Antifragile Planning: Optimizing for Optionality (Without Chasing Shiny Objects)


Planning timelines have been getting shorter and shorter across every industry over the last couple decades. Companies that used to make ten-year plans now make five-year plans. Companies that used to make five-year plans now make three-year plans.

Slowly, individuals and organizations are giving up the Luddite Hope — “that it is possible to enjoy the benefits of non-zero-sum innovation without giving up predictability.”

My personal shift and revised process was driven by a practical need to resolve the inherent contradiction at the heart of the Luddite hope: focus and optionality.

How do you retain optionality without running around chasing shiny objects? How do you focus on something long enough to make meaningful progress without myopically locking yourself in?

Expect anything worthwhile to take a long time

Focus and attention are becoming steadily more important. There simply weren’t as many draws on attention and energy in the past as there are now. In a world where fewer people are engaged in deep work, those who do so are becoming increasingly powerful as the recent spate of books on focus have made clear. [footnote]Essentialism and The One Thing are my favorites.[/footnote]

it does seem to be true that you can expect anything worthwhile to take a long time and jumping around from project to project (or shiny object to shiny object) is a sure recipe for long-term failure.

Optimize for optionality and becoming antifragile

At the same time, you hear terms like agility, pivot, and adapt. Everyone recognizes that as the external environment and markets shift and shake at a faster and faster cadence, there’s a pressure to keep up.

The solution is optionality. The mistake most people make is they try and use their intelligence or knowledge to figure out the “right” thing to do in advance. Instead, you should generate a lot of options (and opportunities) and simply exercise the profitable ones when the conclusion is obvious.

If you “have optionality,” you don’t have much need for what is commonly called intelligence, knowledge, insight, skills, and these complicated things that take place in our brain cells. For you don’t have to be right that often. All you need is the wisdom to not do unintelligent things to hurt yourself (some acts of omission) and recognize favorable outcomes when they occur.
The mechanism of option like trial and error (the fail-fast model), a.k.a. convex tinkering. Low-cost mistakes, with known maximum losses, and large potential payoff (unbounded). A central feature of positive Black Swans.
 Source: Antifragile — N Nassim Taleb

A friend related a story to me of an old high school acquaintance who was running a profitable business which weathered the recession in 2008 well and was spitting off cash in 2008 to 2011.

He was liquid (read: had a lot of cash on hand) when there was no liquidity in the market at large. After the collapse, there were tons of obviously good deals in stocks, real estate, and distressed businesses that even fairly novice investors knew would provide great returns.

It didn’t matter though because none of the “smart” investors had any cash. Since his business weathered the storm and he had kept much of the previous years’ profit in cash, he exercised the option and invested in a bunch of obviously good deals. He’s made a killing in the last 7 years.

I see many people make similar commitments in their careers and lives. They use a mortgage to buy a house or apartment because “I’m paying rent, so I might as well be building equity,” and then an opportunity comes up across the city, across the country, or on the other side of the world, and they can’t do it because “I’ve got a mortgage.” 2

People that commit to a particular project for five years and stubbornly refuse to re-evaluate are making the same mistake.

Oh, and life happens

Compounding this tension between focus and optionality is that, is that not only is the external reality changing, but so is your personal situation. What you wanted five years ago is probably substantially different from what you want today. What you want five years from now is likely to be substantially different yet again. Seek to be antifragile.

Here it is in a Venn Diagram:

To quickly map the diagram to the terms I’ve used:

  • “What I do well” = Focus — If you want to be good at something, you have to do a lot of it.
  • “What people will pay for” = Optionality — The market is constantly shifting and better to retain optionality to take advantage of the obvious opportunities.
  • “What I want to do” — Life happens. You change your mind about things

All three of the circles in the Venn diagram are in a constant state of movement and seem to merit almost continuous re-evaluation. But, if you spend all your time thinking about how everything is constantly in shift and don’t sit down and actually do some focused work for a long period of time, you’ll never make a meaningful contribution to your field.

This year, I got as close to devising a system to manage this tension as I have yet, and I’d like to share the process with you. I use it personally every 12 weeks and have also used it with coaching/consulting clients to good effect.

The setup

Every 90 days (quarterly), I re-evaluate what I want (my long term vision), what people will pay for (the market), and what I’m good at (my strengths) on a high level basis. I then set a single, falsifiable (yes/no or quantifiable) goal which I hypothesize to be the most impactful move towards that objective.

I.e. “Sell a lot of books” is not falsifiable. “Hit the Amazon bestseller list” is yes/no falsifiable “sell ten thousand copies of a book” is quantifiable.

