The Chicken and The Egg: How to break the cycle of job hopping and unfulfillment

4 min readJan 19, 2022


If you’re asking yourself “how do I break the cycle?” (of job hopping), or if you’re feeling like, “it never ends,” or “the workweek feels like 50 years long,” then I’m here to help. Without taking a pause and a step back to consider your options for which roles and industries are the best fit for you, you’re succumbing and agreeing to continue wasting time in a path that is less than ideal, less than your potential, or maybe even toxic.

My clients are often working professionals who pursue career exploration on top of their everyday jobs. This means that they’re making time after a long day of work or on short weekends to pursue their own professional development. This is never easy to do, and it requires a lot of drive, commitment, and accountability, but it’s really the only answer to break the cycle of job disengagement or job hopping.

Remember that career exploration and job search can and should be done in a finite time frame, so it shouldn’t be something that feels like it will take forever, and if it is, seek out guidance so you can be more strategic and effective. That being said, you can remind yourself that for a very short period of time, you have this added agenda to your plate, but that it’s the only way to break out of, and into, a more suitable, fulfilling career path.

Also, remember that professional development can and should happen within your job but also outside of it, so you can figure out where you belong in this professional world. I usually suggest an 80/20 or 70/30 split so that you can largely focus on doing well in your role, but also spend time each week devoting time to your own professional development and clarifying your broader path.

In order to break the cycle, here’s what you need to do:

  1. Assess and face your readiness
  • Commitment is the first step. Ask yourself how long you’ve been feeling this way and how much longer you’re willing to wait/endure your current situation. Ask yourself what will help ensure that you can get yourself to a place of open-mindedness and readiness to explore. Realize and recognize that you deserve and CAN find a role you will thrive in.

2. Decide where you need career support specifically

  • This depends on what your goal is — is it clarifying your best fit career direction? Is it deciding on upskilling programs/further education? Is it improving your personal branding? Is it job searching? (Hint: all of these are relevant to leveling up your career, but typically I’d advise going about it in the order these questions are listed).

3. Decide on your ideal timeline

  • When would you like to achieve each goal by? What will that mean in terms of how much time you want to devote each week? What support do you need to achieve that goal efficiently and effectively?

4. Decide what format of support will help you navigate your next steps

  • Coaching can be extremely helpful so that you have guidance on best practices, a form of accountability, and a space for holistic self-reflection.
  • Other areas of support include: peer-peer accountability, mentorship, online informational resources (blogs, YouTube, etc), project management-oriented tools to stay organized, etc.
  • Decide what elements you would want or need from your support system.
  • Gather some options for support and then you can compare to determine which format of support suits you best.

5. Go forward and prosper!

In order to learn about WOKEN’s career exploration and job search platform and coaching, check out their website here or book a free career coaching call here.

Rachel Serwetz’ early professional experience was at Goldman Sachs in Operations and at Bridgewater Associates in HR. From there, she was trained as a coach at NYU and became a certified coach through the International Coach Federation. After this, she worked in HR Research at Aon Hewitt and attained her Technology MBA at NYU Stern. Throughout her career, she has helped hundreds of professionals with career exploration and for the past 4+ years she has been building her company, WOKEN, which is an online career exploration platform to coach professionals through the process of clarifying their ideal job and career path. She is also an Adjunct Professor of Entrepreneurship at Binghamton University and has serviced as a Career Coach through the Flatiron School, WeWork, and Project Activate.




Waking you up to remember that you can and should find a job you love.