One of the things I like about my profession is that there are so many analogies to help explain it. Of the many I've heard over the years, one of the recurring themes is sailing. You're on your boat sailing toward your future, the captain of your own destiny. Hopefully you have a plan, a compass, a good navigator, and so on. I just read a pretty good one and you'll find it below.
Analogies should come from what you know, and I've never been more than an armchair sailor, so most of mine come from ultrarunning. Some years ago, I caught the running bug and eventually found ultramarathons. Ultras are, technically, any distance beyond a marathon but typically start at 50-kilometers (31 miles). There can be ultras on roads or tracks but they're usually on trails. There are 50-milers, 100k's, 100-milers, and even longer races.
Strange as it may sound, preparing for and running an ultramarathon is just like planning for and living in retirement.
Running an ultra is all about planning and preparation, putting in the work during training, setting realistic expectations, executing on your plan, and then being able to call audibles as things change and the fates seem to conspire against you.
Preparedness takes on new meaning when you are miles from aid on a hot day and realize you're out of water. It's the simple things that will get you every time. Learning how to deal with the unexpected is critical and winging it isn't an option, nor is inflexibility.
After all the miles run in training you have little idea what the conditions will be like come race day. Yes, there's the weather report but you can still get pummeled by unexpected rain and wind. Or heat. Or cold. Or all of these on the same day. Maybe you're running along fine and then, wham, you're on the ground, the victim of a thumb-sized root you should have seen up ahead. Maybe you realize too late you started off too fast and now have many miles to go with an energy deficit. Or, perhaps you realize that you're simply ill-prepared for the task at hand. There are no shortcuts and ultras can be cruel judges.
Fundamentally, the lessons of strategy, diligence, and patience in prepping for and running an ultra are directly applicable to financial planning.
There can and will be lots of uncertainty in your plans for retirement. Your personal and professional life will change, and so will your goals and objectives. Markets will be volatile and scary. A host of issues, many of which you cannot control, will try to lead you astray. In an ultra, the saying is to "run your own race", meaning you need to plan based on your personal goals and not get caught up in the goals of others. The same goes for planning for and living in retirement.
So, having a good and flexible plan is critically important. By being flexible as things change and working diligently on controlling what can be controlled, you'll have the best shot at success, whether your goal is finishing a race or a enjoying a happy retirement.
For a nautical version of this concept, check out the following essay from Jim Parker, VP at Dimensional Funds...