Hello everyone,
I went through a breakup this week.
I left Calendly. After two years.
Not because it was bad, it worked fine. But my colleague mentioned TidyCal, I looked at the price ($29, once, forever), did three seconds of math against my $10/month Calendly bill, and that was it. Exported my schedule, imported it into the new tool, and the whole switch took about five minutes.
Two years of loyalty, gone in five minutes. And it got me thinking about how fragile "loyalty" really is when someone makes it easy enough to leave.
Let's dive in.
Psychology behind loyalty
Samuelson and Zeckhauser ran a simple experiment. They told people to imagine they'd inherited money and had to decide how to invest it (moderate-risk stocks, high-risk stocks, treasury bills, or municipal bonds). Same options for everyone.
But one group saw a neutral list. The other saw the same list with one option labeled "your current investment."
The labeled option went from being picked by 32% of people to 47%. Nothing changed except the word "current."
Most of your competitor's users are running on the same autopilot. They're not staying because the product is great. They're staying because all their stuff is in there and leaving feels like work.
Behavioral researchers call this status quo bias. But you don't need the term. You just need to know: the biggest barrier between your competitor's users and your product is the perceived hassle of leaving. Not features. Not brand love. Hassle.
And hassle is something you can engineer away.
How it shows in user behavior
Three questions run through someone's head before they leave (or don’t) a competitor for you.
1. "Do I have to rebuild everything from scratch?"
If switching feels like starting over, people won't start, even when your product is obviously better.
Your competitor's users have settings. Schedules. Integrations. Workflows they spent weeks dialing in. Their brain codes all of that as investment.
Losses hurt roughly twice as much as gains feel good. So "our product is better" is a gain. "You'll lose your setup" is a loss. The loss wins every time.
2."Can I actually afford to say no to this deal?"
When your pricing is structurally different from the competitor's, you change the whole equation.
There's a gap between "we're 20% cheaper" and "you'll never pay again."
A discount makes people think. A one-time lifetime price makes people act. You're not just saving them money — you're wiping out an entire category of cost.
3."What if it doesn't work and I can't go back?"
People don't fear switching. They fear it being a one-way door.
Inman and Zeelenberg studied this directly in a 2002 Journal of Consumer Research paper. Consumers anticipate more regret from switching to something new than from sticking with a repeat purchase. Action feels riskier than inaction. But here's the key finding: when people had a clear justification for the switch, that regret dropped significantly. A good reason to leave made leaving feel safe.
That's what free trials, money-back guarantees, and refund windows actually do. They give someone permission to act by removing the "what if I'm stuck" fear.
How to Turn It Around
Back to my Calendly story.
I'd been paying $10/month for two years. The tool was fine. I had my availability set up, my meeting types configured, Zoom connected, booking link everywhere. Classic autopilot.
Then TidyCal showed up, and here’s how they won me.
1. First, they built a direct Calendly import.
I exported my schedule, uploaded it, and my availability, meeting types, and settings came with me. I didn't rebuild anything. I didn't re-enter my Monday-through-Friday blocks one at a time. Five minutes, done.
2. Second, the pricing. $29 once versus $120/year.
Less than three months of what I was already spending, and then nothing, forever. TidyCal doesn’t cover all of Calendly's features. But for my use case (booking calls with clients and prospects) that's 99% of what I actually need.
3. 60-day refund window
Try it for two months, and if you hate it, get your $29 back. Compare that to being locked into a Calendly annual plan mid-cycle. The risk is almost comically low.
TidyCal didn't try to out-feature Calendly. They attacked the switching costs instead. Three walls down, and a two-year customer walked out the door in five minutes.
If you forget everything, remember this:
Don't just build a better product than your competitor. Build a better exit ramp from theirs.
🎉 Woow, you finished the issue, that’s awesome!
Hi, I’m Anastasia Kudrow, and I write Ghosted.
I am also a product growth consultant. I help SaaS teams apply psychology and PLG to build growth they can actually control. I run my own project, Growing Pains, and also work with one of the leading PLG consulting agencies, ProductLed, led by Wes Bush.
Feel free to follow me on LinkedIn: https://www.linkedin.com/in/anastasia-kudrow/
Or check out my website, maybe we can work together: https://www.growingpains.consulting/
See you next week!
