Navigating uncharted territory

exploring the space between What Now? and what comes next

This post about uncertain transitions comes at a time that I am facing an uncertain transition of my own—the release of my second book Stop, Ask, Explore: Learn to Navigate Change in Times of Uncertainty in April, 2022. Like so many of the people I've worked with over the past decade, standing on the threshold of this new adventure is like being on top of a roller coaster--one part “this is amaaaazing” and one part “why the hell am I doing this?” So, in the spirit of throwing my hands in the air and going for the ride, here’s an excerpt from Chapter 1...

What Now? Moments and navigating uncharted territory

It is time now to explore the creative potential of interrupted and conflicted lives, where energies are not narrowly focused or permanently pointed toward a single ambition. These are not lives without commitments, but lives in which commitments are continually refocused and redefined. —Mary Catherine Bateson

I met Ashley Rigby at a mentoring event in New York City. We found each other at the refreshment table in the impeccably designed offices of a 100+-year-old furniture design firm with showrooms across the globe. Ashley filled a small plate with fruit and cheese and poured a sparkling water as she told me that she was a regional sales manager with the company and a mentor co-hosting the event. Over the 10-minute break between sessions I learned that she was a rising star at the company who had captured the attention of senior leadership. I also learned that, despite having ample opportunity for promotion and professional development, she was thinking about leaving to follow a dream.

"I started something with my mother and my sister," she told me. "A side gig really, but I'd love it to become something more." She went on to describe a community-based organization called Jam Program that they had designed together to provide space for women to network and share resources. Pilot events in Brooklyn, NY and Hartford, CT were already gaining momentum with cross-generational cohorts of professional women, and Ashley was confident that leaving her position and focusing on Jam Program full-time was necessary to take the project to the next level. It was apparent even in the short time we had together that Ashley and her partners had the vision, skills and capacity to make the new venture work. Perhaps even more importantly, the ambition and motivation were there. She was clearly hungry to do something meaningful, something with purpose, something that fulfilled her desire to be of service to others and to herself.

But she was also conflicted.

I watched the expression on her face toggle between excitement and hesitation as she described competing priorities and commitments at the intersection of a promising career, a high­potential passion project, and a very active family life with her husband and two young children. While she was more than capable of making tough decisions and following through on them, she was struggling to find a way to bring her best in three domains at once. Despite feeling stuck, Ashley was confident that she'd figure something out eventually. In the meantime, the plan was to keep her head down and juggle the job, the side hustle and family responsibilities until she could see a path forward-even though she knew her current pace was not sustainable. We set a time to grab a coffee the following week.

I've heard stories like Ashley's hundreds of times, in different forms and for as many reasons, as an educator and in my research and consulting practice. Whether I'm working with college students, helping early- to mid-career professionals to integrate their professional and personal priorities, or equipping established leaders and their teams to imagine the future of work, a common thread runs through their varied experiences. Regardless of the particulars, even the most educated, talented and experienced people can (and often do) get stuck when they stand on the threshold of a professional or personal transition.

Who among us hasn't, like Ashley, found ourselves operating at an unsustainable pace without a clear sense of how to lighten the load? Or received that text, call or email with news—good or bad—that upends our plans and forces us to reconsider the path we're on? From high-stakes disruptions like job transitions, to the daily challenges of dealing with a difficult co-worker, situations that scuttle our plans or challenge our intentions are an inevitable part of professional and personal life. And, while many of us may feel we have a gift for avoiding unwelcome surprises, even the most foreseeable life changes—like graduations, marriages, children and job promotions—can ignite the need to rethink how we live and work. Yet, even if we acknowledge that "the only constant is change" and accept that we need to "get comfortable being uncomfortable," most of us devote very little time or attention to the practice of preparing ourselves to navigate uncertain transitions. Though it's not for a lack of trying.

Visit any large bookstore in person or online and you'll find thousands of titles, that have sold millions of copies, on the topic of change. In the same way that most people know they should eat well and exercise to keep in shape, it's not news to anyone reading this book that the world is changing, and we need to build new capacities and skills to keep up. Perhaps you've already committed to having a growth mindset, building new skills and capacities, improving your EQ and becoming more empathetic, vulnerable and adaptive in your professional and personal life. Unfortunately, if you're like most people, you live somewhere in the gap between these ideals and reality—and the distance between can feel like a chasm. Add an interruption or disruption to the mix and we find ourselves in an all-too­ common conundrum: drowning in ideals, frameworks and change management approaches yet feeling perpetually under­-equipped when we face uncertain transitions.

