I spend a lot of time talking to younger people about their careers. As many have said previously, being a mentor isn’t just a good way to help others, but to gain personal insights as well. I’ve been reflecting on this dynamic because my niece, who is 26, is embarking on a new and exciting challenge in her life, and she and I have had countless conversations about jobs, career and personal development these past four years. And when I look at the young woman she’s become, and how much she’s grown both personally and professionally, I feel very proud of her. But what I’m most proud of aren’t her career achievements, or her willingness to brave great uncertainty by taking a job with the Peace Corps working for an NGO deep in the Amazon, but how she’s been able to build her esteem and self-confidence while embarking on the path of self-awareness which necessarily entails discomfort and, sometimes, pain. And having a front-row seat to witness her growth, and being a participant along the way, has caused me to check my internal state to see all that I have learned through her process. In reality, it has really been our process.

After taking a big step back and looking at the common threads across all of our conversations, there is a single point that keeps coming up again and again and again: authenticity. What I mean by this is being real, being comfortable in your own skin, being your one true self, in every context. It has taken me my entire lifetime to approach this ideal, but let me tell you, I’m certainly not there and likely never will be. But there is a degree of peace and simplicity that accompanies only needing to be one of you, without different facades, personalities or masks. It is hard to be this way because, quite frankly, it leaves you vulnerable to people not liking what they see, and if that’s really you, well, that can be pretty uncomfortable. In essence, it requires you to be “comfortable with being uncomfortable”, something I’ve mentioned to many a startup founder on the cusp of an important decision where they need to be decisive and give up alternatives, otherwise they will never know the power of laser focus and full commitment. Being truly authentic means embracing discomfort because it is impossible to be liked by everyone, or to have others agree with you all the time, but the most important human to like you is none other than you. And if this is obscured because of the impression that you need to be all things to all people, then how can you really know what your authentic self is?

Whether you are a founder or an investor, a parent or a child, a teacher or a student or simply a human trying to live their best life, applying energy to being intellectually and spiritually honest with others, and, by extension, yourself, brings us closer to true authenticity that can unlock feelings of understanding, empathy and peace.

Written by

managing partner @iaventures. working @thetradedeskinc @transferwise @signifyd @octanelending @memsql @robinhealthco @ethyca_. alumnus @UMich @Columbia_Biz

Get the Medium app

A button that says 'Download on the App Store', and if clicked it will lead you to the iOS App store
A button that says 'Get it on, Google Play', and if clicked it will lead you to the Google Play store