Work Cycles, and Getting Hard Work Done Reliably

On the first Pentathlon in mid-2016, we held one set of "Work Cycles" to kick off the Pentathlon.

Work Cycles are a simple but powerful way to get a lot done. As strange as it might sound, many people don't know how to reliably and methodically get a lot of hard work done.

During Cycles, we get together as a group and break down work in spreadsheets, set measurable and achievable targets, and re-evaluate progress, energy, and morale every 30 minutes. We've now had hundreds of people attend Work Cycles, and attendees often report being anywhere from 25% to 400% as productive as compared to their normal baseline. Occasionally, someone breaks through on work that was "stuck" and nearly impossible for them, making them more-or-less infinitely productive compared to their baseline.

More Work Cycles was the #1 request after the first Pentathlon, so we now schedule three rounds of them for each Pentathlon, on every Saturday. We ask people to come to the first one, it's mandatory, so attendees are guaranteed to learn a method to get their Most Important Work done. The second and third set of Cycles are optional, but have a very high turnout rate and are very-much enjoyed.

We'll teach you all the basics of Work Cycles during the first Saturday of the event. There's some nuance to it, and it can be tricky to learn without demonstration. This page has some general guidelines adapted from an excellent participant on Pentathlon III, Max Schoenberger, who wrote up his notes and guidelines on Work Cycles.

Consider this more of a reference for best practices after you've been trained; this is a resource for subsequently running Work Cycles on your own, rather than a comprehensive set of theory and guidance.

Max Schoenberger's Notes on Cycles

What Cycles are good for: Cycles are really great for big, great, abstract, hard work (like writing a piece of content, refactoring code, launching a large creative project) or also for boring and tedious work (like answering a lot of email or taxes). It’s not so good for the in between (phone calls, do this, research that all mixed together).

Planning your work session and figuring out what's "most important"

Figure out when and how and where you should do your most important work. The biggest gains happen when you do the same type of most important work every day. Projects get done if you do that. Projects decay if you forget them.

If you do 7 hours of your "most important work“, is it really your most important work, or could you benefit from planning a little bit more in advance?

Estimating how long things take to do

People mostly underestimate how many cycles they need. That’s because a lot more things can go wrong than can go right.

What you want to accomplish should be a short-term goal. It’s done when this small part is done. Focus on accomplishment, not doing work.

Making a estimate for the number of cycles helps you not fall behind schedule, because you realize after each cycle if you behind time. This is especially important if the result is subjective and not concrete. Subjective results can take as long as you want, so setting a quality target beforehand is helpful.

Don’t completely plan out cycles 2, 3, and 4 before you get to them. Things can run over time or you can figure out a faster way to do it.

Can you trust yourself to do your unimportant work after your most important work? If so, do your important work first while you’re still fresh.

The morning hours are often worth around four times as much as the afternoon or evening hours. Losing an hour in the morning due to an appointment is sometimes four times as bad as in the afternoon.

Specify the quality of your work

By setting an estimate for the number of work cycles you implicitly set the quality of what you’re gonna do. By making these estimates you implicitly set quality bars. That's very useful.

Specify the quality of your work. A lot of times we implicitly have a quality bar. Make implicit quality bars explicit. This could save about half an hour. Examples: "Should not be embarrassing, first draft“ or "When people read it they think it's absolutely excellent." Set that explicitly beforehand.

Read the requirements if they're external; define them if not

Read the requirements closely. Be sure that you understood what you should do before you start, and why you should do it.

Read the judging and evaluation requirements. Maybe you think you should be super creative and all they care about are just 4 criteria that must be met.

If no one is setting external requirements, you should personally define the quality requirements of your work; otherwise it's hard to know if you're on pace to complete it or not. It's surprisingly common for people to work on something without defining how "good" it should be, which makes work difficult to complete.

Planning your cycle

Set the starting times of each cycle in advance.

If you have hazards, specify them (internal hazards can be confusion or procrastination, external could be an interruption like a delivery guy...).

30/10 is not magical. 40, 50, 60 minutes are okay, but 30 are good to keep concentrated. If you get distracted after 10 minutes you don’t loose more than 20 minutes. Also people often get lost when they finish early. With writing you can often do longer cycles. But consider breaking other tasks into smaller pieces.

This is the simplest version of cycles. You could add a „Why“ row or a row with a link where you’re documenting your work.

Example: What do I want to accomplish?

First version:

> “Overview all webpages, make notes in physical notebook, then start making changes on lowest hanging page.“

Improved to:

> "Get a complete overview to be able to speed run the webpages to complete, then get started.“

Improved to:

> "Get a checklist that, if completed, I’m done with the website. Do it on paper. Then get started with the first item.“

Why the re-write? More concrete. What I want to accomplish is not to do some work but to get the result, the overview — a checklist to cross off.

