Navigating Transitions

Olga Skipper
3 min readMay 10, 2024


Do you ever feel disoriented and stuck, like everything around you has shifted but you’re unsure how to respond?

Hey there, I’m Olga, an executive coach. I thrive on meeting clients at the end of one chapter, guiding them through the in-between, and witnessing the dawn of something new.

Lately, I’ve noticed many people grappling with the transitions brought on by our changing world: COVID-19, geopolitical shifts, natural disasters, economic fluctuations, and more.

I define transitions as the inner and outer processes of crafting a new life and reality when changes, whether within us or around us, come into play. It’s that feeling of no turning back yet not knowing the way forward.

In this article, I aim to offer guiding principles for navigating personal transitions and those of the communities, societies, and countries we’re part of. Whether you’re seeking a new job, exploring entrepreneurship, embracing parenthood, or relocating, this list could prove useful. Feel free to use it, share it, and reach out if something’s missing.

Let’s Define Transitions

Transitions encompass both inner transformations and external changes that redefine our identities and reshape our priorities. They demand that we embrace uncertainty, rely on our instincts, and cultivate resilience. Whether launching a business, changing careers, or welcoming a new family member, transitions require courage, adaptability, and a readiness to embrace the unknown.

These journeys offer invaluable lessons and opportunities for personal growth, pushing us beyond our comfort zones and helping us become the best versions of ourselves. While each journey is unique, the essence of transformation remains constant: emerging as a new person, unexpected yet necessary.

The road ahead may seem daunting, filled with uncertainties and unexpected turns. However, by embracing a set of guiding principles, you can navigate these transitions with clarity and confidence.

Rule #1: New Path, New Perspective

Transition is a deliberate choice, not an automatic process. Even when the destination is unclear, approach the journey with intentionality and self-compassion. Recognize that transitions demand energy, so allocate it wisely.

Rule #2: Embracing Endings

Every transition begins with an ending. Prepare yourself for shifts in relationships and roles. Surround yourself with a supportive community that shares your values to navigate this period of change.

Rule #3: Balancing Forces

Acknowledge the push and pull of transition. While progress propels you forward, there may be moments of resistance. Stay resilient and trust the process.

Rule #4: Embracing Change

In moments of doubt, see transition as a blessing rather than a curse. Accept its gifts and commit to making them work. Resistance prolongs discomfort, while acceptance fosters growth.

Rule #5: Protecting Progress

Safeguard your transition in its early stages to facilitate exponential growth later on. Gradually involve others, but limit the influence of skeptics. Trust your instincts and proceed at your own pace.

Rule #6: Harnessing Inner Resources

You possess more tools and wisdom than you realize. Draw upon past experiences and innate strengths to navigate challenges. Stay curious and open to learning.

Rule #7: Embracing the Journey’s Timeline

Acknowledge that transitions unfold at their own pace. Avoid rushing the process and allow yourself time to adapt and grow.

Rule #8: Discovering a New Identity

As you evolve, embrace the emergence of a new self. Adjust your inner narrative and realign your support network to reflect this transformation.

Rule #9: Nurturing Relationships

Recognize that your transition may impact others. Approach interactions with empathy and understanding, while prioritizing your own well-being.

Rule #10: Embracing Uncertainty

Transition defies logic and unfolds unpredictably. Embrace the unknown and focus on what truly matters. Find your balance between action and reflection, recognizing that perfection is not the goal.

Transition is a nonlinear process, a dynamic journey teeming with challenges and opportunities. By integrating these rules into your approach, you can navigate transitions with resilience and purpose. Remember, it’s not just about reaching a destination but embracing the transformation along the way.

P.S. During lunch with a friend, she shared a valuable insight from a transition she underwent eight years ago, the one that helped me to finish one of my transitions and embrace the new beginning: “The transition changes you, but at some point, you don’t remember the transition.”



Olga Skipper

Executive coach and Advisor for Tech Founders and Entrepreneurs. Asking uncomfortable questions.