Negotiating With Comfort

~ David Willis ~ Leave a comment

7-40 Challenge | Rest Week

I read a line today that stung: “You already know what to do. You are just negotiating with comfort.”

I sat with that one a while, because it caught me.

I know what to do. I’ve known all year. The Phase Defiant promotion plan has been written since May — sixty content ideas, a thirty-day blitz, the whole thing mapped out. The first post still hasn’t gone out. Not because I don’t know how. Because every day there’s a quiet negotiation happening, and comfort keeps winning.

The negotiation never sounds like quitting. It sounds reasonable. I’ll start the promotion once the framework is tighter. I’ll launch the product once the positioning is perfect. I’ll post the thing once I’ve thought it through one more time. Each delay has a respectable reason attached. That’s what makes comfort such a good negotiator — it never asks you to give up. It just asks you to wait.

Here’s what the quote made me see. The waiting isn’t a strategy problem. I have the strategy. It isn’t a knowledge problem. I have the knowledge. It’s a comfort problem wearing the costume of a strategy problem.

Refining the plan one more time feels like work. It feels productive. But a lot of the time it’s just the most sophisticated way I’ve found to avoid the part that scares me. I’m not preparing. I’m negotiating. And comfort is patient enough to take the deal every single day.

The cure isn’t a better plan. I’ve got plans stacked to the ceiling. The cure is doing the uncomfortable thing before comfort gets to the table to make its offer.

So tonight, I did. I posted the first piece of promotion for my book — the one that’s been written and waiting since May. It took five minutes. It wasn’t perfect. Comfort had a dozen reasons for me to wait one more day, and every one of them sounded responsible.

I posted it anyway. Fifty-nine to go. The negotiation’s over.

The Only Way Out Is Through

~ David Willis ~ Leave a comment

7-40 Challenge | Rest Week

I wrote a song this week. It’s called “The Only Way Out Is Through,” and I didn’t set out to write a midpoint reflection on the year — but that’s what came out.

The verses are claustrophobic on purpose. Same four walls. Weight on the chest. A voice saying you’re not enough. That’s not a metaphor I had to reach for. That’s the inside of a lot of days this year — the ones where six out of seven habits was all I had, the deadlines I missed, the promotion I keep circling without walking into.

The chorus is the thing I keep relearning: there’s no way over it, no way around it. You can’t skip the hard middle of anything worth doing. You go through, or you don’t go.

I’m 175 days into this year. Halfway. And if I’m honest, the first half was mostly the verses — head down, knuckling up, counting to one and getting up again. Proving I could show up. Proving the engine runs.

But the bridge is where the song surprised me. I’d planned a song about endurance — hold the line, keep the grip, outlast the hard part. What came out instead was a moment where the hands give out and the rope goes slack, and the fall never comes. Where you stop holding and discover you didn’t have to.

That’s the part I didn’t plan. Halfway through this year, I’m starting to understand that “the only way out is through” was never just about gritting my teeth harder. Most of the getting-through hasn’t been me at all. The days I thought I was holding the rope, Someone has been holding me.

Here is the song:

The Only Way Out Is Through

The Dream You Never Actually Wanted

~ David Willis ~ Leave a comment

7-40 Challenge | Rest Week

I saw a quote today on social media. You’ve seen a version of it a hundred times: We only get one life. So why aren’t you running as hard as you can toward your wildest dreams?

It was attached to somebody’s website. There was a famous name stapled to it for credibility, and the guy delivering it had that urgency in his voice — the kind that exists to move you toward a buy button. I know that sound. I’ve studied it. And the moment I clock it, my guard goes up.

But here’s the thing that bugged me. Strip away the sales funnel, and the line underneath is still true. Our time is precious. We do only get the one. So why does the truth feel so cheap the second somebody uses it to sell me something?

I think it’s because they’re answering the wrong question. They’re handing you the answer — here’s what you should want, here’s how fast you should chase it — when the actual work is learning to ask a better question in the first place.

I’m not interested in finding “my own truth” the way the motivational crowd sells it — the version with a buy button attached. I want something harder. I want the truth about my situation.

Am I actually interested in this thing, or have I just been sold it? Am I talented at it, or am I pretending? What’s the real baseline of who I am and what I’m good at — not the version I’d like to post, the real one? Because until I can answer that, I can’t tell the difference between a dream and a fantasy.

A dream has legs. You can put a plan under it and walk toward it. I am never going to be a rock star — I don’t have the voice, the stage presence, or honestly the desire to grind it out. Do I ever picture myself singing to a stadium and selling a million albums? Sure. But that’s a fantasy. It collapses the second I’m honest about my talent, my time, and what I’m actually willing to do. The trouble is, most people name their fantasies as dreams, then stand in the mirror and beat themselves up for not reaching things they were never built to reach.

None of this works without a foundation of honesty. And I’m not writing it as someone who cracked the code and came down the mountain to hand it to you. I’m the lab rat. Every framework I build, I test on myself first, and I report back what actually happened — not what was supposed to happen.

So here’s my live example.

I started this year with the 7-40 challenge. One goal was to work out an hour a day, almost every day. And I found out something useful: I can do that. Reliably. I show up.

The scale, though, hasn’t moved the way I said I wanted it to. And the reason isn’t mysterious. I enjoy food. I set a range for myself and I’ve mostly lived at the top of it. The exercise is honest. The eating is honest. The goal was where I was lying.