What do you want to achieve? Not, what do I work at! Focus on the outcome in the „what do I want to accomplish“ field, not the work.

Be clear about the "Strategic Why"

Strategically, why is this important for me? This especially helps when you start to get tired.

Besides the goal, note down your Why. Firstly, this is important for motivation. But secondly, this also sets strategic direction. Your Why may change what the outcome will look like. A lot of times you don’t know what you want to accomplish until you write down your Why and get strategic direction.

A lot of people are focusing on what work they want to do as opposed as to what they want to achieve. If you haven’t defined your outcome you might miss beneficial things and do unnecessary things. Your Why determines what’s in scope and what isn’t. Also people often get stuck because they don’t have the end in mind.

Stopping points

"One minute warning — get to a good stopping point, please."

If you see it’ll take longer, try to get to a good stopping point. How can I leave this so the next time I start on it I’m getting into it quickly? You can spend the last cycle to line up the work to finish it over the next week. Be kind to your future self, so it’s easy to get going again.

Better to stop your work cycles on a strong note. No need to go till the bitter end. Better to start strong the next day again.

In the last cycle of a day, set up your work to complete easily next time if you didn’t finish.

If you see that you can’t wrap up your work after your work cycles, you want to look to get to a good stopping point. Cleaning up, putting notes in order, throwing unnecessary stuff in the trash, planning future work. That’s something Sebastian is thinking a lot about, and a lot of people are not.

A skill that’s worth picking up over time is getting to good stopping places.

For your last cycle you could do something like this: Wrapped with today’s work — general cleanup and organizing cycle. Clean up my papers, make some notes on future steps, etc.


Plan your next cycle before the break. So you don’t have to think about what you were doing. So you keep your momentum.

A little fitness in the pause is good. Do air squats (hands forward, push hips back). If you’re in a public place you could do them discreetly in the washroom. Little things like this go a long way. Healthy snacks, too, for blood sugar. Body mind duality is BS, it’s all the same stuff.

You may work through a break once in a while. If you do it two times in a row you get usually fried for the rest of the day. Avoid burning yourself out by neglecting breaks.

Whatever you did between two morale/energy-boxes is what caused it. We track energy and morale so you can see it change throughout cycles. If you see it falling or increasing, you've got a good guideline of what changes your energy and morale.

With normal Pomodoro you’ll rush yourself in the breaks (5 minutes are too short).

How about bigger breaks? I don’t really take bigger breaks, but I like to take a nap after 2-3 hours of work. You don’t have to fall asleep during a nap! Just keep your eyes closed and lie still. That resets a lot of brain processes. I don’t fall asleep during 80% of my naps.

Work cycles as a journal

When planning work cycles better include more detail than less, because it creates a log for a work. These are super-useful journals to back-engineer great days, week, and months.

If a work session goes well, just look at your notes and analyze how your thinking worked at the time.

Work cycles make you more reliable

Cycles are a pretty reliable method to get done hard work.

I was tired, but otherwise planning my work out in the sheet helped a lot. I think it especially helps when I’m tired. Clearly plan your work out or you will waste a lot of time and get nothing done, especially when you’re not in the best state (tired etc.). I probably wouldn’t have gotten my work done today if I hadn’t planned it out like this. It forces you to refocus on the important stuff.

This was also Sebastian’s takeaway: by listing out all the problem areas on his website he fixed it probably in a third of the time. Make your list really concrete and then get it done.

How to figure out what to do

My question:

> Sebastian, could you talk a bit about the macro-planning of work? My biggest issue is what things to work on in given day. There are so many factors that are kind of hard to estimate like time for completion, impact, potential for new opportunities, etc. So I often I just guess and it feels kind of arbitrary. Got any tips?

"First, don’t stress, enjoy. I was in your situation a couple of times. It’s terrifying but also really cool. A cool place to be."


I. Keep projects short and completable

II. Answer the weekly review questions

III. Choose monthly themes

IV. Track project start and end dates, total days, and working days

I. Focus on whatever completes the fastest

Tackle the projects that take 4 days before those that take 4 weeks. Pick a small version of want you want to do, so that you can complete it quickly. For example, instead of a podcast that goes on forever do a six episode series. Make it a success that you can show to people.

You don’t yet know if you want to commit to.

A lot of times we come to a false conclusion: I have to either do it completely spending a lot of time or not do it at all. You often could improve just 10% and lock that in (for example, add a testimonial page). If you aim to do everything you’ll often do nothing. Do something and then leave it so you can pick it up later.

