First Iterations Always Suck

And that’s okay…

In fact, that’s the way it should be.

There’s so much involved in designing a product. As the design lead on a project, you’re responsible for:

  • The need to understand who’s using your product
  • The need to understand what users are trying to do.
  • The need to understand what scenarios the UI will handle
  • The concept brainstorming stage
  • the concept fleshing out stage
  • interactive prototyping
  • Feedback throughout the design process
  • The front-end code
  • The back-end code
  • The speed of the app
  • The layout
  • Responsiveness
  • The copy
  • Typography
  • Colors
  • The page hierarchy
  • The interactions
  • White space
  • Motion
  • Personality to convey
  • A story to tell
  • Feedback states
  • Error states
  • Accessibility
  • Small delightful details
  • Internationalization
  • Retina considerations
  • Considerations for decisions vs. options
  • Browser testing
  • Device testing
  • The brand to consider

All of this is on your shoulders, and there’s simply no way to get all of it right with your first pass at a design.

Consistently great product design must be crafted through a process

This process will vary from designer to designer, and will likely change for you over time. Here’s the process I tend to follow these days:

  1. Gather data (who is this for, what are they trying to do, what scenarios should be considered)
  2. Based on the data, I sketch out lot’s of rough low fidelity concepts
  3. I’ll spend some time stewing on these concepts
  4. I’ll then select one concept (the one that best fits all of the criteria outlined in step 1), and flesh it out in more detail (usually in Balsamiq at this stage)
  5. I’ll solicit feedback
  6. Build out a rough interactive prototype (usually coded by hand)
  7. I’ll get feedback
  8. Code it up right and add polish
  9. Get feedback, make tweaks – repeat this step until everything is just right
  10. If the feature is in-depth, or if I still have unresolved questions, I’ll do a round of beta testing prior to launch

Myth #1: as you get better at design, you can skip some steps

Great product designers do not skip steps just to save time. If I can offer one piece of advice, it’s this: rather than seeing process as a burden, or as some form of training wheels, learn to embrace it, and see it as a valuable asset.

Myth #2: the sooner you can get to a hi-fidelity design, the better

Great product designers do not jump to high fidelity designs sooner than is necessary. In fact, they tend to delay it as long as possible. Great product designers recognize the benefits of lo-fi designs, and leverage those benefits extensively.

Up until around step eight (near the end of your process) it’s perfectly fine for your designs to still look unfinished. The longer you can stick with lo-fidelity the better. There are a couple of reasons:

  • Lo-fi concepts take less time to create
  • Since they take less time, you can create more of them, giving you more options to choose from
  • It’s easier to scrap a design that is lo-fi and start over
  • It’s easier to iterate on lo-fi designs
  • It’s easier to solicit candid feedback when people don’t think you’ve spent as much time on the concept

Early on, all UI’s suck, and it turns out, that’s the way it should be. If you outright skip steps in your design process, or if you hop straight to hi-fi mockups, your designs will tend to suffer as a result. Great UI designs follow a process, they take time to craft, and early on, even great user interfaces are going to suck.

Note: inspiration for the title of this post came from Ed Catmull in Creativity Inc. said “Early on, all movies suck”, speaking candidly about the state of early movie concepts at Pixar.


I don’t do comments on this site, but if you have thoughts, I’d love to hear them. You can email me at

Always Work on Side Projects

Finding your motivation

Side projects fall in the same category as eating well, and excerise. We all know that these activities are good for us, but it can sometimes be hard to motivate ourselves to do them.

There are lot’s of great reasons to work on side projects:

  • Because you enjoy the process of building things
  • To solve a pain that you personally have
  • To get better at your craft
  • To build your portfolio
  • To solve a pain that other people have
  • To make some cash on the side
  • To build something that may turn into your full-time employment

It’s almost guaranteed that by working on side projects, that you’ll reap more than one of these benefits.

Finding time for side projects?

