Thursday, December 4, 2014

Google, plus our past = the future of photos

A couple years ago, I wrote about my first serious attempt to organize my family’s photos. 50,000 digital photos spanning more than a decade — scattered across multiple computers, phones, cameras, and hard drives. It wasn’t a bad first attempt, but if I’m perfectly honest, it required a fair bit of work to keep it current. Which means it was out of date pretty quickly. (And it’s just as well: my middle child repurposed the photo server earlier this year to be a Minecraft server.)

Then I remembered the photo albums. Dozens and dozens of photo albums. Actual dead-tree, hold-in-your-hand, photo albums. Photo albums from my childhood. Photo albums from my wife’s childhood. Photo albums from our early, pre-digital life together. Photo albums from grandparents, passed down to us when they died.

Photo albums that none of us had looked at in years.

So naturally I got rid of them.

Read the full post over at Medium.

Monday, August 12, 2013

Measure twice, cut once

Finally got a chance to try out writing on Medium, @ev's new platform for writing on the web. I loved the experience, and expect I'll use it some more in the months ahead to get out a few other posts I've been thinking about.

I wrote about a tough decision we made in 2010 to shut down Blogger's oldest feature: FTP publishing. (Back in 2010 I wrote about the announcement here.) The gist of the post is captured in the quote below, but I encourage you to read the whole thing.
It’s easy to say yes when a customer (or prospect) asks for a new feature: after all, if it’s just a day or two of engineering time, why not? But you quickly lose sight of the product you’re building: your product no longer has a coherent vision, and each new feature brings with it uncertain support costs that will last as long as the feature remains. Much harder — but much more important — is the discipline to question whether the feature is a required piece of what you’re building. New or old, easy or hard — if the feature does not support the overall product goals, it has to go. Customers and team-members alike respond to that discipline — particularly if it results in better support, more predictable development, and a clearer understanding of what it is you’re trying to build.

Tuesday, May 14, 2013

How Google sets Goals: OKRs


(cross-posted from the Google Ventures Startup Lab blog.)
On the day Google’s acquisition of FeedBurner closed in 2007, it was also the first day of a new quarter at Google. My new manager at Google asked me to draft my OKRs for him to review. I had no idea what he was talking about.
I’ve now gone through the process of setting my Objectives and Key Results (OKRs) 24 times, and each time I marvel at what an effective mechanism they are for focusing my effort as well as aligning my work with the company’s objectives. Last fall, I led a workshop about OKRs at the Startup Lab, which we’re making public today.
John Doerr originally presented OKRs to Google’s leadership in 1999 when Google was less than a year old, and they’ve been in use ever since. In the video, I present a portion of John’s original deck, then lay out how we’ve implemented them at Google over the years. I also shared a few of my OKRs from my time as a Product Manager on Blogger, and answered some questions from the employees at our portfolio companies who were present for the workshop.
Though the video goes into more detail, here are a few keys to what make OKRs work at Google:
  • Objectives are ambitious, and should feel somewhat uncomfortable
  • Key Results are measurable; they should be easy to grade with a number (at Google we use a 0 – 1.0 scale to grade each key result at the end of a quarter)
  • OKRs are public; everyone in the company should be able to see what everyone else is working on (and how they did in the past)
  • The “sweet spot” for an OKR grade is .6 – .7; if someone consistently gets 1.0, their OKRs aren’t ambitious enough. Low grades shouldn’t be punished; see them as data to help refine the next quarter’s OKRs.
One comment: in talking recently with one portfolio company who’s implemented OKRs, I realized that I should have been more emphatic in pointing out that OKRs are not synonymous with employee evaluations. OKRs are about the company’s goals and how each employee contributes to those goals. Performance evaluations – which are entirely about evaluating how an employee performed in a given period – should be independent from their OKRs. We’ll cover employee evaluations in an upcoming workshop.
About the Startup Lab workshops
Since its inception, the Google Ventures Startup Lab has held more than sixty workshops. These sessions are open to every employee of our 160+ portfolio companies and are held on a variety of topics: everything from privacy to Javascript testing to business development. Speakers are drawn from experts at Google and beyond. More than 95% of our portfolio companies have attended at least one workshop, and our recorded talks have been viewed thousands of times. We began releasing public versions of select workshops to share with the broader entrepreneurial community, and will release new videos several times a month.
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Thursday, March 14, 2013

