Breaking the rules early and often.

Emily K. Callaghan
7 min readDec 1, 2020

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Forging my own path has been all about breaking the rules. I’ve been wandering across academic and corporate hallways for more than 20 years and wondering, When do we remind students, professionals — ourselves — that we are free to make stuff up?

I often feel lost and misguided, underwhelmed, and completely uninspired. And then, without fail, I rediscover the confidence in myself, knowing not just that everything will be OK, but I will in fact make it so. I have a track record of making up jobs, moving to new places, and trying things out. That track record is where I find that confidence when I need it. It’s become a catalog of experiences and evidence that appeal to my emotional and intellectual brains. When I’m in self-doubt (emotional brain), that intellectual proof can really help push me into action. That first leap into trying something out is the foundation for future attempts that keep me in the uncomfortable learning zone. It’s a body of evidence that I not only can but AM designing my way through life.

So, how do we get stuck between the land of make-believe we know from childhood and the claustrophobic hallways lined with ladders of excellence and rigor we must keep climbing? How did we forget that we can shape our way forward? How do we show up for our professional lives with that same sense of play we had in childhood? Hop, skip, leap — making it all up is where the fun is.

Designing for the masses.

I started designing my life in high school. Of course, I didn’t know that was what I was doing. But I remember the scantron test that spit out potential professions for me. There was attorney and teacher. And graphic designer sounded kind of interesting. I talked with the guidance counselor about my future plans and read What Color is Your Parachute?, the career guidance classic flying off shelves at the time. The fact that 5,000,000 copies of the book had been sold left me feeling a little skeptical and a lot uninspired by the magic within. The linear progression of building professional skills in order to gain some (false) sense of clarity that results in career satisfaction and security? To a teenager, it all felt like a bogus checklist.

I received my bachelor’s degree in journalism from a “top” university and completed an internship in my field. I meandered from design to journalism and lost focus many times over. Life hit me hard in college, and there was a lot to navigate outside of my studies. I didn’t graduate at the top of my class nor did I earn a resume-worthy GPA. But I had teachers that believed in me and believed I could do better. I juggled a good mix of too much college fun, mental health stumbles, and somehow working too much while also amassing more student loans than I would be ready for when the bills started coming. I took five years to graduate college after buzzing through high school in three. I was fervent in my dedication to friends and work, and lazy in showing up for my studies. I always juuust made it.

I scoured the newspaper for jobs. I typed, sealed, and sent letters of application. I had my resume printed on that extra nice paper at Kinko’s. I was scattered and hopeful, but mostly confused. More than anything I needed a reliable income to transition me out of the restaurant industry and into student loan repayment.

Photo by Jungwoo Hong on Unsplash

What was all that though? The scantron, the internship, the degree. Was it all just asking for permission to be someone? To become an adult? A professional? The education, the path, the lines and queues, categories and ranking — did any of it really make any sense? There was a cap and wrinkled gown, my very own laptop computer, and even a printer. But now what?

My path, until then, felt like a collection of steps and rules. When was that going to add up to something more — a full story or way forward? I was dizzy with expectations and waiting to be accepted, approved, and moved ahead in line. When did I forget how to design my way?

What is the path to unmolding? How do we
give ourselves permission to be ourselves?

Designing for me.

Fast forward. With a few years of ordained professional experience under my belt, I started to remember my creative self — the me that didn’t always follow the rules but challenged them instead. Once I grew the confidence to know I could earn a living and support myself, I had a chance to remember. To remember what I can make, to remember to believe in myself.

I remembered the feel of my ballpoint pen on the official, triplicate carbon copy form as I wrote my petition to the superintendent of the Parkway School District, making the argument to graduate high school a year early. I had the credits, I had the plan, and I had the guts to try. It worked.

I remembered making my case to my restaurant’s area director, explaining why I was — at 18-years-old with exactly two months of restaurant experience — the best pick out of all her employees to travel with a select team (of friends!) to open a new restaurant and train a staff of 100. It worked again.

And later, I remembered feeling the ground shake beneath my professional confidence as big leadership changes and political storms put my role and my dream team organization right in the line of fire, despite our incredible work. By my thirties, I’d finally found the footing and bravery to navigate the C-suite, develop people, travel the world, and advocate for myself and the value of my work.

My catalog of courage sprouted from that letter to my high school superintendent. That one small try, the willingness to make and to believe. My well is now full of lived stories, of making and believing, and it’s fueled me in my most doubtful times. Looking back and seeing myself as bold, brave, and successful has always been a quick hack to find a new spark that inspires me to get going and start trying. It works.

Let me be clear. I’m still as questioning as I am daring. I’ve stumbled through a journey that looks more polished on LinkedIn than is the lived truth. And that genuine undulation of feeling and learning is what makes us interesting. We build resilience and witness how capable we are of trudging forward through sticky mud that feels like quicksand. And better yet, it’s what makes us great learners, dear friends, and partners.

Which parts of your path were pre-established?
Whose expectations are you living up to? Why?

Community-based learning.

I am deeply privileged as a white cisgender woman; I grew up with more than enough comfort. And I’ve always been surrounded by people who have acted as signals and spotlights. Never choosing for me or pushing me with their own agenda, these relationships have served me in riches. Through them I’ve learned the value of modeling, mirroring, critical feedback, and loving nudges. That courage catalog is often referenced, but it’s a community of support that has propelled me to try and try again.

Modeling. My Aunt Wendy was always the coolest. She was creative and stylish and would bring candy and rollerskates when she visited. I saw her pursue her education, earn degrees, follow her career, and make a big move to Washington, D.C. I could see that her path was driven by what lit her up. I learned from her that intellect and creative expression are a path to independence and success.

Mirroring. Heidi was a colleague and dear friend in graduate school. She lived an extraordinarily inspired, artful life, and I felt proud to know and work with her. Heidi was there the first time I ran a brainstorm session, chock full of nerves and sweating through my shirt. Afterward, she approached me with the warmest smile and said, “You belong in the classroom.” Never before had I imagined myself as capable nor gifted in the way that she reflected back to me.

The modeling of others helps you see where you might be or who you might become. And mirroring offers positive reinforcement around your talents and strengths, and helps you see your potential. But we can’t stop there. We still need that tough love kind of feedback that helps you identify areas to improve and creates the next turn in the path to keep you challenged and growing. It’s not easy to find, but when you do, lean in and listen closely.

Critical feedback. It hurts so good. I crave feedback from Carissa, one of my favorite collaborators, knowing there might be a little sting in her honesty but also a big fat promise of making my work and me better. She catches my blind spots and helps me slow down so I can re-look when I’ve zoomed too fast or made too many assumptions. And this beautiful mix of love and honesty is a real treasure.

Loving nudge. It’s the thing that works with surprising depth and can endure for years, hopefully forever. When I was nervously navigating my 30-something professional crisis, my dad said: “I’m glad you have this challenge in front of you. Because I know you’re up for it.” I go back to his words all the time as I step into offering these same loving nudges to myself and others.

Who are the people in your life who can effortlessly mirror your greatness?
See your blind spots? Nudge you lovingly?

I’ve designed jobs, capabilities, organizations, and now my own company because I’ve been building my practice of make-believe. I’ve proven to myself that I can take risks, push boundaries, and continually evolve my work and myself. There’s proof in the trying and power in community.

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Emily K. Callaghan

Owner @ DESIGN+ / Lecturer @ Hasso Plattner Institute of Design at Stanford (affectionately known as the "d.school")