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.

3 Ways To Prepare To Be A Working Parent

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.

When You Follow The Achievement Formula For Life And Still Feel Lost

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.

The Benefits Of Prioritizing Your Creativity

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.