#119 📝 Why Your To-Do List Never Gets Started

When having everything written down makes you more stuck, not less

Welcome to Tech Atypically 👋, your weekly blog for navigating the challenges of ADHD and being in the tech industry.

I am an ADHD and product management coach, helping you change one belief and take one action each week.

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🦋 The Takeaways

Belief: I can’t start until I’m prepared for everything.

Reality: Perfectionism creates paralysis—this is a freeze response, not a planning problem.

Action: Externalize the mess, work backwards from your goal, and focus on “who” not “how.”

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⭐️ Introduction

I’m back after two weeks in Thailand with my mom. It was a great trip, and I got to spend time with her in ways I’ll remember for the rest of my life.

If there’s something you’ve been meaning to tell or do with a loved one, do it now. I wish I had done this trip sooner, before Alzheimer’s took more of her.

Back to our regularly scheduled program…

Welcome to part 15 of the Inclusive Performance Coaching Series, where I explore topics that help you improve your work performance in ways that work for your brain. This week: Why Your To-Do List Never Gets Started.

Someone I’m coaching just started a new role. Day one, they got a clear list: people to meet, relationships to build, a project to develop, a strategy to create. Everything was laid out and ready to go.

Instead, they’re frozen.

They’re paralyzed going into meetings because they need to prepare for every single eventuality. They consider all the possible questions, all the scenarios, all the ways things could go. This is how I define anxiety. And because they can’t prepare for everything, they don’t prepare at all.

They have a to-do list. They know what needs to happen. But they can’t start.

This isn’t a planning problem. This is something deeper. I’m joined by my partner coaches Rupert Dallas and Michael Asaku-Yeboah to discuss this common challenge for ADHD folks and how to overcome it.

I struggle with anxiety every day. It’s not the someone is going to get me kind. It’s the kind that says I’m going to fail no matter what I try. For me, it stems from my self-loathing and ADHD.

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😰 The Belief - I Can’t Start Until I’m Prepared for Everything

The pattern of anxiety looks like this:

You have a meeting coming up. You start considering all the possible questions, scenarios, and ways things could go. What questions might they ask? What if they ask about X? Or Y? Or Z?

The list of possibilities grows. Soon you’re thinking: “I don’t know what to prepare for because I need to prepare for everything.”

And because you can’t prepare for everything, you prepare for nothing.

Or you have a project to start. You look at your to-do list and your anxiety spirals through all the possibilities: “There are so many things. If I start on one thing for five minutes, then jump to the next thing for five minutes, I’ll never complete anything. So I better not start until I know the right order, the right approach, the complete plan.”

The belief is: I can’t start until I have perfect clarity and preparation.

But that clarity never comes. The anxiety keeps spinning through possibilities. So you stay stuck.

You believe you’re screwed, so why bother taking action if it all leads to the same result?

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🤝 The Reality - Anxiety Becomes Freeze Response

This thought process is anxiety turning into a trauma response. Michael explains: “Trauma responses are fight, flight, freeze, or fawn.”

When you need everything to be perfect before you start, and that need for perfection prevents you from starting at all—that’s freeze. Your nervous system is using anxiety (constantly spinning through all possible scenarios) to protect you from the risk of failure by preventing you from trying. It’s not laziness. It’s not poor planning. It’s your body trying to keep you safe.

Here’s what makes this so cruel: the very thing you think will protect you is what’s keeping you stuck. You think if you’re prepared for everything, you won’t fail. But the standard of “everything” is impossible to meet. Your anxiety keeps finding new scenarios to prepare for. So you never start. Which means you definitely won’t succeed.

Michael’s first question when someone is stuck reveals another layer: “Is everything they need to do in their head? Because if it’s in their head, it’s going to be difficult to work through. It’s going to be convoluted.”

When your to-do list lives only in your mind, the anxiety compounds. Every task connects to ten other tasks. Every scenario branches into more scenarios. Everything feels urgent and impossible at the same time.

