Fear Asks “What If,” Courage Asks “Why Not”

You probably spend a good bit of your life asking “what if?” questions. What if I fail? What if this relationship doesn’t work out? What if this professional opportunity is too risky, too soon, too much? When a new opportunity arises, you might tell yourself a story filled with fear and negative outcomes. Your go-to response is to avoid risk and only consider the reasons to say no. This approach to change can feel responsible, maybe even wise. Change is rarely met with “why not make a success of this?” 

More often, though, you’re stopping yourself from stepping into life-changing opportunities. “What if” thinking can keep you stuck in a cycle of problems while “why not” thinking can invite new possibilities. When you stop asking “what if everything goes wrong?” and start wondering what could go right, you can start to move through life with a kind of courage that makes space for joy, growth, and trust in yourself. The linguistic shift is subtle but carries enormous power.

Redirecting your thoughts

Redirecting your thoughts from “what if” to “why not” is the opposite of catastrophizing, inviting possibility, curiosity, and even a little magic back into your life. When you approach decisions asking “why not,” you make space for good things to happen. You give yourself permission to chase what brings you happiness, even if it feels a little risky. Because sometimes the most meaningful choices don’t follow logic or linear progression. They follow joy.

What makes you feel alive?

Too often, you can get caught up in the “A leads to B, which leads to C” version of life. Except life isn’t an algebra equation. You might be stuck following the motions because someone taught you that’s what success looks like. But fulfillment doesn’t have a formula. 

“Why not” thinking encourages you to break the pattern and follow the sparks of excitement that remind you you’re alive. To stop waiting for the “right time” or the perfect conditions, and start trusting that the joy you feel when you imagine something new is reason enough to say yes.

The older I get, the more I find myself focusing on what makes me happiest—what gives me butterflies, what makes me smile without effort, or fills me with energy with one thought. To me, that is what’s worth chasing. 

The wisdom in risk and reward

I’ve learned that change comes with age and experience. As you grow, your understanding of risk and reward evolves. You recognize that not every risk is dangerous, and not every reward is measured in achievement or accolade.

Experiences teach you to trust your instincts and distinguish between fear and intuition. It gives you the confidence to take chances that honor what matters most to you. Most importantly, experience reminds you that the worst-case scenario is rarely as bad as you imagine. You’ve done this before. You’ve made mistakes, learned from them, and still managed to keep going. Trust that you can do it again.

When ‘why not’ clicks

When I reflect on what it means to have courage in the face of risk, my mind turns to the incredible entrepreneurs and business professionals I teach. One of my former students, AnnMarie D'Erasmo, owns Posh Pretzels. They make the most incredible pretzel treats, each made with care, creativity, and love. 

AnnMarie started small and was hesitant to risk expanding beyond her home business. It was her kids who encouraged her to take on less of a “what if” and more of a “why not” mindset. She worried that a store might be too expensive, that she would have no customers, and that she would fail. But she was able to push herself to try and see what would happen if she trusted herself and her vision.

With her family's support, she started dreaming bigger and imagining what could happen if she opened a retail location. When she finally took the first step, she discovered not just incredible growth but also a sense of alignment. Her work became something her whole family could take pride in, and she found joy in building something bigger than fear. That’s how “why not” can reconnect you to purpose and possibility. 

This kind of openness doesn’t happen without effort. You have to make space, both mentally and emotionally, for new experiences to come into your life. That means saying no to situations that drain you, to patterns that keep you stuck, and to the endless worry that masquerades as preparation.

Making space for what’s next

When you clear that space, opportunities start to find their way in. Rather than hoping you’re lucky, accept that you’re ready and be open to receiving what you’ve been working so hard for. After all, what is the effort, the long hours, and the hard work for if not happiness and satisfaction? Hard work without joy isn’t resilience. It's exhausting, and you deserve more.

Choosing “why not” isn’t about saying yes to everything. It means giving yourself permission to chase the dreams that push you, the adventures that light you up, and the possibilities that remind you your story is still unfolding.

Letting "what if" dictate your choices might be the greatest risk of all, because you’re guaranteed to miss out. You’ll always regret the chances you didn’t take more than those you did. So the next time you catch yourself spiraling through the “what ifs,” pause. Instead, ask, “Why not me? Why not now? Why not this?” You might find that the answer leads you somewhere wonderful.