From the daily grind to peak performance in 16 days

Work harder and smarter with the Ultraworking Pentathlon. It's a concentrated dose of competition and camaraderie for people dedicated to their work.

Pentathlon IX: October 13 — 28, 2018



Interested in running a Pentathlon for your organization? Get in touch.


Top engineers, entrepreneurs, executives, and professionals enter the Pentathlon to gain an edge in their most important work:


Woah. I feel like I 2-3x'ed my productivity and consistency... I am building momentum and I don't know if I would have done this launch without having the insight and clarity from being part of the Pentathlon.

Justine P, 2-time competitor

I managed to create an entire new consulting brand, with brand assets, a style guide, a website, procedures (SOPs) to maintain the site and add more content... Without Pentathlon, I would have never done any of this.

Lorenzo S, 3-time competitor

I really like the structure, and the opportunity to do intermittent check-ins and resets with the Pentathlon events throughout the year. Knowing points and teammates are on the line makes an enormous difference.

Mike T, 7-time competitor

What does it take to perform at your best?

We've all been there before — the thrill, momentum, and satisfaction of achieving something significant.

There's a lot of compelling research and advice on how to reach your peak state — deep work, habits, accountability, consistency... Yet putting it all together takes serious effort and can even become a distraction from what really matters.

Our mission is to accelerate the process so that you can flip the switch and focus on doing your most important work.

The Ultraworking Pentathlon is a 16-day experience orchestrated to propel you to peak performance. With dozens of best practices drawn from sports psychology, elite organizations, and behavioral research — it creates a powerful dynamic where you can go hard, maximize recovery, and cement permanent lessons along the way.

We've seen people use the Pentathlon to implement business processes, publish books, learn programming languages, launch marketing campaigns... and otherwise leap forward on difficult, meaningful projects.

I feel like I'm already consistently productive, but this helped to take things to the next level for me. It created focus and helped me to identify specific things to commit to that were measurable.

Meryl J, Pentathlon VI

I had long realized that only a strict daily writing habit would help me become more prolific as a writer. The Pentathlon helped a lot with that and provided an excellent framework for exactly that purpose: To write on a daily basis.

Thomas G, 3-time competitor

Just a few days of knowing that I can be this consistent has made me reconsider what I imagine possible (and has stocked me with an output that would have taken me months at my half-hearted previous rate).

Eli P, 2-time competitor

The Experience

The Pentathlon is a competition at its core. But like a marathon, much of that competition is with yourself.

The aim is to give your best and to help your teammates do the same.

Before the competition starts, you choose personal targets in each of the five Pentathlon categories:

  1. Most Important Work
  2. Sleep and wake times
  3. Planning the day
  4. Fitness
  5. Nutrition

With each success, you earn points for yourself and your team. The competition gets fierce (and motivating) when you see those changes updated in realtime on the global Pentathlon leaderboard.

You'll strategize with your team via mobile or web app to make plans and hold each other accountable. Teams often schedule check-in times, share best practices, and even develop friendships and rivalries over multiple Pentathlons.

Everything is set up to help you reach peak performance while building consistency and recovery in the process.

The Schedule

October 13 — 28, 2018

Listed in Eastern Daylight Time (New York, Toronto)

Saturday, October 13
Opening Ceremony (required), 12:00 PM to 4:00 PM

Sunday, October 14
First scored day


Saturday, October 20
Work Cycles Training (optional), 12:00 PM to 4:00 PM


Saturday, October 27
Final scored day
Work Cycles Training (optional), 12:00 PM to 4:00 PM

Sunday, October 28
Closing Ceremony (optional), 12:00 PM to 2:00 PM


Faster, Higher, Stronger... Consistently.

Join us this October to accelerate your most important work and meet excellent people in the process.

Pentathlon IX: October 13 — 28, 2018

Early registration is $200. Rates increase on September 4!


There is so much value in the community that comes together around UW. It's what really makes the experience. It's great to be with like minded humans, and I love that people are from all over the world.

Beth H, 3-time competitor

Pentathlon has been great. It's shown me the power of accountability – not that I was unaware of if, but it's amazing to see how well something as simple as having a team and performing in front of an audience worked for me.

Caroline P, 5-time competitor

Pentathlon was a place where we, productivity fanatics, could interact with people like ourselves and willingly share best practices. That's an enormous benefit. The chats and riffs were golden!

Gregg J, Pentathlon II

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?

Of course. The first event is mandatory (which does mean staying up late or waking up early) but all the others are optional, and the rest of the Pentathlon takes place on your own time. We've had people participate from Australia, Japan, Thailand, and New Zealand and love the experience, but we recognize the timing of the first day is rough.

What if I’m traveling / vacationing during part of Pentathlon?

We've occasionally had participants with crazy multi-continent travel schedules who reported it helped them stay on their habits. It'll be much more difficult to get perfect scores, but you'll still get some good gains from it. 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 get a lot out of it. Two pieces of advice: first, when setting targets, be realistic about what sleep/wake times are pragmatic and discuss them with your partner. Second, tell your partner about your goals 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 colleagues and even entire teams join the Pentathlon together. If you have 8 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 8 people, please get in touch with us.

The first Saturday of Work Cycles was a powerful moment. Just riding the energy of the team made productivity semi-effortless. The specific planning before the cycles were also helpful.

SoYoung P, 2-time competitor

Health, nutrition and sleep through the roof! I was much more methodical with less fiery peaks and troughs in my work. The Pentathlon really clarifies the trade offs you often aren't conscious of making.

Brian M, 3-time competitor

The scoring system helps keep me motivated — seems silly but it works. The scores changing color to green is another motivator. Having a team to give and get support from is a big help.

Michaela L, 4-time competitor


Flip the Switch to Peak Performance

If you're dedicated to your work and striving for more consistent excellence — our mission is to help you thrive.

Early registration is $200. Rates increase on September 4!