What the Pentathlon Does
We built the Pentathlon to serve two purposes —
- Help you get a massive dosage of peak productivity, during which time you’ll get a ton done while also improving your health and core habits;
- Help you learn and deeply entrain lessons on being more effective — permanently.
It seems to be working well — we’ve now had hundreds of people join the Pentathlon, and a stunningly large number (around half) come back for further Pentathlons.
In this document, we'll cover both some of the "behind the scenes" theory, as well as best practices to hit the ground running, thrive, and carry the lessons forward with you forever.
Systemic 1% Edges
“I was blown away by the system — seeing it in action. It’s not the first time I read something about productivity and how to organize your day, self-help in the grand scheme of things, but seeing it put into action for the first time… it really opened my eyes and I realized how to do it in a very practical way, down to starting, stopping, setting up the time schedule, fixing the five or six important things in your day… that was actually very very worthwhile.”
— Dr. Thomas Goerblich, Veterinarian and Journalist, Pentathlon III attendee
The specific details of peak productivity aren’t hard to understand in theory — it’s putting them into practice that makes the difference. Most people know a variety of things that would help them do better (for instance, waking earlier in the day and doing one’s most important work immediately), but the difficulty is in actually establishing those routines.
This leads us to some simple-but-powerful ideas — for instance, we’ve noted that setting a target “sleep time” is both more effective and more important for long-term sustained success than setting a target wake time. After all, there’s not much use in waking up at 4AM if you went to bed at 1AM — you’re going to be exhausted and not get much done.
That sounds simple, but a variety of simple building blocks — we call them “1% edges” — can come together to make you 10%, 20%, 30% more effective.
Counterintuitively, being 30% more effective on a given day can lead to being potentially double or triple as effective over a month — for instance, completing some work far in advance of a deadline means extra time to either improve and polish it further, or to take extra leisure to recharge fully, or to engage in some other not-urgent-but-important project that you otherwise might not make the time for.
The challenge, again, is identifying these 1% edges and putting them into practice and having them “stick” for you — we firmly believe that running at sustainable peak productivity for even a week or two can show you what’s possible, and that foundation can be built upon.
That’s the core of the Pentathlon — stacking up a large number of 1% edges and best practices, you committing to them, and then us supporting you with as many other elements that we know help someone stay motivated, inspired, consistent, and effective.
Conative Knowledge
You probably know the word “cognitive” — which relates to thinking — but do you know the word “conative”?
Most people do not.
Conative knowledge is knowledge that relates directly to experience.
The next two paragraphs from Stanley Rosenthal’s “The Tao Te Ching: An Introduction” might seem a little technical, but will be useful in helping you understand what we’re doing on the Pentathlon and help you encode the lessons you learn in a deep way, to be more effective forever.
Rosenthal —
“Consider a thing such as a strawberry. If we wish to find the word 'strawberry', we look in a dictionary; if we wish to find a description of a strawberry, we look in an encyclopedia. But if we are hungry, we do not go to the library, but to the field where fine strawberries may be found.
“[…] understanding stems from one of the two forms of knowledge. It stems from that which is called cognitive knowledge, the knowledge born of words and numbers, and other similar devices. The other form of knowledge, conative knowledge, needs no words or other such devices, for it is the form of knowledge born of direct personal experience. So it is that conative knowledge is also known as experiential knowledge. Cognitive and experiential knowledge both have their roots in reality, but reality is complex, and complexity is more of a barrier to cognitive knowledge than it is to experiential knowledge, for when we seek cognitive knowledge of a thing, that is, understanding of it, the knowledge we gain of that thing is understanding only of its manifestations, which is not knowledge of the thing itself."
Part of what we’re attempting to do at the Pentathlon — and it seems like we’ve been succeeding so far — is giving you both a conative understanding of what peak productivity feels like, so it’s fully experienced, as well as a supporting cognitive understanding so you that can identify what elements are helping you reach peak productivity, to build them into your life on a permanent basis.
So Why A Pentathlon?
For similar reasons that people go to a dojo to learn martial arts.
There’s a number of known best practices for learning and developing difficult skills — quick and personal feedback, consistency and routine, visible markers of progress, feedback loops, tradition and morale and momentum, interpersonal dynamics and having other motivated people around, instruction and training, and so on.
Notably, we structure the Pentathlon as a competition that has both individual and team aspects.
