Although many are just taking real notice of Michelle Obama now with the release of her thoughtful and deeply authentic autobiography, Becoming, I’ve been a fangirl ever since she was introduced on the national scene during the 2008 presidential primaries as a working mom to two young daughters and wife to would-be President Barack Obama. Even without knowing her full story, I felt a kinship with Mrs. Obama who is not only a mom and a lawyer, but also a contemporary born the same year as me. Moreover, like me and some of my female peers a decade ago, Mrs. Obama was living the seamless life — functioning as a mom and a professional and a wife all at the same time.
But what I also didn’t know until reading Becoming is that even though Mrs. Obama made it all look easy when she was on the public stage, there were plenty of hard knocks and disappointments along the way. In sharing both her struggles and how she dealt with them, Mrs. Obama’s book offers a primer of a sort to the next generation of professional women in the law making their way. And with that, here’s what women lawyers can learn from Michelle Obama:
1. A Prestigious Well-Paying Job Won’t Necessarily Make You A Happy Lawyer
Michelle Obama started her career at Sidley Austin, a Biglaw firm in Chicago. She earned a big salary, bought a Saab, and paid down loans. Unfortunately, the work, while mildly interesting, wasn’t meaningful — yet Mrs. Obama felt that with all those benefits, she should be happy — plus, she didn’t want to disappoint her parents who’d devoted everything to her education. So she stayed as long as she could.
That’s the first lesson of Michelle Obama’s book that you never learn in law school: the jobs coveted by your classmates and portrayed as the brass ring by your professors simply may not be right for you.
- Finding People Who Share Your Values Can Make All the Difference
By her second year at Sidley, Mrs. Obama had started dating Barack Obama, whose career plans resembled hers only in that they both attended Harvard Law. While Mrs. Obama followed the conventional law student path, Barack Obama turned down Biglaw offers and didn’t apply for a Supreme Court clerkship for which he’d have been a shoe-in because he knew that he wanted to practice civil rights law and continue his community work. Meeting someone whose entire career was in Mrs. Obama’s words “one big swerve” emboldened her to take a swerve of her own, and look for a way out of Biglaw. That’s lesson two: surround yourself with people who share your ideas or are living their lives in a way you admire because it will give you the courage and inspiration to follow your heart.

Why Better Billing Statements Can Improve Your Firm’s Finances—And Your Client Relationships
Outdated billing is costing law firms money. Discover how clear, modern billing practices boost profits, trust, and cash flow in 2025.
- Identify and Play to Your Strengths
Before making a swerve, Mrs. Obama first had to decide whether she wanted to practice law at all. After some reflection, she realized that she didn’t — she’d simply chugged along to law school after college because it was something impressive to do. So instead of just moving on to another law firm, Mrs. Obama took the time to assess her strengths and concluded that she could shine in a job that worked with people on an individual level to help them overcome challenges or improve their communities.
Many lawyers who leave Biglaw simply jump to another firm or a government position, thinking that reduced hours or a less toxic environment will cure their longing for more. And sometimes it does — but in other cases, the real problem isn’t the job itself but a lack of desire to practice law.
- The First Step Isn’t Necessarily A Keeper, But Can Be A Start
In most of the blogs or talks on “finding life after Biglaw,” the subject leaves her law firm, and finds her dream job at legal aid or the Department of Justice — which is where the story ends. Mrs. Obama’s experience in leaving Biglaw was different and much more typical. First, simply because Mrs. Obama worked at Biglaw, it didn’t mean that a new job simply fell into her lap. Instead, finding another position was a job in itself, involving a lot of letter-writing and informational interviews that often didn’t pan out. Ultimately, Mrs. Obama wound up with a job offer at City Hall that didn’t seem all that exciting — lots of meetings and making site visits to view downed trees or address constituent concerns. Mrs. Obama’s parents weren’t fans of City Hall and Chicago’s notorious patronage system and apparently, even Barack wasn’t all that impressed when he learned that Mrs. Obama would be working for the Mayor Daley Machine.
But even though the job was far from perfect, it wasn’t a legal position and it wasn’t at Biglaw and therefore, an opportunity. And so Mrs. Obama leaped — partly because she was impressed by Susan Sher and Valerie Jarrett who had interviewed her for the position but also, I suspect because she simply could not spend another minute at Biglaw. As it turned out, the job probably didn’t make the best use of Mrs. Obama’s skills (my opinion, not hers) but the relationship that Mrs. Obama built with mentors like Sher and Jarrett — both working moms themselves — would prove life changing for both Mrs. Obama and her husband.
