201. But Will You Still Have Regrets?
- cindyesliger
- Jan 15
- 9 min read
Updated: Jan 21
Regret is not a weakness but a signal that something matters deeply to us. When we acknowledge and explore regret instead of avoiding it, we gain clarity about our values, patterns, and desires, allowing us to make wiser and more intentional career decisions. By learning to work with regret rather than against it, we build self-trust, confidence, and forward momentum.
It can be a process of revisiting, reflecting, and—if we’re brave enough—revising.
Are you carrying lingering ‘what if’ thoughts about past career decisions you never fully examined? Are you feeling stuck, restless, or dissatisfied at work but can’t quite explain why? Are you afraid that making the wrong move now will only lead to more regret later?
You’ll learn that regret isn’t a sign you failed or made a bad decision—it’s valuable emotional feedback pointing to what matters most to you. When used intentionally, regret can become a powerful tool for clarity, confidence, and wiser career decisions.
WHAT YOU WILL DISCOVER
Why reframing regret as information instead of a flaw is essential
3 practical ways to turn regret into strategic fuel for career growth
Why unacknowledged regret quietly sabotages careers
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TRANSCRIPT
Welcome to the Stop Sabotaging Your Success podcast, episode two hundred and one. I'm your host, Cindy Esliger. This is the podcast focusing on what we can do today to take control of our careers and overcome the inevitable barriers to success that we encounter along the way.
Frankly, I don't trust anyone who says they live with no regrets. It sounds bold and brave to say, "I did it my way", but when you dig a little deeper, they're often full of crap. Because, in my opinion, everyone has regrets. If you've ever made a decision, you've probably had at least one moment where you wonder whether you should have done it differently. Regret isn't a sign that something's wrong with you. It's a sign that something matters to you. It's feedback. It's information. And when we learn to use it well, it can become one of the most powerful tools in our career toolkit—especially in male-dominated professions where the rules seem to be intentionally unclear and the expectations are sky-high.
In this episode, we're going to talk about regret—that unpleasant little emotion you'd rather shove in a drawer and forget about. It can actually help you grow, gain clarity, and make wiser professional decisions. It points to something that matters to you, something that didn't align, or something that maybe still needs your attention. Regret, when acknowledged and explored, can be a catalyst for clarity and transformation. Feelings of regret can help us slow down, reflect, and move forward in a more intentional, empowered way.
Regret is easy to recognize but hard to define. It's that gnawing sensation—part disappointment, part self-criticism, and part hindsight—that arises when something we did (or didn't do) led to an outcome we wish had gone differently.
It usually involves a comparison not just between what happened and what we wanted to happen, but it can also bring in what we imagine could have happened, if only we'd chosen differently. And that's where regret can get tricky—because while it can be deeply uncomfortable, it can also be deeply instructive.
Think of regret not as a static emotion, but as a process. It can be a process of revisiting, reflecting, and if we're brave enough, revising. Regret doesn't have to paralyze you. It can prepare you. It doesn't have to bring you down. It can lift you up, if you know how to use it to your advantage.
We've all been told there's a benefit to learning from your mistakes. Well, regret is often the emotional nudge that tells us there's a mistake to learn from in the first place.
When we treat regret as a tool, rather than a way to torment ourselves after the fact, we gain:
Self-awareness about what we truly value.
Clarity on what kind of risks are worth taking.
Motivation to do better next time.
Strategic foresight for future decision-making.
Empathy and compassion, not just for others, but also for ourselves.
In this way, we can use our feelings of regret to further our own self-awareness.
Now, switching gears, let's talk about what happens when we don't deal with our regrets. Because avoiding regret doesn't mean it disappears. It can fester and show up in more subtle, insidious ways.
Here are four of the most common consequences of not reckoning with your regret:
Career Stagnation: You play it safe by sticking with what's familiar. You stop challenging yourself and years go by without measurable growth.
Chronic Dissatisfaction: Everything may look fine on paper, but you're feeling miserable, resentful, or completely checked out. You keep pushing yourself to find a way to succeed in a role you're not even sure you want anymore because it's just more of the same.
Low Self-Trust: You begin to doubt your decisions because you've never taken the time to reflect on how your past decisions have shaped you and led you to where you are.
People-Pleasing Paralysis: You let others' opinions override your own instincts, which unfortunately, often leads to more regrets.
That's the professional cost of unacknowledged regret. And, for many of us, we're not even aware it's happening.
So, how do you know if you're someone who's stuffing their regret under the rug?
You brush off past decisions with 'it is what it is' energy, even when it's still obviously bothering you.
You rationalize every choice as 'the best I could do at the time', but never look deeper.
You obsess over past events but never change your behavior.
You fear being seen as indecisive or weak if you admit that you would have done things differently, knowing what you know now.
You ignore the little voice inside that's saying this doesn't feel right—because it's inconvenient or maybe you're not sure what to do about it.
Sound familiar? You're not alone. Regret is uncomfortable. It asks us to feel things we'd rather avoid. But avoiding those feelings doesn't mean they stop having an impact.
So, what can we do with our regrets? Here are three ways you can turn your regrets into strategic fuel for career growth:
Reflect on Your Past Regrets: Not to beat yourself up, but to learn from them. Ask yourself: Which of my values were not in alignment at that moment? What thoughts or feelings did I ignore, dismiss, or silence in myself? What would I do differently, knowing what I know now? This kind of reflection helps you set a stronger foundation for future decisions. If you don't consciously acknowledge the regret, you risk repeating the same choices next time—and trust me, the regret feels worse the second time around.
