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16 Days of Peak Performance, Styled as a Competition

Top engineers, professionals, entrepreneurs, and executives join the Pentathlon in order to get an edge in their Most Important Work and permanently level-up their work habits.

Pentathlon XIII: October 12 to 27, 2019


Live Training











Peak Performance, Now.
Permanent Gains, Forever.

We all know what it feels like to be "firing on all cylinders" — where every day runs smoothly, and you hit the pillow at night proud of the day's work and sleep soundly and well.

Why is it often hard to "get there" — to fire on all cylinders?

Success and a really great life doesn't come from a single thing, but from getting a lot of things right, consistently.

Doing great work requires taking care of your body and mind, planning and setting up your day well, and tying everything together.

That's where we come in.

The Ultraworking Pentathlon takes the form of a competition to reach consistency and excellence across the big areas that lead to having a great life.

Then we stack together a bunch of "known best practices" to help you thrive, day-in and day-out.

At the end of the Pentathlon,

(1) You should rate it as one of your most productive and thriving time of the year.

(2) You should walk away with permanent gains in your ability to work effectively, stay calm and focused, self-management, impulse control, and planning and succeeding across your life.

The cycle and review structure helped keep me focused. The points made sure I didn't let my team down and made me extra competitive. I found myself doing the things I should do even when I didn't want to do them.

Brian Kidwell

One of my favorite parts of Pentathlon was seeing concrete ways to operationalize... I'm a sucker for really in-the-weeds examples to help get me started/focused.

John C.

Work takes 80% of your life. UW will give you a huge permanent boost to your work effectiveness. So compared to admission price, ROI is infinite. To me it's just a no-brainer.

Mony Chhim


What's Stopping You From Reaching Peak Performance?

We designed the Pentathlon to help you reach peak performance now, and permanently increase your skills and abilities forever. Here's some of the common roadblocks to peak performance, and how we're helping you navigate them:



It’s easy to get bogged-down and not do enough of the really important things.

You know how it goes: Firefighting. Distractions. Interruptions. Obligations. Everyone to some extent deals with these, yet it's absolutely essential to reliably do the things that are most important to you in life.


The Pentathlon helps you clarify your Most Important Work and make progress every single day.

Before the competition starts, we provide simple-yet-rigorous analysis and target setting tools. You'll know what your Most Important Work is and the whole event and supporting community are geared around you getting it done.


Stress and burnout are real factors that often come from neglecting the fundamentals.

What's the right level of stress and pressure? The challenge is staying in that rare zone where there's a lot of growth and achievement without getting overwhelmed by stress or burning out. Peak performers are able to reliably push the edge of their limits while staying healthy and fresh in the process.


Pentathlon helps you push your limits while respecting the fundamentals so your health and sanity stay high.

On the Pentathlon, you'll be tackling big, expansive goals but also staying sane and healthy in the process. In addition to doing great work, you'll have basic targets and an accountability structure for sleep, nutrition, and fitness.


With a lack of accountability, people often break their own promises to themselves.

A lot of success comes from routine consistency. Sometimes, this can feel routine or mundane, and people often break their habits and goals when they feel bored or restless.


The competitive and team aspects of the Pentathlon sharpen awareness and bring out the best in you.

The Pentathlon is scored, allowing you to see your progress while building greater consistency, motivation, and new skills. You'll be on a team with other great people looking for you to put up excellent results.


A lack of supportive people around makes it hard to sustain great habits and practices.

One of the most common things we hear from top performers is that the best times of their lives are when they're surrounded by exceptional people and everyone is mutually supportive. Since much of modern life is solo, often people aren't getting those gains and are even paying some penalties.


The Pentathlon combines live training with a community of people committed to peak performance.

The type of people who join the Pentathlon are very motivated, ambitious, achieving people. You'll be in a mix of engineers, attourneys, accountants, business owners, programmers, creatives, and other professionals and entrepreneurs.


Sometimes people get stuck reading and thinking about making changes, but the gains come from putting things into practice.

There's a lot of information on these topics. It can be hard to pick out what's right or relevant, and even harder to put it all together. Much of it works, the key is getting the best practices installed and consistent in your life.


Pentathlon is an "attack dose" of peak performance through best practices, competition, skills training, and technology.

