Alumni Q&A: Where Are They Now? Rachel Sher, Chicago Alumna

Rachel Sher (pictured, center) is the Director of Business Development for Chill Chicago. She spoke with Donielle McCutcheon (right) and Julie Snyder (left) about the benefits of meditation, her ongoing relationship with Sidley and the joys of not having an office with a door.

Julie Snyder: Rachel, why don’t we kick this off with what you did at Sidley and what you’ve been up to since?

Rachel Sher: I started at Sidley in 2007 in the IP Litigation group. I met some amazing people while I was there, many of whom remain some of my closest friends. Then I left in 2011 to go to a smaller litigation firm, but ultimately decided that becoming a partner at a firm was not the right fit for me professionally. I took a little time off and then went to a legal tech start-up, called PowerNotes, started by another ex-Big Law attorney. I worked with great people and learned a ton. After a few years there, I moved on to Chill, which I knew about because my cousin, Laura Sage, is the CEO and founder. She came to this after 20 years in finance so we had similar experiences, coming from corporate settings and doing a 180 of sorts into the wellness space. I joined Chill last summer to do corporate business development, helping companies to introduce some mindfulness and meditation to their employees.

Donielle McCutcheon: What trends are you seeing in the wellness space?

Rachel: I think, in Chicago, the corporate sector is beginning to understand that meditation and wellness are worth paying attention to. Increasingly, there is an awareness that wellness impacts attrition, training and bottom-line productivity.

Donielle: Any insights in particular about the legal industry and wellness?

Rachel: I think the legal community is paying more attention to, and devoting more resources to, its employees’ mental wellness. Chill actually offers a CLE-accredited course that fulfills the new mental wellness credit, and we’ve gotten great responses to that session. Now, arguably, the lawyers are showing up only because they need the credit and not because they think it’s going be beneficial, but the program really resonates with participants, and includes a guided meditation, which introduces participants to the actual practice.

We talk a lot about creating good habits early on in a profession that is, by definition, very stressful. Specifically, there's a focus on managing stress versus eliminating stress because it’s not realistic to think that stress will disappear. Instead, the objective is to learn and hone the tools that will help, so that when you’re in the midst of a trial or closing a deal, you are mentally and emotionally equipped to handle it.

Julie: How is Chill working with Sidley?

Rachel: I’m so excited to be working with Sidley; it feels so full circle. We’re holding our CLE session there in April, which is really exciting. I’ve also been talking to the folks responsible for New Associate Orientation and the Midlevel Associate Conference, as well as the summer associates program to see how Chill programming can be incorporated. Julie and I had an amazing time as summer associates, but I think there’s a focus now to enhance the programming beyond socializing and food and to incorporate some other wellness-focused activities.

Julie: How do you stay connected with Sidley, beyond your business relationship?

Rachel: I was just in San Francisco a week ago visiting one of my best friends, who I met when we summered together; now she’s in-house with Apple. Some of my closest relationships to this day are with people that I met at Sidley from 2006 onwards.

Julie: What’s a day in your life like? Do you still use your legal background?

Rachel: I think it’s impossible to not use the skills you’ve learned as an attorney in your day-to-day life. I spend at least two days a week in the studio to connect with the community here. We have members who come in regularly, and it’s nice to build those relationships on a personal level. I haven’t had an office with a door I can close in five years, which initially was a huge adjustment, but now it’s liberating.

Julie: What has been most gratifying for you in your current position?

Rachel: I have met some really interesting people and been introduced to a completely different community of professionals. At my last startup, most of us were attorneys who had left big law firms, so there was an inherent familiarity. Now I’m working with yoga teachers, meditation instructors and massage therapists, which is really fun.

Julie: What kind of advice would you give to people who are thinking of leaving private practice, or thinking of shifting out of the legal world?

Rachel: By definition, lawyers are risk averse, so I think those are hard decisions. When it comes to switching jobs or making a big career change, it was helpful for me, at least, to remind myself that nothing was permanent. I do think that a legal education and the experience of practicing as an attorney serves you in so many other professional fields. As a lawyer in a traditional practice, I wasn't really aware of that, until I stepped away from firm life.

Donielle: How has meditation impacted your own life?

Rachel: I am very much a novice meditator, but I can already see, in a tangible way, the impact of my practice. Meditation helps me in how I react to situations in my personal life, and in my business life; I find that it has made me a more patient person.

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UPDATE: Rachel is now General Counsel at Awesemo.com