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Tuesday, December 31, 2013

2013: The Constant Introspection of Management

I've been a serious manager for a little over a year now, and it has been my biggest challenge of 2013. Previously I had managed small teams but looking back, while I thought that would prepare me to lead multiple teams and manage managers myself, in reality nothing could be further from the truth.

The hardest part for me of going from individual contributor/architect/tech lead to managing in anger has been the lack of certainty. I believe that, for experienced managers, management can have a level of rigor and certainty, but I'm not there yet. I am striving to be a compassionate manager and that requires developing a level of emotional intelligence that I have never before needed. And so as a result I would have to say that the past year has probably been one of the most emotionally draining of my life (and that is not even counting the baby I had in the middle of it).

I do not want to be a dispassionate leader who views people like pawns on a chessboard. But the emotional resilience that is required for management makes me understand how folks with that tendency may find it easier. A successful manager needs to care about her people without taking the things they do personally. Every person who quits feels like an indictment of all the ways you failed them. If only I had given better projects, fought harder for their salary, coached them better, done more to make them successful! If you wonder why it seems sometimes that management roles get taken up by sociopaths, just think that for every interaction you have with a difficult coworker, your manager has probably had to deal with ten of them. It's not a surprise that a certain bloody-mindedness develops, or, more likely, survives.

In addition to the general emotional angst of all those people, there's the general feeling of utter incompetence. As an engineer, I know how to design successful systems. I can look back on a career of successful projects, and I know many of the best practices for building systems and writing code. Right now, if I were to design a system that ultimately failed for a technical reason, I would be able to pinpoint where the mistakes were made. I am a beginner all over again when it comes to the big-league management game, and it's discouraging. I miss doing what I'm good at, building systems, and I'm afraid that I've given it up for something I may never do particularly well.

One of my friends who has faced the same struggle put it best. 
I like the autonomy/mastery/purpose model of drive. This feels like an issue with mastery. Not building means moving away from something where you have mastery to something new. There’s fear of losing mastery.[1]
As a new manager I believe you lose both autonomy and mastery for a time being, and arguably autonomy is lost forever. You are always only as good as your team, and while some decisions may ultimately rest on your shoulders, when you choose to take the "servant leadership" path you do sacrifice a great deal of autonomy. But I think for many engineers the loss of mastery hits hardest. When you've spent ten plus years getting really, really good at designing and developing systems, and you leave that to think about people all day? It's hard, and no, there isn't always time for side projects to fill the gap. In an industry that doesn't always respect the skills of management, this is a tough pill to swallow. After all, I can become the greatest manager in the world, but if I wanted to work in that role at Google they would still give me highly technical interviews.

So why do it? In the end, it has to be about a sense of purpose. I want to have a bigger impact than I will ever be able to have as an architect or developer. I know that leading teams and setting business direction is the way to ultimately scratch the itch I have for big impact, for really making a lasting difference. And I know that a great manager can have a positive impact on many, many people. So here's to growing some management mastery, and making 2014 a year of purpose and impact.

Wednesday, July 31, 2013

Replatforming? The Proof is in the Hackday

It's pretty common for teams, especially startups, to get to a point with their tech stack where the platform they've been working on just isn't cutting it anymore. Maybe it won't scale, maybe it won't scale to the increased development staff, maybe it was all written so poorly you want to burn it to the ground and start fresh. And so the team takes on the heroic effort we know and love: replatforming.

When you're replatforming because the current system can't handle the necessary load, it's pretty easy to see if your effort was successful. Load test, or simply let your current traffic hit it and watch it hum along where you once were serving 10% failures. But if the replatforming is done to help development scaling, how do you know the effort was a success?

