How to Deal With Career Regret — Even if You're a "Success Story" – Entrepreneur

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Dealing with career regret and turning it into life-enhancing transformations is possible. Here’s how.
If you’ve spent years (or maybe even decades) grinding away at the office to secure a certain role or salary, only to achieve everything you’ve ever wanted and regret it, you might be surprised to learn that you’re not alone. Sometimes we set ourselves goals before we have the experience to understand what we want out of our careers, and it’s only when we achieve them that we finally start to question if we truly wanted those things after all. Most professionals find themselves feeling some kind of regret, and no executive or senior manager is exempt from that.
The real question is: How can you deal with that career regret and maybe even turn it into a life-enhancing transformation? Let’s take a look:
Related: Are You Looking to Make a Career Switch?
They say that acceptance is the first step toward change, and that applies to your career just as well as anything else. When you’ve reached a high position in your work, and you’re enjoying the status and money that comes with it, it’s tempting to ignore that voice in the back of your head saying you wish you’d taken a different path.
The denial can work for a while, and maybe some people are prepared to go their whole lives this way. But it’s not going to get rid of those regrets completely, and it might even lead you to numb the pain in destructive ways.
Instead, face what you’re feeling head-on by taking note of your regrets. And take solace in knowing you’re not alone — one study found that as many as 78% of people wish they’d take more career risks. The simple act of articulating them in this way can sometimes give you the clarity you need, but if not, we have plenty more ideas for how to proceed.
Related: The Top 5 Regrets of Mid-Career Professionals
It’s easy to say that you should “reconsider your career path” or “figure out your true purpose,” but the reality is that it can be tough to pull off the kind of deep reflection you need while you’re still working 9-5 (never mind all the other commitments you may have).
If possible, take a break from your job to give yourself some space to think. Even a few days can be enough to allow you to switch off. Then, you can ask yourself which specific regrets you’re facing, why they might be plaguing you and how you could take action.
However, you don’t have to think about your job the whole time — get out in nature, try something new, move your body, or spend time with your loved ones. You might find that an epiphany suddenly washes over you and you gain clarity about what the “next move” should be in your career.
Related: 8 Entrepreneurs Reveal How They Discern Reflection From Regret
Ultimately, you’re the only person who can know what’s right for you, so it’s often best to get your thoughts together independently before you seek out advice from a third party. But sometimes we can overthink everything to the point that our thoughts get jumbled and we lose clarity about what we want. That’s where it can help to get a neutral third party involved.
If you don’t like the idea of burdening your loved ones with your confusion, or you want advice from someone who’s an expert in tackling the kinds of problems you have, consider going to a career coach. The International Coaching Federation (ICF) — which focuses on professional coaching — has gone from 8,000 members in 2005 to almost 50,000 in 2022. The services are popular for a reason. Coaches can be especially useful for higher-level professionals, as the average person lacks knowledge about the options available for executives and other business leaders.
A regret doesn’t have to remain a regret. Why not reframe it as a “calling” that made you finally change things for the better? No matter how old you are, there’s always time to make that change you’re dreaming of.
Many people assume that if they’ve spent a decade or more building up experience and skills in one field, they’ll be throwing it all away if they change directions. In reality, all that experience will be put to good use when you pursue a different line of work, even if there’s no obvious link between the two paths.
Successful entrepreneurs are often highly motivated, innovative business leaders, while ex-C-suite professionals stand a good chance of impressing investors and clients if they want to launch their own company. And these are just two examples of many — at the end of the day, if you’ve produced fantastic results and built fantastic skills, most organizations will consider you an asset.
But equally, your career regret won’t necessarily relate to you wanting to make a career transformation as dramatic as moving from corporate finance to teaching. Maybe you want to stay in a similar role but for a different industry, or you just need a change of scenery and want to move to a different company. It can feel like a daunting move, but why not take baby steps by looking for someone in your network who has the kind of role you’d like?
Don’t let your regrets define you. Career regrets are a mild, nagging feeling for some, while they can be completely debilitating for others. Whatever you do, don’t get sucked up by the sense that it’s already too late — that’s almost never true.
Give yourself some time for yourself, reflect, reach out for help, and don’t be afraid to make a big change. You might be surprised at what you can achieve.
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