20 Questions to Guide a Seminal Career Change

When you find yourself at a fork in the road of your career, how do you decide the right path to take next? These 20 questions may help.

3 years ago I tapped-out as an Ad Executive.  It had been 20 years of blood, sweat and tears – quite literally.  About 90% of the time I loved it, but that number had started to dwindle. A career shift to better accommodate my evolving situation was in order, and I knew the solution wasn’t just about swapping the logo on my business card. I wanted a seminal change that brought enhanced purpose to my life, a decent paycheck, and flexibility with family demands.  It was a tall order, but I’m not one to be intimidated.

I began a deeply personal exploration to determine the best way forward.  As we find ourselves in this age of change, significant unemployment, and workplace evolution, perhaps you can relate to the desire to reevaluate as well.

But how do you proceed with a potential career change?

In advertising, good campaigns start with facts, inspiration, and a key insight in order to enable the creative process to effectively begin.  Having written hundreds of creative briefs in my career, I leveraged that approach in my own assessment. And like before, it really became a methodical process in finding my “why” and “how”? 

In my research and exploration I asked myself the following 20 questions:

  1. What values and passions do you hope to preserve in your life?
  2. How would you describe yourself in one sentence?
  3. What frustrates you about your current job?
  4. What do you love about your current lifestyle? 
  5. What level of income do you need to budget 50% of spend to needs, 30% to wants, and 20% to savings? 
  6. What are your learned skills?
  7. What are your innate talents?
  8. What behaviors, products, or services are trending or necessary in today’s society that may align with your interests or experience?
  9. What have you already accomplished?
  10. What are you most proud of?
  11. What would you still like to accomplish?
  12. What brings you joy, or what used to bring you joy that maybe you haven’t been able to do in a long time?
  13. What do you want to ensure you have time to do daily or long term (fitness, self-care, dinner with family, sleep, etc.)?
  14. In addition to yourself, who do you live for? 
  15. Who do you want to surround yourself with daily and where?
  16. Who’s life would you like to make a difference in?
  17. How might you enable some of these ideas above? Does it take additional education? Is that feasible?
  18. What’s your life’s currency – is your success measured in things, or a life well-lived?
  19. Do you think you need a full career reboot, or can you just make some small changes within the situation that you’re in now? 
  20. What legacy do you hope to leave?

What was interesting about the discovery process for me was that my initial answers to these questions weren’t necessarily my final ones.  If you’re like me, consider writing a first draft response then sleep on it. Do your research.  Read books about topics you’re passionate about even if the connection doesn’t seem clear.  Take a lot of long walks to get your mind flowing. Test out ideas by writing about it.  Bounce things off your friends and family. Take an online course in a new subject.  And finally, be cautious before you throw the baby out with the bath water – maybe you just need a new side-hustle or enriching volunteer opportunities.

I should also mention that if the job change you’re now seeking was pushed upon you rather than your proactive choice, it can feel super unsettling. I’ve been there too. In either case – proactive or reactive, as with any change, you will better prepared to adapt when you are excited, receptive, authentic and humble.  

With all that considered, it is certainly ok if a big change still doesn’t feel right or feasible. Stay the course! But, perhaps, it will be helpful to consider refreshing your mindset: not, “I have to work” but rather, “I choose to work.” And I do. In fact, it’s a line I previously used frequently in my interview process and with my internal teams. I wanted my company to know that I chose them as much as they chose me – it’s a relationship. I chose to succeed because it was important to them and to me.  I chose to embrace every opportunity that came my way as a sign that the universe was giving me a chance to learn and grow, rather than seeing it as unforeseen challenges that happened to me.  

In whatever path stands before you, strengthen yourself for the next chapter by considering cleaning up your diet, making time for self-care, trying beneficial breathing techniques, and getting regular exercise to support your mental and physical fitness. I truly believe that you will be more successful in your interviews or in your entrepreneurial pursuit if you’ve created the proper emotional and physical foundation.  This may be a fork in the road that you didn’t see coming, but it could be an absolutely beautiful ride.

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Danielle is Founder of The Well-Intended® and an award-winning Executive Wellness Coach.  If you’d like to learn more about how The Well-Intended can help your organization click here to review our Corporate Renewal Programs and/or email danielle@thewellintended.com to discuss 1-on-1 Virtual Executive Wellness Coaching.

iStock photo credit: BlackJack3D

Disclaimer: “The Well-Intended”, and its associated blog and social media pages are owned and operated by The Well-Intended LLC and does not provide medical advice.  The Well-Intended’s author is not a physician or licensed medical expert.  The content provided shares perspective on a personal wellness journey and healthy lifestyle approach practiced by its owner in order to achieve their own health and happiness.  Please consult your physician for advice and/or guidance regarding specific concerns with your own health, vitamins, supplements, fitness plan and/or anything else health- or wellness-related.

Danielle has a degree IN advertising from Michigan State University (Go Green!) and a degree OF sarcasm in life.  Her perfectly imperfect pursuit of wellness is rooted in the research and practice of wellness in efforts to revitalize her mind, body and spirit after 20 years as an executive in the advertising industry and a hobby of collecting home addresses in Detroit, San Francisco, Los Angeles, New York City and Atlanta. You can reach her on The Well-Intended social channels or at danielle@thewellintended.com.

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