Inspiring a future of work that celebrates nonlinear paths

Kaylee Schwitzer Yarrow
The Onswell
Published in
6 min readFeb 1, 2021

For generations, the road to a successful career has looked the same: Choose a path, become an expert, move up the ladder. But, for many of us the thought of doing the same thing forever not only sounds uninspiring and dull, it also seems increasingly unrealistic and irresponsible in today’s rapidly evolving world. So, why are we still expected to specialize and achieve at the highest level at such an early age? And why is there still so little support for experienced professionals who want to shift careers and grow in new directions?

In a world where the playing field is changing on a daily basis, we can no longer assume that the first path we choose will be our forever path. We need a more flexible approach that will prepare us to adapt to the changing needs of the times and reinvent ourselves multiple time throughout our careers. We need to invest in developing generalists who will bring a range of skillsets and diverse backgrounds to the complex challenges of the tomorrow. It’s time to flip century-old paradigm for how choose, grow and evolve our careers on its head.

Few experiences illustrate the high demands of early specialization in the U.S. better than the commitment and sacrifices made by college athletes.

A generalist in a hyper-specialized world

As a student, I always struggled with the pressure to specialize at such a young age. I enjoyed playing multiple sports, participating in different extracurriculars and learning about a range of topics. But, the world around me didn’t seem to care that the range of activities in my life made be feel energized and alive. If you want to do well in life, the world said, you must choose. Choose a sport. Choose a major. Choose a lifelong career path. Unfortunately, the pressure to ignore where my interests were pulling me and choose a single path with next to no information or experience to inform the decision had all but extinguished the curiosity that burned inside of me. The world went from a playground of endless possibility to one that was rigid and narrow. With no room to experiment or fail, I felt directionless and lost. By my junior year of college, I was depressed.

I was staring down graduation and still had no idea what I was going to do with my life. A gap year where I could explore different paths in the real world felt like the only option. So, that’s what I did. I took a break from school and spent a year trying new things, experimenting with different careers and immersing myself in new communities of people. I took a range of alternative education courses, learned new skills and applied them while working on a number of freelance projects with early stage startups. And it worked. Not only had I discovered a passion for building a better world through design, I had developed the experience, skills and network I needed to confidently launch a career in the field.

A collection of images from the time I spent exploring and immersing myself in the tech world

Almost seven years later, I had successfully carved a space for myself in the design world. And while I still believed wholeheartedly in the power of design, I’d been tackling the same kinds of problems for years and frankly, I was bored. As a lifelong generalist, I was itching for a new challenge. But once again, I didn’t know what I wanted to do next or how to figure it out. I looked to the people around me for inspiration only to discover that most of my peers — including some of the brightest, most talented people I knew — were also struggling to find their way.

I began to wonder why shifting careers is so hard.

I wanted to understand the conditions in our society that had resulted in nearly 85% of the global workforce staying in unfulfilling jobs (in some cases for years) with seemingly nowhere else to go. I set out to understand what was really driving the burnout epidemic. I wanted to figure out what it would take to build a workplace where people and businesses would be able to grow and thrive together. I cared because I had seen firsthand the impact that being unhappy at work had on my mental and physical health. I wanted answers. For myself. For my peers. For society. There had to be a better way to do this whole work thing.

  • Where are you supposed to go when you know you want to do something different, but you don’t know what you want to do?
  • Why are there so few pathways for experienced professionals to shift careers and repurpose their experiences?
  • Why is our culture so obsessed with early specialization?
  • Are we really preparing our young people to build a meaningful career and thrive in the workplace?
  • How has the modern workplace left so many smart people who want to do impactful work feeling so dejected in its wake?
  • Are businesses poised for future growth if they continue to demand loyalty to jobs instead of loyalty to their companies?

It didn’t take long before I was pouring myself into academic papers, scientific studies and non-fiction books. I interviewed dozens of people who have successfully shifted careers and others who were still stuck. I met with psychologists and career coaches. I spoke with hiring managers, HR professionals, EdTech entrepreneurs and Future of Work thought leaders. The more smart people I brought in to throw their brains against the problem, the more confident I felt that we were on to something big.

It’s time to support the change makers.

I am excited to introduce a project that I am working on as a Fellow in the Day One Accelerator Program. Founded on the belief that nonlinear paths should be celebrated, The Onswell is a new platform for career experimentation. Unlike coaching services and bootcamps, we create pathways to new careers by connecting mid-career professionals with opportunities to experience new paths, learn by doing and grow their network. We help experienced professionals design their own career experiments and connect them with short-term projects with real organizations that simulate the day-to-day realities of working in a new field.

We believe the modern career is no longer a race to the top, but a lifelong journey of trying new things. Our vision for the future is a more dynamic, human-centered workplace where smart people are empowered to shift in new directions and contribute their unique expertise to a wide range of complex challenges. We believe a world that nurtures human curiosity by celebrating diverse experiences and backgrounds is a world with more creative, dynamic and energized people who are better prepared for the future of work and more fulfilled in life.

This is just the beginning.

Building a future of work that celebrates nonlinear paths is going to require all of us — individuals, businesses and educators — to come together and fundamentally rethink the way we approach our professional growth and development. Together, we can build a workplace that nurtures human curiosity. A workplace without burnout. A workplace where people and businesses reach their full potential, together.

Get started today and inspire your next transition by following us @theonswell on Instagram. Connect with a community of likeminded peers and be the first to know about our upcoming events and opportunities.

Stay tuned. There is so much more yet to come.

xx

Kaylee Yarrow
Founder of The Onswell 🤙🏽

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Kaylee Schwitzer Yarrow
The Onswell

Founder at The Onswell, Lead Designer in New Strategic Initiatives at Verizon.