Is It Time to Go All In on Your Side Hustle? Here’s How to Know

Do you have a side hustle you’re passionate about? Ready to make it your full-time gig and leave your 9-to-5 behind? While exciting, the decision to fully commit to your side hustle requires careful consideration and strategic planning.

When I was at Microsoft, I started Henson Group as a side hustle. I didn’t just jump into it; I took calculated steps to ensure it would be successful. Let me share my journey and how you can apply similar strategies to know when it’s time to go all in.

The Birth of Henson Group

I founded Henson Group in my one-bedroom NYC apartment right after 9/11. Volunteering to help businesses recover and rebuild from the attack, I soon found myself in demand for IT services. This led to my side hustle, where I spent evenings and weekends building the foundation of my business. Like any side hustle, it was challenging to balance both roles, but my patience and planning were key to eventually going all in.

Key Signs: When to Take the Leap

1. Revenue Growth: The first green light for me was seeing consistent revenue. When Henson Group started bringing in steady income, I knew it had the potential to become more than a side project.

2. Financial Cushion: Before leaving Microsoft, I made sure to have a solid financial cushion. It’s essential to have 6-12 months of savings to support yourself during the transition.

3. Market Validation: I continuously tested my services and gathered feedback to validate that Henson Group wasn’t just viable but could scale.

   
   

Taking the Leap: My Exit Strategy

When I finally left Microsoft, it wasn’t an overnight decision. I had a clear exit strategy—including a detailed business plan and consistent revenue flow. This transition was a calculated risk, but my preparation made it manageable.

The Results of Going All In

Today, Henson Group is an international success, with over 500 customers and $50 million in ARR. The decision to go full-time with my side hustle paid off, but it was backed by strategic steps and financial planning.

Steps to Help You Transition

Here are actionable steps to help you decide when it’s time to commit full-time to your side hustle:

1. Validate Your Idea: Make sure your product or service has a market. Gather feedback and make adjustments as needed.

2. Financial Planning: Build a cushion that covers at least 6-12 months of expenses to ease your transition.

3. Set Milestones: Establish clear revenue and growth milestones. When you hit them, consider it a sign to go all in.

4. Create a Business Plan: Your plan should outline your vision, target market, revenue streams, and growth strategy.

5. Gradual Transition: If possible, reduce your hours at your full-time job before quitting entirely to ease into your side hustle.

6. Build a Support System: Surround yourself with mentors and peers who can offer advice and encouragement along the way.

7. Take the Leap: Once your revenue is stable, and you feel confident in your business plan, make the jump.

Conclusion: Trust the Process

Going all in on your side hustle is a big decision that requires patience, planning, and trust in your abilities. By validating your idea, planning financially, and setting clear milestones, you can make a calculated transition. With the right preparation, the rewards can be life-changing.

Embrace the journey and trust yourself—when the time is right, take the leap and go all in.