Dan Sullivan and Benjamin Hardy

The Gap and the Gain is a collaboration between two authors with complementary expertise: Dan Sullivan, a veteran entrepreneurship coach and founder of Strategic Coach, and Benjamin Hardy, an organizational psychologist and author known for his work on personality transformation, identity, and future-self psychology.

Dan Sullivan

Dan Sullivan (born 1944, in Ohio) is the founder and CEO of Strategic Coach, a coaching organization for high-achieving entrepreneurs that he has run for over four decades. Sullivan is known as one of the world’s foremost coaches for successful entrepreneurs, and his frameworks — including the Unique Ability, the Self-Managing Company, and the Positive Focus — have influenced thousands of business owners globally. He is also a prolific conceptual thinker and has published dozens of books, many as part of The Strategic Coach Series.

The Gap and Gain concept originated with Sullivan as a coaching framework for helping high-achieving clients stop measuring themselves against ideals and start measuring against their actual progress. He observed that the most successful people he worked with were often the least happy — precisely because their capacity for vision was so strong that the gap between where they were and where they wanted to be always appeared enormous.

Core Sullivanisms relevant to this library:

“The way to measure your progress is backward against where you started, not against your ideal.” — Dan Sullivan

“Our eyes only see and our ears only hear what our brain is looking for.” — Dan Sullivan

“The only way to measure the distance you’ve traveled is by measuring from where you are back to the point where you started.” — Dan Sullivan

Sullivan’s emphasis on specificity — concrete, quantifiable GAINS rather than vague impressions of progress — reflects decades of coaching experience: people who speak in specifics about their achievements are consistently happier and more motivated than those who speak in generalities.

Benjamin Hardy

Benjamin Hardy (born 1985, in Georgia) is an organizational psychologist and author with a doctorate from Clemson University. He is known for his work on personality psychology, identity change, and the science of future-self thinking. His previous books include Willpower Doesn’t Work (2018), Personality Isn’t Permanent (2020), and Be Your Future Self Now (2022). Hardy brings empirical psychology to Sullivan’s coaching framework, grounding the Gap and Gain concepts in research on happiness, resilience, trauma, memory, and decision-making.

Hardy’s key contribution to the collaboration is the psychological and neuroscientific support for concepts Sullivan had observed empirically. Hardy explains why GAP thinking is so persistent (it is the default mode of brains trained by comparison-based educational systems), why GAIN thinking produces better outcomes (it creates positive affect, confidence, and resilience), and how memory works in ways that make measuring backward an active, creative act rather than passive retrospection.

The Collaboration’s Core Framework

The Gap and Gain framework (see gap-and-gain-framework):

• GAP: Measuring yourself against an ideal — by definition unreachable, by design producing perpetual dissatisfaction
• GAIN: Measuring yourself backward against your starting point — real, concrete, always growing

The framework addresses the paradox of high achievement: the greater your capacity for vision, the larger the structural gap between current reality and ideal, and therefore the more success you can achieve while still feeling permanently behind.

Key sub-concepts: the need/want distinction, the Experience Transformer, the Three Wins daily practice, and the principle of proactive gratitude (appreciating what you have before pursuing more).

Who Not How: The Companion Framework

Who Not How (2020), also a Sullivan-Hardy collaboration, addresses the execution counterpart to the Gap and Gain mindset work. While the Gap and Gain deals with how you measure your progress (backward against starting point, not forward against ideal), Who Not How deals with how you achieve the goals you set.

The core question shift: from “How will I do this?” (which locks you into current capabilities) to “Who can help me with this?” (which unlocks access to any capabilities that already exist).

Sullivan’s decades of coaching high-achieving entrepreneurs revealed a consistent pattern: the most successful clients had learned to concentrate their attention on their Unique Ability — the activities where their passion and impact are greatest — while delegating everything else to Whos who have their own Unique Ability in those domains.

Key Concepts from Who Not How

The investment mindset: “Rather than viewing people or services as a ‘cost,’ as in the transactional mind-set, everything is viewed as an investment, with the possibility of 10X, 100X, or even bigger returns and change.” This reframes delegation not as expense reduction but as leverage creation.

