The 5 Stages of Your Leadership Journey as an Online Entrepreneur

Discover which of the 5 leadership stages you're in as an online entrepreneur and learn exactly what you need to do to level up your business.

The 5 Stages of Your Leadership Journey as an Online Entrepreneur

Are you struggling to scale your online business beyond just yourself? Discover where you are on the leadership journey and get the guidance you need to level up.

Understanding Your Leadership Journey

As online entrepreneurs, we all start somewhere. Whether you're just testing the waters with your business idea or you're already drowning in client work, knowing exactly where you stand on your leadership journey is crucial for moving forward strategically.

Think of it like using Google Maps—it can't direct you to your destination if it doesn't know your starting point. When your location services are turned off, the app becomes useless. Similarly, understanding your current leadership stage helps you identify what you need to focus on to reach your goals.

The 5 Stages of the Leadership Journey

After working with consultants, course creators, and mission-driven entrepreneurs for years, I've identified five distinct stages that every online business owner moves through. Let's explore each one:

Stage 1: The Hobbyist

You might be a Hobbyist if:

You work on your business only when you have spare time
You're excited about having a creative outlet but haven't made money yet
You're still experimenting and second-guessing your decisions
You question whether entrepreneurship is really for you

The Hobbyist stage is where we all begin. It's characterized by enthusiasm but limited commitment, and your business feels more like a side project than a serious venture.

Stage 2: The Starry-Eyed Hustler

You might be a Starry-Eyed Hustler if:

You're making some money, but not consistently
You feel overwhelmed by all the different business strategies you could try
You're "throwing spaghetti at the wall" without a clear plan
You haven't developed repeatable systems for sustainable income

At this stage, you've committed to your business but haven't found your rhythm yet. Success feels possible but unstable, and you're constantly searching for the "right" approach.

Stage 3: The Burned-Out Solopreneur

You might be a Burned-Out Solopreneur if:

You've built a relatively successful business but are doing everything yourself
You know exactly what your base income is each month
You're working long days and your brain is constantly overworked
Your mental or physical health is suffering because of your workload
You're questioning if the business is worth the toll it's taking on you

This is often where many entrepreneurs get stuck. You've proven your business model works, but you're trapped in it, unable to step away without everything falling apart.

Stage 4: The Boss Bitch

You might be a Boss Bitch if:

You've acknowledged you need help and started hiring team members
You have more time for family and no longer do tasks that don't grow the business
You feel proud of what you've built but find managing people frustrating
You catch yourself thinking, "Why can't they do their jobs right?"
You feel like you're wasting time explaining how to do tasks

At this stage, you've taken the leap to build a team, but you haven't mastered leadership yet. The relief of delegation is often overshadowed by new management challenges.

Stage 5: The Leader

You know you've become a Leader when:

You wake up excited to start your workday
You feel confident about your business and can relax on vacation
You're energized by collaborating with team members you fully trust
Your team operates with autonomy while maintaining high quality
You've created a workplace worthy of people's commitment

This is the ultimate goal—where your business operates smoothly with or without your constant involvement, and both you and your team thrive.

Why Most Entrepreneurs Get Stuck

If you're not where you want to be on this journey, you're not alone. Most online entrepreneurs struggle to transition through these stages because they:

Rely on intuition instead of proven systems - Managing people effectively is not intuitive for most of us
Use outdated hiring practices - The post-COVID workforce requires new approaches
Believe mindset is the only barrier - While important, mindset alone won't build systems
Copy corporate giants - What works for Disney or Apple rarely translates to small online businesses

Moving Forward: What You Really Need

To progress to the next stage of your leadership journey, you need:

Tools and systems you can implement easily without overthinking
Scripts and templates that eliminate guesswork in hiring and management
A framework for creating a team culture that attracts and retains top talent
Support from someone who understands the unique challenges of online business leadership

Remember that becoming a true leader happens when you've hired high-quality team members and can manage them in a way that motivates them to bring their best work every day.

Assess Your Leadership Readiness

Ask yourself these questions to determine where you stand:

Do I know how to hire the people I need?
Am I free from imposter syndrome about being a leader?
Can I hold effective meetings where everyone has a voice?
Do I know how to successfully onboard team members?
Can I make people feel valued as part of a team?
Do I know how to create 90-day priorities and keep everyone on track?
Can I coach my team members to excel and feel fulfilled?
Do I have the self-awareness to take care of myself while leading others?

If you answered "no" to any of these questions, you have clarity on what needs attention next.

Next Steps

Ready to level up your leadership journey? Here's what you can do:

Take the leadership quiz at worthofwork.com to identify your current stage
Schedule a free 30-minute call for personalized advice tailored to your situation
Listen to more episodes of Permission to Lead for deeper insights into each stage

Remember, your impact extends beyond just your clients. When you lead well, your positive influence ripples through your team members' lives and creates a lasting legacy far beyond what you could achieve alone.

Are you a Hobbyist, Starry-Eyed Hustler, Burned-Out Solopreneur, Boss Bitch, or Leader? Share your stage in the comments below and let me know what's your biggest challenge right now!

Categories: : business development, leadership, sustainable business, team building