My Next Chapter

Ann O'Leary
7 min readMar 22, 2021

Sit for a moment. Take a deep breath.

These are not things people who work in politics, policy, or the law often do. Or at least they’re certainly not things I do often or well. We are the ones who are leading crisis after crisis, demanding action and accountability, making good on our promises, focusing on what is next on the horizon or how we can do better. And for me, it has meant rushing and rushing … driving too fast on I-80 from Oakland to Sacramento — racing to the State Capitol or the Governor’s Office of Emergency Services — or racing back to my children in Oakland, always late, always on the phone for just one more call. In years past, it was the red eye to D.C. and to the Hillary campaign headquarters in Brooklyn. I started feeling like superwoman — changing from my sweatpants into my business suit in the stalls at La Guardia or in Penn Station or Union Station — from my mom-wear to my business-wear. And I loved it.

The call to public service is strong. The issues of the day are so profound, and the ability to do good in government could not be more pressing. But in January when I stepped down from my job as Chief of Staff to the Governor of California, I was given the gift of slowing down and thinking about what I wanted to do next. How would I choose to live my life, doing the work I love, continuing to positively impact the biggest issues of our day, and be present for my children?

Today, I’m happy to share where I have landed. First, I am joining Jenner & Block as a law partner in their new San Francisco office. I’ll be Co-Chairing the firm’s Government Controversies and Public Policy Litigation Practice with the Chair of the firm and the founder of this practice area, Tom Perrelli. I want to practice law at a firm that helps private-sector clients facing matters that have major implications for their businesses, as well as for public policy and our society. Under Tom’s leadership, the attorneys at Jenner & Block have a stellar reputation for helping private-sector clients facing legal issues that intersect with government regulation and oversight, and that require a mix of litigation, regulatory, communications, and internal investigations. I also want to practice at a firm that deeply values pro-bono work and improving diversity in the legal profession. Jenner & Block more than meets these criteria. The firm continually ranks #1 in its commitment to pro-bono legal services among the top law firms in the country. And the firm has acted with intentionality about how to increase diversity and inclusion in its own ranks, while being at the forefront of civil rights litigation that expands opportunity and inclusion in our society.

In addition to practicing law, I will be doing the two other things that have been drivers in my life: mentoring and teaching the next generation of public-minded lawyers, and continuing my lifelong work of advocating for a “care economy” that allows men and women to fully participate in work while being able to take paid time off to care for the ones they love. We must create an economy that includes an infrastructure that makes quality child care and elder care available, affordable, and accessible, and does so while ensuring that paid caregivers are treated with dignity and paid a living wage. To that end, I am happy to be teaching a course at Stanford Law School on “The Law and Policy of America’s Safety Net: Examined through the Great Stress Test of COVID-19,” and to be affiliating as a non-resident Senior Fellow with The Century Foundation, joining their team of experts working on these issues.

While this may not sound like a deep breath and a relaxing life, for me it means that I get to do work I love at three of the most respected institutions while also staying in the San Francisco Bay Area. When I stopped working in January, I became acutely aware that my children — like so many children across the globe — need more support. The social isolation and disruption to their lives have been profound. Both their Dad and I know that there is a season for the work we do in public service, but that being available to our kids during this difficult time is our priority.

You may be wondering what happened to all those rumors that I was hoping for a job in the Biden Administration. While it is true that public service is in my veins and I would love to serve my country again at the federal level, where I have landed is exactly where I should be right now. I have deep personal and professional respect for President Biden, Vice President Harris and White House Chief of Staff Ron Klain who have built a Cabinet and a Senior White House team that is incredibly diverse and is filled with people who have strong expertise in federal government service to tackle the extraordinary challenges our country is facing. I sleep easier knowing they are there making the critical decisions that will save lives, put our economy back on track, address the deep racial inequities in our country, and take bold measures to address climate change.

I also am reflective and aware that having the choices I have to work at the highest levels of my profession are rare privileges for anyone, and certainly never opportunities I even dreamed of when I was young.

I grew up in a small town in Maine in a middle-class household with two parents who had been the first in their families to go to college.[1]Our home was heated by woodstoves and our household was filled with love, laughter and always a bit of chaos. My parents committed much of their lives to helping those who had less. My Dad was a labor union leader and my Mom stayed at home, then ran her own antiques business and ultimately went back to school to become a social worker. My sister struggled from her earliest days through her childhood and adolescence with what we now know was undiagnosed, untreated mental health challenges, and ultimately dropped out of high school to become a teen mother two times over. One day in the early lives of my sister’s children, she realized she just could not parent. From that day on, my parents became the parents of their then 4-year-old and 6-month-old grandchildren, raising them for the entirety of their childhood.

I was the lucky one. I did well in school, and when my high school English teacher encouraged me to apply to Mount Holyoke College, my parents didn’t discourage me despite the high cost of tuition. When the financial package I received didn’t cover the cost, they went to the bank and took out a second mortgage on their home. At the time, I didn’t appreciate how that act would forever, fundamentally change my life.

From high school through college, I did all I could to financially contribute to my share of college. I worked afterschool and on weekends at Burger King from the time I was 15 years old all through high school (ultimately getting recognized as one of the fastest and most courteous drive-through workers in Bangor, Maine!). I went to Bar Harbor in the summers to make money off the tourists by working as a chambermaid in the rental cottages and making minimum wage of $3.45/hour selling T-shirts. When I got to college, I worked as a Federal Work Study student washing dishes, serving food, and working as a secretary for as many hours as I could while maintaining my studies and running on the cross-country team.

By the time I graduated from college, my parents were fully parenting their grandchildren and stressed out financially and emotionally. I had gotten the bug of public service from them and was inspired by the election of President Bill Clinton and Vice President Al Gore (and by the First Lady Hillary Rodham Clinton) with their fight to pass the Family and Medical Leave Act and their commitment to try to pass universal health care, so I headed to DC. Unlike other recent college graduates flocking to DC at that time, I couldn’t afford to take an unpaid full-time internship in the Clinton White House. Instead, I agreed to volunteer at the White House before I went to my paying job. I got up at 3:30 a.m. to be at the White House at 4 a.m. to do the “news clippings” (it was before the days of the internet) and to deliver the news packet to the President and his senior staff before 7 a.m. After a year of volunteering, I got a call asking if I’d be interested in applying to be an administrative assistant to one of the President’s senior advisors. I interviewed the next morning and that same day, I got a job offer — one year out of college — to work in the White House as the most junior of aides, in a position that was technically a slot for a professional secretary with an annual salary higher than most junior aides -$40,000/year — which was more money than my parents had ever made in their combined income in one year. When I called my Dad to tell him the news, he paused so long that I thought he was disappointed, until I realized he was choking back tears. That second mortgage had been worth the investment.

It is this background that keeps me humbled, grounded, and motivated. And it keeps me committed to continually trying to improve the social safety net in America, call out our need for real mental health care, and open doors of opportunity and inclusion for others.

The fight, the grit, the very early training in crisis management, the work ethics and the habits I formed along the way have allowed me to serve at the highest levels, and for that I am grateful.

Today, I sit for one more moment, take a deep breath, and truly look forward to jumping into my next chapter.

[1] My Mom was the first woman in her family to go to college, following in the footsteps of her Dad who had been the first to go, after she helped overcome her mother’s skepticism about spending money to send a girl to college.

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Ann O'Leary

Fighter for kids & families with @HillaryClinton; co-founder of soon-to-launch Opportunity Institute; lawyer, policy wonk, wife, mom, & avid outdoor runner.