I started babysitting when I was 10 years old. Looking back now, I’m not sure why anyone trusted me with a child at that age, but I do know I gave that job 110%.

I exuberantly sang every toddler-favorite melody.

I got on the floor and built towers that were knocked down a thousand times.

I washed every dish in the sink even if I didn’t dirty it. (Teenage sitters of 2019 please take note!)

Once I had a taste of working, making my own money and learning new skills outside of the classroom, I was hooked. From babysitting, retail, teaching, waitressing, through to television and film production work—I had jobs throughout middle school, high school and college—and looking back now, I realize I learned critical skills that helped me take leaps in my post-college career.

As I look around at teenagers today and to junior employees at organizations with whom I work—I’m seeing this practice of early job experience begin to fade away. According to Business Insider, "Almost 60% of teens in 1979 had a job, compared to 34% in 2015." The reasons behind this trend appear to be an increasing intensity in school and homework, a prioritization of academic achievement and extracurricular activities over all else and a pervasiveness of helicopter parenting that is at odds with the self-sufficient nature of having one’s own path towards independence.

From my perspective, this is a damn shame.

Here are some of the skills I learned in my early work experience that impacted my career, my life and the way I will parent my two girls:

1. Problem solving
When there’s a toddler crying in his bed because he misses his mommy, two burger specials with cheese fries that go missing or an endless line at the register during a spring sale—you need to think on your feet and do your best to figure out how you’re going to deal with it. And it’s not just about you. There are others relying on you: kids that need their sleep; businesses that need to run. The added push to do your best for someone outside of yourself will be excellent practice for how you can show up as a leader in your career and in your life.

2. Relationship building
When I was in high school, I had some great bosses. At one children’s clothing store where I worked for two years, my boss Lydia, the store manager, taught me nearly every aspect of the business. She believed in me, wanted me to learn AND was very generous with feedback. In school our relationships with teachers were one to many, where as at work—I was one of very few employees that Lydia mentored. She cared about me, but she also set boundaries so that it remained a work-focused relationship. It was an opportunity for me to get coached early, accept feedback and learn how to navigate safe, clear professional relationships.

3. Self-reliance
Because I was often employed, I walked through my early career with the knowledge that I was quite employable. I knew how to interview. I knew how to go above and beyond. I learned how to show up on time and how to juggle my responsibilities of work and school, clearly a skill that has set me up well for working parenthood! While I wasn’t earning a salary I could live on until after college, my early work experience gave me the confidence that this would be possible.

In a culture where we’re maniacally focused on our kids’ academic coursework and grades, we’re forgetting about some of the foundational skills that would make them both employable and good employees. Also, some kids who don’t excel in school, may find their groove in their jobs. I know I truly preferred my first four years of working to my four years of college. I appear to learn more efficiently when I’m doing—and I’m certain I’m not alone in that! With my girls, I will encourage them to babysit, pay them to help me with my business if they’re interested or look into ways they can jump into the world of work that speak to them. What’s important to me is that they have this opportunity to learn and grow in a way that can compliment all they’re learning in school and at home—and make some spending money in the process.

One of my dearest friends premiered her film at the Tribeca Film Festival last week—and I was there to take in the moment. Sitting alongside my co-cheerleaders in the audience, we held onto each other and watched our girl shine on a panel of women filmmakers as we have done at all the screenings, fundraisers, focus groups and award ceremonies for the past 20+ years.

Bearing witness to my friend’s optimism, resilience and dogged persistence in an industry that’s only beginning to recognize the talent, value and contribution of women, leaves me with a heart full of gratitude to be on this journey alongside her. It has been a road filled with both disappointment and accolades, but being there—on both ends of the spectrum—is what makes the reward that much sweeter for everyone.

It’s a counterintuitive lesson in life, but I’ve found that somehow, it’s easier to show up for friends during the hard times. We spring into action, call in our resources and project manage the shit out of a crisis. We often feel more vulnerable showing up for the highs and I’ve taken note of those friends who’ve been there for me.

In the audience when I was singing my heart out in my twenties.

Peppered along the NYC marathon route with signs, families and protection from the wind.

Front row at my first talks and workshops after my career transition.

It’s not always easy to be there. It takes:

Saying yes and then rearranging your life logistics to make it so.

Confidence in your own successes and progress on your path.

Freedom from comparisons and judgment.

But what I continue to learn from showing up for my people and being supported by them is that while we are all on our own unique paths, our momentum, our resilience and our joy is collective. We feel it exponentially when it is shared. And it is not about critique or validation. Being there is about making people feel truly seen…and loved.

