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May 23, 2025 40 mins

20 years ago, American Idol winner, Kelly Clarkson, blanketed the airwaves with Since U Been Gone. The song explores the aftermath of a now-ended relationship. While break-up songs often express longing, regret, and sadness, Since U Been Gone is a realization of how much better things are now. It also expresses the feeling of finally recognizing red flags that have been in plain sight for a while.

These feelings are not exclusive to romantic relationships. People get emotionally connected to software they use at work all the time. And sometimes, they start rethinking their commitment, especially when the relationship feels one-sided. Reagan Helms has led Support at Planning Center for 15 years and during his last appearance on the show during Season 2, he compared his relationship with his support platform to marriage. But recently, that relationship soured and he’s moving on.

• Warning Signs in SaaS• The Migration Dilemma• Vetting New Solutions• AI That Actually Works• Preparing for ChangeConnect with Reagan on LinkedIn – https://www.linkedin.com/in/reagan-helms/

Music courtesy of Big Red Horse – https://bigredhorseband.com/

Brought to you by Happitu – https://happitu.com/

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