Things Didn't Go As Planned (And That's a Good Thing)

Picture this…a 17 year old, on the cusp of graduating from high school, taking her Mom out for lunch to discuss her ambitions in life. The plan involved fast tracking her profession to be young and powerful. Staying in the city she grew up in to capitalize on her network and influence. Pursuing advanced levels of education following high school. Living the minimalist life in a downtown condo. Marriage….maybe, if it “makes sense”, but no specific dream wedding. No kids. And, awards and recognitions to build her reputation of performance and success.

She was strategic (as she was told to be). She had always been told that there is a path to get to a certain place. She knew she needed to focus to get to where she wanted to be. Take the right courses. Get the grades. Push herself in sports, music, and art.

Although there was no formal guidebook, it seemed to her that if she followed this path, then everything would just work out once she graduated.

This was me. I thought that I could take a straight path to my goals. I was committed to that path. But, all it took was for me to be exposed to the unstructured world of college – the smorgasbord of options and opportunities, a choose your own adventure book for life – to have my vision shaken. And that was really just the beginning.

I could say that everything was positive from the get go, but it actually became more like a game of Snakes and Ladders. One step set me in the right direction, where another choice or unexpected event sent me sliding back, asking questions about where I was going.

My schooling / training was so focused on finding the one right answer. In classes in school, the information was all available to be able to find that right answer. When I completed my work, teachers struggled to find ways to offer enrichment. Very little of the curriculum involved having to seek out the truth, ask your own questions, or fail (and be comfortable with doing so).

We were also made to focus on the outcome rather than the process. How many times in my life was I asked what I wanted to do when I was older, what my vision was for 5 years in the future, and who I was going to be?

However, within a short few years of college, I began to learn that ambiguity was not only inevitable in the “real world”, but also was where true learning and leadership development sat.

I took on initiatives as a student leader – creating programs where there was no clear path of how to push it through the University bureaucracy. I embraced courses that were different (e.g., Latin) or involved more hypothesizing, questioning, and brewing in incomplete information (e.g., case study based coursework and strategy classes).

It started to feel good. It started to feel exciting. It helped me grow.

Additionally, during this time I also reflected on the fact I wasn’t totally programmed from my schooling past. My years of participating in science fairs during elementary, middle and secondary school always had me moving from question to answers with coaching, but not a definitive hand to hold. It helped me learn how to ask and frame questions and work to an answer, discover a solution that is difficult to find, and discern data and information. I volunteered and took on youth leadership roles, learned how to bootstrap, how to fundraise advocate for a cause, and really get creative in order to do some good. Making myself uncomfortable was how I truly began to grow the most.

I was lucky. I can’t take all the credit though. I had family, mentors and professors that encouraged me to be mindful about my experience. They pushed me to gain perspective from bumps in the road – academic, personal, health-wise, and social.

So, why do I share this story? I know it isn’t unique. But, it does make me worry. The ability to handle and embrace ambiguity is critical to learning, growing, and becoming strong leaders. But, I’m not sure our world is equipped to create people resilient to the unknown, particularly as ambiguity and change becomes more of the norm.

Change is the only certainty in this world today and thus so is ambiguity about the future. Every day that passes we need to deal with an increasing amount of the unknown. Ambiguity creates complexity and makes decision-making difficult. Ambiguity creates uncertainty and stress. There is a reason that people either struggle or thrive in a world of ambiguity.

The book “Nonsense: The Power of Not Knowing”, is one source that speaks to our human tendency and preference towards certainty, highlighting the voluminous research into both its upsides and downsides. However, it suggests that rather than get rid of ambiguity, we engage with it. With that we can make better decisions, we can be more creative, and we can even be a little more empathetic. To me, this calls for an imperative to create environments and systems that allow us to better engage rather than avoid ambiguity.

And, it appears that we are more frequently seeing the consequences of a system where we train for and applaud structured minds, order (e.g., do A, then B, etc.), and certainty. In particular, the book “The Trophy Kids Grow Up” gives a bit of a wake up call when it looks at a large and influential generational cohort – the Millennials. It discusses how the millennial generation thrives on structure and explicit instructions. When you give them a checklist, they’re sure to get the job done. But, as a result they can be risk averse and fearful of making mistakes.

