There’s a lot going on in an engineer’s day and in regular life, and something I hear often in conversations is:

“I need to be more organized.” “I need to be more disciplined.” “Once I get that sorted out, then I’ll start.”

And it makes sense.

These kinds of goals require sustained effort over time before the value shows up. Of course you’d want to feel confident the effort will compound. You do not want to start another thing and drop it. You do not want more evidence that you are inconsistent.

But where I see people get tripped up is that somewhere along the way, the goal quietly changes.

It moves from: “I want to learn this skill or build this thing.”
And it becomes: “I need to fix myself first.”

Now the project isn’t only a project. It’s a moral issue.

Before I can work on the project, I need to become more organized. Before I can learn the skill, I need to change how I function as a person.

All the effort that could have been going into the work now goes into becoming a different person.

That’s a tremendous amount of pressure. An impossible task.

The thought “I’m broken,” “something is wrong with me,” now becomes the gatekeeper of the goal.

So the goal doesn’t get worked on. The task has become too emotionally expensive to touch. And it gets dropped.

What I see open things up in the conversations I have is when a person notices what’s actually been happening.

They see they have not only been trying to work on their goal. They have been trying to redeem themselves. Trying to prove they are disciplined enough, organized enough, serious enough.

Once that becomes visible, something starts to shift.

All the effort that was going toward shame can be redirected toward the thing itself.

Because you don’t need to fix your entire life before you can work on something.

And once you remove the pressure to become a new person before you start... starting becomes a lot easier.

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He told me he needs to be more disciplined.

He wants to work on his own thing, but can never get focused.

He has ADHD.
He’s tried structuring his days.

Blocking time.
Scheduling deep work.

Even the idea of having someone check in on him.

“If I schedule it this week and have someone check in on me I’ll make a ton of progress!” he said confidently.

At some point he mentioned he gets distracted a lot.

So I asked him something simple.

Do you get distracted… or do you distract yourself?

He paused.
“I probably distract myself.”

“Why would you pull yourself away from work you say you want to do?”

We stayed there. And eventually something showed up.

There are people in his life who don’t really believe in what he’s trying to do.

They question it.
They don’t approve of it.
They don’t take it seriously.

And the distraction started to make a different kind of sense.

Because it’s not “just ADHD”.
(and it almost never is)

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“I’m doing a lot… but it’s not getting noticed.”
“Maybe I’m not doing the right things.”
“I don’t know what I’m missing.”

Thoughtful engineers doing solid work… but carrying a quiet, brooding sense of self-doubt.

Because the effort isn’t translating into reward.

The promotion is still elusive. Recognition from management? Silent.

And when effort doesn’t turn into visible progress… it’s hard not to make it mean something.

You start scanning yourself.

Maybe you’re not consistent enough.
Maybe you need to be more disciplined.
Maybe you need to try harder.

Or more insidiously: maybe you’re just not cut out for this.

So the mind gets busy trying to fix itself. Taking on more. Learning more. Looking for the missing piece that will finally make things click.

But sometimes what looks like a personal gap… isn’t.

In a recent conversation, an engineer was trying to figure out what he was missing. Why hasn’t he been promoted? What should he be doing differently?

But as he described the situation, something else came into view.

There was no clear path to promotion. No real criteria. No shared understanding of what “senior” even meant.

And more striking than that — there were few, if any, examples of people ever being promoted from within.

So while he was putting all the pressure on himself… it started to look like the system itself wasn’t set up to turn his effort into progress.

Nothing got solved in that conversation.
But something shifted.

The pressure to figure out himself loosened, just a little.

I Need a Better System

You’ve said it before.
Or if you’re being honest, you’ll admit that you probably say it all the time.

Sitting at your desk, staring at a ticket you’ve opened and closed four times without doing anything.

I just need a better system.

It sounds like a plan. It feels like taking responsibility. It offers a glimmer of hope.

But something about it never quite resolves. Because you’ve had that thought before. You found a system. It worked for a while (or at least you pretended it did). And then it didn’t.

And now you’re back here, having the same thought, wondering why you can’t just be productive.

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The System Finally “Works” (Until It Doesn’t)

I was speaking recently with a developer who had been living inside that loop for months.

