Throughout my 20s I was an outsider, a nomad, a wanderer of the network and rebel against the institutions. I was more inspired by what made me angry than what I could do to make a difference. I had ideas for how the media should change, how philanthropy should reform, how governance should open up, how the powerful should always be held to account. “Power is inherently conservative,” Pia mentioned as we discussed our various mutual friends who have entered government over the past few years. “Power wants to be in power.” As a 20-something, all I wanted to do was fight back against power. So much anger, so much writing, so little self-sacrifice.

By the time I turned 30, by the time I had penned over a 1,000 blog posts and spoken at over a hundred conferences, it became readily apparent that I could go on criticizing the institutions that are built around power — government agencies, media corporations, private foundations — without ever influencing them. In order to contribute to the change I sought, I needed to develop a relationship with powerful institutions. Like so many of my friends that have entered Latin American governments over the past five years, I sought power in order to confront power.

The long moral arc of the institution bends toward conformity. A wide range of explicit and implicit incentives reward compliance and discourage the kind of dissenting, unconventional unorthodoxy that is the flame of critical thinking.

There’s an additional challenge if you work in philanthropy — one that is perhaps best described in “The Gathering,” a satire about the life of a grantmaker that was published in The Chronicle of Philanthropy by “a prominent philanthropy leader” who wished to remain nameless. The life of a program officer often borders on undeserved opulence — free meals, business class flights, unsolicited flattery and little accountability. Sure, you could be the subject of criticism, but only when your back is turned. To work in philanthropy and stay true to one’s aspirational self requires nearly inhuman self-regulation. Those who possess such a strong moral compass tend not to last long.

The idealist-non-conformist is destined to be discontent in the institution. Either the self-conscience rears its head with a disappointed frown, or one cuts against the conforming grain of incentives and recognition. David Brooks has a more optimistic take. Truly creative people, he argues, “embrace dialectics and dualism.”

They cultivate what Roger Martin called the opposable mind — the ability to hold two opposing ideas at the same time. If they are religious, they seek to live among the secular. If they are intellectual, they go off into the hurly-burly of business and politics. Creative people often want to be strangers in a strange land. They want to live in dissimilar environments to maximize the creative tensions between different parts of themselves.

We live in a period of disillusion and distrust of institutions. This has created two reactions. Some monads withdraw back into the purity of their own subcultures. But others push themselves into the rotting institutions they want to reinvent. If you are looking for people who are going to be creative in the current climate, I’d look for people who are disillusioned with politics even as they go into it; who are disenchanted with contemporary worship, even as they join the church; who are disgusted by finance even as they work in finance. These people believe in the goals of their systems but detest how they function. They contain the anxious contradictions between disillusionment and hope.

How do we embrace dualism, inspire creativity and reinvent institutions while diminishing the evil beast of anxiety? One lesson I’ve learned while working within institutions is that tone is everything. Cheerfulness and collaboration can move mountains. In hindsight, I see that my failures in nudging past employers toward greater transparency mostly resulted from not investing enough time in developing personal relationships with the gatekeepers.

I am posting these reflections in public as a way to nudge myself to stay true to who I am, or at least who I want to be. I’d also love to hear the reflections of fellow journey(wo)men who struggle to resist conformity while working from within. I know that I need to encounter the inspiration of others to serve as a reminder for myself. Panthea Lee and Zack Brisson, the co-founders of Reboot, are two kindred spirits in this journey. Panthea’s reflection on what Reboot has learned in its first three and a half years has become something of a road map for how I hope to live my own professional life.

I was also recently inspired by a deceivingly simple documentary, The Lottery of Birth (Available on Hulu. Torrent file here). Through a collage of conversations with smart thinkers, the film reminds us that circumstance dictates most of the values and assumptions we hold. The vast majority of our personality and identity is defined by the lottery of birth. But the lottery of birth doesn’t imply futile passivity. The scene from the film that stayed with me is of a man from Stanley Milgram’s famous “obedience study” who refused to obey the authority figure in the room.

Half the subjects in Milgram’s study obeyed the white-coated authority figures who told them to administer dangerous — even lethal — shocks to unseen people in an adjacent room. This man refused:

Lab coat: It is essential that you continue the experiment.

Research subject: No, it isn’t essential. Not one bit.

Lab coat: You’ve got no other choice, teacher.

Research subject: Oh, I have a lot of choices. My number one choice is that I wouldn’t go on if I thought he was being harmed.

Indeed, we have a lot of choices.