In 2018 I hopped on a bicycle and embarked upon a solo, cross-country adventure to raise money for charity. Whilst planning for the trip, I realized…there’s a relatively decent chance I could die. My second realization was: Dude, you’re 52  years-old, WTF haven’t you thought about this more?

My “Oh Crap” Moment

The reason I hadn’t thought about it more is the same reason as everyone else: I didn’t have to. And thinking about “it” sucks. It’s an uncomfortable thought, and of all the cans we kick down the road to deal with another day, that one can often stays kicked until we kick the bucket.

But, with my departure date coming fast, I realized I was kicking that can into my daughter’s life. That’s what happens when we fail to plan, our surviving loved ones have to figure it out and clean up a big mess. I knew I had to put my big boy pants on and make some adult decisions, so that in the event of my death, I wouldn’t leave my daughter (and grandson) holding the bag.

Why Aren’t We Better at This?

I didn’t know it at the time, but those first uncomfortable thoughts were the seeds that would later become the idea for Let’s Talk About Life Day. As I wrestled with the reality of preparing for my trip and the concept of my potential death, I started to wonder why it was so difficult. I mean, with so many people dying (like, everyone) why the hell aren’t we better prepared? I realized, I was absolutely and completely unprepared (with the exception of life insurance).

Crank’n on a nice stretch of trail, somewhere in the middle of Wisconsin.

Benefits Plan to the Rescue

In addition to life insurance, my employer offered a Will preparation service called Willing. I knew it was available, but I guess I figured if I didn’t use it, death would just kind of forget about me and move on to the next guy. With my bike trip as motivation, I ventured over to willing.com to take a peek. What I found was an extremely easy and approachable process. My guess is the folks that created that site know that we’d rather be doing almost anything else, so they’ve made it, well…dead simple (sorry).

It’s a Huge Load Off

After going through the steps, I printed it off and took it into my bank to have it notarized. The interesting thing was, afterwards I felt a great sense of relief. I didn’t even know that I had been carrying this weight on my shoulders until it was removed. That said, it’s worth noting that even though I summoned the belly fire to complete my Will, I still took a comforatable “off ramp” by simply including my Will in an envelope marked “important papers,” which I then gave to my daughter with no discussion.

In a future post, I’ll take a deeper dive into this “off ramp” strategy. It’s remarkable that even folks who have a very close call, and nearly die (like my mom), continue to evade making a plan to end well.

Willing.com offers other estate planning services that I’m looking into and will write about in a future post (living will, durable power of attorney, living trust, transfer on death deed). Have you used any of their services or those of other providers? If so, please share your experiences in the comments section below. Or, were you planning some kind of hare-brained adventure like me when the light bulb turned on for you? If so, do share. :o)