The big question people always have is, “where will I find the time”? Here are a few suggestions:

  • As an experiment, try waking up 2 hours earlier than you usually do. Do this for a week. You may be amazed at how much you can get done in those early morning hours.
  • Work two extra hours late at night before going to sleep
  • Replace T.V, or Internet time with side project time
  • Knock out an hours worth of work during your lunch break

“I don’t have time” is an excuse. We all have time. It just comes down to how we prioritize it.

What can you accomplish with a side project?

Let’s say you worked on a side project 2 hours every weekday, and took the weekends off. How much could you accomplish?

Well, that’s:

  • 10 hrs in one week
  • 520 hrs in a year (or a total of thirteen 40 hr work weeks)
  • 2600 hrs in 5 years (or a total of sixty five 40 hr work weeks!) That’s over a years worth of work!

That’s insane. If you were able to commit to building side projects just 2 hours per day for 5 years, what could you accomplish?

I bet you could change your world… I’m not kidding.

Now go and do it. 🙂


I don’t do comments on this site, but if you have thoughts, I’d love to hear them. You can email me at

Start Each Design from Scratch

Let’s say you’ve done a little research, you sit down at your computer, and you’re ready to start a new design.

What’s the first thing you do?

Well… If you’re like a lot designers you immediately head over to Dribbble or some other site for inspiration.

Trust me, you don’t want outside inspiration at this stage

It sounds counter-intuitive, but the trouble with starting a design by looking for inspiration is that you’re likely to find an idea that feels like a good fit.

Once you have an idea that appears to check all of the boxes, it’s too easy to fall in love and become seduced by it. This is just human nature.

In truth, your idea will almost always appear in that moment to have all of the right ingredients. You may actually feel quite proud of yourself for being able to come up with the idea so quickly.

But what are the odds of this being the best possible solution for your users?

Experience has shown me that despite your confidence in the moment, the odds of this first idea being the best solution are actually quite low.

I’m as guilty as anyone

My plate is always full. I’m always eager to wrap “this thing” up, so that I can quickly move on to “that thing”. But in doing so, how often do I head down a less-optimal path?

The solution: At the beginning of each new design, spend 15 minutes sketching out every idea that comes to you.

A couple of years ago, I attended a day-long workshop by Brandon Schauer from Adaptive Path on sketching and rapid ideation. It was excellent.

One of the points he made really stuck with me.

We were given a verbal summary of an interface that needed to be designed. We were then instructed to sketch out a solution (these were super quick, low fidelity sketches). After we were done, we were asked to raise our hands if we liked the direction our sketches were headed. Naturally, the majority of people were really happy with their sketches.

Next, we were asked to make 6 boxes on a blank piece of paper, and to brainstorm alternate approaches. We were given a total of 15 min to complete all 6.

At the end of the 15 min, he asked everyone to rate their favorite sketch, be it the original, or one of the six new sketches. He then went through and asked us to raise our hands for each set. The revelation came when only about 5% of the audience raised their hand for the original sketch. 95% of us preferred one of our alternate approaches. This blew my mind.

“I don’t buy it…”

You may look at this experience and be suspect of the conclusion that I’ve come to. You might suppose that without doing any sort of 15-min-6-box activity, that you might have just as well arrived at the same final design through the process of iteration.

You may be right, some of the time… But how will you ever really know when you’re right, or when some unexplored path would lead to a better solution?

Is it possible that your pride is just getting in the way? I hope not. And to that end, I hope you will at least give it a try.

It’s about giving yourself more paths to choose from

That’s ultimately what it boils down to. Instead of starting with a single option, you start with half a dozen or more. Starting with multiple options will give you better odds of actually heading down the right path from the very beginning.


I don’t do comments on this site, but if you have thoughts, I’d love to hear them. You can email me at

Reduce Time to Clarity

Time to clarity is the amount of time it takes you to establish a clear/confident picture in your mind of how to go about designing the best possible solution for your users.

What activities can lead to clarity?

