The Fear of Regret: Why Staying in Your 9-to-5 Might Be Riskier Than Starting Your Own Business

By Jenna Hadden

Let’s get real for a moment. The comfort of a steady 9-to-5 job is alluring. The regular paychecks, the predictable routine, the sense of security—all of it feels safe. But here’s the hard truth: playing it safe might just be the riskiest move you can make. Why? Because nothing stings more than the regret of untapped potential and unpursued dreams.

Understanding the Risk of Regret

Regret is a powerful emotion, and it’s often tied not to what we did, but to what we didn’t do. Imagine looking back on your life and realising that the only thing holding you back from achieving greatness was your own fear. That’s the kind of regret that lingers, that keeps you up at night. When you choose to stay in your 9-to-5, you might be avoiding immediate risks, but you’re also avoiding the possibility of something greater. And that’s a risk that compounds over time.

The Illusion of Security

Your 9-to-5 might feel secure, but is it really? Job security is, in many ways, an illusion. Companies restructure, industries evolve, and what once felt like a stable job can disappear overnight. By staying in a job solely because it feels safe, you’re placing your future in someone else’s hands. On the other hand, starting your own business puts you in the driver’s seat. Yes, it’s risky, but it’s a risk where you control the outcome. You’re betting on yourself, and that’s a bet worth taking.

The Opportunity Cost of Inaction

Let’s talk about opportunity cost. Every day you spend in a job that doesn’t fulfil you is a day you’re not spending building something that could change your life. The time, energy, and creativity you invest in your 9-to-5 could be channelled into your own venture, something that aligns with your passions and goals. The cost of inaction isn’t just financial—it’s the loss of potential growth, innovation, and, ultimately, happiness.

Chasing Your Dreams vs. Settling for Less

Starting a business isn’t easy, and it’s not for everyone. But if you have that itch, that dream you can’t shake, settling for a job that doesn’t excite you is like sentencing yourself to a lifetime of mediocrity. The fear of failure is real, but the fear of never trying is even greater. Successful entrepreneurs aren’t fearless—they just understand that the pain of regret is far worse than the sting of failure.

Taking the First Step

If you’re still on the fence, start small. You don’t have to quit your job tomorrow. Begin by exploring your business idea on the side. Test the waters, gather feedback, and slowly build confidence. The key is to take action, however small, and to keep moving forward. As you gain momentum, the fear will begin to fade, and the excitement of building something of your own will take over.

Embrace the Risk

At the end of the day, life is full of risks. But the biggest risk of all is looking back and realising you never took the chance to create the life you truly wanted. Staying in your 9-to-5 might feel like the safe option, but if it’s not fulfilling, it’s a trap. Don’t let the fear of the unknown keep you from chasing your dreams. Embrace the risk, take the leap, and build something that you’ll never regret.

So, what’s it going to be? Will you play it safe and risk a lifetime of “what ifs,” or will you take control of your destiny and create something extraordinary? The choice is yours.





Jenna Hadden — Marketing Strategist & Author

About the Author

Jenna Hadden is a marketing strategist and author of My Infinite Game, blending insights from authentic marketing, leadership development, and human connection. She helps professionals grow with purpose and resilience in an increasingly digital world.

Explore more at JennaHadden.blog