He had read countless books.
Tried the notebooks, workflows, reminders…

And each time, something seemed to click. For a week or two the system seemed to be working.

But then it would stop.

I still haven’t found the right one!

And the relentless mission to find the right system would continue, along with an avalanche of pressure to figure it out already.

Meanwhile, the tickets piled up. Along with an overwhelming sense that things were slipping.

He felt broken in a specific way — like someone who was trying hard, doing everything right, and still couldn’t make the thing work.

So the explanation kept coming back to the same place.

I just need a better system.

The Part That Gets Missed

As we talked, I noticed a similar pattern.

The tickets weren’t being avoided because he has too many distractions, or doesn’t know how to plan his day.

They were ambiguous.

Too many open questions. Not enough information to know where to start. Problems that had already gone through several rounds of troubleshooting without resolution. Situations where it wasn’t even clear what done would look like.

When a task is ambiguous, the ADHD mind goes into freeze.

And when the mind is frozen long enough — when the same ticket sits untouched through enough mornings — the explanation stops being about the task.

It becomes about the person.

I should be able to figure this out. Something is wrong with me. I need a better system.

The system becomes the answer to a question that was never really about systems.

Pulling Up the Ticket

I asked him to pull up a ticket that was untouched.
And I asked him what felt hard about starting it.

He talked through it. The blockers. The open questions.

And at some point he stopped.

“I think I just need to follow up with one person to get clarity on their end.”
“I don’t have to fix the whole thing right now.”

I asked what he thought had just happened.

“I just talked through it with someone. And now it’s not so hard anymore”

I asked him if he’s ever noticed how often action follows conversation for him.

“That’s actually very normal for me.”

He’d been doing this for years.
But had never realized its impact.

It Was Never About Systems

The story he’d been carrying said the problem was a missing system.

That story had its own weight. Because if the problem was systems, the solution was discipline. Better planning. More consistency. Some version of himself that was more organized, more reliable, more able to just sit down and do the thing.

That version of himself had been the goal for a long time.

But what we had just watched told a different story.

The issue wasn’t a missing system.

The issue was that he never noticed how ambiguity leads to discomfort which leads to avoidance.
And how conversation reduces the discomfort of the ambiguity and prompts action.

Once the task left his head, the power of the ambiguity dissolved.

Along with the misdiagnosis of a better system.

What’s Actually Happening

This moment shows up constantly in my conversations with engineers.

A task sits on a board. Inside one mind, it accumulates weight — not because it’s impossible, but because it’s been alone in there too long.

Left alone with something ambiguous, the mind looks for an explanation.

Usually, the explanation it finds is itself.

But the moment the problem is spoken out loud — to a coworker, a manager, a partner, anyone willing to listen — its shape begins to change.

Not because someone else solved it.

But because ADHD minds don’t think clearly in silence. They think by talking.

And sometimes the only thing separating “this is impossible” from “here’s the next step” is a conversation.

Instead of a written issue this week, I wanted to share something a little different.

I was recently a guest on Attention Talk Radio with attention coach Jeff Copper. We had a wide-ranging conversation about ADHD and self-acceptance, what it really means and why it is often harder than it sounds.

You can listen to the full conversation here:

One theme that came up was the relationship between pressure and acceptance.

For a long time, I thought pressure was helpful.

But something I have noticed, both in myself and in people I work with, is that when pressure shows up we start moving very fast.

We go on autopilot and never slow down enough to actually understand what is going on. In the process, we lose ourselves.

At one point the conversation even wandered into Miles Davis and B.B. King, which turned out to be a surprisingly good metaphor for ADHD and self-acceptance.

I will let you hear that part for yourself.

We will return to our regular newsletter next week.

Warmly,
Michael

You’re the Only One, Right?

There’s a particular kind of loneliness in feeling like you are the only one who can’t just move forward.

Everyone else seems fine.
They’re shipping code, answering questions in standup, not visibly stuck.

But you’re stuck.

What exactly does “done” mean here?
How deep am I supposed to go?
What actually counts as success?

This is where a specific kind of self-judgment lives. A quiet judgment that just… shapes everything.

It turns nobody told me what’s expected here into everyone else figured it out and I didn’t.
It turns this is unclear into I am incompetent.

