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Winter is here with a vengeance, and the ski slopes are alive with CEOs who have nothing better to do than hone their powder skills — and think about what might have been. Many will no doubt be replaying the miscalculations and misjudgments that led to their current difficulties. Yet the curious thing is that these very errors, if made at an earlier stage of their lives and careers, might have saved them a lot of time and trouble.

Take the embattled head of a large company whose appetite for publicity proved to be so insatiable that her persona became essential to the marketing of the product. Her steely composure, so well known that her very name is still synonymous with perfection, never failed her — so much so that she apparently believed she could out-bluff the Securities and Exchange Commission. Yes, Martha Stewart had it all; and now she’s clinging by a legal-defense thread, a talented and effective CEO potentially undone by a single misstep.

You can’t help but wonder what she was thinking when she allegedly called her stockbroker to request what increasingly appears, at best, to be a questionable trade. Yet when you’re as competent and on such a roll as she was — successful TV show, successful magazine, successful IPO — it’s sometimes too easy to imagine you have been given a pass on the normal rules of business practice as the SEC is now claiming. In my opinion, the only way to keep your head in such a self-induced whirlwind is to know otherwise, which is the kind of knowledge that only comes from experience — i.e., failure.

The greatest teacher of them all

It was La Rochefoucauld who said that “‘You should commit errors in youth so that you have something to regret in old age.” Being much more of a playboy than a businessman, the French wit missed the most valuable part of making a misstep: the opportunity to learn how to keep the same thing from happening again. And while to vow to make any error whatsoever may seem a strange resolution, here is my list of four kinds of errors everyone should make before becoming a CEO:

Error No. 1

Errors of experience. These are the baby steps we all must take — the flubbed pitch, the blown assignment, the botched delegation of authority, the overreaching decision. From being too timid to ask a vital question in a big meeting, to being too bold within the same meeting with an idea that’s ill-conceived, the list goes on and on. And it never ends, if you’re at all committed to forward progress, because nobody is infallible.

Error No. 2

Errors of excess. Martha Stewart’s apparent problem, like a lot of today’s young executives, was, in my opinion, that she learned to fly before she learned to walk — easy enough to do in a booming economy. Her strongest point — an almost visceral sense of what her audience craved in their lives, the home as haven — pushed her from one successful venture to the next without pause. But it also led her to leap into the breach one too many times, and allegedly wing it in a field, securities law, where angels fear to tread.

If Stewart’s famous gut instinct had failed just once, early on, might she have hesitated? Possibly. As William Blake says, “The road of excess leads to the palace of wisdom.” I would add that this works best when you’re young.

Error No. 3

Errors of the heart. A true Achilles’ heel of CEOs is so neglecting their emotional life that it belatedly sneaks up and deals a dizzying blow. This can come in the form of a sudden and overwhelming desire to spend time with their children — who may be on the verge of flying the nest and showing signs of independence. It may be spurred by a spouse who is fed up with coming in second to a job and decides to leave; and, of course, it can strike in the form of a whirlwind affair that sweeps everything before it.

In literature and in life, we can find numerous examples of this kind of behavior, which makes you think that someone as smart as a CEO would be well innoculated from it. But knowing something mentally is different from experiencing it — and most CEOs are too busy to spend time going to plays and movies, anyway, so they miss the artistic reminders.

The moral here is to have a life while you’re building your career. And if you find you just can’t be there for your spouse and family as much as they’d like, there are classic plays that might be worth reading: Shakespeare’s “Tempest,” for starters. (Prospero is an emotionally blind CEO if ever there was one.)

Error No. 4

Errors of sensibility. Many executives on the way up edit their lives down to the essentials in order to have fewer distractions. There’s no question that this works, but life ought to be tempered with some extraneous interests or hobbies. This is why the more successful and long-tenured CEOs tend to have a side passion, whether it be orchids or wooden boats or the drawings of the Impressionists or the ballet. These sorts of interests can seem a trifle incongruous in the context of a CEO’s aggressive persona, yet that’s undoubtedly why they work so well relieving stress. They open the mind to another realm of endeavor, and allow people whose values are vastly different access to their world.

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