I accidentally discovered one answer to this question today. You see, Rent the Runway has been replatforming our systems for almost the last two years. We've moved from a massive, and massively complex Drupal system to a set of Java services fronted by a Ruby thin client. Part of the reason for this was load, although we arguably could've made Drupal handle the load better by modernizing certain aspects of our usage. But a major reason for the replatforming was that we simply weren't able to develop code quickly and cleanly, and the more developers we added the worse this got. We wanted to burn the whole thing to the ground and start fresh.

We didn't do this, of course. We were running a successful business on that old hideous platform. So we started, piece by piece, to hollow out the old Drupal and make it call Java services. Then, with the launch of Our Runway, we began to create our new client layer in Ruby using Sinatra. Soon we moved major pages of our site to be served by Ruby with Java on the backend. Finally, in early July, we moved our entire checkout logic into Java, at which point Drupal is serving only a handful of pages and very little business logic. 

So yesterday we had a hackday, our first since the replatforming. We do periodic hackdays although we rarely push the entire team to participate, and yesterday's hackday was one of the rarer full-team hackdays. Twenty-some tech team members and four analytics engineers participated, with demos this morning. I was blown away with what was accomplished. One project by a team of four enabled people to create virtual events based on hashtags and rent items to those events, pulling in data from other social media sources and providing incentives to the attendees to rent by giving them credits or other goodies as more people rented with that hashtag. This touched everything from reservations to checkout. We had several projects done by solo developers that fixed major nasty outstanding issues with our customer service apps, and some very nice data visualizations for both our funnel and our warehouse. All told we had over ten projects that I would like to see in production, whether added to existing features, as new features, or simply in the data dashboard displayed in our office. 

Compare this to the last full-team hack day and the differences are striking. That hack day had very few fully functional projects. Many were simulations of what we could do if we could access certain data or actions. Most didn't work, and only a handful were truly something we could productionize. The team didn't work any less hard, nor was it any less smart than it is now. The major difference between that hack day and now is that we've replatformed our system. Now adding new pages to the site is simple and doesn't require full knowledge of all the legacy Drupal. Getting at data and actions is a matter of understanding our service APIs, or possibly writing a new endpoint. Even our analytics data quality is better. 

So if you're wondering whether your replatforming has really made a difference in your development velocity, try running a hackday and seeing what comes out. You may be surprised what you learn, and you'll almost certainly be impressed with what your team can accomplish when given creative freedom and a platform that doesn't resist every attempt at creativity.

Monday, May 20, 2013

ZooKeeper and the Distributed Operating System

From the draft folder, this sat moldering for a few months. Since I think the topic of "distributed coordination as a library/OS fundamental" has flared up a bit in recent conversations, I present this without further editing.

I'm preparing to give a talk at Ricon East about ZooKeeper, and have been thinking a lot of what to cover in this talk. The conference is focused on distributed systems at a somewhat advanced level, so I'm thinking about topics that expand beyond the basics of "what is ZooKeeper" and "how do you use it." After polling twitter and getting some great feedback I've decided to focus on the question that many architects face: When should I use ZooKeeper, and when is it overkill?

This topic is interesting to me in many ways. In my current job as VP of Architecture at Rent the Runway, we do not yet use ZooKeeper. There are things that we could use it for, but in our world most of the distributed computing we do is pure horizontally scalable web services. We're not yet building out complex networks of servers with different roles that need to be centrally configured, managed, or monitored beyond what you can easily do with simple load balancers and nagios. And many of the questions I answer on the ZooKeeper mailing list are those that start with "can ZK do this?" The answer that I prefer to give is almost always "yes, but keep these things in mind before you roll it out for this purpose." So that is what I want to dig into more in my talk.

I've been digging into a lot of the details of ZAB, Paxos, and distributed coordination in general as part of the talk prep, and hit on an interesting thought: What is the role of ZooKeeper in the world of distributed computing? You can see a very clear breakdown right now in major distributed systems out there. There are those that are full platforms for certain types of distributed computing: the Hadoop ecosystem, Storm, Solr, Kafka, that all use ZooKeeper as a service to provide key points of correctness and coordination that must have higher transactional guarantees than these systems want to build intrinsically into their own key logic. Then there are the systems, mostly distributed databases, that implement their own coordination logic: MongoDB, Riak, Cassandra, to name a few. This coordination logic often makes different compromises than a true independent Paxos/ZAB implementation would make; for an interesting conversation check out a Cassandra ticket on the topic.

