Trying to keep it simple

It’s been a while. And today's topic is not the one I was expecting to explore today. I’ve been working on another piece, one that clearly still needs to marinate a bit longer before I pass it along to you. But, in the spirit of simplicity - I decided to set it aside and talk to you about something else that's going on for me right now.

🫠 The Simplicity Conundrum

Would it surprise you to know that I am a bit of a perfectionist? 🤣

In my long and winding career, I learned to value meticulous execution and highly polished output. Before I joined Google, I spent 4 years at Accenture, a company that thrives on organized structure, and where it was drilled into my head that the first round of review in any document involved flagging typos, formatting errors, and poor grammar. You could only expect your recommendations or attempts at wisdom to be considered if your baseline presentation standards were up to snuff. This habit was ingrained so deeply it became a professional value, and I am still guilty of placing tremendous weight on this type of “delivery excellence” (aka bougie polish) in everything I do - including in my personal life. Now, to be clear, polish really does matter (especially in high-end sales and business), however it’s not necessary in all the things. And it's incredibly easy to get swept up prioritizing form over content in many where it isn’t actually that important.

One of the proactive ways I’ve unwound perfectionistic tendencies is by cultivating more creativity in my life. Imagination and inventiveness are inherently messy, and we generally accept when these things are “raw” (aka unrefined or “sloppy”).

And yet… I still struggle with bringing things in general to fruition. Because for a perfectionist, there is always more to do. There is always a nagging voice wondering if there is a better, faster, or cheaper way to do it.

🔮 The Mirage of "Perfect"

For a perfectionist, simplicity can feel like a mirage. You can spend hours, if not days, shedding all the unnecessary bits to find the core essence of a thing, and shortly thereafter you find yourself layering back on a new wave of “innovations” because more somehow feels... better.

Simple is inherently incomplete. Its lack of detail risks misinterpretation or misunderstanding. When you are a true expert, it can feel like a missed opportunity. And if you're anything like the Broadway version of Hamilton - you don’t want to throw away your one shot - simplicity can feel final and heavy. It falls apart when it’s rooted in a scarcity mindset - because If you only have one single chance to get your point across, it assumes you'll have no option to clarify a point or add more context later. It’s an impossible conundrum.

I am smack dab in the middle of it right now with my latest professional pursuit, a broader launch of my coaching business. And it’s kind of funny (the kind of funny where you realize the joke's on you) because I spent years of my corporate life advising companies on how to do so many of the things I am doing now. And yet, here I am tripping over myself with every step along the way. It's partly because I'm trying something new, but also because I'm being careful about when and where I'm investing money. It often leaves me feeling like I'm caught in an endless web of indecision. Even though I’m making steady progress and forward motion, with every choice I make it seems I unlock a new world of possibilities that require more and more deliberation. It's a roller coaster ride, oscillating between feeling purposeful excitement and total overwhelm.

🌀 The Paradox of Choice

It turns out what I'm suffering from is a common challenge: the Choice Paradox, an idea Barry Schwartz wrote about in the early aughts. I'm maximizing - analyzing every option, trying to make the "perfect" choice - rather than satisficing - locking in the first option that is "good enough" so I can simply move on. Schwartz's book is based on a theory Herbert Simon won a Nobel Prize for in 1978.

There are many places in life I do satisfice. And it is indeed satisfying every time I get to check those to-do boxes off my list. But Schwartz gave the perfect TL;DR on why this dichotomy itself is a paradox: "As a general rule, maximizers do better, but feel worse."

So... what's a girl to do? Am I really stuck in an either/or decision - success vs. happiness?

😫 The Struggle for Simple

Clearly, I am not alone in my strife to find simplicity. For perfectionistic high-performers, over-complication isn't just a personality trait. It’s a design flaw in how we approach high-stakes work. When the pressure is high, our "default settings" revert to a series of psychological "bugs" I've noticed that make the easy path look like a trap. They're the underlying drivers that lead us to maximize instead of satisfice.

Here are the three primary bugs I've noticed are throttling my own progress as of late.

🪲 Bug #1: Directive Drift

One of the fundamental challenges that causes so much churn for a perfectionist is not being clear about - or staying committed to - a specific goal. In the case of my newsletter, I haven’t sent you anything lately because I am actually oscillating between two: (1) regularly sharing content, and (2) offering deep and provocative ideas that I haven't yet figured out just yet.

