There’s a Big Difference between Fearless Leadership and Undaunted Leadership — Let Me Explain
7 minute read
Since I announced the publication of my upcoming book, Undaunted: Overcoming Doubts and Doubters, the one question I’ve been asked more times that I can count is: which books inspired you to write your story? And the answer is: every book — and none of them.
I’m an avid reader who tears through at least a book a week, always eager to learn lessons from other entrepreneurs, thought leaders, inspirational voices, and people with compelling life stories. But I’ve never read a book that tells the story of what it takes to build a meaningful career and a thriving business, specifically by overcoming all the obstacles that will undoubtedly block your path.
Undaunted is my story. But it’s not a memoir. It’s not a how-to. It’s not a rulebook for entrepreneurs or a CEO tell-all. What is it? It’s an account of how I overcame those doubts and the doubters to chart an unlikely path to where I am today. Regardless of whether you’re building your own business (large or tiny) or planning your career (maybe a second career?), there’s one thing I can guarantee: you will have to face uncertainties, contrarians, misfortune, and unanticipated adversity along the way. How you lead yourself — and others — through those challenges is what will define you and determine your ultimate success.
That’s what Undaunted Leadership is all about.
I never expected to run my own company. That was never part of my vision. In fact, I didn’t have a specific vision for my career or a clear end goal. Instead, I was drawn to unique challenges. I was attracted to solving problems that didn’t have a set roadmap or established solutions. My north star was always to innovate — looking to pioneer a new means of distribution or a new commerce channel or a new beverage category. And when you try to do something new, what’s the first thing you’re going to hear?
“Can’t be done.”
“That’s been tried.”
“No one’s interested.”
“Move along, sweetie.”
Over the next several weeks, I’ll be writing about what Undaunted Leadership looks like from my perspective, what it’s like to walk in my shoes and face the hurdles I deal with every day. I’ve been a waitress, an executive assistant, a corporate salesperson, a deal-maker, a mom (four times over), an entrepreneur, an inventor, a CEO — and I’ve worn several other hats in between — and each phase of my career has taught me important lessons that I want to share with you.
Finding Your Tribe
I don’t think there’s a more valuable piece of advice to offer people starting out in their career (or considering a career shift). Who is your tribe? We’ll dig more into that in the coming weeks, but it starts with a comfort and a shorthand that you cultivate with certain peers over time. It’s not necessarily about finding people who you get along with or seeking out people who will always agree with you, act like you, or look like you. It’s actually quite the opposite. It’s people with whom you have a foundation of mutual trust so that they can call you out and challenge you when you need it. Those are the people who you will rely on to help you through adversity and level with you with some tough talk.
The Vastly Underestimated Power of Asking a Lot of Questions
I didn’t know everything about running a company when I started Hint (and guess what — I still don’t). Just like I knew practically nothing about magazine circulation when I started my first job at Time Magazine in the late ‘80s. But back then and still today, I’m never afraid to pause, step back, and ask questions. I think it started when I was waiting tables during college. I would always ask people what they did for a living; that was actually a key part of me figuring out what career I wanted to pursue. I used that skill as a salesperson in the ‘90s making endless cold calls to prospective businesses when I was at AOL. Asking questions opens people up, it shows them that you’re interested in their expertise, and that you’re curious about their experiences.
Sensing a “Maybe” and turning it into a “Yes”
My father nailed it for me very early in life. I remember pestering him endlessly about a pair of green pants (with lifesavers printed on them, no less) that he claimed I just didn’t need. He turned to me one day as I again pointed those pants out in the store window display said, “Kara, you always think that ‘no’ means ‘maybe’ and ‘maybe’ means ‘yes!’” Since then, I’ve studied the body language and tone of every boss, colleague, client, investor — whoever I sit across the table from — and look for the right opening to shift them from a doubter to an ally. To me, every problem has some sort of solution, and every dissent has a compelling contrary argument.
Taking the Plunge, Reveling in Risk
Uncertainty is scary. No doubt about it. My husband Theo (aka the COO of Hint) and I put our entire business on the line more than a few times — risking personal assets we had worked for years to build up — in order to build Hint to where it is today. Why did we do it? We both could have taken much safer routes with Silicon Valley jobs that promised far more financial stability. But what those opportunities lacked was the sense of creating something new and life-changing.
Being Undaunted is Addicting
Being comfortable in that space where you don’t know the answers, where you’re up against long odds, where you’re swallowing some uncomfortable truths delivered by the people who know you best — it takes some practice and a lot of perseverance. Those moments can be awkward (at best) and sometimes downright terrifying. That’s what it really comes down to when I talk about being undaunted. It’s finding a place of solace within the unknown, having the confidence that you’ll eventually find the right questions to ask, invent the unseen solution, convince the cynics, or face up to the truth that will unlock the next step forward.
You might have no interest in choosing my path and running your own company (or perhaps you do), but your success in whatever goals you set for your career will rely on your ability to conquer your own fears and overcome those skeptics – and better yet, let their skepticism and your self-doubt motivate you.
So come on this journey with me! You can start by ordering my book which will ship out on October 20th. I’ll also be sharing some of the life lessons I picked up in the last few decades here on LinkedIn, on my podcast, in live Q&As, and in a bunch of upcoming book launch events. We’ll talk about seeking out the kinds of challenges that will test you, inspire you, break you, rebuild you, and drive you to be Undaunted. I’ve said this countless times and I believe it in my bones: If my story proves anything, it’s that if I can do it, you can too.
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