The Imposters of Silicon Valley

As a child, my mother would tell me to stop trying to grow up so fast…

I wasn’t raised in the Bay Area — I moved here after college (as many do) to pursue a career in high tech. Unlike many, however, I was fortunate enough to land an entry level SDR job at a young file sharing startup in Palo Alto called

Immediately, I fell in love with our industry. I owe a lot to the early team at Box for such a warm introduction to startup life.

Could you really blame me though? There was something so… romantic in the air surrounding California Avenue in 2009. You had the sense that anything was possible — that with a great idea and enough hard work, you could become anything you wanted.

Four years later, I became the first marketing hire at Gainsight. Now, I’m the Chief Marketing Officer.


Without discrediting any of the hard work that got me here (more on that later), my path navigating the first eight years of my professional career seemed characterized by both preparation and luck. Looking back, it all really did happened so fast – just like mother warned. It seemed as if the velocity with which I prided myself would one day catch up with my reality.

That day came in June of 2016.

We had a board meeting scheduled for that Wednesday. I knew exactly what was on the line that afternoon — a raise, perhaps a promotion, but most importantly, validation from the board and extended leadership that I was ‘the guy’ to lead the company to our ambition. The startup adage that ‘not everyone scales’ haunted me throughout my intense preparation for that meeting.

Like a test taker who crammed too hard before the big day, or a marathon runner who trained too hard before the big race, I completely choked in that meeting.

I had participated in over 15 board meetings at Gainsight without issue. However for some reason at this one, with so much on the line, my voice was audibly lower. I mumbled. Responses to questions I knew off the top of my head were replaced by whispers of doubt:

  • Does the board think I’m a fraud?
  • I bet they think I won’t scale and it’s time to bring in a “real” CMO.
  • I didn’t go to Harvard or Stanford like many others in the room. Do I even deserve to be here?

A quick recap with my CEO after the meeting led to a gracious investment by the company into an executive coach to help me hack my thinking. I didn’t want to blow my opportunity and knew I had it in me to do great things for the company, if I would only get my mind out of the way of my ambition.

My coach helped me realize that I’ve got a classic case of what’s called Imposter’s Syndrome, an all-too-common psychological phenomenon amongst high achievers. Imposter’s Syndrome tricks your mind into believing you’re an inadequate and incompetent failure, despite evidence that indicates the contrary. Ultimately, you reject the success that you’ve achieved and live in fear that those around you will have you outed as a fraud and imposter.

As it turns out, Imposter’s Syndrome is rather common amongst those of us working in Silicon Valley. If you can empathize with a story like this, I want you to know that you’re not alone. There are resources available online to those struggling with Imposter’s Syndrome – I’ve found these two books (one, two) to be particularly helpful.

I’ve also found that a few practical tips have helped me in my journey. I’ll admit that like other forms of anxiety, some days are better than others, and we may never fully rid ourselves of Imposter’s Syndrome. I’ve found that a regular practice of the bullets below do help manage symptoms and give me the freedom to bring my ‘A’ game to work every day.

  1. Know that you’re not alone. Once I understood that the feelings I felt were not unique to me, but rather, had a name and were experienced commonly by others, I immediately felt better and realized that this was like any anxiety that could be managed with time. I remind myself of this often when the emotions resurface.
  2. Calm that monkey. One of the books I recommended above describes Buddha’s description of the human mind as being filled with drunken monkeys, all jumping around clamoring for attention. Fear is one of the loudest monkeys, as is the Imposter’s Syndrome monkey that whispers lies to you with hopes you’ll succumb. I resonated with that visual, as it described how in those moments, my thoughts can become sensationalized and get away from me. I read on to discover how to calm that monkey down, which takes me to the next learning.
  3. Find balance in your physical and spiritual life. I never thought I’d be someone who meditates, but as it turns out, the simple practice of finding the stillness in life can quiet the voices of fear, anxiety, worry and other negative emotions. There are great mobile apps that can help with this – I’ve used both Headspace and Simply Being. Within my spiritual life, I use that same opportunity in the quiet of morning to also pray and reflect on Scripture. You see, the busyness of life is effectively monkey food, feeding the negative voices within and fueling Imposter’s Syndrome. Have you ever felt like you were going through the motions, or perhaps a slave to your Google Calendar? It’s those days or weeks that I feel the effects of Imposter’s Syndrome most.
  4. Make small, regular commitments you can keep. The commitment to start every day in meditation or in the gym sounds overwhelming, especially if you’re already struggling to enforce boundaries between your work and personal life. The advice I received was to start small and build as appropriate – 5 minutes a day? Getting into the gym twice a week? Write the goal down, place it somewhere visible, and challenge yourself to increase frequency or duration as you knock down them down.

You’ll come across many books, blogs and media outlets covering what it takes to become successful in Silicon Valley. If you’re like me, you’ll read the content from these so-called-experts and try to implement much of the advice, allowing what others define as success to challenge your own personal definition.

Well I’ve resolved to stop doing that, to take the advice of others as input and not judgment, and to live a more intentional life both inside and outside of the office. My CEO, Nick Mehta, said it best: “it’s just a job.” Perhaps an ironic statement for a CEO to make, but a message that unlocks so much freedom to create, to try/fail/learn/apply, and to be present in our time inside and outside the office without expectation of validation or judgment.

I eventually got that promotion, and with a refreshed perspective, can feel that same degree of optimism in Palo Alto today as I did in 2009.

Perhaps my mother saw coming what I could not…

Anthony Kennada

Anthony Kennada is Chief Marketing Officer at Gainsight, building and leading the Customer Success Management industry. He is passionate about creating new market categories, scaling thought leadership programs, and (obviously) customer-centric marketing. Prior companies include Box, LiveOffice and Symantec.

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