5 Painful Business Lessons Every CEO Needs to Learn (So You Donβt Have To)
Nov 19, 2024Running a 6- or 7-figure business is a thrilling yet relentless journey. Success is not a straight line—it’s a zigzag of wins, mistakes, and lessons learned. After 20 years of helping people achieve financial goals, 10 years building businesses, and 5 years as a business owner, I’ve made mistakes that no classroom could have prepared me for.
These hard-earned lessons have shaped how I lead, strategise, and scale—and now I’m sharing them with you.
Lesson 1: Your Team Won’t Care as Much as You Do
This truth hurts: No one will care about your business as much as you do. I used to believe that a large, motivated team was the secret to success. I hired without clear direction, assumed initiative, and poured money into payroll—only to realise my hires were spinning wheels, not driving growth.
What Went Wrong?
- I thought having a big team would help me avoid uncomfortable growth moments.
- I failed to set clear expectations or systems of accountability.
- I hired thinkers instead of doers, resulting in lots of ideas but no execution.
The Fix: Create SOPS & Hire for Specific Roles
Standard Operating Procedures (SOPs) are your secret weapon. They align your team with your business’s proven processes, ensuring tasks are done efficiently and correctly.
Watch my YouTube video on SOPs for detailed guidance.
Additionally, assess whether you need thinkers or doers. For rapid growth, hire doers who execute. Later, you can bring in strategic thinkers for long-term innovation.
Ready to scale your team smartly? Book a call or check out my coaching services.
Lesson 2: Diversify Your Client Pipeline
I once dedicated an entire quarter to serving one major client. While the results were incredible, the project ended—and I faced a painful revenue gap. Putting all your eggs in one basket leaves you vulnerable to financial uncertainty.
What Went Wrong?
- I focused solely on delivering to one client, neglecting to nurture new leads.
- I didn’t build a system to maintain a steady pipeline of prospects.
The Fix: Balance Clients & Build a CRM
- Set Boundaries: Allocate time to acquire new clients while serving existing ones.
- Use a CRM System: Track leads and keep your funnel consistently full.
Need help structuring your client pipeline? Explore the Business Success Formula.
Lesson 3: Launch Before You’re Ready
Fear of imperfection delayed my first course launch for four years. I believed I needed more certifications, more knowledge, and more confidence. The truth? Confidence comes from doing, not waiting.
What Went Wrong?
- I wasted years hesitating, doubting whether I was “ready.”
- I missed out on opportunities to learn and refine through real-world feedback.
The Fix: Start Small with a Beta Launch
- Create a rough version of your offering and release it to a test audience.
- Gather feedback, iterate, and improve over time.
Since finally launching Prosperity Path, I’ve realised that taking imperfect action is far more valuable than waiting for perfection.
Struggling to launch? Check out Prosperity Path for strategies to overcome self-doubt and grow your income.
Lesson 4: Trust Yourself Over Random Opinions
When my confidence was low, I let external opinions guide my business decisions—even from people outside my industry. I constantly changed my offerings to suit their ideas, only to realise they weren’t my target audience.
What Went Wrong?
- I pivoted my business strategy based on advice from people who didn’t understand my goals.
- This constant change confused potential clients and delayed growth.
The Fix: Stick to Your Expertise & Vision
- Design offerings based on your expertise and your clients’ needs—not random feedback.
- Give your strategies time to gain traction before making adjustments.
Feeling stuck? Learn how to trust your vision with my coaching services.
Lesson 5: Strategy Alone Isn’t Enough
For years, I thought strategy was the magic bullet. I focused on step-by-step plans, ignoring the emotional and mental challenges my clients faced. What I missed was this: Growth is as much about mindset as it is about execution.
What Went Wrong?
- Clients hit emotional roadblocks I hadn’t equipped them to navigate.
- I neglected to address the mental resilience needed for sustainable growth.
The Fix: Combine Strategy with Mindset Coaching
Growth isn’t just structured—it’s emotional. Teach your clients how to handle fear, overwhelm, and resistance while implementing your strategies. The same goes for your own business journey.
Need mindset strategies for growth? Watch my videos or book a call to start transforming your approach.
Concluding Thoughts: From Mistakes to Mastery
Every mistake I’ve made has taught me invaluable lessons. They’ve shaped how I lead and helped me grow into a more resilient, effective business owner. The good news? You don’t have to make the same missteps.
If you’re ready to:
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Build a smarter team
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Diversify your client pipeline
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Launch with confidence
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Stay true to your vision
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Combine strategy with mindset
Let’s work together to unlock your business’s potential.
- Book a call to discuss your goals.
- Check out my Free Business Blueprint for actionable strategies.
- Explore coaching or view my work on Upwork.
Your success is waiting—let’s build it together.
Check Out Prosperity Path
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