Perfectionism – The #1 Obstacle Between Freelancers & Making Six Figures Consistently

The single biggest problem that most freelancers and consultants have is perfectionism. At least, it’s the obstacle that stands between them and fixing problems quickly, consistently earning six figures, and ultimately optimizing for lifestyle.

We don’t realize that a driving need to get it right, whatever it is, makes decisions for us, like an invisible hand moving pieces around on the chess board. We may describe a feeling of stuckness or inertia, which is one of the four growth-squashing defaults Shane Parrish describes in Clear Thinking, yet we find it difficult to put the root problem into words:

• “I feel like I’ve plateaued,” a strategist and copywriter confided.
• “What’s holding me back is not understanding what I need to do,” a motion designer said.
• “I feel trapped. I’ve built it up to this point, and I’m looking to go to the next level,” an Excel and automation specialist admitted.

We’re not going to solve the problem of perfectionism in one post, but I do want to tell you a story about an insecure poet and shiver of sharks that illuminates how a chronic hesitancy seeped into my work. After that, you’ll get a piece of advice for weakening perfectionism’s effects.

Who knew poets could be so savage!

In August of 2006, I started an MA in Literature program in Knoxville, Tennessee, and signed up for a poetry writing workshop, an odd choice in retrospect because I’d entered the program as a fiction writer.

When my turn came to read one of my poems and receive critique from my fellow MA and PhD candidates, I chose one I’d written about a whitetail deer. Heart-shaped prints in the loaves of snow. Something with dazzling originality like that.

I probably thought I was making a safe choice, leaning toward impressive, and boy, was I wrong!

The poem was short, less than twenty lines, and after I finished reading it aloud, someone doffed a stained fishing hat and dumped cut bait into the water. All the sharks got a sniff of delicious blood. The feeding frenzy began. Who knew that a bunch of poets could get so savage so fast!

Eventually, everyone so inclined had taken a bite out of the poor poem, and my confidence with it, and I was left with a bunch of notes on a poem that wasn’t salvageable. Or so all the cutting remarks had led me to believe.

My belief in myself walked out of the room with a metaphorical limp. A thought crossed my mind more than once: Maybe this was a mistake. Maybe I’m not cut out for this.

How did that experience change my creative practice?

Though I didn’t drop out of the program, I did obsess over every word, phrase, and idea. I probed for weakness. I policed my creative work, hoping to catch the perpetrators before my colleagues did.

Is this stanza “too romantic” like that first poem?

Is this word choice too pedestrian?

Is the whole thing derivative?

An overnalyzing technician replaced the wildly curious scientist playing with language. Without noticing the shift, I strove to avoid mistakes rather than break into rich, new territory. Slowly, I became a better craftsman of words, but vigilance and caution, not curiosity and the joy of exploration, drove my creative choices.

You don’t need to feel sorry for me because this isn’t a coming of age story about poor Austin, the insecure poet. And your takeaway isn’t to avoid peers and collaborators who love critique itself more than the possibilities of the work they’re critiquing.  

No, the point I want you to remember is that the technician mindset slows our progress to walking backwards in knee-deep mud.

Technician vs. Entrepreneur

When I first stumbled across the idea of the technician versus the entrepreneur in Michael Gerber’s The E-Myth Revisited, I felt like I was seeing the matrix. The technician mindset with all the perfectionism it entails had driven so many of my business decisions, rather non-decisions, for years. I’d been acting like a poet avoiding errors, not an inquisitive entrepreneur solving problems quickly.

As pleasant as incremental gains in skill and quality and compliments from clients and peers are, craftsmanship and the technician mindset become a hindrance.

It’s understandable why we don’t notice this problem right away. Many creatives and consultants, including myself, have a background in copywriting, design, filmmaking, or software engineering. Craftsmanship is what we know. What is “good” writing or design if not an assemblage of tiny details that must all work in harmony?

Your business is built around your craft. The two seem indistinguishable.