In thinking about why you would want to use a standard service-type system vs implementing your own internal logic, it reminds me very much of the difference between modern SQL databases and the rest of the application world. The best RDBMSs are highly tuned beasts. They cut out the middleman as much as possible, taking over functionality from the OS and filesystem as it suits them to get absolutely the best performance for their workload. This makes sense. The competitive edge to the product they are selling is its performance under a very well-defined standard of operation (SQL with ACID guarantees), as well as ease of operation. And in the new world of distributed databases, owning exactly the logic for distributed coordination (and understanding where that logic falls apart in the specific use cases for that system) will very likely be a competitive edge for a distributed database looking to gain a larger customer base. After all, installing and administering one type of thing (the database itself) is by definition simpler than installing and administering 2 things (the database plus something like ZooKeeper). It makes sense to prefer to burn your own developer dollars to engineer around the edge cases, so as to make a simpler product for your customers.

But ignoring the highly tuned commercial case of distributed databases, I think that ZooKeeper, or a service like it, is a necessary core component of the "operating system" for distributed computing. It does not make sense for most systems to implement their own distributed coordination, any more than it makes sense to implement your own file system to run your RESTful web app. Remember, to do distributed coordination successfully requires more than just, say, a client library that perfectly implements Paxos. Even with such a library, you would need to design your application up-front to think about high availability. You need to deploy it from the beginning with enough servers to make a sane quorum. You need to think about how the rest of the functioning of your application (say, garbage collection, startup/shutdown conditions, misbehavior) will affect the functioning of your coordination layer. And for most of us, it doesn't make sense to do that up-front. Even the developers at Google didn't always think in such terms, the original Chubby paper from 2006 mentions most of these reasons as driving the decision to create a service rather than a client library.

Love it or hate it, ZooKeeper or a service like it is probably going to be a core component of most complex distributed system deployments for the foreseeable future. Which is all the more reason to get involved and help us make it better.

Friday, February 8, 2013

Branching Is Easy. So? Git-flow Is Not Agile.

I've had roughly the same conversation four times now. It starts with the question of our deployment/development strategy, and some way in which it could be tweaked. Inevitably, someone will bring up the well-known git branching model blog post. They ask, why not use this git-flow workflow? It's very well laid out, and relatively easy to understand. Git makes branching easy, after all. The original blog post in fact contends that because branching and merging is extremely cheap and simple, it should be embraced.
As a consequence of its simplicity and repetitive nature, branching and merging are no longer something to be afraid of. Version control tools are supposed to assist in branching/merging more than anything else.
But here's the thing: There are reasons beyond tool support that would lead one to want to encourage or discourage branching and merging, and mere tool support is not reason enough to embrace a branch-driven workflow.

Let's take a moment to remember the history of git. It was developed by Linus Torvalds for use on the Linux project. He wanted something that was very fast to apply patches, and supported the kind of distributed workflow that you really need if you are supporting a huge distributed team. And he made something very, very, very fast, great for branching and distributed work, and difficult to corrupt.

As a result git has many virtues that align perfectly with the needs of a large distributed team. Such a team has potentially long cycles between an idea being discussed, being developed, being reviewed, and being adopted. Easy and fast branching means that I can go off and work on my feature for a few weeks, pulling from master all the while, without having a huge headache when it comes to finally merge that branch back into the core code base. In my work in ZooKeeper, I often wish I bothered to keep a git-svn sync going because reviewing patches is tedious and slow in svn. Git was made to solve my version control problems as an open source software provider.

