Category Archives: Big Life Questions

What makes a life worth living? What will you do with your one “wild and precious life”? How will you design the arc of your time here on the planet? Let’s ask big questions.

How Will You Measure Your Life? The Art of Managing Yourself

This morning I was fortunate enough to wake up at 5:06am, an hour before my baby wakes up, and I had a rare hour to myself to read, write, and meditate. I picked up an HBR series called “On Managing Yourself” and meandered through Clayton Christensen’s essay, “How Will You Measure Your Life?” These are some of his insights that stuck with me, from how to spend your time, to why management is such a critical art in both your personal and professional life.

For me, mornings have been different for the last two years, first because of the fatigue of pregnancy (where waking up early was a rarity) and then because of the newness and immediacy of motherhood. I haven’t had time to write like I used to.

Instead, my mornings now look like this: my little one and I rise around 6am, and we spend the first two hours of the day feeding, changing, playing, nursing, getting dressed, getting food prepped, and walking to daycare. It’s a shift of no small measure. It’s time for me to be present with my kid, and moreover: it’s a time when he needs me to be there, continuously, in service to his needs.

So waking up before he did was a pleasant surprise, and I can’t express the gratitude I have for being able to read slowly and uninterrupted. Here’s what I learned this morning about creating your life and managing yourself:

1. Create a strategy for your life.

We create strategies for our businesses and our work, but we rarely create strategies for our own lives. As a result, our personal relationships and overall happiness suffer, because we forget to invest in things like relationships, spending time with family, cultivating a strong connection with our spouse, and enjoying our children or side projects. Managing yourself and your time is as valuable as the work that you do in your career.
“Keep the purpose of your life front and center as you decide how to spent your time, talents, and energy.” — Clayton Christensen

2. We consistently allocate resources ineffectively. First, by over-allocating time and resources to our careers, and second, by under-allocating to our other pursuits.

“When people who have a high need for achievement have an extra half-hour of time or an extra ounce of energy, they’ll unconsciously allocate it to activities that yield the most tangible accomplishments,” he writes. And because our careers are the easiest place to measure our output, it’s easy to spend most of our time, effort, and energy on our careers. But is this wise, and is this truly what we want? “Raising a great kid,” doesn’t have an easy metric, and probably never will. But it might be something that you want to spend time on. Knowing that it’s harder to allocate time to things that aren’t as easy to measure output-wise can help us re-center our attention across all of the things that matter to us.

3. Management is the most noble of professions if it’s practiced well.

If you’re managing other people, or even yourself, your job is extremely important. You don’t just manage the time people spend at work, you also shape the way people leave work at the end of the day, and how they are when they head home.

If you’ve been a shitty manager, you may have people leave work frustrated, disappointed, or discouraged, and that’s who they are when they head home to their families. What if you could manage to leave people inspired, accomplished, and satisfied, and they went home feeling full, grounded, and creative?

In my own business, it reminds me that I’m not just hiring someone to “get things done.” I’m hiring for relationships, for deeply satisfying work, and for joy. The people I’m working with now on Startup Pregnant are deeply intuitive, thoughtful, and mindful. They bring me joy to work with them, and, it’s my hope that I inspire them as well.

And in your own life, if you treat it like a business, reflect: how are you managing yourself and your time? Are you treating your life like the valuable asset and creation it is?

4. Consulting and coaching aren’t about providing specific solutions; they’re about guiding people through a process that helps them find the solution on their own.

“When people ask what I think they should do, I rarely answer their question directly,” Christensen writes. “Instead, I run the question aloud through one of my models […] and they’ll answer their own question more insightfully than I could have.”

The most profound leaders all share this wise insight: that coaching and providing insight to others isn’t about telling them what to do. It’s about cultivating deep listening practices and guiding people towards a way to access insights within their own wisdom. What I’ve been reading lately — Krista Tippet’s On Being Wise, to Michael Bungay Stanier’s The Coaching Habit, and to the deep listening practices from Thich Naht Hanh — are all influencing the models I’ve built in my private Mastermind accelerator. In our small group, where confidentiality and conversation are paramount, our monthly Deep Dive practices  are not about giving advice to each other, but about constructive, effective deep listening practices to guide people into better understanding themselves and the puzzles they’re working on.

5. “Just this once” is the most dangerous justification, and is probably why people end up cheating, being dishonest, and going to jail.

