WINSight // WIN NY x Rachel Kourakos: But, When?
WIN: But When? Workshop Recap
Wondering if you're in the right job? Struggling to figure out what path to pursue post-grad? Feeling overwhelmed about making a big pivot that seemingly has nothing to do with your current job or education? Trying to process a recent career move you just made?
On Wednesday, July 17th, WIN held our very first Career Coaching speaker workshop event with Rachel Kourakos, Founder and CEO of Rachel Kourakos Coaching & Consulting Inc., to unpack these questions and many more. Rachel is a certified professional coach from iPEC (200+ hours of training) and a master practitioner in the Energy Leadership Index.
The event drew 26 participants eager to soak up Rachel's insights, many of whom were looking to potentially pivot or get more grounded in their careers. Rachel assured us that through the 6-part workbook she was about to take us through, she would enable us to gain greater clarity and help guide the decisions we make on our paths forward.
The 1.5-hour session kicked off with Rachel sharing her personal career trajectory, including her experiences working at Morgan Stanley and Google before eventually pursuing the thing that lit her up inside – becoming a certified career and leadership coach. By sharing her journey, Rachel immediately set the tone for the evening, creating a safe environment where participants could be vulnerable with their life stories and grounding us in that all too common experience of sometimes feeling at odds with where we are.
As we made our way through the six-part workbook, Rachel would periodically pause to give space for women in the audience to share their insights and realizations as we jotted down responses to some of the thought-provoking questions. Through this, many women found at least one person they could relate or offer advice to across the room — one of the most beautiful parts of the evening. When asked at the end of the night how everybody was feeling in one word, responses ranged from “Inspired” and “Motivated” to “Validated” and “Calm.”
While we won’t share specifics of the proprietary workbook Rachel used, here are the top 8 takeaways we had:
Look down and you’ll see, we don’t wear cement shoes: Early on, Rachel emphasized that expecting to stay in the same job or industry for 20+ or however many years is impractical, as the only constant in life is change. At different stages of our lives, our desires and interests organically evolve. As our interests change, expand, or shrink, it's natural to wonder, 'What’s next?’. We shouldn’t fear making a change because we can always return to a previous position. Whereas avoiding change means leaving opportunities behind and potentially always wondering, 'What if?'“We are multifaceted. We are always changing.”
It’s less about if you are learning, and more about WHAT you are learning: One of the key pillars Rachel discussed was the importance of paying attention to what you are learning. She encouraged us to jot down 3 things we were currently learning in our roles, and consider whether they excite and interest us, provide incremental knowledge, and/or prepare us for future roles. If they don’t, it might be a sign to reassess or rethink your current position to ensure continued growth. “Is what you are learning setting you up for future you?”
When it’s time to go, lean out – not in: Rachel emphasized the importance of leading with integrity. Once you know it's time to move on, pull back from your current position to give yourself the mental and physical space to prepare. Chasing a promotion or going above and beyond in a role that no longer serves you will only distract and prolong your journey to the next step. As Rachel pointed out, it might feel wrong to stop being your high-achieving self, but you've already given that company enough of your attention and effort—it's time to focus on yourself.“If you are ready to leave, stop being a high performer, and don’t ask for a raise or promotion.”
The meaning of success is not one-size fits all: Rachel guided us through an activity to explicitly confront our own definition of success by writing it down. In doing so, we were able to ascertain is this truly my own definition of success or am I following someone else’s? She pointed out that in following someone else’s definition, we discount our unique childhoods, backgrounds, relationships, and perspectives. Once we discard the rulebook of others' expectations and honor our own, we can pursue a life that is authentically meaningful to us. “We are in a society that defines success in one way – but what does success uniquely mean for you?”
Career paths are often squiggly, not linear: Rachel emphasized the importance of not regretting any past experiences or leanings, even if they don't align with your future goals. Every experience contributes to your unique journey. For Rachel, drawing on her finance background has been instrumental in starting her own business. Don’t worry about how all the pieces fit together—trust that they will. “Everything I’ve done in my career has served me in that moment – even if you want to change careers, nothing was a waste.”
Check the source before taking the advice to heart: Before taking advice to heart, consider its source. Confiding in managers, mentors, or other higher-ups about your next steps can sometimes be met with friction, disgruntled sighs, confusion, or outright dismissal, ‘This is the dumbest decision you will ever make.’ Don’t let these reactions deter or discourage you, especially if they come from someone whose path you’ve decided not to follow. Label it as noise and continue confidently down your own path with grace. It’s not their job to understand your journey—it’s yours. “Anyone that has ever given you advice or said something that really rattled you – ask yourself, do you want to live a similar life to theirs? The answer will likely be no.”
Pursue your job search with intention, or don’t do it at all: Rachel cautioned against submitting 100 applications half-heartedly. While this approach sometimes works, it often leads to burnout, especially if you’re still working hard in your current job. Once you make the decision to move on, pursue your job search with intention—lean out of your current role, engage in thoughtful networking, apply to a select set of companies, and tailor your resume accordingly. Alternatively, if you’re uncertain about your next move, it’s okay to delay. Continue doing your best in your current role and set a deadline to reevaluate your situation in a few months. “Don’t half-job search, half not–either go all in, or don’t. If you do it half way, you’re burning at both ends.”
“This is your life. There is no practice round.” Enough said.
Thanks for reading, we hope this gave you something positive to reflect on, provided a new insight, or sparked a potential shift. We hope to see you at the next WIN event!
If you are interested in further connecting with Rachel, she works with individuals on a one-on-one basis, in group settings, and develops and facilitates workshop experiences for organizations, groups, and teams. She delivers keynotes on a broad range of topics and works with large organizations on leadership and culture consulting. You can get in touch with her or learn more here: https://www.rachelkcoach.com/
Written by Makena Naegele, WIN NY Programming Lead, Innovation Lead at Capgemini