A Foolproof Productivity Tactic, Cognitive Fortification, McConaughey's Memoir, and More.

Bring Ambition Newsletter - January 28, 2021

Hi folks and welcome aboard new subscribers!

In the Bring Ambition Newsletter, I share 5+ things that are fascinating me lately in the world of professional and personal development, peak performance psychology, meta-learning, side hustles, and more. You'll receive unconventional resources, cool gadgets, practical advice, and other inspiring content.

As always, if you enjoy the newsletter please share with a friend!

1.) My foolproof productivity tactic:

The initial shock of the pandemic faded away, and overwhelm crept into its place.

Being forced to suddenly and unexpectedly adapt to a 100% remote environment sapped everyone’s cognitive, emotional, and physical resources. Productivity levels became intensely volatile.

One strategy that helped me is what I would call Microscheduling.

It helped me kick-start my productivity by going back to basics, breaking objectives down into tiny, impossible-to-screw up pieces — and making sure they got done.

How to:

  • Using my trusty Outlook calendar, I scheduled tasks and activities down to precise intervals — usually fifteen to thirty minute slots between meetings, but sometimes as little as five minutes.

  • These were appointments I made with myself. Dedicated time to tackle to-dos and reply to emails. Time slots for deep work on important projects, for thinking strategically, for ideation and brainstorming. Sometimes it was simply space to rest, eat, step away, pet the dog.

By making the process effortlessly robotic (i.e. boring), my productivity "flywheel" had no choice but to turn. Moving mechanically through the day was worth neutralizing the overwhelm.

Important rules:

  • Planning and prioritization: Start with your objectives and goals, break them into action plans, prioritize the actions, and then schedule accordingly.

  • Discipline: Understand that some "appointments" will get crushed by fire drills and new priorities. But you must protect important slots, or this tactic doesn't work. Unfinished "important work" needs to take the place of other, less urgent items.

  • Reevaluate: Continually reevaluate your strategy and make little improvements. Find what works and is reasonable for you.


  • Autopilot: Puts you completely on autopilot — you remove stress, procrastination, and "feeling like it" from the equation. You just stick to the script.

  • Motivation: Understand that if you've prioritized correctly and follow as much of the schedule as you can, you'll have a good day. Stack enough good days together and you'll find you had a great year.

  • Time protection: For high priority items, your calendar's "busy" status could deter some potential distractions or conflicting meetings.

  • Speed: Setting and adjusting the schedule should cumulatively take about five to seven min.


  • Fire drills: Of course, random, urgent intrusions can knock your entire day off track. Protecting time slots can also be challenging when our time is not always our own. But without a plan, this flips the whole Monopoly board. If you do have a plan, you simply reprioritize and adapt.

  • Loftiness: It's easy to be overly ambitious with your microscheduling. Think of this like a 1- or 2- week prescription for restoring baseline productivity. The jury is still out around sustainability long-term.

  • Optimization trap: It's also easy to fall into the "optimization trap." You should make little improvements here and there, but don't turn this into a massive event in itself.

  • Learning curve: It takes a while to figure out what's reasonable. Maybe your 3pm "snack and meditation" slot that keeps getting pushed simply isn't going to happen.

  • Effort-effectiveness relationship: Your schedule is only as effective as your prioritization.

So if you find yourself unable to maintain productivity while working remotely, or prone to procrastination, or languishing in the frustration of never "feeling like it," give Microscheduling a try.

There is freedom in the tedium.

2.) Real-life castaway of the month:

Otokichi (later known as John Matthew Ottoson) was a Japanese castaway who floated for 14 months on a rice boat across the Pacific Ocean. His unbelievable life was made into a movie in 1983. It starred, of all people, Johnny Cash, in what appears to be a Bilbo Baggins costume:

(This is obviously LOTR Shire Bilbo, not ringless Rivendell Bilbo or Hobbit Bilbo.)

3.) Book I can't stop thinking about:

I recently finished Greenlights, Matthew McConaughey's new memoir, and it took quite some time to figure out…

I read a lot about entrepreneurs and other "self-made" men and women. The stories are all about ambition and adversity and perseverance, the peaks and valleys of chasing some audacious goal and then miraculously grabbing hold of its tail and wrestling it down from the dream world. The books inspire but also challenge you — you can't help but question, "Would I have made the same tough decision if I was in their shoes? Am I chasing my dreams or coasting? Am I doing the hard-but-necessary things or making excuses?"

McConaughey's story was different. It was certainly about dreams, but it wasn't about the grind, fighting tooth and nail to rise from obscurity. It was about dealing with rapid success in almost untenable magnitudes, in an environment where nothing is what it seems. It was about self-reflection, introspection, self-discovery, ethics, personal philosophy. It's rife with comedy, adventure, and vision quests. McConaughey never rests on his laurels. He risks everything to reach higher planes. And most importantly, he constantly re-prioritizes, putting family and fulfilment before fame and rearranging the rest of his life accordingly.

Now that I've wrapped my head around Greenlights, I'd highly recommend it. It'll give you a glimpse into the unfathomable challenge of trying to stay grounded despite massive stardom. It'll motivate you with a high-stakes story of risking success and comfort for a chance at more meaningful work. And best of all, you get to spend some time in the brain of the coolest of cool dudes, the wayfaring raconteur and outlaw poet himself, Matthew McConaughey.

4.) Cognitive fortification of the week:

"The Baloney Detection Kit: Carl Sagan’s Rules for Bullsh*t-Busting and Critical Thinking." Here's a fascinating article from BrainPickings about critical thinking and combating propaganda, distilled down from the ideas in Carl Sagan's The Demon-Haunted World: Science as a Candle in the Dark. Sagan's book has long been on my reading list, but until I make the time, this article is an excellent primer and summary.

If only Sagan could see the world today!

5.) How to create your own country

If the story about the real-life castaway got you fired up, maybe you'll be interested in "How to Create Your Own Country." This is a fun piece, and the author tackles it from a pretty unique, realistic angle.

If anyone wants to go halfsies on a decommissioned ship pls respond.

I'd love feedback on this newsletter. What did you enjoy? What's the worst (or most boring) thing about it that needs to be fixed as soon as possible? Reply here, or you can reach me on Twitter or Instagram.

Have a great weekend!

Jon D'Alessandro

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