Career and Jobs

How To Find The Courage To Quit A Successful Career

What can you do If you’ve worked successfully at one job for many years…..moved up and ultimately “fallen into” a career path…..How do you change that now after so many years of building a career path that you realize you don’t really want? – Professional with 25+ years of experience

I recently appeared on a LinkedIn Live Q&A about career fears, and the fear of pivoting after a longtime career was expressed by several attendees. While the sentiment was similar, there were different nuances for why making the change was so hard. Confirming the specific underlying reasons for your hesitation and addressing these issues is the best way to move forward.

Do you think you will fritter your time away not knowing what you want to do?

Many job seekers know what they don’t want more than what they do want. However, you do need to have some idea of the industries and roles you’re interested in so you know what to look for (and so prospective employers don’t feel like the rebound choice). If you’re afraid that indecision will paralyze you, give yourself a time limit to explore, and then make the best choice at that time. You can always change your mind again, but at least you will have started. Or, focus on consulting or project work, which is temporary by design. In the meantime, here are 10 exercises to help you figure out what you want to do.

Are you worried about making less money in a new career?

I coached a client who got a double-digit salary increase after a career change because she moved from a lower paying industry (publishing) to a higher paying one (life sciences). Another client who went from investment banking to education did take an overall cut in compensation because she no longer had the big banking bonus, but she didn’t take a cut in base salary, which is how she aligned her spending anyway. These are just two examples of people who made a big change without a big disruption on the financial side. If your fear is money-driven, actually run the numbers. Don’t assume that a career change will negatively impact your salary. If it does (like the banker turned educator), start making adjustments while you’re working on the career change (like living on the estimated new salary), so that when it happens, you are prepared.

Will you miss the accolades – e.g., peer recognition, senior title?

In my interview with longtime media recruiter Bucky Keady, she talks about hiring during an industry disruption (in this case, the print to digital transition) and how she screens career changers for their mindset – whether they are ready to move on or are stuck in the “good old days”. Be aware of your own mindset and whether you are ready to be a newbie in another industry or role. If you value the accolades, see if you can bolster your professional resume with achievements outside your current career, such as a leadership role within a community organization or an adjunct position at your local college. It’s okay to want to be the accomplished professional, and you can get to that stage again in your new career. Until you do, compensate with other ways to get recognition that are unrelated to your current career so you can start making that career change.

Do you feel guilty about having invested so much time doing something else

Sunk costs is a financial term for costs already spent that can’t be recovered. Sometimes businesses make poor choices because they want so much to see a return on their sunk costs that they persevere on a bad project or in a bad strategic direction rather than starting anew on something else that would have been more profitable. Though the term originated in business, sunk costs are evident in all sorts of decisions, including career decisions. The years you spent in a career you no longer want is a sunk cost. The money and time you spent on graduate school in an area that no longer interests you is a sunk cost. The effort you spent on a job search for something it turns out isn’t a better fit is also a sunk cost. You don’t have to keep doing something just because you started. Some of your efforts will definitely translate to your next endeavor, so you can use something from every past experience. In addition, whatever you did before has contributed to the person you are today, so in an overall way, these sunk costs are also an investment. That said, stop using sunk costs to direct future choices. Instead, start with your new end goal in mind and make decisions based on that.

Are you afraid of failing at whatever you do next?

Like the cobbler with no shoes, I, a career coach advising others on what to do, spent years in a career malaise before breaking out of it. I was suffering burnout in my business just a few years after having made the pivot from employee to entrepreneur. I tried all the usual suspects to scale (e.g., hiring people, moving from service to product) but I still wasn’t happy. It took these failures in scaling to help me right-size my business and finally feel comfortable in my new career choice. As I look back on my earlier career, I also had failures that I overcame, so why should I beat myself up more for failing in my big career pivot? The right answer is that I shouldn’t have, but I did anyway because this new career pivot feels like higher stakes. Maybe that describes your fear too: of being successful in one thing and then trying something else that doesn’t go perfectly and your negative self-talk screams, “I told you so!”. It will probably happen because trying something new never goes perfectly, but you’ll survive. My career pivot brought me a whole new life in Costa Rica.


The best time to plant a tree was 20 years ago. The second best time is now. — Chinese Proverb

Addressing the common fears above hopefully helps you find the courage to get started now. Think less about quitting your old career and more about starting your new one. Think of the fun in trying new things, meeting new people, achieving new firsts. Since there is no perfect time, why not now?

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