Introduction
Michelle Ottey calls herself, without irony, "an infrastructure nerd." Her career spans corporate and investment banking at Citibank, then more than a decade at the World Bank Group's private-sector arm, IFC, structuring public-private infrastructure deals across the Caribbean. She is, by any measure, someone whose value has come from control: modelling deals precisely, managing outcomes, delivering results.
Then she was diagnosed with an aggressive form of cancer, and had to build a version of leadership that didn't depend on control at all.
Speaking to Sope Agbelusi on Everyday Leadership, Michelle traces a career built on ambition and self-proof through to a very different definition of leadership, one built on listening, surrender and what she calls self-mastery.
Building planes on bunk beds
Michelle's fascination with infrastructure predates her career by decades. As a child in Jamaica, she and her siblings built makeshift planes out of plyboard and patio furniture on bunk beds because they wanted to travel and decided, in her words, to "figure it out" and build it themselves. That instinct, find the problem, build the solution, has stayed constant through a career move from a small Jamaican merchant bank to Citibank (where she spent eight years moving from corporate relationship manager to vice president), and then to the World Bank's IFC, where she now leads infrastructure advisory work across small Caribbean islands with "big infrastructure gaps but massive potential for transformation."
Reading the boredom signal before it becomes a crisis
Asked how she knew it was time to leave Citibank after eight successful years, Michelle didn't point to a single dramatic event. She pointed to boredom. "The biggest sign for me is when contentment starts to bore. It goes from slightly a bit too content to actually a little bit bored," she said, describing the point where she could do deals "eyes closed" without being challenged. Her framework is that the most valuable professional relationships are two-way: you contribute strongly to an organisation, but the organisation should also be contributing to your growth. When that balance tips and growth stalls, she treats it as a signal worth sitting with, not ignoring in favour of a good bonus or a recent promotion.
She told her boss a full year before she left that change was coming, not because she had another job lined up, but out of respect for a mature working relationship. Her boss's response has stayed with her: rather than trying to hold on, her manager acknowledged that her role was to help high performers transition well, because the relationship would outlast the job.
Asking to be mentored, and having the guts to say why
Michelle is direct about how she built access to senior people throughout her career: she asked. Not vaguely, but specifically, telling people she admired how they'd managed their careers and asking if they'd be willing to mentor her. Her reasoning is blunt: "All they can say is no. I'm no worse off than if I didn't ask." Several of her former mentors are now colleagues in her own leadership chain, a relationship built years before either side had anything obvious to gain from it. She applies the same approach in reverse now, mentoring people who remind her of her earlier self, often people who, like her, are more introverted and have had to learn to put themselves forward.
Learning to listen instead of chase deals
A pivotal mindset shift in Michelle's career at IFC was realising that being a strong dealmaker wasn't the same as making an impact. "You cannot be chasing deals if you're trying to make a difference," she said. That meant deliberately building her capacity to listen, both to governments describing the problems behind their infrastructure requests, and to private-sector partners' own constraints, rather than jumping straight to solutions. Her role, as she describes it, sits in the middle of both, understanding what a government needs and what will actually work for private capital, because a partnership, by definition, has to work for both sides.
The diagnosis, and the illusion of control
When Michelle was diagnosed, she describes the disorientation plainly: doctors "started to use big words like you're going to have to have chemotherapy" and her life, for a while, "did not make sense." The moment brought her, in her words, to her knees, with a realisation that stuck: "while we have this illusion of control in our lives, there is not actually full control. There is power, however, in accepting that and learning to surrender."
As a self-described "recovering control freak," this was not a comfortable lesson. She continued working through treatment, largely without disclosing the diagnosis to clients, structuring her schedule around chemotherapy every other Tuesday for four months and taking the two most difficult days afterward to rest. She credits the routine and purpose of ongoing work with helping her keep going, rather than treating illness as a reason to fully withdraw.
Writing through grief, and the book that grew out of it
During the isolation of the pandemic, alongside her treatment, Michelle began writing, partly to process grief resurfacing from her father's death three years earlier, and partly because the usual noise of the world had stopped. What started as journalling became a manuscript, now around ten chapters and 5,000 words in progress. A friend, author Jessica (whose surname is unclear in the recording), read an early transcript and told her plainly to stop putting herself in a box: she was a writer, whether or not she'd called herself one before.
Coming home, and letting go of the how
Michelle spent almost 13 years living outside Jamaica, in Washington DC, while working at IFC. After her mother's extended stay supporting her through treatment ended, and her mother returned home, Michelle describes a wave of fear and overthinking about how she could possibly relocate back to Jamaica while keeping her job. With the support of a life coach, she learned to separate the intention (wanting to move home) from the mechanics of how it would happen, and to let the "how" go rather than trying to engineer every step herself.
Months later, in a meeting with Jamaica's Minister of Finance about a new infrastructure programme, she was asked, almost in passing, whether IFC could place someone senior in Jamaica. She said yes on the spot. The timing, combined with a property address that had come to her unprompted weeks earlier, felt to her like confirmation that setting a clear intention and stepping back from controlling the exact mechanism had worked.
Redefining leadership as self-mastery
By the end of the conversation, Michelle draws a clear line between management and leadership. Management, to her, is telling people what to do. Leadership is "the way I live my life, by the actions that I take, by the way that I carry myself," in a way that earns trust rather than demanding it. She's explicit that people trust a leader before they trust a vision, which means the leader has to build that trust through consistent behaviour and genuine listening, not authority alone. Her core belief, repeated throughout the conversation, is that leadership starts with mastering yourself, your reactions, your stress, your need for control, before you can credibly help anyone else move forward.
