SHS032: The Key To Developing Confidence As A Freelancer In 2026!
Intro
Season 2 of The Side Hustler’s Society is officially underway, and while this season is focused on lead generation, there’s something even more important that needs to be addressed first:
👉 Boldness
Because here’s the reality…
👉 You can have all the leads in the world, but if you’re too afraid to act on them—you won’t make any money.
In this episode, Elijah Bilel breaks down why boldness is the real foundation of success in business, freelancing, and sales.
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Episode Overview
In this episode, you’ll learn:
- What a lead actually is and why it matters
- Why boldness comes before strategy
- How fear and rejection hold people back financially
- The connection between confidence and income
- The framework for developing boldness in your life
Listen to the Episode
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Side Hustler’s Society Resources
Side Hustle to Full-Time Strategy Session
The Personalized Side Hustle Starter Kit
The Anatomy Of Financial Success Paperback
What Is a Lead (And Why It Doesn’t Matter Without Boldness)
Before diving deeper, Elijah defines a lead as:
👉 A potential customer or prospect for your product or service
But here’s the key insight:
👉 Leads don’t make you money…
👉 Closing them does
And to close them, you need:
- Confidence
- Communication skills
- The ability to handle rejection
Without boldness, even the best opportunities go to waste.
What Is Boldness?
Boldness is defined as:
👉 Your ability to:
- Take risks
- Face fear
- Handle rejection
- Act with confidence
It also includes:
👉 Doing what most people are too afraid to do—even when the reward is high
Why Most People Struggle With Boldness
Most people are conditioned to:
- Avoid risk
- Seek comfort
- Follow structure
Which makes sense…
👉 The system trains people to be employees, not entrepreneurs
But in business?
👉 You have to step outside your comfort zone.
The Real Reason You Fear Rejection
Elijah breaks it down into three root causes:
- Lack of confidence in yourself
- Weak communication skills
- Insecurity about handling rejection
And here’s a powerful insight:
👉 If you struggle approaching people in life…
👉 You’ll struggle in sales too
There’s a direct connection between:
- Social confidence
- Sales ability
- Financial success
Boldness and Risk-Taking
Boldness isn’t just about talking to people.
It’s about:
👉 Taking action despite uncertainty
Examples include:
- Reaching out to potential clients
- Presenting your offer
- Speaking in public
- Building something new
And here’s the progression:
👉 1-on-1 conversations → Sales → Public speaking → Leadership
Each level requires more boldness.
The Personality Factor (Why Some People Struggle More)
Based on The Anatomy of Financial Success, different personalities have different levels of boldness.
Higher natural boldness:
- Sniper
- King of the Hill
- Fame Seeker
Lower natural boldness:
- Builder
- Conservative
- Preserver
👉 If you’re in the second group, this is a skill you must actively develop. Find out which one of the side financial personalities you are by our personlize side hustle kit that contains The Financial Personality Report here!
You Need a Goal to Be Bold
One of the most important points in this episode:
👉 You can’t be bold without direction
Example:
- If your goal is $100K/year
- And you know how many clients you need
- And you have a system to get them
👉 Now your actions have purpose
Without that?
👉 Fear wins every time
The MMA Story (How Boldness Changed Everything)
Elijah shares a powerful personal story about getting into MMA.
At the time, he was told:
👉 He had skill—but was still operating in his comfort zone
So he did something extreme:
👉 He trained in mixed martial arts for 6 months
And the result?
- Massive confidence boost
- Increased discipline
- Higher output and productivity
- Willingness to take risks
This period led to:
- Launching his first YouTube channel
- Growing The Veggie Outers community
- Writing The Anatomy of Financial Success in ~9 months
- Becoming a completely different version of himself
The 3 C’s of Boldness
Elijah introduces a simple but powerful framework:
1. Constitution
Your physical and mental state
👉 Energy, discipline, and resilience
2. Confidence
Your belief in your ability to handle situations
👉 Built through action and experience
3. Charisma
Your ability to connect with people
👉 Critical for sales and communication
It All Starts With Self-Image
At the root of boldness is:
👉 How you see yourself
If you don’t believe you’re capable…
👉 You won’t act
The solution?
👉 Do hard things
Even if they’re unrelated to business.
Because:
👉 Conquering one fear builds confidence across all areas
How to Develop Boldness
Key takeaway:
👉 You don’t “learn” boldness
👉 You build it through action
Examples:
- Try something that scares you
- Put yourself in uncomfortable situations
- Take small risks consistently
- Build momentum over time
Final Thoughts
Elijah Bilel makes one thing clear:
👉 Boldness is the gateway skill
Without it:
- You won’t take action
- You won’t close deals
- You won’t grow
With it:
👉 Everything else becomes easier
Watch The Podcast On Youtube!
