Why Rest Is Hard (And Why It Has to Happen Anyway)

7-40 Challenge | Planning Week, Day 3

Yesterday I had plans. I was going to grab a cup of coffee, sit in the shop for a while, and think. Instead, I fell asleep for an hour and a half.

When I woke up, I was frustrated. I’d lost time. The thinking I wanted to do didn’t happen. The coffee didn’t happen. The afternoon was already sliding sideways.

But here’s the thing I had to sit with: any thinking I would have done would have been undercut by the fact that I still needed more sleep. My body made the call my brain wouldn’t.


I called Round 3 three days early. Not because I failed — I delivered everything on my lock list — but because I was running on fumes and I knew it. I could feel it in my writing. I can look back at certain posts from the last two weeks and tell you exactly which ones were written when I was sharp and which ones were written when I was just trying to get something across the finish line.

That’s not the standard I want.


Here’s what makes rest hard for me. It’s not that I think rest is weakness. I don’t. But inaction has a cost. Things don’t get done. Momentum stalls. And old habits — the ones I’ve spent 137 days replacing — don’t need much of an invitation to creep back in.

Rest feels like opening the door to backsliding.

I’ve spent most of my adult life in a corporate world where there’s always another thing to do, always another deliverable, always a reason to keep pushing. You get a limited number of weeks off, and you learn to treat downtime as something you earn in small doses, not something you build into the structure.

So even when I build flexibility into my own system — and I did, from Day 1 — using it still feels like I’m getting away with something.


But here’s what I know now that I didn’t fully feel five months ago: the most productive year of my life is going to require the most discipline about rest.

Not discipline about pushing harder. Discipline about stopping.

If I want to reach the people I’m trying to reach, if I want the writing to be sharp and the ideas to land, I can’t be the guy grinding out a blog post at 11 PM with nothing left in the tank. That’s not documentation. That’s just stubbornness.


So Round 4 is going to look different. Not in what I do — the seven habits aren’t changing — but in when I do them.

Bible study and BiblePictures365 go first thing in the morning. Walking happens before lunch, every day. Reading rides with the walk. Gratitude goes early, because starting the day grateful changes the shape of everything after it.

That leaves the afternoon and evening for creative work — writing, music, strategy — in shorter, cleaner windows. I’ll still be in the gym with Trey three nights a week from nine to ten. And after that, I’m done. No heavy thinking after the gym. No trying to squeeze one more thing out of a brain that’s already checked out for the night.

The goal isn’t to do less. It’s to stop pretending I can do everything at any hour and have it all come out at the same level.


I built this system to fight backsliding. Every habit, every streak, every daily post — all of it exists because I know what happens when I stop paying attention.

Now I have to trust that system enough to step back from it. That might be the hardest habit of all.

Forward

I’m in the planning week between rounds of my year-long challenge. I called Round 3 early. I’m supposed to be resting.

I wrote a song today anyway.

Some creative work feels like work. This one didn’t. It came out of me the way songs used to come out when I was younger and thought I had something to prove. The form is exactly the kind of motivational rock anthem I told someone earlier this week is my favorite kind of music — the kind that turns struggle into propulsion.

I think the song wrote itself because the truth underneath it is what I needed to hear today.

Not push harder. Not do more.

Just forward.

One direction, no specific pace. Forward through the rest week. Forward into Round 4. Forward through the parts of the year that haven’t gone the way I planned. Forward through the work that’s still ahead.

Here’s the lyric.


FORWARD

Words by David Willis. Music arranged with Suno.

