Throughout my career in information technology, I’ve witnessed the rise of Agile software development practices, emphasizing flexibility and iterative progress. These replace older approaches where a complex, multi-year project was planned out in detail…but those efforts were rarely successful…requirements changed, people changed and there were many things we learned along the way.

I realized that my notion of ‘phased retirement’ might be more appropriately called ‘agile retirement.’

Rather than having the years ahead of us all planned out, it’s more likely that we’ll approach retirement with shorter ‘sprints’ to borrow a term from agile software development. 

Instead of a rigid 20-year roadmap, consider an “Agile Retirement” approach. This involves:

1. Iterative Planning: Start with a short-term plan, focusing on the next few months. Gradually refine it as you gain experience and adapt to your changing needs and interests.
2. Embrace Change: Life is unpredictable. Be open to adjusting your plans based on unforeseen circumstances, whether it’s a health issue, a new opportunity, or a change in your financial situation.
3. Regular Check-ins: Schedule regular “sprints” for reflection. These could be weekly, monthly, or quarterly. Journaling, meeting with a friend, or consulting with a financial advisor can provide valuable insights.
4. Prioritize What Matters: Focus on activities that bring you joy and fulfillment, whether it’s travel, volunteering, pursuing hobbies, or spending time with loved ones.

Conclusion:

You should have a vision for your retirement, but you don’t have to have a detailed plan for the next 20-plus years.  Have a plan for the weeks and months ahead of what you want to do and try…and maybe even some level of detail for a year or two in front of you.  Then reevaluate periodically and make changes based on the learnings along your journey.