Often there’s some ambiguity on when something is „done“ — ergo, I should keep moving fast instead of getting bogged down on one aspect. Move quickly through everything and complete all the low hanging fruit quickly before getting bogged down on one thing for three hours. A lot of smart people make this error.

II. Do a Weekly review

  1. What’s really going on? [Emphasis on REALLY.]

  2. So what do I do about it?

  3. What matters; what doesn’t?

You start gradually creating a record of what’s going right and wrong – when you look back on a string of weekly reviews, you can see if any of the same problems are re-occurring frequently, and then go to work on those.

III. Choose monthly themes

At the end of every month, I look over all my weekly reviews, and compile them into a monthly review that’s rather similar. From there, I pick a personal goal and theme for the next month. For example, more mental toughness, getting things done faster, social skills, mindfulness, leisure etc. Trying to do eight or ten things at same time is too scattered.

IV. Track project lengths

Write down the day you started a project, the day it ended, the number of day in between, and the number of days that you worked on the project. Optimize these numbers, you’ll get more projects done. Projects get stagnate and die when they sit on the counter.

Doing research

If your cycle is research-oriented, note down exactly what you want to know. Doing laser-targeted research won’t stop you from acknowledging unrelated stuff that also might fit in well. But it’s way faster.

When doing research, ask what are all of the decisions I’m gonna make when I’ve done this research. Can I drive it, so that I can quickly get the data for one of these decisions? Locking in one of those pieces will shrink the problem space instead of increasing it. The problem space is getting smaller and the decisions are getting smaller. That can help with overwhelm. Things that can be locked in make the work less rather than more. Ship away at the edges and make the problem smaller. This creates constraints for the rest of it and you don’t have to deal with an infinite decision space.

If you feel like you don’t get enough done

I do 20 cycles a day and I feel like I don’t get done enough. Measure how much time you spent on either the most impactful or the hardest tasks to make sure you’re putting in at least some time of work into it. Front-load your day as much as possible. Grind out at least 2-3 cycles if you feel like procrastinating and then get to the busy work.

Coma week

A morbid name, but effective idea: What 2-5 things would you be happy to accomplish this week? If you fell in a coma until the end of the week, but when you woke up those 2-5 things got done, you’d be happy.

Discovered work

A lot of times when you’re stuck, you’ve an undiagnosed problem (blind spot). After having resistance to reaching out to people to do some promotion, Sebastian realized that he has a lot of stuff to do, so he didn’t want his emails to be back and forth. He overlooked this beforehand and neglected it. He first had to block out times in his calendar and then make it possible for people to book these, before reaching out.

Sebastian got hit with "discovered work“. He missed something early in planning. I used to get demoralized and then I realized that’s just the nature of projects. I could have caught it beforehand. "Am I really ready to do this?“ Think through all your stuff, does it all work and can I succeed. "Will this work complete if i just do it in order?“

The OODA loop

Your first cycle could be figuring out what to do.

OODA - Loop: Observe, Orient, Decide, Act.

Don’t start with Decide or Act.

Work cycles train us to have a faster OODA loop.

OODA loop - Wikipedia:

We value immediate feedback

Points in general don’t matter, a good life matters. But it’s proven that when you get tactile and numerical feedback, it’s more meaningful to humans.

Kendra: "I was not sure if I would care about the points, but I realized early on, that I did. In the end it was less getting points for me, but getting points for the team.“

Sometimes getting a point is more motivating than the "theoretical“ benefits over the long- term of the behavior itself.

Base rates

Look at the base rate. If the base rate of success is one out of ten, then two or three success out of ten are a great improvement. Marketers kind of ruined this. "Everybody can do it.“ —

Nope the base rate is probably more like 10%.

Base rates are so important. If you have the flu and are somewhat productive, you greatly outperformed you usual flu day.


Fatigue levels don’t increase as fast if people work together (was tested with athletes but translates to intellectual work).

It’s also a skill to not beat yourself up and get into a downward cycle after a bad work cycle. It’s very rare that things don’t go wrong.

People tend to put off stuff they hate. So more of the days of their life the next thing they have to do is something is hate. Why not plan a couple of cycles and get it out of the way right away?

Often email generates urgent, unimportant work, so I block email in the morning till 11am. If I read them, I often can’t think about anything else.

Think about switching costs. "Blended Work“ is just slower. Simple as that.

Thanks Max

Again, we'll do full training on Work Cycles on the first Saturday of the Pentathlon, but those are good refresher guidelines for running your own Cycles once you have the basics down.

A huge thanks to Max Schoenberger for the detailed notes; if you wind up taking similar notes, definitely forward them to us and we'll incorporate them into Pentathlon guidance for future attendees.

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