What is the Future of You?

and Shu Shu Costa

A Conversation About Reflecting on the Past and Imagining Our Future Selves

Shu Shu: Looking back, there wasn’t a specific day my future changed. It’s not like I woke up and said, I’m going to leave my day to day school job today. It was a longer process of becoming more and more open and receptive to signals. Signals outside myself - people who I noticed were doing interesting work with educators and leaders, for example. Or new books (like David Whyte’s Crossing the Unknown Sea: Work as a Pilgrimage of Identity) that were capturing my attention. And signals inside myself - a desire to look at my work in different ways, a shifting of perspectives that lead me to take on different tasks at my school or seek to contribute to outside organizations in different ways. 

Like many of us, the long months of isolation, of relative quiet, during COVID also helped me to better understand myself - what motivated me, what gave me energy, what I missed about myself. The abrupt change in the structure of my day-to-day unlocked my routine and opened the door to imagining new work, new connections, and renewing forgotten interests and passions. It broke down and made clear the false boundaries in my internal narrative - “I should do this” or “the next step is.” I found myself able to put aside the need to be certain about the next move - we were all operating on courage during that time - and that brought new tantalizing horizons into view. 

In this way, the ultimate decision to walk into my Head’s office and share my news didn’t feel reactionary but a natural, mindful, even joyful evolution towards a future me. 

Moving beyond arbitrary and temporal, age-based change

Crystal: I agree, Shu Shu, that the last few years have provided many signals and opportunities that have led me to where I am today. For me, the intersection of my age and stage, the desire to create a work and life model that is not “9 to 5” (or 8 to 8!) opened up thinking about how to integrate more creativity about ways to work with schools and leadership in a consultative and human-centered approach. Instead of searching for external “opportunities” to come my way, I’ve reframed and renamed my internal hopes and dreams. 

As a younger person, I often would lay out my goals in five year increments. But there was no rhyme or reason for these five year chunks - it was all based on the ease of a round number and my achievement-oriented sense of accomplishment. Traditionally, when we envision our future self, it’s often based at an older age or another stage of life. 

“When the right job comes along, maybe then I’ll consider change.”

When I get my Master’s Degree, I’ll be ready for the next challenge.”

“Once the kids are older, I’ll have more time to consider….”

“After I retire, I’ll find time to pursue writing.

So perhaps it’s time to move beyond arbitrary and temporal, age-based change. Instead, imagine what you desire, what schools need and what the future might bring - to find the intersection that pushes us to imagine new possibilities.

Shu Shu: Agreed! I’m also thinking of the natural way our physical brains change with time. In Arthur C. Brooks' book From Strength to Strength he talks about how every human being moves from the fluid intelligence (the abundance of “raw smarts,” the ability to think flexibly and solve novel problems) of our 20s and 30s to crystallized intelligence - our ability to synthesize, to glean insights from our years of experience, to instruct - which grows in our 40s, 50s, and beyond. Some of our impulses to search or plan for a “future me” might also be an intuitive understanding of the evolution of our brains and mindsets, where we actually are in this moment of time.

Crystal: I wonder if, as we think about the future versions of ourselves, it might be interesting to utilize other ways of introspection and future planning. One way in is through the human-centered design process where we often begin by interviewing for understanding instead of outcomes. Imagine having a conversation with yourself or with a valued friend or colleague. Ask yourself some questions like “How Might I?” or “What if?”

What would I need to do now in order to envision a different me in the future?

How might I prepare for a changing world of tomorrow now? What skills and mindsets do I have and not have that would be useful as I change? 

What am I uncomfortable with or afraid of about the future that will certainly impact my life? Can I lean into it and learn more about it instead of avoiding or retreating?

What might my day-to-day life look like in 10 years? Perhaps even engage in some past-meets future scenario planning—what was your life like 10 years ago and what is it like now? What’s surprising about it?

According to Jane McGonigal of Imaginable, practicing this kind of future thinking around specific disruptions or changes can really build that cognitive flexibility and help create a more optimistic sense of the future.

Keep your core values at the center.

Crystal: As I reflect on my career, I didn’t fully imagine what and who I would be at age 50 when I was much younger. Although I had an ever-evolving set of possible goals and outcomes in life and career, I wasn’t sure “what” I truly wanted to do, “how” I wanted to live each day and “where” all of this might happen. I’ve found, though, that there have been constants, which have revolved around my core values. And although these too have morphed and evolved, my values of community, collaboration, purpose and creativity have stayed steady through many iterations of work and family life. 

The book Designing Your Life by Stanford d.School writers, Bill Burnett and Dave Evans, frames how we should spend our time in this values-based way: by looking at who you are, what you believe and what you are doing, you can strategize creatively and purposefully about the stages ahead. After you review your core beliefs, the next step is to imagine different versions of yourself in the future. The authors call these “Odyssey Plans” - how might you live a different version of your dream life in the future. There’s not one “right” journey - but many, perhaps infinite, possibilities. 

Don’t know which way to go? Keep your vision broad and real.

Shu Shu: That reminds me, Crystal, of a really useful tool I learned from one of my mentors, master facilitator and poet, Judy Brown. It’s called the Rule of Six. She explained it’s a Native American tradition that shakes us free of our more binary ways of thinking. “It’s either this job or that,” for example. Instead, the Rule of Six asks us to imagine six different paths forward, six different possibilities that are all true to your values. 

But here’s the trick. Brown says, don’t just choose a new path of the six. Sit with ALL six possibilities for a time. Observe what signals you notice as you gather data on all six options. What keeps knocking on your door? What keeps piquing your curiosity? Over time, one option may gather momentum. Some may merge together. Or all six may evolve through your future. 

Remember, this is just one step into your future.

Crystal: Who am I now as I’ve left a school community and a fulfilling job after 30 plus years? I definitely use my core values as my guide and I continue to think outside my previous boxes on what the future me – as a reshaped school person – might look like. I still have skills to learn and refine, particularly as I recognize the world in the next 5, 10 or 15 years will not be predictable. The world demands that we stay agile and evolve. 

Shu Shu: Perhaps the provocative film Everything Everywhere All at Once is an inspiration. How can we access and sustain the multiple versions of ourselves out in the multiverse? I’ve come to think of this move as just one step of many. Amazingly, courage builds on itself. Right now, I’m applying to graduate programs in seminary schools around contemplative leadership. It’s new and intriguing. And scary. And I don’t know where it’s going to lead. But isn’t that how the future always begins?

Join Crystal and Shu Shu next school year at a new L+D offering, an intimate writing retreat called Reflecting on Your Journey: Memoir and Meditation. Details to come.