Get Good at Getting it Wrong

Anna Fine
Thoughts And Ideas
Published in
9 min readDec 21, 2016

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** Editors’ Pick **

Let’s be honest, 2016 was a bad year. As it comes to a close, I’ve been doing my best to try to consider all its good parts. After all, it started off with such promise.

This past February, I had the honor of speaking at Harvard for their annual design conference. I wanted to share my talk and experience sooner than December, but given the year’s close and the “new year, new me” resolutions bound to start coming up, I thought now was as good a time as any to share my findings.

Two years ago I was part of an inaugural class for a program started by Google called 30 Weeks. If you’re thinking the name sounds very “pregnancy,” you’re not wrong; we designers were tasked with 30 weeks to bring an idea/business to term. The thesis of the program was to prove that designers were capable entrepreneurs.

Oftentimes designers are seen as people who get paid to make pretty pictures. And while we all wish our jobs were as simple as that, a designer’s job, regardless of industry, is to problem-solve. A client comes to us and says “I have a business that caters to this specific target audience. We have aspirations for growth, and will need ________ to help us get there.” In this case, the blank space could be a logo, brand, product, website, campaign, or otherwise to make someone else’s business problem a design solution.

Herein lies the genesis of 30 Weeks. Google Creative Lab teamed up with Hyper Island and created a “curriculum” or timeline that would ensure design-founders’ best successes. The most intriguing part was that we were a bunch of start-up *founders* seeking advice from a start-up incubator.

With each class came new learnings, so the timeline would frequently change. By the time the most recent class was in full-swing, it was a 15-week incubator program, where only the most successful and capable were allowed to participate in the accelerator portion of the program — an additional 15 weeks.

What never changed however, was its core — an iterative curriculum designed for its participants to fail fast.

“Fail fast” is one of those hot buzzwords thrown around start-up land that basically means you throw spaghetti at the wall until something sticks. It comes from a software engineering background where a system reports any indications of future failures. In practice, it’s a business strategy for getting your idea from paper to market quickly. The spaghetti throwing is called “rapid ideation,” or coming up with rapid-fire solutions. You push in one direction until you no longer can, then pivot and push in that new direction for as long as possible.

“Pivot” is yet another buzzword in the tech world that essentially means you change gears. Rapid ideation and pivoting were my entire “fail fast” experience at 30 Weeks.

Speaking at the Harvard x Design conference.

The Harvard x Design Conference topic for 2016 was “Failure.” So when they reached out to Shana Dressler, Executive Director of 30 Weeks, they asked for the program to talk about the “Fail Fast,” iterative model employed. As I was the most prolific participant in the first class, I was asked to speak.

Since I am now a Design Director at R/GA, I think we can safely start off with the knowledge that I did not launch a successful company. In fact, I did not launch 6 companies — and with that, allow me to take you through my “failures.”

Here I’m speaking about all the disciplines I employed for the ideas I pursued.

My “Failures” at 30 Weeks

I started my presentation by introducing myself and my background. For time, if you really want to know my background, you can check it out here. But in all honesty, it doesn’t matter what I’ve done. What matters most is that I don’t like the word “no.” If someone tells me I can’t, I will find a way that I can.

So I thought my time at 30 Weeks was going to be one big challenge for me to tackle, when in reality, it was a series of challenges that I hadn’t prepared myself to overcome. Technology is a malleable industry where challenges vary in severity daily. Sleep was hard to come by, and there were moments when I had been knocked down so many times I started to doubt myself. But every time, I would get back up and keep pushing.

I pushed and comprehensively pursued 6 ideas in the given 30 weeks — the full spectrum from ideation to business models and market strategy. In order to protect my intellectual property and save time, I’ve avoided showing full products.

1) The first idea was Sizease — a way to try on clothes without putting clothes on. It would algorithmically tell you if something fit tight, loose, short, or long based on your measurements.

Sizease didn’t work out because I was late to the game. There were several companies who had about 3–4 years of research already. It was an ambitious idea. I was on the right track, but it wasn’t the right execution for me to pursue.

2) Guest Access was my solution for those awkward moments when you hand your phone to a friend or child and they see something you don’t want them to see. Like a desktop’s admin, you would access the entry passcode screen by swiping twice to then access your curated apps for guests’ viewing.

It was another ambitious idea as I would have needed Apple’s and Google’s top engineers to make my idea work the way I envisioned it. Not in a couple years, let alone 30 weeks.

3) Emotivote was a web camera technology that read a person’s facial micro-expressions to give the video’s host real-time feedback about their content. I chose not to pursue, however, because it was B2B, and I wanted to interact with consumers personally.

4) For Harry Potter nerds like myself, Wailer is basically a Howler for your phone. You would send a 6-second sound-bite to a friend, and when that friend opens their phone, it would automatically play. No matter what.