The simplest justification to yourself is that you’ll only do something once. If you follow this to it’s logical end, you’ll regret where you end up.

6. Humility comes from high self-esteem, not low self-esteem.

Having a high sense of self-esteem and a high regard for others were the traits that Christensen found were most in line with the most humble people they knew. “They knew who they were, and they felt good about who they were.” People who feel good about themselves are not boastful or self-deprecating. They are satisfied and eager to connect with others, and to help others grow as well.

In his work with the highest achievers at places like Harvard, he found that people could develop and grow to a point where they felt they no longer had mentors or people to look up to. This, however, was important to learn from. “If your attitude is that only smarter people have something to teach you, your learning opportunities will be very limited,” he writes. Instead, stay humble, stay eager, and remember that you can learn from everyone.

7. Know how you measure your life

“Don’t worry about the level of individual prominence you’ve achieve; worry about the individuals you’ve helped to become better people.” — Christensen

As he gets older, Christensen says that his projects or accomplishments matter less and less, but the individual lives he’s touched are what matters most. I’m inspired to bring this into my life, and remember that now, the only thing I have is the people in front of me in this moment, and the attention and love I can bring into today.

And as I finish typing this, my baby is knocking on the crib, reminding me that it’s time to put my book down, set my phone aside, and go help him up out of the crib and into his day. Spending time with him might not get more writing done, and it might not help me check off more from my To-Do list for work, but it will be part of the whole life that I’m living, and I’m grateful to spend time with him. And I’m grateful that this morning, I woke up early enough to write again. In reflecting on my self-management, I wonder, is it time to start rising early again to make more space for writing?

An Answer For Everything

There’s an answer for everything. Every choice, every decision, every reason for being. When you feel the impulse to dance, or wiggle, or scream, or wring your hands in frustration. When you think you don’t want to go to a meeting, when you hate getting on the subway, when you want to quit working withRead the article

Take Up Space

Take up space. Take up space with your body. With your gestures, with your height, with your size. If you’re petite, take up space. If you’re tall, take up space. Fill the room with the weight of your body, and then expand again with the weight of your soul. Take up space with your voice.Read the article

Are You Chasing Productivity At The Expense of Your Soul?

I’m struggling with two competing challenges: being present and mindful, while also chasing the ego-driven aims of “success” and “productivity.” Is there a middle ground? I reached out to my dear friend Mathias Jakobsen, author and creator of Think Clearly, to dissect this competing pull between these two desires. This is the conversation. Two CompetingRead the article

How We See Ourselves: On Identity, Labels, and Privilege

Do you know the story about when a man is asked to look in a mirror? He’s asked what he sees. He says “myself” (usually he says his name, “I see John,” etc). A woman looks in the mirror and says, “I see a woman.” A black woman says, “I see a black woman.” How weRead the article

The Profound Habit of Following Your Own Advice

Wisdom is nothing more profound than an ability to follow your own advice. — Sam Harris. I struggle with writing essays that sound too much like advice, because I know inevitably as soon as I tell you the ten tricks for getting into bed early, I’ll suffer bouts of insomnia, wake up at odd hours,Read the article

Making Space: Holding the Container Open, Empty, and Ready

Cleaning out sometimes feels a bit like a death. Whenever I pack up bags to give away, it feels as though I’m going through old remnants of my past self, closets of things that represent who I used to be, and parting ways. Lately I’ve been cleaning out everything: getting rid of extra toiletries, clothes,Read the article

What would you bring with you into the woods? Reflection questions on your own fire, the art of creation, the necessity of destruction, and your intrinsic value.

Central Park by Vivienne Gucwa on NY Through The Lens. Reflection, rejuvenation, and three questions. This weekend, I left the city to join one hundred other entrepreneurs, creatives, and innovators to shake off some digital dust and retreat in the Poconos Mountains of Eastern Pennsylvania. In addition to the typical packing instructions — sleeping bag,Read the article

When I hold on too tight…

I’ve noticed that when I hold on to things, it doesn’t mean that they get better. When I held on–and I held on so tight! –the writing didn’t get better, the launch of my newsletter didn’t get any better; it got longer. It almost disappeared into the abyss of doubts and worries, of perfections and neuroses; itRead the article

“You can have everything you want.” — “You will never be enough.”

Are we being taught to want everything and never be happy with anything that we get? Why these two cultural mindsets don’t serve us–and how pervasive they are in our everyday lives.Read the article