The Summer We Started
In the summer of 1997, I was a second-year law student working as a summer associate at a large law firm in South Florida. Across the office from me sat a first-year law student who was not supposed to be there.
If you have been reading this series, you have met him before. He was the office-mate in Not in on the Secret, the one who received the same “no” I did (but decided to ask again).
The firm had a policy: no first-year associates. He had been told this. He applied anyway, made his case, and got the seat. I had been told the same thing the year before. I dutifully filed it away and came back as a 2L when the timing was right.
We spent that summer in the same office, doing the same work, and (kind of) starting from the same place. He is now one of my closest friends. And the story of where we each went from that summer is the reason I think about audacity differently than most people who write about it.
Two Very Different Roads
From that shared starting point in 1997, our careers moved in very different directions.
His path was expansive. After law school he clerked for a federal judge in the Southern District of Florida, then joined a firm different from the one at which we both summered. From there he went to the United States Attorney’s Office for the Southern District of Florida, where he prosecuted federal cases. He then moved to Washington to work as an advisor to the Deputy Attorney General at the Department of Justice. He eventually came back to Florida, worked at yet another firm, and finally returned to the firm where we had both started. He made partner there in October 2008.
My path stayed in one place. I joined the firm after graduating from Harvard Law in 1998 and stayed for the next two decades. I was informed that I had made partner in the first week of December 2008, approximately three months after the birth of my son, and two months after my good friend.
In those same eleven years, we both got married. He and his wife had two children. My husband and I had three. I want to establish all of that now, because it matters to everything that comes after.
His resume is objectively richer: a federal clerkship, the USAO, the DOJ, multiple practice environments, a depth and breadth of experience that my linear path did not accumulate. I say that plainly, not as a concession, but because honest accounting matters for the argument I am making.
What the Comparison Actually Shows
It would be easy to read this as a story about audacity. He was bolder. He moved when I stayed. He took the risks I did not take.
That reading is partially right and mostly incomplete.
Here is what was also true during those eleven years.
He had a wife.
I was a wife.
His wife made a deliberate professional choice to work in academia, in part because it offered a more predictable and homebound schedule, fewer hours, and breaks that were more consistent with their children’s school schedule than his careers in BigLaw, government, and private practice could provide. Their household was structured in a way that gave his career significant geographic and professional mobility.
I was also billing hours and building a practice while bearing children and carrying much of the responsibility for creating the day-to-day stability I wanted for my family. The career moves available to him, including the USAO, the DOJ in Washington, and the lateral jumps, required a kind of geographic and professional mobility that came at a different price for me. Not because I lacked the ambition or the ability, but because I was also the person responsible for holding down much of what would have had to move, bend, or be rebuilt around those choices.
There were other differences too. He is a Hispanic man who is generally perceived as white. I am a Black woman. I am not going to pretend race and gender made no difference in how we were perceived, sponsored, or given access to opportunities. They did. But they are not the whole explanation either, and making them the whole explanation would let the structural analysis do work that the personal accounting also needs to do.
The Choice Inside the Constraint
Here is where the argument gets more complicated, and where I think most writing about audacity goes wrong.
The path that was available to him was not simply unavailable to all women. There are women who have built careers exactly like his, moving through government, lateraling between firms, accumulating breadth while managing families. Some had different support structures. Some made different choices about what they were willing to trade.
And here is the part that matters: I would not have taken his path even if it had been equally available to me. That is not rationalization. It is honest.
I knew the kind of mother I wanted to be, the kind of family I wanted to have, and what I needed in my personal life to feel like a whole person rather than a depleted one. Those were real values, and they shaped real choices. The fact that I would not have chosen his path does not make the structural differences between us irrelevant. Choices are made inside conditions, not outside them. My values pulled me toward stability, and I was operating in an institution where preserving that stability narrowed the range of career moves available to me and changed the professional price attached to the choices I made.
I stayed in one place, built deep expertise, raised three children, and made partner on a timeline that worked within the life I had decided to live. I am not willing to pretend those choices were made on a level playing field, or that the trade-offs were identical for each of us. They were not. The structural constraints were real, and the personal choices were also real. Both things can be true simultaneously, and the work is holding them both clearly without collapsing one into the other.
But here is what gets left out of most versions of this conversation: my staying was also audacious.
Deciding that I was going to have three children, a present marriage, and what I considered a full life inside an institution that implicitly rewards people who travel lighter was its own kind of bold move. BigLaw does not tell you that you cannot have that life. It simply communicates, through a thousand small signals, that the people who want partnership tend not to insist on it.
Sometimes the signal was not even subtle. I was asked during those years whether I was “on the partner track or the mommy track.” The question assumed the two were mutually exclusive. My answer, lived over eleven years, was that the person asking clearly had a very small map.
Making partner did not retroactively make every choice I made correct, and another woman could have made equally thoughtful choices and received a different outcome. The audacity was not in being rewarded for the choice. It was in insisting that I was allowed to want both before I knew how the institution would answer.
I insisted on both. That is audacity too, just pointed in a different direction, toward a different thing the institution seemed to be saying I should not want.
Our stories are not a comparison between someone who was brave and someone who was cautious. They are a comparison between two people who wanted different things, made different bets, and ultimately arrived at the same professional destination by roads that cost differently.
What "Audacity" Actually Costs
The motivational version of audacity is clean and appealing: be bolder, take the risk, go anyway. It is not wrong. It is incomplete.
What that version leaves out is that the same bold move is not priced the same for everyone who makes it. The cost of audacity, what you spend, what you risk, and what you need underneath you to absorb the outcome if it does not pay off immediately, varies significantly depending on who you are and what you are also carrying.
His household could absorb a USAO job, a move to Washington, and multiple professional transitions because it had been structured in part to create that flexibility. An equivalent move for me would have required dismantling or substantially changing something I had deliberately built. That is not a grievance. It is arithmetic.
Constraints change the price of a choice. They do not eliminate the existence of choice.
The implication is not that audacity is a trap or that bold moves are not worth making. It is that before you make the move, you should know what you are actually spending. Know what the infrastructure underneath you looks like, what you are trading, and what you are not willing to trade. Make the decision with clear eyes about the full cost, not the sanitized version.
And then make peace with the trade-offs attached to the choices you made. Not because the playing field was level, because it probably was not, and not because you chose every cost that came with the decision, because you probably did not. But resentment over a consciously chosen path can become one of the most expensive things you carry in a career, and it spends energy you need for something else.
A costly choice is not necessarily the wrong choice.
That is ultimately why I tell this story. The fact that my friend and I arrived at the same professional destination does not mean the journeys were equivalent, and the fact that I chose a narrower path does not mean I lacked audacity. You can stay and build. You can take the longer, wider road. You can make either choice for reasons that have nothing to do with fear.
The question is not which path is bolder. The question is which path is yours, what it actually costs, and whether you are making the choice deliberately or having it made for you by assumptions you have not examined.
Sometimes audacity is taking the bigger swing. Sometimes it is deciding, deliberately, that the life or career you want is worth choosing even when the institution has made that choice harder or less rewarded.
Audacity is real, and it can be built. It is also not priced the same for everyone who builds it. The point is not to find the path with the lowest cost. It is to understand what your choice actually requires, decide whether the trade is worth making, and then resist treating the fact that it cost you something as proof that you chose wrong.
Strategic Radical Acceptance™. This is not Resignation. This is Liberation. And it’s Strategy.
