25 Questions to Ask Yourself About Success and Happiness

In our pursuit of success and happiness, self-reflection is a crucial yet often overlooked practice. By asking the right questions, we can better understand what these concepts mean on a personal level and chart a path that leads to a fulfilling and successful life. Here are 25 questions, inspired by research studies, books, and examples from various countries and fields, that can help you shape a life that is not only successful by external standards but also deeply fulfilling.

1. What Does Success Mean to You?

Success is deeply personal and varies greatly from person to person. In Japan, the concept of ikigai—finding purpose or meaning in life—illustrates that success isn’t just about financial gain but also about personal fulfillment. In contrast, in Western cultures, success is often measured by achievements and status. Stephen Covey, in The Seven Habits of Highly Effective People, emphasizes the importance of defining success on your own terms rather than letting society dictate what it should be. Whether success means financial security, work-life balance, or making a positive impact, identifying your unique definition is crucial.

2. What Does Happiness Look and Feel Like?

Happiness is not just about fleeting moments of joy but about cultivating lasting well-being. Bhutan’s Gross National Happiness index measures prosperity by gauging citizens’ happiness rather than focusing solely on economic indicators. Martin Seligman’s PERMA model—Positive Emotion, Engagement, Relationships, Meaning, and Accomplishment—suggests that true happiness is a blend of these elements. Reflecting on when you felt most content can help you understand the components that contribute to your happiness.

3. Who Are Your Role Models for Success?

Role models play a critical role in shaping our aspirations. Consider Malala Yousafzai’s journey in Pakistan, where she became a global advocate for education despite the dangers she faced. Similarly, New Zealand’s Prime Minister Jacinda Ardern has been praised for her empathetic leadership. Research in social learning theory by Albert Bandura suggests that observing and emulating the behaviors of role models can significantly influence our own actions and decisions.

4. Do You Have a Personal Success Plan?

Having a clear plan is akin to having a roadmap that guides you toward your goals. In South Korea, the rigorous education system emphasizes planning and discipline, which has contributed to the country’s technological advancements and economic success. Tim Ferriss, in The 4-Hour Workweek, stresses the importance of setting actionable goals. Studies in goal-setting theory, particularly by Edwin Locke and Gary Latham, show that specific, challenging goals lead to higher performance.

5. How Do Your Current Responsibilities Make You Feel?

Assessing your current responsibilities is key to understanding your emotional and psychological well-being. In Finland, where work-life balance is highly valued, people are encouraged to pursue roles that align with their values and provide satisfaction. Mihaly Csikszentmihalyi’s concept of “flow”—a state of deep engagement and satisfaction—suggests that aligning your roles with your ability to achieve flow can lead to greater fulfillment.

6. If There Were No Obstacles, What Would You Need to Do to Find Success?

Visualizing a path without obstacles can clarify your true desires. Carol Dweck, in Mindset: The New Psychology of Success, argues that adopting a growth mindset can help you overcome perceived limitations. In countries like Israel, where innovation thrives despite limited resources, the ability to envision possibilities beyond constraints has led to breakthroughs in technology and science.

7. What Are the Main Challenges You Face in Your Day-to-Day Life?

Identifying challenges is the first step toward overcoming them. Charles Duhigg, in The Power of Habit, explains how habits shape our lives and how understanding challenges can help us address the habits that may be holding us back.

8. Is There Anything You Could Be Doing to Help Navigate Those Challenges?

Strategizing ways to overcome challenges is essential. Angela Duckworth, in her book Grit: The Power of Passion and Perseverance, emphasizes the importance of resilience. In Brazil, where socio-economic challenges are prevalent, the concept of jeitinho—finding a way—illustrates the importance of creativity and persistence in navigating obstacles.

9. Are There Any People in Your Life Who You Could Reach Out to for Help?

Building a support system is crucial. In African cultures, the concept of Ubuntu—”I am because we are”—highlights the importance of community and support networks. Robert Putnam, in Bowling Alone: The Collapse and Revival of American Community, emphasizes the value of social capital in achieving success. Identifying and reaching out to your support system can provide the resources and encouragement you need.