The freeze deepens because you can’t see the actual shape of what you need to do—it’s all just a swirling mass of anxiety.

Anxiety is feeling like you’re broken and failed before you even start.

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🛠️ The Action - Break the Freeze Response

So how do you actually break through this? Michael and Rupert helped me see that it’s not about planning better—it’s about getting unstuck from the anxiety-driven freeze response.

1. Externalize Everything and Accept the Mess

First, you need to get everything out of your head and make it visible. When it’s all in your head, the anxiety keeps spinning through infinite possibilities. Michael recommends creating what he calls a “criminal mind board”—like a detective solving a case.

Map out the people you need to connect with, what they do, and what their expertise is. List all your tasks somewhere you can see them. Don’t worry about order yet. Just get them out.

But here’s the crucial part that most people miss: accept that the beginning is going to be messy. Michael emphasizes: “The beginning is going to be messy. It’s going to be all over the place. But if you’re able to stay the course and do some of this organization, it’s going to help. Where you need to do a lot of work is helping them understand that the beginning is going to be messy.”

The mess is not a sign you’re doing it wrong—the mess is part of the process. Michael describes it like a jigsaw puzzle: you pick a piece, see if it fits. If not, put it in the parking lot so you know it’s there and you can come back for it. Slowly it begins to take shape.

The clarity comes through action, not before it. Your anxiety wants you to have all the clarity before you start. But that’s backwards.

2. Work Backwards from the Goal

Once you’ve externalized everything, work backwards from the goal instead of getting lost in the anxiety of all the steps forward.

Michael suggests: “What is the goal you’ve been given? What would getting closer to that goal look like? What would be the next step before that?” Build backwards from the goal to where you are so the path becomes visible.

For the person I’m coaching, the goal is successful onboarding and project execution.

Working backwards: What does successful project execution look like? What needs to happen before that? What relationships need to be built? Who are the key stakeholders? What are the first conversations?

This approach cuts through the anxiety because you’re not trying to anticipate every possible scenario. You’re just identifying what needs to happen to reach the goal.

3. Focus on “Who” Not “How”

Recently, I learned this lesson myself. I was working with my ADHD coach on a business idea for commercial real estate. I told him: “I need to have a business plan before I meet with a real estate agent.”

My anxiety was spinning: What should be in the business plan? What format? What level of detail? What projections? What if they ask about X, Y, or Z?

His response changed everything: “Do you? I don’t think you do. Your job isn’t to figure out what the real estate agent wants. Just find a real estate agent and ask: ‘Do I need a business plan to start working with you?’ You’ll find out very quickly what you need to do.”

It’s about who, not how.

Stop trying to figure everything out alone. Your anxiety wants you to prepare for every eventuality. But your job isn’t to prepare for every eventuality. Your job is to identify who can help and ask them.

For meeting prep, you don’t need to anticipate every possible question. You need to know who will be there, what their role is, and what outcome you’re driving toward. The rest you figure out together in the meeting.

I have to constantly remind myself: I’m not doing this alone. I have a Michael. I have a Rupert. I just have to ask. You’re not doing this alone either.

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✨ Conclusion

When your to-do list never gets started, the problem isn’t the list. It’s the anxiety-driven belief that you need to be perfectly prepared before you begin.

That anxiety turns into a freeze response—your nervous system is trying to protect you from failure by preventing you from trying. But the cost of that protection is staying stuck.

The solution isn’t better planning or trying to control every scenario. It’s externalizing the mess, accepting that beginnings are chaotic, working backwards from your goal, and remembering you don’t have to figure everything out alone.

Start messy. Start imperfect. Just start.

And eventually you’ll get it done. Even if it didn’t go to plan. Screw the plan.

Just like I did today after starting this article 3 weeks ago…

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⏭️ Next Week

Ending the inclusive performance series.

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