Complexity Is Easy

“Simple can be harder than complex: You have to work hard to get your thinking clean to make it simple. But it’s worth it in the end because once you get there, you can move mountains.”    -Steve Jobs

As software continues to eat the world, it is also eating our wallets.

68% of software projects fail. Let's pause and think about that for a minute. One out of every three projects become what might be considered successful. I would classify successful as within budget, on time, provides value, and delightful client experience.

The high failure rate translates to an estimated $75b a year in rework and abandoned software projects in the US alone. I know, crazy right?

One primary reason so many projects fail is that we tend to add complexity in all areas. From the early sales calls to gathering requirements, to managing expectations, to delivery, to launch, and everything in between.

Simple Over Complex

From my experiences, I firmly believe simple is the way to go from start to finish.

At Skiplist, we deeply believe in simple over complex. Simplicity enables us to stay lean and continuously deliver value. We call this approach Thoughtful Software™.

My hope is you will find the simplistic approach informative and helpful in breaking down complexities you may encounter.

Ultimately, our goal is to work together to flip the abysmal 68% failure rate statistic on its head and transform the software industry.

This is our challenge. There is nothing revolutionary here; it is just hard to do.

Life is simple. People make it complicated.

There are no shortages of complicated processes and applications in the software industry. People love complicated. It is human nature to add twists, turns, and drama.

Our brains crave stimulation. It likes to stay busy. We tend to think something can't be this simple and proceed to believe it is more complicated than it is. Commonly referred to as a complexity bias. Relationships, health, and of course, software all succumb to our preferences. It is within these biases we sidestep the need to understand.

"Complexity bias is our tendency to look at something that is easy to understand or look at it when we are in a state of confusion and view it as having many parts that are difficult to understand." Farnam Street

The problem is that complexity requires more effort to sustain it. There are more chances for a system to break down with more parts.

Simplicity, on the other hand, requires more effort to achieve it. It takes mental brain power to break down a problem to its simplest components.

Take the iPhone as the quintessential example of a complex system tirelessly broken down to simple user experience. Whether you prefer iOS or Android, the iPhone is super easy to use. Apple took a product as complex as building a smartphone and turned it into a device my mom can use like a pro. Brilliant.

Unfortunately, we don't take cues from successful companies such as Apple. Our propensity to continuously fill our minds with noise creates a sense of urgency around missing the latest information.

It is this constant flow of information where we blur the line between utopia and reality.

To-Do or Not To-Do

Take our obsession with to-do lists. I did a quick search on the app store and found at least 30 or more task planning apps. Why are there so many of these apps? Utopia is, I'll be an organized ninja and cut down each task one by one. Reality is, after failing time after time to organize the 100 things I have to do every day; I gave up and came up with a simple system.

Every day, I come up with my top three essential tasks I must finish and make sure I get those done before the end of the day. Get to my three and everything else I can adapt. I'll block out time for my top three, but I keep a fluid schedule otherwise. Too many tasks and apps were too complicated.

I believed the process of getting things done required an elaborate system of apps intertwined in the cloud. What I needed to get organized came down to a piece of paper, a pen, and my three things for the day.

Please don't feel too bad for yourself or me. Complexity sells. Simple is thought to be boring. It might be, but it is also useful and sustainable.  ‍

"Everything should be made as simple as possible, but not simpler." – Einstein

Complexity is free

In his book "Thank you for being late," Thomas Friedman discusses how the accelerated advancement of hardware and software over the last 20 years has allowed companies to introduce products into the market at a rapid pace.

What once took two years to develop a prototype, is now reduced to a week. We can leverage three-dimensional software, 3-D printers, cloud technology, and several other advanced tools; essentially, the underlying complexity to build a product is now free.

We don't have to think about spinning up a server or even managing it. Just build. Money has also become more accessible through crowdfunding and the growth of venture capital.

Although Friedman explains that complexity became "fast, free, easy for you, and invisible," it also comes at a price. Our ability to build products quickly allows us to throw whatever feature we want in without truly understanding the consequences.

We are in the age of accelerators. Computing, access to information, access to people, everything around us is changing rapidly. Maybe this is the new norm. After all, the software industry is only a few decades old. Perhaps this is the time to, as Mark Zuckerberg says, "move fast and break things."

However, I argue moving fast does not mean we should be reckless. Moving fast does not mean we should compromise our privacy and security. Moving fast does not mean we should build crappy products. Moving fast does not mean we should add complexity unnecessarily.

We should instead move thoughtfully and break the status quo.

First Principles

First-principles is an effective strategy to break down ideas to their fundamental truths. Mostly think like a scientist to understand what we know about a problem. This type of thinking can open up new ways to attack a problem.

No one today embodies first principles thinking and breaking the status quo more than Tesla and SpaceX founder Elon Musk.

Elon Musk famously said in an interview:

"I tend to approach things from a physics framework. Physics teaches you to reason from first principles rather than by analogy. So, I said, okay, let's look at the first principles. What is a rocket made of? Aerospace-grade aluminum alloys, plus some titanium, copper, and carbon fiber. Then I asked, what is the value of those materials on the commodity market? It turned out that the materials cost of a rocket was around two percent of the typical price." - Elon Musk

From Musk's viewpoint, he believed his vision to reach Mars would not be feasible with the status-quo. Rockets were just too expensive, and if he understood the underlying problem of why rockets are expensive, the next logical move was to build his own.

Thus, SpaceX was born, and a fundamental difference with SpaceX rockets is they are designed to be re-usable. In a traditional space shuttle, the large fuel tanks and side boosters are discarded after every launch. Knowing fuel costs are the most expensive part of a rocket, Musk thought to himself, why not figure out a way to land the rocket safely to be able to reuse the fuel tanks.