  1. Using a clear design process.
  2. Digging into analytics to try and discover existing insights.
  3. Chatting with happiness/support folks to help determine what the most common complaints, and user pains are.
  4. Asking other designers for feedback.
  5. Asking your partner/spouse/relative/friend to try out your interactive prototype while you watch.
  6. Doing some quick usability tests.
  7. Approaching strangers to help you out for 5 min in exchange for a $10 Starbucks gift card.
  8. Pinging people in your company that have never seen whatever it is that you’re building, and requesting 5 minutes of their time where you watch them as they talk you through your design.
  9. Running a user report in MixPanel (or whatever app you use to track users) to get a list of actual users you might email and request that they give feedback on a design for you.
  10. Running an A/B test on your design (assuming you have the traffic to support a test) to make sure that your design isn’t sinking the ship.

This is not by any means an exhaustive list, but it’s a good list to get you started.

How does clarity affect my designs?

Let’s look at three specific examples. You may recognize yourself in one of these.

Clarity zero – Designing solo

Clarity is something you have to actively work towards. The desire to achieve clarity as a designer does not come naturally. It’s like working out in the gym. In the beginning, it’s something that you have to force yourself to prioritize. It’s something that you have to train yourself to value.

We all start off at clarity zero. This comes as a result of designing in a silo, with zero feedback, zero regard for existing data or insights, and zero user interaction.

As you experiment with, and begin to embrace the idea that “establishing clarity early on in the design process is a good thing”, it begins to feel a lot more natural. Eventually you’ll get to a place where you’d never even consider designing something without first setting aside time to establish clarity early on.

Clarity 10 – Clarity zero + post launch iteration

With clarity 10, designers do exactly what they did in the clarity zero state, but they also start to retroactively react to user feedback after launching a design. This state of design is slightly better than being in clarity zero, but not much. 🙂 It’s a start. But, you are still delaying any sort of insights or clarity until much too late in the design process.

Clarity 20-100 – Incorporating multiple activities

An easy way to think about it would be to assign 20 points for every activity you engage in to increase clarity with a particular design. If you’re currently at clarity zero, and you begin incorporating one of the activities listed above, BOOM! You’re now at clarity 20. Congrats! That’s really awesome. As you add more activities, your level of clarity begins to stack up.

With each new design, your goal should be to get to clarity 100 as quickly as possible. By combining multiple activities you’ll begin to see a compounding effect, and you’ll also notice a decrease in your “time to clarity”.

Reducing “time to clarity” is absolutely key to becoming a great designer

As you begin to make this a priority you’ll find yourself becoming more efficient, you’ll find that your confidence increases, and you’ll find that the overall value that you can contribute as a designer will skyrocket.


I don’t do comments on this site, but if you have thoughts, I’d love to hear them. You can email me at

Don’t Pay for Design School

You don’t need a degree to become a designer.

I regularly receive pings from friends and family for advice on how to get started in a new design or front-end coding career. The emails usually read something along the lines of:

Hey Dave,

I was hoping I could hit you up for some advice. I’ve decided to switch careers to become a designer. I’m thinking of either applying to this [ENTER_NAME_OF_2_YEAR_UNIVERSITY] course. There’s also this [ENTER_NAME_OF_HIPSTER_DESIGN_TRAINING_SCHOOL/COURSE] which lasts X weeks, and costs $X000. I’m undecided. Which would you choose?


After a deep sigh, my answer is always the same, “I wouldn’t pay for any of that“.

Here’s my reasoning:

The best way to become a designer is to just start designing (same for learning to code)

It often takes a couple of emails back and forth before they really hear what I’m saying, “Don’t waste your time/money with these programs, just pick a project that you want to build, and build it. Then keep doing that until you’ve got a small portfolio of things that you’ve built that you’re proud of.”

Your quickest path to becoming a good front-end coder or designer is to just start coding or designing. Please forget about school, or some multi-week program. Seriously!

You don’t have to pay thousands of dollars to become a great designer or front-end coder

There is so much info available for free these days. You can probably learn everything you need to know without spending a single dollar!

