Win big & Lose small and often

Boss, IT Business
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In business it’s nice to win big. Doesn’t always happen so when it does – enjoy it.

It’s more important to lose small. And often. So long as you’re learning from it – not that you will ever learn how not to lose (or even how to lose gracefully) but recognizing the factors that contributed to the loss and how to spot them in the future.

Most people have a tendency to win small and lose big. Almost like a blind religious faith – there is a hope that a loser will magically turn into a winner:

Fact is, there is no easy tell if a bad situation will improve or get much worse with time. It’s not up to you: Your choices are binary: Stick with it or cut your losses. In fact, you only have one guaranteed outcome of a bad situation through cutting your losses by making them finite. The other variable outcome is if things change – could be better or could be worse…

So your only choice with clear certainty is to stop being a loser right now

That’s not a fun choice.

Even the most pessimistic people will not quit.

It sucks to lose.

The ego gets in the way of us admitting to ourselves we screwed something up.

And if we went into the decision with the rational thinking.. it’s only a matter of time till our fortunes turn around, right?

How much worse could it get, right?

If you quit now you’d lose – but if you stick with it then it will work out eventually, right?


Wrong, wrong, wrong.

If you were right, things would have worked out and you wouldn’t be in this predicament. You were wrong, cut your losses and move on.

If things couldn’t get much worse then why did you do this to yourself in the first place? You were wrong, cut your losses and move on.

Even if things work out eventually, there is still a huge possibility that things will get much worse in the meantime. And what about all the time that is passing by with you losing while you could be working on something more productive? You know any Y2K specialists or OEM box builders sitting around waiting for SBS 2013? Nope, they now sell cars and real estate.

If you gotta be wrong, be disciplined about managing your losses and move on to the next thing.

Manage your losses.

Define them up front and evaluate them when you encounter them.

Then choose to move on.

The Art of Failing

foxyNow I have to admit that I do not know the secret of when a fail is a fail: and most of it in my personal experience has been a result of poor planning and misplaced optimism. I’ve definitely made some bad hiring choices but I let the folks linger on payroll for far too long. Ditto on some projects and investments and solutions (remember CloudBlock) and a metric ton of features that went nowhere. I still have a few hundred SecurID tokens sitting somewhere.

Unless you are going to become disciplined, insightful and judicious overnight the game is to document and revisit losses often so you do not keep on putting yourself in losing situations. So that when you inevitably put yourself into a losing situation again you know to get out of it and focus elsewhere.

Most importantly, it’s the courage to admit that you were wrong. Your ego won’t like it.

But as I tell my ego often: You don’t write Corvette & Ducati checks. And if I was such a f’n genius, how did I end up in such a f’d up situation in the first place?

The sound of silence after that conversation is earth shattering. Cause ain’t nobody…

P.S. If you get the reference, congratulations Smile