I'm ridiculously simplifying what Musk thought here.

Notice, to build and land a re-usable space shuttle is a complex project. However, Musk broke down the high cost of rockets to a simple thought. Re-usable rockets. Going to Mars is about as exciting work as you'll ever find.

Musk will admit thinking from a first-principles perspective "takes a lot more mental energy." It is easier to explain than it is to practice.

What Musk is advocating is to break things down to their fundamental truths. In other words, get simple. Therein lies our challenge. Simple is hard to do.


Lego is a great case study of a company that chose to eliminate complexities in manufacturing and operations. Founded in 1932 and until 1998, Lego turned a profit every year until after a series of self-inflicted mistakes led Lego to nearly collapse in 2014.

Jorgen Knudstorp took over as CEO and a principal mandate for him was to simplify everything at Lego. He started by reducing the number of pieces from 12,900 to 7,000. They implemented smart manufacturing practices to reuse certain parts for different sets to reduce the cost of new molding.

By simplifying how Lego operated, they turned around a nearly bankrupt company into one of the largest toy manufacturers in the world.

Lego’s turnaround illustrates a significant point about a simple mindset. There isn’t anything groundbreaking in what they did. Lego just had to think hard about its business and get creative.

To “move mountains” as Steve Jobs put it, requires us to dig deep and evaluate every aspect of a service and products company.

‍Thoughtful Software is Born

When we set out a few years ago to start a software company, we knew we wanted to take a different approach. We looked at every aspect of building a services and products company — everything from legal to sales to engineering.

We have never lost sight of the high project failure rate in the software industry and our grand vision: thoughtful people and Thoughtful Software™ can change the world for the better.

Granted we are far from achieving our vision but changing an entire industry takes time. We have had our bumps and bruises, and I am sure we will have plenty more. We have also made tons of mistakes. I am not trying to glorify our failures as many do in Silicon Valley. Mistakes are painful. I prefer to make less of them.

The following is a snapshot of how we broke down various aspects of Skiplist built around removing complexity to achieve our vision. We firmly believe if we continue to maintain a simplistic approach, we not only will create more value for our clients, we can stay lean in the process.

A Simple Culture

Thoughtful Software™ is a process, a movement, a mindset, and an approach we believe the industry desperately needs. First and foremost, put people at the center of everything we do.

We noticed a significant reason projects fail is often we lose sight of the goal by adding complexities. We are improving our lives through usable and enjoyable software. We make decisions to solve people's problems, not just write lines of code into a machine.

To manifest a culture around people and delightful client experiences, we knew we had to start with a core set of values. Values guide us through difficult times and around blind corners.

Initially, we had ten values, but when we couldn't remember them all ourselves, it became apparent we needed a more straightforward set of values. Then there were four.


1. Simple over Complex

2. Team over Individual

3. Change over Status Quo

4. Relationships over Money

Rooted in strong values, we can then begin to shape a better client experience. I'll admit creating a delightful client experience is quite hard and I wholeheartedly agree with Musk, it requires a great deal of mental energy.

Expending the extra mental energy to simplify though, is worth it every time. The alternative is the current environment where complexity sells, especially in the consulting industry with more information, more abstraction, and expert hand waving.

Embrace Complexity

Client experiences matter whether you are selling a product or a service. Clients and users have a myriad of options to choose from today.

We should not ignore complexity but embrace it to make better decisions for our clients and users.

Complex products are challenging to learn and use. The iPhone wasn't the first smartphone, and Apple made it simple to use. Complex products and systems are difficult to maintain and can be hazardous within specific applications such as medical and transportation.

When we know where the complexity lies, we can build products and systems and  earn our complexity.

Thoughtful Journey

For us at Skiplist, we didn't set out to revolutionize work or publicize our unique way. We have a standard policy to evaluate and iterate if we can make things better. Be comfortable with changes. Iterate over perfect.

We encourage open communication and lean practices. We are not fans of meetings or busy work and fewer meetings for more focused deep work.

If we do have a meeting, we keep them to 30 minutes or less. I love 15-minute meetings.

In Legal, we have developed a streamlined system to review and sign contracts quickly. I never understood why it takes months to sign an agreement.

In Sales, we are big on conversations over pitch decks. Decks are boring.

We outlined a simple pipeline and sales process. If your sales team is spending more time on data entry than sales, you have a complex process problem, and it costs you productivity.

Excessive data is crippling. We don't need expensive salespeople, spending a large chunk of their day updating the CRM.

In Product, we bring in product managers early to sales conversations to help map out ideas and build out what we call product/project briefs. The briefs help the entire team and the client eliminate misunderstandings.

In Marketing, we believe in no gimmicks to our approach. Chasing search engine rankings and clicks deviates us from the Thoughtful Software™ mission. We focus on only a few things, our podcast, newsletter, and blog.

In Engineering, we often debate the best methods for delivering great work and ask lots of questions.  If we break down a project into eight-week blocks with deliverables every two weeks, would we be able to deliver the value we promised? Do clients understand the deliverables? Are two weeks even appropriate? Simplicity can’t be born from a complex engineering process. We aren’t just looking at agile practices as the “future”; we are always asking how we can simplify our process and practices while creating an exceptional experience for our customers.

Choose Simple Over Complex

All this is to say; we value simplicity. There is nothing revolutionary here, just a relentless mindset to stay focused on achieving our Thoughtful Software™ mission.

The result is our continuous pursuit to choose simple over complex, provide delightful client experiences, and deliver quality work.

Next-generation applications in healthcare, transportation, education, finance, and so on must be simple and effective. We owe it to the betterment of our society to deliver Thought Software™.

If you’d like to learn more about Thoughtful Software™, please contact our team.

"Simplicity is the ultimate sophistication." Leonardo Da Vinci

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