Tips on renting an RV

Each year for the last four years, my wife and I have rented an RV and taken our kids to visit some of our national parks. In that time, we've logged nearly 6,000 miles and we've visited the Grand Canyon, Zion and Bryce, Columbia River Gorge, Lassen Volcanic National Park, the Hoh Rainforest, and Olympic National Park. (Not to mention a number of wineries, parks, coastlines, and a bunch more.) This year, we're visiting Joshua Tree and Death Valley, and will swing back through Las Vegas on our way back to the Bay Area. It's safe to say that every year the spring break RV trip is one of the year's highlights.

Whenever we do this, friends inevitably want to know more about the experience. After collecting questions on Google+, Facebook, and Twitter, I'm going to try to cover what it's like, what we wished we'd known, and we've learned since we started.

First, let's do the numbers:

  1. Rental cost. This is almost always the first question. Our first year we rented from Cruise America; for the last two years we rented from El Monte RV, and this year we're renting from a local outfit that rents privately-owned RVs. For for the first two, prices ran about $100/day and included a set number of miles; you'll pay $.30-.40/additional mile. The local outfit is more expensive; I'll explain why we picked them over the others below.
  2. Gas. You should expect your RV to get somewhere around 8-10 mpg, so it should be relatively easy to figure out about how much you'll spend on gas by dividing your total trip distance by that number and multiplying by the cost of a gallon of gas.
  3. Lodging. We've paid as little as $20 for a night in an out-of-the-way RV park and as much as $65; I'd guess the average is somewhere around $40/night.

On a week's trip that might be 1500 miles, you might pay $800 for the RV, another $250 for the mileage, $700 or so on gas, and around $300 for lodging. All-in (not counting food, more on that in a minute) you're looking at around $2k. Not a bargain, by any stretch. But keep in mind that that's transportation and lodging; for us, the equivalent in airfare, hotels, and car rentals would easily exceed that number. (And it probably goes without saying, but if your trip doesn't involve as much driving, you'll save on mileage and gas costs, potentially significantly lowering that number.)

How big is the RV? What's "Class C" mean? "Class A"?

We've progressed: our first RV rental was a 25' Class C; the next two years we rented a 26' Class C with a slide-out, and this year we're renting a very small 30' Class A. (I say very small because a Class A could easily be 40' long (or longer).) Each of those links gives you a good feel for what the layout of the interior is; the difference between a Class A and Class C is whether the RV is built on top of a van chassis (Class C) or is a whole vehicle (Class A). Moving from the 25' to the 26' slide-out was a big step up; the increase in living space when you're parked for the night is a huge win. Believe it or not, the five of us (and our dog!) didn't feel cramped. (We did feel cramped in the 25' RV in that first year.) The boys often went to the bunk over the cab where they could read or play their videogames; my daughter often used the table to work on her activities or read.

We'd seen a version of the RV we're renting this year (the Thor ACE) at an RV showroom near our home, and decided that we'd try to rent it if we could. That led us to find SF Bay Area Private RVs; we liked the layout of the RV, the nicer appointments compared with what we'd rented from CA and El Monte, and the possibility of having a slightly quieter cab when we drive.

What's it like to drive?

I won't lie: the first hour driving an RV was a bit nerve-wracking. The RV takes up all but a few inches on either side of a highway lane. It's unnerving the first time you get out on the highway and realize how close to the cars and trucks you are. But it was really just about an hour; after that, you get used to driving with the mirrors and using turn signals well ahead of any turns. Turning on surface streets isn't particularly hard either: keep an eye on the side view mirror, and start turning once your back tire is even with the turn you're making. Once you learn those techniques, you're good to go. Length doesn't really matter: you're driving a big vehicle. The width is what's noticeably different; the rest is details.

You do not need a different driver's license to operate an RV.

How nice are the RV parks? Who stays there?

