Amazon and Apple make business-destroying mistakes on purpose, so why not you?


Almost every top 10 biggest tech flop of all time will include a reference to Apple’s Newton and Amazon’s Fire Phone. But they’ll also note that the Newton was the precursor to the iPhone, and the Fire Phone indirectly gave birth to the Amazon Echo.

Forward failure is a well-known business concept, especially in the fields of entrepreneurship and innovation. But turning failure into success isn’t just a switch you can flip. The wrong mistake can shut down your business almost instantly. So if you’re making business-crushing mistakes on purpose, you should have some forethought and courage.

I don’t run the next iPhone or Alexa, but I do make my share of potentially destructive mistakes. The learning process is the same. So here is a mistake I just made on purpose and what I did about it.

Planned errors are never actually planned to be errors

Don’t let my pun undermine my point. I am aware of the oxymoronic nature of “planned error”. And I hate the term “forward failure”. The terms are simply too relevant not to be used.

Failing forward is not something you try. It’s not even something you consciously do. It’s simply the collection of experience and wisdom that comes from making a bunch of mistakes in the past when your “educated guesses” turned out to be hilarious.

And I only use the term “hilarious” because I can laugh about it now.

I didn’t plan to make my last big mistake, it just happened when I lost focus. It was a self-inflicted injury, so it was “planned”, but I didn’t want to do it, so it was a “mistake”.

Basically, I was extending my marketing reach from my target market to an adjacent market. It was working, so I was getting more and more aggressive with my marketing approach. One day I found the line, shrugged it off, and crossed it, which upset a lot of people in my existing customer base, target market, and adjacent market.

So basically one night I went to bed feeling great with the plans I had just executed. The next morning I woke up to a lot of people angry at me.

It’s a microcosm of how planned errors typically play out.

The first thing you’ll want to do is erase it

I consider myself a kind of businessman who prefers to be respected for his actions rather than his money. I’m not pumping my ethical bona fide, and I know I’m no anomaly, but I’ll tell you that if you approach business (and life) that way, you have to walk a very fine line. This line can get blurry at times, and of course when you cross it, you end up feeling awful about it and wanting to undo it.

Experience has taught me that you can’t.

One of the biggest but most painful lessons to learn about mistakes is that you can’t reset the timeline, you have to put all of your energy into fixing the timeline you just created.

It starts with investigating what you did wrong, learning what you did wrong, and accepting what you did wrong. You can admit what you did wrong, you can apologize for what you did wrong. But words don’t solve problems, actions do.

The next thing you’ll want to do is stop

I am serious about this. Rachel Greenberg, one of my startup education advisors and serial entrepreneur, wrote this great article about the mistakes aspiring startup founders make, and she says this:

“So many impatient entrepreneurs make drastic changes or give up altogether when success – or the adjustments needed to achieve it – are just around the corner.”

I can tell you that the urge to quit or make drastic changes after a mistake is not exclusive to aspiring entrepreneurs. Although I never felt the need to close my business and, I don’t know, take up gardening or something, every instinct I had told me it was time to do a great pivot so that something like this can never happen again.

But in reality, my product was fine, my delivery sucked. This means not changing the product. And don’t restrict the product by putting circuit breakers in place to make sure what I just did doesn’t happen again, but don’t do it again.

The thing you need to do is figure out what to pack

Mistakes always come with lots of lessons, big and small. In the heat of post-error correction, it’s tempting to amputate when other surgical solutions will do.

What Apple and Amazon finally did was the same thing I had to do. A mistake will always tell you what you shouldn’t do, but just as often it will reveal one or more things you should start doing.

Finding opportunities in the rubble isn’t easy, mentally or emotionally, but the only way to get good at it – to learn how to fail – is to start digging through that rubble for parts you can use.

For Apple, it was a computing form factor that was 10 years too early. For Amazon, it was the voice interface that was to become Alexa. For me, it was a wall that I had to build to fortify both my existing market and my new market.

I can’t tell you what opportunities you’ll find when you blow something up. But I can assure you that when that happens, you have to put instinct aside and start digging.

The opinions expressed here by columnists are their own, not those of


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