This provides a “true north” heuristic for each 90 day sprint, where every opportunity that comes across your plate gets evaluated based on “does this bring me closer or farther to selling ten thousand copies of a book.”

Questions like, “Would you like to go to this conference?” or “Should I spend a month just writing for my site?” can all be evaluated by a single goal.

It also lets you prioritize initiatives by their expected value in contributing to that goal. I used a slightly modified version of the Bullseye framework to rank marketing initiatives for my book over the last two quarters when that was my focus.


some are secret and still in progress :)

Every month within the 90-day cycle, you pick the 1–3 highest-priority initiatives likely to lead to the quarterly goal.

Every week you pick the 1–3 highest-priority initiatives to lead to that month’s goal.

Every day, the 1–3 highest-priority to accomplish this week.

If you take the triangular “happy place” area in center of the Venn Diagram, the planning process is a simple exercise

  1. Find your happy place
  2. 80/20 analysis and execution of the actions leading you to towards happy place on a quarterly, monthly, weekly and daily basis
quarterly business review template

This does a few things:

  1. It’s motivating because you can draw a direct line from what you are doing on an hour-to-hour and day-to-day basis to your long-term “happy place.”
  2. You build in continuous feedback loops of planning and reviewing to figure out the highest leverage tasks.
quarterly business review template

So, every 90 days, you:

  1. Re-evaluate the 25-year vision, and determine what the center section of the Venn diagram looks like.
  2. Hypothesize what you can do over the next 90 days which is likely to make the most progress towards that goal

Every month, you hypothesize what 1–3 key things you can do over the next 30 days which is likely to make the most progress towards that 90-day goal. Every week, you hypothesize what 1–3 key things you can do to make progress towards the monthly goal. Every day you hypothesize what you can do to make the most progress towards the weekly goal.


1. Don’t adjust course mid-period.

When I’m working on something day-to-day, I don’t think “I wonder if this is taking me towards my monthly day goal.” All my energy is focused on simply executing on the 1–3 most important tasks laid out for that day. If I have doubts or think of a new idea (I should write another post on my new review process), I add it to my weekly review notes to review at the end of the week, then go back to work.

If I think of something really big-picture during my weekly review (“should I hire someone?”), I won’t change my 90 day goal. I’ll add it to a list to review at the end of the 90 days.

I find that this lets me get the best of both optionality, because I’m only locked into a big project for 90 days, but also focus. I’ve found 1 big focus point for 90 days, you can get a LOT done (like write a rough draft of a book).

2. Always have an escape plan

Among the alternately amusing/enlightening Red Team Rules, rule 1 is the most highly emphasized: always have an escape plan. In this particular context, I always plan for how I can shift gears if the 12-week period doesn’t turn out like I hoped.

When I started writing my book, I said “I’ll spend three months and write a rough draft, and if it doesn’t work out, then I’ll just clean it up and republish it as a series of essays, and I’ll have become a better writer.”

Writing is important to me, so even if nothing else worked out, learning to write better alone was worth it.

You could launch a season of a twelve week season of podcast without committing to doing it for the next decade.

Two important takeaways:

  1. Knowing you can walk away after the 12 weeks makes it easier for me to commit fully to it for those 12 weeks. Think of it as baking in a shotgun clause to a contract you made with yourself.
  2. It also lets you protect your downside. The learning from the experiment should make it worth it, even if the experiment itself doesn’t pay off. If you pick a 12 week project, even if it doesn’t work out, the learning should still make it worth the time invested.

Those are the theoretical underpinnings; if any of that didn’t make sense, it’s all baked into the process, so let’s get into the nitty gritty.

The process

Note: You can download a template to use yourself for this whole process here. Below, I’ll walk through the whole thing. The italicized sections are my commentary.

Preparation: When something you want to think about strategically comes up during the quarter, assign it to end of quarter to think about. I usually keep these in an Evernote note called “Quarterly Review Notes”

  • Ex. During Q3 I will open a note with the title “Q4 review notes,” and put big-picture things that I want to think about — “Should I focus on book sales or email subscribers?” “Should I hire someone?”

Suggested for read/review in preparation for Quarterly Review — I don’t always read all of these each quarter, but I re-read each at least once a year and find before I do my review is the best


The purpose of the quarterly business review template is to

  1. Set a long term vision (What do I want?).
  2. Do an 80/20 analysis of the last 90 days (What am I good at?).
  3. Do a Blue Ocean Analysis of opportunities (What does the market want?).
  4. Pick the top opportunity and SHIP it in 90 days.

