Navigating Career Transitions: Insights from Cindy Gordon

When I pivoted careers, I reached out to those who helped me along my journey. As you can imagine, jumping into a new unknown job is scary (I’m also afraid of falling, something my therapist and I are working through, lawl). I took this opportunity to interview them to understand better what this transformation looked like from their end and help provide people who want to make this leap that your network is here to help! 

One of the key figures I had the privilege of interviewing was my colleague turned friend, Cindy Gordon –– we worked together at Policygenius. She was the former Chief People Officer and was instrumental in my development. Back in January 2021, feeling stuck, I reached out to Cindy, contemplating whether pursuing an MBA was the right move for me. Her attentive listening and thought-provoking questions helped me realize that my true calling lay in health and wellness.

Cindy and I delved into the challenges of feeling stuck or uncertain about career paths. She pointed out how sometimes we forget to check if it still aligns with our desires. Listening to our intuition and prioritizing self-preservation comes in. Our careers are dynamic, influenced by various factors, and it's essential to embrace those shifts and explore non-traditional paths that resonate with our interests and passions.

Cindy shared three exercises I found helpful in navigating a career transition.

  • The "Archaeological Dig." It's all about reflecting on our past roles, hobbies, and daily tasks to identify patterns and themes that bring us joy and energy. By recognizing these insights, we can uncover valuable skills that hold significant worth and utilize in various contexts.

  • The "Top 3." We find a moment of calm to envision our ideal work scenario and identify the top three aspects we seek in our next venture. Focusing on our present desires, not future or past expectations, is essential. By elaborating on what those three things mean to us personally, we establish guiding principles that will help us explore new opportunities

  • The "Brainstorm" is all about letting our creativity flow. We brainstorm potential work and environments aligned with our Archaeological Dig findings and Top 3 aspects. Seeking input from trusted friends, mentors, or advisors can spark new ideas and merge disparate passions. It's all about thinking outside the box and being open to exciting possibilities!

During our chat, Cindy highlighted the perennial question of pursuing additional education, like getting an MBA, when we feel uncertain about our career path. Sometimes the perceived need for more education stems from a lack of confidence or an avoidance of difficult decisions. We have a lot of skills, both acquired on the job and in life, that we can apply to the work we truly desire. It's all about trusting our intuition and being open to alternative routes that might lead us to a more fulfilling career.

We also discussed the importance of aligning our careers with our interests and passions. In today's ever-evolving work landscape, it's crucial to prioritize activities that bring us energy and fulfillment. After all, we spend significant time working, so why not make it count? And hey, it may take extra time and effort to achieve our goals, but exploring new connections, building strategic relationships, and being open to alternative routes can help us navigate the sometimes unpredictable job market.

Now, transitioning from a startup or non-traditional career path to a new industry or role might initially seem daunting. But guess what? Cindy assured me that it's often more accessible than we think. We can leverage our transferable skills from non-traditional paths by shedding limiting beliefs and embracing an abundance mindset. Skills like a propensity for learning, a service mindset, self-awareness, problem-solving through ambiguity, attention to detail, agility, and effective communication are valuable assets in any industry. We've got what it takes, folks!

During the interview I reflected on my successful transition into fitness training. I realized that living authentically, embracing vulnerability, and learning from every experience were the critical factors that led me to where I am today. Even the decisions that didn't go as planned provided valuable lessons and guided me toward my desired destination. So, remember that no decision in our career/life/etc journey is a mistake. Each choice and obstacle present us with an opportunity for growth and self-discovery.

If you feel stuck or need more clarity about your career paths, I encourage you to listen to your intuition and prioritize self-preservation. Take the time to reflect on your passions and skills through those exercises we talked about. Embrace your creativity and brainstorm potential paths that align with your interests and bring you joy. And remember, you have a network of remarkable colleagues, friends, and mentors here to support and cheer you on.

P.S. Let me know if any of you want to grab a virtual coffee and chat about your career journeys. I'm always here to lend an ear and offer support. Cheers!

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Embracing Change and Finding Pleasure: A Journey of Self-Discovery

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From WeWork Party Animals to Health + Fitness Coaches: A Conversation with Kim Kesting