We all know it’s been too long since I’ve sent out one of these newsletters… let’s just move past that. I hope you all have been well. Things on my end have been great! Since I’ve last sent a newsletter, I got married and explored southeast Asia for our honeymoon (12 out of 10—would highly recommend checking out Borneo).

I’m excited to be behind the keyboard once again. Thank you to many of you for encouraging me to get back to writing (you all know who you are). Much appreciated.

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Let’s party:

“Deep down, nobody really knows anything,” I blurted out matter-of-factly—frustrated with the current direction of the class conversation. I was sitting in one of my final MBA classes (People, Power, and Politics) at NYU Stern. It was a crisp November morning. Plenty of students were gripping their pumpkin-spiced lattes and sharing their grievances about toxic work environments.

At the moment of my boldness, we were talking about leadership and imposter syndrome. As the conversation shifted to the different techniques people use to overcome feelings of self-doubt and anxiety, the class could have been mistaken for a needed therapy session. Student after student shared example after example of times he or she felt like a fraud.

Mind you, I was in a room of 40 high-achieving, mid-career professionals—all hailing from top undergrad schools and employers. How was it possible that so many people had the same experience of anxiously waiting for the moment when everyone found out they don’t belong? Myself included.

As my moment of clarity continued to brush over me, I continued sharing my perspective with my classmates. “Why are we all doubting ourselves when it’s clear nobody knows anything? It’s silly to feel like an imposter when clearly everyone around you feels the same way. Everyone’s just doing their best, and most of the time that’s plenty good enough.”

Socrates is famous for saying:

I am the wisest man alive, for I know one thing, and that is that I know nothing.

“Nobody knows” is Socrates dumbed down and simplified. Feelings of being an imposter should fade upon the realization that if you’re a fraud, then so too is everyone else.

Yet, our minds love to play tricks on us. What’s the modern workplace if not a playground for social politics and a sandbox for figuring out your own self-worth?

I’ve had imposter syndrome many times throughout my career:

When I moved to San Francisco to start my career at LinkedIn, I thought “I hope the leaders of my rotational program don’t realize they should have accepted these other students from Northwestern.”
When I changed roles and joined the insights team, I thought “I hope my manager doesn’t regret hiring me when I don’t know how to code as well as the rest of the team.”
When I was accepted into NYU Stern’s Tech MBA program, I thought “I can’t believe admissions picked me vs the hundreds of others who applied.”
When I started Gridology, I thought “Will anyone care what I have to say? What on Earth do I actually know?”
When I became Chief of Staff at Sounder, I thought “I hope I know what I’m doing.”

Realizing that everyone alongside you is winging it is the first step toward putting imposter syndrome behind you. Today’s grid builds on what to do next. Feelings of self-doubt are normal when society has trained us to believe it at every turn.

On the x-axis, we have the people you choose to engage. When imposter syndrome strikes, who do you consult? Choosing the right community to help you build your confidence can cause feelings of imposter syndrome to dissipate quickly. Opting to confront imposter syndrome alone prevents growth.

On the y-axis, we have your ego. In life, are you humble or arrogant about your capabilities? Are you quick to admit your blindspots or do you tend to bullshit your way through things you don’t know? Having the right attitude about professional development is essential in overcoming feelings of self-doubt.

Understanding the Grid

This grid illuminates that the best way to overcome imposter syndrome is with curiosity. When you have a growth mindset and invest in a quality support community, anxiety and stress start to fade.

Curiosity

You seek out community and do so with humility. When I started as Chief of Staff at Sounder, I felt overwhelmed. In classic startup fashion, my role is to wear many hats across the business: marketing, business operations, investor management, and other priority projects that pop up along the way. While I had a strong belief in my skill set to meet deadlines and figure stuff out, many of my day-to-day responsibilities were new for me. So rather than wallow in self-doubt, I sought a community to help. When I joined the On Deck Chief of Staff fellowship, it exposed me to a group of people who had similar roles and dealt with similar feelings. The fellowship even had a session on how to handle imposter syndrome earlier this year.

