Even I Get Overwhelmed (and What I Do About It)
Aug 20, 2025Saturday morning hit me like a brick.
I woke up with a pit in my stomach, staring down more to do than I had time to do it. Sunday night I would be boarding a plane for our first international speaking opportunity for Time Boss, which meant even less time for the things that mattered most.
Fear showed up fast. For me, it sounded like this: if I don’t finish these tasks, it will hurt me or someone I care about. That fear kicks me into FIGHT or FLIGHT mode, and neither path leads to peace.
10 years ago I would have done one of two things:
- FIGHT = Grind - Stay up late, wake up early, skip workouts, skip lunch, anything to get more time to get through the list. Will I check things off? Certainly, but I don't solve the root cause of more to do than time to do it.
- FLIGHT = Checkout - Ice cream, alcohol, Netflix (maybe all three!). Anything to get out of my head for a bit and not feel overwhelmed, but certainly it doesn't solve the problem.
Gratefully I now know the Time Boss Weekly Framework, and I'm never an hour away from decreasing my overwhelm, and increasing my clarity and commitment to my goals and values.
Here's what I did:
How to Reduce Overwhelm From Your Task List
Whenever I feel overwhelm creeping in, I find the first opportunity to stop and run a simple five step process (based on the Time Boss Weekly Framework).
Step 1 - Get It Out of Your Head and On to Paper
The worst place for us to manage our to-do list is in our head. We can only hold 5 to 7 things in our working memory, and I was well past that.
This step is easy: simply list out on paper (or in your preferred to-do list manager) anything that is competing for your time. Just keep going until it's all out. Don't allow any task to cross your mind without adding it to this list.
Don't feel pressure to write well structured to-do items at this point, just get it out of your head in a way that's referencable. As an example, on of the items I listed on Saturday was "Get good at video content". Not incredibly actionable, but I know what I mean, and I'll make it actionable on step "Step 3 - Make It Easy to Make Progress"
One of two things will happen:
- Less Items Than You Think - Alex Hormozi says "fear is a mile wide, and an inch deep", and you often discover that when we get the list out of our head and onto paper.
- More Items Than You Think - Though not ideal, this is also good. Reality is your friend, and you can't manage reality until it's all in front of you.
Once it's out of your head and in front of you, you're ready for the next step.
Step 2 - Ruthlessly Decide What Actually Matters
This is basic prioritization. Use any method you're comfortable with, and at least prioritize the items you need to do in the next 5 working days.
The key is there can be no ties. At 8am tomorrow, you can only truly do one thing at a time, so you need to decide what order you're going to attack this list.
I prefer force ranking, starting at the top, and comparing the first two items in the list against each other, deciding which is more important. I then move on to the second and third items, working my way through the list.
Once you're list is prioritized, you're ready to move on.
Step 3 - Make It Easy to Make Progress
Your brain craves dopamine. And it’s easier to get it from processing email, scrolling social media, or Netflix than from the giant, vague tasks on your list. That’s why breaking things into 1 to 2 hour, manageable chunks is your secret weapon. Why? It gives your brain a powerful feeling: "I'm making progress."
Let's return to my example: "Get Good at Video Content". My job is to break this task down into manageable next steps, 1 to 2 hours in length, with a clear definition of done, that I can absolutely attack. Here's what I did:
- Find 5 creators in similar spaces that I can emulate (1 hour)
- Research their common practices, including anyone they reference as guides for them (2 hours)
- Create at least one video with at least one improvement from my research (2 hours)
Notice what I did: I went from a very non-actionable task "Get good at video content", and broke it down into tasks that fit perfectly on my calendar, and more importantly will make me "feel" like I'm making progress on a task aligned to my priorities. Will I be "good at video content" after these three tasks? Maybe, but for certain I'll be better over the next five working days, and I can break down more tasks next week as needed.
Why 1 to 2 hours? These are defendable time slots on your calendar. You already defend 1 to 2 hours all the time on your calendar: you call them "meetings". You simply will be adopting the same mindset for these tasks.
This part takes some work, so be ready to dig in here. AI can also be an incredible tool here, with a prompt such as:
Please help me break down this task into 1 to 2 hour tasks, that are manageable and help me feel like I'm making progress, and that each has a clear definition of "done": TASK
Once you've decided how to do the work, it's time to move to the next step and figure out when exactly you're doing to do it.
Step 4 - Figure Out When You'll Actually Do the Work
With your tasks prioritized and broken down into manageable steps with a clear definition of done, it's time to map these items to your calendar.
