The Three Questions for Dream Discovery
Find your dream by looking back before you look forward
The Three Questions framework is a structured introspection process that guides you from self-knowledge to purpose to impact. Rather than starting with a blank page, Squibb argues that your dream is already encoded in your life experience. You just need the right questions to decode it.
The three questions are asked in a deliberate sequence: first you identify what you genuinely like and dislike (your compass), then you identify your deepest pain (your fuel), and finally you determine how you can help others (your connection to the world). Together, these three answers form the raw material of a durable dream.
Squibb adds a bonus validation step: sit with your answers for days or weeks and observe whether the idea takes hold of your subconscious. If you cannot stop thinking about it, if you wake up with it on your mind and find yourself making notes late at night, then you have found your dream. If it slips away, the idea was only good on paper.
- The path to the future begins by looking back at your life experience
- It is never the idea that makes a business succeed but the people and motivation behind it
- Pain is what gives purpose real traction, turning wants into needs
- There is no such thing as a special idea in business, only a special ability to execute on it
- A dream must be rooted in something you genuinely care about or it will fail
- What Are My Likes and Dislikes?Make an honest inventory of what you genuinely enjoy doing, what gives you energy versus what drains it, and what you are actually good at versus what you have merely been trained to do. Be completely honest: write down the real answers, not the ones you wish were true. This is your compass for finding your dream.Pro tipAsk yourself: what would I do today if I had no job and no financial worries? If you had five million dollars in the bank, what would you still want to spend your time doing? That answer is your starting point.WarningDo not confuse what you are experienced in with what you actually like doing. A chef who is tired of cooking but loves photography will fail if he opens a restaurant when his heart wants a studio.
- What Is My Pain?Identify the formative pain in your life, whether from childhood, career setbacks, personal loss, or injustice you have witnessed. Pain is the fuel that gives a purpose real traction. Squibb calls it a 'pain anchor' that reminds you why you are doing what you are doing, the thing you are running away from as well as the destination you are running toward.Pro tipYou would never appreciate summer as much without first enduring winter. Do not run from your pain; harness it, understand it, and channel it into purpose.WarningPain must be processed, not suppressed. If you deny bad things happened or refuse to examine them, you lose one of the most powerful forces available to drive your dream.
- How Can I Help Others?Determine how your likes and your pain connect to the needs of other people. This is not just altruistic but practical: your dream will require customers, supporters, employees, and investors, all of whom need to relate to what you are doing. Working out how you can serve others ties the knot between your internal compass and the external world.Pro tipThis question is also a cheat code for stepping into the shoes of your future customer. It helps you sense-check whether your dream has meaning beyond your own satisfaction.WarningBusinesses without a mission to help others are on borrowed time in a transparent, connected world. Greed-based models will struggle to attract employees and customers going forward.
- Bonus: The Subconscious Validation TestAfter answering the three questions, sit with your dream idea for days or weeks without forcing anything. If the idea lodges in your mind and you cannot stop thinking about it, you have found your dream. If it fades unless you make an effort to think about it, it was only good on paper. To make this test work, suspend your financial worries by imagining you have five million in the bank.Pro tipWhen you have truly found your dream, it will be harder to stop yourself from pursuing it than to actually do it. That feeling of inevitability is the acid test.WarningThis test requires you to be out of fight-or-flight mode. If you are overwhelmed by bills and survival concerns, the test will not work because fear drowns the signal.
After selling Fluid at forty-two, Squibb wrote a list of likes (talking to people, helping entrepreneurs, selling, sharing knowledge) and dislikes (meetings, difficult people, reading long documents, having nothing to do). His pain was being alone and helpless at fifteen. His help mission was ensuring no one else would face that isolation. This led him through a podcast, then TikTok videos, and finally to building HelpBnk.
Chris worked at a bank and suffered severe mental health issues including suicidal thoughts. He recovered by walking in the South Downs. His likes were walks and nature. His pain was mental health suffering. His help mission was preventing others from experiencing the same crisis. He pitched a walking-and-tea business called We Power On.
Squibb invested in a company positioning itself as the Asian equivalent of Red Letter Days. The founder's pitch was purely market-gap based: it works in Europe but nobody has done it in Asia. The numbers looked great but the founder had no personal connection to the mission.
At forty-two, after selling his agency Fluid, Squibb found himself in a listless phase. He had never looked back on his life and reflected because he had been too busy building businesses. When he finally did, he stumbled on the first question (what do I like doing?) and it led him to start a podcast interviewing entrepreneurs. That podcast led him to video content on TikTok, which led to HelpBnk. Each discovery emerged from following his likes, understanding his pain of being alone at fifteen, and recognizing that he wanted to help others avoid that same isolation.