After many of the conversations I had with my peers, what became clear to me was how everyone had a similar story of self-doubt to tell. With so many people looking to fill in their blindspots with collective group wisdom, I felt less alone. My confidence and—in turn—my effectiveness improved. Imposter syndrome transformed from feelings of self-doubt to an opportunity for accelerated growth.

There are so many different types of valuable communities. My On Deck fellowship is one small example. Whether you invest time in your own personal board of directors, close family, or friends, know that spending time sharing and learning from others about your feelings of imposter syndrome will give you greater confidence in your ability to achieve.

Peacocking

You seek out community and do so with arrogance. If you trade humility for arrogance in a group setting, you’re set up to gain far less wisdom. If I had entered my On Deck fellowship with an ego, it would have prevented me from learning new skills needed to get better at my job. In this setting, being arrogant would have shielded me from others in the program seeing me as incapable or undeserving of my title. If I pretend to know everything, then clearly I know what I’m doing and have a lot to offer! That’s just science.

However, this would have been a massive miss. Peacocking can work but only temporarily. It’s only a matter of time before expectations for your abilities do not match reality. The community could and most likely will reject you for your dishonesty and lack of value.

Overcoming imposter syndrome is not simply convincing others that you know what you’re doing. It is realizing that while nobody expects you to have all the answers, they do expect you to be able to find them and then act accordingly. When you’re pretending to be something you’re not, you’ve actually failed at the assignment. When you engage with a community, gain value from it by being eager to learn. Bring these learnings back with you to your job—making you more productive, successful, and confident.

Doubt

You isolate yourself and act with humility. In this quadrant, negative self-talk runs rampant. You feel out of place and anxious. Oftentimes nothing is actually going wrong at work. However, your lack of confidence is destroying your perception of how you are performing at work. Because you’ve isolated yourself, you don’t have anyone to tell you that these feelings are common. There’s no one there to coach you through difficult moments. Oftentimes the isolation can cause self-loathing, frustration, and inaction. Because you feel out of place at work, you can start disengaging entirely. Feeling alone and undeserving are two key ingredients for an imposter syndrome cocktail.

Posturing

You isolate yourself and act with arrogance. Like peacocking, you are pretending you have skills you don’t actually have. However, when you’re posturing you’re doing so with your colleagues and teammates rather than with an external community. This is a recipe for disaster. If you were hired to do a job and then are all talk and no game, you’re on a path to a quick termination. Arrogance is the kiss of death.

A quality treatment option for imposter syndrome is positive feedback. When you are learning and growing, you—logically—get better at your job. However, when you don’t know what you’re doing and make it as if you do, positive feedback is not headed your way. Posturing saves face in the short-term to only destroy it in the long term. Opt to be open about your shortcomings and eager to learn. Your team will respect you more for it.

Grid Shortcomings

This grid doesn’t take into account self-guided learning. While the doubt quadrant is real—I’ve certainly been there—there’s also an alternative to it. Though you chose to isolate yourself, you could have engaged in private learning to build your skill set. Recognizing you don’t have all the skills needed to thrive in your job, you take courses, watch videos, and read books to fill in blind spots and build confidence. Not all growth stems from engaging with a community. However, when it comes to overcoming imposter syndrome, communities help increase the speed at which you can grow. When learning as part of a group, skill gaps are quickly identified and addressed while your emotions are cared for.
This grid doesn’t take therapy into account. Talking to a therapist about feelings of self-doubt and anxiety is a powerful tool to help you adjust the narratives you tell yourself. It’s helped me immensely.

The cure for imposter syndrome is a deep devotion to having a growth mindset. The more you believe that you are a work in progress, the less pressure you put on yourself to achieve at all times in every situation. Give yourself some grace. You’re where you are in life because you deserve to be there.

Life’s only as confusing as you let it be,
Ross

P.S. Thank you Fred again.. for powering my 5am writing session to get this post out. Unbelievable what you can accomplish when you can’t sleep and have awesome music.

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