Microwins: A Healthier Approach to Goal-Setting and Productivity

Here’s a great example. I first read Steven Pressfield’s The War of Art in one sitting over the Christmas holiday in 2016. At the time, it spoke to me about my need to hone my craft as a musician and a songwriter. For the next 67 days, I cranked out one song a day like clockwork. Nothing got in my way. Until I made a trip to visit a college bandmate. We were noodling around on guitars at his house and it struck me: he is so much better at guitar than I am. 

The internal voices took that and ran with it. They filled in all of the other blanks with “I’m never going to be that good.”
And so guess what? I stopped my 67 day streak on the spot. I don’t think I wrote another song for months. 

It should be said I’m not a total productivity slob. I’ve run a marathon and several half marathons. I’ve orchestrated a massive career change in my late 20s that got me to the University of Texas at Austin and on my current path today. 
What I’m doing has gotten me this far. But it’s also not going to get me to where I want to go.

The Impact of Shame on Productivity and Consistency

Let’s talk about shame. I work with men across generations on a spectrum of issues, and the one common denominator I find in guys that end up on my couch is shame. It’s the elephant in the room.

A study published in 2024 in the Journal of Social Psychiatry found that 67% of men experience men, and of them, 67% experienced shame related to work. 

We live in a world where, at the end of the day, a man is measured by what he produces. Sure, us younger generations of guys are expected to be emotionally intelligent, vulnerable, empathetic, and all of that good stuff, but that doesn’t change the fact that the bottom-line KPI for a man in America in the 21st century is what he earns financially.

Don’t believe me? Three out of four women say economic viability is key to a mate. For men, it’s one in three. So when we as men are not producing, we are going to feel ashamed. Shame is the key lever in the productivity conversation.

Working with Shame to Achieve Our Goals

So how do we eat the shame elephant? I’ve lived long enough (and fallen on my face too many times) to know that I can’t outrun it. I also can’t trick myself into thinking it doesn’t exist.

We need a different way.

Enter the Microwins system, brilliantly crafted by a man I look up to like a 13-year old suburban middle school girl looks up to Taylor Swift. The man is Daron Roberts. He’s a Harvard Law grad and former NFL coach who now spends his time speaking at Fortune 500 companies across the globe, writing books, and raising 5 kids. I was lucky enough to work as a graduate teaching assistant under him during my last two semesters at the University of Texas. 

Here’s Daron:

“Microwins are small units of victory that chip away at big goals… It challenges the notion that bigger is better. We embrace and celebrate small units of victory. Why? Because our road to fulfillment and joy runs through the checkpoints that don’t show up on maps. But it’s the small work, the stuff that no one cares to see, that will catapult you to your final destination.”

I went and saw Daron at a Q&A here in Austin for the book launch. Here’s the simplest way of looking at it. 

Let’s say you want to write a book this year. A typical nonfiction book is 50,000 words. Bam. Our brain is already going into “WTF?!” mode. It can’t compute sitting down and writing 50,000 words.

But Daron’s point with Microwins is this: today I’m going to sit down and write 250 words. And if I can do that 200 days this year, there’s my book.

So for the past month, I have set out goals in three categories every night.

Family

Health

Work (ranked by priority)

Have I turned myself into David Goggins or Jocko Willink overnight? Definitely not. But I wouldn’t be writing this if this system hadn’t already changed my relationship with productivity. Today is my 28th day of Microwinning. In that time span, I have an 80.95% average. That’s a C+ by most standards. But, as Daron says, .300 is a Hall of Fame batting average. 

Is it nice to get stuff done that I don’t necessarily want to do? Sure. But this system has given me so much more than that. Microwins are fundamentally changing my relationship with myself because they are the antidote to my decades-old self-defeating stories. Those are the narratives and inner monologues that want to keep me small, safe, and comfortable, that don’t want me to break out of my comfort zone and into my greatness. Every microwin is a deposit into my “I Can Do This” account. 

Even though he sometimes falls into the rise-and-grind bucket, I really love this quote from Alex Hormozi:

“You don’t become confident by shouting affirmations in the mirror, but by having a stack of undeniable proof that you are who you say you are. Outwork your self doubt.”

What I’ve found is that by setting time aside to move the needle each day in three important categories, those shame demons get drowned out. They're still there, but they don’t have a bullhorn. They’re in the car, but they don’t get to pick the music. 

Will I still procrastinate and have unmotivated days? You betcha. But I’m learning a fundamental truth: If I’m procrastinating or avoiding work, it is almost, without fail, a scale issue. I’m trying to bite off too big of a piece. And that leads to freeze, inaction, and shame. 

There’s only one way out, and it’s not whipping yourself to death. If you’re like me, you’ve probably tried everything else. Might as well try a way where you’ll love yourself at the end of the day.

You can buy Daron’s book here and find out more about him here.

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