Note: This section has been updated with new AI additions—so even if you caught it on March 28th, 2024, it's worth a revisit. Last week, I found myself in a state of minor overwhelm.
It wasn't a crushing feeling, but rather a "just wrapped up with final exams" sense of exhaustion with an underlying concern that I may not be able to accomplish all I need to over the next few months and, as a result, may let people down.
When overwhelm hits me—which seems to happen 2-3x per year—I go through the same process to get back on track and feel clear, calm, and settled again:
Hanging at Expo West with my bud Jordan Bass CEO of Hop Wtr…seeming like I have my stuff together but in my mind thinking "How am I possibly going to get all of my shit done?!"
1. Am I doing the things outside of work that I need to do to fill me up? For me, this mainly comes down to working out daily (a lot of Marcus Filly's
Functional Bodybuilding right now), connecting with friends/family multiple times per week, and reading/learning to bookend my days (this morning it was
Scarcity Brain). But this wasn't the problem this time around.
2. Am I giving myself enough space to think, take walks, and be spontaneous? I prefer ~one hour/day of free space to perform at my best. This is usually planned on my calendar, but there is no preset goal re: what I want to accomplish. Just space to think. This was also not the issue last week; I've felt good here.
3. Is everything in my mind and everything that has to be done written down on paper (or in a document), prioritized appropriately, assigned to a particular person, and scheduled to be completed in a reasonable amount of time? I have an entire system of doing this for myself and my team that I'll share with you shortly (all in
Notion—HERE's a decent one if you want to get started). Last week, this third point was certainly part of the issue. Particular objectives had not been broken down into their sub-components (a necessary but at times painful endeavor), and there were numerous goals that had yet to be calendared. Fixing this was a big part of getting me back to good—but not the most important part…
4. Are my days packed with activities that MULTIPLY MY TIME OR DRAIN IT? This last point is where I want to focus today. Because I believe it's the most important. There are certain activities that give you back time, and there are certain activities that drain even more time than they initially take up. The goal is to maximize your
Time-Multiplying Activities (TMAs) and minimize your
Time-Draining Activities (TDAs).
TDAs are those activities where no future leverage is created, and you typically feel less energized after spending time partaking in them. Unfortunately, this is where most founders spend the majority of their time.
Some of the most common, harmful TDAs I've experienced—and see other founders struggling with frequently—include:
i) Trying to achieve Inbox Zero with Email/Slack There is no worse disease than the disease of email & real-time communication in business.
Who cares if you get to inbox zero? There is no reward, and 90% of email is not important.
My recommendation to every founder?
Use AI to triage and batch. Tools like
Superhuman + AI,
ChatGPT plugins, and smart Gmail filters can surface what matters, summarize threads, and auto-draft replies. You can then spend just
30-60 minutes/day max in comms—without losing context or missing opportunities.
I still keep my inbox closed and my phone tucked away—but now I've got an assistant that flags the real fires, summarizes Slack threads, and sends me a digest at 4 pm.
Want a recommendation for an amazing agency to find you a VA? Respond to this email with the subject "VA Please" and explain what you need them to do, and I'll help you out (the exact recommendation depends on your specific needs).
ii) Saying "yes" to activities that are not your top priorities I try to no longer say "yes" to people in real time. Rather, I politely decline, or I let them know I'll get back to them if my answer is affirmative.
Why? As a founder and/or CEO, almost all of your time should be spent on your company's top 3-5 objectives. No one's time is more valuable than yours, and your ruthless prioritization will have positive ripple effects on the organization.
Just about everything else should be politely declined, offloaded/delegated, or put in the parking lot for future prioritization.
This does not mean to eliminate serendipity. It means don't allow serendipity to distract you from your key objectives (assuming your key objectives are the right ones).
Pro tip: I've tested the LLM-based assistant (like
Motion) to auto-manage my calendar around my priorities, protect deep work blocks, and suggest time slots
only if the request aligns with my weekly goals. Pretty cool—I don't currently use it—but it was solid.
AI helps with ruthless prioritization—
without sounding like a jerk.
iii) Meetings—those without agendas & those that don't need to happen at all Meetings exist primarily to make people feel good, even though most people admit to hating them.
Who feels good about them? Management. More specifically, leaders that have failed to establish good systems in their business or those who don't have more important shit to do (due to ineffective planning or incompetency). To them, meetings feel like positive work/progress, although that's rarely the case.
👉 Bonus cheat code: Use AI meeting tools like
Fireflies,
Fellow, or
Otter to auto-record, summarize, and tag action items and skip meetings you'd rather read in 2 minutes.
The meeting rules I've learned & set after 20 years of entrepreneurship and a LOT of wasted time:
- No agenda, no meeting
- Can we meet asynchronously, with people filling out their metrics, updates, questions, and answers on their own? Do this instead
- Can a meeting be canceled? Then cancel it every time
- Limit repeating meetings to those that are absolutely essential
- Meetings should usually be reserved for collaboration, brainstorming, problem-solving, and real emergencies…less commonly for alignment, vision-setting, review, and fake emergencies
All of these rules assume each person on your team knows exactly what to do by when, believes they can achieve their goals, generally understands how, and also understands how their goals ladder up to the goals of the organization. Need a solid meeting template?
HERE is an easy-to-use, simple Notion meeting template you can share w/ your team. The goal? Fill this out 48 hours in advance and circulate 24 hours in advance; otherwise, cancel the meeting or push it to next week.
❗Pause until next week❗
Next week, we'll pick up right here, where we'll dive into the
Time-Multiplying Activities (TMAs) to focus on—including AI tools that can quite literally buy back your time. We'll also explore different ways to
frame time itself—so you can design your days like a founder who's playing on a different clock.
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