This was a big unknown for us. Our first year, we picked parks out of AAA guidebooks and did pretty well. After a couple nights, we started seeing the name Woodall's in each of the lobbies we checked into; that's the bible of RV parks around the country. We now travel with the Woodall's book whenever we're on the road. One of the real perks to traveling by RV is the flexibility: if you didn't end up getting as far as you thought you would, just find a closer RV park and stay there! (Even when we're within the cancellation window for an existing reservation, we've found most parks to be very relaxed, and they often waive the cancellation fees. Worst case, you're out one night's stay – $30-40 or so.)

The parks themselves vary in quality; if you're on vacation, you'll want to avoid parks that are mostly long-term residents. (Nothing against them, but the vibe is less "vacation" and more "keep it down, we live here".) Almost every park has laundry facilities, many have pools and exercise facilities, and it's pretty common to find game rooms (ping pong, pool tables, arcade games). While we generally don't spend a lot of daytime in the RV parks, they can be a nice place to hang out and let the kids knock around. We've met families like us traveling with their kids, we've met a number of foreign tourists visiting the US (renting an RV and seeing the national parks is apparently the thing to do if you're German), and a number of retirees.

The food

It didn't really occur to us when we started out how convenient the RV would be for eating while on the road. The fridges and freezers in the RVs can hold quite a bit, and operate continuously off of either your propane tank or electricity when you're parked. (See "a full hookup" below.) I think we knew we were hooked in our first year when we pulled up to an overlook on the Southern California coast, parked, fired up the stove and cooked Easter Sunday brunch while watching the waves crash on the beach below. Since then we've had countless meals in incredibly scenic spots. Sometimes we eat while driving, other times we stop and bask in the view. Having the food nearby is a huge benefit. Another perk that we hadn't realized when we started: we eat a lot less fastfood when we're on vacation.

A "full hookup"

Aside from cost, friends seem most interested in how much you're "roughing it" in an RV. Putting aside the RVs that can run into the hundreds of thousands of dollars (be sure to check out Travel Channel's Extreme RV show if you're interested in those), we've found the experience to be surprisingly comfortable. The kids typically throw their scooters and a variety of toys into the storage bins, so when we show up at a new park, they can immediately grab a few of their things and get to exploring.

Each of the RVs we've rented has had a generator that can generate its own electricity (it uses gasoline from the RV's main gas tank as a fuel source, which means it won't run if the tank has less than 1/4 tank of gas), and a water tank and water heater so you have running water and hot water no matter where you are. That said, each RV park we've stayed at has had what's referred to as a "full hookup", which means they have electricity, water, a sewer line. Hooking the RV up takes about 5 minutes, and once you're connected, you can charge your phones/tablets/computers, watch TV, take a shower, etc. Though several parks also include coax cable for watching television, we've never used that. (DVDs for the kids, and Netflix on a laptop for us!)

Coupled with a fully stocked fridge and freezer, the reality is that we're always more supplied than when we were camping, and we generally have "our stuff" wherever we are. Compared to non-RV vacations where you've only got what's in a few suitcases, life in the RV always feels more comfortable and relaxed.

Oh, and if you are traveling with kids, don't overlook the tremendous win that is an always-accessible bathroom no matter where you happen to be!
Right... the sewage. How bad is it?

Not bad at all. I always keep a box of latex gloves in the cab, so that when we get to where we're going for the night, I can cleanly connect the sewer line. It's simple to connect, and in four years I've never been splashed with the "black water" (that's what they call the sewage; "gray water" is what comes from the water that goes down the kitchen and bathroom drains) when emptying it. We buy a package of treatment pellets at Walmart at the start of each trip; after you empty the black water tank, you drop one in the toilet and it eliminates any odors and helps break things down. (Let's leave it at that.)

We've spent nearly 30 nights in an RV so far over the last several years, and haven't ever once noticed an odor from the bathroom being on board. Non-issue.

But... will I be connected?

First things first: wifi at RV parks is often better than it is at hotels. That said, it's sometimes exactly what it is at hotels. I generally love being off the grid when we go on these trips. I turn on my out-of-office responder, turn my phone's sync feature off, and generally don't look at my work e-mail while I'm gone. That said, we frequently post pictures from the trip as we go, and often check in with family to let them know where we're at. As I mentioned above, we often watch a movie on Netflix or Amazon on one of our laptops after the kids go to bed.