But at my day job, things are different. I use git because a) git is FAST and b) Github. Fast makes so much of a difference that I'm willing to use a tool with a tortured command line syntax and some inherent complexity. Github just makes my life easier, I like the interface, and even through production outages I still enjoy using it. But branching is another story. My team is not a distributed team. We all sit in the same office, working on shared repositories. If you need a code review you can tap the shoulder of the person next to you and get one in 5 minutes. We release frequently; I'm trying to move us into a continuous delivery model that may eventually become continuous deployment if we can get the automation in place. And it is for all of these reasons that I do not want to encourage branching or have it as a major part of my workflow.

Feature branching can cause a lot of problems. A developer working on a branch is working alone. They might be frequently pulling in from master, but if everyone is working on their own feature branch, merge conflicts can still hit hard. Maybe they have set things up so that an automated build will still run through every push they make to that branch, but it's just as likely that tests are only being run locally and the minute this goes into master you'll see random failures due to the various gremlins of all software development. Worst of all, it's easy for them to work in the dark, shielded from the eyes of other developers. The burden of doing the right thing is entirely on the developer and good developers are lazy (or busy, or both). It's too easy to let things go for too long without code review, without integration, and without detecting small problems. From a workflow perspective, I want something that makes small problems come to light very early and obviously to the whole team, enabling inherent communication. Branching doesn't fit this bill.

Feature branching also encourages thinking about code and features as all or none. That makes sense when you are delivering a packaged, versioned product that others will have to download and install (say, Linux, or ZooKeeper, or maybe your iOS app). But if you are deploying code to a website, there is no need to think of the code in this binary way. It's reasonable to release code behind feature flags that is not complete but flagged off, for purposes of keeping the integration of that new code in for testing in other environments. Learning how to write code in such a way as to be chunkable, flaggable, and almost always safe to go into production is a necessary skill set for frequent releases of any sort, and it's essential if you ever want to reach continuous deployment.

Release branching may still be a necessary part of your workflow, as it is in some of our systems, but even the release branching parts of the git-flow process seems a bit overly complex. I don't see the point in having a develop branch, nor do I see why you would care about keeping master pristine, since you can tag the points in the master timeline where you cut the release branch. (As an aside, the fact that the original post refers to "nightly builds" as the purpose of the develop branch should raise the eyebrows of anyone doing continuous integration.)  If you're not doing full continuous deployment you need to have some sort of branch that indicates where you cut the code for testing and release, and hotfixes may need to go into up to two places, that release branch and master, but git-flow doesn't solve the problem of pushing fixes to multiple places. So why not just have master and release branches? You can keep your release branches around for as long as you need them to get live fixes out, and even longer for historical records if you so desire.

Git is great for branching. So what? Just because a tool offers a feature, and does it well, does not mean that feature is actually important for your team. Building a whole workflow around a feature just because you can is rarely a good idea. Use the workflow that your team needs, don't cargo cult an important element of your development process.

Sunday, December 30, 2012

Make it Easy

One of my overriding principles is: make it easy for people to do the right thing.

This seems like it should be a no-brainer, but it was not always obvious to me. Early in my career I was a bit of a self-appointed build cop. The team I worked on was an adopter of some of the agile/extreme programming principles, and the result of that was a 40+ person team all working against the same code base, which was deployed weekly for 3 distinct business purposes. All development was done against trunk, using feature flags. We managed to do this through the heavy use of automated unit/integration testing; to check code in, you were expected to write tests of course, and to run the entire test suite to successful completion before checking in.

Unsurprisingly, people did this only to a certain level of compliance. It drove me crazy when people broke the build, especially in a way that indicated they had not bothered to run tests before they checked in. So I became the person that would nag them about it, call them out for breaking things, and generally intimidate my way into good behavior. Needless to say, that only worked so well. People were not malicious, but the tests took a LONG time to run (upwards of 4 hours at the worst), and on the older desktops you couldn't even get much work done while the test suite ran. In the 4 hours that someone was running tests another person might have checked in a conflicting change that caused errors; was the first person really supposed to re-merge and run tests for another 4 hours to make sure things were clean? It was an unsustainable situation. All my intimidation and bullying wasn't going to cause perfect compliance.

