If work feels like fun – then it is not work. 

Work that you are highly skilled at feels like fun. 

Skills are acquired via effort (hard work) + cycles of feedback. 

Acquiring skills, therefore, is the only hard work. 

Applying skills is how you make money. 

If you feel like working hard when making money, you probably do not have the skills to make it fun. 

To acquire skills, you need to learn and go through the four steps 

1. Unconscious incompetence

2. Conscious incompetence

3. Effortful competence

4. Effortless competence – Mastery.

Stages 1, 2, and 3 are hard and look like work. Stage 4 is where you have fun and make money while having fun.

So why do people not go through 1, 2, and 3 to get to 4? 

Because all it takes is two steps

a) Find what to do ( read books / have a coach, etc)

b) Do it 

But we procrastinate – 

There is this vast discussion and literature about habit formation

What is missing and the critical step is removing procrastination

Even that starts and goes via these steps:

1. you are unconscious that you are procrastinating  

2. You become aware of the four types of procrastinating and identify which case(s) are relevant to you, and what skills are missing

3. acquire all those skills again via the four steps of competence. 

4. Practice every day till it becomes 2nd nature ( habit)

I made this Mindmap for the entire UPilot team to use and move the hand breaks on whatever skills they are trying to achieve. (Here is a screenshot.) I also included a list of 29 books to master every skill required, which will lead you to the first step. Yes, skill acquisition is hard work, but you must go through that to create joy in work. 


Work will always look like work if you have mediocre skills in areas where you want to progress.

Procrastination delays getting to your goals and the life you desire. 

PS: Here is a list of books for skills missing in each type.


  1. Self-Discipline and Time Management (Overdoer) – “Deep Work” by Cal Newport
  2. Accountability and Follow-Through (Overdoer) – “The Checklist Manifesto” by Atul Gawande
  3. Listening and Feedback Acceptance (Overdoer) – “Thanks for the Feedback” by Douglas Stone and Sheila Heen
  4. Strategic Planning (Overdoer) – “Good Strategy Bad Strategy” by Richard Rumelt
  5. Interpersonal Communication and Team Leadership (Overdoer) – “Leaders Eat Last” by Simon Sinek
  6. Delegation (Overdoer & Perfectionist) – “Multipliers” by Liz Wiseman
  7. Networking and Collaboration (Overdoer) – “Never Eat Alone” by Keith Ferrazzi
  8. Financial Management (Overdoer) – “Profit First” by Mike Michalowicz
  9. Proactive Planning (Crisis-Maker) – “The 7 Habits of Highly Effective People” by Stephen R. Covey
  10. Risk Assessment (Crisis-Maker) – “Risk Savvy: How to Make Good Decisions” by Gerd Gigerenzer
  11. Emotional Regulation (Crisis-Maker & Perfectionist) – “Emotional Agility” by Susan David
  12. Negotiation Skills (Defier) – “Getting to Yes” by Roger Fisher and William Ury
  13. Adaptability (Defier) – “Adaptability: The Art of Winning in an Age of Uncertainty” by Max McKeown
  14. Conflict Resolution (Defier) – “Difficult Conversations” by Bruce Patton, Douglas Stone, and Sheila Heen
  15. Self-Regulation (Defier) – “Willpower: Rediscovering the Greatest Human Strength” by Roy F. Baumeister and John Tierney
  16. Collaborative Skills (Defier) – “Collaboration: How Leaders Avoid the Traps, Create Unity, and Reap Big Results” by Morten T. Hansen
  17. Influence and Persuasion (Defier) – “Influence: The Psychology of Persuasion” by Robert B. Cialdini
  18. Flexibility (Perfectionist) – “Antifragile: Things That Gain from Disorder” by Nassim Nicholas Taleb
  19. Risk-Taking (Perfectionist) – “Originals: How Non-Conformists Move the World” by Adam Grant
  20. Self-Compassion (Perfectionist) – “Self-Compassion: The Proven Power of Being Kind to Yourself” by Kristin Neff
  21. Setting Realistic Goals (Perfectionist) – “Smarter Faster Better: The Secrets of Being Productive in Life and Business” by Charles Duhigg
  22. Prioritization (Perfectionist) – “Essentialism: The Disciplined Pursuit of Less” by Greg McKeown
  23. Accepting Feedback (Perfectionist) – “Mindset: The New Psychology of Success” by Carol S. Dweck
  24. Balancing Work and Life (Perfectionist) – “Off Balance: Getting Beyond the Work-Life Balance Myth to Personal and Professional Satisfaction” by Matthew Kelly
  25. Time Management (Perfectionist) – “Getting Things Done: The Art of Stress-Free Productivity” by David Allen
  26. Balancing Perfectionism with Practicality (Perfectionist) – “Good Enough: The Tolerance for Mediocrity in Nature and Society” by Daniel S. Milo
  27. Creativity and Innovation (Dreamer) – “The Creative Habit: Learn It and Use It for Life” by Twyla Tharp
  28. Practical Implementation (Dreamer) – “Making Ideas Happen: Overcoming the Obstacles Between Vision and Reality” by Scott Belsky
  29. Focus and Concentration (Dreamer) – “Focus: The Hidden Driver of Excellence” by Daniel Goleman