Mike and Al discusses common regrets retirees have such as retiring without a clear plan, underestimating inflation or healthcare costs, or remaining too tied to a job for identity rather than purpose. They highlight how mis-timing retirement (either too early or too late) and failing to update the investment plan for post-career life can lead to avoidable stress and missed opportunities. Key themes include the value of financial flexibility (having buffer assets or part-time income), and aligning your retirement lifestyle with what truly matters rather than clichés of endless travel. The takeaway: proactive planning and mindset shifts matter as much as portfolio size in avoiding “what if” regrets.