Is questioning keeping you from fully living?

Thoughts on dedication and the endless quest towards the extraordinary

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Before jumping into this post, I just wanted to say hi and thank you for being here! I’m currently coming off of a six-week hiatus, as October brought many unexpected events, illnesses and necessary reflections (hence today’s newsletter). There’s been so many question marks around both my professional and personal life, and I’ve been slowing piecing together this post as a way to work through the uncertainty. If you find yourself in a similar position, I hope these words will resonate and somehow guide you on your journey!

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A few places where I’ve been “questioning” things lately; captured on my Canon AE-1

We’ve all heard Socrates’ saying, “The unexamined life is not worth living,” but I can’t help but ask: Could an overexamined life be keeping us from actually living?

Sometimes I wonder if I’m the only one who gets dizzy from endless self-inquiry. Surely, I’m not. My thirst for knowledge and self-improvement started young. I can still picture myself wandering the self-help aisle at Barnes & Noble in high school, my mom commenting on my choice of reading material. Years later, that desire to grow and become the best version of myself is still deeply present.

While personal growth is undeniably important, it can easily become an unquenchable thirst—a constant striving to do the work in order to reach a more enlightened existence.

Like many others, I want to live a big, beautiful life, and I’ve always been willing to put in the effort and take the risks to make it happen, from starting multiple businesses to moving to Paris—twice. However, I’ve recently started to wonder if this pressure to create an extraordinary life might actually be getting in the way of simply living (and enjoying) it.

Today I find myself questioning nearly every aspect of my life, screening and identifying potential areas of growth, things to optimize, and edits to make. Inherently, when applied in a healthy, balanced way, this approach is for the best. But when questioning becomes the lens through which we live, it can start to overshadow the act of living itself.

I am very fortunate to live a life with a certain amount of freedom and flexibility, like choosing where we’d like to live and raise our children, as well as pursuing work I’m interested in. However, having such freedoms can add to this unsatisfiable conundrum of choosing wrong, a phenomenon well known as the paradox of choice.

Barry Schwartz helped popularize this concept in his book The Paradox of Choice: Why More Is Less, which explains that while we tend to believe more choice means more freedom, and therefore more happiness, in reality, the effect is often the opposite. Too many options can lead to analysis paralysis—the fear of making the wrong decision—often followed by regret, as we dwell on the paths we didn’t take.

Regardless of the restrictions in our lives, any of us can fall prey to this paradox, whether it’s something as trivial as choosing a show on Netflix or a book to read, or as significant as deciding on a career path or the city in which to raise our family.

As a multi-hyphenate creative with a hand in many projects and a wide range of interests and skills, I’ve long struggled to pick something, afraid of choosing wrong or dedicating seasons of my life to the wrong path. Having started and stopped, and, on paper, “failed” repeatedly, on projects ranging from tech start-ups to a short-lived podcast, I like to believe that all of these experiments will eventually add up to something meaningful.

But I’d be lying if I said I wasn’t scared out of my mind that they won’t.

I tell myself that I am designed to be multifaceted. If you’re familiar with Human Design, I am a manifesting generator, and being multi-passionate is the way I’m meant to move through the world. When something new sparks my interest, or when the current thing starts showing resistance, I drop it almost instantly and rush toward the next project, moving a thousand miles an hour, until the cycle inevitably repeats itself.

It’s a cycle I continue to find myself in. And quite honestly, one I am getting so sick of that I might just be exhausted enough to finally give in and commit to something.

The ideas of commitment and dedication often get a bad rap these days—and I can’t say I haven’t contributed to that perception myself. As someone who highly prioritizes personal freedom, these words have found little place in my vocabulary. That is until several months ago when I stumbled across Dedicated: The Case for Commitment in an Age of Infinite Browsing by Pete Davis in my local library.

Always on the lookout for greener grass, I decided to read it with an open mind, and, to my surprise, it completely altered my perception of dedication.

To many, especially in our world today, choosing something makes us feel like we’re missing out on everything else. In a society where we’re constantly presented with highlight reels of other people’s lives, FOMO has never been greater. Pete Davis writes about the idea of depth in relation to dedication here:

“To overcome the fear of missing out, we have to make the jump from finding meaning through novelty to finding meaning through purpose. To feel confident in making the jump, it helps to keep in mind that the power of depth overcomes the immediate pleasure of novelty. Henry Wadsworth Longfellow wrote that we must choose between being an anvil or a hammer. We’ll either mold the world, or be molded by it. If you never go deep, you will always be the anvil. And the surest path to being the hammer is depth. When we glide on the surface of everything, we’re susceptible to drifting in the wind. We end up chasing shiny thing after shiny thing. And we aren’t substantial enough to stop the world from pushing us around.”

As a multifaceted human who often craves novelty in many areas of life, this passage initially sparked resistance, especially in the professional realm, where we’re commonly told to “find our niche.” Yet, after reading further, my mind began to see the possibility of depth within our many facets. A reality where the two do not have to be mutually exclusive.

We often fall into the trap of thinking that once we make a choice, we’re locked in forever. But that’s not the case. The key is finding a balance between the endless pursuit of novelty—pivoting whenever we encounter resistance or a shiny new idea—and the depth that dedication brings. Dedication doesn’t always have to be hyper-specific, which is another misconception many of us carry. It can be directed toward places and communities, people and relationships, crafts and hobbies, or simply toward a general intention or path.

When practiced this way, dedication doesn’t restrict life; it enriches it, creating a life fully lived rather than one that’s ”missed out on.”

The inspiration for this post comes from weeks of personal questioning fatigue: What direction do I want to take my work in this season of life? Would we be happier living somewhere else? Where should we send our daughter to school next year? Should I delete social media? Or should I just buckle down and be consistent?

It has felt like an acute case of insanity, waking up each day with thoughts completely different from the day before: one day convinced of one direction, the next sprinting toward another. As Davis wrote, it feels like drifting in the wind, with no firm footing, no depth, and a constant sense of being unsettled in life.

As much as “choosing wrong” in the pursuit of an extraordinary life scares me, nothing scares me more than choosing nothing at all, drifting each day in the wind, wondering about potential realities instead of truly being grounded in my own.

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As always, I love hearing from readers. If something in this letter resonated with you, I want to know! Feel free to leave a comment below or reply directly to this mail:)

Until next time,