Even ignoring people breaking the build, this was an issue we needed to tackle. And so we did, taking several months improve the overall runtime and make things easier. We teased out test suites into specific ones for the distinct business purposes combined with a core test suite. We made it so that developers could run the build on distributed hardware from their local machine. We figured out how to run certain tests in parallel, and moved database-dependent tests into in-memory databases. The test run time went way down, and even better, folks could kick off the tests remotely and continue to work on their machine, so there was much less reason to try and sneak in an untested change. And lo and behold, compliance went way up. All the sudden my build cop duties were rarely required, and the whole team was more likely to take on that job rather than leaving it to me.

Make it easy goes up and down the stack, far beyond process improvements. I occasionally find myself at odds with folks that see the purity of implementing certain standards and ignore the fact that those standards, taken to extreme, make it harder for people to do the right thing. One example is REST standards. You can use the http verbs to modify the meanings of your endpoints and make them do different things, and from a computer-brain perspective, this is totally reasonable. But this can be very bad when you must add the human brain perspective to the mix. Recently an engineer proposed that we change some endpoints from being called /sysinfo (which would return OK or DEAD depending on whether a service was accepting requests), and /drain (which would switch the /sysinfo endpoint to always return DEAD), into one endpoint. That endpoint would be /sys/drain. When called with GET, it would return OK or DEAD. When called with PUT, it would act as the old drain.

To me, this is a great example of making something hard. I don't see the http verb, I see the name of the endpoint, and I see the potential for human error. If I'm looking for the status-giving endpoint, I would never guess that it would be the one called "drain", and I would certainly not risk trying to call it to find out. Even knowing what it does, I see myself accidentally calling the endpoint with GET, now I didn't drain my service before restarting it. Or I accidentally called it with PUT and now it's been taken out of the load balancer. To a computer brain, GET and PUT are very different, and hard to screw up, but when I'm typing a curl or using postman to call an endpoint, it's very easy for me as a human to make a mistake. In this case, we're not making it easy for people using the endpoints to do the right thing, we're making it easy for them to be confused, or worse, to act in error. And to what benefit? REST purity? Any quest for purity that ignores human readability does so at its peril.

All this doesn't mean I want to give everyone safety scissors. I generally prefer to use frameworks that force me and my team to do more implementation work rather than making it trivially easy. I want to make the "easy" path the one that forces folks to understand the implementation to a certain level of depth, and encourages using only the tools necessary for the job. This makes better developers of my whole team, and makes debugging production problems more science than magic, not to mention the advantage it gives you when designing for scale and general future-proofing.

Many great engineers are tripped up by human nature, when there's really no need to be. Look at your critical human-involving processes and think: am I making it easy for people to do the right thing here? Can I make it even easier? It might take more work up front on your part, or even more verbosity in your code, but it's worth it in the long run.

Thursday, December 20, 2012

Building a Global, Highly Available Service Discovery Infrastructure with ZooKeeper

This is the written version of a presentation I made at the ZooKeeper Users Meetup at Strata/Hadoop World in October, 2012 (slides available here). This writeup expects some knowledge of ZooKeeper.

The Problem:
Create a "dynamic discovery" service for a global company. This allows servers to be found by clients until they are shut down, remove their advertisement, or lose their network connectivity, at which point they are automatically de-registered and can no longer be discovered by clients. ZooKeeper ephemeral nodes are used to hold these service advertisements, because they will automatically be removed when the ZooKeeper client that made the node is closed or stops responding.

