A Decade of Lessons from a Freelance Product Designer

Jonathan Patterson
9 min readApr 1, 2021

You want your design work to be fulfilling. You want your projects to be successful. And to win the best jobs, you want to know your strengths and gain the competitive advantage. I know, because I’ve been in your shoes. These were missions I wrestled with as I launched my freelance business more than 10 years ago. And along the way, I’ve identified some fundamentals that helped me, pixel by pixel, reach my goals. Below, I’ve synthesized my findings and time-tested philosophies that helped me. I’m hoping they’ll benefit you too.

Pop the bubbly!

First of all, I’d like to propose a toast to you, wherever you are on your journey into the world of freelance product design. As for me, whether you know me from my Vectortuts tutorials 10 years ago, or through my most recent work, the pertinent fact to know is the decade I’ve spent as a full time freelance product designer, solving challenging UX and UI problems — and the five important tenets I’ve seen running the deepest through the past 10 years of my career. Let’s have a taste.

Lesson 1: The Eureka Myth

Forming big ideas and “aha!” moments

I learned that boredom is the proprietor of great ideas. It’s the space necessary for our minds to work through all the stimulus we consume on a daily basis so that we can extract, convert, and remix them into new ones. Ideas don’t come from thin air, but they do need headspace to thrive. And If you’re anything like me, you have some idea for a new app, product, service (fill in the blank) that you want to create or try.

When I first began freelancing full time, there were days when work wasn’t steady. It would have been all too easy to distract myself with TV, or other generally aimless pastimes. But it was in those moments that I had some of my most rewarding ideas. I daydreamed about the trajectory of my career. I envisioned the types of projects I wanted to work on. What transpired was a strategy. A roadmap to later manifest my goals. In fact, a stepping stone conceived from boredom was deciding to write tutorials about creating vector graphics.

You see, ideas develop in the subconscious, sometimes over a short period of time, or even over several years. Boredom is like an inspiration rave for your brain cells. It may be the catalyst of great ideas, but in order for them to grow, you need to be mindful of how certain activities impede or influence that process. Activities like streaming videos and swiping through your social network feeds are more distracting than helpful. They surreptitiously steal time and brainpower, hampering your ability to process your thoughts and ideas without you even realizing it.

And so, when you’re doing the most mundane of things, like washing dishes or working out, or even sitting around bored — that’s prime time for your brain to do big things. Thus, when you finally begin click-clacking away at your keyboard, creating that next big thing you only just thought of, know you’re actually unfurling ideas that could very well have been years in the making. So-called “down time” is anything but unproductive if you know how to harness it.

Now, while you’re harnessing that inspiration, the next lesson is paying attention to where that inspiration can lead.

Lesson 2: Opportunity Cost

How we sabotage design opportunities

I once made the mistake of having little foresight. Or maybe, call it lack of wisdom. A big-name SaaS company approached me to work on a product redesign. Cool product? Check. Friendly folks? Double check. Optimal budget? Fail. It had nearly all the attributes of a stellar project. But instead of taking it, I took another, higher-paying project. Big mistake. Here’s why.

By definition, Opportunity Cost is “the loss of potential gain from other alternatives when one alternative is chosen.” While it’s rooted in economics, Opportunity Cost applies to many things, including product design.

To be clear, Opportunity Cost is not about maximizing earnings. It’s about maximizing your opportunity. The future is by all odds unknowable, but we can be certain that working on a product design project for a large technology company, or any well-known company for that matter, will likely lead to other opportunities. Repeat business, referrals, and being a company’s go-to product designer where people move to new companies, paves a direct path to new work possibilities. With any luck you’ll have the privilege of being able to work on many other high-paying projects for well-known brands as a result.

Had I taken that other project from the big-name SaaS company, what cool opportunities would have come? That’s unknowable. What I do know is that the potential client never returned — and I’m down a cool project that could have been a killer portfolio piece, as well as a great learning experience. I fell prey to Opportunity Cost because I focused on one facet — project rate. The lesson here is to know that rarely are there perfect projects that check every single box. It could be a tight timeline or confusing project requirements. Whatever the case, have vision for what may be, and not for only what is in front of you.

Of course, making decisions about which opportunities to pursue are just one pixel out of the enormous canvas of decisions you face every day. Let’s consider some of those and how they affect our thought processes.

Lesson 3: Decision Fatigue

The co-conspirator of mediocre UX design

As an independent product designer, there are no shortage of tasks I tend to on a daily basis to keep things operating smoothly. Deciding to invest time (or money) into new design software, troubleshooting ill-timed IT problems, or on a more casual level, deciding what content to stream on Netflix. Everyday we make an untold number of decisions at a cost far greater than we may realize.

Each decision we make comes with the unwanted side effect of reducing our ability to perform tasks rapidly and skillfully. We know this incremental downward shift over time as Decision Fatigue. Indeed, the process of making decisions reduces cognitive performance, irrespective of the decision actually made.

One of the most dubious instances where we experience decision fatigue is when we endlessly scroll through apps like Netflix or YouTube, searching for something to watch. It’s the modern equivalent of “channel-surfing” — a hallmark of cable TV. Over the years I’ve worked to resist that temptation and form new, healthier habits that mitigate this phenomenon, so that as a UX and UI designer my work is always top-notch.