The vision-leader relationship: “That’s what real leadership is: Creating and clarifying the vision (the ‘what’), and giving that vision greater context and importance (the ‘why’) for all Whos involved. Once the ‘what’ and ‘why’ have clearly been established, the specified ‘Who’ or ‘Whos’ have all they need to go about executing the ‘How.‘”

Procrastination as signal: “What procrastination means is that your goal or ambition is great. It’s something you’d like for yourself, but you’re not the right person to execute the plan to achieve it, at least not right now. You need a Who to get you through whatever stage you’re in.”

The 90-day rhythm: Sullivan recommends breaking large goals into 90-day increments with specific “jumps” (progress milestones) defined at the start of each quarter. This connects to OKR quarterly cadence and the 90-day planning horizons used by 4DX practitioners.

For the full treatment, see who-not-how-principle.

Key Works in This Library

The Gap and the Gain: The High Achievers’ Guide to Happiness, Confidence, and Success (2021): Combines Sullivan’s decades of coaching entrepreneurs with Hardy’s psychological research to produce a practical framework for measuring progress in ways that create rather than destroy happiness. Includes exercises, journaling prompts, and practical implementation strategies.

Who Not How: The Formula to Achieve Bigger Goals Through Accelerating Teamwork (2020): Reframes the fundamental question from “how do I do this?” to “who can help me achieve this?” — a shift that unlocks exponential leverage through collaboration and delegation.

Simplifier-Multiplier Collaboration (2020)

Simplifier-Multiplier Collaboration is a Sullivan solo work (without Hardy) that introduces a binary framework for understanding how value is created and how to maximize it through collaboration. It extends the Unique Ability concept from Who Not How into a theory of collaborative specialization.

The Core Framework

Sullivan argues that all value creation involves two fundamentally different activities: Simplification (going inward, toward clarity and elegant solutions) and Multiplication (going outward, toward scale and expanded reach). These require opposing orientations and generate energy for people with different natural instincts.

“You have to be 100 percent committed to either simplifying or multiplying. If you’re only 95 percent committed, you’ll be five percent thinking about the part of the collaboration you’re not responsible for.”

The Complicator Trap

The key warning: a Simplifier who tries to multiply (or vice versa) becomes a Complicator — generating friction, frustration, and complexity instead of value.

“if you’re a Simplifier who crosses the line into Multiplier territory or vice versa, you’re a Complicator.”

Complexity as Opportunity

One of Sullivan’s most counterintuitive arguments:

“You can commit yourself to looking at the complexity in your daily life as something endlessly good that you can transform into uniquely useful resources and capabilities for yourself and others.”

Rather than resisting or managing complexity, the Simplifier’s orientation is to treat it as raw material — each new wave of complexity creates demand for the next round of simplification.

See simplifier-multiplier-framework for the complete treatment.

Relationship to Who Not How

The Simplifier-Multiplier framework is a structural extension of Who Not How. Where Who Not How asks “who can help me do this?”, Simplifier-Multiplier asks “who can do the other half of value creation that I’m not suited for?” The two frameworks together describe a complete theory of collaborative leverage: concentrate on your highest-contribution activity, trust the right partners with everything else.

Relationship to Other Authors in This Library

• Eckhart Tolle: The GAP is the ego’s preferred measurement instrument — always comparing against an ideal future self. Tolle’s teaching that “only if you resist what happens are you at the mercy of what happens” is the spiritual version of the GAIN practice
• Sahil Bloom: The five types of wealth provide the multidimensional scope within which GAINS should be measured — financial progress is one GAIN, but so are improvements in relationships, health, purpose, and time freedom
• Simon Sinek: Fulfillment (from WHY) rather than happiness (from WHAT) is naturally a GAIN orientation — it is intrinsic and accumulating rather than dependent on external outcomes
• Michael A. Singer: Singer’s practice of letting go of “like and dislike” as the governing criterion is the inner equivalent of releasing the GAP mentality — stopping the measurement of experience against personal preference and receiving what is
• Nick Sonnenberg (Come Up for Air): Sonnenberg explicitly recommends Who Not How for leaders thinking through delegation decisions. The two frameworks complement each other: Sullivan/Hardy address who should do what, Sonnenberg addresses how teams should structure their operational environment to enable effective handoffs
• Shane Parrish (Clear Thinking): Parrish’s ego default — the compulsion to prove competence through personal execution — is exactly the mindset that Who Not How is designed to interrupt. Both frameworks identify the same underlying trap; Parrish diagnoses it neurologically, Sullivan/Hardy address it practically