Art: Charter

Around the time last year I dropped off my daughter for her first year of college—quite ceremoniously with many farewell dinners, emotional Facebook updates, dorm tchotchkes stuffed into enormous IKEA bags—actor Brooke Shields posted herself sobbing through the same ritual.

Except in this case, her child was starting sophomore year. Wait, this will happen again? I filled with dread as I watched the viral video, having naively believed I was done with goodbye.

We’re in the season once again of the Big Dropoff. You’ve possibly seen photo evidence of parents hugging kids and fairy lights strung over concrete masonry walls and advertisements for extra-long sheets and shower caddies. Less focus, though, is given to the arguably even bigger moments that come after this one. Parents play a vital, increasingly important role in preparing their offspring for the new, changing world of work. What no one tells you is how much launching (that’s the lingo for this process) is equal parts redefinition of both parent and child.

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Thankfully, Shields foreshadowed this. Bad news, it doesn’t get easier. Good news, they still need us, profoundly. Here are some other lessons I’ve learned, one year in:

A new me, a new you.

I’ve written before about the epiphany that college dropoff represents for working mothers like me. From my Mother’s Day column this year: As “my house and heart were suddenly empty, I realized how fleeting everything is. ‘It goes quick,’ people tell you when you have a baby. I thought they were referring to growth charts and milestones like walking and reading, pimples and prom. Now I realize they were referring to my role in my child’s life.”

We talk incessantly about missing our kids when they leave but we should also acknowledge that we might miss who we once were—and the struggle to reimagine who we are now. For those who have just begun their launch, these next few months will be filled with a ruthless prioritization of what matters and defines you. Inevitably, that will affect the work you care about, and the time you have to devote to it. If you’re like me, with more children still in the house, suddenly there’s another clock ticking before they, too, might leave. If you don’t, there might be newfound time and interest in new creative pursuits.

Bottom line: I was a different manager as a working mother with two school-age kids than the one I am now. Besides the time factor, one big way is how I approach the process of hiring, training, and envisioning job paths. With my child at the start of professional discovery and me in the role of CEO, we essentially represent the bookends of careers. I believed I was a thoughtful leader when it comes to the needs of those in the middle. I realize now that I looked at such workers through the lens of how I made my way—beginning in an outdated, irrelevant, bygone era that didn’t have the ubiquity of mobile phones, social media, and artificial intelligence. Now I think about career ladders with (admittedly terrifying) foresight versus the nostalgia-clouded glasses of hindsight. The reality check is welcome.

Reading/watching/engaging online is not doing.

In my journey as an entrepreneur, the idea of ‘failing fast’ is a bit of a refrain. Yet in the world of college preparation, admissions, and dropoff, families seek answers over experience. I’m in several social-media groups and email lists for parents of older children (the so-called ‘grown and flown’) and this tone is worrisome.

To the extent that we can let our kids inhabit the same philosophies we employ at work—to fail, experience, do—the better. I sometimes call people in their late teens and early twenties “Generation Know Everything” because they have been aware and exposed their entire lives. I dub my parents and their fellow Baby Boomers “Generation Patience” because they seem comfortable waiting in long lines, knowing imperfection awaits at every turn, and somehow still keeping the faith.

We should encourage as much independent “doing” beyond the college classroom as possible, from the hell of filling out financial-aid forms to booking movers to understanding the fine print in a rental agreement. The transition from protecting our kids to letting them figure it out is also necessary, albeit painful. Confession: I have cried more during these mundane moments of pain that my kids must go through than I did on the day of college dropoff. That’s something else nobody told me; you prepare for the actual moment of parting but it’s actually much more protracted than that. If we’re lucky.

There are still important lessons to teach, namely communication.

In the days after they flee the nest, we stalk college orientation Instagram pages and check our phones for missed calls or texts. The balance of offering space and availability is tough but necessary. In our quest for constant communications with our loved ones, though, we might be missing a greater lesson we need to impart: how they should communicate with others.

As a manager, this is where I see the greatest rifts among generations. As a mother, this is where I see an ability to coach and model better behavior. How to structure an email letting a professor know you are sick? How to apply for internships when no application exists? How much personal information is too much to share on social media? How much is just enough for a job interview? We’re in constantly shifting personal and professional landscapes, and there are different norms across different workplaces.

High schools and colleges—even, perhaps especially, the most elite ones—do not train students on these vital life skills. I once pledged to not help “place” my kids in jobs or internships with friends or my network and am still committed to the idea. But I underestimated the lack of preparedness of many kids—including mine—to engage with the world professionally. That’s partly because their interactions have been largely remote for the past few years and partly because AP English classes usually don’t teach how to write cover letters.

Coaching my daughter on how to craft professional emails, for example, seemed a worthy investment. Mistakes were made, I made some suggestions, then I bit my tongue. Eventually, I stopped being needed on this front.

College is a most privileged place.

The recent US Supreme Court ruling on affirmative action should make us resolve to double down on infusing our college-going kids with a sense of social justice. The ban on race-conscious university admissions means college essays and extracurricular activities will play a bigger role in who gets in; these portions of the application tend to favor wealthier students, teens with access to such offerings or counselors who know how to package them.

Similar to the focus on anti-racism tools after the murder of George Floyd, we must have conversations about shedding our own privilege or bursting the bubble that college represents.

My version of addressing this was leveling with my daughter on why my credit card was only for emergencies and why her weekly allowance was paltry compared to her peers: “I cannot teach you struggle,” I said. “The only way you will learn is to actually struggle.” This position is not intuitive for parents—it is actually the opposite of what we are biologically wired to do—and yet this is the time to begin reassessment.

Even such a conversation (and the reality of a safety net) reeks of privilege. Yet I fear the makeup of college campuses to come and the ensuing workforces we will create that don’t know the value of diversity, the crisis of income equality, the meaning of struggle.

I’ve now supervised others for more of my career than not, and I see acute differences in colleagues who have had to hustle or innovate their way to success versus those whose parents paved the way. For the benefit of their child, and their child’s future employer, parents might try to get out of the way more often.

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