Here’s where it gets interesting. Is there actually a gap?

If I’m enjoying food and holding steady — not gaining, just moving slowly — am I failing, or am I doing exactly what I want? That’s the question almost nobody asks. We assume the gap is real because we declared a goal once and haven’t hit it. But some gaps are imaginary. They only exist because we never honestly defined what we wanted in the first place.

When I’m truthful about it, here’s what I find: I’m choosing slower progress and more enjoyment over a faster, more miserable version. I’d rather not burn out. That’s a legitimate thing to want. But I have to name it — out loud, to myself — instead of pretending I’m chasing rapid results and quietly failing at them. The shame only shows up when I lie about what I’m actually after.

Once I named it, the gap closed. Not because anything about my body changed. Because I stopped measuring myself against a goal I never actually wanted.

A Good Goodbye

~ David Willis ~ Leave a comment

7-40 Challenge | Rest Week

Thirteen years ago, my grandmother was home, slowly waiting for the cancer to take her.

I knew she was near the end. She lived about an hour and a half away, so I called and asked if I could come early. I drove down, and that morning I cooked her breakfast. We sat across from each other and we talked — about my job, the master’s degree I was working on, my family.

I knew Grandmas aren’t supposed to play favorites. But she was proud of me, and I felt it.

I told her I loved her. I told her I was proud to be her grandson — proud to be working in the same business my grandfather had been in. I told her I wanted to make her proud.

She smiled and said I already had.

I knew, the whole time, that it would be our last conversation. And because I knew, I got to choose what kind of goodbye it would be. I wanted it to be a good one. It was.

There are only a few people in this life I miss the way I miss her. She gave the best hugs. She believed in me. She trusted me. And I didn’t let her down.

That morning gave me a clarity I’ve never forgotten. When you know the moment matters — when you know it’s the last one — everything unimportant falls away and you’re left with only the things worth saying. I love you. I’m proud of you. Thank you.

We don’t always get to know which conversation is the last one. That morning, I did. And I’ve tried ever since to talk to the people I love like I might not get another chance.

The Mush Was Mine

~ David Willis ~ Leave a comment

What a year of using AI badly taught me about communication

For the better part of a year, I used AI like a toy.

I asked it lazy questions. I watched it hand back mush. And I did what a lot of smart, skeptical people did around that time — I decided the whole thing was overhyped and went back to work.

Then one afternoon it occurred to me that the mush was mine.

The machine had been reflecting back, with uncomfortable precision, exactly how clearly I’d asked. Sloppy thinking in, sloppy answer out. When I finally got specific — when I said what I actually meant instead of what I half-meant — the thing got sharp. Genuinely sharp.

That was the moment the novelty wore off and something more useful took its place. Because what I’d run into wasn’t a technology problem. It was a communication problem. And it belonged to me.

The shortcut that isn’t

There’s an industry being built right now on the opposite premise.

You’ve seen the ads. A $27 PDF that promises AI will finally let you make the money you could never make without it. A quiz that “reveals” your hidden path. A download you can supposedly turn around and sell yourself — as if the file were the hard part.

Sit with that first promise for a second. If you didn’t know how to build something valuable before, a chatbot is not going to hand it to you. The tool amplifies what you already bring. It does not manufacture competence you don’t have. Selling people the fantasy that it does isn’t innovation. It’s the oldest grift in a new outfit.

The skill nobody’s selling

Here’s what AI actually rewards — the thing that doesn’t fit on a sales page:

The ability to say clearly what you mean.

That’s it. That’s the whole skill. Not prompt tricks. Not secret templates. The plain discipline of getting clear — first with yourself, then on the page — about what you’re actually trying to do. The machine just happens to be a brutally honest mirror for how well you’ve done it. It can’t read your tone. It can’t fill the gaps with goodwill the way a patient friend does. So when your request is vague, the vagueness comes right back at you, undisguised.

Most of us have never had to face that before. It’s bracing.

What twenty years in data taught me

I spent two decades working in data before any of this. And data work teaches you one law that turns out to explain almost everything:

If two people don’t agree on what a word means, every system built on it eventually breaks.

There’s a whole discipline devoted to fixing this. It’s called governance, and it is deeply unglamorous — mostly the patient work of defining terms, agreeing on what things mean, and refusing to let ambiguity slide. Skip it and your data is garbage no matter how powerful your tools are. Garbage in, garbage out — not because the system is broken, but because the meaning was never shared to begin with.

The same law governs your conversations with AI. And if you’re honest, it governs most of your conversations with people, too.

Same with a marriage. Same with your team on a Monday morning. When something “doesn’t get it,” the problem usually isn’t the other party. It’s that the meaning was never actually shared. We just don’t notice it with people, because feelings paper over the gaps. The machine offers no such mercy — which is exactly what makes it such a useful teacher.

Where I’ve landed

So here’s the conclusion I keep arriving at, and where I’m going to spend my writing for a while.

The most valuable skill in the age of AI is not technical. It’s the oldest one there is: the ability to mean something clearly, and to share that meaning so completely that another mind — human or machine — can act on it.

That can’t be sold for $27, because it isn’t a shortcut. It’s a practice. It’s slow at first and then it compounds. And it quietly makes you better at everything downstream — your work, your writing, your relationships, and yes, the tools.

I used AI badly for a year before I understood that. I’d rather you skip the year.