When Everything Goes Sideways — Then Points the Way Forward

Have you ever seen this happen:

A well-thought-out plan, a carefully researched idea, a project somebody believed in—falling apart.
I bet you have. It can be absolutely devastating.

For new entrepreneurs, these kinds of setbacks can feel like confirmation of every self-doubt we’ve ever had. “Maybe I’m not cut out for this.” “Maybe this was a mistake.”

But the truth?

It may feel like the end of the world for some, but setbacks do not have to be the endpoints. Setbacks are points for inflection (shifting gears). What you do next is what defines your growth.

You could give up, or you could pivot.

I recently heard a story about a school teacher who had tried to launch a pop-up café that combined her love of community, creativity, and coffee. Her idea was to use local community centres while spotlighting student artwork and creating a vibrant space for connection. Students and their families would be running the events on the weekends.

At first, plans were in place and things looked promising. They held some opening events which people showed up to. It seemed the community liked the concept at first. Then, things happened. I don’t know the details except that there were issues with the community centres and unreliable volunteers. Ongoing marketing couldn’t be sustained. The café owner was discouraged and undoubtedly exhausted.

But instead of quitting, she paused and did something powerful: She stepped back and looked at the trail of clues hiding in the wreckage and figured out the root cause of the issues.

There were roadblocks she hadn’t thought of—perhaps relating to things like liability, licensing and volunteer roles. But the point is this:

After pausing, she found the next right step.

Deconstructing Setbacks to Find the Wisdom

Every challenge in entrepreneurship contains a trail of clues. If you're willing to pause and listen—without any ego or judging yourself—you’ll figure out how to move forward without throwing in the towel.

Let’s break it down:

1. Setbacks Are Not Failures—They’re Feedback

Setbacks aren’t signs that you’re not good enough. They often point you towards those things that aren’t aligned—your schedule, your offer, your audience, your assumptions, etc.

What if your latest failure isn’t a dead end—but just an early draft?

Learning from failure is one of the most strategic skills you can develop.

2. Assumptions Are the Silent Saboteurs

Sometimes we don’t even know we’re operating on faulty beliefs. “If I just work harder, it’ll come together.” “This is what others are doing, so it must be right.” Those unspoken assumptions can steer us straight into burnout.

The café owner I described above hadn’t done enough fact-finding and had been making plans based on her assumptions.

In the end, she pivoted to an online subscription box which proved to be a success. Small-batch coffee and student artwork prints were now being delivered to customers’ doors—same mission, but different delivery. The business grew, and all because she stayed the course to determine a better business model for her goals.

3. Let Go to Grow

Clinging to a failing idea just because you’ve invested time and energy into it is like wearing shoes blistering your feet, just because they were expensive. Blisters slow you down, they hurt, and the blood could ruin your shoes. You get the point.

Moving forward sometimes means moving differently.

Growth doesn’t require things to be perfect. It requires humility and responsiveness. And that’s a muscle entrepreneurs can build.

If you’re working on strengthening your mindset muscles, our Free Guide: 5 Mindset Shifts for New Entrepreneurs offers simple, practical insights to help you bounce back with clarity and confidence.

Here’s a reframe: Success isn't about never falling down. It's about becoming someone who knows how to stand up differently each time they fall.

Setbacks Shape Your Strategy—If You Allow Them

Here at Ready Set Grow, we believe your entrepreneurial journey is as much about who you're becoming as what you’re building. Challenges aren’t there to crush you. They’re there to help you refine your plans to become smarter, leaner, and more resilient.

Unearthing the assumptions you unknowingly carry into your business is eye-opening and freeing. Because once you see your patterns, you can change them. Once you extract the real lesson from a loss, you’re already winning.

You’re Not Alone on This Path

We all have a story or two about something that didn’t go the way we hoped. But what if that’s not the end of the story?

What if it’s just the first draft of something better?

Ready to Build Your Bounce-Back Strategy?

If you’ve hit a wall—or want to avoid one before it hits—you don’t have to figure it all out on your own.

🔍 Pre-register for Module 1: Entrepreneurial Fitness of our Ready Set Grow online training program – and take the first step toward building your roadmap to growth.

At Ready Set Grow, we help you turn insight into action and build the confidence, clarity, and mindset resilience to handle setbacks like a pro.