I spent years treating regrets like a cage - replaying decisions I couldn’t change, beating myself up over the past. Here’s the critical reframe: regrets aren’t about the past, they’re guides for what you should do next. The past is outside your circle of influence, but regrets are data about your values trying to redirect your future. I’ve found four main types (foundation, boldness, moral, and connection), and the goal isn’t avoiding regrets - it’s using them as a compass instead of a cage.
Most of this post comes from Daniel Pink’s power of regrets:
How to Think About Regrets
The past is completely outside your circle of influence. You can’t change what happened, no matter how much mental energy you pour into guilt or rumination. That’s critical to remember: regrets about past decisions are outside your circle of influence.
But here’s the reframe: while you can’t change the past, you can use those regrets to guide your future. They’re data points showing what you value most.
Concerns, Control and Influence
The first of the 7 habits, be proactive requires focusing your energy on your circle of influence, not your circle of concern. A frequent source of anxiety is trying to control things outside your influence.
The past? Guess what - that’s 100% outside your circle of influence. You literally cannot change it.
So here’s the shift: stop dwelling on backward-looking regrets (what you did wrong) and start using forward-looking regret avoidance (what you should do next).
Where do you have influence? The future (and more accurately, the present). Think through potential future regrets before making decisions. I frequently remind myself that no one ever uttered “God, I wish I spent more time at work” on their deathbed.
Use regrets to:
- Learn and grow: Let past regrets motivate you to be more responsible, take healthy risks, make amends, and prioritize what truly matters
- Avoid future regrets: Anticipate what you might regret and weigh that against potential benefits
Be compassionate to yourself - forgive
Compassion is about removing suffering and accepting people as they are. It’s easy to extend compassion to others - but it’s even more important (and harder) to apply it to yourself.
When you have regrets, treat yourself with the same compassion you’d offer a friend struggling with similar feelings.
Compassion can be broken down with a time dimension.
| Time | Behavior | Practice | Behavior Definition |
|---|---|---|---|
| Past | Forgiveness | Humility | Give up hope for a better past |
| Present | Acceptance | Gratefulness | Recognizing you have received more than your fair share |
| Future | Hope | Patience | Believe the future can be better than the present |
Judgment vs Curiosity
Judgment throws up barriers and causes us to hide the truth which can lead to guilt and shame. Curiosity is gentle and helps us find what is going on. Compassion reduces judgment, reducing the barrier to compassion.
When processing regrets, lead with curiosity rather than judgment. Instead of beating yourself up over past decisions, get curious about what drove those choices and what you can learn from them.
The Four Regrets
When thinking about regrets, they tend to fall into patterns. Daniel Pink’s The Power of Regret analyzed over 16,000 regrets from 105 countries and found four core categories. Understanding these patterns helps you anticipate what you might regret before you make decisions.
The four regrets operate as a photographic negative of the good life - if you know what people regret most, you can reverse the image to see what they value most.
Foundational - If only I’d done the work
Foundation regrets stem from failures to be responsible and do the hard work that builds a stable life. These are the “I should have known better” regrets about not laying proper groundwork. They often compound over time - small neglects become major problems.
E.g.
- Financial stability: Not saving for retirement. You live paycheck to paycheck in your 60s because you spent everything in your 20s.
- Health and wellness: Not prioritizing exercise, sleep, and nutrition. You deal with preventable chronic conditions because you ignored your body for decades.
- Education and skills: Neglecting self-improvement. You watch less experienced people get promoted because you never developed new skills.
- Relationships foundation: Not learning to communicate or manage emotions. You repeat the same relationship patterns because you never did the inner work.
Boldness - If only I’d taken the risk/opportunity
Boldness regrets come from playing it too safe - from inaction rather than action. These are the chances not taken, the words not spoken, the dreams not pursued. The pain comes from wondering “what if?” and knowing you’ll never find out because fear or comfort held you back.
E.g.
- Romantic risks: Not asking someone out when you felt a connection. You wonder for years if they felt the same way.
- Career leaps: Not starting the business you dreamed of. You stay in the safe corporate job while others build the company you imagined.
- Life experiences: Not traveling when you had the chance. You say “someday” until health or circumstances make it impossible.
- Creative expression: Not sharing your art, writing, or music. You keep your gifts hidden because you fear criticism.
- Speaking up: Not saying what needed to be said. You stay silent when you should have advocated for yourself or others.
Moral - If only I’d done the right thing
Moral regrets arise from compromising your values or hurting others. These cut the deepest because they damage your self-image and often harm people you care about. They’re about knowing you chose wrong when you knew what was right.
E.g.
- Betraying trust: Cheating on a partner or in competition. You carry the guilt of violating someone’s faith in you.
- Dishonesty: Lying for personal gain. You carry the weight of a lie that affected someone’s life.
- Selfishness: Taking credit for someone else’s work. You prioritized your comfort over another’s need.
- Cruelty: Being hurtful when you could have been kind. You bullied someone or said something deliberately cutting.
- Ethical lapses: Going along with something wrong. You stayed silent about unethical behavior to protect yourself.
Connection - If only I’d reached out
Connection regrets stem from neglecting relationships or letting them wither. These hurt because relationships are central to human flourishing, and we often don’t realize their value until it’s too late. The regret is knowing a simple act of reaching out could have preserved or healed something precious.
E.g.
- Drifting apart: Not staying in touch with friends and family who mattered. You realize years later that a valued friendship died from neglect, not conflict.
- Unresolved conflicts: Not making amends after an argument. You carry the burden of a broken relationship that could have been repaired.
- Missing moments: Taking loved ones for granted. You wish you’d spent more time with a parent who’s now gone, or listened when your child wanted to talk.
- Words unsaid: Not expressing love or appreciation. You never told someone how much they meant before they died or moved away.
- Pride and stubbornness: Letting ego prevent reconnection. You wait for them to reach out first until it becomes impossible.
How regrets change over time
As we can see, regret distribution varies across age groups. People tend to have the most boldness regrets in their 20s, which may be due to feeling like they haven’t taken enough chances or pursued their dreams. Regret about foundation choices tends to increase with age, possibly due to a greater awareness of long-term consequences. Connection regrets also tend to rise with age, perhaps as people reflect on lost relationships or missed opportunities for connection.
It’s important to note that this is just a general trend, and individual experiences may vary.
Closing Thoughts
Regrets will happen. That’s not the problem. The problem is letting them cage you instead of guide you.
The next time you feel that ache of regret, ask yourself: What is this telling me about what I value? What can I do differently going forward? How would I advise a friend in this situation?
Your regrets are trying to help you. Let them be your compass pointing toward what matters most - not a cage keeping you stuck in the past.
Start small: Pick one regret you’re carrying. Get curious about it. What does it reveal about your values? What one thing could you do differently tomorrow?