During their almost-teen and teenage years, your kids are going to have to deal with changing bodies, hormone levels, and moods; friendship issues, including peer pressure of various kinds; competition in the classroom, on the sports field, and elsewhere; social media; learning to drive; exposure to drinking, smoking, drugs, and sex; academic stress; high-stakes standardized testing; the college or university application process; and the necessity of starting to chart their own independent life course and direction, including separation from you, as they mature and get ready for adulthood. That’s a lot for them to handle—and parentally speaking it would be a lot for you, too, even if you weren’t working. But you are, and your career is also likely reaching its crescendo: your responsibility and earnings levels are at or near their peak, the professional and financial stakes may be higher than ever, and it’s very possible that you have even less time for the kids than you did when they were small.

Having been a working parent now for a decade-plus, you needn’t do a wholesale self-reinvention. Yet in order to keep workparenting as effectively, authentically, and confidently as possible throughout this phase, what you do need are straightforward, honest answers to your most pressing questions. So that’s precisely what we’ll do in this chapter: look at each of those big, nagging concerns in turn—and at twenty-one specific ways for you to allay them.

Since my kid entered the teenage years, I feel as if we’re constantly in opposition—and given how little time we have together, it’s killing me. How can I keep the tone of our relationship more positive?

  1.  Beware the Great Inversion!  When you first became a working mother or father, one of your greatest challenges was figuring out how to be, and talk about, your “parenting self” at work. Now, you’ve likely got the reverse problem: you may be bringing home way too much of your professional skills and self. Think back on the past year or so, and ask yourself if you have:

• Treated family dinner like a workplace report-out
• Given the kids performance-review-style feedback on their academic results
• Provided here’s-how-you-do-it style directives on their friendships and social concerns
• Used words like manage or efficient when discussing weekend plans
• Ever spoken to the kids the same way you might talk to underperforming employees

If you have, then you’re caught in this common trap. There’s nothing wrong with your workplace habits and skills; they’ve served you very well over time. But applied in the context of a parent-child relationship, and during this particularly sensitive, high-change, high-emotions period, they’re going to create friction. If you can resist the temptation to keep your work hat on at home, or can think of yourself as being a mentor to your teen in addition to a leader or boss, a lot of that adversarial tension will begin to dissolve.

How can I keep my kids safe when I’m hard at work all day, and not around to play police officer?

  2.  Make safety a constant drumbeat.  If you’re incessantly nagging your teenager to clean up her room, practice the clarinet, and only wear unripped T-shirts, among dozens of other things, the message that I care first and foremost about your security can easily get lost. But when most of your instructions and requests center on the idea of staying safe, your teen is more likely to hear you, and to take those messages seriously. Keep personal security the number-one topic: weave it into big-picture talks and regular daily conversations, too. “Do you have a safe way to get home from Brian’s house?” is a better question than “How will you get home?” Make it clear that safety is always top of mind—and most important.

  3.  Appoint safe-harbor adults.  If your son can’t always reach you while you’re at the office, or if he’s reluctant to open up to you about how his friends have started vaping, it’s useful to have a few specific, trusted, designated adults that he can reach out to instead. Those might include your Third Parents, aunts or uncles, family friends, even a former caregiver. Assure him that while those aren’t secret or off-the-record conversations, they’ll never result in judgment or punishment. You simply want him to have reliable adult guidance, whatever he’s facing, and whether you’re busy with work or not.

  4.  Agree on a protocol for moving from A to B.  The beauty of daycare was that your child spent the day in a single, fixed, secured location. But adolescents roam, and it’s when they’re on the move that safety issues tend to crop up. So agree on the rules of the road: that your daughter will always text when she gets safely home from school, let you know before heading to a friend’s, or ask permission before using the car. It won’t cramp her style too much, and that mutual understanding will let you keep tabs while you’re working and step in as needed.

