The Midlife Chrysalis

My class of 2006 graduated ambitious as all hell, ready to break glass ceilings and find happiness, purpose, and a paycheck. Immediately.

But in the 20 years since, we’ve experienced life’s bruises—losses, layoffs, breakups, fertility struggles, and mental health challenges. Some of us are more tired than we were at Wellesley, some have careers that bring us more joy and fulfillment than we could have imagined, and others are struggling with one of the toughest job markets in decades. Many of us are rethinking what matters most to us. Rather than a traditional midlife crisis, some refer to it as a “midlife chrysalis.”

I’ll be the last to say I am aligned with my goals. I’m frequently walking down a busy Brooklyn, N.Y., sidewalk between my toddler, chasing a pigeon in the wrong direction, and my son, speed scootering the other way. More than I’d care to admit, I’m looking down at my phone, answering an urgent work text, hoping that nobody collides with anything or anyone. My life is figuratively overflowing with my job and children, and it is literally overflowing with never-ending piles of laundry.

I’m not brave enough for a full midlife heave-ho just yet, but I am slowly trying to claw pieces of my life back. So far, it’s small moments like taking a longer walk in the morning before work, watching ER reruns with my wife, and being more present with my kids. I’m also trying to be more grateful for the chaos of my life.

My classmate Farah Hussain ’06 found herself exhausted from her corporate job at PayPal. During a three-week leave she did a leadership coaching session, something she’d picked up on the side, and realized that time seemed to melt away. She started plotting her way out of her job and grew her own business.

Maybe she should have been scared, but she says she wasn’t, because her decision was grounded in vision and purpose. She was so ready, she didn’t care what anyone thought. “Anyone,” she says. She’s now happy as an executive coach and painter. She encourages her clients to ask themselves, “Am I operating from a place of fear and anxiety or vision and purpose?”

Kate Broad ’06 started out writing romance novels under a pen name. She recently released her debut novel, Greenwich, under her own name. Her midlife shift, she says, was finally developing the writing voice she always wanted. When she graduated, she, like many of us, assumed her career would be a linear, upward trajectory. “The actual reality is that there are so many bumps on the way,” she says. People now see her successful book launch and nationwide tour. What they don’t see are the three books she attempted to sell before Greenwich. She recently won an award for one of those unpublished manuscripts.

For Dana Weekes ’03, burnout came as a top DC lawyer. The daughter of immigrants, she was raised with a work ethic of steel and says her bonus one year was more than her father’s entire salary. But chasing that path into her 30s took a severe toll on her mental health. She says she was so deep in survival mode that finding the courage to walk away was her only choice.

Weekes now hosts a podcast called “The Rest of Us.” Rest isn’t just about sleeping more, she says, but a whole new “liberating form of self-acceptance where you consciously navigate the world in your agency and belonging.” In other words, she’s teaching us how to climb our own mountains, not everyone else’s. After she helps people think deeply about how they can step into their own agency, she leaves them with one question: Am I willing to change?

The happiest among our class may well be the senior executives. I hope for them that’s the case. But I suspect the most fulfilled may be the lucky few who have learned to climb their own mountains, whatever path it takes.