20 Questions to Change Your Life

Measure What Matters

It’s a series of 20 questions. You give an answer between 1–5 for each question (1 = strongly disagree; 5 = strongly agree), then add the up to get a total score out of 100.

• 100/100 = You’re an unstoppable force of nature
• 60/100 = Decent, room for improvement
• 20/100 = You have no clue what you’re doing.

I got a pretty sobering score of 45/100 this week — way lower than I expected. But thinking about the questions I scored lowest on helped me uncover some personal blind spots. I might even use Chris’ questions as newsletter writing prompts for the rest of the year.

Without further ado, here are the questions:

🗺️ Vision

Are you designing a life in alignment with your top values?

1. Do you have a life mission you want to achieve?

2. Do you have a vision for your career?

3. Do you have a consistent long-term review process?
You regularly reserve time to review wins, lessons, and opportunities in your life and career.

4. Do you have a consistent long-term planning process?
You regularly reserve time to define objectives, set actionable goals, and reallocate resources.

5. Do you keep track of your projects?
You track progress on the things that are most important to you. You have defined deadlines and clear objectives.

🚦Prioritisation

Are you working on the most important things?

6. Do you plan and review your top priorities for the week?
You plan your weekly priorities in advance. You review progress at the end of each week.

7. Do you plan and review your top priorities for the day?
You know what you will work on before you get started. Your schedule is an accurate reflection of your day.

8. Do you work on your Top Priority first each day?
You know what you plan to accomplish and how you will get started. You delay email, phone, and reactive work until after your Top Priority.

9. Do you have control over your own schedule?
You have the ability to select your top priorities opportunistically. You can invest your time in what you think is most important.

10. Are you decisive?
You act quickly and decisively. You minimize procrastination on difficult or ambiguous tasks. You know how to to get yourself back on track.

🏭 Systems

Are you making what you want to do easier to do?

11. Do you leverage your time well?
You maximize your average hourly rate. You take steps to advance your career rather than just maintaining your position.

12. Do you manage and delegate well?
You document processes and streamline repeating tasks. You delegate lower-value tasks.)

13. Does your physical workspace inspire you?
Your workspace supports deep focus and separation from home and personal tasks.

14. Do you track important metrics?
If it is important to your life or career, you are tracking it. Examples: health, time, habits, finances, business.

15. Do you have systems for learning?
Your personal development is intentional and systematic. You follow programs to train effectively. Your environment and information diet reflect your goals.

🧘‍♂️ Presence

Are you showing up as your best self every day?

16. Do you start your day intentionally?
You have a consistent morning routine that sets a positive tone for the day. Examples: journaling, reading, planning, exercise, meditation, gratitude.

17. Are you focused?
You can concentrate on a single task. You minimize notifications and digital distractions. You check email and messages only at pre-selected times.

18. Do you prioritize your physical health?
You sleep well. You eat healthy food that makes you feel good. You regularly exercise and spend time outside. You minimize caffeine and alcohol consumption.

19. Do you prioritize mental health and recovery?
You take offline breaks. You have a diverse identity with hobbies and supportive friends. You have self-care practices to replenish your well-being.

20. Do you finish your days effectively?
You tie up loose ends at the end of the workday. Your evenings set tomorrow up for success. You have clear separation between work and your personal life.

Once you’ve got your final score, think about how to improve your weakest areas. You might want to check out Chris’ free workbook Experiment Without Limits, which includes a bunch of useful tools and frameworks.