the plan

The other day someone asked me what I was going to do next. I said, “for the first time in my life, I haven’t really thought about that… for over a year.”

My philosophy on career planning is this: always be open to options. When an option presents itself, discern whether it is more interesting than the current path. If it is more interesting than the current path, pursue the option. If it is not more interesting than the current path, stay on the current path. People who are most interested in and engaged by what they are doing are the most successful. (And happiest.)

This philosophy is directly opposed to the career planning advice I got in college and grad school: make a 10 year plan and then follow it.

If you had told me 10 years ago that I’d be doing what I’m doing right now, and all that I’ve done along the way, I would have laughed all over you.


My generation suffers from a path addiction. (No, not that Path.) Thanks, in part, to over-parenting, we are placed on a path from the moment we can walk and we follow it. And it becomes delightfully comfortable.

We get put in preschool, then grade school, then we are prescribed extra-curriculars. Then we go to junior high school. High school comes next and then after that college. Always working toward the next step on the path. In college we are coached to develop “10-year plans.” Super-paths! And then we graduate. Real world. Shock. Horror.

Lately, as I have counseled friends on career decisions, and as I’ve started offering advice to recent college grads, I’ve learned something: we spend way too much of our early years knowing (and being prepared for) what’s coming next. When we finally get to the part where we have to fend for ourselves, develop a course of action and then execute, we fall down. Hard.

When offering guidance, I’ve too often been met with “but I’m not qualified for that” or “nobody would believe I’m capable of that.” We believe that, because someone else is doing something, they must have been anointed to do so. We think, “someone, somewhere validated that role.” I’d offer that the opposite is more likely true: most people aren’t qualified to be doing what they’re doing. Instead they were presented with an opportunity, and rather than waiting to be told they were ready, they simply jumped at the chance and figured it out as they went.

There’s a favorite passage from The West Wing:

Leo McGarry: Because I’m tired of it: year after year after year after year having to choose between the lesser of who cares. Of trying to get myself excited about a candidate who can speak in complete sentences. Of setting the bar so low, I can hardly bear to look at it. They say a good man can’t get elected President. I don’t believe that. Do you?

Jed Bartlet: And you think I’m that man?

Leo: Yes!

Bartlet: Doesn’t it matter that I’m not as sure?

Leo McGarry: Nah. “Act as if ye have faith and faith shall be given to you.” Put another way: Fake it ‘til you make it!

Fake it ’til you make it. Or: put down the path. Step away from the plan. Blaze your own trail. You are what you say you are – and nobody else needs to validate that. In fact, nobody else can.

our second screen obsession

Hollywood has grown fixated on the second screen. The “second screen” refers to the other thing we’re paying attention to while watching television or movies – this could be a phone, tablet, or computer.

The industry fixates on the second screen because it feels threatened, and rightly so. In an era of alt-tab attention spans, fewer people are coming to long-form content by traditional means if they are coming at all. Between the actual dollars, and the perceived mental commitment, the cost of consuming content that is longer than your regular cat video on YouTube is not negligible.

Further, over the last 30+ years, as distribution channels have expanded (the movie multiplex, the 500+ cable television channels), quantity of content has increased while quality of content has decreased. Fortunately for Hollywood, this bad content didn’t have much to compete with in order to capture an audience.

In the late 1990s, we saw wide-spread consumer adoption of the Internet. And the rise of file sharing. And the slow-and-then-fast disruption of the recorded music industry.

Hollywood watched this happen.

Then came broadband. And suddenly it was easy to share and stream the larger video files that dialup couldn’t support. And Hollywood started to worry, mostly, and incorrectly, about piracy.

Then came Facebook. And suddenly there was a whole new type of content that was, in many cases, far more compelling than Hollywood’s. This content is always fresh, and, most importantly, it is free. This is social media.

Then came the iPhone. And suddenly consumers could take this new stream of social content with them wherever they went – including the couch and the movie theater.

And now we have arrived at the present model of consumer behavior where viewers are watching Hulu in one tab while they’re Facebooking in another, they’re playing Angry Birds on the couch while they’ve got ESPN on on the television, and they’re texting each other while they’re in the movie theater.

And, bizarrely, Hollywood’s reaction to this is: LET US OWN THIS NEW SCREEN.

Thus is born the “innovation group” at BigMediaCo. Thus do ex-producers decide to launch startups to “capture the second screen experience.” Thus does an entire industry begin to wonder if this Silicon Valley place might become “a thing.”

Every few weeks, I get pitched a second screen opportunity, mostly by people who are content creators in Hollywood. Most of these businesses provide access to bonus content related to the first-screen experience, allow viewers to socialize with other people who are also consuming the first-screen experience, or, most commonly, create new revenue streams related to the first-screen experience.

And it’s started to make me wonder… are we stupid?

The job of Hollywood is to create content (read: tell a story) that so delights an audience that the audience is willing to pay to consume this content. Why is Hollywood spending any time creating experiences to further distract the audience? Rather than fixate on the shiny new thing, shouldn’t Hollywood be doubling down on finding and telling incredible stories? Wouldn’t we put our second screens down in a heartbeat if we were actually being delighted by the content on the first screen?

Social media has made it nearly impossible to recoup the investment in bad content. Mediocre opening weekends of a bad movie thanks to a big marketing spend are no longer possible. Twitter kills a bad movie after the first few screenings on Friday. But content is still king. And good content spreads itself. Social media has also spawned a whole new consumer behavior: Incredible television can now be discovered and binge-viewed season-by-season online. (see: Downton Abbey).