When I found my voice, I gave it everything I had
Stepped on that stage, killed the set, they still said nah, not enough, kid
Rolled home with that sting in my chest, eyes wide, no sleep for a week straight
Then the voice in my head hit replay: you’ll never be enough, just quit, it’s too late

Been down here before, I know this floor
But something’s rising and I want it more

Forward — didn’t come this far to fall
Forward — bring it on, I’ll take it all
Forward — every scar on my chest
Forward — it’s just proof that I haven’t quit
Keep moving forward

They called me up, said sorry man, we gotta let you go
Held my head high, swallowed the pride, didn’t let the frustration show
Then the phone rang with a call I never saw coming through
Sometimes what we pray for is waiting on the other side of the wreck we just went through

Been down here before, I know this floor
But something’s rising and I want it more

Forward — didn’t come this far to fall
Forward — bring it on, I’ll take it all
Forward — every scar on my chest
Forward — it’s just proof that I haven’t quit
Keep moving forward

Too many voices screaming, too many hands dragging me down
The noise gets crushing, violent, I can barely stay above the sound
But I see their faces breaking through the storm — I know why I’m here
I’m fighting like mad for them, and I’m not done, not while I’m still here

Forward — didn’t come this far to fall
Forward — bring it on, we’ll take it all
Forward — every scar on our chest
Forward — it’s just proof that we haven’t quit
Keep moving forward

Forward… (forward…)
Forward… (one more time…)
Keep moving forward…


The pronoun shift in the last chorus isn’t a typo. My chest turned into our chest somewhere in the bridge, when I saw the people I’m doing all of this for. That shift is most of the reason the song exists.

Forward. One more time.

Tonight (and Everyday) I’m Grateful for My Wife

I scrolled past a video the other day that I can’t even find again. It was a husband and a wife. They had been in some kind of fight. The husband offered an olive branch. The wife took it. There were no theatrics. Just two people who clearly respected each other and clearly loved each other, working through something instead of around it.

It hit me harder than it should have for a video I can’t remember the source of.

That’s the relationship I have with my wife.

I’m not the perfect husband. I am, however, a good husband, and I love her on purpose. But I stick my foot in my mouth more often than I’d like. I don’t always communicate the way she deserves. There are days I get it right and days I don’t, but I am right where I always want to be. With her.

She loves me through all of it.

Twenty-seven years of choosing each other on purpose. Twenty-seven years of olive branches offered and taken. Twenty-seven years of two imperfect people deciding, quietly and daily, that the relationship is worth the work.

Anytime I see a love story, I think of her. She is the other side of mine.

Tonight I’m just grateful.

The Drift: How Some Relationships Die Quietly

I have watched partnerships I didn’t think would end, end.

Not in dramatic blowups. No financial scandal. No moment where an outsider could point and say that’s where it broke. Just a slow erosion of what made the partnership work, until something tested it and it couldn’t hold the weight.

The drift is what I want to talk about.

The Brittle Partnership

The partnerships that ended without warning weren’t actually ending without warning. They had been drifting for months or years. The two parties inside them had stopped sharing the same priorities, the same focus, the same understanding of what they were building together. They could still navigate the routine. They could still cooperate on deliverables and meetings and the calendar. But underneath the routine, the structural alignment had thinned.

The problem with thin structural alignment is that it works fine until it doesn’t.

When a stress test came — a market shift, a budget cut, a personnel change, a strategic pivot — the partnership had no reserves to draw on. What looked like a working relationship for years turned brittle in a moment. It busted apart not because something dramatic happened to it, but because nothing dramatic had been happening to it for a long time, and the silence had hollowed it out from the inside.

That’s the pattern I keep seeing. Not catastrophe. Erosion that produces the appearance of catastrophe when conditions finally test what’s left.

The same pattern shows up everywhere two parties have to keep agreeing about something over time — business partnerships, team relationships, vendor relationships, board dynamics, even working friendships at the office. The tell is usually the same. The work that used to feel collaborative starts feeling transactional. The meetings that used to produce ideas start producing reports. The trust that used to make decisions easy quietly drains, and nobody quite remembers when it left.

What I Got Wrong

More than ten years ago I left my first data career and joined a new company. I came in with eagerness and gusto. I had ideas. I had seen things at the previous job I knew could be improved. I wanted to build alignment and change the organization for the better.

I put people off.

Not because the ideas were bad. Because I came in trying to renegotiate things I had no standing to renegotiate yet. I hadn’t gotten to know the people. I hadn’t understood why the existing approach existed. I hadn’t earned the right to propose a new direction. I was trying to fix what looked like drift to me when, from the inside, it didn’t look like drift at all — it looked like the way they had always done things.

