn’t translated into action, or peace, or momentum?
I think that's where regret can be a powerful tool for you.
Purpose, vision, values all have in common that they describe you at your best. The ideal and aspirational you.
Regret is not like that; it's candid.
Not who you want to be, but who you meant to be, but didn't become.
Not what you planned to do, but what you failed to do and still carry with you.
That's why it stings.
And that's why it might just be the most useful focusing tool you didn't know you had.
Regret is a mirror & jolt for more clarity
To truly focus on what matters, you need more than just goals or good intentions.
You need clarity. And clarity rests on a few essential ingredients:
A long-term sense of direction
A compass for your choices
A mirror to see yourself as you are
And every now and then, a jolt of truth you didn’t ask for
Purpose, vision, and values can help you with the first two. They’re about aspiration. They chart a path.
But for the mirror and the jolt? Regret can take care of that.
Regret links directly to your deepest values
Daniel Pink’s research identifies four core types of regret:
Foundational: "If only I'd done the work."
Boldness: "If only I'd taken the risk."
Moral: "If only I'd done the right thing."
Connection: "If only I'd reached out."
Each one points to a core human need:
Stability
Growth
Goodness
Love
The lived experiences of people who share their regrets (often, but not only, at the end of their lives) is deeply moving, and I can only encourage you to read them in Pink’s The Power of Regret.
Regret, unlike purpose statements or values, is specific: it points to an action not taken, mostly to a missed opportunity. ‘What I could have done’ is a bigger source of regret than ‘what I should have done’. We typically take care of the ‘should haves’; it’s the missed ‘could have’ that bugs us more.
Regret is also emotionally honest. We tend to rationalize our choices. We write neat stories about why things didn’t work out. Regret cuts through that, it doesn't lie.
Regret forces you to ask better questions
“Be patient toward all that is unsolved in your heart and try to love the questions themselves” - Reiner Maria Rilke
Rilke’s words have stayed with me. And over time, I’ve come to believe this:
It’s not so much about having better answers, but about having better questions, especially the ones you’re afraid to ask yourself.
That’s why regret is so powerful, because at its heart, it’s about this question:
What if I had only …?
That’s not an easy question. But it can be clarifying.
If you let it, regret can show you the delta between who you are and who you are meant to be.
Rather than dwelling in the past, you’re taking a time machine into the future to learn for the present.
So, how do you do that?
Three ways to use regret to refocus
Here’s how to make regret work for you:
1. Use the right questions in your weekly review
Take one or two questions from below. Pick the ones that resonate most (for me, it’s the first and the last question). Don’t try to answer them all. Go deep, not wide.
Foundational regrets (stability):
Where am I choosing comfort now and risking regret later?
What daily effort am I underestimating because it doesn’t pay off fast?
What’s one area where steady effort today could prevent regret tomorrow?
Boldness regrets (growth):
If I weren’t afraid, what would I try?
What dream feels too risky to chase but too important to ignore?
Five years from now, what bold move do I want to thank myself for?
Moral regrets (goodness):
What’s one wrong I can start setting right today?
What am I not saying or doing that needs to be?
When I look back, what kind of moral legacy do I want to have lived?
Connection regrets (love):
Who do I still care about but haven’t told recently?
Which relationship needs me to take the first step - again?
If this person truly matters, how will I prove it with action?
2. Talk to someone or journal
Speaking your regrets out loud, or writing them down, can be cathartic. Self-disclosure is intrinsically rewarding - a finding backed by neuroscience, which shows that sharing personal information activates the brain’s reward system.
But there’s a catch: we also know that talking about goals or intentions can sometimes feel like taking action, without the follow-through.
So: reflect, express, but pair it with a clear next step.
3. Minimize the big regrets
Trying to minimize all regret can be paralyzing. It leads to overthinking, perfectionism, and the pressure to get every decision right before you even make it.
But ignoring regret altogether has its own cost: it robs you of insight. You lose the chance to see what mattered, what moved you, what could have been different.
The middle path? Aim to notice and minimize the big regrets: the foundational regrets, the regrets about not being bold enough, the regret of not having made the right, moral choices and the regret of not nurturing your connection to other people.
As Daniel Pink puts it, you don’t need a regret-free life. You need a life shaped by the wisdom that regret can bring. Let it show you what matters.
Your future self is watching.
And rooting for you to listen.