It's always a little risky for an old guy like me to make a reference to something from my youth -- it typically draws blank stares, smirks, and the occasional rolling of eyeballs -- but I'm hopeful that when I say most entrepreneurs are worse off than the shoemaker's kids, the allusion isn't totally lost on younger readers. Just to be sure, the tale has it that the poor old shoemaker was always so busy tending to the shoes of others that he neglected the footwear of his own kids, who walked around with holes in their soles. Today's kids, often equally ignored, are more likely to have holes in their souls, but that's a topic for another day.

Entrepreneurs often do an amazing job of taking care of their businesses and attending to every detail, but in the rush, and because they're convinced that they're immortal, they forget to pay attention to some of the most critical and essential concerns in their personal lives. You'd be absolutely amazed, for example, at how many men and women running successful startups in their late 20s and early 30s (with or without kids) have no life insurance. It's not that they don't know that it's stupid and irresponsible not to provide for their families or that they can't afford it. They never get around to doing it until, in too many cases, it's too late.

Adequate life insurance is actually only a small part of the bigger problem. Entrepreneurs of all ages suffer from the same blind spots and short-sightedness. They're so totally swept up in today's rush and crush that they rarely give five minutes thought to tomorrow and, most important, to what would happen to their spouses and kids if they weren't there. If you're reading this and you are foolish enough to think for a minute that you've got this problem covered, think again. Passwords, as an example, are just the very tip of the iceberg.

The list of things that need to be immediately addressed and attended to in the event of an unexpected death or incapacitation is enormous and, by the way, not limited to concerns regarding your spouse and kids. Having an attorney, an accountant, an executor/executrix, and a will turns out to be just table stakes in the preparation race, because the more pressing and critical concerns relate to the million day-to-day things that we all take for granted until the dam breaks.

Add to the list: access for dozens of key accounts, financial details, medical files and information, investments and partnerships, mortgages and deeds, insurance (cars, home, umbrellas, jewelry, etc.), education expenses for the kids, utilities and subscriptions, credit cards (including autopay accounts), taxes and tax returns (state, federal, real estate, etc.), vehicles (owned and leased), health care records, social security, Medicare, cemetery plots and funeral arrangements, etc.   

And, for many of us in the "sandwich" generations--squeezed financially between kids and parents -- even if you have things reasonably well in hand for yourself (highly doubtful), the lack of preparation and documentation regarding your parents' state of affairs is an even more daunting prospect. Yet this is a project that may well plop itself in your lap at any time in the near future. That's the problem with the future -- it has a nasty habit of arriving before we're ready for it. Getting ready, according to no less an authority than Henry Ford, is the secret to success. He may have been a bigot, but he got that right.

I'm happy to report that help is at hand if you're prepared to make the modest investment of time required to get the process started. There are various flavors of solutions -- many focused on funeral preparation like Cake or Lantern -- and some like EverPlans, which are now tied to larger life insurance companies. The one that I find most comprehensive was started -- as you might imagine -- based on personal experience and the recognition that the founder, just like the rest of us, was grossly unprepared for any kind of catastrophic life cycle event.

The nice thing is that it's a simple iPhone app called Paperwork that provides as close to a fully comprehensive solution as I have seen anywhere, but lets you get started by doing as much or as little as you like and then building from there. I can tell you though that it's seductive and a little sneaky in a good way -- especially for Type A entrepreneurs -- because once you do get rolling and start adding material and important parts of your life to the file, the temptation to put everything into the system as soon as possible is almost irresistible.

Entrepreneurs aren't good at doing much of anything halfway, especially when they're doing for themselves and for their families as well. In for a penny, in for a pound. It feels a little like deciding that -- because it's midnight and you can't keep your eyes open -- you should leave an uncompleted jigsaw puzzle with just a couple of dozen pieces to go sitting there on the table taunting you. We both know you're way too compulsive to do anything like that. And, of course, in this case, it's for an especially good cause.

So, take a little time (now's a great opportunity) and do something nice and important for your spouse, parents, and family. Check out Paperwork and organize your life now while you can. You can thank me later.