Making Hard Decisions

As I'm going through a transition period in my life, I think of this quote about decision-making:

"The success of a decision is determined by the ability to stick with it."

Or at least, that's my paraphrased version of a much more elegant essay by Ed Batista.

I, like many people, sometimes struggle with making a decision. And the higher the stakes, the harder it becomes to choose a path forward. This line of thinking above alleviates a lot of the pressure to choose the "right" decision. In fact, it rejects the notion of a "correct choice" entirely:

"Before we make any decisionparticularly one that will be difficult to undowe're understandably anxious and focused on identifying the "best" option because of the risk of being "wrong." But a by-product of that mindset is that we overemphasize the importance of the moment of choice itself and lose sight of the importance of everything that follows."

Batista argues that it's our determination to make the "right decision" that leads us to paralysis and away from agency and ownership. Which is true; we're often waiting for something to tip the scales beyond our doubts to persuade us in either direction. This won't always happen though, sometimes it's just up to us!

However, it's not the choice, but our actions that follow our choice that is most important. The more we work towards its success after the fact, the more likely we will feel that the decision was the "correct one".

Of course, I still try to make the best choice; I don't just surrender my decision-making process to blind commitment. Batista writes more wisdom about this, but to summarize, it's our own reasoning and emotions that can help guide us to a successful decision.

Emotions serve as an evolutionary way for our body to predict the future. We associate experiences with positive and negative emotions, and when an image of that experience appears again, our learned emotional response will trigger and help us remember, or predict, the outcomes, which in turn helps us make better decisions.

"It invokes the concept of situational awareness--knowing what has gone before, what is happening now, anticipating what is coming, and then having one's cognitive engine in the right gear"

With that point in mind, I think it's important to regulate emotions too. If that emotional volume is turned up to 100, it overpowers logic and reasoning (the other half of the decision-making process) and leads to impulsive, spiraling behavior (and bad decisions). Through emotional regulation, we can reason to understand which emotions to ignore and which to pay attention to, further increasing the odds of a successful decision.

Emotions are not always accurate though. They can blind us. That's when we need to challenge what we feel and whether it to be true, again letting logic and reasoning hold weight in the decision-making process...

"Emotions can obviously mislead us and undermine the reasoning process [...] It is likely that when our emotions interfere with reasoning rather than support it, this is due to inaccurate or irrational associations made during our formative years."

It's all about balance.


So, when I face a difficult decision, whether that's walking away from a problematic relationship, switching jobs, or moving cities, I listen to what I'm feeling, challenge those feelings with logic and reasoning, then commit to whatever it is I choose, knowing success is not automatic, but worked for. Or, in a more concise way of putting it...

“When you come to a fork in the road, take it” - Yogi Berra

The HeyKiwi Experiment

In August I had a crazy idea. After months of working alone in coffee shops, I thought to myself, "I wish I could put a big sticker on my laptop that says 'say hi!'"

And so the idea was born: social stickers. After a few iterations of design choices, we landed on some cute animals with big text that literally says "Say hi!", mixed with a QR code.

heykiwi sticker linked to my account

So now if someone wants to say hi, they can scan the QR code from a distance and learn more about me, then send a message. No confrontation, no big leaps of boldness. That's it!

Who knows if this is something anyone wants. It's kind of weird blending online with in-person like this. I find it interesting, and there's only one way to find out if others will, too.

To test, I made a TikTok last week and ran a quick ad campaign.

Here are the results:

Spend: $60. 10.1K views. Only 55% made it one second into the video. Only 21% made it to 2 seconds. Then down to 12% for 3 seconds. 40 people clicked the promoted "Shop Now" link. Of those 40, there were no organic conversions.

Approaching the next video, I have to make sure I communicate the value prop in a shorter amount of time or grab attention longer so that I have enough eyeball time to make the sale.

I'm learning first-hand what "attention economy" means here...

I'm not really worried about the conversion rate of the website yet. 40 clicks isn't statistically significant, especially considering it was a cost-per-click campaign, meaning, I'm not entirely confident those clicks were legitimately interested users (or real ones). Regardless, definitely not validation or a success by any means.

So, let's see where this goes! Welcome to the world, social stickers.

