Jonathan Garrity
NYC • CEO @ Tagup Inc.
← Blog

What I've Learned So Far

February 12, 2026
personallifereflection

Key Narrative

At 36, I’m roughly halfway through my working years and likely a third of the way through life. This is a pause to take stock: what have I learned that I didn’t know at 25? What inputs actually drive my output and happiness? And what should I prioritize in the decades ahead?

This isn’t advice—it’s an attempt at honest self-assessment. What works for me may not generalize. But the exercise of articulating it is clarifying.

Outline

I. Introduction

II. Things I’ve Learned

A. On Work

  1. Compounding is everything

    • Skills, relationships, reputation—all compound
    • The implication: patience and consistency beat intensity

  2. The importance of the work matters more than the quality

    • Direction over velocity
    • Choosing problems > solving problems

  3. Management is a distinct skill, not a promotion

    • I had to learn this the hard way
    • The transition from doing to enabling

  4. Speed is underrated

    • Fast iteration beats careful planning
    • But: fast on execution, slow on strategy

  5. Most business problems are people problems

    • Hiring, culture, incentives
    • Technical problems are often easier

B. On Thinking

  1. Writing clarifies thought

    • If you can’t write it clearly, you don’t understand it
    • The discipline of the page

  2. Strong opinions, loosely held—actually practiced

    • Conviction to act + humility to update

  3. Mental models accumulate

    • Reading across disciplines pays off slowly, then suddenly
    • The value of history, physics, biology as lenses

  4. Intuition is compressed experience

    • Trust it more as you get older
    • But keep calibrating it

C. On Relationships

  1. A few deep relationships beat many shallow ones

    • The returns to depth are convex

  2. Marriage is a choice you make repeatedly

    • The decision to marry is just the first one

  3. Proximity drives relationships

    • Invest in being near the people who matter
    • This is underrated in career decisions

  4. Most conflicts are misunderstandings

    • Steel-manning prevents most arguments
    • Assume good faith until proven otherwise

D. On Health and Energy

  1. Sleep is the foundation

    • Everything degrades without it
    • Protecting sleep is a productivity strategy

  2. Exercise is non-negotiable

    • The cognitive benefits rival the physical ones

  3. Energy management > time management

    • Know your peaks and protect them

E. On Happiness

  1. Adaptation is powerful—both directions

    • Hedonic treadmill applies to gains and losses
    • Implication: focus on process, not outcomes

  2. Meaning comes from difficulty

    • Comfortable lives are not necessarily good lives
    • The value of challenges chosen

  3. Gratitude is a practice, not a feeling

    • It can be cultivated deliberately

III. My Personal Production Function

What inputs actually drive my outputs?

A. Energy Sources

B. Work Inputs

C. What Drains Me

D. The Output

IV. Priorities Going Forward

A. Doubling Down

  1. Health: More aggressive about sleep, exercise, diet
  2. Family: Time with children while they’re young
  3. Deep work: Protect mornings more ruthlessly
  4. Writing: Increase output, develop voice

B. Adding

  1. Community: Invest in local relationships
  2. Teaching: Give back accumulated knowledge
  3. Creative pursuits: Music, specifically

C. Reducing

  1. News consumption: Low information, high anxiety
  2. Performative obligations: Say no more often
  3. Optimization: Accept good enough

D. The Big Questions

V. Conclusion

Notes / Sources

Inspiration

Frameworks Referenced

To Research / Verify

Comments