Learning to embrace ambiguity

For the first three decades of my life, I lived in environments with clear paths to success.

I was always good at and loved school. The logic was simple: if I paid attention in class, studied, and did well on tests, I would succeed. When I scored poorly on a test or a paper, there was immediate feedback, and the path to improvement was obvious. I had a choice as to whether I would act on the feedback, but the outcomes in either instance was clear. Act and improve. Don’t act and don’t improve.

I chose to act nearly every time. I got superb grades. I scored well on standardized tests of all types. For high school (and even college) level problems, there were knowable and defined solutions if you only put in the work. And then you would get that nice shiny A. 

Early on in my high school career, I decided I wanted to be a Navy fighter pilot. Again, the path was clear: get good grades in high school. Get in shape. Get accepted to either the Naval Academy or get a NROTC scholarship. Do well in math and physics in college. Apply for a pilot slot. 

There were challenges to be sure, but each step could be broken into discrete, knowable actions that if completed, would keep the train chugging. Failure was possible - even probable! - but each step had a defined outcome one way or the other.

When I made it to flight school and got my wings, the path to success as a Naval Aviator was also clear. To be an Admiral required following the Golden Path: Fly in combat and be a good leader in your first fleet tour. Go to TOPGUN. Train the next generation of pilots. Do a Department Head tour. Do a Joint Tour with another service. Get a Navy-funded graduate degree. Become a Commanding Officer. Become a Carrier commander or Air Wing commander. Boom. Stars on your shoulder.

At each stage the funnel narrows and you have to put in real work, but the path is knowable. If you choose to deviate (and I did!) there were clear career consequences. But at least you KNEW.

When I made the final deviation at 32 years old following 11 years of active service, I knew it was the right move for me. But for the first time in my life I was faced with a giant fog bank. I knew I wanted to go to business school so did the things that were definable and knowable: cracked the GMAT, got the right recommendations, applied to all the right places. I thought that something would emerge from the mist. It didn’t. And hasn’t.

Arriving on campus in Palo Alto for the first day of class was bewildering. A world of opportunity was spread before me and I was paralyzed. I thought I was prepared to transition – I had built innovation organizations, built networks with non-military business leaders, read voraciously on risk, history, economics, and psychology. 

But I felt confused and directionless. There was no clear path with definable actions that I could simply follow and be successful. I made the classic bookworm-oriented, business school mistake: I threw my efforts into my studies. Sure, I carved out some time to meet my classmates, but as classroom work was definable, and I knew what was required, I could “succeed.” So I got really good business school grades. 

I soon realized that they were meaningless in and of themselves. No one cared anymore. Prospective employers didn’t look at them. And there were no other applications for other credentials where good grades would move the needle.

The relationships were what mattered – relationships that couldn’t be predicted or defined. Beautiful serendipity at work where formal outcomes not only didn't matter, but were utterly beside the point.

Professionally, I was all over the place. I did five internships in 2 years: Operations with a startup airline, Marketing and strategy with a startup software company, Human Resources with a school in Africa, Railroad work with McKinsey, search fund private equity. I partnered with a friend on a venture. I quickly left. The fog remained.

As I graduated business school at 34, it dawned on me that there were no clear answers and maybe there never would be. I had been unknowingly institutionalized in a mindset that believed a clear path was always definable and desirable. I had a scarcity mindset where dragons existed outside a defined path. My two years on the Farm was an unintended and unwitting detox. I was getting closer to discovering something about Reality.

What I realized is that the most interesting problems in the world don’t have pre-defined solutions.  If they did they would have already been solved. Human flourishing advances not from logical steps, but due to serendipitous intersections of unanticipated outcomes. And the path to progress is littered with innumerable, unmentioned detours leading to dead ends.

Terrifying.

So I went into consulting. A chance to explore a number of industries, get some real world business experience under my belt, and travel. But even the safe path of consulting was rife with ambiguity.

When I first started, my professional development manager, the McKinsey resource who helps guides our path, asked me what I wanted to pursue. I had no idea. So I bounced around, exploring transportation, alcohol distribution, military contracting, energy operations. Slowly, ever so slowly, opportunities emerged as I actually developed some expertise. A path began to emerge.

And now I’m at another transition point – the next step is available if I make the “right” moves. But those moves sit at the intersection of what I’m passionate about and what is important to the overall mission of the organization. Most I’ve talked to have said their path was unique and that while it worked for them, it may not work for everybody.

Which in a way makes sense – the ability to deal with ambiguity, uncertainty, and starting from scratch defines a successful professional in nearly any career. Creating the opportunity to provide value to clients can take a month…or ten years. There are guidelines, but no defined playbook. You need to have an abundance mindset in the midst of uncertainty. Some succeed. Some fail. And often, differentiation between success and failure can’t be assessed before hand. 

But when opportunities do hit, and the prepared team is ready to execute, really incredible things can happen. Companies and governments can be transformed. Decades-old mindsets can melt after six months of deep work, leading to new frontiers. And while projects have clearly defined outcomes defined upfront, its often the unquantifiable discoveries that leave a lasting impact.

The most pressing challenges facing our society don’t have defined answers. Hypotheses abound for how to address climate change – but we need to test them and will invariably face failure until success emerges from an unexpected place. Coronavirus could be with us for months, or decades. The vaccine (developed within a year!) may be good forever or need to be retooled annually. The colonization of space may occur in line with the views of Musk and Bezos, or we may bang our head against the difficulties of travel through radiation-filled vacuum for centuries to come.

There is comfort in certainty, peace in knowing what’s next. But new frontiers are exciting because there is limitless potential amidst uncertainty. As we emerge from an industrial age that attempted to quantify, predict, and optimize everything, an information age mindset focused on discarding assumed projections will need to be adopted. All the low hanging fruit is already picked – but the hard stuff promises to be societally and personal rewarding. 

Our ambiguous world can be scary to those of us who once believed plans could be neatly made and carried out. But the future belongs those who can live with ambiguity, trust that abundance exists, and move forward even when the path ahead is shrouded in mystery.

I’m still learning to love ambiguity. The compounding effect of this mindset started only four years ago, and will likely take many more years to fully blossom.

We all have to take the first step and be willing to change our minds when we discover something new about the world.