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30 Hard Hitting Questions for Entrepreneurs to ReSet for Success

30 Hard Hitting Questions for Entrepreneurs to ReSet for Success

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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.

🔍 30 Hard Questions Every Entrepreneur Should Ask Themselves
  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?

Get your copy of the Hard Hitting Worksheet here - click here

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