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Jumping Jobs: 21 Questions for a Strategic Career Move

Jumping Jobs: 21 Questions for a Strategic Career Move

by Dwight Bain, MA on November 7th, 2022

Why are people quitting their jobs in record numbers? Did they find a better opportunity or is it because they are sick of working in a dead-end job, perhaps with a “bully” boss? In what some are calling the “Great Reshuffle,” millions of U.S. workers are voluntarily quitting their jobs and walking away from their current place of employment.

Yet, the Department of Labor data shows that for every unemployed worker, there are 1.2 job openings ( Some industries are offering much higher wages, but still cannot find or retain workers. If you are ready to jump jobs, you are not alone. Research from Yahoo Finance, Harris Polls, and reveals the following:

  • 37% of workers are leaving their current jobs or already preparing to make the move
  • 95% of workers say they are thinking of quitting their jobs
  • 65% of workers feel greater job opportunities are available to them
  • 92% say they would consider switching industries for something less stressful
  • Burnout is the single greatest reason given to quit their jobs

“Changing jobs will not solve all your problems, but it may give you different problems.”


Before you quit your job, think about this comparison. Most travelers can relate to being on an uncomfortable, crowded, and bumpy flight, but few would jump out midair “D.B. Cooper” style. They endure the miserable conditions to safely arrive, while considering flying on a different airline in the future. They would never jump out without a parachute or a without a plan.

Sadly, it seems some are impulsively quitting with the hope things will automatically work out on the way down . . . gravity and reality teach otherwise. A better approach before you try jumping to a better job is to see if you are ready to make the jump in the first place. Consider the philosophy of Stanford professor, Dr. Dave Evans, who said, “Every worker is working for themselves – whether they know it or not . . . with full awareness the degree of autonomy different people have in different roles varies tremendously. The line worker in a factory, the Door-Dash delivery person, and the Google senior product manager have very, very different situations. But they also all share something . . . not one of them is powerless.” (For more of Dave’s tips on how to quit spectacularly well, visit:


Everyone feels pressure, but wisdom teaches us to have a plan before we jump to escape the pressure. Make sure you are ready to move on to a better opportunity by asking these coaching questions for greater opportunities after you jump.

  • Why are you thinking of jumping jobs? Is your motivation money, career advancement, benefits or something else?
  • How does this job jump fit your long-term career plans?
  • Could you assertively talk with your boss before a jump about making necessary changes for your current work to be less frustrating and/or more meaningful and fulfilling? Your next job may have some of the same scheduling or staffing issues, and your courage to have this conversation prevents a “jumping from the frying pan into the fire” feeling of regret. A few who have tried this approach solved their job tension while getting a raise in the process.
  • Are you more valuable in the marketplace than you were before the pandemic or making a jump, and how many organizations know you are more valuable?


Here are 21 questions to ask before jumping jobs that boost your value in the marketplace.

  1. Have I gained advanced education to be more valuable to a future employer?
  2. Do I have specialized industry certifications? And is it posted on my LinkedIn profile?
  3. Have I attended industry events to strengthen my skill set?
  4. Have I volunteered for company or community leadership roles?
  5. Have I taken coursework to deepen my technology skills to become digitally fluent?
  6. Am I bilingual? Trilingual?
  7. Do I possess extensive years of industry experience? If so, how many years, and are those listed on my LinkedIn profile?
  8. Have I gotten involved in trade or industry associations as a volunteer?
  9. Have I joined trade or industry associations as a committee or panel member?
  10. Have I created or deepened income streams that are documented to benefit my current organization, which also reveals the potential I could bring to another employer?
  11. Have I created strategic partnerships or brand awareness for my current organization?
  12. Have I joined a Toastmasters Group to boost my public speaking skills? (
  13. Have I been asked to speak for local organizations as a recognized subject matter expert (SME)?
  14. Have I begun mentoring younger leaders inside the industry or another industry?
  15. Have I become recognized by YouTube, LinkedIn or another form of social media as an influencer?
  16. Have I created content on a personal blog, podcast, webcast or YouTube channel?
  17. Have I given a TEDx or Pecha Kucha presentation in my area of expertise?
  18. Have I written, co-authored or contributed to a book or article to highlight my expertise?
  19. Have I become a Wikipedia contributor or commentator on another web-based platform?
  20. Have I been quoted as an SME by podcasters, webcasters, bloggers, local media, national media or OTT media?
  21. Do I have a depth of social capital by being well established or well networked with strategic leaders across the eight streams of influence in the community or on a local/state/regional/national/global level (education, government, media, religion, business, sports, arts or family services)? The more influence you have, the more value you bring, and the more valuable you are to the marketplace.

“When you add more value, the marketplace rewards you with more value to share.”

Hopefully, a mental pivot occurred as you considered your marketplace value, instead of being stuck thinking about your current job frustrations. Wisdom is to move past being irritated with your work environment by pouring all your focused energies onto yourself. When you are more valuable to the marketplace, opportunities come your way faster because you are known as the person who can solve problems. It’s not about more money or their corporate brand—it’s about you and your personal brand as a respected professional.

“Take your job seriously, but don’t take yourself too seriously.” —Alex Trebek


Good news . . . the more of these factors you have built into your resume, the more you are worth to a future employer. Simply put, organizations pay you more because you have actively worked to become more valuable. However, if you haven’t done anything to create greater value in yourself or in your company and have shown no signs of growth, why would you expect more money or benefits from a new employer?  

The 21 questions are active steps you can take to strategically become more valuable because it shifts the perspective from “them” over to “me.” Atlantic writer Arthur Brooks describes this, “I know many people who talk of almost nothing besides their work, who are saying, essentially, ‘I am my job.’ This may feel more humanizing and empowering than saying, ‘I am my boss’ tool,’ but that reasoning has a fatal flaw: In theory, you can ditch your boss and get a new job. You can’t ditch you.”

Finally, before you up and quit your current position, consider the ripple effect of lost income in case the marketplace doesn’t value you, along with the “boomerang” effect of asking for your old job back after some time off ( Perhaps some of the job jumping has been about pandemic exhaustion more than being excited to work with new faces in a different place. If you are still feeling stuck, maybe the best plan is to contact a career coach to leverage your gifting and maximize potential before you take the leap. Jumping into the unknown can be terrifying. Making a careful move to jump into work that matters brings greater meaning now and is a strategic decision for decades to come.

Dwight Bain, MA, is the Founder of the LifeWorks Group in Winter Park, Florida. He helps people rewrite their stories through strategic change and is dedicated to helping people achieve greater results. Since 1984, Dwight has helped thousands of people across America as a Keynote Speaker, Certified Leadership Coach, Nationally Certified Counselor, and a Critical Incident Stress Management expert. He is a trusted media resource on managing major change and has been interviewed on hundreds of radio and television stations, has been quoted in over 100 publications, and is the author of Destination Success: A Map for Living Out Your Dreams. See more at:

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