While you can often count on wifi when you get to where you're going, one thing you often can't rely on is a cell signal while on the road. There were entire days on our trip to the Grand Canyon when we went without cell service. The lack of a data connection can be annoying if you're an e-mail addict, but if you were counting on Google Maps and your phone's GPS, the lack of a consistent cell signal will be a bigger issue. (Note that since that trip, Google Maps now has the ability to use the app in offline mode. More here.)

We invested in a handheld DeLorme GPS unit that came with a Spot Communicator, a satellite-based emergency beacon in case we were ever somewhere we needed immediate assistance. I'm ambivalent about both, as the DeLorme's interface feels like it was built by people who've never seen a modern phone UI (pretty sure this was their next project after creating the VCR clock), and the Spot is expensive for something we use once/year. That said, the combined safety and functionality are valuable, and they are not reliant on cell service. (I just noticed Spot has a new product, a satellite receiver that can pair over Bluetooth with your phone; let’s you signal an emergency as well as handle short data transmissions from your phone, which sounds like it might be a better option.)

Entertainment

When we're moving, the kids are always belted in. They may not need to be, but don't tell them I said that. I like that they can be spread around the RV – each layout will differ, but in general they can either be at a table, in a captain's chair or on a couch. They've each got their own area to spread out, can play games, talk with each other, or throw headphones on and play a video game or listen to their music. Unlike a car trip where they're on top of each other, this feels much less confining. And that's good for all involved! (I'll repeat: the convenience of the always-there bathroom is another thing to love about the RV.)

When we're driving, we have the option of running the RV's generator. That makes electricity accessible while you're moving, which means they can watch the RV's TV, their gadgets can be plugged in, etc. We generally don't drive with the generator on – fortunately for us the kids like to watch the world go by (that is, after all, one of the real benefits of traveling in an RV). But there's almost always some point in the trip when everyone needs the downtime, and it's a nice backup.

Our first RV didn't have a TV at all; each of the last several have had a TV and a DVD player. For as much TV as the kids watch, we don't actually watch much TV while on these trips. There was one point last year that it was raining at night, so we watched the Muppet Movie as a family. Made for a great night.

Maintenance/rental quality

Our experience with Cruise America was that the vehicles were in decent shape but a bit on the basic side. We are fortunate that El Monte's Bay Area location is just a few miles from our house, so it was easy to visit their building and see the various models first-hand. While we generally liked the vehicles we rented from El Monte, each of the last two years produced unwelcome maintenance issues.

With a slide-out, you have a section of the RV that extends from the main chassis. It makes sense that you'd want that section sealed so that nothing from the outside can get in. Much to our dismay, both of the vehicles we rented in successive years from El Monte had faulty seals, which meant that we ended up with water in the main cabin when we drove through rain. That made for a bit more excitement when driving than we would've liked, but in the end it meant that we used some towels to keep the floor dry. (And to El Monte's credit, they deducted a bit from our rental fee as compensation for the trouble.)

In addition to El Monte being local, we have a large RV showroom that's in the same town. In one of our visits there on a Saturday afternoon, we saw the Thor ACE – ACE stands for A/C Evolution, or a hybrid between a Class C and a Class A. The floorplan is a lot like a Class C (in particular the over-cab bunk where the kids sleep) but it has the overall design and approach of a Class A. We loved it.

Problem is, they're relatively new, and they aren't a popular rental model. Thanks to a Google search, I found SF Bay Area Private RVs. Curt runs the show there, and acts as a property manager for a bunch of private RV owners who rely on him to rent out their vehicles when they're not using them themselves. I like that we get an RV more suited to what we're looking for with less wear and tear, though it goes without saying that we're paying more as a result. (One benefit of going with El Monte or Cruise America: they're often located near airports, so you can fly to where you want to go, and then drive to your ultimate destination.)


You should try it

What we found once we took the plunge was that this was a wonderful way to get family time. It's definitely different and not without its own challenges, but the relaxed approach to travel, the convenience of better food, predictable accommodations, and space all make for a great experience. Though we have been fortunate to see some truly amazing destinations (and I expect both national parks this year to be equal to past trips), some of our fondest memories of these trips are from the journeys themselves. America still has some great road-side diners, and every once in a while there's a breathtaking vista that just materializes in front of you. Nothing beats pulling over and breaking out a meal to celebrate getting away from it all.

