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.

Three Things To Grow Rich In (That Aren’t Money)

Wealth can be created across more areas than just financially. Sure, monetary wealth can be a beautiful thing, and I’ve got aims to grow wealthy in money. But there’s three areas that are more important to me for wealth than just money.


The length of your life, your enjoyment of it, and the way you experience it directly relates to the quality of your experiences. When you’re young, travel. Seek out new opportunities. When you’re any age, really. As we slow down and move into habit and routine, we can lose time simply because we aren’t aware that it is passing.

Experiences are the foundation of connection, conversation, memory, and growth. When evaluating opportunities, I think: Will this add to my wealth of experiences?


Richness is friendships. I want to be full, overflowing, satiated, bursting with love for my friends and my family and my colleagues. I want to take on the heartbreak and the sadness and the pain that comes alongside love and laughter and joy, because it means I’ll be there with them, and they’ll be there with me.

True friendship can be inconvenient, it can be messy, it can be laborious (driving hours each way to see someone; giving up other opportunities to make time, whatever it takes)—but it’s also a wealth worth building. At the end of the day, I want someone to hold my hand and tell me we did enough, that our time mattered, and that we were lucky to spend it alongside each other.


Education is never-ending. One of my favorite ways of framing my own personal education is thinking about life in two-year spans. It takes two years to really dig in deep enough to an area to learn about it and find an intermediate level of mastery of the material. I have, ideally, quite a few two-year spans in my life.

My journey into storytelling and marketing was a two-year self-guided journey into reading 85 different books on positioning, storytelling, communications, and more. It has served me dividends already in all of the work that I do. My parenting journey is another education; my business, yet another one. Never stop learning, or investing, in your education.

Yes, I love money (and I love writing that!)—and I also want to be wealthy in experiences, friendships, and wisdom.

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 ofRead the article

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