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Why Smart People Keep Repeating the Same Mistakes

Last Tuesday evening, 46 people attended The Clarity Room for a free coaching session on Zoom, which I host every Tuesday from 7 pm to 8 pm. Some guests arrived early, while others showed up exactly on time. A few arrived fashionably late, which is a polite way of saying they intended to come at seven but were distracted by life, work, children, traffic, dinner, WhatsApp, existential dread, or a mix of these factors. It happened to be my 43rd birthday. Now, birthdays have a funny way of making a man reflective. You start to realize that recovery takes longer than it used to. Your knees occasionally send formal complaints after a run. And you begin to notice that wisdom often arrives disguised as mistakes you swore you would never make again. Perhaps that is why the evening's topic felt particularly fitting. The Hidden Scripts Running Your Life. As people settled into the Zoom room, I asked a simple question. “Where do you feel stuck?” The responses started appea...
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The Man Who Thought He Had Failed, But Was Actually Regenerating

  This is a story inspired by Episode 2 of The Men's Group Debate Series, held on June 6, 2026, at Savelberg Retreat Center in Nairobi , under the theme "The Men Nairobi Raised Are Not the Men Nairobi Needs." --- There is a particular look some men develop after life has taken a sledgehammer to their plans. Not immediately afterward — immediately afterward, everybody becomes dramatic. There are emergency meetings, prayer requests, lawyers, concerned relatives, and WhatsApp groups that suddenly become more active than Parliament during a scandal. Advice arrives from every direction. Some of it is useful. Some of it is generated by people whose own lives resemble a building under demolition. No. The look arrives later. Months later. Sometimes years later. It is the look of a man who is functioning yet uncertain. The look of a man who pays his bills, attends meetings, answers emails, services the car, renews his insurance, and remembers birthdays — yet quietly wonder...

The Man Who Won Outside and Lost at Home

  This is a story inspired by Episode 2 of The Men's Group Debate Series, held on June 6, 2026, at Savelberg Retreat Center in Nairobi , under the theme "The Men Nairobi Raised Are Not the Men Nairobi Needs." --- There are certain men Kenyan parents absolutely adore. You know the type. The ones whose names appear in church fundraisers. The ones introduced at weddings with lines like: " Meet Benard. He has done very well for himself." Nobody ever explains what it means. "Very well" is one of those uniquely Kenyan expressions. Like "We need to talk." Or "I'm almost there." Or "Let's meet and catch up." Everybody understands the danger, but nobody can define it. Whatever it meant, Benard had achieved it. By forty-three, he owned a house in Syokimau, a second piece of land never called land but always "the investment," a respectable SUV, a consulting business that could occasionally be described a...