  • Whenever you get stuck, or when you run up against something you don’t understand? Just turn to Google. Chances are, many people will have asked a similar question, and will have shared a solution that works.
  • will soon become your best friend.
  • is free.
  • Go to your local book store. Grab a book off the shelf. Sit and read it.
  • There are so many great resources out there for learning to design and code. The vast majority of which are free.

We’ve been trained as a society to think: “I’m starting a new career, I guess I’ve got to go back to school”. With regard to careers in design and coding, this is simply not the case. It’s a lie.

The unfortunate bit is that this mentality has lead us to ever increasing student debt levels.

In my full-time job, I manage a team of designers. This may come as a shocker, but when reviewing resumes, I don’t even look at the education section of peoples resumes. Honest, I don’t! The one thing that matters to me more than anything else is your portfolio.

The market is saturated with “product designers” (notice my use of quotes here) who have zero actual experience, but who have gone through one or more bootcamps, and half a dozen Udemy courses. Truth be told, these are simply redflags for most employers.

Given the option between:

1) racking up student loans, wasting time writing stupid papers, and doing countless hours of busy work, or
2) spending your time just building stuff you’re interested in, learning as you go, building a portfolio which will earn you more over time, and potentially charging people for work, or getting a job (where they’ll pay you to continue to learn, and build your portfolio)…

Hands down, I’d go with option two, every single time.

For many, I think the decision to go back to school actually comes down to some amount of uncertainty and fear.

The unfortunate truth is that the fear doesn’t go away just because you attend school

Deciding to build something is intimidating. I get that. You feel like you don’t know enough. Or maybe you legitimately don’t know the least thing about designing.

When it comes down to it, you’re afraid to fail. We all are. This fear is not unique to you.

It’s better to try and conquer your fear now – by just diving in, and deciding to start building something, anything – instead of delaying the inevitable (and racking up more personal debt in the meantime).

Okay… So, where do I start?

Here’s my recommendation:

1) Find a mentor – It could be a relative, a neighbor, someone from church, or a parent from your kids school. Find someone who already does what you’re hoping to do, and ask them to mentor you. Tell them that you’ll try not to bug them, except for times where you really get stuck. This person becomes your lifeline whenever you hit a wall.

2) Find a project – It could be a website for a hobby, or for a relative, or for your church, or for something that is completely made up. 37signals, used to make up projects years ago, before ever releasing their hugely popular Basecamp project tracking software. It worked well for them, and it can work for you.

The focus of these projects is to both build up your portfolio, and to learn as you go.

3) Once a project is complete, return to step #2. Then, repeat this cycle until you have a portfolio you’re proud of.

And that’s it. It really is that simple.


I don’t do comments on this site, but if you have thoughts, I’d love to hear them. You can email me at

I’ll Stay Indie, Thanks…

We all know the “Silicon Valley” siren call:


  • you quit your job, and start a company, AND
  • you raise money (early & often), AND
  • you prioritize the growth of your company over everything else in your life, AND
  • you can hang onto the reins for 5-12 years…


  • you’ll be rewarded with a Scrooge McDuck sized money vault, AND
  • you’ll ultimately live a fulfilled, happy life!

I used to sip this Kool-aid…

For years:

  • I devoured Hacker News.
  • I obsessed over my startup ideas, and let them consume my every thought.
  • I soaked up every rags-to-riches startup success story that I could get my hands on.

Thankfully, over the past couple of years, I’ve started to recognize how silly all of this was, and ultimately how empty these promises are.

Over time, I’ve come to realize that:

  • I don’t really have any desire to be super rich. I’m grateful for what I have. I live comfortably, and don’t really need anything more.
  • When all is said and done, wealth will not bring me happiness. It just won’t. In fact, it has the exact opposite effect in many cases.
  • Being the CEO of a growth startup sucks. It’s extremely stressful, and it comes with on-going sacrifices (mostly related to time) that I’m just not willing to make.
  • Many people look to entrepreneurship as an escape from the rat race (i.e. a job they hate). It’s not an escape from the rat race, it’s merely a transition to an entirely different rat race – where instead of chasing money, and position, you’re now chasing money, fame, and head count. As the founder of a VC, or angel backed company, the sad reality is that you’ll be even more trapped than back when you were an employee. As an added bonus, your performance will be under a microscope until either you exit, or they kick you out.
  • The joys felt after exiting a startup are short-lived. It’s common knowledge that most businesses are doomed to fail, but let’s say that luck is with you, and you do happen to strike it rich… What next? Now you have a bunch of money, but your business is no longer yours. If you’re acquired, you’ll be stuck as some boring enterprise for another 2-4 years. You’ll long for that rush you felt as a founder, and the emptiness will eat at you.

