When Is It Time to Go All In?

Do you have a side hustle? Do you want to make it a full-time hustle, and escape your 9-to-5 job?

Starting a side hustle can be both exhilarating and daunting. The idea of turning your passion project into a full-time career and leaving the confines of a traditional 9-to-5 job is a dream many harbor. But when is the right time to take the leap and go all in?

While I worked at Microsoft, I started Henson Group as my side hustle. It wasn't an immediate "I'm going to quit Microsoft" decision. I had bills to pay and responsibilities to manage, so I began plotting my way forward. Here’s how my journey unfolded and how you can navigate yours.

The Beginnings of Henson Group

I started Henson Group in my tiny one-bedroom apartment in NYC after 9/11. I was the first and only employee for the first nine months. ?Now we have offices, employees, partners, and clients?worldwide.? After the 9/11 attack, I volunteered to help businesses rebuild and relocate out of lower Manhattan. Once these companies were up and running, they started hiring?me to build and maintain their IT. That’s when I started Henson Group on the side, dedicating my evenings and weekends to building the foundation of my business. It was challenging to balance both roles, but I knew that patience and strategic planning were crucial.

Revenue as a Signpost

Initially, it was about testing the waters and validating my business idea. I monitored every small success and used it as fuel to push harder. When revenue started coming in steadily, it was a clear sign that Henson Group had the potential to be more than just a side project. This steady income was my green light, indicating it might be time to consider going all in.

Making the Leap

The decision to leave Microsoft wasn't taken lightly. I meticulously planned my exit strategy, ensuring I had a financial cushion and a solid business plan in place. When I finally made the jump, it was a calculated risk backed by months of preparation and growing revenue.

The Result

The transition from a side hustle to a full-time business paid off immensely. Henson Group grew into an international company, and three years ago, I retired, leaving behind a legacy. Today, Henson Group boasts over 500 customers with over $50 million in ARR.

Your Path to Going All In

Here are some steps to help you transition your side hustle into a full-time venture:

• Validate Your Idea: Before making any big moves, ensure your side hustle has potential. Test your product or service in the market, gather feedback, and make necessary adjustments.
• Financial Planning: Build a financial cushion that can support you during the transition period. Calculate your monthly expenses and ensure you have at least 6-12 months' worth of savings.
• Set Milestones: Establish clear revenue and growth milestones. These will serve as indicators of when it might be time to transition to your side hustle full-time.
• Strategic Planning: Create a detailed business plan outlining your vision, target market, revenue streams, and growth strategy. This plan will be your roadmap during the transition.
• Gradual Transition: If possible, reduce your hours at your full-time job before quitting entirely. This gradual shift can help you adjust and dedicate more time to your side hustle.
• Build a Support System: Surround yourself with mentors, peers, and a network of supporters who can offer advice and encouragement during your journey.
• Go All In: When the revenue from your side hustle becomes consistent and surpasses a sustainable threshold, and when you feel confident in your business plan and financial stability, take the leap.

Conclusion

Turning a side hustle into a full-time career requires careful planning, patience, and determination. By validating your idea, planning financially, and setting clear milestones, you can navigate the transition successfully. Remember, going all in is a calculated risk, but with the right preparation, it can lead to unparalleled rewards.

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