Running over 300 miles taught me a lesson I thought I’d learned

I was an early(ish) adopter of CrossFit. I did the whole thing pretty seriously from 2006 – 2010. Greg Glassman, the founder of CrossFit, said something that really stuck with me, “Set a low trajectory on the horizon, or gravity will fix it for you.”

He means that you have to seek incremental improvements. This isn’t terribly different from Bill Gates’s “We often overestimate what we can do in a year, and underestimate what we can do in ten.”

We return, it seems, even to the rabbit and the hare.

I quoted Glassman dozens of times. To my wife. To friends. To players on my team. I felt as though I had really internalized the lesson. I encouraged caution in others when starting new things. I pushed for realistic goals over idealistic goals.

Looking back, I never really grokked what Glassman said. I had seen it. I had touched it. I had even used it and pushed it on others, but I did not have the perspective to master the idea and make it my own.

If you’ve read some recent posts, you likely understand that I’ve begun a journey with running. That continued in 2019. I ran hundreds of miles from Spring to Fall. I generally followed the ideas laid out in The New Alpinism and The Uphill Athlete.

I started running because endurance sports are sports that you can improve at with age and because they enable me to be better at the outdoor recreation that I enjoy the most. The hard part for me, an Enneagram 8, to get started with endurance running is to run slow and far day after day for weeks. My anaerobic energy systems were so dominant after years of CrossFit style intensity that it took weeks or months to bring my aerobic system into play.

The painstaking and seemingly interminable process made me realize how poorly I’ve gone about so many of my own goals. I should have been running slow for weeks at all of them. This is as true of my financial planning and investment ambitions as it is of my strength in meditation. I should’ve had the same outlook at the outset that I’d need 2-3 years to get to the level I wanted to be at now.

I should allow and encourage the people I work with, live with, and love to make progress in the same way. I should expect the same sort of potential and progress from my local and national institutions. If not, I should expect gravity to fix it.

Time budgets and the impersonal irrelevance of apparent success

In a turn of events that will surprise no one, I use a lot of spreadsheets. Google Sheets tend to be my jam because I don’t have a personal copy of Excel and they’re easy to share. If you’re surprised by my overuse of something boring – please don’t request or look at my reading list. In any case, I find that over the long haul I have coalesced around using these sheets to do dozens of things from sharing a budget template, tracking weight, tracking workouts, creating a sharable backpacking checklist, to predicting future events for decision making.

Goals and spreadsheets

It’s easy to understand why you might pair a goal and a spreadsheet. Anyone who’s looked at SMART goals will understand that you need goals you can measure so you can track progress and understand the progress. Spreadsheets are a great place to compare measurements with goals and track milestones towards greater goals.

The failure modes of goals and spreadsheets

Spreadsheets and goals paired with humans – or at least, this human – are also a fertile ground for a multitude of failure modes. The most tragic such failure mode is the one where you simply have no plans beyond reaching a goal and at this stage you launch yourself into the unknown. This unknown is often the dietary equivalent of Halloween candy binge.

There are too many failure modes to count, but I have a couple more fun examples before we attack the larger scope of my issue with spreadsheets and goals.

The Divide and Conquer failure

The best way to get something done is to work backwards from the goal and divide it into very small, very manageable tasks that require minimal context to execute. The work backwards strategy is timeless, proven, lovable, and sometimes forgotten.

Worse than forgotten, however, is the failure to divide and conquer enough. This is my MO. Present-time me makes tasks that seem perfectly sized and contextualized for future me. Present-time me is unfailingly drunk and spiteful towards future me. Future me realizes this fact when seeing “bite size” tasks like “create website.”

Execution on the divide and conquer front is key, and it can derail you either in the doing or in the failure to D&C properly.

The Overambitious failure

This has little to do with spreadsheets conceptually. It is simply my own tendency to squint at a goal or a progression, grunt, and double it because success.

The reason I posit this one as a failure of spreadsheets and goals together is that spreadsheets exist in a virtual reality of the (perhaps not so) distant future. You don’t always have to reconcile that “create website” task with what it actually takes to achieve it. You don’t have to square Q4 revenue figures three years down the road with the miserable grind between here and there.

The problem with overambitious goals for me is that I tend to get disheartened by that failure to achieve and punt entirely. Or, in another iteration of the same result, I don’t spend the time to plot a new course in the face of impossible odds and my failure to plan results in total collapse. To be fair, in my vernacular here, “total collapse” means I ignore this goal and move on.

