Monkeys On Your Back

I didn't read about this or plan it as some regimen, and honestly it's not ideal. But it's been incredibly effective.

Sort of like that advice about writing down everything on your mind before bed so it lives on paper instead of stealing your sleep - except this is the opposite.

I've been waking up at 4:30 AM feeling great, tearing through my usual routine, but as I'm grabbing my coffee I can't help asking myself: "What's the monkey on your back?" What's the frog you need to swallow? What elephant do I need to start eating?

The reason isn't that I'm going crazy or stuck in some negative headspace - quite the opposite.

I LOVE my morning freewriting sessions. So much spills out: what's really important, home life stuff, concerns, aspirations, learnings I want to share. It's actually critical time for me.

But here's the thing: that joy can fuel procrastination. Discipline isn't doing the things you love on a consistent basis - that should be easy. Real discipline is identifying what's nagging at you and killing it before it grows into something worse.

Monkeys Become Elephants

If I keep ignoring certain things, two big issues emerge:

They're going to become elephants. Bigger, nastier, more dangerous, more time-consuming to handle. Eventually they break your back instead of just riding on it.

I lose focus on what actually matters. I've been taught to focus on strengths and lean into the important, not the "urgent." That's mostly right. But sometimes you need that sobering conversation with yourself about what happens if you keep putting something off.

Take exercise. Skipping today has no obvious impact. I still feel fine, my jeans still fit.

A year from now though? Your resting heart rate has ticked up along with blood pressure, cholesterol, and long-term mortality risk.

Same with the monkey on your back. Mine is doing expense reports (yes, still my nemesis). Today it doesn't matter. But 11 months of backlog later and I've got credit card interest piling up and a long slog of paperwork to figure out what's what.

Here's what I've noticed: asking yourself this question fresh in the morning makes it pretty obvious which things are taking up valuable brain space versus which are just minor annoyances.

There aren't actually that many true monkeys once you look at them honestly.

Date night planning is a monkey.

Date Night Done slaps it off your back for $10 - we bake a little hospitality into your date’s night, and you just show up.

Booking Q1 2026 anniversaries, birthdays and other nights you’ll forget.

It’s never too early but it can be too late.

Make your Date Night Done

The Relationship Monkeys - Different Breed, Same Species

Often those work monkeys are obvious. But there's a whole other list - things I think about for my wife.

Things I wanted to do for her. Things I NEED to do for her that a convenient work discipline keeps getting in the way of. Things she wants me to do. Sometimes as simple as a chore, sometimes as "complex" as sitting down and planning a special night out for her birthday.

If the monkey gets left on my back, I can assure you these things slow us down. They zap productivity, creativity, confidence. The gap between intention and execution creates this friction that compounds over time.

Note of Caution

Unfortunately life is a consumer sport. Annoying chores masquerade as monkeys if you don’t look twice. Honestly I don’t know yet how to tell them apart 100% accurately. But just know that if you start doing chores to fling monkeys off your back, you will spend your entire day on this and there will still be 100 more. That’s not a monkey.

I just check if it’s taking up mental real estate. IYKYK.

Steps to Knock It Off

1. Ask yourself “what’s the monkey on my back?” Just  1x/week ask yourself to answer in the context of your relationship.

2. Take the first hour of work and toss that sucker off.

3. Note how much better subsequent productivity is after you toss said sucker off. 

Don't Let It Ride

You’ll run further faster without their dead weight. And the thing is, monkeys on your back are a fact of life. So, making a small practice of flinging them off is rewarding no matter what modality of life they crop up in.

Sometimes that's letting Date Night Done handle your anniversary dinner. Sometimes it's finally having that conversation you've been avoiding. Sometimes it's just doing the thing you said you'd do three weeks ago.

Whatever it is, give that monkey a new home today. Now go order some stocking stuffers!

🍻
Hat