25 Pros and 12 Cons of Running a Side Hustle: 37 Truths Nobody Tells You

Unexpected realities I learned after quitting my job to pursue my passion full-time.

I’ve been writing online for over eight years now.

It’s only been in the last 2 years that I started making money from it.

For the past 1.5 years, I’ve converted my writing side hustle into a profitable content marketing business.

In this post, I wanted to share some tips I’ve learned along the way — both the pros and cons — so that other creators, freelancers, and side hustlers can benefit from my experience.

I’ll discuss 25 pros and 12 cons of running a side hustle. These are the truths that nobody tells you — the good, the bad, and the ugly of running a business on the side.

I hope they will help you in your journey as a side hustler.

25 Pros of Running a Side Hustle

1. You get to work on your terms. Early bird or a night owl — you can pick your timetable.
2. When you share your own online, you can build a personal brand and establish yourself as a thought leader in your field.
3. The consequences of excellent work translate directly into more money and better business opportunities. This is different from working in a corporation, where your efforts only enrich the company.
4. You gain valuable feedback directly from your target audience. This can immensely improve and grow your side hustle.
5. You can take a vacation whenever you wish. The upside? You don’t have to miss important events and holidays because of work anymore.
6. You (mostly) make more money than your tech buddies, sometimes even more than your startup owner and entrepreneur friends.
7. Smart investments and building passive income sources mean you can make money even while you’re sleeping.
8. A successful side hustle instills confidence and makes you feel like you can overcome any hurdle life throws your way.
9. Razor-sharp focus in one dedicated skill helps you grow 10x.
10. As the owner, manager, and accountant of your business, you’re forced to cover multiple aspects of your side hustle. This teaches business skills and inculcates entrepreneurial values.
11. You get to see the impact of your work directly on people’s lives.
12. There’s tremendous potential to learn from failure and overcome challenges, making you more resilient and adaptable in your career journey.
13. You get to create a positive work-life balance by having a side hustle that complements your skills and interests.
14. Posting your experiences as a side hustler online can inspire and motivate others. You can build a loyal community of people leading amazing lives by following in your footsteps.
15. You develop a problem-solver attitude that boosts your confidence and self-esteem by taking on new challenges and achieving success.
16. By experimenting and finding your passion, you learn more about yourself and discover new talents you may not have known you had.
17. You gain control and agency over your life and career by building something from the ground up.
18. By actively seeking connections, you can develop a strong support network of like-minded individuals who share your interests and passions.
19. You’re forced to step outside your comfort zone by trying something new daily.
20. You learn to improve your time management and organizational skills by simultaneously balancing multiple commitments and responsibilities.
21. You can create new opportunities for networking and career advancement by building cohorts, collaborative projects, and budding relationships with other side hustlers and entrepreneurs.
22. You enjoy the freedom and flexibility to explore your interests without the constraints of a traditional job.
23. You get to develop a more well-rounded and diverse skill set that can make you more marketable in your career.
24. By regularly taking on new challenges and experimenting with unique ideas, you familiarize yourself with the multi-faceted demands of your target audience.
25. You can create a legacy and leave a lasting impact on the world by providing a valuable product or service that addresses a real need.

12 Cons of Running a Side Hustle

1. Discipline is everything. You chill for too long, and your bank account starts reflecting your laziness.
2. Every short vacation needs intense planning and preparation.
3. You run the risk of working too much and heading toward burnout.
4. It takes a long time to start earning money. There’s bound to be financial uncertainty and instability, especially in the early stages of your side hustle.
5. When you’re addicted, it’s hard to turn off your mind. Your brain is always coming up with ideas to grow your business further. Taking time off from your side hustle is hard.
6. You start relating less to your friends working in jobs, and making new friends with a similar lifestyle can get challenging.
7. Since most of your job involves sitting at a computer, sometimes, getting time outside in nature can be tricky.
8. There are fewer excuses to meet people in real life if your side hustle involves having an online business.
9. There’s always the potential for unrealistic expectations and disappointment if your side hustle doesn’t achieve the success you hoped for.
10. It’s challenging to check for all potential legal risks you might run into if your side hustle violates any laws or regulations or if you don’t manage your finances properly.
11. Envy is real. Your side hustler friends might get jealous of your success. The reverse is also true. If you don't learn to keep your jealousy in check, feelings of inadequacy and inferiority will darken the horizon.
12. You might lose identity and purpose if your side hustle becomes all-consuming and overwhelms the other aspects of your life.

I talked about several of the pros and cons of being a side hustler in detail in this video. Do watch it and let me know your thoughts in the comments.

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