My Interview with Steve Jobs (Timeline: 2020) Redux

| The Flashback Files

Background: In 2008, I was worried about Steve Jobs’s health. I wrote this fictional interview, placed in the year 2020, as a way of expressing those feelings. The scenario for Apple’s future without Mr. Jobs was a kind of ghost of Christmas future warning of what could be, not a heartfelt prediction of what must be.  So, here’s the fictional interview, in the year of Mr. Jobs’s 65th birthday, with prescient references to the year 2011 and the future iPad, exactly as it appeared in December, 2008.


As I pulled up to the long, curved driveway, I thought about the irony of the date. Hindsight, they say, is 20/20, and I was to do my interview with Steve Jobs on December 20, 2020.

At the iron gate, some very large security guards, dressed in black, scanned my I.D. card, frisked me and took photos of me and my Prius. One was Asian, looked like Odd Job, and seemed like he could wrestle a wooly mammoth — and win.

Odd Job escorted me into the huge house via a back entrance and walked me down a long, dark hallway. We finally arrived in what looked like a large study, dimly illuminated, with a high ceiling. The large hardwood floor and drawn drapes distracted me as I noted only two black leather couches and a grand piano. That was all. No book cases, no TV, no rugs. Nothing warm and bright and alive.

As I was led toward the couches, I saw a dim figure siting in the lotus position, reading something on his iPad. He looked up, waved at Odd Job to leave, and brushed his fingers at me. I figured that meant to sit down. Mr. Jobs was wearing jeans, a soft white, pajama-like shirt and sandals.

We exchanged some minor pleasantries, nothing remarkable, and finally I realized Mr. Jobs, now 65 years old, was staring at me — coldly.

Jobs: So. You have questions?

TMO: Let’s start, if that’s okay, with your reclusiveness. You haven’t granted an interview or even been seen since you left Apple in 2011. Why is that?

Jobs: There’s no one I need to talk to. My work is done.

TMO: But surely, you realize you’re an American icon. People want to know how you’re doing.

Jobs: I couldn’t care less.

Determined not to be taken back by warnings that Mr. Jobs would often be curt, I forged on.

TMO: What are you doing these days?

Jobs: [smiles weakly] Well, I talk to Phil [Schiller] a lot. And I play the piano. Laureen and I go for walks.

TMO: And Laurene is fine?

Jobs: Laurene is fine.

TMO: What do you and Phil talk about?

Jobs: Well, ever since he left Apple last year, he’s been playing a god-awful lot of golf. He loves Rancho Sante Fe. We chat about the old days. The other day, I was kidding him about the time I talked him into jumping out a two-story window at Macworld New York. He never forgave me for that one…. I have to call him on his iPad. He’s never home.

TMO: Let’s talk about the decline of Apple. When do you think it all started?

Jobs: I think it all started when we decided to pull out of the expos. I think our last one was 2010. We, by that I mean the executives and engineers, stopped connecting with our customers.

TMO: Actually, your last Macworld keynote was 2008. So what led to the decision to pull out?

Jobs. We noted that we spent about five million dollars on Macworld S.F. Twice as much for New York. And we’d get about 40,000 looky-loos in four days. Not a single one of them was a paying customer. But we were getting a million people a week in the retail stores, every one of them had a credit card, ready to buy something. So we decided the ROI for the expos sucked.

TMO: And you just got tired of doing keynotes…

Jobs: Yeah, that too.

TMO: In hindsight, do you think that was the beginning of the end?

Jobs: Phil and I talk about that. What we lost sight of was that there is a community of customers, journalists, who kept the fire going. At the expos, they fanned those flames, especially when I gave the keynote, and it percolated through out the Internet for months. But as we pulled back from twice a year, then once a year, then zip, the jazz went away. Poof.

TMO: And the company got boring?

Jobs: In a way. We thought the success would last forever. When you’ve been winning for a long time, you forget how you got there. The dollar ruled us.