And so you stay quiet. You stay stuck.

And the thing that’s actually bothering you — the missing clarity, the undefined task, the expectations nobody spelled out — keeps affecting not only you, but oftentimes the whole team.

Instead of bringing your full thinking, your pattern recognition, your keen ability to notice what’s vague — you focus on compensating.

On blending in.
On not being the difficult one.
On not looking stupid.

The ambiguity stays in the room.

And your potential impact is muted.

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It Must Be Me

In a recent conversation I had with a newer engineer, this is exactly what was happening.

He had been assigned code reviews. No one had explained what a successful review looked like at his level. No one had told him how much time to spend, what the actual output should be, or what the point was for someone who couldn’t even push to main. He had five sitting in his queue. He wasn’t doing them.

He felt ashamed about it.

The kind that makes you hesitate before speaking in standup.
The kind that makes you assume your manager already sees the gap.
The kind that quietly predicts this is the ceiling of your capability.

And because the discomfort felt personal, he treated it as something to regulate internally rather than something to examine externally.

We worked on drafting a message to his manager. Not a confession of his mental state. Just clear, curious questions. What does a good review look like at my level? How much time am I supposed to spend on one? Should this take priority over my own tickets?

Not Just You

While we were working on it, he found out a senior colleague was experiencing the exact same confusion.

Not a junior. A senior engineer. Same team. Same reviews. Same fog.

That detail matters more than it might seem.

He had spent days treating his discomfort as evidence of a personal limitation. His need for clarity felt like a burden — something to manage internally, not surface externally. He assumed the ambiguity was bothering him because he’s broken, not because the expectations were actually unclear for everyone.

But the senior engineer wasn’t confused because of ADHD. He was confused because nobody had defined this process clearly.

The ambiguity was real. It was just that one person felt it first, felt it most acutely, and interpreted that as a personal failing rather than useful signal.

This is a pattern I’ve seen many times. Some people tolerate vagueness longer. Some feel it immediately. Neither response makes the ambiguity disappear.

The Impact You Don’t Have

When confusion gets internalized as defect, two things happen.

1. You lose energy managing yourself — trying to be less needy, less sensitive, less bothered.

2. And then, the team loses the signal you were about to surface.

The cost isn’t just the anxiety you carry.
It’s the clarity no one receives.

And it’s the impact you don’t get to have.

Because instead of being the engineer who sharpens expectations, who tightens processes, who names what others are skimming past — you become the engineer quietly compensating for something that was never actually yours to compensate for.

Your sensitivity to ambiguity isn’t what limits you.

Internalizing it does.

“I’ll just figure it out.”

It sounds confident.

Sometimes it even feels responsible.

You say it after a meeting where something didn’t fully make sense. Or while reviewing a ticket that feels half-specified — one key detail missing, one edge case undefined.

No one else asked a question.

Everyone seemed fine.

So you decide you’ll handle it.

You’ll just figure it out.

And the next thought follows almost immediately:

“I just need to think about it more.”

That sounds mature. Measured. Professional.

You don’t want to ask something half-formed. You don’t want to slow the room down. You don’t want to expose confusion that “shouldn’t” be there at your level.

So you tell yourself you’ll think first.

Then speak.

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When Ambiguity Meets ADHD

But here’s what’s actually happening.

Something was ambiguous.

With ADHD, ambiguity doesn’t sit quietly. It overwhelms.

ADHD is defined by limits in working memory and regulation. When the problem is concrete, that system works well. When things are unclear, your mind doesn’t settle. It just spins.

Working memory now has to hold context, assumptions, constraints, and open questions all at once. Without structure, nothing anchors. The problem doesn’t lock in.

Instead of clarity, you feel strain.

But you try to resolve it internally.
Because nobody else seemed bothered.
And why should you need more than others?

So you replay the meeting. You reread the ticket. You simulate outcomes. You try to narrow it down on your own.

But without conversation, the space doesn’t narrow.

It just stays open.

And “thinking about it” isn’t a concrete task. There’s no clear first move. No output. No signal that you’re getting closer.

So the strain lingers.

Sometimes you’ll even tell yourself:

“I’ll talk to someone once I’ve thought about it more — so I have something tangible to discuss.”