Unfortunately, this side of the startup founder equation is seldom talked about. Conveniently, you only hear about the unicorns, and the overnight success stories.

It’s been a long time coming, but…

I no longer have any desire to start a startup (Yay!)

Instead, I’ve selected a different path. I chose to stay indie (working on side-projects while still employed).

The formula is simple:

  1. Find a job you adore (where the compensation meets or exceeds your needs)
  2. Keep your job
  3. Build fun projects on the side (limiting yourself to an hour or two each weekday outside of work)

I consider myself extremely blessed to have stumbled into Wildbit. We’re treated well. We’re trusted to do our job. I work with super smart people on a product that thousands of people love. It’s my dream job really, and I plan to stay there for a very long time.

Giving up my startup obsession set me free

I no longer dream of quitting my job. I no longer fantasize about starting my own business. I no longer obsess about business ideas with every passing thought.

I feel more balanced. I feel happier. I feel healthier. And while I do plan to continue tinkering with projects on the side, money is no longer a primary driver. It’s so freeing to work on a side project, and know from the outset that it doesn’t need to turn into a business that will conquer the world, and it doesn’t have to grow into something that can replace my current salary. It can just be a fun little project!

Not every technology business needs to be a unicorn. Not every side project needs to be a full-blown business with employees, an office, and investors. For all of the hype around becoming a startup founder, I honestly thing that it’s just not all that it’s cracked up to be.

I for one choose to stay indie.


I don’t do comments on this site, but if you have thoughts, I’d love to hear them. You can email me at

My Origin Story

My name is Dave Martin. I’m a seasoned product designer.

It all began as a hobby

I started with HTML back in 1999.

I never expected to make money from it, let alone make a career out of it.

That turned into a side hustle

In 2000, I was pulling down a whopping $7.50/hr working produce at Safeway.

The first website I got paid to design earned me $500! At the time, that amount of money rocked my world.

By 2002 I was studying to become a chiropractor, continuing to work on little web projects on the side to help pay for school.

Looking back, I wish I had recognized this earlier, but I never really wanted to be a chiropractor. It just seemed like a respectable profession. My goal was to have a job that I could work 3 days a week (to pay the bills) leaving 2 days a week for me to play with web stuff on the side.

Around 2004, I won a couple web design contests at my university. This caught the attention of a guy named Adam who was launching a startup. He wanted me to join his team. Up until this point, it had never really dawned on me that I didn’t have to become a chiropractor. The idea that I could make a living doing this “web stuff” full time was a major epiphany.

It still required a leap of faith

With 2 semesters left to go, I dropped out of school to join Adam’s startup.

Looking back, it’s was one of the best decisions I could have ever made.

Since then I’ve had the pleasure of working for several amazing companies, and I’m currently the VP of Product at Help Scout (my dream job).

Time to give back

Over the years, I’ve learned a lot, and I’ve been very blessed to work with some extremely smart people. I now feel a strong pull to give back.

User League is my attempt at doing just that.

If you’re just starting out, I want to help point you in the right direction. If you’ve yet to take the dive, I’d love to help you find a way to transition into product design. If you’ve been at it for a while and you’re looking for ways to level up, I’d love to help you figure out how you can get on the right path toward landing your dream job.

My way is not the only way, but it’s worked for me. My goal with this site is to share one solid interview, article, or resource a week, and to keep sharing until I have nothing left to share.

Where are you at in your journey?

I’d love to hear from you. Please let me know how I can help.

Much love,

Dave Martin