The Spreadsheet Frontal Assault failure

There are a couple ideas in battlefield strategy that can seem to be impossible to balance. The first is that you must concentrate your force at the decisive point (moment, battle, meeting, etc.) The second is that you really shouldn’t assault a fixed position designed to defend against you. Concentrating your force in a decisive battle is good, but storming the castle wall is often poor strategy.

I fail a lot on passive barriers. Embarrassingly often.

The Spreadsheet Frontal Assault is a drive into enemy territory where you devote so much ambition and scope to the spreadsheet that you inevitably get bogged down by the meta effort of the spreadsheet. You feel that you have almost solved for the goal with raw VLOOKUP prowess and functions about which mere mortal have scarely heard whispers and then…you didn’t finish that sheet and the goal lays unconsidered for a long winter.

Don’t storm the spreadsheet castle. Storm the Ardennes.

Budgeting the wrong currency

But really. Those are all reasonable failures. They’re fine. You can grow from them. You can still reach your goals.

The problem I have in recent years with spreadsheets is that they don’t have scoring systems built in for the things that really matter in life. Look, I’m not here to preach any philosophy to you, in fact I think you’d be better served to read Derek Sivers, take them all apart in sequence, and ponder that a while if you never have. (It’s not a perfect treatment, but it should get you thinking.)

Philosophy generally out of the way, I will proceed to say that ultimately you have to pick some thing to optimize.

You might pick time. You might pick family. You might pick dollars. Sure. Fine.

Whatever you pick, your actual life will be far more complicated and your choices will be entirely unrepresented in your spreadsheet goals. Unless you choose The Spreadsheet Frontal Assault path. In which case, I bid you a temporary congratulations on your apparent success.

This is a glimmer of the idea that All Models Are Wrong but some are useful.

Let’s look at an example.

Budgeting for time

In my twenties, I decided I was about time. That was my value. I did the ol’ work backwards from an end goal and build up the life you want exercise.

My goal at the time was to walk my daughter to kindergarten and have nowhere in particular to be after. I wanted the time freedom over my days.

I built a bunch of subgoals to get to this one. They were mostly focused on money. Money translated to time freedom in some unknown sequence of arbitrage.

I achieved this goal, but not through the subgoal that I thought was the key. I didn’t do it through working for myself or making a 10x fortune. In fact, had I followed some common advice to burn the ships in pursuit of the goal I think I would’ve failed entirely with serious personal consequences. I wasn’t prepared for the challenges on that path at that time.

Is achieving something not according to plan a success?

It’s both. I’ve found as others have that focusing on something has a tendency to produce results even when they don’t arrive as anticipated. The failure comes when we fail to learn from the unexpected route success took to our door.

The impersonal irrelevance of apparent success

I remember my parents offering me a solemn and earnest congratulations at my high school graduation. My response was disdainful. High School to me was no achievement at all and it connected to precisely none of my goals.

My failure in conception of my time goals and my pursuit of them was a clear lack of value placed in the journey itself. I didn’t care about anything between A and B. I only wanted B. And that, I know deep down, is Thanos level inevitable failure.

The successes I’ve landed in life, the things people compliment me on most are often the things I regard least. Things that connect to precisely none of my goals. Things that I once regarded as my goals. And that is the impersonal irrelevance of apparent success to me. When your accomplished goals no longer matter – as my completed goals rarely seem to – the only thing that does is the journey to them.

Build your spreadsheets. Chase the goals. Learn from them.

Pick ends with the journey in mind. Learn from Annie Dillard.

Life isn’t a scorecard. It’s not about time freedom or dollars in the bank. Square those goals with stacking up days well lived.

Seasonal systems, scoping, and incremental improvement

I’ve tried “becoming” a runner for years. The main reason isn’t because I like running. I despise every stride. Exercise, however, feels good and is tremendously beneficial. Not just that, but the hardest thing to get past for me are usually passive barriers. What workout should I do today? Tomorrow? Do I have that equipment? Do I have to drive to the gym? Where are my shorts?

Laying out my shoes and shorts, having a known distance, and a planned route to run makes the easiest and cheapest possible solution to those passive barriers. It’s the easiest workout routine to sort of do. There’s a lot of good wisdom in that for overcoming obstacles and picking say — a market.