When it comes time to shift the focus to working on the business, not in it, we take out the familiar tools. We assume meticulous attention to detail is the goal. We maintain a bias toward “doing it right.”

Unfortunately, the problems bound up with creative entrepreneurship are too varied and unpredictable. They come too fast. Unlike a rough piece of writing that can be painstakingly edited to improve quality, a rough piece of a business needs to be addressed quickly.

Take, for example, your offers. I can speculate about “the right offer” for my target audience. I can agonize over the details for weeks. I can polish it until it sparkles, and once I finally push it out into the world, it may meet nothing but deafening silence. Instead of fussing over the cosmetics of an offer that was doomed to fail, I could have launched it in six days, not six weeks. I could have discovered much sooner than no one cared. I could have made a hypothesis about why that was. I could have iterated the offer and tried again.

If I were to go through that launch-observe-improve cycle six times, just think how much closer to true product-market fit my offer would be!

Better craftsmanship can’t fix a fundamentally flawed strategy, offer, or idea. Imagine trying to sand and varnish the keel of a boat that’s sinking!

Building a profitable, satisfying business involves a process not of doing it right but of becoming less and less wrong. In fact, any time you spend deliberating over the right way is time you don’t spend getting new feedback from the market, new intel, new ideas for what to try instead.

Perfectionism is a liar.

Perfectionism never delivers on its promises of better results. It mistakes thinking about doing for decisive action. It relies on a silver bullet fallacy: “Once I find the right solution, I can solve this problem, once and for all.”

Like cars and mindset, businesses have an annoying tendency to not stay fixed. We must keep tinkering, and that’s why the speed with which you find good-enough solutions for discrete problems matters more than the relative quality of any one solution. When solving problems, we need a gorgeous riot of creativity and speed. We need volume, meaning more problems solved in less time.

• You don’t need the perfect prices. You need ones that are a little more strategic and sustainable than the ones you have now.
• You don’t need the perfect CRM. You need to use a spreadsheet or very okay app that will remind you to follow up five times.
• You don’t need the perfect template for your LinkedIn headline. You need the insight that will come on the other side of a headline that’s a little better than the one you have now.

In short, we need a bias toward messy, imperfect action.

Perfectionism’s obnoxious friends

Perfectionism isn’t the only mindset trap freelancers face. You’ve likely met some of its friends:

• Chronic second-guessing and hesitancy
• Overthinking and analysis paralysis
• Imposter syndrome
• Procrastination
• Overwhelm

Take the phrase “messy, imperfect action” and set it next to each one of those traps. It’s not a perfect antidote, but it comes pretty dang close. Even so, nine times out of ten, you’re better off grabbing a good-enough solution and implementing it.

The people who win at this game of creative entrepreneurship aren’t the ones who get it right the first time. They’re the ones who become less and less wrong through definitive action and get it good enough eventually.

Stop looking for perfect solutions and perfect timing, and you’ll make decisions faster.

Make decisions faster, and you’ll solve problems faster.

Solve problems faster, and you’ll grow faster.

Take messy, imperfect action, and you’ll find yourself building the thought patterns and habits of an entrepreneur. You can still love fine craftsmanship, of course. You can even toggle over to the technician mindset when you need to sweat the details. You can be both a technician and entrepreneur, but it’s the latter identity and mindset that will enable you to solve the problems and make the decisions that build a profitable, satisfying business—one that bankrolls the lifestyle you really want.

When you’re ready, here are 3 ways I can help you:

1. Freelance Fixes. This short guide walks you through 6 small but important “fixes” that you can make to raise your income without working longer hours. People really seem to like it.
2. Morning Marketing Habit. This course will help you build an “always be marketing” practice, become less dependent on referrals, and proactively build the business you want with the clients you want. My own morning marketing habit has enabled me to consistently make  6 figures as a freelancer.
3. Clarity Session. It’s hard to read the label when you’re inside the bottle. I've done well over 100 of these 1:1 sessions with founders, solopreneurs, and freelancers who wanted guidance, a second opinion, or help creating a plan.