That sounds responsible. But it’s actually backward.
You’re waiting for clarity that won’t arrive on its own.

Because ADHD thinking stabilizes through externalization.

Clarity doesn’t form privately and then get expressed.
It forms when ambiguity is spoken through.

Private Weight

So you pivot.

You switch to something smaller. Something defined. Something that gives you traction.

You aren’t consciously avoiding the work.
You tell yourself you’ll come back once you’ve “really thought about it.”

But you don’t.

A day passes. Then another.
And now you’re behind.

The task that once felt unclear now feels threatening.

Why am I not making progress? This shouldn’t be this hard.

The ambiguity hasn’t resolved. It has multiplied.

When Consequences Appear

The delay becomes visible.

Someone asks for an update.

You rush and implement based on a guess.

Tests fail.

A reviewer points out a misunderstanding.

Now there are consequences.

And those consequences feel like confirmation.

See? I’m not competent. I’m not operating at the level I should be. I’m falling behind.

But that wasn’t the starting point.
The starting point was ambiguity interacting with ADHD — kept private.

When Load Turns Into Identity

By the time judgment shows up, the earlier steps are invisible.

Your brain compresses the chain. It jumps from consequence straight to identity.

“I should have known.”
“I’m not as sharp as I thought.”

The beginning disappears.

It didn’t start with incompetence.
It started with ambiguity being held privately in a brain that doesn’t stabilize ambiguity alone.

What Changes When It’s Spoken

When something unclear is said out loud, it gets narrowed. Structured. Reflected back. The cognitive load drops.

If you wait to speak until you’ve already clarified it alone, you may wait indefinitely.

From the outside, staying silent looks like independence.

Internally, it’s a brain trying to carry more than it’s built to hold.

Nothing dramatic happened.
Just a small question that never made it into the room.

And everything that followed.

The pattern is visible now. That changes what’s possible.

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There’s a sentence I hear often, usually said with a mix of frustration and self-criticism:

“I just need better accountability.”

On the surface, “accountability” sounds reasonable. Responsible. Adult.
Like the missing ingredient between knowing what to do and actually doing it.

But when we slow the moment down, something else is usually happening.

Slowing the Moment Down

Picture the scene.

You’re staring at a task you genuinely care about. It’s not meaningless. It’s not beneath you.

It’s just… quiet.

No deadline breathing down your neck.
No one asking for an update.
No meeting forcing you to explain what you’ve been thinking.

Just you, the task, and a vague sense that you should be able to start.

This is usually where the inner commentary begins.

“If I were more disciplined, this wouldn’t be a problem.”
“Other people don’t need someone watching them.”
“Why can’t I just be independent?”

So the conclusion forms quickly:

What’s missing is accountability. Pressure. Consequences.
Something external to make this feel real.

Where Self-Judgment Sneaks In

Here’s the subtle shift that’s easy to miss.

The moment execution stalls, the explanation doesn’t land on the task.
It lands on you.

Needing accountability quietly becomes evidence of a flaw. You are incompetent and you lack discipline.

And once it’s framed that way, the problem is no longer:

“How does my mind engage with work?”

It becomes:
“What’s wrong with me that I need a babysitter?”

So you try to manufacture accountability. Tighter plans, stronger promises, more internal pressure.

But when that still doesn’t work, the judgment just sharpens.

What’s Actually Missing

In many real conversations I’ve been part of, the shift doesn’t come from stricter accountability at all.

It comes from another human entering the room.

Not to monitor.
Not to evaluate or enforce consequences.

Just to be there.

Something changes the moment thoughts are spoken out loud. When half-formed ideas have somewhere to land. When the task is no longer held entirely inside one person’s head, or in a poorly written ticket.

Often, the person will say something like: “I didn’t realize that was the part I was stuck on until I said it.”

Nothing magical happened. No discipline suddenly appeared. No motivation hack kicked in.
What changed was the cognitive load and the isolation.

The work became socially real.

This isn’t about accountability.
It’s about how some minds regulate attention, clarity, and momentum.

For the ADHD brain, thinking is not a silent, internal act. It’s relational. It stabilizes when shared, and it feels good to be with others.

