Why Solopreneurs Struggle to Start Over—and How to Break Free
I am a huge fan of Katy Milkman. She is the James G. Dinan Professor at The Wharton School of the University of Pennsylvania, host of Charles Schwab’s popular behavioral economics podcast Choiceology, and the former president of the International Society for Judgment and Decision Making. Here is a recent podcast that hit me exactly where I am today...do I need to start over?? I thought I would share her insights along with my learnings - and hopefully it will help those on their solo journey.
When you’re building a business solo, every decision feels weighty. You’ve invested your time, energy, and often your savings into moving forward. So when the path you’ve chosen isn’t working, the idea of starting over can feel unbearable - so unbearable.
This tendency to resist retracing our steps—even when it’s the wiser move—has a name: “doubling back aversion.” It’s a cognitive bias studied by UC Berkeley professor Clayton Critcher and his collaborator Christine Cho. Their research shows that people avoid undoing progress because it makes them feel like their past efforts were wasted. Ironically, this mindset leads us to waste even more time, money, and energy by pressing on in the wrong direction【Choiceology Podcast, Charles Schwab】.
Lessons from the Panama Canal
History illustrates the danger of doubling back aversion. Ferdinand de Lesseps, who famously led the successful construction of the Suez Canal, insisted on a sea-level design for the Panama Canal—even though experts warned it wouldn’t work. Refusing to revisit his plan, he pressed on until the project collapsed. The effort cost 22,000 lives and bankrupted investors. Eventually, the U.S. succeeded by adopting the very lock system he had rejected【Choiceology Podcast, Charles Schwab】.
For solopreneurs, the parallel is clear: stubbornly clinging to a strategy that isn’t working can be more damaging than having the courage to start again.
How Doubling Back Aversion Shows Up in Entrepreneurship
Refining a product that doesn’t solve a customer’s real problem.
Spending months on a marketing strategy that delivers little traction.
Staying in a niche with no demand out of fear of “wasting” prior work.
Breaking Free: How to Overcome the Bias
Redefine Waste – Past effort isn’t wasted if it gave you clarity about what doesn’t work.
Set Checkpoints – Schedule regular reviews to ask: Is this still serving me and my customers?
Kill Your Darlings – Be willing to let go of offers, strategies, or habits that no longer serve your growth.
Adopt a Future Orientation – Focus less on sunk costs and more on what will move your business forward.
Normalize Pivots – Build a network of peers who share not just wins, but struggles and resets too.
The Courage to Begin Again
As solopreneurs, the boldest decision we sometimes make is not to charge ahead—but to pause, reassess, and start fresh. Recognizing doubling back aversion can help us shift from clinging to sunk costs toward leading with clarity and purpose.
Because in entrepreneurship, as in life, the best way forward often starts with the courage to begin again.
If you need a voice who can help you with a pivot, a shift, or rethink a direction, reach out. I am here for the conversation.
About Charissa
Charissa Gant, Change Strategist with over 30 years of experience driving change for Fortune 500 companies. Most recently, a Principal Director at one of the largest consulting firms. Leading change with empathy. Unlocking leadership potential. Owner and Founder of BoldLEAP Collective, a community for courageous solopreneurs. Charissa@boldleapcollective.com