If my actual goal is #1, then hitting the deadline is more important than deep thought. But if I want #2, depth should win out every time - and it’s worth spending as much time I feel is needed to test and expand different dimensions to discover what I really think. So, when I'm writing something new that takes me longer than I planned, I get caught ping-ponging between two incompatible definitions of success - and my internal circuitry eventually just burns out. It's a dizzying and immensely frustrating experience.

🔧 The Fix: Build a Goal Portfolio. Instead of trying to make every action serve every purpose, get clear on all the goals you're pursuing, and assign specific goals to specific pursuits. It makes sure you're measuring your progress against the right metric, and not criticizing yourself unfairly because you're using the wrong bar.

🪲 Bug #2: The Complexity Cascade

Another challenge I'm struggling with these days is it seems like every decision I make related to broadening my business opens up five new "unknown unknowns," turning a 10-minute task into a 3-day (if not 3-week) research project. Put more plainly, I’m struggling with an acute gap in startup knowledge and experience. While at times I find this exploration to be fun and exciting, other days it leaves me feeling frustrated and tired.

I sometimes wish I had a magic wand, and could send a pack of garden gnomes do the work while I’m asleep - or at least hand over an easy-to-execute checklist that explicitly outlines every step of the way. I’ve looked for the latter - and I've used AI to solve many of the mysteries - but the fan-out of tasks seems to be endless with no end in sight.

🔧 The Fix: Practice Scope Locking. This means committing to solve only for the specific problem at hand. When a decision reveals five new "unknown unknowns," don't chase them immediately. Instead, log them as future projects and force yourself to finish the original one first. You stop fan-out by refusing to let the discovery of a new problem invalidate the progress you've made on the current one.

🪲 Bug #3: Progress Blindness

The last of the struggles I’ll talk about today is something I am calling “progress blindness.” It’s hard to feel like you’re making headway while a big, overarching goal still looms over your head. Major launches and changes of every type are susceptible to this trap, such as releasing a product; starting a business; earning a degree or certification; bringing a baby into the world; moving into a new home; and so on and so on.

The feelings I’ve mentioned at different points in this note - overwhelm, frustration, exhaustion - tend to happen when the sheer magnitude of a big goal creates cognitive overload. When they become recurring or constant, they can unfortunately can lead us to abandon long and protracted pursuits long before they come to fruition, or show up to the big day feeling totally unprepared.

🔧 The Fix: Shorten the Horizon. When we focus on an outcome that is far away, it can make every day in between feel like a failure - even when you're making progress. Instead of measuring the "Gap" (how far you still have to go), start paying attention to the "Gain" (how far you’ve come). When you shrink your world down to the next 24 hours, you see the momentum you’re building and validate the successes you’re racking up along the way.

👣 A Simpler Path Forward

Grappling with overly large, amorphous goals can feel foggy and confusing. But when we slow down and focus on small, singular tasks, actions feel easy and answers often reveal themselves to us. And so my pursuit for the time being is to embrace what’s simple, things that I could describe one of two ways:

1. Easy to understand or do; presenting no difficulty

2. Plain or uncomplicated in form or design

We often mistake "simple" for "easy," but for those of us wired for meticulous execution, keeping it simple can be excruciatingly hard. It requires courage to be uncomplicated, and time to unwind complex ideas.

If you are a fellow perfectionist, I invite you to lean into three ideas this week:

⬇️

Reduce the load

Give yourself permission to choose the path of least resistance. If a task feels like an impossible conundrum, step back until you can find the version of it that feels "easy to do".

📝

Stick to lo-fi

Strip away the "innovations" and "bougie polish" that hides your work's raw edges. Leave the imperfections and embrace the idea of sharing early drafts, even if the form feels unrefined.

🧪

Join me in the lab!

Help me pilot a new program I'm calling Circuit Breakers! We're trialing small, simple actions to break the cycle of overthinking. This week's Patch addresses Progress Blindness.

Embrace the idea of simplicity, so you can clear the fog - and see what's right in front of you.

Wishing you an easy week, where you can keep things simple.

Hope to see you in the lab!

💥 Break Out!