Difference Between Never Did It and Did It

I spent my whole Saturday designing a new homepage for this blog. Pretty proud of the result, I showed it to my wife. She couldn't stop laughing at how bad it was. Not willing to admit defeat yet, I took it to /r/design_critiques/ seeking help from this post: I've been told this looks like shit already. What can I do to un-shit it? A particular comment there (quoted below) led me to write this article:

The design is very boring and it makes you look boring as a result. In a situation like this I'd recommend to just use a good looking template: https://www.tumblr.com/theme/36149 is a good one for your needs. It's not productive at all to try and do something you're 1. not great at, and 2. not looking for work in. Hope this helps.

Is gaining knowledge by trying new things not considered productive anymore?

Before diving into that though, you're probably wondering what my awful experimental homepage looks like. I wanted it to convey a clean and succinct message but it came out more like a careless job done in 2 minutes. Here's a screenshot.

new homepage prototype

An excerpt from another comment in the same Reddit thread:

Just remember that just as you might make engineering look easy, designers make design look easy. Having Excel doesn't make me a data analyst just as having server access doesn't make someone a web designer.

Emerging from my startup experience, I learned fast to be the Jack of all trades. User experience design, customer development, product management ... I am not so naive as to think that I can just jump in and take over anything. That's not the point. The point is that having some hands-on experience opened my eyes to how wrong I was in thinking I knew what other roles actually entailed.

Take user experience design, for example. I used to think that you just use common sense, right? No, you need to understand the user, understand the system, then somehow bridge that gap between the two. Or sales. You just talk to a lot of people, right? No, sales is about understanding user demand and discovering how their needs overlap with what you can offer.

Everything looks easy from 30,000 feet up because you don't see the details. When you've never done something, you really don't know what you don't know. We don’t realize how we automatically make assumptions and over-simplify things we don’t fully understand as a coping tactic to fill in the gaps. That's a useful tactic in everyday life, as I really can't be bothered with all the details around me. But it’s not so useful when bootstrapping a business as you can easily get blindsided. Once you've done a new job or solved a problem once, you don’t guess or handwave your way around the details anymore. You become aware of what you are unaware of. That is the difference.

Anyway, I answered my own question on whether gaining knowledge by trying new things can be productive. Yes, it can. After that, you just need a bit of practice.

What is water: Avoiding a common pitfall to customer discovery

I've been doing customer discovery for a new venture that I'm investigating. That means going out there and talking to dozens of people in my target audience. The goal is to understand their needs and identify their pain points. I start the conversation with two questions: "what do you do?" and "what are the most painful parts about your work?" I learn something new every time I ask these questions. But there's a caveat to these customer interviews. For a person that has been immersed in their problems day in and day out, asking them to describe their problems is like asking a fish to describe water.

goldfish

We fell into this trap for our first product at Spokepoint. My co-founder spoke to almost a hundred target customers. Everybody said they had that problem and would pay for it when it is ready. We spent a few weeks developing a prototype to get user feedback. We made improvements. We then tried to sell it ... Nobody bought. "But if only you had these more features..." We pivoted away from that product soon afterward.

The obvious solution is to dig into the real, underlying problems that people really have versus the problems that they think they have. Unfortunately, I don't have a magical 3-step guide to read between the lines and know what people really want to say. This comes down to a matter of communication skills, experience, and hard work. We cannot solve this fundamental problem, but we did find ways to mitigate this.

One of the best methods that we had found useful, and with credits to our lean startup mentor, Spike, are a couple simple follow-up questions to screen out problems that don't really matter to people.

When people tell you they have a problem, ask them what is
their current solution and when was the last time they looked
for a better solution.

Like I don't enjoy having to think about what to make for dinner. My current solution is to make permutations of the same things. I never bothered to find a better solution because I don't really think about it anymore. It has become my water. More often than not, people will say that they haven't looked for another solution. Some even are not doing anything about it at all! Look for the itch that people are actually scratching. Don't ask people to describe water.

Moving on

When do you give up on a venture that's neither succeeding or failing? One thing that I learned from my stock trading days is to plan for the scenarios before you jump into a trade and then stick with the plan. Never make decisions in the heat of the moment. So I am sticking with my plan. I gave myself one year to try building a startup when we moved from London to Boston. The time is up and I have decided to move on.

Looking back, this is the most incredible and brutal experience that I've had so far. I am especially amazed that we got the helps that we did considering that Spokepoint is a bootstrapped company. I am very grateful for our unicorn designer+hacker Isaac Chansky, our brilliant software engineer intern Elizabeth Hagearty, and our Clojurescript/Reagent guru Tony Tam. Of course, the person that I learned the most from is my business co-founder, Dan Siegel.

Here's a screenshot of the current Spokepoint web application.

Screenshot of Spokepoint search

It has been a roller coaster year for me and the company. My co-founder will continue to soldier onward with the company. We both believe that there is something to what we're doing with Spokepoint. We just don't know how long that might take. I am moving on personally and wish him the best of luck.

I don't know exactly what I'll do next yet. I am exploring a couple directions at the moment. One lesson that I learned from this is to keep moving one baby step at a time.

My slides from Docker Boston meetup on Using Fig for Developing Microservices

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