Explanations establish islands, even continents, of order and predictability. But these regions were first charted by adventurers whose lives are narratives of exploration and risk. They found them only by mythic journeys into the wayless open—James P Carse

Too many tools, not enough practice

In an era where we've decided that more data and information is better, the sheer quantity of change-related tools and tactics can actually hinder efforts to navigate change, especially in times of uncertainty. In fact, attempts to apply one-size-fits-all solutions to nuanced challenges in shifting contexts can actually contribute to rather than alleviate the destabilization, disorientation and stuckness we feel when we face disruption. This is not as counterintuitive as it may seem. In the same way that a building contractor doesn't use every tool in the truck for every job, we don't need all of the tools at our disposal to navigate every part of every uncertain transition. Identifying the appropriate tools for the circumstances and engaging them in helpful ways, when they're needed, is a skill we rarely discuss or practice. As a result, we often confuse having a tool with knowing how to use it in practice.

I see this principle in action every time a person shakes a mobile phone at someone and says, "You have all of the world's information at your fingertips, why don't you know how to ____ ?" Assuming that access to technology means knowing how to apply the information you find there in context is like stepping into the lobby of The Library of Congress in Washington, DC (the largest in the world) and expecting to be able to apply the content in the 170 million items in your day­-to-day life. Unfortunately, much of our education, training and professional development operates on this assumption. That having access to information about change and uncertainty means that we actually know how to make sense of it and are able to draw useful insights that we can apply easily in dynamic circumstances. As a result, we spend tons of time, energy and money on learning about change rather than developing consistent and sustainable practices and approaches to help us apply what we learn in context.

Our relationship with speed and decisiveness may be partially to blame for this. In a world where faster frequently means better and efficiency is glorified, intentionally making time and space to stop, ask good questions and explore possible routes forward when we face uncertain transitions is viewed as a luxury at best, and indecision at worst. As a result, we often make quick decisions with partial information about situations that are new and emerging—then wonder why we feel lost in transition or wind up in places we never wanted to go as people we never expected (or wanted) to be. Ashley and her decision about whether to remain at her job or leave and focus on her startup provides a perfect example. We had a long coffee a week after that event, and it was clear that Ashley would likely benefit from carving out time to reflect on her work situation more deeply. I invited her to join me for a solo retreat. The experience involves a few days of completely unstructured time alone in a comfortable loft space. No mealtimes. No workshops. No massages or meditation classes. No alarms. No agenda. Just space, time and two three-hour conversations—one at the beginning and one at the end to help retreat participants to enter and exit the space with some intention (or not). There is no prescription for what people discuss in these conversations or how they spend their time between them. My only request (and it is only a request) is that visitors set aside their usual work and make space to step out of their normal routines. Most report that it is the first unscheduled time they've spent in years—and, for some, the first in their adult life.

Ashley, like so many others, arrived for her visit ready for a highly productive weekend. We laughed together as I pointed out the irony of showing up with an open canvas bag filled with more than a dozen leadership and personal development books. Over the course of our first three-hour conversation, it became clear that she had read everything there was to read about change, transition and building a successful career. Yet, when faced with the challenge of deciding how best to apply that learning to make sense of her particular situation, the "how to" and "what to" models fell short. I listened closely as she described her happy home, her love for her work at the design company, a growing dissatisfaction with her role there, and her deep desire to build Jam Program into something more. When she finished, I asked a clarifying question.

"Are leaving your job or staying at the company your only choices?"

She responded like most people do when I pose this sort of question: with a list of constraints and issues that completely justified her working theory that there were only two paths forward. She could stay at her primary job and keep the new business small or leave her job and focus on the passion project full-time. "Perhaps you're right," I pressed. "Tell me about how you identified those two options." Despite having thought about it deeply, she could not articulate how she'd arrived at these two choices. She talked about logic and common sense as she described the unconscious process she'd used to consider what was possible. We discussed the importance of considering less obvious potential choices, and I invited her to consider using her time on retreat to better understand her current context before deciding what might come next. I left her with large sketch pads, a white board, sticky notes, markers and a few prompts to help her get whatever was on her mind out of her head and in front of her. "Forget the books," I suggested. "Acknowledge that you stand at the threshold of a space between What Now? and whatever comes next that is ripe with creative possibility if you allow it to be."

The space between What Now? and what comes next

It's important to note here that I didn't know Ashley very well at the time and I had little context for what she wanted and what might be best for her career, her family or her life. I had no insight into whether leaving her job was the right move for her and, to be quite candid, I didn't care. Guiding her in a particular direction—toward greater success or a higher salary or greater wellbeing and slowing down was not my aim. My hope for her, and for anyone reading Stop, Ask Explore, is to build upon what Mary Catherine Bateson wrote so elegantly in the quote at the beginning of the chapter and help people at every life stage to recognize that the uncertain transitions we face across the span of our interrupted and conflicted lives offer tremendous creative potential to refocus and redefine our commitments.

If you’d like to read the rest of Ashley’s story and learn more about navigating uncertain transitions, visit www.stopaskexplore.com.