Real Talk About Making Smart Moves on the Side Reaching Level Two means you've already moved past just thinking about making more money. You're not stuck in the "someday" loop anymore. You’ve decided to take on more work outside your 9-to-5. That alone deserves credit. This is when things start to get real. You’re balancing your main job with something else, and now your discipline is being tested. It's a major turning point because you're shifting how you think about time, income, and effort. Not All Side Hustles Are Worth It At this stage, it’s tempting to just grab whatever pays. But here’s the deal: not every side hustle is going to help you long term. Picking up another hourly job might help you in the short run, but it won’t take you very far. That kind of work keeps you tied to the clock. You work, you get paid. You don’t work, the income stops. Instead, look for something performance-based. Think about jobs where the results you create determine how much you earn. Things like real estate, freelance gigs, consulting, personal training, or even DJing. These push you to handle your own clients, follow up on leads, and actually sell your value. That’s where real growth happens. Build Skills That Outlast the Hustle When you take on a hustle that depends on results, you get a crash course in sales, communication, and persistence. You learn fast because the feedback is instant. Either you close the deal, or you don’t. You get hired, or you don’t. That kind of environment teaches you way more than any fixed-wage job. It forces you to show up, improve, and learn how to deal with failure without falling apart. Those are skills you’ll use forever. Don’t Just Work More. Work Smarter. If you’re in survival mode and need extra money just to cover the basics, do what you have to do. Take that second job. But make sure you don’t stay there. Treat it like a stepping stone, not a long-term solution. Use this time to test ideas. Try out different skills. Go to a quiet place, bring a notebook, or open a doc on your phone. List out a few things you’re good at or enjoy doing. Pick one and test it. If it doesn’t stick, adjust and try again. Just make sure you keep your finances under control while you do it. Cut back on expenses if you have to. If your lifestyle costs more than what your main job and side hustle bring in, something has to give. Better to downsize now than to be stuck working two jobs five years from now. Think Long-Term Value The goal is to move toward a hustle that builds something you can grow. You want to be in a position where people are paying you because of your specific skills or experience. Driving for a rideshare app might be flexible, but the company does most of the heavy lifting. You’re filling a spot in a system. But if you’re offering your own service or product, you’re building something that’s yours. It might be slower at first, but over time it creates real freedom. Real Examples Make a Difference You can learn a lot by paying attention to people who’ve already walked this path. Folks like Ashkan Rajaee have shared insights on navigating side hustles and shifting into ownership mindsets. You don’t have to follow anyone's path exactly, but there’s a lot to take in from those who've done the work. Final Thought This phase isn't easy. You’ll be tired. Some days will feel like you're going nowhere, but you're learning and building muscle, both mentally and emotionally. That counts. There’s no perfect side hustle. But there is a smart way to go about it. Choose something that teaches you, challenges you, and eventually pays you for who you are, not just what you do. Stick with it. Adjust as needed. And always keep your long game in mind. Keep going.

Walkthroughs, tutorials, guides, and tips. This story will teach you how to do something new or how to do something better.

Make

Choosing the Right Side Hustle That Actually Works

About Author

Comments

TOPICS

THIS ARTICLE WAS FEATURED IN

Related Stories

Final Destination's Sixth Installment Brings a Smart, Psychological Twist to Horror Tropes

What No One Told Me About Being a Product Manager at an Early Stage Startup

10x10: Ten Life Lessons from a Developer After Ten Years in the Industry

10 Things Every New Developer Should Know

10 Steps for Landing a Job at a Startup

10 Skills You Need For Your Post-Pandemic Career

Final Destination's Sixth Installment Brings a Smart, Psychological Twist to Horror Tropes

What No One Told Me About Being a Product Manager at an Early Stage Startup

10x10: Ten Life Lessons from a Developer After Ten Years in the Industry

10 Things Every New Developer Should Know

10 Steps for Landing a Job at a Startup

10 Skills You Need For Your Post-Pandemic Career

Light-Mode

Classic

Newspaper

Minty

Dark-Mode

Neon Noir

Minty

HN StartUps