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How I Thrived in the Gray Zone: Three Ways to Win in the New Age of Work

From an early age we’re taught to focus on the outcome. Did you win the game? Ace the test? Get that raise?

It’s ingrained in our core that the outcome is a far better indicator of success than living in and measuring the process itself. We’ve seen this methodology applied time and time again. From No Child Left Behind to valuations on rising startups, these scenarios force the parties at play to hit metrics in order to advance to the next level.

But in a world where economies and power are shifting, and the path forward in achieving that arbitrary next level is blurred, we need to figure out a new way to navigate this gray zone. We must learn to thrive in today’s constantly shifting society and relish in the process of learning, of iterating each day.

Photo by Tyler Iastovich

Since founding Cureate Connect, I’ve had to reflect and grapple with what success means to me. Everyone has different dreams and goals in life, yet we’re all familiar with the “success story.” Can we begin to untangle ourselves from what’s been beaten into our psyches about achieving outcomes and instead live each day through our values — seeing that as a “win”?

Here are three ways I’ve learned to embrace the gray zone in this new age of work:

1) Picture yourself bowling. You holding the ball is the beginning of your life, and the pins are at the end. You roll the ball and it’s a crap shoot. Maybe you end up in the gutter, maybe you hit a strike. But… what if you had bumpers? Even if it takes you longer than you’d like to get down that lane, and you’re constantly ricocheting back-and-forth, eventually you will hit the pins at the end and, more importantly, you won’t end up in the gutters. What if those bumpers were your values that you stood by every day? No matter how you got to the end, it doesn’t matter. Because every day you’re still living a life within the value parameters that you’ve set.

2) The post-WWII societal structures we have created support a drastically different landscape than that of today’s workforce. Certain givens of the American Dream no longer apply for many of us. No 401K matching, very little to no employee sponsored health care, a stock market that we’ve seen fail us and our families in big ways. We’ve seen it coming. Nearly 5 years ago, it was reported that by 2020, 40% of American workforce will be freelance employees. Without the guarantees of pensions, and dare I say, retirement at all — we can’t be keeping time like our parents did. This sense of time that is divided like the generations before (e.g. year 25: get married, have kids; year 60: retire) is obsolete. Instead, grant yourself 100 years. If you have 100 years on this earth to make a statement, to extole your purpose, what will you do with that time? If you don’t make it onto someone’s 30 under 30 list, who cares? You literally have 70 more years to make a sizeable impact on this world.

3) None of the above was learned in a textbook or class. I gleaned them through thoughtful conversations with close friends (see: “4 Ways to Startup Your Ambitions” by my good friend Allie Armitage) and acquaintances over the years. One of the keys to success is being able to walk into a room and strike up conversation with anyone in there. In order to do that, you must be knowledgeable about a variety of topics, you must have an open mind, and you must be willing to learn. I surround myself with people who have differing points of view — based on their profession, race, gender, age, where they grew up, religion, political beliefs, etc. There is no way you can be a citizen of the future without empathy and understanding.

Unfortunately our society has not caught up yet to the changed landscape. We still deal with external pressures to perform by a certain date, and to judge our lives based on outcomes. Our current political and media arguments may make it seem very black and white, but we’ve entered the gray zone. With these three best practices, you can navigate unforeseen challenges. Embrace your values, and stand strong in knowing that you do have purpose. Realize that you have time to achieve that purpose. And, always remember to surround yourself with people who exude empathy and understanding.




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Kim Bryden

Kim Bryden

Kim Bryden is the CEO of Cureate & Cureate Connect ( On a mission to create more interconnected vibrant communities via food/beverage.

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