Studies have shown that athletes that train together, even in individual sports, have higher levels of endurance and power output, and report less fatigue after training with others in their sport than when training alone. That’s one reason why you see track teams and powerlifters often training together.
For whatever strange reason, people are typically far more willing to break commitments to themselves — whether related to doing one’s most important work, fitness, a good habit like planning each day, or whatever else — than they are to break commitments to a team and other people.
A number of past attendees have related how the team dynamics and momentum helped them not break their commitments and kept them aiming for perfect scores and hitting their targets — and again, once you see the gains and benefits from running at peak productivity for even a couple weeks, you’ve got the conative knowledge of it, and it becomes easier to establish those patterns going forwards in your own life.
“Only a few days into the Pentathlon, I thought I wanted to have some slack — but then I thought, I don’t want to let my teammates down. I need to get back to work and stay consistent in my habits. That helped me keep a perfect score.”
— Mony Chhim
Tangible progress markers — daily and weekly scoring — additionally helps people mark and improve progress, as well as giving tangible feedback if things get off-track. It’s easy to have habits dissolve for unknown reasons if they’re not being tracked — but if they’re being tracked, measured, and scored daily, you get instant feedback if you miss your targets for a day, and can make immediate adjustments.
Core Pentathlon Things and Extra Things
We provide the resources, technology, and trainings for all the core elements of the Pentathlon — but we've noticed a few things that the most successful people do on the Pentathlon in addition to the core material.
We're documenting them here so you can adopt those practices for yourself if you want — getting extra out of the Pentathlon in terms of higher performance immediately, and helping lock-in permanent gains for your life.
Five items we've found lead to a much greater experience on the Pentathlon and long-term gains —
- Commit,
- Counterplan,
- Journal and take notes,
- Establish strong team dynamics,
- Take a leadership role on your team.
Mindset: Commitment
The largest thing you can do to help yourself succeed here is one that might sound boring, trite, and banal — you've no doubt heard it before — but genuinely committing to maximum excellence here is something we see the top performers often explicitly do.
"I made a decision I was going to win, that was the #1 thing — I made a commitment. I was f'ing determined not to miss a single day — other people were clearly not missing their days. Most of this stuff is just showing up and doing it — so I did it."
— Michael Smith, perfect scoring on UWP3
Again, commitment can't be overstated — Diarmuid Kidney runs a small tech agency in his civilian life, but is also a reserve NCO in the Irish Army. For half of Pentathlon 3, he was doing military training exercises. He explained,
"I knew what it would take to get it done. It was tough — really rough — since I was away for half the time doing full-time with the Army. I had to make a commitment to get up early, and do the most important work an hour before everyone would wake up, and get another hour done when we had a bit of downtime. It was tough, but I managed to do it."
This theme recurs repeatedly among people who do excellent on the Pentathlon — they committed at the beginning to maxing out and doing excellent. It sounds simple, basic, maybe even trite — but it's a consistent theme among the people who get the most out of the Pentathlon.
Counterplanning For Success
There's a somewhat silly and dangerous idea in the Western world right now that you should only think positive thoughts, and never think about anything that can go wrong.
Obviously, this is not how any successful organization runs — we have firefighting departments in every major city, engineers think constantly about safety conditions and possible points of failure, successful businesses are constantly assessing the changing risks to their business — but for some reason, there's a silly idea being kicked around that you shouldn't ever "think negatively."
At Ultraworking, both our research and our experience shows that successful people think in advance about what can go wrong, and do "counterplanning" against that.
We have a number of prompts in our surveys and planning tech to help you counterplan, especially about fitness — things like thinking through, in advance, what to do if you're very sore from your last workout the next time you go to the gym.
But successful people often go over and above that. For instance, if you have young children (a number of competitors on the Pentathlon have young families), what will you do the next day if one of your kids wakes you up in the middle of the night? Making a plan of what to do can be the difference between success and failure — in the parent's case, perhaps something as simple as scheduling a nap if this happens, or having some simpler work related to your core most important work that can be done when you're tired.
Everyone's situation is different, but not totally unpredictable — think through, in advance, what could go wrong and what you will do if those things go wrong. Counterplanning means that unexpected disturbances are converted to something known and manageable, and it's worth thinking through what could happen during the Pentathlon, as well as doing this periodically throughout everyday life.
