Always look back to see how far you’ve come and stay motivated

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Every January, Edward faces the same anxiety: his savings aren’t where he thinks they should be. Despite a strong income, he can’t shake the feeling he’s falling behind. Then he discovered measuring backward.

He picked the last 12 months, grabbed his notebook, and set a timer. Within minutes he had a list: an emergency fund that doubled, pay-down of $5,000 in credit card debt, and completion of evening programming courses he once thought impossible. As he read each line aloud, his chest relaxed—the past year suddenly looked like a series of wins rather than a blur of bills.

That night, Edward felt proud. He set three wins for tomorrow—finishing a budgeting task, researching a new savings account, and planning a weekend hike to recharge. The next morning, he woke early, determined to tick off those wins. By week’s end, he had built momentum, celebrating daily wins and sharing them with his partner over coffee.

Psychological studies on goal-setting and self-regulation show that tracking progress against your starting point fuels motivation far more than chasing distant ideals. Edward’s habit of measuring backward transformed his stress into energy, proving that self-determined, backward metrics can liberate and empower.

Set aside five focused minutes to review a chosen period—90 days, six months, or a year. Jot down every real achievement, from paid-off debt to skills gained, date it in your journal, then read the list out loud. Share a standout gain with someone you trust and imagine how each win feels. You’ll end the day with renewed confidence and direction. Try it tonight.

What You'll Achieve

Internally you’ll feel a boost of confidence, gratitude, and reduced anxiety. Externally you’ll gain clearer priorities, energized focus, and a proven habit for sustained motivation.

Build a simple backward-tracking habit

1

Choose a time frame

Pick one span—90 days, one year, or ten years—to review. Set a timer for five minutes to keep it focused.

2

List specific GAINS

Bullet every real improvement: skills learned, relationships strengthened, goals met, health advances. Be as concrete as “I increased my savings by $2,000” or “I ran my first 5K.”

3

Record in a journal

Write or type this list into a dedicated section. Date it clearly so you can revisit and compare next time.

4

Celebrate and visualize

Read your list out loud, share a key gain with a friend, or imagine how each point lifts your confidence. Feel the momentum it creates.

Reflection Questions

  • What’s one gain from the past three months you’ve overlooked?
  • How does listing your achievements change your mood or energy?
  • What new goals will you set after seeing your recent progress?
  • When you share a key gain with someone else, how does that deepen the win?

Personalization Tips

  • A high school student reviews grades and extracurricular milestones since freshman year to see academic growth.
  • An amateur chef lists every new recipe mastered over the past six months to fuel kitchen creativity.
  • A software developer logs completed features and languages learned over the past year to guide next learning goals.
The Gap and The Gain: The High Achievers' Guide to Happiness, Confidence, and Success
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The Gap and The Gain: The High Achievers' Guide to Happiness, Confidence, and Success

Dan Sullivan 2021
Insight 3 of 7

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