Your instinct screams stop. Everything in you wants to walk away. The path ahead looks impossible, and quitting feels like the only rational choice. But what if that feeling is wrong? What if the moment you most want to quit is exactly when you should double down?
Most business owners face this crossroads. The point where continuing feels harder than stopping. Where the dream that once propelled you forward now feels like a weight dragging you down. Learn from entrepreneurs who faced make or break moments in their business.
The moment where everything changes
Business growth partner Jess Rawstorne built her business for freedom. Instead, she built a trap. “For years, I believed more people, more hires, more hands would be the answer. If I could step back, they could handle the details. I could finally be the visionary, not the operator,” she shares. “But that’s not what happened. Instead, I was drowning.”
Her business was falling apart, revenue plummeting. Then life delivered another blow, her mother was dying. In that moment of grief and exhaustion, something shifted. “I was forced to let go,” she explains. “And here’s the thing about losing control: it shows you what actually holds.”
What should have been her business going under became the moment of clarity. She discovered the stripped-down version that actually worked with key people who could run things without her, systems that caught the chaos, and strategic leverage that let them operate leaner but stronger. The result? “We didn’t just survive. We scaled. Today, we’re doing 3X the profitability with a fraction of the stress (and the staff).” Sometimes falling apart is the path to building something better.
The unexpected pivot
AI innovator Holly Picano started as a traditional artist painting at Café Tu Tu Tango and later worked at ad agencies, until she lost her job. “Suddenly, I was paying rent with my Amex,” she recalls. Rather than giving up, she remembered her mother’s advice: “Focus on what you can control and give the rest to God.”
She went back to school as a single mom, earned her Master of Science in Digital Marketing, and then spent over 2,400 hours with OpenAI’s DALL-E 2 & 3. That investment led to a book deal and attracted billion-dollar companies for AI illustrations and automation. “Now, I’m running my own agency… My rock bottom was just a pivot point to something bigger!” Sometimes the lowest point becomes the launching pad for your greatest success.
The culture collapse
Exited SaaS entrepreneur David Sinkinson started his company and then “blew it on culture.” The result? “Everyone left. Thought we were maybe done.” Many founders would walk away at this point, but David made a critical choice. He restarted the company culture and actually listened to people. He stopped barreling forward with his own convictions and invited the smart people he had hired to have a say.
That decision created a remarkable transformation. After the reset, they “lost almost no employees after 8 years” and eventually sold the company “for a bunch of money.” Sometimes the moment of greatest failure becomes the opportunity for your greatest reset.
The platform collapse
What happens when your entire business model gets destroyed overnight? ESL teacher Anna Tyrie found out the hard way. After building a successful YouTube channel with over 300 million views, everything fell apart. “COPPA regulations saw Youtube make some swift and unannounced changes, with most kid’s content creators suffering a damaging blow to adsense income. Our income dropped by 98% and never recovered.”
Most would quit. Anna didn’t. She took what she had learned and redirected her focus to another venture. “This time, I built a website, started building a mailing list, and worked on building a following across multiple platforms.” Today, she has a successful ESL business online that she works on part-time. The lesson? “That day I learned that if your business relies on a third party platform then it is never safe.” Sometimes destruction becomes the catalyst for building something more sustainable.
The health challenge
Your body can betray you, but your mind doesn’t have to follow. Marketing coach Nicole Osborne hit rock bottom when perimenopause floored her. “Extreme mood swings, embarrassing brain freeze moments, and energy so low I barely felt like myself. The worst part? I didn’t even think to ask for help at first because I felt so low.”
Rather than give up, she tackled the problem head-on. “I booked a GP appointment. I read everything I could. I threw myself into new self-care routines. I reduced my hours.” The outcome transformed her life and career. “At 48, I like the new me even more! My business has grown. I can now call myself a jogger which I never thought was possible.” Physical challenges can become opportunities to rebuild better versions of ourselves and our businesses.
The last ditch attempt
AI startup founder Renaud Vandewalle started his business and faced two years without revenue. “As our pipeline was not looking good in December last year, I only had a few months runway and all my bank accounts were empty.” Instead of giving up, he went all in, investing in help and shortening his runway even further.
The gamble paid off. “In February, out of nowhere we got a great deal extending our runway for at least 9 months and we are starting to get a healthy pipeline.” As Vandewalle proved with his all-in approach over Christmas, whatever you sow, you shall reap. Sometimes the darkest hour really does come right before the dawn.
The complete rebuild
How do you start over when you’ve lost everything? Healthcare leader Rachael Lemon faced workplace bullying that could have ended her career. She was told, “You can take a demotion or leave; I’m restructuring. Your choice, I don’t care.” She didn’t take a demotion, didn’t leave, and navigated a tribunal which was favorable despite the year it took and the hostility she endured.
The process revealed something even more important, she was desperately unsafe at home. “I lost my job, my home and my partner, the respect and friendship of many peers who didn’t understand domestic abuse and everything I’d worked for! I started from zero in my 40s. All I had was my Polo, my laptop, cabin case and dog.”
That moment of complete loss became her moment of freedom. “I realised that I accepted less than I was worth from far too many people, existing in a state of fear. But in that moment, with absolutely nothing left, I was free for the first time.” Sometimes losing everything is the only way to discover what you truly want.
The choice to continue
Wanting to quit is normal. Feeling like you can’t go on is part of every success story. But these stories prove that pushing through can lead to something better than you imagined.
The next time quitting feels right, remember these stories. Remember that your breakthrough might be waiting on the other side of this challenge. The path forward might look nothing like what you expected, but it could 10x what you’re leaving behind.
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