10. What Are Some Things You Currently Do That Contribute to Your Productivity, Happiness, and Success?

Recognizing your strengths and positive habits is key to building on them. In Denmark, known for its high levels of happiness, people prioritize routines that promote well-being, such as cycling to work and enjoying communal meals. James Clear, in Atomic Habits, discusses how small, consistent actions lead to significant changes over time.

11. What Time of Day Are You at Your Best?

Understanding your biological rhythms can enhance your productivity. In Spain, the tradition of siesta acknowledges natural energy cycles, promoting rest during the afternoon lull. Daniel Pink, in When: The Scientific Secrets of Perfect Timing, explores how aligning tasks with your energy levels can improve performance.

12. What Are You Doing During This Time of Day?

Maximizing your productivity during peak hours is crucial. The Japanese concept of Kaizen—continuous improvement—emphasizes the importance of making the most of your productive time. The Eisenhower Matrix, popularized by Stephen Covey, helps prioritize tasks by urgency and importance, ensuring that your peak hours are used effectively.

13. Are There Any Things You Can Do to Capitalize on Your Most Productive Time of Day?

Maximizing productivity during your peak hours can lead to significant gains. Cal Newport, in Deep Work: Rules for Focused Success in a Distracted World, advocates for setting aside uninterrupted time for focused work. In Germany, known for its efficiency, workplaces often schedule important meetings and tasks during peak productivity hours to maximize output.

14. How Many People Count on You on a Daily Basis?

Understanding your responsibilities can help manage your time and energy. In cultures with strong family values, such as Italy, where extended families often live together, balancing personal goals with helping others is key to fulfillment. Adam Grant, in Give and Take, discusses how those who balance personal goals with altruism often achieve greater success and satisfaction.

15. Can You Schedule Some Time to Recenter or Refresh?

Taking time to refresh is crucial for maintaining mental health. In Sweden, the concept of fika—a coffee break to relax and socialize—is a daily practice that promotes well-being. Arianna Huffington, in Thrive, emphasizes the importance of taking breaks to rejuvenate the mind and body, helping you stay focused and energized.

16. Do Your Regular Practices Give You Time to Grow and Learn in Your Industry?

Continuous learning is essential for staying competitive. In Singapore, a nation known for its emphasis on education, lifelong learning is encouraged through government initiatives. Peter Drucker, in The Effective Executive, highlights the importance of ongoing education and self-improvement to remain effective in your career.

17. Does Your Daily Routine Promote Your Health, Wellness, and Happiness?

Health and wellness are foundational to success. In Norway, where outdoor activities and work-life balance are highly valued, maintaining health is integral to personal and professional success. Shawn Achor, in The Happiness Advantage, presents research showing that positive emotions and a healthy lifestyle significantly enhance productivity.

18. What Are the Top Three to Five Things You’d Like to Prioritize in Your Daily Life?

Prioritization is key to managing your time effectively. In Israel, the concept of chutzpah—audacity or boldness—often leads people to focus intensely on their goals, prioritizing actions that lead to success. Greg McKeown, in Essentialism, argues that focusing on the essential tasks and eliminating the non-essential leads to greater success and satisfaction.

19. Do You Have Any New Short-Term or Long-Term Goals Regarding Your Success and Happiness?

Setting goals is powerful for directing your efforts. In China, the emphasis on long-term planning and diligence is evident in the country’s rapid development and success in various fields. Research by Locke and Latham in goal-setting theory suggests that specific, challenging goals are more likely to lead to higher performance.

20. Would a Schedule Help You Stay on Track?

Creating a schedule can help you manage time effectively. In Switzerland, known for its precision and punctuality, scheduling is a cultural norm that contributes to the country’s efficiency. Cal Newport’s time-blocking method, as discussed in The Time-Block Planner, is an effective way to allocate time for focused work and personal activities.

21. Are There Ways to Make Yourself Accountable for Meeting Your Goals?

Accountability is crucial for staying on track. Gretchen Rubin, in The Four Tendencies, discusses how different personality types respond to accountability, suggesting tailored strategies for staying committed to goals.