What did I miss? Anything else you want to know about the experience? I'll add to this if needed; thanks to everyone who asked for this!

Tuesday, January 29, 2013

Digital natives vs. digital tourists

I spent the weekend in Chicago as a very fortunate attendee at ORDcamp, an annual unconference that's the brainchild of +Brian Fitzpatrick and +Zach Kaplan. I've got several things I want to write about as a result of the many wonderful sessions – being surrounded by a couple hundred fascinating people is apparently what I needed to get back on the blogging horse. It's good to be back!

An early session I attended was titled "Raising digital natives"; most in the room were parents, and we kicked things off by going around the room introducing ourselves and saying a few words about what the topic meant to us. One by one, parents (most of whom had children in the 3-6 range) expressed concern about technology. (Keep in mind, this was a very technically literate group.) Statements about wanting to limit screen time, avoid television altogether, restrict video games, etc. abounded. Then it was my turn to introduce myself.

That's when I realized: I don't want to restrict any of those things for my children. I absolutely want them to find balance, they must do homework and chores first, and my wife and I rely on Common Sense Media for help gauging whether certain materials are appropriate for our kids, but the fears expressed by several in the room about the potential harm that could come from exposing their children to technology are not mine. Not at all. I started by saying that I want my kids to be hackers. I want them to be frustrated by the way information is presented to them and be motivated to learn how to change it. I want them to visualize a tool – a program, a device, whatever – and then make it.

At some point during the session, it occurred to me that what we were talking about was not a digital native in the sense I thought of a native; we were talking about a digital tourist. Natives know the lay of the land, they know all the secrets, and they know what makes their area special. Tourists rarely get below the surface – they may enjoy the place they're visiting, but they rarely know what makes it tick.

I want my kids to be natives when it comes to the technology that increasingly surrounds them. Digital tourists (I doubt this term is new or unique to me, but I don't believe I'd heard it before) will be able to use a smart phone, a computer, or some other technology, but they won't really understand them, and they definitely won't be able to change or improve them. Natives, on the other hand, will see beyond the surface, appreciate the utility these tools provide, but also see their flaws, and over time be motivated to improve them.

To be clear, I don't think this means that my kids all have to become computer scientists. They could be artists, writers, designers, or something else entirely. But I'm certain that kids who develop the skills to shape the world around them through technology (in whatever form that takes) will have a huge advantage as they grow up. Understanding that the world around them is in fact changeable is a big first step.

One parent in the room was frustrated by this, because she said she didn't understand how computers worked, so how could she help her kids understand them? I'm sure that's daunting for some – and I certainly have a huge advantage as I've been tinkering with computers for over 30 years now – but I don't think this is as hard as it seems. There's no rule that says you have to know the answer to the questions you ask. "How do you think the DVR works?" to a kid who wants to watch a show they've recorded is a good exercise to get them to think about the inner workings of a hard drive (what does it mean to record a tv show?), a video signal (how would you change the channel? where is the video coming from?), a program guide (how does TiVo know what's showing and when?), and a TV (how does the TiVo send the recording to the TV?). "How does the car's GPS work?" is a great time to talk about satellites (how does the car know where it is?), traffic data (where does it come from?), routing (how does the computer know which roads to recommend?) and data visualization (is the info presented in a way that's useful? how would you make it better?).

Whether you know the answers to those questions doesn't matter at all; it's the act of asking the question that matters. And if you want to actually find the answers to some of these questions, check out YouTube. It's great for stuff like this:


Several years ago I discovered that my oldest son (then 9) had figured out how to bypass the parental controls on one of our computers in order to play some Flash games his friends had told him about. While that led to a long conversation about responsibility, it's nevertheless exactly the kind of enthusiasm and curiosity that I want to encourage. They're not natives yet, but they're on their way. And before too long I expect they'll be telling me more about the world around us than I can tell them. I can't wait.

Monday, October 15, 2012

RIP, Michael O'Connor-Clarke



A good friend of mine died on Saturday. For those who didn’t have the opportunity to meet this man, I feel compelled to tell you a bit about him.