Last year a friend of mine challenged me to an actual running goal. A sub-20:00 5k race time. I had an unofficial 19:06 on a semi-accurate flat course in Manhattan in 2008. It was the best overall shape I was ever in and I was surrounded by other people also running that I could mentally compete against. 20:00 was about 9 minutes faster than I could have run the distance when he mentioned it. It was going to take months to prepare and I’d need a real plan to get there. No more random runs on any given day. I needed to lock in to get there.

I found 5k running plans and 10k running plans. I planned 5-6 months of running and pace targets in a spreadsheet and tracked runs 4-6 days a week as I ramped up. I ran sprints, intervals, hills, mountains, trails, and road miles. I ran a 21:40 5k time with severe knee soreness. That was my best time in years and it was the most serious I had ever been about improving my running in my life, but I failed the goal.

I couldn’t run for 4-6 weeks after the race because I had trained running uphill too hard and developed some significant tendonitis in my right knee. It took me 4-5 months to get serious about running again, but I continued doing other workouts.

My next adventure in running started about six months ago and I think this season has come to an end. I’m looking forward to other goals, workouts, and activities. I’ve been learning to snowboard the past two winters and it makes my preferred style of vertical targeted trail running too hard on the knees.

In the past I would’ve felt like this was a failure, but this time around I was running 5k distances easily. I was putting in 20-25 miles a week with 8-10 mile long runs. I was in much better running shape than the season before and with less stress on my knees until snowboarding ramped up.

This is the crux of the seasonal system. It’s okay (it’s great actually) to do something for 6-16 weeks, bank some real improvement and return to it when you’re stoked to do so.

Doing everything whole hog all the time is exhausting and wastes a lot more motion without the return. I feel the same way about budgeting and financial habits. You can budget hard for shorter periods and bank improvement without tracking everything all the time. Hey, if tracking everything all the time is fun and easy for you then it’s great, but if you feel guilt ridden and like a failure for falling off that wagon — just make it a seasonal system plan. Do a 10 week budget sprint.

Another thing you can do is scope the system. Running is a specific activity goal like snowboarding. Those get naturally scoped for me by how much wear and tear I can put on my knees. Scoping budgeting can also be done. You can explicitly manage only discretionary spending categories like shopping, movies, dates, drinks, or restaurants. Most budget templates or budget calculators can help you get started and scoping to maximum efficiency. It’s a lot less work to only track those receipts, and any system you can stick to is better than nothing. Zero based budgeting everything is the granddaddy of the process, but it might be more efficient for you to focus your efforts on your worst financial habits.

Try on some scoped or seasonal systems this year. I bet you wake up next year just a little bit improved.

“There is nothing noble in being superior to your fellow man; true nobility is being superior to your former self.” — Hemingway

Using Monte Carlo methods to make business decisions

Not sure what a Monte Carlo simulation is? Take a look at a great breakdown of what Monte Carlo simulations are.

Monte Carlo simulation methods make it possible to account for uncertainty in the complex and varied decisions you make in your business. I don’t suggest that one man startups with $1,000 a month in revenue start by using Monte Carlo simulations to analyze decisions. It’s a lot of complexity to add all at once and it’s important to really understand the methodology you’re using to make decisions. It’s probably more important that you understand the methods you use than that the method itself is incrementally more accurate.

If you’re familiar with 538 or Nate Silver from the last couple election cycles, you’re probably familiar with models that offer results similar to what you see from a Monte Carlo simulation. Results are in the form of chances a scenario plays out like building this new technology has a 65% chance to be profitable given these assumptions.

There are some big benefits to using this process in my experience. I have used the method for project management, scheduling, revenue projection, traffic projection, and predicting the impact of pricing changes.

Monte Carlo simulation benefits

Durable, reusable models

Once you understand the method and construct a model for a decision, it’s a highly reusable tool. If you take the time to build a decent equation or series of equations for a given decision then your model should stand the test of time. You need not recreate it to analyze future decisions. You will make some minor changes to a series of assumptions that govern the model and see what the impact is.

The durability of these models helps everyone reason about the impact of the inputs and it also lends itself to incremental improvement when you discover that you could model something more accurately or you need to add a variable. Even when you need to make adjustments, doing so tends to be cheap after the initial setup. My experience with high-low models or other discrete estimation sheets is that they are rarely reused.

Impact on team reasoning

Most people don’t reason about the world in a probabilistic way. We may think in terms of binary outcomes, but few people label most events with a likelihood of occurrence much less see all factors in that light.