22. How Do You Handle Setbacks?

Resilience in the face of setbacks is key to success. In Nigeria, the concept of resilience is often reflected in the entrepreneurial spirit of its people, who continue to innovate despite economic challenges. Angela Duckworth’s concept of “grit” highlights the importance of perseverance and passion in overcoming challenges. Reflecting on how you’ve handled setbacks in the past can help you develop strategies for maintaining your motivation and drive when obstacles arise.

23. What Motivates You and Incentivizes You When You Have a Goal?

Understanding your motivations is essential for sustaining effort over the long term. In Argentina, the passion for football often serves as a powerful motivator for personal and national pride, driving individuals to pursue excellence on and off the field. Daniel Pink, in Drive: The Surprising Truth About What Motivates Us, identifies autonomy, mastery, and purpose as the key drivers of motivation. Recognizing what incentivizes you—whether it’s rewards, recognition, or personal satisfaction—can help you stay focused and committed to your goals.

24. Do You Currently Use Any Strategies for Staying Positive?

Maintaining a positive mindset is crucial for success and well-being. In India, the practice of yoga and meditation has long been used to cultivate positivity and inner peace, contributing to a balanced and resilient outlook on life. Barbara Fredrickson, in Positivity, presents research showing that positive emotions broaden our thinking and enhance our ability to build resources. Strategies such as practicing gratitude, mindfulness, and positive affirmations can help you maintain a constructive outlook, even in challenging times.

25. How Do You Define and Pursue a Balanced Life?

The final question encourages you to think about balance in your life. In Bhutan, the philosophy of Gross National Happiness prioritizes a holistic approach to development, balancing material progress with spiritual and emotional well-being. Similarly, in Scandinavian countries, the concept of hygge promotes comfort, coziness, and contentment, emphasizing the importance of balancing work and leisure. Balancing your personal and professional lives is crucial for long-term success and happiness. It involves making deliberate choices about how you spend your time and energy, ensuring that you nurture both your ambitions and your well-being.

Conclusion: The Power of Reflection in Shaping Success and Happiness

These 25 questions are not just reflective exercises; they are powerful tools for aligning your actions with your personal definitions of success and happiness. By drawing on insights from psychology, productivity, and well-being literature, and by reflecting on real-life examples from various countries and fields, you can gain a deeper understanding of what drives you and how to achieve your goals.

Success and happiness are deeply intertwined, and by regularly revisiting these questions, you can ensure that your journey remains fulfilling and true to your aspirations. Whether you are just starting out on your path or are well along the way, these questions can help guide you toward a life that is both successful and deeply satisfying.

About The Author:

Mukesh Jain has been a civil servant belonging to the Indian Police Service, with rich administrative experience and brilliant academic background.  A Gold Medallist Engineer in Electronics and Telecommunication Engineering from MANIT Bhopal, he obtained my MBA from the Indian Institute of Management Ahmedabad.  He also obtained his Master of Public Administration from the Kennedy School of Government, Harvard University along with Edward Mason Fellowship. Mukesh Jain has the unique distinction of receiving three distinguished awards at Harvard University: The Mason Fellow award and The Lucius N. Littauer Fellow award for exemplary academic achievement, public service & potential for future leadership. He was also awarded The Raymond & Josephine Vernon award for academic distinction & significant contribution to Mason Fellowship Program.  Mr Jain received his PhD in Strategic Management from Department of Management Studies, Indian Institute of Technology, Delhi.

Mukesh Jain has published many academic papers in international journals and have been a prolific contributor to national journals on the subjects of governance, happiness and public policy.    His book, ‘Excellence in Government: A Blueprint for Reinventing the Government’, is a recommended reading for many public policy courses. His book- “A Happier You: Strategies to achieve peak joy in work and life using science of Happiness”, received book of the year award in 2022.   After this, two more books, first, ‘A Masterclass in the Science of Happiness’ and the other, ‘Seeds of Happiness’, have also been received very well. He is a visiting faculty to many business schools and reputed training institutes of India and is an expert trainer of “Lateral Thinking”, and “The Science of happiness” and has conducted more than 300 workshops on these subjects.

For Happiness workshops and Keynote speaker assignments, he can be reached at mukesh.harvard@gmail.com