Amazon and Apple Make Business-Crushing Mistakes On Purpose, So Why Can’t You?

Almost any top 10 list of the biggest technology product flops of all time will include a reference to Apple’s Newton and Amazon’s Fire Phone. But they will also note that the Newton was the precursor to the iPhone, and that the Fire Phone indirectly birthed the Amazon Echo.

Failing forward is a known business concept, especially in the arenas of entrepreneurship and innovation. But turning failure into success is not just a switch you can flip. The wrong mistake can shutter your business almost instantaneously. So if you’re going to make business-crushing mistakes on purpose, you should have forethought going in and fortitude coming out. 

I’m not spinning out the next iPhone or Alexa, but I make my share of potentially business-crushing mistakes. The learning process is the same. So here’s a mistake I just made on purpose and what I did about it.

Planned Mistakes Are Never Actually Planned To Be Mistakes

Don’t let my wordplay undercut my point. I’m aware of the oxymoronic nature of the “planned mistake.” And I loathe the phrase “fail forward.” The terms are just too on point not to use. 

Failing forward isn’t something you attempt. It’s not even something you consciously do. It’s simply the collection of experience and wisdom that comes from having made a bunch of mistakes in the past, when your “educated guesses” turned out to be hilariously off base.

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

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

Basically, I was expanding 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, and crossed it, which upset a lot of folks in my existing customer base, my target market, and the adjacent market. 

So essentially, one night I went to bed feeling good about the plans I had just executed. The next morning I woke up with a lot of people pissed off at me.

That’s a microcosm of how planned mistakes usually play out.

The First Thing You’ll Want To Do Is Erase It

I consider myself a sort of business person who would rather be respected for my actions than my money. I’m not pumping my ethical bona-fides, and I know I’m not an anomaly, but I will tell you that if you approach business (and life) that way, you have to walk a very fine line. That line can get blurry sometimes, and of course, when you step over it, you ultimately feel horrible about it and want to undo it.

Experience has taught me you can’t. 

One of the most important but painful lessons to learn about making mistakes is you can’t reset the timeline, you need to spend all of your energy fixing the timeline you just created. 

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

The Next Thing You’ll Want To Do Is Quit 

I’m serious about this. One of my Teaching Startup advisors and fellow serial entrepreneur Rachel Greenberg wrote this great piece on mistakes aspiring startup founders make, and in it, she says this:

“So many impatient entrepreneurs make drastic changes or quit altogether when success — or the tweaks required to obtain it — is right around the corner.”

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

But in reality, my product was fine, my delivery sucked. That means don’t change the product. And don’t restrict the product by putting breakers in place to make sure what I just did can’t happen again, just don’t do it again.

The Thing You Must Do Is Figure Out What To Take Away

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

What Apple and Amazon ultimately did was the same move I needed to make. A mistake will always tell you what you shouldn’t do, but just as often, it’ll uncover one or more things you should start doing. 

Finding opportunities in the rubble is not easy, mentally or emotionally, but the only way to become good at it – to learn to fail forward – is to start digging through that rubble to look for pieces 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 would go on to become Alexa. For me, it was a wall I needed to build to fortify both my existing 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 it happens, you need to put instinct aside and start digging.

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