  5.  Have a secret language.  While he’s surrounded by his peers and you’re on the job, your teenager may have a hard time telling you—either on the phone or by message—whether or not he made the soccer team, or that he needs a ride home because the people he’s with have been drinking. Establish a few private signals—slightly unusual words, a tune he can hum, specific emojis—that let him convey messages like Success!, I’m upset, I can’t speak freely right now, and Get me out of here without having to tell you so directly.

  6.  Give safety some spice.  Few teens will see the overall topic of safety as interesting—unless they’re getting an immediate personal benefit from it, it’s exciting or entertaining, or it becomes a bragging right. So encourage them to get summer jobs as lifeguards, go on that overnight wilderness course, get certified at the rock-climbing gym, apprentice to a paramedic as part of their school’s Careers Day, or even just watch that TV show about search-and-rescue operations. The edgier and more personal safety is—the cooler it is—the more likely your teen will be to embrace it.

What are the best ways to stay connected to my teenager, when I have to spend so much time on the job?

  7.  First, rethink what you mean by connection.  If you define connecting as spending large blocks of time together, speaking freely about your lives and feelings, and being perfectly, mutually understood, then you may have a very hard time achieving it. Your work pressures, plus your teen’s own schedule and current emotional wiring, may make that style of bonding close to impossible. Try to think of connection as something different now: as simply being together, without interruptions or conflict. That may mean throwing a ball around in the backyard, with no real agenda, or sitting side by side on the couch, after homework is finished and work emails returned, watching TV. The point is to be there—and be there for your child.

  8.  Observe your kids in their native territory.  How does your son behave when he’s around his peers? What are the other kids on the debate team talking about? Listening to? Even if your work schedule only lets you do so occasionally, try to get some windows of time just to watch your son in context and to understand his day-to-day life away from you. When he does talk to you about his friend’s problems, or about the debate-team dynamics, you’ll be much better able to have the conversation.

  9.  Don’t react; pause, then paraphrase.  If you have only forty-five minutes to spend with your daughter in the evening between when you get home from work and she starts her calculus problem sets, that’s not a lot of time. And if, during that brief window, you respond to whatever she tells you judgmentally or by snapping, she’s unlikely to talk to you at all. If, however, you can listen to whatever she has to say and then nod, wait a beat, take it in, and then repeat what you heard (“So your friend is planning to go to the concert, without asking her parents?”), then she’s more likely to keep on sharing information.

10.  At least once a year, go somewhere.  You don’t have to travel to an exotic foreign city, but if you can take a road trip together to a relative’s house a few hours away, or go camping overnight in the local state park, that one-to-one, in-depth time will be more valuable and truly connective than weeks’ worth of rushed mornings, homework-laden evenings, or after-school phone calls. If overnight travel is out, take a day trip.

11.  Turn off—and turn it off.  Set at least a short weekly blackout period during which you don’t make or allow social plans, and commit to turning off the home Wi-Fi and disregarding to-dos and deadlines. It’s impossible to truly relate to your teen, or for your teen to relate to you, when you’re online, surrounded by others, multitasking, or attempting to be “productive.” Make and preserve the downtime you need for real connection to occur.

How can I help my kids get ready for their “next steps” and adulthood without dropping the ball on my own career?

12.  Open up.  When the kids were little, you learned to set aside your work concerns when you came through the door each evening; you weren’t going to talk to your then-toddler about budget overruns. But don’t shield the kids so much from your work now; talk more about your own work relationships, stresses, and deadlines, and how you navigate them. Offer the kids a realistic if curated glimpse of what you’re dealing with, and help them imagine themselves in the same position.

13.  Ramp up the chores, and make them “zone jobs” instead of discrete tasks.  Ask your daughter to take top-to-bottom responsibility for the dog, instead of just filling the water dish each morning or handling a single vet’s visit. Tell your son it’s his role to get dinner on the table each Sunday evening, as opposed to “helping out” in the kitchen. Make their household contributions look and feel more like the actual adult jobs that you’ll want them to flourish in.