You basically can't not be productive on this thing. Buy the ticket, take the ride.


The Mechanics: How the Pentathlon Works


The tech was quite helpful - I really like having the work cycles spreadsheet, and being able to check yes/no every day on important baseline areas and have my own weekly score update was motivating.

Kanjun Qiu

The Pentathlon is a competition – but like a marathon, you’re competing more against yourself than other attendees. The goal is to be the best you can.

Every day, you'll be scored on the following five categories:

  1.  Sleep/Wake Schedule
  2.  Most Important Work (scored for both Consistency and Depth)
  3.  Physical Fitness
  4.  Nutrition
  5.  Planning

You have some flexibility in how you set targets – we give you some best practices and diagnostic tools, but everyone has a slightly different setup and life. You'll pick targets appropriate for yourself and where you're at, and then you're scored daily on them.

What we mean by that: you get to set your own “Sleep Target” and “Wake Target.” Sebastian Marshall, one of the Ultraworking founders, will have his “Sleep Target” at 8PM and his “Wake Target” at 4AM.

All participants are free to choose the sleep/wake targets they want. Sleep by Midnight and up by 8AM are, of course, fine. Whatever works for you. Once you set it, stick with it and you'll be scored on how well you do it.

Every night, I write out on a piece of paper the things that I plan on getting done the next day. Since implementing this, I’ve noticed a huge boost in productivity. With this minimal amount of planning, I now always feel that the things I am doing are the things that I should be doing. This significantly reduces any potential feelings of stress or overwhelm.

John Ferguson, participant in a half-dozen past Ultraworking events

“Most Important Work” will be the biggest gain for most attendees. You will be scored on doing at least 10 minutes of your “most important work” each day — helping you generate very strong consistency — and you will be scored on how many minutes you spent on your most important work up to a reasonable limit.

Again, you will set exactly what “most important work” is to you — for a writer, it might be obvious (writing and outlining, for instance) whereas for a startup founder, it might be obvious (new sales calls only) or it may be very non-obvious (a range of product development and working to get product/market fit).

You will likewise define your own targets for physical fitness, nutrition, and planning — since we all have different baselines, the intensity and difficulty will vary. We’ll work with you to ensure you’re setting targets that are a mix of improvements-over-baseline, but also sustainable.

You’ll be getting (1) guidance and coaching, (2) structure, (3) accountability from us, (4) accountability from fellow attendees, (5) optional weekly reset/refocus/troubleshooting events where you can get feedback and guidance if you fell off on one dimension.

Competition: A Terrific Format for Peak Performance and Getting the Most Out of Yourself

Without the competition aspect there would have been days I wouldn't have worked on my Most Important Work, but with the Pentathlon I made sure to at least log a few minutes and think through what I need to push forward.

Caroline Poser

The competitive nature is really motivating. Once you get started, you just keep going.

Paul Weidinger

At the start, the points themselves motivated me. Then it transitioned to not letting the team down.

Kendra Kinnison

I am watching my daily progress with bemused detachment. Yes, I want to score more points, because... just because.

Phil Hodgen

The Pentathlon is structured as a competition, and runs for 16 days (14 of which are scored). 

We designed the Pentathlon that way to harness a lot of natural human inclinations and drives. Notably, competition helps people tap into larger amounts of willpower, it increases the salience and significance of actions, it generally makes everything more exciting, and it leads to the formation of team dynamics that are mutually supportive and strong.

In short, we've built the Pentathlon in a way to help you maximize a 16-day window, aiming for really genuine peak performance, pushing against your limits and seeing what you're capable of.

I found the Pentathlon so useful that I've already signed up for the next one. In addition to keeping me focused on Most Important Work, it's the first time that I've been able to go so many days in a row on fitness and waking up early. Pentathlon is great for my health!

Manuel Simon

At peak performance, you get a ton done and you feel great. That's a big part of what we're aiming for: helping you get outside your comfort zone and get a lot more done, get all the achievement that comes with that, and stay healthy and sane in the process.

In addition to all the benefits of peak performance now, we want to help facilitate permanent gains in skills and workflows so you're better forever.

