What's Your Dream?

“ The paradox of our dreams is that the thing we most want in life is often the thing we are most afraid of doing.

“ The paradox of our dreams is that the thing we most want in life is often the thing we are most afraid of doing. ” e.style.display='none');if(typeof getContentsSections==='function')setTimeout(getContentsSections,50)" /> Simon Squibb asks thousands of strangers one question: "What's your dream?" The word matters. Goals are binary — pass or fail — and expire at year's end. Resolutions dissolve when willpower fades. But a dream is engineered for survival: big enough to contain failure, outlast bad years, and accommodate career pivots. No annual review will tell you your dream performance was subpar. Squibb discovered this question by accident. After selling his agency for millions and retiring at forty, he posted a video about fatherhood that went viral. A commenter snapped: "Not everyone gets to have a dream." That troll unknowingly launched Squibb's mission. When he asks the question on the street, people physically transform — standing taller, eyes alive, describing futures they've never shared aloud. Dreams, unlike goals, don't punish you for falling short. They persist. TAKEAWAY 2

“ The real choice isn't mortgage vs rent, but mortgage vs freedom. ” e.style.display='none');if(typeof getContentsSections==='function')setTimeout(getContentsSections,50)" /> Squibb bought his dream Porsche after selling his company. Euphoria lasted one week. By week two, someone scratched it and he spent three days at the garage. By week three, anxiety had replaced joy. When he sold it, the relief felt almost as good as buying it. Every possession he's shed since has made him feel freer. The housing trap works identically. A mortgage locks you into a job to service debt, devours savings that could fund a business, and consumes mental bandwidth. Squibb slept on a friend's sofa for months in Hong Kong, which freed him to launch the agency that changed his life. He argues most "dream" purchases — homes, cars, watches — end up owning you through maintenance, worry, and replacement cycles. The possession becomes the boss. TAKEAWAY 3

“ We would never appreciate the summer as much without first enduring winter. ” e.style.display='none');if(typeof getContentsSections==='function')setTimeout(getContentsSections,50)" /> Pain gives purpose its traction. Squibb calls it a " pain anchor " — the deeply personal wound that turns a vague want into a compulsive need. Kellie, a dog groomer abandoned by her mother as a teenager, channelled that trauma into a mobile pet salon caring for animals "that can't speak up when they need help." Sophie nearly died after childbirth, couldn't find comfortable jeans during recovery, and created I Am Denim — now stocked by Debenhams and featured in Vogue. Squibb's Three Questions framework maps this journey from inside out: 1.…