The Gap and The Gain: The High Achievers' Guide to Happiness, Confidence, and Success

by Dan Sullivan

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

By saying happiness is something we’re pursuing, the direct implication is that we don’t have it now. You don’t pursue something you already have.

When your happiness is tied to something in the future, then your present is diminished. You don’t feel happy, confident, or successful. But maybe in the future you will be, or so the logic goes.

“Your future growth and progress are now based in your understanding about the difference between the two ways in which you can measure yourself: against an ideal, which puts you in what I call ‘the GAP,’ and against your starting point, which puts you in ‘the GAIN,’ appreciating all that you’ve accomplished.” —Dan Sullivan

You’re in the GAP every time you measure yourself or your situation against an ideal.

“The day you stop racing is the day you win the race.” —Bob Marley

“If you focus on what you lack, you lose what you have. If you focus on what you have, you gain what you lack.”

Ideals are like a horizon in the desert. No matter how many steps you take forward, the horizon continues to move out of reach.

Ideals are meant to provide direction, motivation, and meaning to our lives. They are not the measuring stick. Our society has trained us to measure ourselves against our ideals, which by definition are unreachable. Goals, conversely, are reachable.

GOALS EXPAND HAPPINESS “I don’t think we set and achieve goals in an effort to become happy. We do it because we are happy and want to expand our happiness.”

Being in the GAIN means you measure yourself backward, against where you were before. You measure your own progress. You don’t compare yourself to something external. You don’t measure yourself against your ideals.

When you’re in the GAIN, your life is based on your actions and results, not what could have or should have happened. The GAIN is about real “measurables,” not ideals. As performance coach Tim Grover has said, “Winners don’t have a to-do list. They have a ‘done’ list.”

“I’ve discovered that when something very emotional happens to me, it stays with me until I’ve converted it into lessons. Before I knew this was the case, I could become paralyzed by negative experiences for long periods of time.”

An experience only becomes valuable and useful once you’ve transformed it into a GAIN. Many people have lots of experience but very little learning.

Seth Godin said: “The rule is simple: the person who fails the most will win. If I fail more than you do, I will win. Because in order to keep failing, you’ve got to be good enough to keep playing.”

Everything in life happens FOR you, not TO you. Nothing can stop you so long as you transform every experience into a GAIN.

“The meaning of life is whatever you ascribe it to be.” —Joseph Campbell

“You, and you alone, are the person who should take the measure of your own success. I do not try to be better than anyone else. I only try to be better than myself.” —Dan Jansen

happiness is where you start, not where you finish.2

REALITY MEASURED BACKWARD “The future isn’t a reality—it’s a projection. And because it’s not reality, it can’t be part of any real measurement of your progress. The only way to measure goals is backward, against the past. Use the reality of where you currently are and measure backward from there to the reality of where you started.”

Needing anything outside of yourself is a form of being in the GAP.

When you’re in the GAP, you have an unhealthy attachment to something external. You feel you need something outside of yourself in order to be whole and happy.

When you’re driven by need, rather than want, you have an urgency and desperation to fulfill that need. The problem is that “needs” are unresolved internal pain, not something you can solve externally.

As the famed entrepreneur and investor Naval Ravikant said: “Training yourself to be happy is completely internal. There is no external progress, no external validation. You’re competing against yourself—it is a single-player game.”6 Happiness cannot come from something outside of yourself.

NO SCARCITY WITH WANTING “In the world of wanting, there’s no scarcity, because it’s a world of innovation—not of taking. Wanters are creating things that didn’t exist before.”

Your viewpoints and judgments of your own experiences are infinitely more important than anyone else’s judgments of you and of your experiences.

Start by grabbing a piece of paper and answering the following questions: What do you feel you “need” in order to be happy? Who or what do you measure yourself against? When is a time in your life where you made something or someone into a “need,” and thus created an unhealthy GAP in your life?

“The difference between the two words ‘need’ and ‘want’ is gargantuan. When you need someone, you lose your independence and agency as a human being. Wanting, on the other hand, is the first step in learning how to love someone. The difference between need and want is the difference between codependence and love.” —Michaela Rollings, popular blogger

Consider Trevor’s words: “I think you can have both.” What he meant by “both” is: Having an intense commitment to succeed, and Having a healthy detachment from what you’re doing

WANTING IS A CAPABILITY “This transformation, moving from needing to wanting, is a capability. The more you do it, the better you get at it. Yes, it’s a risk at first because your previous tendencies of justification are well developed and habitual.”