Most of the time this is fine, but complex decisions and complex situations benefit from clearer thinking. Helping people working in teams see that there are a range of possibilities for completing each milestone and how those uncertainties sum into a project scheduling estimate can really change the way they see the process and even the rest of the world. Probabilistic thinking is a key critical thinking skill in a data driven world.

Improved estimation

Like any model you would choose to use, there is an increase in the accuracy of your projections independent of the impact on thinking. Part of that is the shift to thinking in probabilistic terms, but part of it is due to a better method of combining the numbers to find estimates. The common estimation method of taking an average or looking at a high and a low case come with some classic errors in statistical reasoning. Models based on these methods are quicker to create and may aid speed of decision making (a good thing) but they are inaccurate and will provide you with poor decisions in the end. Only you can decide when the tradeoff is worth the cost for speed relative to accuracy, but I would note that once you understand the method and have a model under your belt you won’t find the difference in time to create a model to be very great. The time cost is upfront in building your first model and understanding the method.



The psychological triggers behind the 15 most important pricing page features

Great pricing pages use customer psychology to guide people into purchasing the best plans for their needs with high conversion rates and extremely low bounce rates.

We have studied the best pricing pages we could find for small businesses and distilled the dos and don’ts of the trade. These pricing page dos and don’ts will also explain the psychology at work in both the positive and negative cases so you understand how to apply each technique to your pages.

  1. Do use an H1 that speaks to your customer

    Try to speak to benefits your customers care about. “Pricing” isn’t a headline. It’s a placeholder. Read more.

  2. Do use simple plan names

    Try to use easily understood plan names. Avoid potentially confusing jargon or industry terms.
    Read more. 

  3. Do use familiar iconography but be judicious

    Use universal icons where appropriate, but avoid introducing new icons to your audience. Read more.

  4. Do use button copy that connects to user intent

    Aligning button copy with user intentions reduces friction. Read more.

  5. Do focus on the important differences between plans

    Highlight the important differences that you expect customers value most highly. Read more.

  6. Do highlight common features in an “all include” section below the table

    Improve the plan table by factoring out the common features. Read more.

  7. Do feature a plan with color, size, and weight

    Show with color and visual hierarchy what you think is best for customers. Read more.

  8. Do use a unique button style or copy for your featured plan

    Using a unique CTA on your featured plan’s button further highlights it. Read more.

  9. Do include a below the table option to contact us or to reach sales

    Some users will have questions or prefer to speak with a salesperson. Make it easy. Read more.

  10. Do include an FAQ specific to billing

    Answer billing questions succinctly to parry customer objections. Read more.

  11. Do include a testimonial with a picture of a human

    Testimonials with a real person showing are powerful social proof. Read more.

  12. Do show what people, businesses, or segments benefit best from different plans

    Tell people what they should expect for each plan. Make it easy to identify which role they fit. Read more.

  13. Do offer to sell add-on products and services to customers on the pricing page

    One time offers at the moment of sale are the easiest way to do two critical things. Read more.

  14. Do feature trust markers on the page

    Guarantees and authority trust markers can improve page conversion. Read more.

  15. Do have a CTA on the bottom of the page

    The second most important element on your pricing page. Read more.




  1. Don’t use “Pricing” as your H1

    Your headline is the most important copy on the page. Read more.

  2. Don’t use “purchase” as your button copy

    Learn how to use button copy to entice users to click Read more.

  3. Don’t use non-standard icons for plan features

    Icons can confuse more than explain if they aren’t universal. Read more.

  4. Don’t force customers to scan the table back and forth to see differences

    Clarity often means simplicity. Clarity can drive purchasing behavior. Read more.

  5. Don’t show all plans as equals

    All plans are not created equal. Understand why showing equal plans leads to bad customer decisions. Read more.

Cialdini’s Weapons of Influence

In his national best seller book Influence The Psychology of Persuasion (originally published in 1984), Robert Cialdini explores his six industry-defining principles of influence. If you have not read it, read it.

Cialdini starts out describing a single repeatable interaction between a turkey chick and its mother. When a chick chirps (making a “cheep, cheep” sound), its mother will come and take care of it. Turkeys are deathly afraid of polecats and they are also afraid of inanimate stuffed polecats. Yes, you are correct; turkeys are not the brightest creatures in the world. Interestingly, the “cheep, cheep” sound of a chick emitted from a speaker concealed within a stuffed polecat totally trumps the turkey’s instinctual fear of the polecat as the mother turkey will run to and coddle the chirping stuffed polecat. OK, the words turkey and bright should never find themselves in the same sentence.