That doesn’t mean you can’t work alone. It means working alone often costs more than you realize.

“Accountability” Is Often a Misdiagnosis

Imagine two very different check-ins with your manager.

In the first, your manager asynchronously sends you a list of tasks each Monday and asks you for a report each Friday on what you finished.

Clear tasks, clear expectations, and clear deliverables.

In the second scenario, each Monday the manager has a 45‑minute phone call.

“Hey — what are you working on lately?”

No strict agenda.
No checklist.
Just an informal conversation.

That first sounds like real accountability. Just what you need, right?

But which do you think would actually be more helpful for your productivity?
Be honest…

Not the task list. The conversation.

Not because the tasks wouldn’t help. But because the informal meeting would force something else to happen first.

You have to talk. Ask questions. Sort your thoughts out in real time.

The work doesn’t become clearer because someone assigned it. It becomes clearer because it was spoken.

That moment matters.

Because on paper, the task list looks like accountability and the conversation looks like fluff. But for some minds, it’s the conversation that does the real work.

Naming the Cost

When this gets mislabeled as an accountability problem, the cost compounds quietly.

You don’t just feel stuck. You start to distrust yourself.

You stop asking for the kind of support that would actually help, because you believe needing it means something about your worth.

So you wait for urgency instead.

Deadlines, consequences and crisis do often create focus — but at a price. Over time, the pattern teaches a harsh lesson: “I only function under pressure.”

But the moment was never asking for discipline. It was asking for connection.

A Different Way to See the Moment

If you zoom out just slightly, this reframes the whole experience.

Needing another person nearby doesn’t mean you’re irresponsible. It means your mind clarifies in relationship.

Wanting to talk something through before acting isn’t childish or needy. It’s how ambiguity dissolves.

Struggling alone doesn’t make you strong. It often just makes things heavier than they need to be.

Not everything that looks like a discipline problem is one.

Sometimes, it’s just a human one.

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The Task That Never Asked to Be a Judgment

There’s a moment that often starts quietly:

Why can’t I just start this task?

Nothing is on fire yet.
No one is waiting.
No feedback has landed.

Just a task sitting there in your ticketing system.

If the task could speak, it would say:

Hi! I am three sentences without any acceptance criteria.

That’s all.
No insult.
No commentary.

But the mind doesn’t stay with that for long.

Your Response

Comparison slips in almost immediately:

Everyone else seems able to do this type of task.

Now the task isn’t just a task anymore.
It’s evidence.

The task responds, plainly:

Some people are more comfortable making starting assumptions.

Still neutral.
Still descriptive.

But something has already shifted.

Your question now changes:

So what does that say about my worth?

This is the pivot point.

The task hasn’t become clearer.

But the meaning attached to being stuck has.

Where self-judgment sneaks in

The lack of movement starts to feel like a verdict.

The task says back to you:

No, this says nothing about your worth.

But that answer doesn’t land.

Because the mind is no longer focused on this individual task.
It’s focused on identity.

So the mind escalates:

No, it means I am an incompetent failure.

And the task replies, almost confused:

I never said that.

This is the quiet rupture.

The task didn’t accuse you.
The task didn’t generalize.
The task didn’t make it personal.

But the judgment arrived to explain the discomfort of not knowing how to start.

What’s actually happening here

In real coaching conversations, this moment usually isn’t about motivation.

It’s about ambiguity.

Navigating ambiguity is painful for the ADHD mind.

But in the moment, the mind is not aware of that.
All the mind knows is that it is experiencing the discomfort of not knowing.

And when that discomfort becomes unbearable, the mind looks for relief.

And the self-judgment offers a strange kind of relief.

“I am bad” is painful — but it’s clean.

It gives the mind something solid to hold onto when uncertainty feels intolerable.

What changes when this is noticed

Nothing magically gets easier.

The task is still underspecified.
The acceptance criteria are still missing.

But something important separates.

Instead of the mind jumping to:

What’s wrong with me?

There’s room for:

What is unclear about this task?

Who can I talk this out with?

What starting assumptions can I make?

The pressure drops just enough for the self-attack to stop escalating.

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“I only seem to function when everything is on fire.”

