Creative disruption facilitates transformational doing

11 min readFeb 26, 2016

by Regina Jackson, President & CEO

Nov 19, 2014, I was on retreat with other CEOs to discuss the “college bound brotherhood initiative”, a subsidiary of President Obama’s “my brother’s keeper” initiative. Being that it was a particularly gloomy day, I was glad to feel the soothing warmth of a crackling fire as we entered the dining area. The strategic planning sessions had sapped my energy and my hunger level had risen to that of a starving hyena. Just as I grabbed a plate, my phone rang. The conversation was a blur, I assume I was in shock because I can’t remember what was said or what i said. An overwhelming wave of Excitement, Joy and relief came rushing forth. O2 initiatives had just awarded me a 3 month sabbatical.

For weeks, I day dreamed about what i would i see, what i would taste, what i would feel… What I knew for certain is that total separation was the key to me achieving total relaxation from this job that I both live and breathe. For me there was only one route to achieve this personal nirvana, put an ocean between me and the work.

My first thought, dust off the ol’ bucket list. AFRICA. I wanted to climb the tallest mountain, lookout, and see where we all came from. Then safari, for a long time I’ve been enamored with scenes of elephants, giraffes and zebras grazing on the plains. I get lost in visions of large prides of lions, leopards eating in the trees and the many intoxicating sounds, sights and smells of Africa, land of my ancestors. Next on to Turkey, being another land of my ancestral origins i was fascinated with Turkish history especially that of the city once called Constantinople. (Istanbul) I looked up pictures of the resplendent Grand Bazaar I’d heard so much about and grew impatient to see it in person. Thirty years ago, a trip I had scheduled to Greece was cancelled due to security concerns, I’d always regretted not rescheduling that trip. Now was my chance to rectify that mistake. On the way back i’d visit Caribbean Islands like St. Marteen and St. Bart’s to bask in the sun and soak in the incredible colors, flavors, and customs of various beautiful island cultures. A vision of yoga on the beach, gave me a great feeling of relaxation, wellness and calm. In my head I’d already made the trip.

I have dedicated every minute of the last 22 years to a mission of righteousness, the advancement of all youth through education, brother/sisterhood, and the expansion of their citadel of personal evolution, the East Oakland Youth Development Center (EOYDC). At first, the idea of a 3 month disconnect seemed impossible. My life was so intertwined with my work, how could I abandon my purpose? We’d just finished remodeling our EOYDC building. For the first time in 2 years we were operating in our own house. How could I leave now when so much was taking off? I didn’t want to miss our next class of aces embrace the skies. It took comments like “you deserve this”, “this is big” and “take care of yourself, we got this”, from parents, students and staff to bring my head out of the clouds and realize that I NEED THIS BREAK! After all this was an opportunity of a lifetime.

Dreams in Action
Literally my entire life, I’ve dreamt of Cuba. As a young girl, I’d imagine a vibrant island world. I could see colors dancing off the buildings as the music filled the streets, warm smiles at every corner, and oh my goodness, the food! Being that access to this jewel of the Caribbean was restricted since the year before I was born, there was little more I could do than create my own Cuban alternate reality. Now, decades later I’ve literally made my dreams come true. At last, I could immerse myself in the true beauty of this inspiring, spicy island. Whether I was riding in the1960 Pink Cadillac’s, visiting the art festivals and museums or witnessing architectural brilliance, I was swept into another time. I was challenged to match history with the power of now and a hope filled vision of the future. I celebrated my birthday at Floridita, the famous tavern Ernest Hemingway frequented during his time on the island. This place reeked of his essence. In fact, there is a pewter statue of the legendary author located at the end of the bar. Even though alcohol is not my cup of tea, I felt the urge to sample the signature drink, the Hemingway Daiquiri, which wasn’t half bad. From my ever improving grasp of the Spanish language, learning of Che’s Motorcycle Diaries and witnessing the progress of the relationship between our 2 great nations I left Cuba with my head enlightened and my spirit transformed.

Much like Cuba, my journey to Tanzania was steeped in a mission of personal glory spurred on by a lifelong fascination. A jubilant anxiety coursed through my body during the entire 22 hour flight. Upon arriving at Arusha Airport I was greeted by my personal guide John, a kind, well groomed, stocky man with a genuine love and knowledge for the mountain that will forever go unrivaled in my eyes. We had a very rough ride back from the airport, the locals referred to the route we took as earthquake road. However my discomfort faded early on in the drive as my eyes laid upon a sight I had craved for decades, Mount Kilimanjaro shining like a diamond in the African sun. Soon I was to climb the highest peak in all of Africa. A while later, we approached Ilboru Safari Lodge where I would enjoy a siesta before meeting my fellow crew members to review of our 7 day journey. With me included, we were a crew of 9. Being that my peers were all generally around 25 years younger than me, I knew it would take every ounce of my being to scale this beast of a mountain. I was determined now more than ever to see this through.

Our first destination was located through the pristine Montana rainforest, emphasis on the word “rain”. Naturally I had forgotten my rainwear, so instead of taking pity on me, mother nature sent a constant downpour to accompany us all the way to the first stop. A natural paradise, free of litter and full of life, this was where the climb began. We started at 6,000 ft elevation but reached 10,000 ft by days end. By then I was of course drenched. We learned about the Kilimanjaro history and vegetation. I was impressed to learn 55,000 people attempt the climb each year. I met climbers from Australia, the Czech Republic, France, Ireland, Japan and of course the United States. Sadly with the exception of a Nigerian couple, I was the sole climber of African descent , I was troubled when John divulged that he had only 15 black guests in his 237 treks up the mountain, the fact that the brotha kept count showed me this fact troubled him too. By day 3 I was one of the many documented climbers of Mount Kilimanjaro since 1887. Rock climbing through a relentless onslaught of rain and altitude sickness, I willed my 53 year old behind all the way up to Lava Tower. At an elevation of 15,500 ft, I felt I’d achieved my goal. A song rang out; it was my group singing in honor of my accomplishment. As it began to snow, we sat down to a meal of zucchini soup, rice and plantains, it tasted like victory.

