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SOTW: The Most Uncomfortable Key to Your Success with Woken

Every week, the NYU Entrepreneurial Institute elects a Startup of the Week. We then invite the founders of these startups to share a blog post with our community. These posts can be inspirational, educational, or entertaining. Founders can share founding stories, resources, lessons, or anything else they want.

This blog post was written by Rachel Serwetz (Stern '20), founder of WOKEN, and originally posted on Medium

WOKEN is a career exploration platform helping professionals to confidently identify which career path they will love. They guide professionals through a step by step process of learning and reflection to ensure their clients reach a point of clarity, confidence, and excitement in their career direction. Currently, they're crowdfunding to continue to build out their platform and achieve their mission – reminding people they can and should find a job they love. 


Uncertainty is arguably the most uncomfortable feeling that we humans experience and despise. However, it may just be the most critical thing to your success.

At Fast Company’s Innovation Festival, incredible speakers took to the stage and I was struck by how often this theme came up.

Interestingly enough, leaders in the media and entertainment industry spoke about embracing uncertainty often. Brian Grazer, Imagine Entertainment’s Cofounder, spoke about taking a leap of faith when starting new projects. These projects are no small investment, and yet these leaders learned from experience that there are certain things you can and should be thoughtful about in a media project, but at the same time, it has to feel like the risk is worth taking. They recognized that there would be a lot they wouldn’t know about how the film or project would pan out but that is precisely what allowed the beauty to unfold. Enabling that freedom led to successful works of art.

We heard Pharrell Williams speak about growing in one’s career solely by enduring the experiences when he felt uncomfortable. For any of us who look at Pharrell today, you may never guess that he feels fear or uncertainty, but he was sure to tell us that there were several points in his career that he very much felt that way, and those moments are what led to very successful projects. He mentioned “being delusional enough to trust someone else and yourself.” Pharrell found a mentor that understood his industry, understood him, and he knew that Chris Meledandri had his best interest in mind. He trusted Chris on projects like The Grinch and it pushed Pharrell to new heights. He spoke of doing many future projects where his fate would be in Chris’ hands.

Embracing uncertainty clearly relates to the startup world, where founders undertake a major risk to try to make their vision into a reality, without knowing exactly how they’ll get there, or if they will at all. Despite knowing there is a huge chance of failure, taking a risk allows founders to test their ability to learn and grow. This very risk-taking is the only thing opening up the founder to see whether their idea can in fact become a reality. In this instance, embracing the unknown is in fact required for a founder to see whether something even more beautiful can result.

Beyond this, embracing uncertainty relates to one’s career in general. We often want to cling to choices that seem familiar or popular. As a career coach, I see young adults choosing careers for these reasons, when this could be the most debilitating time to think along these lines. My coaching process always begins with eradicating one’s current idea of what they think they want. Starting from a place of, “I don’t know” frees us to open ourselves up to finding what truly makes sense down the road.

Uncertainty is scary. But if you think to yourself, “What concrete steps can I take to handle this uncertainty?”, you’ll likely find there are practical things you can do to achieve your goal without undercutting your values.

  1. Ask yourself deep down what you know to be true. If you’re clinging to an answer you know isn’t what you truly want, take and breath and release it. The quicker you do, the quicker you open yourself up to a brighter potential.
  2. Often, I rely on learning as a way to handle my uncertainty. I love to learn from others as as way to fill in the gaps of what I’m not sure of.
  3. Remember you aren’t alone! We all face uncertainty at various points in our lives and careers. Turn to your network, mentors or peers to bounce ideas off of. Having a sounding board or a coach can help immensely to help us reduce our fear and make progress towards our goal.
  4. Think about what the worst possible outcome could be if you embraced your uncertainty or your fear. Feel free to plan for that potential so you feel better about taking a leap of faith.

Don’t make the quick, easy choice simply because it’s easy; it will only backfire. Often, what we fear most is precisely the thing we know we must do. So, embrace your discomfort, apply logic and learning, reflect on this new information, and see what may blossom. Only then can we find what we didn’t even know what we were looking for.

What are your thoughts? Let me know: rachelserwetz@gmail.com

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