If you’ve been following along, you know that I’ve just come through an intense period on the school-front with my older daughter. The lead up to learning about her middle school placement was stressful, and frankly, consuming—even though I coached myself through it several times a day.

Now that time is over. We know where she will go. We do feel lucky—especially given that placements were determined by lottery this year, and yet the day after we learned the news, I could not move on. I was still in knots and this was truly bad timing for my stagnant energy.

I knew I could use a break, a weeklong vacation, a day off (even an afternoon of playing hooky!) but I had much to accomplish that week: namely two corporate proposals and a workshop to plan on top of existing client sessions. I had the time blocked out on my calendar to do these bigger projects, but I was simply unable to string coherent sentences together.

I slammed my laptop shut, got some coaching from a colleague and friend, and was able to get what I needed to move on without booking an immediate beach vacation.

Here’s how to move forward in the short-term, when you know you need a break:

1. Acknowledge your effort
Man, I went to 12 school tours, countless meetings, managed a village worth of expectations—including those of a ten-year-old—and I was exhausted. I let this wash over me and you can too. Remind yourself of all you’ve done, the time and energy you’ve spent. Even if the results weren’t completely how you desired them to be, you worked hard and you did your best. Own it.

2. Refuel
When I thought about my reason for needing a weeklong vacation at that very moment, it was to de-pretzel. To relax. To renew. I put on my sneakers and walked in the park until I began to feel some release, some relief from this stuck place. You can do whatever you do that brings you energy and moves you through stress.

3. Reconnect to your "why"
After doing some work to put my recent past to rest, I needed a way to get my momentum back on the projects in front of me. My friend asked me a brilliant and simple question. "Why is this work important?" And I was back. Once I began talking about this work that I love—supporting employees in defining the leaders they want to be, while having the courage to be themselves instead of making comparisons to others—I was hooked and excited to dive in. What’s your "why" for the work you’re doing?

While I was able to complete my work last week and feel truly proud of what I accomplished, I did fight that nagging feeling that there was more I could have done. I knew I still wasn’t working with a full tank and to make it through I needed to set expectations accordingly. Be happy with quality, not quantity. Do the highest priority items and let some less important things slide. Hello, pile of mail growing on my counter. I’ll commune with you another day! Most importantly, I took the whole weekend off: Passover with family and extra time with my girls. While the beach isn’t in the cards just yet, I continue to build in mini-breaks so I can slowly get my mojo back and move on.

Three weeks ago my productivity came to a grinding halt. While I had two new exciting projects to tackle—my mind was focused on one thing.

The thing for which I had no control.

The thing I judged myself for obsessing over even as I wrote this.

It seemed like such a teeny, tiny thing relative to all that was happening in the world and for other people. And yet, there I was. In a place where it was the only thing I could write about.

My daughter’s New York City middle school placement for next year.

A week later, I now know where she will go and the uncertainty is over.

But when I sat in the unknown—waiting on this important piece of data for our family—I was driven to ask, “Why is this taking up so much real estate in my brain right now?”

I’m an entrepreneur. I live in the space of uncertainty. My job and my path are completely unpredictable to me—and I thrive in this world where I create many things out of nothing.

So what’s different here? Why for weeks, did I painstakingly finish my writing and then decide to do my 57th Google search to see if anyone had heard anything about the day the placements would be released? With each search, I simultaneously prayed that I would be a more evolved parent by the time we hit high school and college anticipated results.

I’ve deduced that it wasn’t about:

My daughter’s mental state, because she was 100 percent cooler than me throughout the process.

The actual schools, because I know they are all good in their own ways and that we, as parents, have the power to make them even better.

Yet, it was about a practice of:

Releasing perfectionism and the notion that there was one more thing I could have done better in the process.

Breathing through my pre-feeling of what I expected her emotions to be.

I can’t protect her from disappointment or heartbreak and if I do, I’m robbing her of the experience of learning resilience in the face of those life moments.

And so, I breathed. I let go. I instituted a Google embargo for the week the results were released. I sat with the discomfort in the hopes that it was the very thing that would make me evolve before the next milestones come our way.

I did what I do during moments of stress. I wrote (thanks for listening), walked in the park, belted out show tunes with my girls and played rowdy games of tug of war with my puppy.

I drew the direct line between the career-focused resilience I’m helping my clients build in our work and the moment my daughter was facing—and I knew that no matter what news would be revealed, we would learn and we would be OK.