It's a very friendly competition: the participants on the Pentathlon tend to be driven, achievement-oriented, mature, quite successful people. There's a mix of attorneys, accountants, programmers, engineers, entrepreneurs, creatives of various types, and other types of professionals and executives: you're very likely to get someone who is terrific on your team who also thinks slightly differently than you do, and be able to learn from each other.

Teams don't interact much and there's certainly no trash talk, yet knowing you're competing against others is highly motivating and increases the significance of each and every behavior, helping you find willpower to do a little more or hold off from some bad behavior you'd rather avoid.

Finally, there's a maximum score per day of 600 points.

On the first Pentathlon, 4% of participants were perfect-scoring. On the second Pentathlon, it was 9%.

We think those numbers are about right: it's very possible to score perfectly, but also quite challenging. You can see what a perfect setup for 16 days would look like, and aim for a burst of perfect habits and solid and consistent execution on your Most Important Work.

It's an incredibly motivating environment, filled with great people, and you can experience peak performance for a couple weeks straight – getting a lot done in the process, and taking lessons on how to thrive with you forever.


Work Cycles

Live training for cutting through difficult work.


The final piece of the puzzle is our live "Work Cycles" training.

The biggest thing I realized is that when I focused during Work Cycles, I can get a workday done in 3 hours... By getting the work done in disciplined cycles, that then frees me up to work on bigger things, as well as showing me where I was wasting time in the past.

Glenn Holman

As a programmer when I first heard of cycles I had some reservations since I didn't believe that 30 minutes would be enough time to get into the flow state required for software development. But after some real world experience... I went on to realize that if your programming tasks aren't divided into small enough pieces that they fit within a 30 min coding session, you either don't know the problem and potential solution well enough, or you haven't put in the effort yet to figure out what the solution should be, which should always be the first step. So now I'm sold on using cycles for software development - it's saved me from a lot of wasted time and effort.

Han Chang

Great way to spend time with people who want to be killing it on a Saturday instead of nursing hangovers.

Brian Mather

It might sound a little silly at first, but we found that a lot of people don't know how to consistently work on important and hard stuff.

We developed a method of live training-by-doing that helps people (1) cut through their Most Important Work and get an immense amount done, and (2) teaches how to be better at working permanently.

You show up with some of your Most Important Work to do, and then you do it in real-time under guidance and training. We break the work down in spreadsheets into actionable parts, separate out outcomes and actions, and track physical energy and morale across the work session.

It sounds complicated, but it's very simple and a surprisingly fun way to get a lot done. On every Work Cycles, you've got an instructor there if you have any questions or get stuck in your work, and you get the added accountability and social value of knowing other people are working alongside you.

We'll be running three live, real-time training sessions on how to precisely accomplish your Most Important Work. 

These will be at 12PM Eastern Time (9AM Pacific) on:

  • Saturday, October 12

  • Saturday, October 19

  • Saturday, October 26

We ran one of these training sessions as part of the first Ultraworking Pentathlon, which was a gigantic success. By far, the biggest request from first attendees was more of these training sessions.

You asked – you got it.

We now run three Work Cycles during the Pentathlon. The second two are optional, but we see a very high attendance rate for them, and attendees tend to love them. 

The Pentathlon will run for 16 days; 14 of them will be scored. That means the first Saturday serves as "training wheels" for learning how to work very effectively and get a ton done.

In the past, we've charged $140 per session for these types of live trainings, which people happily paid and were consistently thrilled with the outcomes, rating themselves anywhere from 1.5x more productive (for people already doing well) to 400% more productive (for people that knew their work well), to infinitely more productive (if a person was stuck/blocked and literally couldn't make progress, and we helped them get un-stuck).

Who Should Join

The biggest predictor of whether you'll have a great experience at the Pentathlon is whether you've already got something important in your life that you like and want to excel at.

Past participants include engineers, attorneys, accountants, professors, entrepreneurs and business owners, programmers, managers, and people doing a wide variety of creative work.

Attendees come from a wide range of walks-of-life, from their early 20's to their 50's and beyond. Men and women both join and get immensely out of it; sometimes husband-and-wife couples have joined and found it great for their productivity and their relationships.

This has been great... The "existence proof" that there is a network of people like this (like me), is extremely reassuring and inspiring.

