30 Hard Hitting Questions for Entrepreneurs to ReSet for Success

Absolutely — a brutally honest self-audit can be a game-changer for entrepreneurs.

Here's a list of 30 hard-hitting questions to help any self-employed entrepreneur confront the real issues and reset for success.

1. What time do I start work each day — and is it consistent?

2. How many proactive calls or messages to prospects did I make this week?

3. How many meetings did I have with decision-makers in the past 7 days?

4. Are my short- and long-term goals written down, clear, and measurable?

5. Do I review my goals daily, weekly, and monthly?

6. How many hours of actual focused, high-impact work do I do each day?

7. Am I spending more time consuming or creating?

8. How do I structure my day — do I follow a clear routine or just ‘react’?

9. How often am I distracted by low-value tasks or social media?

10. Do I regularly track KPIs and metrics that drive my business forward?

11. Am I crystal clear on my ideal client avatar?

12. Is my offer clearly solving a painful problem or fulfilling a strong desire?

13. Do I truly believe in the value and transformation I provide — and can I articulate it with conviction?

14. How often am I sharing stories and case studies that prove my value?

15. Am I consistently asking for referrals, testimonials, and introductions?

16. Am I positioning myself as an expert using content, authority, and thought leadership?

17. What’s my personal brand saying about me online right now?

18. How much am I investing in my own learning, coaching, or mentoring?

19. Am I working on my business or just in my business?

20. When was the last time I innovated, created a new offer, or tested a new strategy?

21. How much of my time is being wasted on things I could outsource or automate?

22. Am I truly holding myself accountable — or just making excuses?

23. How many hours of quality sleep am I getting consistently?

24. What is my daily/weekly physical exercise routine like?

25. Am I feeding my brain and body with the fuel it needs — or just surviving on caffeine, sugar, and stress?

26. What habits are dragging me down or keeping me stuck?

27. Do I feel joy, purpose, and alignment with what I do — or just pressure and survival?

28. Who do I surround myself with — growth-minded people or energy vampires?

29. If my current habits continue for the next 12 months, where will I be?

30. If I were coaching myself — what would I tell myself to do differently, starting tomorrow?

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