This service should be available globally, with expected "service advertisers" (servers advertising their availability, aka, writers) able to scale to the thousands, and "service clients" (servers looking for available services, aka, readers) able to scale to the tens of thousands. Both readers and writers may exist in any of three global regions: New York, London, or Asia. Each region has two datacenters with a fat pipe between them, and each region is connected to each other region, but these connections are much slower and less tolerant for piping large quantities of data.

This service should be able to withstand the loss of any one entire data center.

As creators of the infrastructure, we control the client that connects to this service. While this client wraps the ZooKeeper client, it does not have to support all of the ZooKeeper functionality.

Implications and Discoveries:
ZooKeeper requires a majority (n/2 + 1) of servers to be available and able to communicate with each other in order to form a quorum, and thus you cannot split a quorum across two data centers and guarantee that the quorum will be available with the loss of any one data center (because at least one data center will fail to have a pure majority of servers). To sustain the loss of a datacenter therefore you must split your cluster across 3 data centers.

Write speed dramatically decreases when the quorum must wait for votes to travel over the WAN. We also want to limit the number of heartbeats that must travel across the WAN. This means that both a ZooKeeper cluster with nodes spread across the globe is undesirable (due to write speed), and a ZooKeeper cluster with members only in one region is also undesirable (because writing clients outside of that region would have to continue to heartbeat over the WAN). Even if we decided to have a cluster in only one region, we would have to solve the problem that no region has more than 2 data centers, and we need 3 data centers to handle the loss/network partition of an entire data center.

Solution:
Create 3 regional clusters to support discovery for each region. Each cluster has N-1 nodes split across the 2 local data centers, with the final node in the nearest remote data center.

By splitting the nodes this way, we guarantee that there is always availability if any one data center is lost or partitioned from the rest of the data centers. We also minimize the affects of the WAN on write speed by ensuring that the remote quorum member is never made into the leader node, and the general effect of the majority of nodes being local means that voting can complete (thus allowing writes to finish) without waiting for the vote from the WAN node in normal operating conditions.

3 Separate Global Clusters, One Global Service:
Having 3 separate global clusters works well for infrastructural reasons mentioned above, but it has the potential to be a headache for the users of the service. They want to be able to easily advertise their availability, and discover available servers preferably by those servers available first in their local region, and secondly in other remote regions if no local servers are available.

To do this, we wrapped our ZooKeeper client in such a way as to support the following paradigm:
Advertise Locally
Lookup Globally

Operations requiring a continuous connection to the ZooKeeper, such as advertise (which writes an ephemeral node) or watch are only allowed on the local discovery cluster. Using a virtual IP address we automatically route connections to the discovery service address of the local ZooKeeper cluster and write our ephemeral node advertisement here.

Lookups do not require a continuous connection to the ZooKeeper, and so we can support global lookups. Using the same virtual IP address we can connect to the local cluster to find local servers, and failing that use a deterministic fallback to remote ZooKeeper clusters to discover remote servers. The wrapped ZooKeeper client will automatically close its connection to the remote clusters after a period of client inactivity, so as to limit WAN heartbeat activity.

Lessons learned:
ZooKeeper as a Service (a shared ZooKeeper cluster maintained by a centralized infrastructure team to support many different clients) is a risky proposition. It is easy for a misbehaving client to take down an entire cluster by flooding it with requests or making too many connections and without a working hard quota enforcement system clients can easily push too much data into ZooKeeper. Since ZooKeeper keeps all of its nodes in memory, a client writing huge numbers of nodes with a lot of data in each can cause ZooKeeper to garbage collect or run out of memory, bringing down the entire cluster.

ZooKeeper has a few hard limits. Memory is a well-known limit, but another limit is the number of sockets for a server process (configured via the ulimit in *nix). If a node runs out of sockets due to too many client connections, it will basically cease to function without necessarily crashing. This is not surprising for anyone that has experienced this problem in other Java servers, but it is worth noting when scaling your cluster.

