Analisa Winther - Designing your life for success: the art of being comfortably uncomfortable

I have a theory. If you surround yourself with people who make you comfortably uncomfortable, you can design a life where opportunity finds you. Being comfortably uncomfortable occurs when you honor your values while being open to people, perspectives, and interactions that challenge your assumptions. By immersing yourself in such situations, you create an environment that encourages serendipity and unexpected growth on both a professional and personal level.

Let me illustrate.

I go to work everyday at DARE2mansion, an auto-body repair shop turned startup co-working space designed to be a home of opportunity. Each day, the Mansion is filled with a diverse group of entrepreneurs and intrapreneurs who are creating scalable positive impact. We have entrepreneurs doing virtual reality, music tech, jewelry on demand, parkour, upcycled art, SaaS, sharing economy, and so much more. This diversity in industry may seem random, but it is deliberate. DARE2mansion recognizes that if I sit with people working in the same vertical as me, we can empathize to a point, but it won’t be long before the overlap in our experiences no longer benefits me. We learn the most from being with people who hold a different skill set, network, or ideas from us. This is especially true in entrepreneurship where each day is filled with hard problems and creative thinking is essential for finding viable solutions. 

This same notion extends into my home life. I live in Nest, one of the world’s largest non-profit co-living spaces for entrepreneurs in the heart of Copenhagen. My 20 roommates are coders, designers, fundraisers, engineers, community builders, data scientists, hustlers, professors, CEOs, economists, marketers - the list goes on. Together we have 152 years of entrepreneurial experience across 134 startups. Odds are good that if I have a challenge on a personal or professional level, someone in Nest has dealt with it before and is more than willing to provide advice to see me through. It’s a community of people who want to see each other succeed and dare one another to think big, go after my dreams, and be honest about how good or bad things are. Entrepreneurship is a roller coaster and it’s proved invaluable time and time again to be around people who understand the ride.

The benefits I experience from working and living with people different from myself, also apply digitally. If we beat the bias of the algorithms on social networks, we can have incredible feeds of content, which energize us and provide us with new perspectives, ideas, and connections - not just alternative facts and fake news. I’m the lucky member of a variety of active Facebook groups such as Singularity University, Nest alumni, Danske Ideer and StartingBloc Fellows, which provide access to a wealth of information. Every time I log on, I am overwhelmed with the beauty of people connecting with each other, sharing phenomenal opportunities, lending a helping hand and collaborating on initiatives from every corner of the globe. This is especially important so see and remember these days.


The Power is in the Room

I can be easy to forget how much power we have to design a life full of interactions, which encourage our success. If you let them, the people you surround yourself with on a daily basis can have a profound ability to positively impact and foster your development on a personal and professional level. 

DARE2mansion, Nest, and these online circles share the common denominator of attracting people with entrepreneurial spirits who want to make the world a better place. While how they create change varies greatly, everyone is united around daring to do the impossible, genuinely caring about each others’ success (and sanity), and a willingness to help by sharing whatever they can give or pitch in.


Let the world do a little work for you

These communities have opened me up and accelerated my ability to reach a solution by not being afraid to ask for help or be vulnerable. I see myself pushing my limits in all kinds of ways and experiencing new things I never would have attempted on my own. They listen to me. They lift me. The impact they bring isn't always obvious, but it's inevitable - serendipitously occurring through stories, reflections, discussions, and confessions told over late night conversations, long meals, and simple passing bys in the hallway. 

While your recipe for being comfortably uncomfortable may be different than mine, I challenge you to think about how you have designed your life. Do your personal, professional, and digital circles provide diversity in skills, thoughts, and experiences? Are you surrounded by people who want to see you succeed and positively challenge you to grow? Are you living your values? Perhaps it’s time you took an active chance and designed your life to be comfortably uncomfortable too.


Analisa Winther is the Director of Innovation and Community at DARE2, an award winning innovation bureau that inspires, enables, and connects people to create scalable positive impact. She is the Program Director of the early stage accelerator thinkubator and facilitates the community at the innovation hub DARE2mansion. She is also the Chairman of Nest Copenhagen, a non-profit co-living space for entrepreneurs. Analisa is a sought after speaker and facilitator. She has a Msc in Management of Innovation and Business Development, minor in Neuroscience, Economics, and Psychology.