The Rules I Broke to Belong

At Eleven Madison Park, I was required to straighten my hair. Not just make it look presentable—which I understood, particularly for someone who prefers the wild, just-emerged-from-the-ocean look—but straighten it. Because apparently, to achieve perfection, there had to be some level of uniformity. There were also sock and nail polish requirements, but I'll save those for another time.

One morning, as I was getting ready for work, I noticed a single curl that had arranged itself into a perfect spiral. A Shirley Temple curl. The kind that reminded me of drinking that overly sweet, effervescent cocktail with my Opa, or watching Little Orphan Annie with her magnificent head of red ringlets.

To say it was perfect would be an understatement. To straighten it, a blasphemy.

So I did what any curly-haired girl in my position would do: I straightened the rest of my hair and left that one curl intact.

When I arrived at work, the head sommelier noticed immediately and told me to put it away. Put it away. As though I had smuggled a small animal into the dining room.

I remember feeling embarrassed, indignant, and disappointed that something I found so beautiful had been treated like a violation.

It was a tiny act of rebellion. And, as I have recently come to understand, part of a much larger pattern.

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I was not a particularly rebellious child. I followed the rules, especially when they came from people I admired. Teachers, parents, authority figures who seemed to know something about the world that I didn't. And for a long time, this arrangement worked beautifully. I did what was expected of me, earned approval,played some sports, volunteered, got into college, things generally worked out, you know.

But as I got older, I began encountering rules that didn't make sense to me. Rules that seemed arbitrary, protected institutional traditions, or required sacrifices I wasn't sure I wanted to make.

And I developed a rather convenient workaround–that is, I would just do what I thought was right and hope nobody noticed. Actually… right might be too generous. More accurately, I would do what benefited me, what made sense to me, and hoped nobody noticed.

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I've spent much of my professional life working within institutions I genuinely adored. Eleven Madison Park, with its relentless pursuit of excellence. Later, higher education, with its intellectual energy, wonderful colleagues, and students trying to figure out what they wanted from their lives.

And I thrived in those environments. Truly, I did. The shared sense of purpose. The camaraderie. The high-octane printers. The health insurance. The reassuring knowledge that somebody else was responsible for keeping the lights on.

I loved being nestled. There's a reason Dartmouth held such a special place in my heart!

There's a popular entrepreneurial narrative about the restless independent thinker who grows tired of bureaucracy, throws off the shackles of corporate life, and boldly strikes out on her own. HUZZAH!

Alas, that is not my story. I didn't want to leave NYU Stern, where I had launched Circle, a group coaching program that grew out of my graduate research and became one of the most meaningful professional projects of my life. I loved facilitating it, watching students connect, and seeing what became possible when people were given space to reflect together.

I wanted the school to embrace it as enthusiastically as I did. But as I tried to expand the program, I encountered resistance. And because the work had become so intertwined with my identity, I struggled to separate the rejection of an idea from the rejection of me.

Rather than accept Stern’s boundaries or make a clean decision to pursue the work independently, I tried to preserve both possibilities. I made choices I regret, damaged relationships I valued, and ultimately found myself unable to remain in a place I had desperately wanted to stay.

For a long time, I understood that experience as professional disappointment.

Recently, a therapist helped me recognize something else: In trying to avoid a loss, I ultimately helped bring it about.

The common denominator wasn't rebellion. It was avoidance. I wanted the freedom to make my own decisions and the security of remaining in good standing with people whose approval mattered to me. I wanted to disagree without disappointing anyone. And when those desires came into conflict, I sometimes chose concealment over confrontation.

Of course, disagreeing with a rule doesn't entitle us to disregard it. And discomfort with authority doesn't absolve us of responsibility for our choices. But in my case, I was avoiding conflict to preserve relationships. I'm keeping the peace, I told myself. Being pragmatic. Picking my battles. (Isn't that what everyone tells us to do? Pick your battles!) Meanwhile, I was compromising my integrity in the name of protecting something I loved. And ultimately, the conflict I was trying so hard to avoid may have been considerably less destructive than the consequences of avoiding it.

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I've now been an entrepreneur for two years, and there is so much rejection. OMG, so much.

Potential clients decide not to work with me. Organizations pass on proposals. Programs I believe in don't always attract the interest I hoped they would.

I've also recently returned to tennis, where you miss shots constantly. Sometimes you do everything right and still lose the point. Sometimes you make an error so spectacularly unnecessary that you wonder whether you've ever held a racket before.

And then you play the next point.

Entrepreneurship has required a similar relationship with rejection. (I wonder if I can write off my tennis lessons as a business expense.) But I've come to realize that what made my earlier institutional experiences so difficult wasn't simply rejection. It was powerlessness.

When an institution declined to support an idea I came up with, something I loved and believed in, I experienced that decision as the end of the road. Someone else's permission determined whether I could move forward. Today, a prospective client can decline to work with me, and I can still believe in what I'm offering. I can revise it, reconsider my approach, or offer it to someone else.

Rejection no longer necessarily means stopping. It means adjusting my aim.

And I wonder how many of us are negotiating some version of this tension.

Maybe you love your organization but increasingly disagree with its priorities. Maybe the career you worked so hard to build no longer fits the person you've become. Maybe you're making accommodations, withholding opinions, or bending rules because the possibility of losing what you've built feels unbearable.

And maybe you're not ready to leave. Maybe you don't even want to.

We celebrate people who make bold exits. Who quit their jobs, launch companies, change careers, and finally decide to do things their own way.

But what about the people who want to stay?

Maybe the question isn't Should I stay or should I go? Maybe it's: What am I so afraid of losing that I'm unwilling to be honest about what I want?

Because sometimes the rules won't change. Sometimes our ambitions and existing commitments are genuinely incompatible. Sometimes we have to choose.

I still think about that perfect curl.

At the time, I thought the question was whether I should have straightened it.

Now I wonder why I couldn't simply say, I know what the rule is. I don't agree with it.

And be willing to hear the answer.