14.  Encourage them to get jobs.  This means real, paying ones, not of the résumé-padding, “internship” kind. A few weeks spent watching the neighbor’s kids, in customer service, waitressing, doing some kind of manual labor, or any other real, fee-earning job will stoke more maturity and readiness for the real adult world than any class at school or lecture from you.

How can I handle the logistics of the ongoing education process, while still delivering at work?

15.  Forewarn your colleagues.  Your coworkers won’t have a good sense for the timeline and actual requirements of the college-or university-admissions shuffle unless you tell them. And conversely, if you don’t tell them, your obvious distraction or repeated, unexplained absences from the office may begin to grate on them. Give your manager, colleagues, and other important counterparties a heads-up, still using the four-part framing strategy you learned back in chapter 3: “Over the next six months, I’ll have various commitments related to Charlie’s university-admissions process. I’ll be handling all those during post-production, and they’ll be over before the show premieres. Six months to airtime!”

16.  Appoint a project manager: your child.  It’s going to be tough to take on all of the logistics and planning yourself, on top of your day job. And if you do, you’re effectively denying your son or daughter the opportunity to own and to learn from this first major step toward adult life. Instead, tell your child that while you’re ready and able to help where needed, he’s in charge and—if he wants to leave home like all of his friends—he’s responsible for seeing this process through.

17.  Use the same collaboration tools you do at work.  Don’t waste time nagging your daughter to show you the latest version of her application essay, or the timeline she’s put together for campus visits: set up a shared drive, agree to save everything onto it, and have full, immediate insight as to what’s being done, how well, and when. Yes, your daughter will hate this—but real-time digital collaboration is how the world works.

18.  Frontload, where possible.  You and your child may have to handle a huge number of tasks in a short period of time, including campus visits, interviews, tests, applications, and financial-aid forms. Where you can, get a jump on the process: visit campuses a year ahead, fill out aid forms as soon as possible, start writing the essays the summer before, and so on. The more you can accordion out all the to-dos, the less overwhelming they’ll be, and the less of a dent they’ll put in your family life and career.

The strain of workparenting a teen is getting to me. Are there ways to make it easier, personally?

19.  Resist the natural inclination to see your child’s every move, statement, or emotional outburst as performance feedback on your parenting.  After so much experience in the workforce, you’ve grown accustomed to constant evaluation; used to reading the tea leaves of senior leaders’ comments, behavior, and body language; and hypersensitized to the political climate around you. But this is a different environment, and a different relationship: not every one of your kid’s choices, glances, or snits “means” something; it’s not necessarily caused by anything you did; and it’s not a referendum on your capabilities or commitment as a mother or father. Don’t overthink the regular ups and downs of teenage behavior.

20.  Remember self-care.  As a brand-new working parent, you may have been more conscious of the need to make your own health and welfare a priority—to squeeze in trips to the gym between daycare drop-off and arrival at work, for example. When you’re fifteen years into workparenting, though, and your child’s end-of-year exam period is looming, it can be easy to ignore your own needs or to let your self-care regimen slide. Try to find some regular, routine time for exercise, hobbies, friends, time alone, and anything else that replenishes your energy.

The kids are so big now! How did that happen … and have I made a terrible mistake and missed out on really parenting them during all these years at work?

21.  No, you haven’t—and try to avoid letting the looming end of full-time workparenting become too much of a trigger for revisionist thinking, for regret, or for remorse. That “where did the time go” feeling hits every mother or father with kids this age, not just the ones who have invested in their careers. Think back on why you went down this road in the first place: you didn’t decide to work despite the kids, but for them. The example you’ve set for them on combining career and family is just what they’ll need in their own futures. And no matter how long you have left before they move on to the next phase in their lives, you can still make a conscious effort to set more time aside to be with and enjoy them. Even when you do become an empty nester, you will forever and always be a working parent.