On Taking the Leap, Liminal Spaces, and Lessons Learned
Field Guide Entry by Ashley Kera
I spent over a decade in people operations, talent strategy, and program management. My most recent corporate role was scaling and leading a multimillion-dollar analyst program at a top-tier global law firm for more than seven years, where I also managed and coached hundreds of professionals across global offices.
Alongside my corporate career, I earned a master’s degree in clinical psychology and an executive and organizational coaching certification from Columbia University. I operate through that lens today, approaching people and systems that help me better support organizations and individuals in my work.
Objectively, my career looked like it was going well, and I was proud of what my team and I built. At the same time, I was not happy and burned out. The hours, the pace, and the expectation to always be available were no longer compatible with the next chapter of my life, which was about creating space for family.
For years, I asked myself, “What if?” What if I tried something different, even if I was not fully clear on what it would be? It's easy to stay comfortable and settle, but I was also living in "active regret," longing to take a risk but also afraid of the consequences.
Eventually, I made the decision to take the leap. I thought the best time to do it would be before starting a family, but soon after leaving, I learned I was pregnant. In retrospect, I thought I had a plan, but really I only had an idea. I was forced to step into the fear, get really uncomfortable, and I learned a lot about myself and also the challenges of building on your own while also creating a little human.
Lessons on Taking the Leap:
There is no one set approach. Some people polish a brand and website before leaving. Others, like me, started by taking on clients through referrals and conversations. Both paths work. The key is choosing the one that gets you moving.
A pause can be strategic. If you are facing burnout or need a career pause, permit yourself to step back before building what is next. Rest is not wasted time. It is the foundation for clarity, energy, and better decisions.
Plan financially, with precision. Do not just hope it will work out. Build projections, create a buffer, and know your minimum viable income. Consider benefits, healthcare, and other essentials alongside income and expenses. Flexibility matters, but so does clarity on the numbers.
Flexibility is non-negotiable. One of the few guarantees in life is change. Whether by choice or by circumstance, things will shift. Iteration is not failure. It is how you adapt, grow, and sustain.
Let your values guide your choices. Get clear on what you want, what you need, and what is realistic in this season of life. Do not build a “should life” that looks good on paper but pulls you away from your values.
Clarity comes from action. Confidence does not appear first. It is built by putting in the reps. Small steps and small wins compound into momentum and direction.
Mindset and community matter. Be mindful of your self-talk. A learner’s mindset keeps you moving when doubt shows up. Surround yourself with people who remind you of your why and hold you accountable when it gets hard.
Visibility and networks create opportunity. I chose LinkedIn and showed up consistently. Pick the platform where your people are, then share your work and voice. Relationships, both online and offline, are growth strategies as much as support systems.
Design systems that work for you. Learn your strengths and weaknesses, then set up tools and accountability that keep you consistent. In corporate roles, structure is handed to you. On your own, you need to create it and keep it simple.
Get comfortable with discomfort. At first, there is an adrenaline rush in leaving the familiar. Then reality sets in, and you may question your choice. Growth lives in that tension. Accept where you are, even if it is not where you want to be yet, and keep making the next best decision
The hardest part is often navigating so many changes at once. I was leaving a familiar environment, starting a business, recovering from burnout, and becoming a mother all at the same time. Even now, it means balancing being a present mother, doing client work, continuing to build my business, and managing the many responsibilities of adult life. That ongoing tension is challenging, but it has clarified my priorities and strengthened my resilience.
So my advice to you is to start where you are, even if it is not where you want to be yet. Focus on the process and the progress you are making rather than fixating only on the outcome.
Do the inner work to clarify not only what you want to do, but also who you are and what you value. Pair that awareness with action. Celebrate the small wins, trust that clarity comes with movement, and stay open to pivots along the way.
You do not have to have it all figured out, and few people actually do. You may choose in the future to return in-house or take another path. Stay open-minded but be proactive in creating options for yourself without overwhelming yourself. Don't do things for validation or because you think you "should" but rather because you want to. Don't underestimate the power of small, consistent actions. Keep moving forward in the direction you think and feel is right for you and aligned with your values and other priorities.
Field Notes contributor since 2025.
You can also follow Ashley on LinkedIn.
About Ashley
Ashley Kera is the founder of Kera Coaching & Consulting, where she partners with scaling companies to fix the people systems that cost them time, money, and trust, and coaches driven women navigating major life transitions. With a master’s in clinical psychology, a coaching certification from Columbia University, and more than a decade of experience in people operations, she has scaled multimillion-dollar talent programs and coached hundreds of professionals across continents. Ashley is known for bringing clarity, accountability, and care to both organizations and individuals. She helps companies build sustainable infrastructure for growth and helps individuals rebuild identity, direction, and self-trust during times of transition.
