My Wild Bio — the full story of how I got here.
A More Comprehensive HERSTORY
The full story of Sasha Cagen — leadership coach for women, author, movement founder, tango dancer, and lifelong non-linear path-taker. For women founders, leaders, and changemakers who want to know who they’re working with.
If anything has been constant in my life, it’s been change — and the willingness to tolerate the discomfort and fear of risk-taking and trying new things to feel alive. Every unexpected turn, every chapter that looked like a detour, turned out to be training for the work I do now: helping women lead with more confidence, authority, and presence.
Here’s where it all began.
I was born in Providence, Rhode Island, to an RN and public health professional who taught me to write to-do lists, to never rely on a man for my money, and to take good care of myself while also caring for others.
My father is a real estate lawyer and copyeditor who taught me the importance of being involved with the community. We canvassed together for presidential candidates in many states. My parents instilled social responsibility in me early — and that thread of civic engagement runs directly through my coaching work with political leaders today.
I grew up in Cranston, Rhode Island attending public schools. I was lucky to get into the gifted and talented program in fourth grade. My teacher Mrs. Santos nurtured a love of the creative process in me that goes on until this day. She made me believe I could be a writer — and in doing so, she modeled what a great mentor does: she saw something in me before I could see it in myself. That’s what I try to do for my clients.
My high school wasn’t too great. The bathroom stank of smoke, I didn’t have a high school boyfriend but I had a strong group of female friends. Strong female friendship has been a theme in my life.
I obsessed about getting into a “good college” where I would “find my people,” and worked hard to become the high school valedictorian. I started off at Amherst College in Western Massachusetts, a competitive school with lots of portraits of old white men on the walls. I never felt at ease at Amherst.
After three semesters, I transferred to Barnard College, the women’s college that is part of Columbia University, and felt much more comfortable in a big city. I took advantage of being in Manhattan by working at Self, when I was known as the girl who wore thrift store outfits in the Conde Nast building (350 Madison Avenue, where Vogue and Glamour were also published).
During college, I published a zine called Cupsize with my friend Tara Emelye. Doing that zine helped me to find my voice as a writer. I also interned and wrote for The Village Voice.
At 20, I appeared in the front row on Ricki Lake to advocate for bisexual visibility and acceptance within the gay community. Looking back, that was an early act of using a public platform to advance an idea I believed in — something I’ve been doing in different forms ever since, and something I help my clients learn to do with their own messages.
Learning to Build Messages That Move People
During my twenties, I worked in the labor movement doing PR and communications at a firm in San Francisco’s SoMa neighborhood. I learned how to craft messages for movements — how to take a complex idea and make it land with a general audience, how to build coalitions, how to get coverage that actually changes things.
That experience was formative in ways I didn’t fully appreciate at the time. Today, when I coach clients on their messaging, their media presence, or their ability to communicate their vision, I’m drawing directly on what I learned in those years. I continue to support the critical importance of the U.S. labor movement.
That job wasn’t meant for me for longer than two years. I was crying in the bathroom at work because I couldn’t write white papers anymore. So I traveled to Cuba. I studied Spanish for a month at the University of Havana.
Travel has often served to jumpstart new phases of my life. Spending time in other cultures has been an important way to get new inspiration — and a lesson I share with clients about the power of shifting contexts when you feel stuck.
When I got back, I gstarted my own magazine, To-Do List. To-Do List was named Best New Magazine in the alternative press, awarded by Utne Reader in 2000.
An essay published in the first issue — “People Like Us, the Quirkyalones” — struck a deep chord in people’s hearts worldwide, leading to a book with HarperCollins in 2004 and a word that eventually made it into dictionary.com.
Quirkyalones are people who prefer to be single rather than settle for less than the relationship they really want.
Quirkyalone made a major impact for readers worldwide who felt like something might be wrong with them because they had been single for longer than they expected. The book continues to have a profound validating impact. Many people who come to work with me as clients identify with being quirkyalone, or quirkytogether.
My second book, To-Do List: From Buying Milk to Finding a Soul Mate, What Our Lists Reveal About Us, explored what our lists reveal about our inner lives. I spoke at the Authors@Google series about my to-do list research — one of the most enjoyable speaking experiences of my career. My fascination with how we organize our intentions remains strong, and I regularly share list-making and reflection exercises with my coaching clients.
The Silicon Valley Chapter — Losing Myself along the Path to Finding Myself again
After To-Do List, I felt pressure to “get serious” about making more money. I co-founded a street fashion social network called StyleMob with my friend Adam. We sold StyleMob within nine months to an advertising network.
As a result of the acquisition, I took a job as a product manager at that ad network. Thus began what I now call the great inauthentic period of my life — when I could often be found in the parking lot crying at 5pm, wondering what I was doing wasting my life promoting a product I didn’t believe in.
I was in my mid-thirties, feeling the squeeze of expectations to find a husband in time to have a child, buy a home, and climb the career ladder. I didn’t like the male-dominated environment, or the version of myself I was becoming in it.
This period of burnout and disconnection is something I now see as important in my own journey to becoming a leadership coach. If you are suffering from burnout and disconnection, I would only recommend working with a coach who knows what it’s like to fall into those holes, and how to get out of them.
I know what it costs to stay in that place too long. And I know what it takes to find your way out.
My StyleMob co-founder and me
South America, Tango, and the Discovery of Embodied Leadership
Once again, travel helped me find the way. So did listening to my body.
When I got to my wit’s end in Silicon Valley, I packed up and spent a year traveling alone through Brazil, Colombia, and Argentina. That period of deliberate reconnection — with my body, my instincts, my joy — ultimately helped me realize that I wanted to take a new path in life, helping other women as a coach. That solo travel journey also put me on a path to deal with the effects of an incident of childhood sexual abuse, something I had always kept secret and never talked about before age 38, and to heal my heart enough to risk opening up in love again. All of this will be told in my forthcoming memoir, Wet.
And that’s the year when I discoered tango — and that also changed everything.
When I could feel what it meant to honor myself and stand up straight in tango, I couldn’t help but bring that wisdom into every other area of my life. Tango plays a starring role in Wet as the thing that rescued me from a lifetime of unhealthy patterns — in relationships, in work, in how I carried myself in the world.
I moved to Buenos Aires to nurture my love for tango, studying and eventually teaching my own brand of transformative tango through an immersive program called the Tango Adventure, which I ran with a wonderful team for six years. Hundreds of women came from around the world to study tango with us in Argentina.
Here’s a video where you can see me dancing during a recent trip to Buenos Aires. I no longer live in Argentina but I try to visit the mecca of tango every year.
Becoming a Coach — and Building a Practice Around Women’s Leadership
For 15+ years I have been working with clients one-on-one and in groups.
Over time, my practice has sharpened around the thing I care most about: helping women lead. I work with women founders, business owners, political leaders, and ambitious professionals who are ready to close the gap between how good they actually are and how fully they’re able to own it.
I also facilitate groups of women for CHIEF, the private membership network for executive women leaders — work I find deeply meaningful.
My approach is both practical and deep — cognitive, emotional, and somatic. I consider the work of self-leadership to be fundamental to our work on leadership.
Because leadership starts with you.
Now what?
You’ve just read my whole wild story. You want to know who your coach is.
If you’re wondering whether we’d be a good fit, the best thing to do is just get on the phone. Thirty minutes, no obligation. I’m a real person and I genuinely love these conversations.
Before you go…
Here’s a two-minute “sizzle reel” that walks you through some of my career and life highlights…from talking with Anderson Cooper to marrying myself in Argentina.