This is a sentence I hear often — sometimes said with frustration, sometimes with dark humor, sometimes almost with pride:

It usually comes after someone describes weeks of stalled progress… followed by a frantic push right be

fore a deadline.
Or after they admit they’ve been avoiding something important — until the consequences became impossible to ignore.

What’s striking isn’t just how common this moment is.
It’s how coherent it feels from the inside.

“That’s just how I work best.”

When everything is on fire, things finally seem to make sense.

Slowing the moment down

Before the fire, the task feels… fuzzy.

There are too many options.
Too many interpretations of what “done” could mean.
Too many paths that might be right.

So the mind circles.
Planning feels safer than committing.
Thinking feels productive — even when nothing is moving.

Then something shifts.

A deadline becomes real.
A consequence becomes unavoidable.
A decision is no longer theoretical.

And suddenly:

• The problem narrows

• The noise drops

• The next action becomes obvious

Not because you suddenly gained discipline —
but because the ambiguity collapsed.

In crisis, the world shrinks to what matters right now.

And for an ADHD brain, that clarity can feel like oxygen.

Where self-judgment sneaks in

Here’s where the story often turns harsh.

After the crisis passes — after the work gets done — a different voice shows up:

“Why can’t I work like this all the time?”
“What’s wrong with me that I need pressure just to function?”
“Other people don’t need everything to be urgent.”

The focus gets attributed to the fire itself.

So the conclusion becomes:

“I guess I just need chaos to perform.”

That interpretation sticks. And it quietly reshapes identity.

Not as someone who struggles with ambiguity,
but as someone who only works when things are burning.

And that’s a heavy label to carry.

What’s actually happening (without fixing it)

In the conversations I have, the fire isn’t doing the magic.

What changes in crisis isn’t motivation — it’s clarity.

• Fewer choices

• Less room for perfection

• Clearer constraints

• Immediate feedback

The task stops being abstract and becomes concrete.

There’s no longer time to wonder if you’re doing it “the best way.”
You just do a way.

That’s not dysfunction.
That’s your brain responding to clarity.

The cost to relying on the first isn’t obvious at first — because the urgency seems to works.
But it extracts payment later: exhaustion, resentment, recovery time, shame.

And often a quiet fear:
“If I don’t create pressure, nothing moves.”

What changes when this is noticed

Something subtle shifts when this moment is seen clearly.

Instead of asking,
“How do I force myself to work without a crisis?”

The question becomes gentler — and more accurate:

“What disappears for me when urgency shows up?”

The answer is rarely “laziness.”
It’s usually uncertainty. Or overwhelm. Or too many open loops.

Seeing that doesn’t solve the pattern.
But it loosens the self-attack.

And that matters — because shame makes everything heavier, not clearer.

When people notice this distinction, they often stop glorifying the fire…
and stop condemning themselves for needing it.

They begin to see the pattern as information — not a character flaw.

A quiet place to leave this

If you recognize yourself here, you’re not broken.

You’re responding to a world that often asks you to operate without enough clarity, certainty, or boundaries.

Crisis didn’t give you superpowers.
It just removed what was in the way.

And noticing that — without rushing to fix it — is often the first moment where something else becomes possible.

Not ease.
Not discipline.

Just a little more understanding of how your mind actually works.

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Over the past year, I’ve had dozens of conversations with thoughtful, capable software engineers with ADHD. Different roles, different companies.

But I noticed that the same pattern keeps showing up.

Something goes off.
A task slips.
A moment doesn’t go the way it should.

And even after the situation is dealt with, the hardest part sticks around.

“The worst part isn’t the mistake — it’s how much I can’t stop hating myself afterward.”

That’s the moment this newsletter is about.

ADHD isn’t just a productivity problem.
It’s often a relationship-with-self problem, especially at work.

Each week, I explore one real ADHD-at-work moment from the inside:

• where shame shows up,

• where clarity drops,

• and where execution quietly gets harder — not because of the work, but because of what’s happening internally.

We won’t focus on tips, hacks, or advice.
Because you’ve tried them all already, and if they worked, you wouldn’t be here.

Instead, we slow the moment down — especially the part most advice skips — and look at what happens when the self-attack isn’t driving everything.

— Michael

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