Category Archives: Professional Self-Coaching

Brendan was thirty-three, a research scientist, and had just been made responsible for something he’d never done: partnerships, licensing, rooms full of people from the business side. He’d been to three events. At each one he’d explained his work with total accuracy and watched faces politely close. So he found a coach — a good one, expensive, booked solid for three months. She rang him anyway — she had no space for him, and asked what the problem was regardless — and told him what she would actually do in those sessions. He put the phone down and went to find a notebook.

Haruaki knew everyone — twenty-two years in-house, three years advising boards, a contacts list running to more than a thousand names. Then one Sunday he needed a specialist he could trust with something delicate, and scrolled for forty minutes. He knew where they’d all worked. He could not tell you how a single one of them thought. I have spent twenty years meeting people and building nothing. Except one — a woman who had asked him a real question at an emptying seminar three years earlier, and who had rung him four times since. This is the story of what happened in that one hour, and what Haruaki changed afterwards: fifteen relationships out of a thousand names, and the difference between a network and a list.

Fionn had been his own boss for eight years when a long-standing client offered him a substantial six-month project. Good fee. Good client. Familiar work. Saying yes seemed obvious. But for almost two years, Fionn had been saying he wanted to take his business in a different direction — and every sensible decision he made seemed to keep him exactly where he was. Then he changed the question. What followed is a story about self-coaching when you’re your own boss — and why sometimes the thinking that most needs challenging is the thinking that seems completely reasonable.

Farida was good in the room. She was curious, she asked real questions, and she left every event feeling that something had actually happened. Then she got home, and nothing had. Forty cards in a drawer, and a follow-up email she rewrote four times and never sent — polite, true, and completely worthless. Then an email arrived from someone she’d met two days earlier, and it did the one thing hers had never done.

Kofi’s work was excellent. His pipeline was emptying. So he did everything you’re supposed to do — updated the profile, explained the methodology, described the outcomes — and could hear the pitch in his own voice every time. Then a woman he’d met once, eight months earlier, rang out of nowhere: “We’re restructuring. And I remembered what you said — that if you redraw the chart without dealing with the trust, people just go back to working the way they always did. Nobody has ever put it to me like that. Can you come and talk to us? He hadn’t pitched to her. He’d told her about the worst thing he’d ever got wrong — and eight months later, she could still repeat it. This is the story of what he stopped doing, what he started doing instead, and why the diary filled up again.

Ingrid was fifty-two, a structural engineer, and a partner in a practice that had put its name on buildings people trusted their lives to. And she was sitting in a car park, in the dark, not getting out of the car to go into the networking event. What she hated was never the people — it was what the room seemed to require: brightness, availability, an eagerness to be liked. She had told herself for thirty years that this was a character flaw. Then after she went its — she always did — she watched a man in the noisiest corner of that room do it entirely differently — and went home to write down what thirty years had actually taught her — and brought it back to the next networking event — to three engaging conversations.

Maddy had been offered voluntary redundancy after twenty-three years with the same organisation. She could stay. Or she could take the package and leave. Everyone had an answer — her husband, her closest colleague, her sister. Maddy didn’t. So she turned to AI — the very technology reshaping her workplace. She gave it everything she thought it needed to help her decide. By eleven o’clock she knew considerably more than she had at seven. She still didn’t know what to do. Then she changed the question. What followed is a story about self-coaching in the age of AI — and the difference between using technology to help us think and asking it to do our thinking for us.

Tade’s answer was perfect. “I’m a product designer. I work on the checkout experience for a fintech platform.” Clear, accurate, exactly the right length — and every time he gave it, the same small nod, the same “cool,” and a silence he never knew how to fill. He’d been to eleven events that year and couldn’t name one relationship that had come from any of them. Then he watched someone else answer the same question, and say one more sentence — and went home to find the three stories that had been sitting in ten years of work, unspoken.