Michael Taschuk

The biggest win? Finding people who don't think it's weird to test best practices for your productivity.

Shanna Mann

Sharing ideas, rubbing shoulders with people that I perceive to be much more focused and higher achievers... So frustratingly (!) simple, yet powerful.

Brian Mather

The structure, tech, training, and community can help you get more of your Most Important Work done while keeping yourself healthy and sane in the process. 

It's not remedial, though — Pentathlon is explicitly not designed to "fix your whole life", and doesn't answer the question if you don't know what you want.

We have some pretty good diagnostic tools for identifying which of your priorities is most important and how to hone-in on those,  but all of this presupposes you've got something very cool in your life and you want to have more of it happening.

It's an intense and challenging environment, with lots of people already thriving and doing excellent work. If you've already got some good things going on and want to make more of what matters to you happen, then you'll be right at home on the Pentathlon.

If you’re potentially interested, here is what you’re committing to...

  • The Pentathlon will run from Saturday October 12 to Sunday October 27 (16 days).

  • The first day will be a trial run with instructions; the last day will be a closing ceremony and valuable debrief to share your lessons, connect with other competitors, and make some nice friendships and relationships

  • There will be three multi-hour live training sessions, on each Saturday of the Pentathlon (October 12, October 19, October 26).

  • If this is your first Pentathlon, you must attend the first live training session to get instructions and get your feet on solid ground.

  • The other two Saturday trainings are optional, but we think you'll like to attend.

  • The closing ceremony on Sunday October 27 is optional, but highly recommended.

  • You'll be committing to scoring yourself and inputting your data daily. We make this painless — it takes (literally) less than five minutes, and we'll send you reminders in the format you want (text, email, etc). But you'll need to commit to those five minutes per day, as well as doing as well as you can on your most important work, and the other elements of the Pentathlon.

If you're ready to reach some peak performance now and get some permanent gains forever, we'd love to have you on the Pentathlon. You can register here —

Normal price is $300

Peak performance from October 12th-27th, 2019.

You’ll also get three months of The Work Gym for free (normally $49/month billed quarterly) to keep momentum going with regular Work Cycles every week.

Enthusiastically recommended IF you're serious about leveling-up.

Gregg Jones

It's hard to state clearly, but the Pentathlon is clearly working very well. The core habits are indeed core and my life is more effective when I keep them up.

Malcolm Ocean

I was way more productive than I was immediately before the Pentathlon. About equal to my most productive times... It's a good way to jumpstart your productivity if you are in a slump, and it's a good way to get to the next level if you are already doing great.

Diarmuid Kidney

Frequently Asked Questions

Can I attend in person?

Nope. The Pentathlon is an online event. However, we have had roommates, couples, coworkers, and families participate together, and this can be an extra layer of in-person accountability.

I’m in Asia and the trainings take place late at night. Can I still attend?

We need you to be there at the first training to get you set up, and to have everyone there. We know that's brutal and means either waking up very early or staying up late at night. We have had people participate from Australia, Japan, China, Thailand, and the Philippines and get a lot out of it, but we recognize it's a little ugly.

I’m traveling / vacationing during the middle of Pentathlon. Should I still attend?

There's a place to mark this down during registration: it probably means you won't win the whole thing, but you'll still get some good gains from doing it. We've occasionally had participants with totally crazy multi-continent travel schedules who reported it helped them a lot. Feel free to email us if you want to discuss the specifics, but you should be good to go.

Does Pentathlon work for people with family and kids?

The Pentathlon is perfect for people with a family and kids; we've seen spouses enter the Pentathlon together and gotten a lot out of it. Two pieces of advice: first, when you're doing target-setting, be realistic about what sleep/wake times are pragmatic and discuss them with your partner. Second, tell your partner about your goals (especially on nutrition) and ask for their support on those. That's a winning combination.

I have no idea what I’m doing with my life. Will Pentathlon fix that?

No, we don't know what you should do with your life either. Sorry about that.

Can I run a Pentathlon with my company / team?

Yes, we've had cofounders and colleagues join the Pentathlon together and get a lot out of it. If you have 5 people or less wanting to attend, simply have everyone register as normal and request to be on the same team. If you have more than 5 people, you can register and request some mix of teams or you can email us and we'll coordinate with you.