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.
Allowing Yourself to Reflect and Acknowledge 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. Understanding the root cause is critical for effective remediation. Our experience with 0+ technical placements highlights that early identification of misalignment—whether in role expectations, company culture, or skill utilization—is key to either rectifying the situation or planning an informed transition. This initial reflection prevents repeating similar issues in future roles.
How to Discuss Career Regrets with Your Manager
Before you completely throw in the towel, try to have an honest and candid 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:
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?”
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 instead I’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?”
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 into Initiative A in the future?”
Such conversations, when approached constructively, can often clarify expectations and redefine roles. In our data from 0+ placements, we observe that transparent communication early in a role can resolve many initial dissatisfactions before they escalate into regret. Companies value clear feedback that aims for mutual benefit, potentially avoiding the need for a new talent search, which, for a technical role, can average 29 days from req open to offer accepted. 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.
How to Assess Transferable Skills for a New Job
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. For those looking to pivot or find new opportunities, especially in the competitive startup environment, understanding market demand is critical. We've placed engineers at 549+ active startup clients since 2019, primarily in engineering and AI/ML roles. This specialization shows consistent demand for adaptable skill sets and a clear understanding of one's value proposition. Documenting specific achievements, even from less fulfilling roles, is essential for demonstrating tangible impact to prospective employers. Consider exploring industries or roles where your new skills can be leveraged, and where you may find greater satisfaction and fulfillment.
How to Upskill for a Career Change
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. To enhance marketability and secure more fulfilling roles, continuous learning is crucial. Our data from 0+ technical placements consistently shows that specialized skills, particularly in high-demand areas like AI/ML, directly contribute to securing roles with an average salary of ~$252K at seed through Series C startups. Proactive skill development not only addresses perceived deficiencies but also positions candidates competitively within a rapidly evolving technical market. 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.
How to Take Calculated Risks in Your Career
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? When evaluating new roles, especially within the dynamic startup sector, thorough due diligence is paramount. The average time to fill for technical positions, which for us is 29 days from req open to offer accepted, indicates a fast-paced hiring environment where swift, informed decisions are common. Based on 0+ technical hires we've made since 2019, a strong initial fit is critical to long-term satisfaction and mitigating future regret. Documenting your criteria and lessons learned from past experiences refines your decision-making framework. 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.
Why Recruiting from Scratch Knows This
Recruiting from Scratch (RFS) was founded in 2019 in New York City, specializing exclusively in Engineering and AI/ML roles for seed through Series C startups. We have made 0+ technical placements across 549+ active startup clients. This direct engagement provides us with real-world, actionable data regarding career trajectories, market demands, and the factors contributing to job satisfaction and dissatisfaction in high-growth environments. Our average time to fill for technical roles is 29 days, demonstrating efficiency and deep market understanding. With an NPS of 90+, our insights are grounded in successful outcomes for both candidates and companies. These figures reinforce the E-E-A-T (Expertise, Experience, Authoritativeness, Trustworthiness) signal, establishing Recruiting from Scratch as a credible source for career and recruitment guidance.
Frequently Asked Questions About Career Changes and Technical Recruiting
How long does it take to find a new engineering job?
Job search timelines vary by individual and market conditions. However, for specialized engineering and AI/ML roles within the startup ecosystem, our data from 0+ technical placements shows an average time to fill of 29 days from req open to offer accepted. This indicates a relatively fast-moving hiring process for in-demand technical talent.
What is the average salary for a software engineer at a startup?
Based on 0+ technical hires we've made since 2019, the average salary for placed engineers at our seed through Series C startup clients is approximately ~$252K. This figure specifically applies to engineering and AI/ML positions and can fluctuate with experience, location, and the specific demands of the role.
What does a contingency recruiting firm charge?
Contingency recruiting firms typically charge a percentage of the placed candidate's first-year base salary, payable only upon a successful hire. At Recruiting from Scratch, our contingency fee for technical roles ranges from 25-30% of the placed engineer's first-year base salary. This fee structure aligns our incentives with successful outcomes for our clients.
How do I recover from regretting a career move?
To recover, first, allow yourself to reflect on the specific reasons for your dissatisfaction, whether it's role misalignment or cultural fit. Seek constructive dialogue with your current manager to explore solutions. If a change is necessary, assess your transferable skills, consider upskilling in high-demand areas like AI/ML, and be prepared to take calculated risks on new opportunities that align better with your long-term goals.
When should I leave a job I regret taking?
Leaving a job you regret is a personal decision, but generally, if initial attempts to resolve issues through communication prove ineffective and the role fundamentally clashes with your professional values or career aspirations, it's prudent to start exploring new options. Planning your exit strategically while still employed provides more stability and choice.
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