Job Hunting
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Regretting a Career Move: Reflecting, Reevaluating, and Taking the Next Step

May 22, 2023

Making a career move is often an exciting and promising step towards professional growth and fulfillment. However, there are instances when we find ourselves regretting the decision we made – sometimes months or a year later, but sometimes only weeks later.

Whether this regret is due to unmet expectations, a lack of satisfaction, or a misalignment with our true passions, feeling regret about a career move can be disheartening.

In this post, we'll explore how to navigate this challenging situation, reflect on the reasons behind the regret, and outline steps to take to move forward towards a more fulfilling career path.


Allow Yourself to Reflect andAcknowledge Your Feelings: Regretting a career move can be an emotionally challenging and draining experience – especially if you left a fulfilling job or job offers behind. It's important to give yourself permission to reflect on your feelings and understand the reasons behind your regret. Take some time to identify what aspects of your new career aren't aligning with your expectations or values. Is it the work environment, the tasks involved, or perhaps a mismatch between your skills and the job requirements? By gaining clarity on the specific sources of your dissatisfaction, you can better determine the necessary steps to address them.


Seek Guidance: Before you completely through in the towel, try to have an honest and candidate conversation with your hiring manager. Instead of placing blame, or making complaints about other people, try to have as constructive of a conversation as possible. For example:

1. If you feel like your managers or coworkers are dissatisfied with your work and that’s contributing to your career move regret, you can say something like: “Hey, it seems like there are certain projects or processes where others have had different expectations of my work and the outcome. Is this something we can talk through and find a solution that works for everyone?”

2. If you aren’t happy with the type of work you’ve been doing, try offering something like: “When I was originally brought onboard, I was under the impression that I would be working on X Project, but insteadI’ve been focused on Y Project for the last 6 months. Can you share with me a timeline for which I may be able to start working on X Project, and phase out the time I spend on Y Project?”

3. The company has made a massive pivot: “It looks like we won’t be investing much into Initiative A, for which I was hired for, and instead are moving in a different direction. Can you help me understand how I should be focusing my time? Will there be an opportunity to invest intoInitiative A in the future?”  


Asking a few simple questions and having a short conversation may alleviate your worries, and you may find yourself back on track to being committed to your role. But if this is not the case – keep reading.


Assess Transferable Skills and Explore New Opportunities: While regretting a career move can be disheartening, it also presents an opportunity for self-reflection and growth. Take the time to assess the skills you have developed in your current role and identify those that are transferable to other industries or positions. This is where writing down what you’ve been doing is important – document, document, document your accomplishments!Even if you’re not super proud of the role or what you’ve accomplished, it’s likely that you’ve learned some new skills, worked with a new team, or been part of conversations where you may not have previously been at the table.


Consider exploring industries or roles where your new skills can be leveraged, and where you may find greater satisfaction and fulfillment.


Upskill and Expand YourKnowledge Base: Sometimes, regret stems from a feeling of being ill-prepared or lacking the necessary skills for success in a new career. If you felt you were unprepared in a certain area but want to learn more about it, investing in further education, certifications, or skill development can be a proactive step to address those concerns. Identify the areas in which you feel deficient and seek opportunities to upskill through online courses, workshops, or professional development programs. By expanding your knowledge base and acquiring new skills, you can enhance your marketability and boost your confidence in pursuing a more fulfilling career path.


Pat Yourself on the Back forTaking a Calculated Risk: Exploring new career paths often involves taking risks, and it’s inevitable that you aren’t always right about every opportunity(plus, there are often factors outside your control - especially when it comes to startups!). Think of it this way: you’ve learned something you can apply to your future roles and are better prepared to evaluate the potential risks and rewards associated with each opportunity. Write down the questions you’d ask your next employer before accepting an offer based on this experience. Were there “red flags” you ignored in the beginning, that you knew wouldn’t work for you but you chose to disregard?


While it's essential to be cautious, don't let fear of making another wrong move hold you back from pursuing a more fulfilling career.Embrace calculated risks that align with your values, passions, and long-term goals.


Regretting a career move can be a challenging experience, but it also presents an opportunity for growth, self-reflection, and a renewed sense of purpose. By acknowledging your feelings, seeking guidance, assessing your skills, and exploring new opportunities, you can move forward with confidence towards a career that aligns with your true passions and aspirations. Remember, it's never too late to make a positive change and find fulfillment in your professional life.

Want more interview prep? Check out our posts on: 

Interview prep for Founding Engineers

How to answer the interview question, what do you bring to the company

How to talk about a career change

How to talk about your long-term career goals

For other interview tips, check out our other posts on interviewing on the blog.

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