As he stated, he loves football. He works hard. He’s committed to winning. But he doesn’t need football. That’s his point—you can have both: you can be 100% committed to something and simultaneously not need it.

When you’re in the GAP, you “need” something outside of yourself. You’re driven externally. You’re reactive to what’s going on outside of you. In the GAIN, you don’t “need” anything outside of yourself. You’re driven internally. You take what happens outside of you to transform and improve yourself.

Being in the GAP is driven by an unhealthy “need.” Being in the GAIN is driven by a h...

Obsessive passion is highly impulsive and fueled by suppressed emotions and unresolved internal conflict. You become obsessed with something to the point of an unhealthy desperation. You believe you need it, and can’t be happy without it.

WANTING EMPOWERS YOU “When you take the wanting approach to your future, it also means that you’re leaving behind the world of needing. It means that no one else is responsible for your future progress and success.”

This brings up a highly nuanced and crucial distinction: you can want something and be 100% committed to that thing without needing it. This is the counterintuitive reality: by no longer needing what you want, you are actually far more enabled to get it. You can freely perform and be in the flow, rather than obsessing over how it will turn out.

Playing a longer game allows you to embrace being “here.” Yes, you have goals and vision, but you’re completely happy where you’re at. You’re here, and you love being here. You love what your life is like. You’re blown away by your GAINS. You appreciate everything and everyone around you. You’re genuinely happy. You also love what you’re working on and building. You’re committed and focused, but you’re not trying to rush to the next place to fill some unresolved need. You’re doing what you love. You’re confident in where your life is going.

By freeing yourself from unnecessary “needs,” you’re finally enabled to create the progress and life you want. You know you’re already whole and complete without those goals. You’re fully free to have whatever you want, and because of that, it’s actually much easier to get what you want.

WANTING CREATES ABUNDANCE “In the wanting world, there is an abundance of resources as a result of the creativity and innovation that comes from wanting.”

The GAIN creates freedom. The GAP makes you a slave to your unhealthy need. The GAP makes you a slave to “there” and makes “here” a prison you’re trying to escape from.

Pull out your journal and answer the following questions: Are there any areas in your life where you have obsessive passion? If so, what unresolved internal need are you trying to fill? What about your life and work do you love? What is your long game? When you’re playing the long game, you’re doing what you love. You’re not doing something just to get somewhere else. Do you have a long enough time table to truly slow down and enjoy being here, or are you trying to quickly get “there”? Look at your life right now—what are all the GAINS you can think of? How would your priorities change if you were playing the long game?

In the classic book Escape from Freedom,26 Erich Fromm defines two types of freedom: Freedom from (which is external) Freedom to (which is internal)

Freedom from is lack of obstacles—you’re not a slave to someone or something. Freedom to is the presence of control—you’re your own master.

These build on top of each other. Freedom from means you’ve removed the external obstacles. Freedom to asks, “Okay, what will you do now?”

IDEALS AREN’T FOR MEASUREMENT “An ideal can’t be measured. It’s there for emotional, psychological, and intellectual motivation, but it’s not there for measurement.”

“Define success on your own terms, achieve it by your own rules, and build a life you’re proud to live.” –Anne Sweeney, American businesswoman and former co-chair of Disney Media

As Seth Godin explains: “Our current system of teaching kids to sit in straight rows and obey instructions isn’t a coincidence—it was an investment in our economic future. The plan: trade short-term child labor wages for longer-term productivity by giving kids a head start in doing what they’re told.”

PROGRESS MUST BE CONCRETE “A sense that we’re making progress toward our goals makes us happy. But to truly get the feeling of progress, we need to base it on concrete facts. When we set goals, we must be specific so we know when they’re accomplished—usually, a number was reached or an event took place.”

Children are trained to measure themselves against external reference points. These reference points are not generally chosen by the child themselves, but by society and the education system. As these children grow up, they’re not taught how to determine their own reference point or “measure of success.” Instead, they adopt the reference points that society deems as “success”—money, fame, social media likes, etc.

Every one of us has reference points we use to measure ourselves. Pull out your journal and answer these questions: What are the reference points you measure yourself against? Why did you choose those particular reference points? How do you define and measure success for yourself?