Let’s pause. Let’s not take our eye off the ball. Let’s not pretend that the second screen is going to solve some underlying structural problems in the entertainment industry. Let’s instead be confident that we can tell wonderful stories, delight our audiences, and that in return our audiences will reward us with dollars and, more importantly, their undivided attention.

take the plunge now

The following appeared originally at the Harvard Business Review.

I am not a risk taker.

I have a fine arts degree in film. Instead of moving to Brooklyn to rough it as an indie filmmaker and bartender, I moved to the Upper West Side and took a job producing television for Disney’s ABC. Classmates told me I had sold out. Well, salary and health insurance are powerful incentives.

Years later, I attended the MBA program at Harvard Business School. I loved it and made great friends there, but it was hardly risky.
After HBS, I returned to Disney in a role many would have envied. I have always loved the company’s products, but quickly fell out of love with its processes. I wanted to create impact, but I didn’t want to spend years playing politics and riding the corporate ladder before I could contribute meaningfully.

Entitled? Perhaps. Impatient? For sure.

After one particularly maddening day at work, I made a comment about how the mentality of “that’s not how we do things around here” is such a threat to innovation. A friend of mine pounced. His startup was in need of a product person.

I knew I wanted to be an entrepreneur — eventually. But I was waiting for the right thing and the right time. Or so I always told myself.

In reality, the fear of failure was keeping me from taking the plunge. I don’t think I’ve spectacularly failed at anything in my life. Why would I want to start now? I cared way too much what others would think of me.

It was hard to get over that. Friends and family kept telling me: “Who cares how it ends? Think of everything you’re going to learn and discover along the way.” They were right.

The fear of failure tempered, the time was right, and a start-up couldn’t have been a more perfect destination. My life had revolved around developing media, technology, and incredible consumer experiences, and this new venture tied all three together.

I’ve been the product guy in a small team, where I have a big impact, for over six months now. I love having skin in the game.

Entrepreneurship is highly romanticized, especially right now. It’s not easy. It’s not at all what they make it look like in the movies. Startup life requires a little bit of crazy and complete rejection of the fear of failure.

That’s an oversimplification, of course. There are times where I wake up at 4 a.m. in a cold sweat, worrying about something related to our product. There are nights where I don’t fall asleep, pondering the additional debt I’ve incurred on top of my student loans.

Still, I’m comforted knowing I’m not alone. I have exceptional cofounders; teammates who are committed to unwinding me when I go fetal. I have incredible friends who are building their businesses; my personal board of directors that I can ping at any time.

Having jumped off the cliff, I couldn’t be happier. I’ve never worked harder on anything else in my life. But nothing has ever felt less like work.

Steve Jobs passed last week, as we all know. What better lesson to have imparted than his? Death is the absolute worst thing that can happen to you. And it will.

Why not take the plunge? Make something while you’re still alive.


I’ve now spent 24 hours with the iPad. Everyone keeps asking what I think of it, so I’m formalizing my thoughts and posting them here:

The device:

It’s pretty. This is no shock, coming from Apple, though I do find myself impressed with the quality of the display every time I fire it up.

The battery is good. Pogue said 12 hours of straight video play. Haven’t tried that myself but at the rate things are going, I’d believe it.

Downside: it does not charge when plugged into my mac (older machine) and the cord isn’t really long enough to plug into wall and continue playing with it, so you do have to take a break when you want to charge it. Fortunately the battery seems good enough that that shouldn’t be a problem.

The thing is heavier than a kindle and holding it for a while, while not painful, can get awkward. I got a case. I’d recommend it.

The content:

The Apple apps (mail, calendar, etc) are top notch. They feel like they are the full incarnation of what the iPhone version wanted to be. Disappointingly, Apple does not provide a native chat application (still) which feels like a missed opportunity for the device – perhaps that will come in the next OS.

The third party apps I’ve tried so far are also quite impressive. There does seem to be a thinness around the offerings at the moment though, particularly among the free ones. Also, there is no Facebook app, which seems weird to me. I’ve been much less active on Facebook because of that.

File handling is an annoyance. I can’t download a PDF from the web to view later (I can bookmark it and view it in safari – but there is no way to get the file in an offline state – and no way to mark up the PDF unless it’s imported into Pages – which I can only do if I email myself). Access to Mobile Me iDisk (available on the iPhone) is also noticeably absent.

One would presume the apps will catch up as they begin approving in the iTunes Store again this week.

The experience:

The thing moves fast. I imagine that the next iPhone will also process this quickly and finally we will have a powerful smartphone instead of just a smartphone. The apps all load quickly, video runs beautifully, the speaker is good enough quality to watch tv shows with.

Most importantly though, is the lack of multitasking. This will upset power users, but I found myself consistently more relaxed as I was doing only one thing at a time instead of the usual 4 or 5. I wonder if this will help combat ADD overall – I doubt it.

(I should also add, that while typing is obviously not as good as with a keyboard, it is lightyears better than with the iPhone. I can type at near keyboard pace on the iPad screen.)

So what?

Ya, I agree with the sentiment that this device is more about consuming than creating. But I’m okay with that. It’s been a pleasure to consume with it so far and I do now understand the middle zone between the phone and the laptop that this device will serve – I was skeptical about it before.

The verdict: if you like toys and consume a lot of media, it’s worth the add. But yes, there will likely be a slightly cheaper, better one in 12 months. (That said, this does not seem to suffer from the bugginess or rough first outing effects that iPhone 1 did – so don’t make that the excuse.) I like mine, and it’s been an excellent couch companion for the past day.

This post was written from the iPad.