I block out a day (it will take two days the first time you do it) to go through the whole process. I try not to do any other work on these days as I want to make the decisions from an elevated position, out of the day-to-day fray. Printing it out and doing it on paper = bonus points.

Step 1: “What do I want” — Long-term/25 year thinking (1–2 hours)

The purpose of the first step is to think really long-term about what you want. How has the feedback from the last 90 day cycle changed it? I do this all of with “free writing” or stream-of-consciousness and focus on getting words onto the page (no one will ever see it except me).

  1. Review General Operating Principles (those are mine; make your own)
  2. What’s changed in the last 90 days?
  3. (Re)write your Aspirational Vision for your life — I find it’s important to start with your whole life, not just business, otherwise you end up creating a disconnect where there’s a conflict between the two
  4. Questions to journal on (If you find the questions too broad, add domain specific endings to each “for your health,” “for your business/career” and “for your relationships”)
  5. What would you do if you couldn’t fail?
  6. “If you were looking back at your life twenty-five years from today, what has to have happened in your life, both personally and professionally, for you to feel happy with your progress? Specifically, what dangers do you have now that need to be eliminated, what opportunities need to be captured, and what strengths need to be maximized?[footnote]This is a slightly modified version of The Dan Sullivan Question -available on Amazon[/footnote]
  7. Your answers should feel totally impossible and saying them out loud should feel really embarrassing. The purpose is that you need something to motivate you when the sh*t hits the fan. It has to be big, or it won’t be motivating enough, and you’ll quit or get bored. That’s why I like 25 years instead of 3–5, because it gives you so much time that you can think really expansively. You’ll apply constraints later, so don’t worry about that for now; dream as big as you can imagine.
  8. Review and Update your Perfect Day — While this may seem redundant with the above questions, I find there’s something particularly elegant about the day as a unit for goal-setting. It forces some constraints (there’s only so much time), and it also lets you very easily compare what you’re doing now to what you would like to be doing, to identify the areas to work on.
  9. If there were no limitations or consequences, what would your perfect day look like?
  10. Where would you live?
  11. What would your house look like?
  12. What would it smell like?
  13. What time in the morning would you wake up?
  14. What would you do in the morning?
  15. What would you think about in the morning?
  16. What would you have for breakfast?
  17. Where would you go for the first part of the day?
  18. What would you have for lunch?
  19. Who would you eat with?
  20. Who would your friends be?
  21. What kind of conversations would you have with your friends?
  22. What are your friends like?
  23. What would you do for personal fulfillment?
  24. What life purpose would you strive towards?
  25. What would your business be?
  26. What time would you start work?
  27. What would you do in your business each day?
  28. What are your clients like?
  29. What’s your relationship like with your spouse and your family?
  30. What would you do for family time?
  31. What would you eat for dinner?
  32. What would you talk about at dinner?
  33. What would you do at night?
  34. Who would you spend your time with?
  35. What would your thoughts be as you went to sleep? [footnote](h/t) to Jaime Tardy and Ben Greenfield for these questions and the exercise.[/footnote]
  36. Edit these answers to create a 25-year vision document and a perfect day document.

The 25 year vision document — The document has three sections: Relationships/Health/Business with the following structure

  • Role
  • What You want — What does it look like? feel like?
  • Why You want it — What’s the importance? Why do I want to be there/in that role?

Here’s what mine for health looks like, to give an example:

I am a Paleo Power Athlete

What: I have a 330 Wilks score at sub 12% bodyfat. That means I have a 1200lb total at 205lbs — benching 300, squatting 405, and pulIing 500. I can do 15 pull-ups. I can do a bar weight overhead squat. I recognize that diet and mobility are the most crucial elements to health.

Why: I prize my physical health so my brain functions at its optimal condition to be able to DO THE WORK. I want people to respect and admire me for my commitment to health and fitness. I want to feel healthy and vibrant for the next fifty years.

The Perfect day document — Take your answer from above and write them as though you were writing a screenplay of a day in your life.

I like to keep these both of these in the shortcut tab of my Evernote, but put them wherever you can look at them everyday. In both cases, they give me something clear to see that I am working towards on a daily basis which I find to be both motivational and a helpful heuristic (Are my actions today bringing me closer or farther away?)

Step 2: Quarterly review and planning — “What am I good at?” and “What does the market want?”

So at this point, you’ve got the big picture definition (what I want) done; now it’s time to put some constraints around it and figure out what is working, what’s not working, and a definite plan for the next 90 days. You do a version of this for each “Life Area” (Relationships/Career/Health).