First, I start my workday by prioritizing product design challenges. I leave Slack calls to discuss requirements for future tasks, or replying to emails that take more than a few minutes to compose to later in the day. I focus on doing product design work first, to ensure my most well-thought-out and creative ideas become actualized. I also limit context switching. That is, switching from one task to the next — especially an unrelated task. After all, complex UX tasks generally need concentrated thought. So, I work on similar tasks consecutively.

Even automating mundane decisions helps combat decision fatigue. Think of CEOs who wear the same type or color of clothing day after day, or have a personal assistant who handles their meals for them. For those of us who aren’t CEOs or enjoying the luxury of a personal assistant, reducing the number of decisions we make accomplishes a similar result. This might be meal-prepping lunch for an entire week, or having a set of go-to shirts (and pants, ahem) for video calls.

So whether throughout the course of your daily life as a product designer, or after hours in your spare time, know that the myriad decisions you make take their toll on your mental acuity. Saving your mental energy for UX tasks can make all the difference in the quality of your thinking and your work.

Speaking of thinking, sometimes our focus and dedication is better spent in the decision to cut our losses. Which leads me to lesson 4.

Lesson 4: Sunken Cost Fallacy

Why we ignore our better judgement

I remember toiling away on a project, working every which way to get the design to come together. Adjusting the fonts, tweaking the color palette, incorporating different icons. I stepped away and came back with fresh eyes. That didn’t work. I adjusted the grid. That didn’t work either. In my heart of hearts I was starting to think the problem might be more systemic, but I forged ahead. My inclination to continue devoting more time because I’d “come too far” was the Sunken Cost Fallacy at play.

Psychology describes this fallacy as an incurred cost that is not recovered. Sunken costs can be time you’ve spent working on a design, or money you’ve spent holding on to a parked domain you’ll never use for instance.

In the example above, costs were further sunk by continuing to work on a design when what ended up being better would bear no similarity to what came before. In my effort to not have wasted a bunch of time designing something that I couldn’t use, I kept working.

To avoid falling prey to sunken costs, ask yourself if what you’re doing is accomplishing what you set out to do. Recognize the difference between putting in the due diligence to make a project come together, versus being unwilling to accept the inevitable. Sometimes you’ve got to make the decision to bust a move — get out of the rut and try something new.

While this is one crucial step in the thought process that can keep us from wasting valuable time and energy, there’s one more logical process I use to help my business stay on track. Let’s move to Lesson 5.

Lesson 5: If-Then-Else Statements

Conditional logic and daily routines

Beyond software, as a company of one, carving out efficiencies helps me maximize profit. One of the ways I do this is by using if-then-else statements in my daily routine.

If-Then-Else is a nice mental dance step that helps you stay gainfully employed and build a recurring base of clients that faithfully count on you to handle any of their user experience tasks.

What does that look like? For starters, I always know what I’m going to be working on the following morning. Whether it’s UX/UI for a client project, or something else business-related, I make sure to plan out what I will do the next day.

Say for example, I’m working on a project and waiting on some feedback on a particular interaction I’ve designed. My behavior would go something like… “If” the client doesn’t approve the UX pattern I proposed by the close of business “then” I’ll work on another facet of the project that needs my attention. The part that comes after “then” can be anything. Moving on to other unrelated tasks, etc. The benefit is that I’m not sitting around waiting, or thinking, of things to do while the feedback loop comes full circle.

I use If-Then-Else throughout the lifecycle of a project. Take vetting and scheduling prospective product design projects as an example. I used to provide availability to someone or some company interested in hiring me while at the same time entertaining other potential clients interested in getting my help. I would anxiously wait for an answer from one client before giving the second client the option of working together, regardless of whether it conflicted with the first timeline. Times where the first client decided not to move forward left me clinging to the possibility of the second client’s business. Needless to say, when neither project progressed, I wasn’t too happy.

If-Then-Else would ameliorate this. “If” the first potential client didn’t get back to me by “X” date or time, “then” I was ready and willing to make a deal with the second client. I stopped letting the uncertainty of client indecision jeopardize my future income.

The value of If-Then-Else is many-fold. It allows you to be productive at every moment, in any situation, whether it’s your business or your personal life. Clients love it, because those of us who use it are not in need of micromanagement, and that saves them time and hassle too!

How’s About a Top-Off?

It’s been fun walking through some of the ways I’ve managed to stay self employed over the last 10 years. Making space for big ideas. Having vision. Putting creative tasks first. Understanding what’s due diligence — and what’s not. And having a backup plan. While these tenets only scratch the surface of what it takes to run a successful freelance product design business for a decade and counting, they’re great fundamentals to incorporate.

If you’re interested in hearing more about what my years in the industry have taught me, there’s an afterparty or two in your future for sure. I’ll be writing about several other topics this year. One topic is a question I’m asked often — how I made the leap to full-time freelance product design. I’ll also be taking you through how to make a great product design portfolio. Keep an eye out for those — and thanks for stopping by. Cheers! Here’s to 10 more years!

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Special thanks to Jon Yablonski



Jonathan Patterson

Senior Product Design Generalist: I'm the hidden expert behind your everyday digital experiences.