How To Pick A Good Brand Name

Picking a good name for a business is tough — picking a good name with an available website domain is even more difficult! Snagging a good domain can be a complicated, expensive investment. If you don't have the cash, you'll have to get creative! Here are some guidelines to follow when deciding on a name for your business.

.com is the best

It's okay to use other domain endings, but a .com reigns supreme. It commands the respect and a presence that other domain endings cannot. It also shows to others you're a serious business — arcade.io is a school project; arcade.com is a respectable business.

It's easily pronounceable

Make sure someone can read the word. It's slightly annoying when people have to hesitate before saying the brand to you. When running Hermae, people would always pause... "it's pronounced 'her-may' right?" ... Yes! But they shouldn't have to ask. It makes conversations a lot easier when people are confident they know how to say it. Pronouncing "GIF" is a good example of how annoying it can be.

People know how to spell it when you say it

Brands grow through word of mouth. If someone can't figure out how to spell the domain when they're searching it, they won't ever get to use the product. I own zookeenee.com. This is probably a bad domain name because if, in real life, someone asks in passing "what is that you're using?" and the other says "oh it's zookeenee! it's awesome!" — the person might not be able to find it. They'll search "zuchini" "zuccini" "zukini" or other variations. They'll probably never guess "zookeenee."

Also, avoid starting with letters that can be interchanged; a C or K both can make the same sound. If your startup is named "Kars.com", people will probably start by searching Cars.com. Not what you want.

Avoid using a meaningless prefix

Be careful about prefixing your domain with another word. For example, when I was co-founder of Arcade, we went with the domain usearcade.com. If you've visited the website before and try to revisit by typing in the URL bar of your web browser, you probably won't remember the "use" part of the domain. And some web browsers that use string-matching won't recognize the domain from your history as you type "arca-". It adds friction and makes your website a little bit harder to find. Instead "arcadetokens.com" or "arcadeplatform.com" would've been better — even though we can't get arcade.com, we at least still get the autocomplete when someone types "arcade".

It has intrinsic meaning to the product

Maybe obvious, but the product should have a clear association to what your product actually does. "Muscle Milk" is a great example; milk with added proteins! Make sure your name is relevant to what you're building.

Avoid negative denotations & connotations

Before you buy a domain, look up what that word means in the dictionary. You might be surprised! I was once building a social network, and I really liked the word "Tomcats." My papa worked on designing the F-14 Tomcat and it followed these other rules well. When I looked up the word, imagine my face when the informal definition is "a sexually aggressive man; a womanizer" — not good for a social app! Next!

Also, beware of translations or hidden meanings. Glizzy.com rolls off the tongue, right? Well, it means "hot dogs" to a lot of people. If your brand has nothing to do with hot dogs, this would pose a problem. Make sure there isn't some underlying meaning to your word already.

Avoid competing with existing brands

I'd never call anything I'm building "Apple XYZ" because Apple is already well-known. Avoid competing with a company that has dominance in the brand space already. They will be incentivized to push you out of search engine results and race with you to claim domains and social handles with the name. If the name isn't being used by a large brand already, you might be able to compete here and snatch up some brand real estate. If you want to name your software business "Pressure.com" and the only other existing business is a pressure washing business in Wisconsin, you're probably good to go.

Pay attention to syllable count

Syllables are the key to a catchy domain name. Try to stay under five syllables.

Avoid difficult words and letters

Allower.com is for sale on Namecheap auctions right now for $340. Good deal for a .com like that. However, branding Allower is going to be difficult simply because it makes your mouth do weird things when you say it. Specifically the "w" with the "er" makes for an uncomfortable combination. If you plan on targeting international markets, be extra sensitive to this. If English is a second language, this is going to be a tough read.


Good luck! If you need some ideas, Namelix is a great generator.

The Friction Of Selling Hermae

June 14th marked the four month anniversary of incorporating Hermae.

So much has happened since my initial tweet back in January. I never would've predicted that this small experiment would lead to demos with Puma, Siemens, Carlsberg, Color.com, Jio, C.H. Robinson, ADT, Mercury, and so many more. Crazy!

All startups are bets. Our original bet was that an intelligent assistant trained on a company's design system would drive efficiency improvements and help design system teams improve adoption across their organization.