Tasks want time, and your time is expressed on your calendar. You are going to create calendar appointments for each item on your calendar in your available slots.
When you run the full Time Boss Weekly Framework, there's a number of sub-steps here, including adding your personal items to the calendar, adding recurring tasks you've already committed to, and adding Whirlwind (aka buffer). You can learn all this quickly via the Time Boss Masterclass if you'd like. It's not required, but it will dramatically increase your ability to actually achieve your list, and do so without overwhelm.
Once you've filled your available time, it's time to deal with all the items that don't fit.
Step 5 - Make a Plan for the Things That Don't Fit
You've already made some commitment plans for the items you had time to do. Now you have to make commitment plans for the items that don't fit, or they will continue to create stress for you. What are your commitment plan options for the additional tasks on your list that you didn't have time for?
- Defer Tasks - Future you has more time to work on tasks. Can you make a commitment plan to review the task next week/next month/next quarter instead?
- Delegate Tasks - Other people have time, and you don’t need to do everything. You just need to do the part only you can do. Can you create a commitment plan for other people to handle the tasks instead of you? If you've struggled delegating in the past we have a great article for you.
- Digitize Tasks - Digital tools have effectively infinite time. Can you make a commitment plan for an AI or automated tool to do the tasks for you instead?
- Downsize Tasks - Can you spend less time on a task, accept a "good enough" outcome, and still achieve the result? This frees up more time in your calendar for other tasks.
- Delete Tasks - Can you simply decide to do less and say "no" to lower priority tasks?
- Do the Tasks - Sometimes leaders simply have to make things happen. If none of the strategies above work, can you increase your capacity this week to deal with the tasks that don't fit? This should only be done if you have a promise or commitment, otherwise do your best to use the other commitment plan options above.
It's important to recognize that this is not easy. When meeting with my 1x1 coaching clients, we spend almost all of our time here, and I help them creatively think through commitment plans that don't require them to simply "do the tasks" all the time. This is why it's important to have outside feedback on your calendar, and ensure you are being honest with yourself on how finite your time is.
With this step done, you now have commitment plans for the items that fit, and commitment plans for the items that don't fit. You should see your overwhelm dissipate, and your clarity and commitment to your goals and values increase.
How to Ensure You Can Achieve Your Plan
I feel your resistance as you read this. "Andrew, that's all fine and good, but my world is chaos, I'll never be able to stick to this plan."
I get it, I resisted change FOR YEARS for the same reason... and it cost me my health, negatively impacted my relationships, and in my heart of hearts I knew I would eventually crash (and I did, in spectacular fashion). The challenge is you've lived into your current situation, and you have to live your way out of it, working through the blockers that prevent you from changing.
There's four blockers you're up against in making change related to your time:
- Relationships - Up until now, you've trained your relationships to operate a certain way with you, which often means being pulled in a million directions, and spending time on everyone else's priorities, instead of your own. You'll have to retrain your relationships to operate with you differently, allowing you to continue to be supportive of them, and ensure your priorities are achieved as well.
- Environment - Up until now, the environment around you has killed your ability to focus. Open door policy, constantly looking at email or messages, working from home, etc. None of these are inherently "bad", but they must be evaluated for how they serve your goals and values.
- Systems - Up until now, your systems have broken down from time to time (or never been created in the first place), and you've simply allowed it to take your time and focus as you work through solutions to broken systems. Your systems need to be evaluated (or created), with a new gut level commitment to feel pain one time, solve the root cause of any system breaking down, which will dramatically increase your ability to focus.
- You - Up until now, you've been able to blame relationships, environment and systems for all your problems related to time. As you install the Time Boss Weekly Framework, and quiet the noise around you, often the final boss you have to overcome to to make real change is you. This is not easy work, and often requires outside feedback to see the blindspots that prevent you from making change. If you can overcome this final blocker, time becomes the ultimate tool for you to get whatever results you want, and to do so without overwhelm.
We'll expand on each of these challenges in future posts to help you navigate each blocker.
What if You Need to Get Immediate Results?
If overwhelm is costing you sleep, health, and results, and you need to make a change immediately, consider the upcoming Master Your Week Course.
In just 6 weeks, the Master Your Week Course helps leaders like you get 35% more done, win back 4 to 10 hours a week, and finally feel in control of your time. 97% of participants report less overwhelm and more peace. The next cohort is launching soon, and seats fill fast.
If you're not sure the course is right for you, or would like to discuss your unique situation, please grab time with us here. If nothing else, we'll give you feedback on your current situation and offer an easily implementable tactic or two to relieve some pressure.
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