WWHD: What Would Hemingway Do? The Life Hack for Building Play Into Your Big Goals

@KindEdge

June 4, 2026

The Hack I Wrote on a Sticky Note During a Hard Season

A while back, during a particularly demanding stretch of doing the hard work of the Project of You alongside the logistical chaos of rebuilding my house after two back-to-back hurricanes, I noticed something. I was grinding. Just grinding. Head down, relentlessly pushing, doing all the right things but running on empty in a very specific way.

The work was getting done. But the childish, experimental, ridiculous energy that I know I need to do creative work sustainably was not getting replenished. And that is a problem.

So I wrote four letters on a piece of paper: WWHD.

What Would Hemingway Do?

Why Hemingway? A Brief and Honest Portrait

Ernest Hemingway was one of America's greatest authors. A pioneer in writing style. A journalist, a novelist, one of the greats by any measure. He was also, by any honest accounting, a selfish man. He cheated. He burned through marriages and money and relationships. I am not endorsing any of that.

But here is the thing about Hemingway that I find genuinely useful as a mental model: he was completely unapologetic about protecting his energy and his play.

He wrote every single day from about 8:30 in the morning until about 2:30 in the afternoon. Dedicated, disciplined, uninterrupted. And then when the work was done, it was done. He went straight to a bar. He got on a boat and went fishing with friends. He caused a little trouble. He was fully, enthusiastically off the clock.

He did not grind straight through from 8:30 a.m. until midnight and call it productivity. He worked hard and then he played hard. And the playing was not a reward he had to earn or justify. It was simply what he did.

We all need to build that into our long-term plan to make things sustainable. You've got to have rewards, breaks, stupid fun, playfulness, messing around, pointlessness. You need to rebuild that fun, experimental, childish energy.

The Selfish SOB Permission Slip

I want to be clear: when I invoke WWHD, I am borrowing about 2% of Hemingway's selfish energy. Just the part about protecting time for play and reward and going to the pub when the work is done. Not the rest of it.

But that 2% is actually quite radical for most of us. Because most of us have been conditioned to treat rest and play as things we earn after we have done everything on the list. And the list never ends. So the play never comes.

The WWHD hack is a permission slip. It says: I am doing the hard work. I am showing up for the Project of Me every day. And I am also going to go eat dinner at a restaurant and chitchat with strangers and call that a win. I am going to go sit outside and do nothing useful for 45 minutes and call that part of the plan.

Because it is part of the plan. The play is not separate from the goal. The play is what makes the goal achievable over years, not just weeks.

What WWHD Looked Like in a Practical Moment

Here is a real example. During the house rebuild, I could not easily access my own kitchen. Workers everywhere, the mini fridge moved around, no reasonable way to cook. My first instinct was to white-knuckle it and figure out the most efficient, budget-conscious, responsible solution.

Then I asked: what would Hemingway do?

Hemingway would not stress about the mini fridge situation. Hemingway would go down to the local restaurant, sit next to some strangers, eat something good, and enjoy it. So that is what I did. Not every night. Not extravagantly. But I stopped treating it as a failure to manage and started treating it as a small act of self-honoring in a chaotic season.

That is the WWHD mindset in action. It is not about ignoring reality. It is about refusing to let reality squeeze out all the oxygen of joy.

Why Play Is Not Optional in the Long Game

Any big goal, whether that's writing a book, starting a business, training for a marathon, changing careers, or building something from scratch, is a long game. And long games require sustainable energy.

Sustainable energy does not come from grinding and hoping the reservoir refills on its own. It comes from actively building in the recovery. The fun. The rewards. The stupid, pointless, childish playfulness that reconnects you to the part of yourself that actually wants to do this.

I do not want you to be as naughty as Hemingway. But I do invite you to consider how you would approach the long game by adding in a little bit of Hemingway-style play. Go mess around. Cause a little trouble. Hop on the metaphorical boat.

You will be respected for the work you do. But you can also go play.

Join me at kindedge.com for the full Project of You process — realistic, bite-sized, actionable, and yes, built for humans who need to have fun along the way. It is not going to be easy. But it is going to be fun.

Latest Posts

WWHD: What Would Hemingway Do? The Life Hack for Building Play Into Your Big Goals

Grinding yourself into the ground is not a strategy. In this post, I share the WWHD life hack — What Would Hemingway Do — and why building stupid fun, pointless play, and unapologetic rewards into your long-term goal is the only thing that makes it sustainable.

read more →

Don't Die Waiting for Godot: Why Action Today Is the Only Thing That Works

Spoiler: Godot never comes. Let’s use Samuel Beckett's Waiting for Godot as a life hack reset — if you are patiently waiting for something to feel good and fulfilling, the wait is the trap. Here's why action today is the only thing that actually moves the needle.

read more →

From Friction to Frictionless: The Real Easy Button for Big Life Change

The reason most people fall back into old patterns isn't willpower — it's friction. Let’s break down how to identify friction, remove it systematically, build daily rewards into the process, and rewire your default mode one sustainable step at a time.

read more →