Review notes made over the course of the quarter for specific, big-picture things to think about (like “should I hire more people or 80/20 my clients?”).


  1. Do an 80/20 Analysis — Review previous quarter’s big initiatives and respond to the following questions:
  2. What went well? What are the 20% of things I’m doing that are driving 80% of results? — While it’s important to make a decision on what you want without considering resources currently under control, once you start thinking about how to get there, you have to change that. I find this answer is usually surprisingly simple. When I look back at the last five years of my life, I can pretty much file everything under two buckets: Generating IP (writing, building internal processes, etc) and Building Strategic Partnerships (I would include internal team management/hiring within this as well).
  3. What went badly? What were the biggest mistakes I made? Why didn’t I achieve what I set out to achieve?
  4. What are the three least-valuable things I’m doing? What are the 80% of things I’m doing achieving 20% of the results? What am I doing to avoid The Resistance? If you get stuck on this one, think of someone that is three to five years ahead of you in your field. What do you do that they don’t? Stop doing that. — It’s easy to think of more stuff to do, and much harder to STOP doing things which either aren’t working or are simply working worse than other things you could be devoting energy to.
  5. Clearly Define a Goal — Thinking about the 25 year vision document, Perfect day as well as what is and isn’t working, ask: — This where I think about what the market wants, as it has to be something concrete that I can realistically do in the next 90 days.
  6. What’s the one thing that makes everything else easier or unnecessary?
  7. “If I am reading this twelve weeks from today, and I am looking back over the past quarter, what has to have happened for me to feel happy with my progress?
  8. The How — How do I get there? Specifically, what dangers do you have now that need to be eliminated, what opportunities need to be captured, and what strengths need to be maximized?” What does the day-to-day life of someone that has already achieved this goal look like? This forces you to fully answer the “what does the market want” portion as you there has to be some reasonable path to getting there in the next 90 days. Brainstorm as many possible options as you can think of for each of the question. There are no dumb ideas, only poorly prioritized execution plans. You’ll prioritize later.

The biggest dangers I have that need to be eliminated are…

The biggest opportunities I see that need to be captured are…

The biggest strengths I have that need to be maximized are…

On an average day, someone that has achieved this goal…

Count the costs — Write all the things you will have to give up and sacrifice to get there and make sure it’s worth it — This is one of my favorites and one that I recently added after reading The Twelve Week Year. It’s easy to get excited about “I want six pack abs,” but do you want to weigh and measure everything you eat, never eat out with friends, not touch a carbohydrate and stop travelling? I didn’t. Not worth it.

4. Choose 1–3 Key Performance Indicators for the goal

  1. They must be specific and measurable — either a number or definitive yes/no
  2. State them positively — rather than focusing on a 2 percent error rate, you would target a 98 percent accuracy rate.
  3. I usually pick 1 key indicator and 1–2 lead indicators
  4. Ex. The key indicator could be revenue, then lead indicators may be new leads/week and sales calls/week. You roughly know how many of those you need to be hitting to hit a revenue goal so you catch issues before they happen.

Reminder: You can download a template to use yourself for this whole process here.

Step 3: Convert into quarterly business review template document

Goal: From Question 2

KPIs: From Question 4

How: Copy from Question 3 — The How. You brainstormed a ton of possible options. It’s now time to pick the key ones, then prioritize them. When I do monthly and weekly reviews, I always have a huge list of ideas, but am only working on the top 1–3.


Step 4: Post-review (1–2 hours)

  • Update your not-to-do list with answers to questions 1–3 — I also keep this in my Evernote to look over every week during my weekly review as a reminder to keep me from getting pulled back into stuff that’s lower leverage.
  • For the business document, move the document for business into the company standard operating document and have it highly visible in the company for everyone to see/report on every day
  • Talk about it in the next team meeting
  • Restructure tasks in project management to conform to quarterly objectives
  • Update Tracking System as needed or move to another system so you are updating and tracking KPIs every day — I currently use Geckoboard, but don’t find it particularly good. I’ve heard good things about Cyfe and also have just used a spreadsheet in the past

Put these documents somewhere that you will review them every morning as part of your morning ritual.

I keep mine in Evernote and they serves as a constant reminder that “Wisdom is nothing more than the profound ability to follow your own advice”


Again, if you’d like a copy then you can download your own Antifragile Planning template here.

For next steps, the my Weekly review and planning can be download here.



Originally published at Taylor Pearson.

Show your support

Clapping shows how much you appreciated Taylor Pearson’s story.