Folks using ZooKeeper to do this sort of dynamic discovery platform should note that if the services you are advertising are Java services, a long full GC pause can cause their session to the ZooKeeper cluster to time out and thus their advertisement will be deleted. This is generally probably a good thing, because a server that is doing a long-running full GC won't respond to client requests to connect, but it can be surprising if you are not expecting it.

Finally, I often get the question of how to set the heartbeats, timeouts, etc, to optimize a ZooKeeper cluster, and the answer is really that it depends on your network. I really recommend playing with Patrick Hunt's zk-smoketest in your data centers to figure out sensible limits for your cluster.

Sunday, November 18, 2012

On Fit and Emotional Problem Solving

One of the biggest challenges Rent the Runway has is the challenge of getting women comfortable with the idea of renting. That means a lot of things. There's questions of timing, questions of quality. But the biggest question by far is the question of fit. Our business model, if you are unfamiliar, is that you order a dress typically for a 4 day rental period, which means that the dress comes very close to the date of your event, possibly even the day of that event. If it does not fit, or you don't like the way it looks on you, you may not have time to get something else for the occasion. As a woman, this uncertainty can be terrifying. Getting an unfamiliar item of clothing, even in 2 sizes, right before an event important enough to merit wearing something fancy and new is enough to rattle the nerves of even the least fussy women out there. This keeps many women from trying us at all, and presents a major business obstacle.

Given this obstacle, how would you proceed? When I describe my job to fellow (usually male) engineers, and give them this problem in particular, their first instinct is always to jump to a "fit algorithm". I've heard many different takes on how to do 3D modeling, take measurements, use computer vision techniques on photographs in order to perfect an algorithm that will tell you what fits and what doesn't.

Sites have been trying to create "fit algorithms" and virtual fit models for years now, and none has really gained much traction. Check this blog post from 2011, about that year being the year of the  "Virtual Fit Assistant". Have you heard of these companies? Maybe, but have you or anyone you know actually USED them?

I would guess that the answer is no. I know that for myself, I find the virtual fit model incredibly off-putting. I trust the fit even less seeing it stretched over that smooth polygon sim that is supposed to be like me. Where are the lumps going to be? Is it really going to fit across my broad shoulders? The current state of 3D technology looks ugly and fake and I'm more likely to gamble on ordering something from a site with nothing but a few measurements or a model picture than one where I can make this fake demo. The demo doesn't sell me, and worse, it undermines my fit confidence, because it doesn't look enough like me or any real person and it makes me wonder how those failures in capturing detail will translate into failures in recommending fit.

I've come to realize in my time at this job that what engineers often forget when faced with a problem is the emotional element of that problem. Fit seems like an algorithmic problem, but for many women, there is a huge emotional component to trying things on. The feel of the fabric. The thrill of something that fits perfectly. The considerations and adjustments for things that don't. Turning fit into a cheesy 3D model strips all emotion from the experience, and puts it into the uncanny valley of not-quite-realness. I do think that someday technology will be able to get through the valley and provide beautiful, aspirational 3D models with which to try on clothes, but we aren't there yet. So what can we do?

At Rent the Runway, we've discovered through data that when you can't try something on, photos of real women in a dress are the next best thing. Don't forget that the human brain is still much more powerful than computers at visual tasks, and it is much easier for us to imagine ourselves in an item of clothing when we see it on many other women. This also triggers the emotional response much more than a computer-generated image. Real women rent our dresses for major, fun, events. They are usually smiling, posing with friends or significant others, looking happy and radiant, and that emotion rubs off on the viewer. It's not the same as trying something on in a dressing room, but it is like seeing a dress on your girlfriend and predicting that the same thing would look fabulous on you.

This insight led us to launch a major new subsite for Rent the Runway called Our Runway. This is a view of our inventory that allows women to shop by photos of other women wearing our dresses. It is driven by data but the selling point is emotional interaction. Learning to use emotional reasoning was a revelation to me, and it might be the most valuable engineering insight I've picked up in the last year.