If you’re not familiar with Jocko Willink, he’s worth following. He’s a very frightening former navy seal commander who’s written a number of books, has a very popular podcast, and famously posts a picture of his watch on Instagram at 0430 every morning as he starts his daily workout. His mantra is discipline equals freedom. The more disciplined you are at getting your shit done, the more freedom you’ll have at the end of day. Admiral William H McRaven gave a very popular speech saying something similar – “Want to change world? Start by making your bed”. Life coach Jordon Peterson says to clean up your life, start by cleaning your room. They’re all advocating for some derivative of adding structure to your life.

Exactly seven months ago we made the decision to begin divesting from work and starting the move towards retirement. And exactly seven months ago I wrote a post lamenting that I needed more structure in my life. And how has that gone? Well, I, uhm, errr, ahem… haven’t done anything different. I wake up every day with exactly zero plan for the day. Of course there’s always the random appointment you need to keep, or a trip that was set up, or a social get-together. But my plan for the week is never anything more than a vague thought in the back of my head. I know it’s going to get hot later in the week so I’ll mountain bike Monday and Tuesday. I should probably mow the lawn before the weekend. It looks like Wednesday is going to be a powder day, so I’ll go cross country skiing today. We’re out of salad dressing, so maybe I’ll go to the store on the way home. Or maybe tomorrow. That’s it. That’s the sum total of my structure and planning, week in and week out.

It’s pretty hard to complain about that. I truly have a blessed life. It feels like I’ve been pretty damn busy the last seven months. I certainly haven’t had any shortage of things to fill my days. I think it’s clear I won’t be one of those guys who retires and then has no idea what to do with himself every day. But what have I actually done? I’m not actually sure what I’ve been doing all this time. There’s been some focus around the new ginormous motorcycle, but the rest of my time has been a bit of a blur. I know I’ve kept myself occupied, but doing what?

I had grand visions of making gourmet meals most nights and being on top of all the shopping and various household errands. There’s a number of household repair and yard maintenance things that need to be done. Getting back in the swing of a regular workout routine was high on the list of things to do. Being more focused on hobbies was also something I wrote about seven months ago. None of that has happened.

With a complete lack of structure, I’ve drifted along with whatever random thought came into my head on any given day. And like a spoiled child, most of my thoughts have been about playing and not necessarily taking care of business first. While it seems idyllic, I think the edges are starting to fray a bit. My weight has gone out of control without any sense of routine. Free feeding is not a recipe for success. The less I take care of business (home repair, cooking, yard work, etc…) the harder it is to be motivated to do those things. It’s hard to think about long term plans, like travel for Mrs Troutdog and I or even the next trip on the ginormous motorcycle when I don’t even have a plan for tomorrow. Even my copious playtime is starting to simply repeat the same things over and over. What happened to rediscovering some of my other hobbies that have been back-shelved for a while?

This is an incredibly fortunate and first world problem to have. But nonetheless, one I suspect I need to sort out before too long. As Jack Torrance said in The Shining, “all play and no work makes Jack a dull boy”. Ok, maybe that wasn’t exactly what he wrote but you get the gist. I still don’t see myself restarting a bullet journal or getting up at 0430 each day. But adding some level of structure to my week is looking more and more important. Maybe it’s just committing tasks to the calendar at the beginning of each week? Wait, that’s sort of the bullet journal isn’t it? Sigh… I don’t know. It’s terribly hard to become disciplined if that hasn’t been your nature. Maybe I’ll invent a new planning/tracking/goal setting methodology for newly retired folks. Become a retirement life-coach. This blog has been searching for a focus ever since I started writing it, maybe that’s what it should be? Can I practice what I’d preach? Hmm. Check back in six months and see if my new best selling “Life goals for retirement” book is underway. Meanwhile, I’m going mountain biking today. I’ll look at the calendar later. I promise.