Journaling and Taking Notes
We've noticed that people who journal about their experience, and who take notes from the trainings, do better.
Maximilian Schoenberger took extensive notes on how to set up and run Work Cycles — his notes have been helpful both to himself in mastering personal productivity, and to everyone else who gets to read his notes. We'll cover Max's notes further in the Work Cycles section.
Both Ultraworking founders, Sebastian Marshall and Kai Zau, keep daily journals.
This doesn't need to be a big "production" — even a few sentences about how you're feeling and reflecting on the upcoming important things of the day each morning, and perhaps a quick debrief in the evening, can go a long ways.
If you want a very simple journaling prompt, you could try what Marshall fills out at the end of every day —
What went right today?
What would I do differently?
What environmental factors affected me?
What am I currently improving?
The added benefit of keeping a journal is it lets you analyze what type of habits, moods, and work leads you to more success or less success over time — if you have a very successful week, for instance, you can re-read your journals and notes for lessons to implement permanently. It's not essential, but it's pretty well-proven to work and lead to learning a lot more about yourself — and thus to thrive more.
Establish Strong Team Dynamics
A great team can go a long ways towards a great experience on the Pentathlon.
Unless a number of your real-world friends all joined the Pentathlon (which is a good idea, and has worked for some people), you don't know all your teammates in advance.
The most successful teams establish a communication channel for themselves and use it.
Regarding strong team dynamics, let's first discuss what doesn't matter — the type of IT you use for communication doesn't matter. A Slack channel, a private Facebook group, a WhatsApp group… any of these can work. There's tradeoffs in each of them.
What does matter — commitment and momentum. There will be time during the Pentathlon onboarding session on the first Saturday to communicate with your team and choose a channel together. Once that's chosen, gains come from committing to use it, and building momentum by using it the first few days especially.
Everyone on the Pentathlon has carved out two weeks for peak performance — these are like-minded people, and they can support you and you can support them — if you make the effort to do it.
"Once I started, I decided I wanted to put up perfect scores — and was happy to have another member of my team (Kendra) also put up perfect scores. For the team, I set up a simple Slack channel so we could communicate… just simple stuff, "Hey, hit my goals for the day" — or "I'm flying this weekend, any tips for keeping up targets I might miss?" It helped to analyze situations where we might miss, and I enjoyed getting to know people."
— Nick Winter, perfect-scoring and winning team during UWP2
Take a Leadership Role on Your Team
Some people are more shy, and others are more outgoing — but we've noticed a definite pattern that teams where one or two members took a lead in sharing different types of information, asking questions, and encouraging teammates to join and use the channel helps a lot for success.
On Pentathlon 2, Barbara Garnier and Caroline Poser-Carrihlo messaged using the team channel, and also sent each other text messages to pick each other up and plan together. Barbara explained,
"The fact, being on a team with someone I know — Caroline who is amazingly good — of course there is an effect of pushing you forwards She pushed me forwards… even though I'm not competitive, the fact that she had such good scores, she's so good, I'd like to have at least one day where I score the maximum points… so I'm competitive, but not that much pressure either… we communicated more on bad days, "don't feel good", "feel lazy", "feel like I'm going to eat tons of sugar", it was great safety net and motivation… like a friend basically. It puts a floor under your feet, there's always just a few words to get some positive feedback."
This type of communication is open to everyone — you merely need to take the initiative in sharing your experience, asking questions, encouraging your teammates, and looking for encouragement or strategizing together as needed.
People who take a leadership role in engaging their teammates, sharing their experience, and asking for feedback are (unsurprisingly) more effective and stick to their goals and targets at a much higher rate.
Making Lessons and Gains Concrete and Permanent
Finally, we'll again emphasize that we'd love for you to make more permanent gains as a result of participating in the Pentathlon.
To do that, it's helpful to analyze what worked for you, and why, and to make those into some easy notes that you can refresh yourself on from time to time.
We look to prompt this with our surveys and questions we ask, but you can above and beyond it — marking down lessons learned, why particular techniques are effective, putting those into an easily reviewable format, and sharing those with others on your team, with us, and with real-life friends and colleagues can go a long way towards having better workflows, productivity, and thriving across your life.
We're always very happy to review your notes and journals — if you came across anything interesting, definitely email us at [email protected] and [email protected] — we're here to support you and love seeing you thrive.