top of page
  • Writer's pictureDr. CK Bray

Navigating Your Career: 5 Questions to Ask Yourself

The working world is changing so quickly that you will most likely have to navigate a career path you didn't expect and make changes you didn't want to. This can be especially difficult at a midpoint in your career. It is a time when the weight of unmet expectations can feel particularly heavy, and the realization that our dreams and aspirations may never happen. But amidst this reckoning lies a profound opportunity for growth—a chance to pause, reflect, and carve out a path that aligns more closely with our true desires.


Chip Conley, the founder of the Modern Elder Academy, vividly describes this midlife transition. He describes the first half of life as an era of accumulation, during which we enthusiastically collect friends, achievements, and possessions. Yet, as we enter the second half, Conley suggests it's time for editing—a period of discernment during which we sift through our experiences to identify what truly matters.


But how do we embark on this journey of self-discovery amid the hustle and bustle of midlife? Ebony Joyce, founder of Next Level Career Services, believes it starts with asking the right questions. Here are six pivotal questions to ponder as you navigate your career in midlife:


1. What will I regret not having done or learned ten years from now?


Though often viewed negatively, regret can serve as a powerful teacher, according to Conley. He encourages harnessing the power of anticipated regret by imagining the disappointment we might feel in the future if we fail to take action today. Research suggests that maintaining curiosity and embracing new experiences are vital ingredients for a fulfilling life. So, why wait? Dive into that hobby or book that trip you've always dreamed of before it's too late.


Helpful Tool: Take inspiration from Conley's own midlife adventures, like learning to surf, speak Spanish or take up the harp. It's never too late to explore new passions and expand your horizons.


2. How do I tap into my purpose?


Many of us find ourselves influenced by external pressures early in our careers, whether it's parental expectations or societal norms. But as we reach the midpoint of our lives, Joyce urges us to break free from these constraints and focus on our own dreams. By reflecting on what truly excites and motivates us, we can identify potential career pivots that align more closely with our passions.


Helpful Tool: Recall moments from your past when you felt most fulfilled and alive. What activities sparked joy and excitement? Use these insights to guide your career decisions moving forward.


3. What mastery or gift have I developed that I can offer to the world?


By midlife, we've accumulated a wealth of experiences and insights that can be leveraged to make a positive impact on others, says Conley. He suggests reflecting on our strengths and talents through exercises like Peter Drucker's "five whys." By delving deeper into our unique gifts, we can uncover new opportunities for personal and professional growth.


Helpful Tool: Consider the story of David Viscott, who believed that the purpose of life is to discover our gifts and give them away. What talents or skills do you possess that can benefit others?


4. What do I want my days to look like?


Rather than focusing solely on long-term career goals, envision your ideal daily routines. By thinking smaller and considering the details of our day-to-day lives, we can gain clarity on the type of work-life balance we truly desire.


Helpful Tool: Picture a typical day in your ideal future. Who do you interact with? What activities bring you the most joy and fulfillment? Use this vision to guide your career decisions.


5. What trade-offs am I willing to make — or no longer willing to make?


It's natural to second-guess past decisions and contemplate what might have been. But as Joyce reminds us, it's essential to recognize that our priorities may evolve over time. Whether it's prioritizing our careers or personal lives, we must make intentional decisions that align with our values and aspirations.


Helpful Tool: Reflect on the choices you've made and the sacrifices you've endured. Are these trade-offs still worth it, or is it time to reassess your priorities?


As our working lives continue to progress and change, it is important to be aiming at the right target and these questions can help you navigate with clarity and purpose.


**This article was adapted from Rebecca Knights Feb 2nd, 2024 article in the Harvard Business Review called, "6 Questions to Ask at the Midpoint of Your Career."





Cover of book How To Raise Remarkable Kids Without Talking To Them


bottom of page