It was never going to happen because Apple prevents that kind of trolling, much to my dismay.

5) Spotter is, simply put, a luggage tracking RFID and app. This was the last idea I worked on, but it was, unfortunately, put on the back-burner for personal reasons. I hope to revisit it in future.

6) We all own a lot of stuff. The idea behind Trunk was to keep track of all of it. Trunk is a personal inventory tracker achieved at the point of purchase that provided an easy way to track down what you own. And the best time to do that is when the items are bought.

Trunk was the idea I pursued for the longest period of time, mainly because I was unable to recognize when to move on.

I had mixed reactions about this idea from friends, advisors, and potential investors. Some thought it was awesome and would take the credit industry in a much-needed direction. Others saw it fulfilling other uses for it that ultimately were against its intended value proposition. But I was determined that it was the kind of technology that would naturally progress into an API that could improve numerous other technologies.

It wasn’t until I talked with potential partners and investors while prototyping Trunk that I realized I had two major flaws with my idea.

  1. The technology lent itself to so many possibilities that the core use-case became many use-cases and the idea was subsequently watered down.
  2. The kind of product was wrong. It didn’t pass the toothbrush test — or regular usage case — because it was a need-based product. It was designed to be out of sight, out of mind, and that doesn’t encourage user engagement. User engagement is crucial for a new product.

Yet even with these flaws, I had companies in commerce, credit, and insurance industries interested in what I was doing. They all want to integrate, but the foundation is so broken that no one person, or company can do it alone. So when I approached one particular commerce company, they said to me, “We love this idea. We’ve been trying to do it ourselves, even. But it’s a lot of money and integration, and you’re not experienced enough. Go fail at something, and then get back to us.”

“Go fail at something, and then get back to us.”

So that’s what I’ve been doing. Going out — failing — and continuing to learn. I worked at a VC incubator to understand the economy of the industry and see what VC’s wanted in a start-up. I worked with a small start-up to understand the kind of people, talent and decisions needed to make it a successful business. Now I’m working at a digital agency learning the logistics of managing large groups of people. Every experience, every “failure,” is actually my success because I continue to try to build something bigger than myself.

My Learnings and Advice

Rapid ideation breaks down into two components:

  1. Recognizing a good idea, and
  2. Recognizing when to move on.

From my time at 30 Weeks and after, I learned to quickly recognize when something wasn’t working and when something needed to be pushed.

Recognizing a good idea is discovered through qualitative validation. It’s a fast way to prove whether the idea is good or needs pivoting.

I was able to come up with this list based on what I learned both from my experience in advertising, as well as the mentors and speakers from 30 Weeks. First, you need to find what some in advertising call the “truthism” or “universal truth.” In tech, it’s simply the “user need.”

What is the thing you’re solving for that other people can relate to?

Once you know your intent, start looking at direct competitors and analogous industries to get a feel for what is or isn’t working and how you can differentiate your product in your market field.

Then talk to everyone you can about the idea. No one is going to steal it — they don’t care enough to. So share and get feedback. The people you speak to are potential customers, and customers are king.

As for recognizing whether an idea was worth pursuing or abandoning, I employed a sitemap, something used to solve a product’s user experience.

This is the part where New Year resolutions come into play. I call it a “personal sitemap.”

The methodology is simple: Ask yourself, do your personal goals align with your company’s goals — or your job’s goals? — or your partner’s goals?

If you are not willing to address and overcome the pitfalls you’re aware of, let alone the ones that creep up on you, then you don’t have the passion to really make it work. Move on.

Have a “real talk” with yourself. Instead of the predictable question you get asked in interviews — where will you be in five years? — ask “what skill-sets do you want to have in five years?”

There are a few reasons for this:

  1. Skill-sets drive the job you get.
  2. Knowing what kinds of skills you want will help inform what role you should play in your company. Perhaps you’re better suited for COO rather than CEO.
  3. Knowing what skills you have and what skills you want helps determine your pitfalls. Which helps inform who you should hire.
  4. Knowing all of these things allows you to make sure it all aligns with your personal sitemap.

In Short

To fail fast, you have to validate your idea, (real) talk to yourself, and then if and when that idea fails, laugh it off and try again.

Sadly, the 30 Weeks program is no longer running. But in its time it helped create AMAZING ideas and inspired equally amazing designers to branch out beyond their normal spheres.

My grandfather used to say “nothing is so bad that it’s not good for something,” and I think he’s right. 2016 was a bad year, but I hope we can all take our learnings and fail better next year.

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Anna Fine
Thoughts And Ideas

Freelance Design Director, currently @ Instacart, formerly instructor @ SVA; worked @ Policygenius, Droga5, R/GA, Google Creative Lab's 30Weeks, Anomaly