With echoes of swahili terms such as “jambo” and “pow lee” still fresh in my ear, i turned my sights toward a 77,000 acre wetland safari in Botswana called Duba Plains. It was to become a 4 day personal sanctuary. I only had 4 days here so I was up at 5am into the bush by 530 every morning. My days were full of majestic scenes of wildlife at every point.

Giraffes welcomed me from slumber at sunrise; I ate lunch with the hippos and watched sunsets with the elephants. My last night, a huge thunderstorm woke me out of my sleep at 3am. The earth rumbled beneath me, i felt as though my tent might sail away as it was pelted by heavy rain drops, bright flashes of light, and aggressive gusts of wind. After 30 minutes, the storm subsided and the tranquil sounds of the African wilderness restored the calm ambience.

With Africa still fresh in my heart, I headed up to Istanbul, Turkey. Coming off of my safari, the cold air was a shock to my system. The differences between these places were many but the weather drew the sharpest contrast. By changing hemispheres, I went from an African summer to a Eurasian winter in less than 24 hrs. I was reminded of China by the thousands of people moving through the city. When I arrived at my hotel I was surprised that there was a security check for admittance, I was quickly reminded of how much we as Americans take our safety and comfort for granted. Reeling excitement and wonder. Immediately, I joined a tour toward the Asian side of the city, taking in the beauty of a city betwixt two continents. Taste testing Apple tea and Baklava inside the Bazaar was europheric, a welcome respite from hours of shopping. I was in awe. On tour to the Blue Mosque, never had I seen, such beauty, such art and architectural genius laid out over square miles, at that moment I knew I had to bring back a substantial souvenir to commemorate my time here. I purchased a rug shortly before visiting the home of my guide to Istanbul. We feasted on lamb, rice and a “turkish favorite” made with yogurt, cucumber and herbs called Cacick.

On to the Mediterranean utopia called Santorini. Born of the remnants of the great minion eruption 3600 years ago, diverse vegetation, and white capped villas spread over beautiful cliffs surrounded by true blue seas. I was eager to try the cuisine and was pleasantly surprised to find that Greek omelets, and yogurts, were already a staple in my diet, whether home or abroad, my mouth watered with the enthusiasm of Homer Simpson at the sight of a good omelet. Wizzing across the sea, we visited sulphur waters that hugged the rock surrounding Thera Volcano which created Crete. Streets were almost empty, it was low season, but the quiet allowed for much better exploration and relaxation. A 14 hour layover in Dubai allowed me to visit the 7 star City and pride of the United Arab Emirates where architectural brilliance once again took my breath away.

Caribbean Soul Searching
Question: It is 85 degrees in January, where am I? Answer: On one two or three of the chain of 700 Caribbean Islands. I awaken to an ocean of blue skies, walk slowly through rose and shell beaches letting the water and sand envelop my feet. I took boat rides to uncharted islands, and wallowed in the flavors of island delicacies like lobster, steamed red snapper and ginger beer. This is paradise. I’ve replaced the R in my name, it now stands for relaxation. I spend timeless hours just watching waves crash, dazzled by the sun as it glistens off the sea, viewing magical sunsets and mesmerized by the variations of blue in the water. On a non-beach day I visited the Lotterei Farm’s “So Fly Zone”, a natural filled conservatory. I experienced the whimsical “Tarzanian” excitement of flying from one tree to the next through Zip lining. Tight rope walking and other physical agility tests were in store on this amazing obstacle course. Visits to ports, marketplaces, carnival and festivals, filled my days and nights. Fast ferry’s facilitated daily access to islands nearby like St. Bart’s, Anguilla and Harbour Island in Bahamas. Given this backdrop of beauty my mind would drift as in a dream space. Personal friends in Bahamas looked after me as my travel portion came to an end. They shared delectable food stops, upscale movie sites, and secret shopping haven. My loving friends gave me comfort, encouragement and reminders of the most important things, time with friends and love ones. From here I returned home to round out my masterpiece of a journey.

Getting “my house” in order
Creative Disruption became a vehicle traveling 30,000 miles, through 3 continents, and 22 airports, taking in the graceful views of mountains, volcanoes, animals, oceans and everything in between. My strategy included being adventurous in month one, resting and relaxing soul searching in month two in order to spend my third month in reflection and framing my vision forward. These excursions turned what i once thought unfathomable to attainable. I witnessed my dreams morph from fantasy to actuality in one fell swoop.

Now that I am back home, organizing the clutter that enveloped my personal space, I have moved my laptop from my bed back to its desk. My cell phone has a new home away from my hip. This time away has helped me reshape how i want to live moving forward in order to become my best me. I now know that taking care of the organization I love starts with ensuring that my mental and personal welfare are prioritized. Morning walks, fruits and vegetables have returned to my daily habits. Naps are a newfound discovery. Life was creatively disrupted and I will never be the same, I will be better. Thanks 02 Initiatives! Thanks to my amazing staff and board for allowing me this extraordinary respite, I am the luckiest CEO in the world!