While this may or may not be true, the business opportunity around this bet has changed in substantial ways since January. Through our conversations with prospective customers, we've been witnessing first-hand the diminishing demand of such a product.

AI Has Changed

The landscape has evolved dramatically since January. AI has become mainstream and with that, we lost our edge of providing a new "wow" experience. The impressiveness of our demo has declined over time as people have become more familiar with the technology, and with this maturation, incumbent tools like GitHub Copilot have grown in market dominance.

Our posturing as a privacy-focused alternative has weakened as teams have become more comfortable using mainstream AI products in their workflows. Similarly, building tailored experiences like the ones we offer has also been made easier with OpenAI's Assistant API. As the accessibility to the technology improved, our defensibility weakened.

Designers Not Included

Selling to design system teams is difficult. They are notoriously under-invested and the persona of the team lead is inconsistent. Sometimes it's an engineer, sometimes it's a designer, and sometimes it's a PM who doesn't understand either. With our custom implementation approach, we'd usually need to talk to an engineer to learn more about their architecture so that we may perform the training and supply our product. If the team was led by a designer, this point would instantly fall flat and navigating these conversations would instantly stifle sales progress. At the same time, the product was not built for designers, and they would leave disappointed if they were on the call. As it turns out, if the product doesn't serve everyone on the team that's looking to buy, it won't convert to a sale.

No One-Click Solution

With the difficulty of navigating those conversations, it would be amazing if we could offer a one-click solution to teams with a self-serve model. Unfortunately, all design system documentation sources are different. Some use Storybook, some use Figma, and many build their own websites. This makes ingesting the documentation for training a tricky process that can't be fully automated. So, that leads us back to the custom experience sales process. Too much friction.


Through our sales conversations, those three points have made themselves clear as the primary blockers to continuing purchasing discussions. Those three points are unchangeable. But something has to change if Hermae is going to survive: the product or the business.

AKA, time for a pivot. That's what I'm exploring now.

EGOS Methodology For Managing Design Systems

I've met about a hundred different design system teams since starting in the industry. Through work, social outings, through Arcade selling design token management software and now through Hermae selling design system intelligence software.

Through selling, we have to start with a discovery phase, where we learn as much as we can about our potential customer. These are almost always design system teams, and even today, I'm shocked by how unique each of these teams are. Everyone has the same job titles, but each team is in a drastically different position than the next. Some are in a great position to succeed, but believe it or not, most aren't. Perhaps that's why they come to me.

After years of these discovery calls, I've noticed a few patterns that the most successful teams employ. They might not call it by the same term, but they express the same sentiments.

Below I outline a methodology derived from my learnings over the years, a methodology that I believe fosters a powerful design system team (or frontend infrastructure, frontend platform, foundations, whatever you call it...).

I present: EGOS. Efficiency, Guidance, Observability, and Synchronization. The very best teams exemplify these qualities. I believe by following these four pillars as closely as possible, any team, no matter what position they're in, can transform into a powerhouse unit within their organization.

Efficiency

A good system team remembers that their first priority is to enable organizational efficiency. They are the stewards of product craftsmanship, consistency, and speed, and they provide the tools to accomplish those goals. They avoid unnecessary complexity. They enable an organization to scale rapidly with confidence. They implement solutions and their work does not cause headaches for others.

Guidance

A good system team understands they're leaders in the organization. They implement foundational patterns and best practices to guide the rest of the team. They strive to deliver a remarkable experience for others using the system. This includes excellence in onboarding, instruction, documentation, peer-programming, supplemental material, and mentoring.

Observability

A good system team knows that their product is not perfect, and their work is never finished. They know what is being used and what is not being used. They have tools to know where and what to optimize, where the system succeeds and where the system fails. They collect data and generate reports on different metrics that define system health and performance. They quantitatively understand how their system impacts the business and organization as a whole, and understand how to use this information to improve the system.

Synchronization

A good system team knows that their work is not performed in a silo, but is a coordinated effort that supports multiple entities across an organization. They know their system will evolve over time, and it's their responsibility to keep people and output in sync with their system. They communicate regularly about system efforts and changes. Synchronization between design and engineering is a top priority, with neither outpacing the other.


Does your team follow these principles? Is there something important you think I'm missing? Let me know.

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