Anticipate Your Potential Future Regrets: Before making a decision, project yourself into the future, maybe one year, five years, or even ten years out. Ask yourself: Which option will I wish I had chosen? What will my future self be proud of? Which decision aligns with the life I want to build—not just the comfort I want to preserve? This technique helps you optimize regret, not minimize it. And that's key, because trying too hard to avoid all regret can backfire. You'll end up stuck, playing small, or paralyzed by indecision.
Recognize the Lessons in Your Regrets: Our regret can teach us about: our values, what really matters to us; our patterns, what we keep doing that may no longer be serving us; and our desires, what we actually want, not just what others told us to go after.
According to author, Dan Pink, there are four core categories of regret:
Foundation Regrets: If only I had prepared better. These relate to setting yourself up for success, like saving money, developing skills, or establishing boundaries.
Boldness Regrets: If only I had taken the chance. These are the things we now wish we'd done when we had the opportunity, things we should have tried to make happen for ourselves.
Moral Regrets: If only I had done the right thing. These could be staying silent when you should have spoken up, or going along with something you didn't believe in.
Connection Regrets: If only I had reached out. These are often about relationships, where we wish we'd stayed in touch with people or thanked them for what they did for us.
The beauty here is that every regret points to a value. So, the more we understand the categories we tend to fall into, the clearer we get about what matters most to us.
Having some regret is inevitable. And that's okay. Sometimes, when we have a decision to make, each of the choices can lead to regret. You take one of your job offers, and you regret the missed opportunity. Welcome to being human.
Regret is not always a sign you did something wrong. Sometimes, it's just a sign that something was hard, or that you were at a crossroads, and that you were brave enough to choose and make the most of the choice you made.
What matters is what you do with the regret afterward.
Let's say you're thinking of making a major career move—quitting your job, changing industries, or going after a leadership role at a new company. You're going to hear a lot of opinions. You may even get talked out of it by people who just want to protect you from disappointment or risk. Thank them for their concern, but remember, it's your choice to make.
Because, if you let someone else's fear shape your choices, you may end up regretting not doing something that you have the opportunity to explore.
So, before you make the decision, ask yourself: Am I making this choice from a place of fear or possibility? What will I regret more—doing it and failing, or not doing it and never knowing? What do I want to become, and does this decision move me in that direction?
Listen to the stories of others—your peers as well as your mentors. What did they regret not doing? What choices do they wish they had made? Some people prefer to frame it as 'lessons learned' or 'insights gained', and that's fine. They may not like the word 'regret' because, to them, it may feel very loaded. Use whatever label helps you access their perspective and insight.
Sometimes, someone's offhand comment about a road not taken will stick with you for years and shape your next big move. But, don't wait until it's too late to realize what you actually wanted.
Here are five powerful ways to harness the value of regret without getting stuck in it:
Use the 'Future Self' Test: Ask yourself: Will this matter to me five years from now? This can help you put things into perspective quickly.
Sort the Decisions That Actually Matter: We all make hundreds of decisions a day—most don't warrant even considering regret. Save your emotional energy for the ones that will have an impact on the direction of your life.
Reframe 'Mistakes' as Data Points: Don't think of it as failing. Instead, focus on what you've learned from the experience. Use that data to make better decisions moving forward.
Set Your Own Bar: Don't let someone else's idea of success dictate what you think you might regret. You're allowed to want different things. You're also allowed to change your mind and course-correct along the way.
Practice Self-Compassion: Regret can be painful, so don't pile shame on top of it. Be kind to yourself. Regret shows you care—and that's something to be proud of.
What you may not realize is that regret doesn't always show up as regret. It can show up as frustration, restlessness, or even perfectionism. You might think you're just tired of your job or annoyed with your team, when really, you're carrying the weight of unacknowledged decisions that you didn't make—opportunities you passed on, risks you talked yourself out of, and values you compromised on.
That feeling that 'something's off' can actually be regret trying to get your attention, quietly urging you to examine what you really want and how to realign your actions with going after it. When you don't recognize it for what it is, we can't use it as the powerful guide it's meant to be.
When we stop treating regret as something shameful or weak, we can begin to recognize it as an emotional cue that reveals what truly matters to us. By examining past regrets, we uncover patterns in our choices and gain clarity about how we want to show up in the workplace and in our lives.
Regret isn't something to fear or bury; it's a powerful emotional guide that can reveal what truly matters to us and where we want to grow. By reflecting on past choices with curiosity and anticipating future regrets with clarity, we can make wiser, more aligned decisions for our careers.
When we learn to work with our regrets instead of against them, we create momentum, confidence, and the kind of intentional progress that leads to a more fulfilling professional life.
And that's it for this episode of Stop Sabotaging Your Success. Remember to download your Guide to Turning Regret into Career Clarity at cindyesliger.com/podcast, episode two hundred and one.
Thank you to our producer, Alex Hochhausen and everyone at Astronomic Audio. Get in touch, I'm on Instagram @cindyesliger. My email address is info@cindyesliger.com.
If you enjoy listening to this podcast, you have to come check out The Confidence Collective. It's my monthly coaching program where we dig a little deeper into what's holding you back in your career and we find the workarounds. We help you overcome the barriers and create the career you want. Join me over at cindyesliger.com/join. I'd love to have you join me in The Confidence Collective.
Until next week, I'm Cindy Esliger. Thanks for listening.
