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How to Build a $150K Side Hustle While Working a 9-to-5: The 5-Year Playbook

How to Build a $150K Side Hustle While Working a 9-to-5: The 5-Year Playbook

·7 min read

Learn how to build a side hustle while working full time. This 5-year playbook covers scheduling, 4-day work weeks, and profitable side project ideas for 2024.

The dream of quitting the daily grind is universal, but the reality of the leap is often terrifying. Most aspiring entrepreneurs believe they have to choose between the security of a paycheck and the potential of a startup. However, as the story of Chris and his app, Wishlist, proves, you don’t need to quit your job to build a $150,000-a-year business. In fact, maintaining a side hustle while working full time is often the safest and most strategic way to ensure long-term success. By the time Chris finally handed in his resignation in July 2025, he had already scaled his project to 1.1 million registered users and 110,000 monthly active users. This wasn't an overnight success; it was a five-year masterclass in discipline, seasonal productivity, and the marathon mindset.

The 'Morning and Night' Schedule: Finding Your 4 Hours

Morning Night Schedule
Stormy AI post tracking and analytics dashboard

Managing a high-growth project alongside a 9-to-6 career requires a surgical approach to your calendar. Chris didn't rely on bursts of inspiration; he relied on a rigid work-life balance for founders that prioritized incremental progress. His day started at 8:00 AM with one hour dedicated to low-intensity tasks: answering support emails, checking Firebase analytics, and managing the community. This "warm-up" ensured the business stayed operational before his corporate responsibilities took over.

The real heavy lifting happened from 8:00 PM to 11:00 PM. After his 9-to-6 job and a block for personal time or sports, Chris would dive back into development. While this sounds grueling, the key is the separation of tasks. Mornings are for maintenance; nights are for deep work. To stay competitive in 2024, many founders are now using Stormy AI's post tracking to monitor their app's social mentions and engagement while they are at their day jobs, allowing them to react quickly during their evening work blocks.

Finding Profitable Side Project Ideas Without Overcomplicating

Finding Profitable Ideas
Stormy AI search and creator discovery interface

One of the biggest hurdles to starting is the search for the "perfect" idea. Chris suggests that profitable side project ideas are often hidden in plain sight—usually as simpler, prettier versions of existing tools. He didn't try to build the next Facebook; he built a wish list app because he was tired of using a Microsoft Excel sheet to track Christmas gifts. He recognized that if he had a problem, at least one other person on Earth did too.

For those looking to enter the creator economy or launch a niche service, Stormy's AI search and discovery is a powerful tool for market research across TikTok, YouTube, and Instagram. By searching for creators in specific niches, you can identify what problems their audiences are complaining about, effectively finding a gap in the market before writing a single line of code. Chris's goal wasn't a million dollars initially; it was simply to have one random person download the app. This low-pressure entry point is essential for anyone learning how to quit your 9-5 without the stress of immediate monetization.

If I had set my goal six years ago to have 150K a year, I would have thrown away that project. Aim for one stranger's download first.

Leveraging Growth for a Four-Day Work Week

Four Day Work Week

As your side project begins to generate passive income streams in 2024, your day job shouldn't be seen as an obstacle, but as leverage. By early 2025, Chris had scaled Wishlist to the point where he could negotiate a four-day work week with his employer. This transition is a critical bridge. It provides a full, uninterrupted day for your business while maintaining the safety net of a salary and benefits.

To reach this stage, you must demonstrate that your side project makes you a better employee. Chris was upfront with his employer about Wishlist from the start. He framed it as a mutually beneficial learning environment. Because he was building an app from scratch, he learned about Flutter, RevenueCat, and user authentication in ways he never would have at a specialized 9-to-5 role. This cross-pollination of skills makes you indispensable at work while you build your exit strategy.

The Seasonal Productivity Hack: Winter Coding

Burnout is the primary reason side hustles fail, according to recent studies on entrepreneurial mental health. Chris avoided this by leaning into "seasonal productivity." During the summer months, motivation often wanes when the weather is nice. Instead of fighting it, Chris focused his heaviest development cycles during the winter. In the colder months, the social pressure to be outside is non-existent, making it the perfect time for a winter coding sprint.

Additionally, he utilized "working holidays." By traveling with a small group of motivated peers to hubs found on Nomad List, he combined social interaction with productivity. For founders today, managing these relationships and finding the right people to collaborate with can be automated. Using Stormy's AI outreach, you can find and connect with other developers or creators in your niche to organize these types of working retreats, ensuring you stay motivated and mentally healthy.

The winter is your secret weapon. No one asks why you're inside coding when it's freezing outside.

Marketing on a Budget: The Power of Reviews

As a developer, Chris admitted he was "naturally bad at marketing." He didn't have a massive budget for Google Ads, so he focused on the App Store's most powerful currency: user reviews. He implemented a simple but effective strategy—asking for reviews only after a user had accomplished something, as positive review prompts significantly boost App Store rankings. This ensured the user was in a positive state of mind before the prompt appeared.

He also turned his support system into a growth engine. Every time a bug was fixed or a feature was added, he personally emailed the users who requested it. This hyper-personalization built a loyal community of 4,000+ paying customers. For those who aren't developers, Stormy's AI email inbox can handle this level of personalization at scale, allowing you to follow up with users or potential partners automatically while you sleep.

The 5-Year Marathon Mindset

Marathon Mindset

The most important takeaway from Chris’s journey is the timeline. We live in an era of "vibe coding" and weekend launches, but a sustainable $150K business often takes years. Chris’s timeline was clear:

  1. 2019: Started building the first version.
  2. 2020: Released the first MVP.
  3. 2021: Got a job as an app developer (thanks to his side project).
  4. 2023: Relaunched Wishlist 2.0 with a cleaner codebase.
  5. 2024: Scaled to 1.1M users while working full time.
  6. 2025: Quit the 9-to-5 to go full time.
This marathon mindset is what separates successful founders from those who quit after three months. By viewing your side hustle as a long-term asset rather than a get-rich-quick scheme, you allow the compound interest of your efforts to build.

Final Takeaways for the Full-Time Founder

Building a side hustle while working full time is not just about the extra income; it’s about building a bridge to freedom. Chris’s story shows that you don’t need venture capital or a massive team to succeed. You need a simple idea, a consistent schedule, and the right tools to automate the heavy lifting. Whether it's using Cursor for AI-assisted coding or Stormy AI's influencer analysis for vetting potential marketing partners, the technology available in 2024 makes this journey more accessible than ever. Start small, stay honest with your employer, and remember: it’s a marathon, not a sprint. If you start today, where could you be in five years?

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