‘You are comfortable with ambiguity’
I am ‘in the market’ for a new role right now, as they say, and one phrase/cliché recurs frequently in job descriptions: ‘You are comfortable with ambiguity’ - i.e. it’ll be chaotic and you’ll need to be okay with that - there is no road map for you, in fact, you will be the cartographer. It’s often paired with ‘You have a bias for action’ and ‘you are excited by change’. (I have, and I am, so that’s fine.)
Being able to run while the ground shifts beneath you takes practice. As a leader in these situations, you’ll spend a lot of time contextualizing chaos for your teams, helping them focus on what matters and dial down the noise that would otherwise make it harder for them to be successful in their roles. Essentially, you have to be comfortable enough with ambiguity and constant flux to find and provide workable clarity for your team, not all of whom may be equipped to duck and weave to the same degree as you. For your team, you and the agenda you present become points of solidity.
Even in a startup, where uncertainty is often the default state, it’s not uncommon to find people who cannot deal with ambiguity and for whom you have to compartmentalize where they focus, insulating them and their priorities from the ever-present chaos - which of course stretches you further.
It’s a challenge, and it’s why stoicism has been embraced by folks in the startup world - it’s a philosophy that, in part, emphasizes how to maintain clarity and control what you can, and detach yourself emotionally from what you cannot.
I have a history of jumping into uncertain situations. I took on a manufacturing business in Ireland right as the 2008 crash bottomed out – with no business experience. I led teen expeditions in the Caribbean in my early 20s, creating multi-week, multi-island itineraries and adjusting them on the fly as we dodged tropical storms and dealt with boat breakdowns and medical emergencies. I’ve survived and thrived at two media startups, with half a dozen ‘pivots’ between them, and none of my other roles have been formulaic or cookie-cutter - and that’s how I like it.
Friend and former colleague-in-chaos Ernie Sander interviewed me for the ‘You Said What?’ podcast about a big dose of uncertainty from 20 years ago which helped set the table for all that, in a way. Here it is - but the synopsis follows below.
The post-9/11 email
Two days after 9/11 I got an alarming email from a stranger. I was 21, had just finished a law degree but had no interest in being a lawyer. I was gearing up for some solo travel – I was Africa-obsessed and had a low-budget volunteering trip to Tanzania planned - flying to Nairobi on 9/25, two weeks after the attack.
The email was a warning flare from an American volunteer with whom I was meant to overlap in Tanzania: she was returning to the U.S. in the aftermath of 9/11, and wanted to alert all subsequent volunteers to what lay in wait. The gist: the so-called volunteer organization was a mess; the program director was disheveled and disorganized, to put it mildly; little to no money was going to the charities listed on the website; there was no structured program in place that could make use of volunteers. It was chaos.
The email continued, urging anyone who still planned to go to focus their energies on one organization called ‘Lohada’. Lohada was essentially an orphanage run by woman called Happiness Wambura, who took in children orphaned by drug addiction, AIDS, or other calamity. It had another facility further west looking after the elderly.
I replied to all on the chain that I was past the point of no return, and that I’d be going to Tanzania regardless and would report back for the group. I had my travelers’ cheques bought, if things fell apart I’d just go walkabout in Tanzania. I decided not to share this new information with anyone who might dissuade me from going –including my parents – and flew to Kenya to catch a bus from Nairobi to Arusha, near the foot of Mt Kilimanjaro, as if nothing had happened.
Nothing, apart from 9/11, obviously. The world at large was in a weird limbo after the Twin Towers attack, as we all waited for George W. Bush to do whatever it was he would do, while trying to figure out what Al-Qaeda was and where they were. I chose to ignore all that. I felt I would be insulated from the macro environment in a small tourist town in Tanzania and could just get on with what I was doing. It dawned on me during the bus ride across the Kenyan/Tanzanian border that I now had no clue what I’d be getting on with. I’d arrive after dark in a strange town in Africa, not sure if anyone would be there to meet me, not sure if I had anywhere to stay that night, not sure if I had a plan for the next two months. I had to be comfortable with that ambiguity.
Most of what the previous volunteer had said was spot on. Everything was chaos, no two days of the two months I spent there followed any pattern. Those of us who landed after the fallout set about trying to wrest Lohada out from under the nose of the aforementioned program director and set it up to stand it on its own two feet. It was a bizarre and often uncomfortable situation.
We emailed and worked with the departed volunteer, who kept things moving from the U.S. to build a fundraising organization and website. On the ground, we were trying to coach Mama Wambura on what this change would mean for her. Previously, the program director had handled the inbound western volunteers, organizing their accommodation and advising them on all logistics. That would now fall on this good-hearted, but unprepared and over-taxed samaritan to figure out, on top of trying to build an orphanage from scratch. She would be independent, but she would also be independent.
A privileged, green 21-year-old from Dublin was of very limited utility to a troubled, nascent charity on the ground in Tanzania in the middle of an existential crisis - I knew that, but I did what I could in the situation, drawing from my limited, sheltered life experience. I helped draft mission statements, helped Mama Wambura write a plan for onboarding and housing volunteers. In the months and years that followed, as the network of former volunteers fanned out around the world to fundraise from overseas and recommend other like-minded people to get involved, Lohada gathered momentum.
I’m under no illusion as to how small my contribution was. Lohada goes from strength to strength because of people like Tina Ashamalla, her brother Mike and others like them who drove it forward from the U.S., and of course because of the indefatigable Mama Wambura, the backbone of the whole operation. It now has a sizable campus on the outskirts of Arusha, a rolling band of volunteers, a child sponsorship program and the support of a healthy 501(c) charity in the US and a board of intelligent people. But whatever little bit I did to help get that momentum started, I’m delighted to have contributed to something positive emerging from destructive chaos. Personally, I came home with a greater understanding of how far outside my comfort zone I’m willing to go, what my tolerance for ambiguity is – and that has only grown in the 20 years since.
I tell a lot of stories in the workplace from my travels, former jobs, and various weird and debatably relevant situations I have found myself in. That bank of stories help me give context to my team-mates when things look grim, and get their heads out of the boat a little. Sharing personal experience also goes a long way to building trust.
Comfort with ambiguity comes from experience. Developing a few callouses on the palms readies one for hard labor. Being directly exposed to a little chaos, similarly, builds character, perspective, resilience. If your team doesn’t have experience with uncertain work environments, you have to lend them yours, and expose they by degree to the full chaos to which they’ll help bring order. You have to coach your people to navigate adversity, and you can’t do that by totally shielding them from it.
Very few situations are so chaotic, in life or at work, as to be bereft of opportunity or hope. There is almost always a path back to order and fulfillment. Being able to stay calm enough to identify that path, no matter what the circumstance, is half the battle.