I first met Michael O’Connor-Clarke at the Hilton New York in 1999 when we were in marketing for competing software companies. He at Hummingbird, the industry-leading document management software company, and I at iManage, the upstart nipping at Humminbird’s heels. I remember thinking it must have annoyed him that I was invited to share the stage with him; his company, after all, had more than 70% of the market, and iManage had been none too subtle in painting their product as yesterday’s technology.



But he wasn’t annoyed. No sooner had our panel wrapped up that he invited me to lunch. We hit it off, though we lost touch as our careers went in different directions. I stumbled across his blog several years later, and got reintroduced to what a cool guy he was.



And our paths crossed once again in New York, at another conference, this time in 2005. I was with FeedBurner, and Michael was at a tech company that was complementary to what we were doing. We reconnected over another lunch, and resolved that this time we'd stay in touch. We did.


We never went more than a few months over the last seven years without some e-mail exchange, and though we didn’t see each other too often, our lunch at SXSW a couple years ago was a highlight of that conference for me. By then I was at Google and he’d returned to agency life after some time with a tech firm, and we spent a good 90 minutes comparing notes about our families, our careers, and life in general.



Michael loved his job, and loved PR. He reveled in finding the story worth telling, and anyone who spends more than a few minutes browsing some of his blog posts will see a man who even loved those who practiced bad PR. (“Loved” might not quite be the right word: adored, maybe? Enjoyed? He took a perverse delight in their ineptitude, because even in their poorly targeted e-mail blasts, their terrible turn of phrase, their poor choice in tactics, there was a story there, too. Here’s but one example of countless exchanges he and I had over the years documenting this.)



This past July 4, I was driving my family north for a long vacation weekend. Early in the drive I got a call from one of my best friends, who was calling to tell me his wife had cancer. It hit me hard, and I spent much of that six hour drive predictably thinking about what’s important. Family. Friends. Legacy. As we neared our destination, it was dinner time. Rather than try to cook in the house we’d rented after a long drive, we found a local pizza joint that was open on the holiday. While I waited for our pizza to be finished, I checked my e-mail.



I didn’t recognize the name of the sender of the latest e-mail received, but I recognized the name in the subject line: Michael O’Connor-Clarke. The sender was Michael’s boss, sending to contacts in his address book, letting his extended network know that Michael was battling esophageal cancer.

Michael died Saturday, 48 years old, leaving behind a wife and three children, and an online and offline community of thousands whose lives he touched.



Last fall he and I were e-mailing about a YouTube problem a client of his was having. I asked how his family was doing, and his reply spoke volumes about who he was:
Things here are utterly wonderful, thanks. Actually in love with my job ... Great team, fantastic clients, and we're kicking 31 flavours of arse every single day. Family growing like weeds and eating us out of house and home, but all happy, healthy and (even more important) the kids all still like each other. La vita e bella.
It seems simplistic to reflect on a friend’s passing and say that we should cherish every moment, treasure the time we get with those we love. But the story of Michael’s life is, in the end, actually rather simple: love your family, find your passion, apply that passion to making others’ lives better while you can, and know that joy isn’t hard to find if you know where to look. I liked Michael the day I met him, and over the years grew to admire that here was a man who had his priorities firmly set.



Another of Michael’s friends recounted that Eamonn Clarke posted this on Michael’s Facebook page earlier today:

Enjoy life.
Hug your loved ones tight.
Be happy that he lived.
and raise a glass to him tonight
I’m raising a glass right now. Here’s to Michael, a man whose story I’ll remember for many years to come.

Monday, October 8, 2012

A family photo server

Earlier this year I asked for suggestions on Google+ about dealing with increasingly large image collections. In our house, we have two DSLRs, four phones that take pictures, and two point and shoot cameras. The images from these are scattered across several hard drives and online backup accounts; over the past several years they've been inconsistently backed up. We have a network attached storage device that houses all images, but due to poor backup processes in the past, we have several cases of duplicate images.

Adding to the complexity, we paid Scandigital to scan years of print photos – everything from our honeymoon to our first cross-country drive to our first house. This added several thousand images to our archive – a good thing, to be sure, as we now had electronic copies of pictures we hadn't looked at in years. But the challenge of managing those images – now numbering close to 50,000 – was getting insurmountable.