What changed me was the slow realization that the desire to make things better had to start with the desire to build relationships first. I started finding people where they were. I started asking what they needed from me before telling them what I thought they needed. The respect and the trust I eventually earned came from listening before negotiating, and once that trust was there, the conversations about what to change became conversations we could actually have.

I learned to renegotiate by first learning that you don’t get to renegotiate from outside the relationship.

How the Conversation Actually Goes

When a partnership has drifted and someone has noticed, the question is how to open the conversation without it landing as an accusation.

The mechanic that works for me is to whittle down from where agreement still exists to where it doesn’t. Do we still agree on the mission? If yes — do we still agree on the approach? If yes — do we still agree on the methods? You walk down the levels until you find the place where the agreement has actually shifted. Then you start the real conversation there.

That move does two things. It establishes that you’re not attacking the whole partnership — there’s plenty you still see the same way. And it locates the divergence specifically, instead of letting it remain a vague we’ve grown apart. Vague drift is hard to address. Specific divergence is something two parties can actually talk about.

The other piece is posture. If you were equals in the partnership and you’re now asking to renegotiate, you have to address each other as equals. Give space to explain thinking. Sometimes follow the other party’s lead. What you’re really saying when you renegotiate is that you value the relationship and the outcome more than you value controlling the method. If that’s true, the conversation is already most of the way home.

When Silence Is the Right Choice

Not every drift needs to be addressed. Not every partnership is meant to last forever.

I’ve been part of working relationships that lasted exactly as long as they should have. Two people put together by circumstance, did good work for a season, and then the season ended. I left that company more than ten years ago and a handful of those colleagues have stayed in my life. Most haven’t. The ones who haven’t aren’t a failure — they’re a chapter that closed cleanly. We did what we were brought together to do, and we moved on.

The mature version of letting go isn’t bitterness. It’s gratitude. You made an impact on my work. I’m grateful for what we built. If our paths separate from here, I’m rooting for you. If I can ever be useful to you, I want to be. That’s how you honor a partnership that’s reached its natural end.

The trick is reading which kind of drift you’re in. Some drift is the partnership telling you it’s complete. Some drift is the partnership telling you it needs renewal. Both are valid outcomes. Neither is failure. But the responses are opposite, and the cost of getting it wrong is high in either direction — fighting to renew something that’s done, or releasing something that just needed attention.

The test I run is one question: Is there still something here both parties would grieve losing? If the answer is yes, the drift is asking for renewal. If the answer is honestly no — not bitterly, just no — the drift is telling you the chapter is finished, and the cleanest move is to let it finish.

The Hardest Failure Mode

The corruption pattern in most drifting partnerships isn’t lack of conversation. It’s lack of the right conversation.

Two parties can talk every week and still be silent about everything that matters. Status updates, deliverables, the weather of the calendar — all of it traffic, none of it the actual partnership. The structural conversation, the how are we doing, where are we headed, what’s changed since we last checked conversation, the one that requires both parties to be honest about what they’ve been carrying — that’s the conversation that goes missing first.

I’ve watched partnerships die quietly because of this. Two people who started with shared goals, drifted through one or two strategic shifts without ever naming the divergence, and woke up a year later running tactics on each other inside what they still called a partnership. Neither of them was acting in bad faith. They had just stopped having the conversation that would have caught the drift, and by the time the conditions tested them, there was nothing left to test.

That’s the cost of letting the structural conversation lapse. Not betrayal. Just the slow accumulation of conversations that didn’t happen, until the partnership couldn’t carry the weight conditions eventually placed on it.

The Small Days

The partnerships that don’t drift aren’t drifting less because the parties got lucky. They’re drifting less because of what’s happening on the small days — the days that don’t feel like they matter, the conversations that don’t feel important enough to bother with, the noticing that happens when nothing is wrong.

That’s where the structural alignment is built. Not in the crisis. Not in the quarterly review. In the Tuesday afternoon question that gets asked before there’s a reason to ask it.

You can’t outrun drift with effort applied at the wrong layer. You have to do the small work, on the small days, before the stress test arrives.

That’s all there is, really. The conversations that happen, or the conversations that don’t.