Despite my evolving feelings about Sheryl Sandberg’s Lean In, one gem of wisdom that I continue to find critical as I’m coaching those who plan to become working parents in the near future is, "Don’t leave before you leave." Women take themselves off their career paths and out of workplaces that could potentially be supportive because of looming fears that they will be overwhelmed—needing to do it all and look perfect while doing it. Yet Laura Vanderkam points out in her book, I Know How She Does It, that often times the more senior roles bring greater autonomy and control over one’s schedule—so continuing on the rising path can offer more flexibility than most women assume.

Instead of taking yourself out of the game prematurely, if you’re considering starting a family within the next three years, I recommend these three paths forward:

1. Learn the art of authentic self-promotion
As I continue to point out in my writing, workshops and work with clients—doing good work is important. But it is not what gets you a larger budget for your project, head count on your team, promotions or raises. Most importantly, it does not help you make a bigger impact in your organization or in the world. You MUST tell people about the good work you’re doing, the work you’re proud to produce and the teams you’ve built. I’ve outlined ways to practice this skill in my 5 Commandments Of Self-Promotion. If you plant the seeds of your value early and often, when it comes time to have conversations about flexibility to navigate working parent life, you will find yourself having a vastly different dialogue than if you begin proving your value at the very moment you need support.

2. Practice boundary setting
How do you envision your working parent life to look? Truly, you will never know how it will go until you get there, but you can run some experiments and simulations that include setting clear boundaries around time. You can practice leaving the office at 5:30, perhaps exercise or cook a healthy meal instead of ordering in. Make your health a priority during this time, and beyond the benefits you will receive in energy, you will learn the art of asking for what you want…and holding to it. You can always get back online for an hour or so after you’re exercised, fed and on your couch—if you think it will help you get a better night’s sleep and start fresh in the AM. Notice how it feels for you to set different boundaries. What comes up? How can you work through it with your leaders? How can you be more efficient with your time while you’re in the office so that the organization will not be negatively impacted by this change?

3. Build out your network
Seek out other working parents who appear to be doing it well. Learn from them. Nurture these relationships so you can expand your understanding of what’s possible and be inspired by all they’re pulling off. Also, use this time to find advocates within your company and beyond. Before I had my first daughter, a former colleague was looking to recruit me into his new organization. I was transparent—as I have a tendency to be—and told him, "I’m on the path to having a child. If you have something flexible to offer in a year or so, I’m in." Eyes wide, he was not expecting that to come out of my mouth, and yet he hired me a year and a half later for a flexible marketing role where I controlled my hours.

As with anything in life, the more intentional you are about what you want to create, the more likely it is that you will make it so. While you don’t need to switch gears to get on what you assume is the mommy or parent track, you can begin thinking about your vision—redefining what success looks like for you as you enter working parenthood, while testing the waters to see if you’re in a place that will support you in claiming it.

In April, my daughter will celebrate her 11th birthday—the milestone I’ve anticipated since she was born. This May will mark 33 years since my parents died in a car accident. I was 11. In the past year, the build up toward this day and the expectations of who I might become in the face of this moment have prompted me to go inward and sit with my fears.

Intimate knowledge of an 11-year-old mind and heart will make me realize how unformed I was.

I will discover there are parts of me that won’t heal.

I won’t know how to parent a child past the age I was parented.

In the past year most of my conversations around my lingering grief have come to the surface via this topic, this experience that has yet to happen. With friends, a support group of motherless mothers and with my husband—there was a knowing that an expected bolt of lightning was about to strike. And I was waiting. While I will never know if shining a light on this moment changed my experience of it—now that I’m here—I’m in awe of how completely different it is than the visions etched in my mind.

Instead of seeing an 11-year-old who is unformed, there is a young woman who is capable, expressive, curious, confident and strong. Even if I had a fraction of the will and hope she has, I get why I would have made it—and did. We have a love for writing in common, and with every poem she weaves and then reads aloud to me (for the 27th time), I realize I was lucky to have a way to channel my feelings and thoughts and fears, beyond the emotional readiness of my friends.

Living with an almost 11-year-old is reminding me that there are parts of me that have yet to heal. This is a moment to use my compassion for both of us to tend to this part of the wound. While I wasn’t truly parented after age 11, I was loved. And that love may be just enough to fill the deficit so I can create something completely new when it comes to being a mom to my girls. I’m doing it my own way, which given my personality, is how I might have done it no matter how my life unfolded. But now that it’s the only path forward, it feels like a way to carry my parents with me as loving witnesses instead of the knowing guides that others may have. Looking at my almost birthday girl, I know this plan has worked pretty damn well so far, so I’m in.