- Keep On Moving
I’ve noticed that many women stick to positions longer than men — feeling that leaving might be disloyal. Not so Mrs. Obama — when an opportunity to serve as an Executive Director of a non-profit called Public Allies came along, she leapt — even though it meant yet another job move and yet another pay cut, even from her modest salary at City Hall. As Mrs. Obama later recounted, the Public Allies job was her favorite because it that placed her in a leadership role and forced her to work beyond her limits.
- Part-Time Is A Ruse
As every so-called part-time Biglaw associate knows, part-time ain’t what it’s cracked up to be. Even as a part-timer, you’re still expected to handle all of your full-time responsibilities but in the span of a shorter week and at half the salary. Mrs. Obama experimented with a part-time position in a role at University of Chicago, but quickly wised up by her next job as Community Affairs Director at the University of Chicago Hospital where she insisted on a full-time position and a full-time salary with sufficient flexibility to enable her to make it home for her daughters.
- Work Life Balance Looks Like A Chipotle Bowl in the Car
Television shows portray work-life balance as effortless: a flawlessly made-up mom breezes out the door with kids in tow, spends lunch hour chit chatting with pals and returns home later to prepare supper and joke with everyone about their day instead of whining about the burnt meal. By contrast, Mrs. Obama gets real about what worklife balance looks like: a frantic lunch hour spent dashing through stores ticking off errands on the to-do list like picking up food for dinner or shopping for birthday gifts, then grabbing a Chipotle bowl and eating it in the car, grateful for 15 minutes of alone-time.
Mrs. Obama’s parking lot lunches illustrate another reason why parents — and mostly women — struggle to build a book of business at Biglaw. While single colleagues can devote their lunch hours to eating out with prospective clients, most women are spending lunch hour exactly like Mrs. Obama: dashing around town to complete errands and scarfing down takeout to make it back to the office in under 60 minutes.
- Never Settle for Second Place
As I wrote years ago, Mrs. Obama refused to settle for second place even though on the surface, her career didn’t seem as promising as that of her phenom husband who by then had been elected United States Senator. Even so, Mrs. Obama insisted that her husband pick up his socks and do his share of the housework.
Too often, I see women taking on the lion’s share of household work even while holding down a full-time job. This is an even more common expectation for women who own their own firms, since they’re presumed to be more flexible and also may earn less. Mrs. Obama showed by example that when both parents work, they need to share the load as evenly as possible.
- Sometimes, It’s Just Really Hard
Mrs. Obama doesn’t shy away from sharing the bumps that she and her husband faced during their marriage. The stress of infertility and sorrow of miscarriage. The petty little resentments and grievances that come up even for people who love and respect each other — and that sometimes can only be resolved with marriage counseling. Of course, in hindsight, it’s difficult to feel sorry for Mrs. Obama who eventually had two daughters and not only resolved her marital problems but renewed her commitment to daily 5 am workouts at the same time. Still, Mrs. Obama’s experience is a reminder that marriage can be hard and requires constant work by both partners — but that work can yield something even better in the end.
In law school, students learn how to think and reason in preparation for careers as lawyers. But law school doesn’t teach about life: how to deal with career dissatisfaction and find a way out, or the importance of surrounding yourself with people who have your back or about the unique challenges that women juggling career and family face. But these lessons are important because they can mean the difference between a mediocre career spent just phoning it and counting the days until retirement versus a life full of meaning and purpose. Which is why Michelle Obama’s Becoming should become required reading for women law students and lawyers — because the lessons she teaches can help all women lawyers become the best possible versions of themselves.
Carolyn Elefant has been blogging about solo and small firm practice at MyShingle.comsince 2002 and operated her firm, the Law Offices of Carolyn Elefant PLLC, even longer than that. She’s also authored a bunch of books on topics like starting a law practice, social media, and 21st century lawyer representation agreements (affiliate links). If you’re really that interested in learning more about Carolyn, just Google her. The Internet never lies, right? You can contact Carolyn by email at [email protected]or follow her on Twitter at @carolynelefant.