Why Steve Jobs Was Wrong


Remember this famous quote from Steve Jobs?

“You can’t connect the dots looking forward, you can only connect them looking backwards. So you have to trust that the dots will somehow connect in your future.”

With this statement during his Stanford commencement speech, Steve gave all of us a free pass to stop worrying about our future. I know I did.

That speech was given in 2005, the same year that I graduated from college. I first watched his speech on YouTube nearly 2 years later. At that time, I was well into my first “real” job and the reality of my situation had set in. I had worked since high school to attain this well-respected, six-figure job as a financial analyst, and now that I was there, I hated it.

If I could be so wrong about this, how do I know what to do next? How do I make any decisions to move forward? I lost all confidence in my own abilities to figure out what I wanted to do – and I was hopelessly confused.

“Am I going in the right direction?”


It’s a question we all ask ourselves on a regular basis. So when someone as successful, knowledgeable, and revered as Steve Jobs gives you a free pass to literally trust in some divine plan, it feels like a huge weight off of your shoulders. Thanks Steve!

So I kept on truckin’. I kept collecting my paycheck, thinking about what Steve said, waiting for the moment to strike when everything made sense – when all of my dots connected.

Weeks went by, months went by, years went by, and my dots were still a scatter plot of confusion. I still hated waking up every morning, and I didn’t know how to fix it. I tried to harness my inner Steve and tell myself not to worry, trust the dots. But each time it was a much more difficult pill to swallow.

Ummm, Steve – my job still sucks, I hate what I do on a daily basis, and now I’m even more anxious about my future. At this point, not only are there no dots looking forward, the dots looking backwards make me depressed!  –  My brain

c4That’s when it hit me, Steve Jobs was wrong! The dots weren’t going to connect on their own.

So I quit.

Not only did I quit, but I quit in early 2009, a time when the entire world said we were headed for the second great depression! I had no plan, but I was forcing movement. I was changing my path purposefully, and my life finally started to move in the right direction.

When you are unhappy with your current situation and you can’t figure out what to do next, do not trust that the dots will connect – force yourself to create new, exciting, terrifying dots.

To trust that the dots will connect, as Steve recommends, is to subscribe to the notion that all dots are created equal. Because if in the end it is all going to make sense, why make the difficult decision? Why force yourself into uncomfortable territory?

Think about this –  as you lay on your death bed (let’s get morbid here for a second), you look back on all of the things that have occurred in your life. Some moments are good, others are bad, but in the end they all have a seemingly obvious flow. You remember the moment you met your significant other, you had your first child, you got your first job, etc. The dots connect.

Of course they do, they have to! Our life is made up of moments.

“How we spend our days is, of course, how we spend our lives.”
-Annie Dillard

What you must realize is that these events, these “dots”, didn’t just happen to you – you decided to make them happen. You went to the bar and met your wife, you went on the job interview, you purchased your house in that specific neighborhood. And the scary truth is, some decisions are better than others. All dots are NOT created equal.

Additionally, it is MUCH easier to create easy, boring dots, than it is to create amazing dots. Here is a great quote on this subject, taken from the book Thinking, Fast and Slow, by Nobel Prize winning psychologist Daniel Kahneman:

A general “law of least effort” applies to cognitive as well as physical exertion. In the economy of action, effort is a cost, and the acquisition of skill is driven by the balance of benefits and costs. Laziness is built deep into our nature.

Your life can either be made up of small, normal, safe dots, or huge, colorful, extraordinary dots! But it is a decision you have to make for yourself, and you are going up against our default mindset of laziness, safety, and inaction.

Lucky for us, laziness has a kryptonite – purpose.

If you want to achieve something amazing for yourself, you have to work towards it with a purpose.

purposeYou have to write it down. You have to see it every day. You have to smell it, taste it, and feel it. This purpose will push you through the laziness and force you to create tons of NEW dots.

The irony is, perhaps no one understood this better than Steve Jobs.

Even Steve didn’t just trust that it would all make sense in the end. He put in the hard work. He made incredibly brave, immensely unpopular decisions nearly every day (dropping out of college, focusing resources on the iPod ) that made him a man worthy of all of the praise and reverence.

He forced himself to create so many huge, bright, amazing dots that when they all connected in the end, there was no possible outcome other than a truly exceptional and inspiring life. Which is exactly what I want for you, and I’m sure what you want for yourself.

So how could someone so smart and purposeful tell others to trust in the connection?

Well, as many of you have probably already  guessed, there is more to his quote than just these two lines. However I thought it was important to highlight these two lines, as these are the ones most often regurgitated and repurposed. In the world of the tweet, sometimes we miss out on the full message, which can be a recipe for disaster.

The last portion of Steve’s message is as follows:

You have to trust in something: your gut, destiny, life, karma, whatever. Because believing that the dots will connect down the road will give you the confidence to follow your heart, even when it leads you off the well-worn path.

Here we have the most important part of this idea. Steve is not saying that everything will be all right in the end. In fact, he’s not even saying that “your gut, destiny, life, karma” will actually be right!

What he is saying is that you have to be willing to put your trust somewhere because the journey will be difficult, and you will be tempted to stay on the well-worn path. He’s saying that following your heart is so difficult that you need to have a place where you derive strength from to keep pushing through.

I say put your faith in purpose. 

Put your faith in the life you want to create, the life you want to look back on and admire from your death bed, and you’re guaranteed to create some incredible dots.



P.S. – Check back in the near future for some great worksheets and tips on creating purposeful action! Or even better, sign up for the newsletter at the top right of this post and I’ll send the worksheets directly to your inbox.

1 reply
  1. Jesse
    Jesse says:

    Though it may actually provoke some to take action, perhaps even risky/beneficial action, I think you are correct to point out the potential danger of embracing faithful/wishful thinking. One can operate believing/trusting that things will work out and make sense in the end (that the dots will connect), but simply adhering to this belief alone won’t necessarily make it so. Again, I think you’re right to identify action as being the missing ingredient. Granted, I doubt Steve intended to offer some sort of a “free pass” that would be obtained through inaction and self-inflicted delusion. However, I think his wording was just cloudy enough to call for a bit of clarification and I appreciate you providing us with it.

    You end your article by offering an instruction/suggestion and affirmation: “Put your faith in the life you want to create, the life you want to look back on and admire from your death bed, and you’re guaranteed to create some incredible dots.” I think this closing may unintentionally reignite the same confusion your article was meant to extinguish. I would suggest replacing the word faith with effort, and withdrawing the guarantee. I’m not trying to split hairs here, just as you weren’t with Steve, but it seems that simply putting your faith or even effort into the life you want to create and look back on won’t “guarantee” the formation of “incredible dots.” Many people put their faith and full effort into the lives they want to create and their dreams just never take the desired shape; sometimes they are even filled with incredibly bad dots. In addition, a person could successfully create the exact life they want, but it being considered incredible by any known sense of the word would still depend on what that life actually consists of. I think these distinctions are important to make.

    We all have to determine what “incredible dots” really are, while knowing that faith and action are not guaranteed to bring them about (and that’s okay!), and that some people may currently be confused as to the definition. I’d love to know more about your thoughts on this subject, perhaps in a future blog post! Thanks for the thought provoking article; I look forward to reading the next one!

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