When the Next Chapter Has No Playbook — Finding Direction in Times of Transition
Originally published on Digoshen in September 2026, as part of the Beyond the Old Playbook podcast and reflection series.
Transitions are rarely as straightforward as leaving one chapter behind and beginning another. Whether we are changing professional roles, reconsidering our ambitions or navigating a broader transformation in life, the familiar structures that once provided direction may no longer apply.
This reflection explores what happens when experienced professionals and leaders find themselves between what has been and what has yet to emerge. As part of the Beyond the Old Playbook series, it considers how uncertainty, identity, purpose and personal renewal intersect, and why navigating a new chapter may require something different from the capabilities that helped us succeed in the previous one.
Reflections
Much of our professional identity is shaped by the roles we hold, the responsibilities we carry and the achievements through which we define success. These provide meaning and belonging, but they can also make transitions difficult when familiar titles, expectations and structures begin to change.
We often approach a new chapter by searching for another plan, another goal or a clear destination. Yet meaningful transitions may require us to remain in the space between endings and beginnings long enough to discover what genuinely matters.
For experienced leaders, this can be particularly challenging. The instinct to act, solve problems and establish direction may need to be balanced with reflection, curiosity and openness to possibilities that were not previously visible.
Perhaps the next chapter is not about replicating past success in a different setting, but about allowing our experiences, values and aspirations to come together in new ways.
The challenge is to recognise that uncertainty is not necessarily a sign that we have lost our direction. It may be the space in which a different sense of purpose begins to emerge.
The Message
When the next chapter has no playbook, the task is not simply to find a new plan, but to discover who we are becoming and what we want to contribute.
Transitions invite us to move beyond familiar definitions of success, embrace uncertainty and remain open to new forms of meaning, contribution and belonging.
Sometimes the most important step forward is not knowing exactly where we are going, but having the courage to explore what might come next.
When entering a new chapter, do you find yourself searching for a familiar playbook, or allowing space for something different to emerge?
Read the full reflection here
When the Next Chapter Has No Playbook — Digoshen
About Liselotte Engstam, Digoshen & Novisali
Liselotte Engstam is an explorer of perspectives, an adventurer of ideas, a pathfinder of meaning, and a guide of timeless transitions. She bridges the worlds of board leadership and art, helping organizations and individuals navigate disruption while nurturing creativity and reflection.
As founder of Digoshen, she works with boards and leaders to expand future insights and reduce digital and sustainability blindspots. Through research, networks, and executive programs, Digoshen supports responsible value creation in the digital and sustainable age, contributing thought leadership via books, articles, events, Digoshen Exploring Leaders podcast, and blogs.
She also serves as Chair of the Boards Impact Forum in collaboration with the World Economic Forum and the Climate Governance. The Forum convenes board members, thought leaders, and experts in dialogues, webinars, and collaborative events, accelerating action on climate, AI, and sustainability.
Through her artistic practice as Novisali, Liselotte explores creativity and meaning. Her watercolors, digitally reimagined, invite reflection and renewal, offering perspectives that connect head, heart, and hand, and complementing her work with leaders and boards.
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→ Find more about Liselotte at www.liselotteengstam.com and her Google Scholar page
→ Explore Liselotte’s art and reflections at www.novisali.com and follow on Instagram @novisali_arts