Overcoming Career Regret
Regret is a natural part of many professional journeys. At some point, most people look back and question a career decision, wondering what might have happened if they’d taken a different path. While regret can be uncomfortable, psychological research shows that it doesn’t have to be a bad thing. When reframed, regret can offer useful insight and create space for clarity, confidence, and growth.
This article explores what makes regret so persistent, how our thinking habits can reinforce it, and practical ways to move forward from a place of self-respect and learning.
Why does Career Regret Feel So Heavy?
Career decisions are often tied to our identity, values, and sense of purpose. When something doesn’t turn out the way we hoped, such as a job that didn’t fit, a missed opportunity, or a difficult exit, the emotional weight can feel overbearing.
From a psychological standpoint, this reaction is shaped by more than just the outcome. It’s influenced by how we interpret the experience, what we believe it says about us, and how we compare ourselves to others.
One common pattern is (re)imagining alternative scenarios that seem better than our current reality (counterfactual thinking). While this can sometimes help us learn from the past, it also risks keeping us focused on “what might have been” rather than what’s possible now.
Mental Habits That Reinforce Regret
Psychological research shows that certain thinking habits can amplify feelings of regret:
Availability bias: We pay more attention to recent or vivid experiences. A recent setback may feel more defining than years of progress.
Confirmation bias: Once we feel regret, we tend to focus on evidence that supports that emotion and ignore signs that things also went well.
Hindsight bias: We believe we “should have known better” after seeing how events unfolded, forgetting that we didn’t have the full picture at the time.
Overgeneralization: We interpret one regretful experience as representative of all future outcomes.
Counterfactual thinking: We focus on imagined alternatives instead of staying grounded in the context and information we had at the time.
Labeling: We assign fixed negative identities to ourselves based on a single action/decision.
Mental filtering: We focus exclusively on what went wrong, ignoring anything that worked or went well.
All-or-nothing thinking: We view our career choices in black-and-white terms; either a complete success or a total failure.
When unexamined, these mental habits and regrets can keep us stuck in rumination rather than reflection.
Begin noticing how your mind interprets regret. Is it drawing from recent emotion, reinforcing a fixed expectation, or comparing to an imagined alternative?
👉Begin noticing how your mind interprets regret. Is it drawing from recent emotion, reinforcing a fixed expectation, or comparing to an imagined alternative? When you catch yourself dwelling on the past, pause and ask:
“Am I remembering this through a narrow lens?”
See if your mind is replaying just one part of the story. Then, shift focus: What did I learn? What’s still possible now?
Make space for a wider perspective, choice, and movement forward.
When Expectations Clash with Reality
Some people experience deeper regret because of how they relate to uncertainty, control, or their professional identity.
If you have a strong need for predictability, the ups and downs of a career can feel especially unsettling.
If you tend toward perfectionism, even small deviations from your ideal path might feel like failure.
If your self-worth is strongly tied to your professional identity, career missteps may feel like personal flaws.
If you frequently compare your journey to others, you may overlook the value in your own timing and progress.
Research shows that difficulty tolerating uncertainty and holding rigid internal standards can make it harder to move on from past decisions. People with high expectations of themselves may interpret career missteps not as normal experiences, but as evidence of personal failure (Sirois & Stout, 2010). Others who struggle with ambiguity may feel stuck in indecision or regret simply because the outcome wasn’t clear or controllable (Carleton, 2016).
Professional growth is rarely clean or linear. Building acceptance of trial, error and redirection, is a part of developing a resilient mindset.
Notice where your expectations about how things "should" go are impacting your ability to adapt.
👉Notice where your expectations about how things "should" go are impacting your ability to adapt. Ask yourself:
"Am I allowing room for learning, variations, and redefinition of what I want?”
A flexible mindset means making space for growth in reality (not lowering your standards).
Moving Forward: Strategies for Working with Regret
The following strategies draw from psychological research to help professionals process and move through regret constructively…
1) Normalize and Validate the Feeling
It’s okay to feel regret, it doesn’t mean you failed. Feeling it means you care about the choices you make. Acknowledging the emotion, rather than avoiding or over-identifying with it, is the first step toward working through it constructively. Validating the emotion without judgment creates room for lightness and clarity.
Research highlights that emotional acceptance (the ability to notice and allow difficult feelings without judgment) supports long-term resilience. In a large meta-analysis, Ford et al. (2018) found that people who routinely accept their negative emotions experience better psychological health over time.
Validating your experience, even if it’s painful at first, makes it possible to shift from rumination to action.
2) Reframing regret as A contribution.
Change the narrative with different questions. Instead of asking questions that can lead to self-criticism, such as “Why did I do xx?” “Why didn’t I do xx?”, try asking:
What did I learn about what matters to me?
How has this changed how I behave now?
What assumptions was I holding then that I no longer believe?
What would I say to someone else facing a similar situation?
Can I recognize that others also struggle with similar decisions and emotions?
The answers to these sorts of questions provide clarity about your values, boundaries, and/or needs and become a guide for future choices, turning regrets into a way to build a more fulfilling future.
3) Connect with Others
Sharing your story in a safe space can reduce isolation and offer new insight. Hearing others’ honest experiences often reminds us that most careers are full of turns, pauses, and course corrections.
A coaching session focused on regret (e.g. a specific missed opportunity or a difficult decision) can help turn that experience into meaningful insight.
Coaching provides a non-judgmental space to slow down, explore what the regret is pointing to, and distinguish helpful reflection from unproductive rumination. With support, you can identify patterns, reframe limiting narratives, and discover new choices that align with your current values and priorities.
4) Practice Self-Forgiveness
Research (e.g. Lyubomirsky, Tkach, and Dimatteo, 2006) shows that self-forgiveness improves emotional well-being and reduces long-term regret. Instead of holding yourself in a cycle of blame, try recognizing your past actions as part of your growth process.
Ask yourself:
What would it feel like to forgive yourself for doing the best you could with what you knew then?
What part of you were you trying to protect or support at the time?
Conclusion
Regret is part of the human experience, especially when it comes to something as personal as a career. But it doesn’t have to define your story. With awareness, compassion, and reflection, it’s possible to shift from feeling stuck in the past to using those experiences to build a more fulfilling future.
By understanding the thought patterns that sustain regret and intentionally replacing them with supportive habits, you can carry the lessons forward without carrying the weight. Every path has its complexity, and every choice can offer something valuable, even if it didn’t lead where you expected.
Looking for more Support?
If this topic resonates with you and you're navigating your own experience of career regret and wondering what to do next, I am happy to think along with you.
Reach out via email or schedule a call.
In the meantime, take a look at other self-coaching articles for more tools, reflections, and next steps.