Ever heard of Click, Whirr? It’s a thing; Google it. Remember that this book was published in 1984? Imagine a cassette tape loaded in a cassette player.

You press play (Click) and immediately you hear the mechanical sound of the tape rolling (Whirr). A chick’s cheep cheep chirp (try saying that 10 times fast!) invokes a repeatable automatic behavior (Whirr) from its mother. Cialdini continually uses the Click, Whirr metaphor when describing these “fixed-action patterns” invoked by a “trigger feature.”

Cialdini’s mission is to outline what he calls the weapons of influence as they are used mercilessly on us everyday. He is most interested in illuminating the most common and most potent strategies that are employed by anyone that wants you to comply with whatever their agenda is.


Suppose a co-worker gives you a small insignificant Christmas gift. Suddenly, you feel an intense amount of pressure to return the favor. Click, Whirr – That is reciprocity. It is wielded by the gift-giver and it immediately provokes you to comply.

Commitment and Consistency

Suppose you agreed to meet a friend for drinks after work but you simply do not feel like it. However, you go anyway because you said you would. Click, Whirr – That is commitment. In this instance, it was wielded by the inviter which compelled you to do something (it does not matter how insignificant or carefree). Once someone has succeeded in gaining a commitment from you, this principle does the rest of the work. Be careful as this can grow into the sunk cost fallacy.

Also beware of the flip side of this coin: consistency. Suppose someone asks if you think some generic and generally widely accepted statement is true followed by a call-to-action question afterward:

Do you think murder is bad?
Would you support our effort to stop murder?

Do believe that children deserve to grow up in a healthy environment?
Would your support our effort to help the children?

If you answer YES to the first question, you will feel compelled to answer YES to the second question.Click, Whirr – That is consistency. Everyone perceives themselves to be consistent (none of us are hypocrites).

Social Proof


If you are like me, you have a healthy disdain for canned laughter (the on-cue loud and obnoxious laughter that is emitted from so many television programs every 15 seconds).  Click, Whirr – That is social proof. Social proof states that one strategy “we use to determine what is correct is to find out what other people think is correct.” Canned laughter is a modern day example of the baby turkey “cheep, cheep.”

Liking or Likability

Have you ever contributed to any charity a door-to-door volunteer attempted to sell you? Me either. Have you ever contributed to a charity your neighbor, friend, or relative shared with you? Have you ever bought girl scout cookies? Boy scout popcorn? Me too.  Click, Whirr – That is likability. So the next time that you are talking someone that is pitching anything to you and you discover that their mother is from the same town you were born in but knows nothing about this small town, think again… people will say anything to get you to like them.


Well, if the masses of social proof did not convince you, maybe the recommendation of one celebrity would? Because we all know that corn flakes are delicious because Michael Phelps (most decorated Olympian of all time) apparently enjoys. Click, Whirr  That is authority.


Once you perceive any resource is not infinite, you will be more biased to say YESClick, Whirr  That is scarcity.

There only 2 in stock – better order now! (scarce stock)

If I want it by Thursday, I must order within 15 hours and 46 minutes. I better hurry and make a decision! (scarce time)

Sure, you can wait to put an offer in on the house, but I do know there are several others looking at the house this weekend. (scarce time)

Final Thought

Don’t be a turkey. When that stuffed polecat chirps, beat it with a sledge-hammer or at least pay no mind and simply walk away.

There is a war out there, old friend. A World War. And its not about who’s got the most bullets, its about who controls the information. What we see and hear, how we work, what we think. Its all about the Information.

Cosmo (from Sneakers)

Now, armed with the awareness of the most popular and effective techniques that others are using to get you to comply to their wishes, you can better navigate life’s interactions. Maybe you can leverage these techniques yourself in your business?

Share the best or most surprising use of these principles you’ve seen recently!

GatherContent’s pricing page

Things we like

1. Bottom CTA
2. Featured plan
3. All include
4. Billing FAQ
5. More questions contact CTA
6. H1
7. Annual billing + discount

Things we’re not sure about

1. No humans or testimonials

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KISSmetrics’ pricing page

Things we like

1. Featured plan
2. “Get Started” CTA copy
3. Many layered CTAs
4. Add-ons
5. Billing FAQ

Things we’re not sure about

1. Event volume + Things we like pricing is confusing
2. No bottom CTA or questions section

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