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Why I started this guide & what to expect
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On January 4th, the first business day after New Year’s, I spoke on a virtual career panel for tech product leaders. Without missing a beat, nearly 100 people gathered on Zoom, fresh from their holiday and ready to take charge of their careers in the new year.
The moderator asked us: “How do you set goals for yourself?”
For the first time, I was taken aback. I gave my standard answer: a 1/3/5 framework. Align with your manager on a specific one year career plan. Come up with three year hypotheses and start testing them. And sketch out a five year dream career that you keep in the back of your mind.
I’ve shared this advice with dozens of mentees, but now it felt inauthentic. Worse, I wanted to roll my eyes at my own framework.
The rest of the panel felt like an out-of-body experience. My mouth espoused the value of staying focused and motivated on one’s next career milestone. My head nodded as another panelist reassured everyone that being a parent and executive during the pandemic is very doable, as long as you prioritize well.
All the while, I felt disturbingly distant from the words we were saying.
Why I’m writing this guide
I’ve been a high achiever for most of my life— from winning competitions in high school, to nailing college admissions, to finding the right brand name job and advancing in my career.
As an adult, I indulged in the modern millennial literature of success (think tech publications, Forbes 30 Under 30, LinkedIn updates, articles about productivity and hustle culture).
I was surrounded by a community of equivalent if not more ravenous achievers. I wrote down goals, and I hit them, and it felt great— like I was winning a race and on my way to somewhere important.
Then the pandemic hit and shook me upside down. It was like an unwanted roommate had moved into my brain and rearranged the furniture in there, exposing cobweb-covered parts that I had shoved into a corner behind the couch. The little glints and glimmers of unanswered questions that I had, for many years, stuffed into airtight containers and shoved underneath the bed.
A few things prompted this figurative shifting of upholstery.
First, I was seeing family far less frequently. It has now been over a year since I’ve seen my mom, and physical distance has underscored the importance of quality time with people I love, time that feels increasingly rare and precious when one is working a demanding job in their thirties, but doesn’t need to be.
As the saying goes, there’s no such thing as having time for something. We choose to make time, and the time we make reflects what is important to us.
Second, quarantine gave me permission to be still and stagnant. I retired my routine of running from office to gym, then to dinner or drinks, then home to wrap up the last of my email threads before sleep. I was deprived of the energy to sprint at 150% capacity toward the next career milestone. I realized that as much as I enjoy living in a big city and having access to its offerings, I savor peaceful, slow leisure way more. And I appreciate more than ever the vast and rare privilege of being able to do so.
Lastly, my partner and I decided to build a house on a five-acre plot of land two hours outside the city. Once the house is complete, everything I want materially in life will largely be fulfilled. I found myself asking: now what?
When I review the goals I wrote for myself just a year ago (become an executive at a rapidly scaling company, get another certification or degree, acquire a specific amount of wealth by a certain age), they feel foreign, as if written by someone else.
Long story short, I began wondering, then intentionally examining what a successful life looks like on my terms.
“Our greatest fear should not be of failure, but of succeeding at things in life that don't really matter.” — Francis Chan
From socialized to self-authored
In her interview on The Knowledge Project, coach and author Jennifer Garvey Berger reflects beautifully on four stages of adult development:
Self sovereign: We are all born with our own needs at the center of our existence. In the self sovereign stage, we struggle adopt others’ perspectives. If we hear something that conflicts with our beliefs and needs, we reject it outright and perhaps throw a tantrum in the grocery aisle. We adopt a black-and-white, us-against-them view of the world. While most adults grow out of this as their primary mindset, recent events show that even as adults, we sometimes let it take the steering wheel.
Socialized: During the process we call “growing up,” most humans shift to a socialized mind. Instead of keeping out other people’s perspectives, we absorb them. Our sense of self worth comes from others and is “imported into you without your say and without your ability to have edit rights on those ways you are being written by the world around you,” says Berger. We look to external reinforcement, praise, and criticism to figure out who we should be and what we should do. Is this the right career for me? Is this the correct thing to do in this situation? Am I going down a good path? The answers to these questions live outside of us. Berger elaborates with example from one of her coaching clients:
Self-authoring: In this state, we choose to be the “decider of all these voices,” to reflect on what’s important to us, and to live by our most authentic principles. We gather all the inputs we’ve been exposed to, clarify what we stand for, and do our best to live by them.
Self-transforming: We give up the notion that we must adhere strictly and wholeheartedly to one singular system of values. As Berger notes, “we begin to live in a world that’s much more collective, that’s much more about understanding what I believe and also what you believe, understanding that together we form a bigger whole.” We develop the ability to hold multiple, and often seemingly conflicting, perspectives at the same time and work across them— because “one truth is never rich enough” in a human life. “Pursuing what’s right” becomes “let’s explore what‘a here.”
By the way, isn’t it funny that in the process of questioning my default success ladder, I’ve managed to identify yet another ladder-like framework to climb?
In all seriousness, most adults operate across these stages depending on the situation. Usually there is a dominant stage that guides the majority of our decisions and behaviors.
What resonates most for me is the notion of self-authorship: claiming edit rights to my definition of a good life. This is where the richness lives— in the opportunity to collate the manuscripts that others have written, do some serious highlighting, annotating, and editing, and rewrite what success means for me at age 31.
What you can expect from this newsletter
2021 will be an important year of growth and reflection. As I dive into a broader, richer literature of success, and tap the wisdom of other achievers with diverse backgrounds and stories, I’d love to share what I find with you. And if you’re on a similar journey, I’d be thrilled to hear your reflections.
Every couple of weeks in 2021, you'll get an email with an update on my rewriting process and a reflection exercise.
By the end of 2021, I’m hoping that:
We will have more clarity and wisdom about what success means to us
We will have examined our starting definitions of success and decided which elements we want to keep and which we want to shift
We will start shifting from “success on autopilot” to a more intentional approach on our own terms
Reflection #01: Who were the authors of your life growing up? How has that changed over time? Who authors (or co-authors) your definition of success now?
Love and health,