Truth or Dare?!

“I dare you to do it!”  The summer sun beats down and shimmers on the water.  My eyes sting with the glare, but I do not blink. I focus intently on a wooden handle dangling about 18 to 24” out of my reach.  From where I stand on the branch of the tree next to the pond, I am about 12 feet off the ground. My bare feet struggle for solid footing on the branch.  I feel the fear rising up in my gut. My breath quickens. Adrenaline courses through my body as I stare at the water, willing the courage to come. I pause briefly and feel a slight breeze cool the sweat on the back of my neck.  I take a deep breath, let go of my thoughts and jump!


You cannot always wait for the perfect time, sometimes you must dare to jump.
— Anonymous


When I was a kid, I loved playing Truth or Dare.  I nearly always took the dare. Taking the dare was sometimes risky, often challenging, and always scary in a shaky knees kinda way.  I loved it because it made me feel bold and courageous. It was exhilarating putting myself out there on the edge, sometimes quite literally.  I will never forget the day I overcame my fear of heights, climbed the tree that grew next to my friend Micki’s pond and jumped out to grab the handle of the zipline her dad had rigged over the water, flinging my nine-year-old self into the watery depths. I was energized for days afterwards.  With my friends and often my sister looking on, I couldn’t hide or lie - I either carried out the dare, or didn’t. In hindsight, I realize that playing Truth or Dare helped me develop tremendous trust and belief in myself as I faced my fears and learned my physical, mental and emotional limits.

Children Trophy Dare To Detour
Dare To Detour Zipline

As I grew up, I set the game Truth or Dare aside, or so I thought.  Today I realize that I unknowingly embraced the mindset I had developed playing the game and applied much of it to how I lived my life in college and beyond.  A turning point for me was pursuing my first job out of college. I dared myself, at the urging of the man I was an intern for at First Interstate Bank in Portland, to get a job in New York City.  For a girl who grew up on a hobby farm in Oregon where she raised sheep for her 4-H project, attended Oregon State University (Go Beavs!) and had never been to NYC (or knew anyone who lived or worked there), this was a big goal.   Yep, a goal so big and hairy and audacious it required a dare to do it. I accepted this self-imposed dare and told everyone I knew about it: my parents, my sister, my 4-H leaders, my sorority sisters, my boyfriend and anyone else who would listen.

I wrote or called nearly 100 companies based in NYC, some reached through introductions from relatives, and woke up early to make cold calls from a closet in my college apartment so I wouldn’t wake my roommates. The rejection rate was close to 100% but I managed to get 5 informational interviews.  I spent spring break my senior year trudging around NYC to the interviews I scraped together, and wouldn’t you know it, out of those 5 informational interviews I got 2 offers?!

I accepted a sales assistant position with Instinet, the first online trading company, teaching old-school OTC traders how to send messages and buy and sell between the spread, all for the first time.  It was 1987, and this online trading technology was brand new. Email as we know it didn’t even exist at that point. Truthfully, I had no clue what I was doing, but I was confident that I would figure it out once I got there.  The first two years in NYC were beyond tough, but I learned more about myself than I did in all four years of college and ultimately lived and worked there for eleven years. I took the dare and never looked back.

Sheryl Ott 1987 Instinet, A Nomura Company
Carnegie Deli NYC Dare To Detour

Fast forward to the year my daughter started middle school.  The all-school community read that fall was Mindset: The New Psychology of Success by Carol S. Dweck, PhD.  Dweck developed the growth mindset theory and in her book explains, “In a growth mindset, people believe that their most basic abilities can be developed through dedication and hard work – brains and talent are just the starting point.  This view creates a love of learning and a resilience that is essential for great accomplishment. Challenges and failures are viewed as opportunities to improve learning and skills.” Reading Dweck’s book, I understood that all those games of Truth or Dare had instilled a growth mindset in me—or what I like to call a "dare mindset".  Moving to NYC after college was a test of this mindset, as was subsequently choosing to step away from my career to become a mother. Being a mom truly tested my dare mentality, and there were many times where I opted to play it safe. But all along I’ve held onto that feeling, that exhilaration that comes from stepping outside my comfort zone and standing out there on the edge taking a dare.  I had to keep it tucked away as other parts of my life demanded priority and my focus. Recently things have shifted just enough for me and I’m reacquainting myself with that feeling.

Do one thing every day that scares you.
— Eleanor Roosevelt

My current dare is this - this blog.  I’m calling it In Cahoots since I need you all in on this with me.  If you’d told me a year ago that I’d be writing a blog I’d have laughed out loud - a real LOL moment, no doubt.  But here I am hanging it all out there, sharing my story with the intention of connecting with a strong, supportive community of like-minded women who are embracing their truth and are willing to take on a dare every now and then, step off their daily paths and shake up their routines to keep it all interesting and the spark alive.  I look forward to getting to know you through In Cahoots, and intend to make it an open forum for us to share.

I’d love to hear about the dares you’ve taken along the way and how they’ve shaped you as women. While I encourage you to be bold and confident, please be kind and supportive when sharing and commenting.  We all have different tolerances for risk, and our dares will look and feel different, as they should. The important thing is to put them out there so we can all stand in support, in cahoots, if you will.  Come on - I dare you!


Sheryl Ott XO Signature Dare To Detour