Although I hate to use a broad brush with a generalization like this, or continue the judgement of this generation, while teaching undergraduates during grad school, I saw this more often than not. I saw students that not only struggled with loosely defined problems or real-world (ambiguous) simulations, but also with ones that broke down when they experienced any form of failure. Whether it be the pressure of the program, or ambiguity, it made me work harder to try to get these students to understand the value of this learning, how it would help them grow, and how making mistakes is often what makes us who we are.

So, where do we go from here? How do we give people an edge in times of uncertainty? How do we stay resilient and agile amidst flux?

For starters, I think we work in our public school systems. We need more science fairs or practical projects that expose students to ambiguity. We need ways to work on how to ask good questions and how to operate in situations without clear constraints. We need to build empathy. And, in particular, we need to figure out how to combat the constant need for the “right answer” and perfection, before it's too late. I was always told as a kid you learn the most from making a mistake (and often rolled my eyes), but this adage has rung true.

Today, universities and companies hiring new graduates are working towards teaching and training individuals on how to deal with ambiguity, often unravelling their propensity towards certainty they were taught in school. But, think about the possibilities for academia and business if the next crop of leaders was already equipped to think analytically and creatively in situations where you might have less information than you’d like and where variables might change? These adaptable leaders would be capable of looking at new realities through fresh eyes. to spot and seize valuable opportunities, and steer clear of the “how we’ve always done it” mentality. Risk taking, creativity, flexibility and independent thinking are critical attributes for leaders in the future. The likes of Harvard or Korn-Ferry point to these as critical capabilities of leaders in the current and future complex world.

So now, picture this….A wide eyed young woman went to college to become a business leader. Things were going well, but she had to take things a little slower as she got really sick part way through and was diagnosed with Type 1 Diabetes. She became a consultant at a great firm, thinking that this was how she might scale the corporate ladder, but then decided to support her partner and cross the border where they both pursued a work stint in the United States in one of the worst economies it had seen.

She had to keep her head down to keep a job. Progression wasn’t necessarily possible nor the focus. But, she fell in love with a city (Chicago), people, and new options. However, her husband then got asked to return to Canada to a city that Sabrina never imagined (nor had any desire) to live in. She also had lost a bit of her love affair with consulting. She moved up to one of the coldest cities in Canada. She became a publicist for a friend’s new book. She got involved with TED and the TEDx community. She took online courses.

She returned to consulting as a favour to a partner and applied to graduate school. Fast forward to graduate school where she got her stride. She thrived in the uncharted world of graduate school and pursued a dual degree. She invested time in projects with real companies, dreamed up entrepreneurial ventures, helped other students build their acumen in creativity and innovation, embracing ambiguity, and loving the unknown.

She graduated and after two years, is 31 years old, married to an incredibly supportive husband, and has a beautiful 10.5 month old little girl. She has seen success, but at very different measure and through a very different path than originally conceived. She isn’t living in a penthouse. She has been recognized for achievements, but her greatest achievements are those that don’t come with a plaque.

She has a great network of people, not because of attending the right events or because of her influence, but because of the multi-dimensional interests she has developed and the diverse experiences she has taken on. She is working for herself with great people, trying to make a life and a business that makes a difference in this world.

This is me. And, apologies if you felt like you got whiplash. That picture does not even begin to capture every dimension of me or what I’ve gone through, but it gives you an idea. I do not regret a single experience or the path I have taken to get where I am today. However, it is not the life I ever imagined.

It has been a winding road and continues to be exactly that. So, I choose to embrace the ambiguity, complexity, chaos, constant change, fuzzy boundaries, and risk taking of the emerging world. Will you join me?

Sabrina Sullivan

About Sabrina Sullivan

Strategist, Futurist, Recovering Consultant and Mom. Sabrina has made it her life’s work to help organizations integrate environmental and social sensibilities with complex business realities.

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