Recently, I met with someone who wanted to help me prepare for retirement. He told me I should be defensive with my money – health insurance, life insurance, disability insurance – and to be forward thinking or “offensive” with investments, money markets, roths, etc. If anything, I would want to invest in roth ira and calculate it with So that I will know how much I funded myself, it is a really good thing to do before retiring so if anyone is retiring. Consider a roth ira account.

He was a bit surprised when I told him that I didn’t want to retire. Instead, I’d like to take a chapter out of Stefan Sagmeister’s book and spread out my retirement throughout my life.

We began discussing how I might take a year-long break every eight years – or every other Leap Year. I’ve never shared that idea out loud, but the more we talked about it, the more alluring it became.

Though I think every year can be a space for learning, reflection and taking new risks, there is something special about the natural rhythm in our earth’s cycle – an extra day, a globally recognized title, a four-year rhythm – it creates a sort of built-in checkpoint. So what if every other Leap Year (2020, 2028, 2036), I personally invested in my life and family through travel, reflection, study, or by working on an audacious idea. It would build upon what our community did together in 2012 in a methodical manner and continue sparking meaningful conversations and acts. I’ve always been curious about how the Olympics take place every four years to celebrate feats of athleticism, endurance, and physical and mental prowess. Could Leap Year invite and celebrate bold acts of learning, growth, change and impact – a sort of Social Good Olympics? 

Of course, that means I need to prepare for it. It will be no small feat to save enough financial resources to make the idea a reality, so how do I prepare for those years now?

And, more importantly, I need to continue finding others who care about creating space for learning, growth and change and offer tools to design those spaces. That’s why the team & students at Experience Institute are working to create this set of tools.

In any case, I think the idea of retiring in our 60s in order to do very little work is shifting – in the same way that learning doesn’t just happen in our early twenties. I want to be someone who continues growing and contributing to society throughout my entire life, not just the first parts to it. Getting older doesn’t mean getting less useful; quite the contrary. Our best years are ahead of us and we ought to make sure we have energy and resources to help others until the day we pass.

So, pace yourself, enjoy the days you have now and prepare for those in-between (leap) years accordingly.

I’m going to continue working on this idea. I’ll keep you posted on how it unfolds…