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How to Manage Career Regret

Career Regret: That sinking feeling that your years of hard work have landed you in an unfulfilling career.

You've taken the Bar. You’ve passed your Boards. You’ve climbed the ladder. And the day-to-day of your work feels empty. Has the work changed or have you changed? Or both?

Many of us make decisions about our career choice before we have a partner, a family, or a permanent home. And it can be a decade of work and school before we end up in our destination. In the span of ten years, our priorities change, our values change, our strengths and talents change. The person who began the career journey is different from the one who arrives at the destination. And the day-to-day of a career is often different from what we imagined or hoped. So, it is no surprise when we experience career regret.

We are not stuck in this dynamic. There are steps we can take.

These questions can support your inquiry to determine if it’s time for a different career, a new employer, or support to uncover your own patterns and mindsets that are driving discontent.

Is it where you’re working?

There are a number of components to this inquiry. It’s helpful to get really clear about whether it’s your supervisor, the culture of your workplace, the values at your organization, your colleagues, or your particular job tasks. Be honest with yourself about what feels frustrating, unfulfilling, or difficult at work.

Is it what you’re doing?

Consider how often you are using your strengths and talents at work. We feel happier when we consistently use our strengths. If you aren’t, consider a conversation with your supervisor about your job tasks, or switch to a different position. Your employer will get the best from you in a strengths-based position.

Do you loathe the work of your career field? For example, if you’re an attorney who detests writing briefs and researching, consider different sub-specialties that you’d thrive in like transactional work or advising. Look at career options that use the skills you have in novel, fulfilling ways.

Are there mindsets or perspectives that are fueling your discontent? For example, if you are driven by perfectionism and it’s making you question your decisions, over-work, and have a tortured inner world, that’s not going to change if your job changes. Or perhaps you feel like you must serve everyone that comes through your door, and that’s not aligned with your values. You can change these dynamics without changing your career, but get some support to do so.

What do you long for?

Are you daydreaming about doing something different? Do you spend all of your free time doing something else that you wish were your job? Our dreams and longings contain important information for us. Allow yourself the time and space to explore this. What do you wish your day were like? What would you spend all of your time doing if you could? Which strengths and qualities of yours are you longing to use at work?

A healthy glug of self-compassion is called for here. We are all on a path, and it's okay if the road ahead isn't clear. Don’t hesitate to get support along the way!

All my best,


P.S. I am a multi-potentialite and have worked in education, law, policy, government, and non-profit organizations. I use these experiences in my coaching to support high-achieving, soulful women to transform their inner worlds, amplify their impact, and thrive through balance. There isn’t a job that I regret now, looking back on it. I absolutely had regrets at the time, but when I look back at my path, it all makes perfect sense.

Book a support call here.

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