TMO: Apple hasn’t had a big success since the iPad in 2010. Why do you think that is?

Jobs: It’s hard to say. Maybe there comes a time when the magic of an era fades. We sat back and sold iPhones and Macs, then iPads, made a lot of money, but our new guys who came along never got into the fever, the culture of the Mac. I isolated them from the public. Then customers started to take us for granted, while we counted our money.

TMO: Apple became just a big, rich, secretive company, with blasé customers.

Jobs: Something like that.

TMO: If you had it to do all over again, what would you change?

Jobs: I would have hung around longer. Kept doing the shows. Kept the fever, the passion alive.

TMO: If the ghost of Christmas past comes to visit tonight, what will you tell him?

Jobs: [reflects for perhaps 30 seconds.] I wish I could have hung in longer, remained more visible, outgoing. Maybe I coulda been more accessible, stayed on as a spokesperson.  And given more of my money away to good causes with a splash. [pauses, frowns.] I never did want to be the richest dead guy.

TMO: With that, perhaps it’s time for me to go.

Mr. Jobs gave me my leave by dourly turning back to his iPad. What he found so alluring in that small display, I had no courage to ask.

I left the dark man and the dark, lonely room behind. He never looked up.

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John Martellaro

Back in 2008, some readers mistakenly took this fictional interview as statements of fact or bold assertions & predictions on my part.  I meant it to be read as fiction, speculation, and serious food for thought.  Read it as whimsy and ponder.


Thought-provoking. But the jeans would cut off his circulation in lotus. I?d put him in a sarong, maybe light denim.

It?s impossible to speculate with any accuracy where Apple will be in a year or two, much less a decade. However, it is fun to prognosticate to see how close one might be or even just for the fun.

How long can this amazing company continue to shake, rattle and role? What are the averages? One thing is for sure: All things are impermanent?all will eventually die.

Steve knows this. He has no worries.


Wow, were you smart back then and sooo able to predict the future.  Seriously, this self serving, rude and poor taste crap you provided today is as worthless now as it was then.  I only wish that Steve is around on his 65th to laugh at what has happened to journalism by 2020.  I noted that you failed to have predicted that part in your piece.  Will reporters be relevant in 8-10 years from now?  Naa, unpaid bloggers will rule the roost and repackagers will scoop it up and feed it to us in an app.  The Odd Job character in your piece will be the blogger and after it is published he will be looking for a new odd job.  Come on, the man is not well and to provide him as a centerpiece to this type of thing is just plain wrong.

Chandra Coomar

This is silly John. I am surprised since you seem to have some gravitas.
It doesn’t help that you repeatedly misspell the name Laurene.

I get the feeling you are short of ideas. This article would have been a fail in 2008 and I cannot see why it’s considered to have merit in 2011.

Shabby imo.


John, There are left brain thinkers and there are right brain thinkers and the left falls short in understanding or good manners. The left also lacks the sense in humour or the empowerment of taking chances.

or said more eloquently:

I am always doing that which I cannot do, in order that I may learn how to do it.
~Pablo Picasso

and for more words of wisdom for the inspired


I like the premise but felt like your 2008 “self” was putting words directly into SJ’s mouth making him admit he was wrong and “should” have been what the vocal Apple fans wanted him to be.

“Gee, I shoulda been a better friend to all the Apple fans and expo goers.  They know best how to run my company.”  That was you and your blogger friends talking, never SJ!

I have no doubt Apple will still be going strong in 2020, long after the SJ reign, at which point you might republish this again as way off-base humor.


Wow. Lots of negative responses, including some that want to paint the author into a box. How about some positives?

1. John does depict a Steve Jobs who is alive in 2020, and who was able to gracefully withdraw from the company he founded, saved and built into one of the most successful organizations ever.  And managed to beat his health issues, spend time with his family, and build his Woodside house.

2. John uses the future interview as a way to present an issue he sees developing within Apple now, an issue which could cause its unfortunate demise. And the irony of that.

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