At my 5th grade daughter’s Parent Teacher Conference, we discussed her report card. Her grounded, wise teacher held up the card and cautioned us—"Please make sure she knows she’s thriving and this isn’t the only proof. Do your best to reinforce success is not about this."

In our household, we’ve always focused on kindness, empathy, curiosity, and a hunger for learning—and frankly, both our girls could recite the Garrett TED Talk on the importance of effort word for word. But when the mirage of validation stares you down in the form of a lineup of high marks—it’s difficult to take a measured approach to praise.

The achievement seduction is real.

It’s the belief that if I get the grades, win the awards, get into the schools, land the good on paper jobs—I’m guaranteed a successful life. A happy life.

To be clear, I know that academic effort, striving and persistence toward goals are important variables in moving through childhood into an adulthood where both happiness and financial health are possibilities. But these things do not make up the full picture and they do not provide guarantees. Our maniacal focus on achievement is out of proportion to what it can offer—leaving many of us in perfectionism, anxiety and a desperation for validation, promotions and external praise. At the same time, those who focus on accolades are often out of touch with what drives them outside of our society’s formula for success.

When I support women mid-career, they hit this identity-shifting moment. After a lifetime of striving toward things that seemed important, they realize that these aren’t the things that are important to them. Acknowledging the dissonance to anyone feels like a failure and an unimaginable risk. There’s no roadmap for doing life outside the formula.

The first step out of these woods is compassion for that young person, who dutifully followed the rules and diligently worked to get to this place. Who wouldn’t want the life you were promised? You were expecting certainty where it never truly existed, and now the idea of taking a path where uncertainty is known can be terrifying. This process of uncovering how you want to live your life requires courage and patience. A simultaneous quieting of the noise of others’ expectations and a deep listening to your intuition that you’ve become skilled at silencing.

From there you can find pride and momentum in both the weaving together of those moments that ignited you throughout your life and the relentless exploration of things you’ve always hungered to learn and do. My clients who move down this path build their own companies and create new roles at organizations they admire by writing job descriptions around their strengths. They finally give themselves permission to pursue their creative projects and they unapologetically show up in their lives as the people they are, rather than those others wanted them to be. Once you are free from whatever your 5th grade report card said about you, the university you did or didn’t get into and the title you’re supposed to have by your age, you regain control of your choices and your life.

Lately, I’ve been tucking in my nearly eleven-year-old daughter at her set (early!) bedtime, only to see her pop out of her room an hour later with an energized grin.

"Can I read you the poem I just wrote? It’s three pages. I’m really proud of it."

Then, she weaves her words—descriptive and dark—connected by metaphor and hope. Leaving me wondering—uhm—what happened at school today?

I ask what inspired her to write this thoughtful and expressive piece and she reminds me of something I know, but also something I allow my rigid adult brain to resist.

"Mom, when I write a poem, I have the idea and then I just sit down and it comes out. I don’t even think about it."

After highlighting some details that stood out to me in her work and watching her smile grow, I thought, "Profound. I want that."

While I do feel those moments of flow with my writing—there’s often that editing voice I’m quieting as I go. I’m skilled at navigating that voice in my reserved weekly three-hour block—and most days, I wish that time didn’t have to end. Yet, I would be lying if I said it was always a flow or that each time I truly let go.

Even as I work through shifting my presence in my writing practice, for the past two plus years I’ve proudly made my creativity a priority in my business and my life, and that commitment has transformed who I am.

I schedule out writing time on my calendar a month in advance.

I guard that time with my life, not accepting any sessions, meetings or phone calls. OK, so I do look at emails and texts, but this is a work in progress, people!

During those hours, I gift myself the chance to observe the world, to make sense of it, to be raw and human. It’s a time to simultaneously be imperfect and whole.

And what I receive in return is immeasurable.

Energy.

Points of connection with people in my life and those I’ve never met. A playground to make mistakes. A place of joy where it’s safe to practice letting go, a lesson I then bring to areas of my life where I continue to indulge my fears.

I’m reminded of creativity’s impact on who we are as humans when I bear witness to my child’s ability to go deep in a quiet place, to be a vessel and to listen without thinking. When I see who she’s becoming, the confidence she’s building and her knowledge of self that is a direct result of her practice, I am moved by what’s possible for both of our lives and the life we share together.