Here’s a philosophy that seasoned executives, engineers and generals embrace that you and I should apply to personal finance, but usually don’t: The understanding that the problem isn’t that your plan flopped. It’s that you didn’t anticipate the failure.

It stems from an understanding in business (especially in the start-up space), technology and the military that most plans don’t survive its first contact with reality.

Whether for money or non-money matters, your plan is simply an account of what actions you’ll take to achieve a specific goal. With an outline of what will get done, when, how, and by whom, if relevant.


When was the last time something didn’t go exactly as planned?

When was the last time something fell through the cracks?

When was the last time a project milestone was missed? Or, you didn’t fulfill a “small” commitment or promise?

Was it earlier today, yesterday, the day before that?

Embarrassment & Money, cont’d

Before I tell you why I’m asking these questions, a little context…

On Wednesday, 14 June, I did a Facebook Live with Family Circle Magazine and talked about the “6 Money Mistakes Women Make That Block Their Wealth.” You can click here to check out my conversation with the magazine’s Health Editor, Lynya Floyd. (You don’t need to have a Facebook account to watch the video.)

As you might suspect, we talked about the intersection of emotions and money. And when asked about the common emotions people have that are tied to money, not too surprisingly, I mentioned fear, over-confidence, guilt, shame, and, of course, embarrassment.

The responses to my anonymous survey are evidence that the reasons one might feel embarrassed about their money are aplenty. Losing money on a financial investment; not knowing what questions to ask or whom to turn to for guidance; not being able to practice self-control; not being able to tell family members “no” when they ask for money because you don’t want them to think you’re stingy; even not be willing to really talk about money with your beloved are just a few examples.

They reflect your reaction to something you did, or something you think you should be doing, but aren’t. And in some instances, they prompt the feeling of not being “perfect” – in your own eyes or in the eyes of others.

One of the reasons I’ve dedicated the last several posts to exploring the intersection of money and embarrassment is because the embarrassment some people carry around when their image of financial perfection isn’t met – even if you’re the only one that knows – is a powerful force that affects the choices you make (or don’t).

“Where there is perfection there is no story to tell.” ~ Ben Okri

Sure, some people feel embarrassed by their success. But a far greater number feel self-conscious about failed plans and not meeting expectations – whether set by themselves or others. It stings. Even more so, if it happens on a large scale for many to see.

A recent “oops” of my own has reminded me of the importance of anticipating failure. And here’s what I recently re-learned, which may prove useful to you, too: It’s not self-defeating to expect your first plan to fail; it’s actually quite wise! 

But how do you wisely anticipate failure?

Here are a few ideas:

Embrace experimentation

Reid Hoffman, the co-founder of LinkedIn and host of the podcast, “Master of Scale,” said this on a recent episode: “You don’t just make plans, you break them.” I think this is something engineers do well. As they seek solutions, they inherently have the mindset of experimentation. Do you?

Or, when it comes to your money are you a “this one and only” plan has to work type of gal/guy?

Six months into the year is an ideal time to take another look at your financial plans. If you consider all the places where things might break down and they did, what would be your counter-response?

Practice detachment

One of the reasons you and I hit a rough patch when our best laid plans go sideways is because we view the failure as an affront to our being. The thinking goes like this: The plan failed, therefore I am a failure. Going down that rabbit hole is dangerous. You spend more time self-judging than you do “righting” the ship and using the failure as feedback for tweaks to make moving forward.

Be willing to ask yourself some uncomfortable questions

Sometimes your plans fail because the facts you considered or the variables you weighed changed over time, or perhaps both happened at inconvenient times. Regardless, this is the perfect time to ask yourself if your plan was badly designed from the start; if you didn’t pay attention to the warning signs along the way that it was going to flop; or, if you simply did a poor job with execution and implementation.

Plan B will only be better if you do a little truth-telling – even if only to yourself – and adjust your tactics accordingly.

If it works for the military…

If you presume that most of your initial plans won’t survive the first contact with reality, it might behoove you to shift from thinking “if” my financial plans were to fail to “when my financial plans fail, this is what I am going to do.”

Whatever may be your life and financial goals, “when my plans fail, this is what I am going to do,” becomes the key to being prepared as best you can for the uncertainty of the future.

Whatever may be your life and financial goals, “when my plans fail, this is what I am going to do,” becomes the key to being prepared as best you can for the uncertainty of the future.

So, don’t let the cultural attraction to perfection and your unspoken expectation that everything will work out precisely as you’ve planned blind you to the value of anticipating failure.

Don’t let the idea that your initial plan is the only way to achieve your goal rob you of what you are working hard to build and sustain.

Because the emotional price will likely be higher than the financial price you’ll pay.


p.s. Here’s what happening this month:
(a) The last Comfort Circle™ dinner before we break for summer holiday is scheduled for Monday, June 26th at 6:30pm. The theme: designing your communications strategy. Click here to RSVP.
(b) A four-part virtual lunch-n-learn for people with debt. “Out of the Red, Back to Black” shows you how to fix the debt mistakes you’re unwittingly making so that you can get out of debt faster…and with greater ease. Click here for more information.

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