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Measuring Success – Don’t Fall into the Gap!

10 November 2021

I’ve been reading The Gap and the Gain by the always-worth-reading Dan Sullivan, and, as his books always do what they do – got me thinking.

There’s an entrepreneur – super-smart, skilled and achieving, and so successful – who is never happy with the success they’ve achieved.

I don’t have to name names – because we all know him or her. Maybe more than one him or her. Maybe that’s even us – I know it used to be me.

This person, like too many high-achieving entrepreneurs, makes a fundamental error when measuring success. S/he has set an impossible ideal as the goal, and always measures success according to the distance between what s/he has actually achieved and that ideal.

Which is a recipe for unhappiness, dysfunction, and dissatisfaction. Because we are never going to achieve an ideal. Ideals, by their nature of perfection, are not humanly attainable.

Robert Browning famously wrote, “Ah, but a man’s reach should exceed his grasp, or what’s a heaven for?” And that’s a lovely sentiment, but when it comes to business, we need a more realistic template.

This is not to say “don’t set goals.” We need goals – but not goals like “I want to be super-rich,” because that’s likely subject to upward creep – we may have had an ultimate goal of, say, approximately $20 million in net worth, but as we approach that goal, do we say to ourselves, “Well, $20 million isn’t what it used to be,” and revise it to $30 million? And keep revising, always unhappy with where we actually are and how much we have?

Our goals should be specific, realistic, and quantifiable. Goals that we cannot and do not deny we’ve reached, when we do so.

We also need to pat ourselves on the back and appreciate our progress whenever we do reach a specific, realistic, quantifiable goal we’ve set. The measure of our success should not be how far short of our ideal we are, but how far we’ve come from where we started.

Many of us have come far, indeed. And we don’t deserve our own dissatisfaction with ourselves – we deserve to celebrate our successes. Sure, we’ve fallen short of some ideal, all of us, but we’ve achieved real, measurable progress, and deserve full credit for that. So be kind to yourself, and please don’t beat yourself up when you haven’t attained an over-lofty goal.

One way that Dan Sullivan offers help is to encourage us, at the end of each day, to find three successes, or “wins,” we’ve accomplished today. Given everything we do in a day, there are likely three things we’ve successfully accomplished every day. Twenty-one successes per week. Document them.

We should count our successes as we do our blessings – and practice the same intentional gratitude for what we have accomplished. I am not advocating the “give every kid a trophy” philosophy, but recognition and appreciation of actual accomplishments.

How do you keep your focus on what you’ve truly accomplished, as opposed to only measuring how far from your ideal you are?

Please click here to email me directly – I’d love to hear your strategies.

Until next Wednesday –



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