Startup Island and What Making Friends Can Teach You About Authenticity

In the startup world you hear the word authenticity a lot. It’s often said in the context of your personal brand and how you present yourself to investors, it’s talked about when discussing the origin of your company or product, it comes up when we talk about joining accelerators, incubators, developing your company culture and joining business societies. I like to think that I had been on my journey towards authenticity for a couple months before flying to Costa Rica, but what I learned during my last spring break week at this amazing resort in the middle of the rainforest was life changing. I was finally able to see what happens when you’re able to be yourself.

By the time I made it to Costa Rica I had had my startup for roughly a year. Within that year and a bit before I had gotten involved in as many entrepreneurship organizations as I possibly could looking for a community. From a scholars program, to Collegiate Entrepreneurs Organization (CEO), to a local accelerator, to a coworking space, to a business society to a Startup community board, an incubator, a national cohort of Future Founders, and the community of Startup Weekend organizers nothing had ever made me feel like what mattered was who I was and how being my true self and following my true purpose could move me forward more than anything else ever could.

At Startup Island I felt like what mattered was who I was and not what I did. For the very first time I felt like my value wasn’t based on my grades, attractiveness level, intelligence or in how cool my startup was. It felt like all that mattered was who I was and what I wanted. Being in the middle of the rainforest surrounded by so many people who were so willing to be open and vulnerable, I felt like I genuinely didn’t have the time to filter my thoughts, or decide strategically how much it was okay to share about myself. I instinctively knew that the cognitive dissonance of not doing what came naturally would be too much to handle.

When you are surrounded by so many things that are organic you’d have to try hard to be different. From the fruits you eat in the morning, to the water you swim in, to the giggles you hear as you do yoga in the morning everything is organic, everything is natural. The organic nature of that experience is powerful in a way that is hard to grasp. In fact I remember how funny it was when one of my friends, and veteran Startup Islander, Brian decided that one of the first things he should tell me about was how awesome the pineapples were in Costa Rica. I mean, he wasn’t wrong. The taste of everything we ate did feel more potent. There the fruits grow because that’s just the natural cycle of life. There is no pressure and no engineering to make the fruits brighter, or bigger so that they would appeal easily to whatever random person wanted to buy it. The essence and the taste of the fruit aren’t sacrificed for a shiny, big exterior. And very similarly that’s how we grew in this trip. None of the growth we did came with the pressure of being the best or the most impressive. It didn’t come from having something to put on a resume. We grew because you grow when the conditions are good. And believe me, the conditions were great. Thinking about that throughout the trip made me develop the funny habit of sitting at the bar by the pool and ordering a mango. You might be thinking “You mean a mango drink? A mango smoothie maybe?” No, just a mango. Raw, messy to eat, hard to cut through, as real as they come.

When I was able to be my authentic self (as messy as that could be) I was able to attract and truly connect with everyone around me. These connections weren’t made out of strategic alliances, obligation or pressure to be friends. They happened because when you show who you really are you attract people who you’d really like and vice versa.

When I made those friends I realized exactly what I want my connections to feel like from now on. I don’t want my connections to be “ties.” Ties have a length limit. Add pressure or stress and their integrity can be compromised. A tie is limiting, it breaks. It implies that there are two individuals and something that needs to bind them together for them to remain connected. In a connection I don’t want to be an object at one extreme of a rope, I want to be one of two magnets. I want that connection to come naturally and result from the attraction that our essences naturally create. This is what authenticity and authentic connections feel like. With people, with interests, with places. In this experience I learned that embracing who I was is what gave me the confidence to not fear it, if the things I say and create are very much me. The friendships I made in Startup Island made me more sure that who I am is good and valuable even when I fail. I am eternally grateful to be a part of a community that is ready to embrace you for you.

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