Career Lessons I Learned From My Earliest Jobs

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.

The Joy That Comes From Showing Up For Your People

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.

When You Know You Need A Break

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.

What Can You Learn By Sitting With Uncertainty?

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.