I hadn't gotten around to actually implementing a solution – we had a busy summer and I wasn't convinced I really wanted to tackle this. Then my son had a school assignment last week requiring him to find a dozen pictures to share with classmates from his childhood... and actually finding pictures for him was a nightmare. After more than an hour of poking through our archive, we hadn't found more than 5 he was happy with. I was frustrated, he was annoyed, and it became clear this wasn't sustainable. It was time to dive in.

The solution I more or less settled on was what I documented this summer: dedicate one desktop computer to organizing the image catalog. This past weekend, I picked up a computer at Best Buy, and I'm already happy with the progress (though I expect it'll be months before I will feel like I'm done). Here's what I did:

The computer

Bought a Gateway desktop with a dual core Intel processor and a 1TB hard drive. Total cost? $350. (Twenty years-ago me will stare at that line for a long, long time. It's OK, me-from-the-past; computers are commodities but gas is now $5/gallon.) It features an HDMI port, so I parked the computer behind the television in our family room and plugged it into one of the TV's available HDMI connections; when I want to display photo albums easily, I can just pull them up on the TV. (Note: when I first connected the computer to the TV, the computer's display extended beyond the boundaries of the screen. This blog post helped me figure out the problem: I had to adjust the TV's settings to stop zooming in; once I did that, I was all set.)

I added a Logitech wireless keyboard to the computer so I could operate the computer from the couch; it includes an integrated trackpad, and so far I'm pretty happy with it.

The images

Copied over all of the images from the NAS drive to the PC. Installed Picasa, and let it find all of the pictures. All told, there are slightly over 50,000 images taking up 200 gigs of disk space (I think there might be more, actually, but I haven't finished confirming that everything made it over yet). Thanks to the fast processor, indexing these images took Picasa just a few minutes; last time I tried this with a laptop it took hours and didn't complete. Hardware matters!

The faces

This is where it started getting magical: after just a couple hours, Picasa had found thousands of faces across our images, and grouped them very accurately. All of a sudden, I could see photos of my six year-old daughter, from her birth to this past summer vacation. There's my twelve year-old son – at his third birthday party, on his first day of kindergarten, leaving for his first overnight Scout camp – in one place. And my ten year-old son – the day he was born, his first airplane ride, the day he learned to ride a two-wheeler. It wasn't just the kids: my wife and I are there too, as are the grandparents (including my grandparents, both of whom have died), extended family, and friends.

What's next

Like I said, I'm nowhere near done. This is a solid foundation, but I have a long way to go. Here's what I think I need to do to get this under control:

  • De-dupe the catalog. Picasa has a nice "show duplicates" feature, but since it shows both copies of the picture that's duplicated, removing the dupes while leaving one copy is a time-consuming affair. This article from Digital Inspiration looks like it'll help; according to Picasa I have more than 4,000 duplicates.
  • Confirm I have all the pictures. I haven't done a full audit of where all of the family's pictures are hiding; in my Picasa account, in my wife's, on the kids' SD cards, etc.
  • Simplify synchronization from those sources. Once I have all of the images, the next step is to ensure that going forward the new images will get included in the master Picasa collection. Crashplan on the Mac will likely satisfy this for both my wife and I; I'm looking into solutions for Android (Dropbox with its instant-upload option may be a good go-between here, though I haven't started looking at how best to do this across several devices).
  • Install VNC on the photo server. While I'm able to operate the computer from the couch, that's not the most useful way to do actual work. It's great for lean-back viewing of the pictures, but doing lots of manipulation can get tedious. I'm going to install VNC so that I can access the computer from my laptop when I'm at home, which should make it easier to do the heavy lifting when needed.
  • Turn on cloud sync. I've got a lot of unused disk space on my Google Drive account, so once I have the local catalog in a good place, I'm going to enable Picasa's cloud synchronization, which will not only give me reliable backup of all images, it'll also give me an easy way to share all of these images. For the most part that means sharing with my wife, but I'll probably also share with family who may like the ability to browse through all of our images.
PS: The assignment

Even without all of that yet-to-be-done work completed, when it came time to find pictures for my son's assignment, it took all of about 10 minutes. The combination of a fast computer, large display, reliable face-tagging, and simple interface meant that we were able to very quickly find a handful of pictures from nearly 10 years in a matter of minutes. I'm encouraged, and feel like I've got a pretty good path forward.