Asking Not Asking #34: Into the Unknown
TINA ESSMAKER / Creative Coach
Dear Reader,
Nearly two years ago, WNW and I launched this column as a home for creatives to write in with questions in the form of letters for me to answer. My responses share insights, lessons, and frameworks from my coaching practice and aim to give people practical steps to take as they confront career challenges.
Over the course of writing the past 33 columns, one of the most prevalent, recurring themes has been the question of how we deal with the unknown. Ambiguity, uncertainty, surprise, and the unexpected dot our careers as creatives, sometimes momentarily and sometimes for seasons.
We know what it’s like to look into the future and be unsure. We know what it’s like to follow our gut and take a risk to pursue a professional goal. We know what it’s like to take a leap with no guarantee that our decision will pan out the way we hoped. We accept that we will have to wrestle with the unknown, not once, but over and over again as we forge our paths as individual creators.
We are in that place again, now collectively, as we encounter a shifting landscape in the wake of the COVID-19 pandemic. We are confronted with a liminal season in which we have more questions than answers. We don’t know how long this season will last or what the next one will look like. There is much we don’t know. How will our respective industries change? What will it mean for our careers?
As we grapple with new questions in this season, I’ve revisited past columns that have addressed how we sit with and move through the unknown. Here, lessons we can take with us for today’s journey and future ones:
1. Find your North Star(s).
For my very first column, “Lost at Sea” wrote to me wondering how to take the next steps while feeling adrift. Even when we feel lost and unmoored, we can look to something consistent to guide us:
“Our lives ebb and flow, shifting below us, like the water you are sailing on now. But in every season of our lives, we can look up and see that glowing dot in the sky, pointing us north. What is your North Star, the thing—or things—that guide you home, give you a sense of purpose, and bring you joy? I encourage you to look up and see them in your life. Let them guide you.”
North Stars, or guiding principles, can remind us of what’s more important in our work, our creative home. Taking time to reflect on what those are for you can be powerfully grounding. Think about what gives you purpose, joy, and fulfillment professionally? If you have to encapsulate that list in 3-5 words, what would they be?
“Think about what gives you purpose, joy, and fulfillment professionally? If you have to encapsulate that list in 3-5 words, what would they be?”
2. Run to the roar.
A letter from “Frozen by Fear” came to me with a question of how to overcome fear to get from point A to point B in their career. In my response, I recalled my own experience with wanting to make a leap and being afraid as I sought advice:
“As I sat there in front of my mentor, I described my fear of abandoning a path I was already on—even though it wasn’t a clear path—to pursue something entirely new. ‘Run to the roar,’ she told me. She said I was imagining a huge, terrifying lion waiting for me on the other side of my decision, but she was sure that when I arrived on the other side, I would find a docile kitten and the roar would actually be a tiny meow.”
Times of uncertainty can lead us to re-evaluate our work and rethink our priorities. Perhaps we choose to revisit a dream or choose to pursue an alternative path than the one we’re on. Regardless there can be fear and trepidation. Often, we build that fear up into a roaring lion. However, as my mentor suggested to me, when we run toward that lion’s roar, we may instead find a docile kitten. What is your roaring lion and how might you run toward it?
3. Take the next step (you don’t have to see the whole picture).
We like to plan as far into the future as we can see, but what happens when we can’t see far? We can still take the next right step for ourselves, as I suggested to “Unsure” who wrote to me about trying to figure out their 10-year plan:
“Sure, it’s easy to connect the dots in hindsight, but for many of us in creative work, ambiguity is part of the process as we look ahead to what’s next. Instead of resisting, it can be helpful to accept ambiguity and learn how to navigate it.”
In times of ambiguity, resist pressure to make long-term plans and start with what you know to be true today. As you plan for next steps, think in short chunks of time. Perhaps you can make plans for the next month, week, day, or hour. Build on each step as you go and over time, you will look back and see your progress.
“Connecting with others is vital. Yet we often wait for others to reach out to us. We are all dealing with our own insecurities that can prevent us from reaching out first. Take a risk and reach out to connect or reconnect.”
4. Don’t go it alone.
When “Waiting to Be Seen” wrote to me about feeling isolated and alone on top of other work-related challenges, it reminded me of the importance of community. None of us can get to where we want to be without support. We bear witness to each other’s journeys:
“You are navigating a very normal part of the process, which is to say you are right on course. I see you, and so do all the others who have traversed this road—and one day you will bear witness as others wrestle with the same questions you’re wrestling with now, only you’ll do it from the other side of this experience.”
Connecting with others is vital. Yet we often wait for others to reach out to us. We are all dealing with our own insecurities that can prevent us from reaching out first. Take a risk and reach out to connect or reconnect with a friend or peer. You might find that they are facing similar challenges and can empathize or at least you can take turns listening to one another. You won’t regret making that call or sending that text.
5. Have hope beyond surviving the everyday.
Without a clear map for the future, it can feel like we are simply surviving day to day. In my response to a letter from “Freelance Life is Like A Drug,” I referenced wisdom from the book The Three Marriages by David Whyte, which feels more timely than ever:
“Happiness in the second marriage of work, like happiness in the first marriage with a person, is possible only through seeing it in a greater context than surviving the everyday.” Right now, it may feel like you are simply surviving moment to moment day to day, but it won’t always feel that way.
My friend and NYC-based Creative Director, Julia Parris, gave a beautiful analogy when I interviewed her recently for an article in 99U. She said, “In one hand you have to hold the larger vision. In the other, you hold the current situation.” We can acknowledge the reality, accept the many questions we are wrestling with, and still carry hope for the future as we step into the unknown. That is my wish for you in this season.
To thriving on the other side,
Coach Tina
Submit to the column:
Asking Not Asking is a bi-monthly column written by Tina Essmaker, a New York City-based coach, speaker, and writer who helps others live into their possibility. To be considered for the column, send and email to tina@workingnotworking.com with a short note about where you're at and where you want to be, and make sure to include the following:
- What you want more of in your work and/or life.
- Your biggest challenges to having more of what you want.
- What opportunities exist for you right now.
- What you've learned about yourself in the past year.
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