The Pain List and how it helps you

Until I started taking my Pain List items seriously – and I’m still contending with some of them, today – until I started putting some of this stuff to bed, nothing new was coming into my life. My life didn’t feel like it was going in the direction I wanted it to go. It didn’t feel like it was going anywhere. In fact, if it was moving at all, it moved to a wasteful end. 

What was underneath that was I had a history of learned helplessness in the face of obstruction. “If I try, it’ll only end up in disappointment, so I prefer to dream.”

Life is full of obstructions that loom larger than they actually are. Dysfunctional people resist our unclear or maladroit attempts to remove obstructions to make our situations and relationships better. (When we get really clear, it’s hard for them to thwart our changes.) They typically respond in a way that shuts us down. In the face of getting shut down, some people get clearer and go for it another way. Other people, however, give up more easily.

The dysfunction of resisters (or, the resistance of the dysfunctional) is also their way of giving up, but they don’t always realize that. Most people are trying to protect themselves, frankly, and they do it through minor forms of negative control – often when they simply need to learn how to lead

Entire cultures can fall prey to this. It takes insight to realize that obstruction might have good reasons, and resistance might have good reasons, but both obstruction and resistance are not permanent conditions. They are moveable and negotiable. A Hero isn’t always required. 

Pain often comes from feeling helpless about a particular task, person, block, or outcome. It takes small, consistent effort and positive reinforcement to unlearn helplessness. 

I had to do it, and I’m still working at it. For example, I’m very patient and persistent – so much so that I forego rewards I should take – but I have a low frustration tolerance. Until I had the internal and external resources – including money and its ever-ready excuse! – to start moving on the things I needed to clear, I was stuck in a mystifying holding pattern: waiting for something to happen, not recognizing when it was happening, and under-using my power to direct all creation in my life. 

There is one positive thing this stagnation taught me, and it’s expressed in this poem:

The Just

A man who cultivates his garden, as Voltaire wished.
He who is grateful for the existence of music.
He who takes pleasure in tracing an etymology.
Two workmen playing, in a café in the South,
a silent game of chess.
The potter, contemplating a color and a form.
The typographer who sets this page well,
though it may not please him.
A woman and a man, who read the last tercets
of a certain canto.
He who strokes a sleeping animal.
He who justifies, or wishes to, a wrong done him.
He who is grateful for the existence of Stevenson.
He who prefers others to be right.
These people, unaware, are saving the world.

by Jorge Luis Borges

This is real life, too. You are always, ALWAYS living a real life. And you are always learning what works and what doesn’t. There are seasons of growth and there are seasons of dormancy. This is natural.

It’s time for you to breathe out the old, and breathe in new energy.  

Create a Pain List – 7 to 10 things that you should have done by now, old business that was frustrated and remains outstanding, debts to pay, debts to call in, projects that need one final push to complete, applications for new opportunities that may not yet be lost. Things that may make you feel some embarrassment or shame, where you underperformed or let someone down. 

Then analyze the first three steps you can take to get each bit of business sorted.

And then, immediately, act on the very first step of each of them. 

Record the outcome and expectations of that very first step, and schedule the second step or its follow-up. 

When you get it done, reward yourself, and release that negative energy. With any luck, the negative energy will already be released during the process of resolving that pain item. It so often is the case that doing something constructive about pain becomes, consciously or in retrospect, a pleasant and rewarding task. 

Why I created Life’s Battle Plan and the Tactical Chronograph - and how they’ll help you

printed version of the series

I’ve just spent a full year turning my self-management systems into a product, email course, and digital downloads. Doing so was an exercise in learning everything I could about product design, creation, marketing, feedback, and how to put stuff together to benefit someone else. I could have learned these things working on someone else’s product, but I felt compelled to build, and I reached for what as at hand. What I built was Life’s Battle Plan and the Tactical Chronograph.

See, when I created these products, they were one - and I hoped to turn it into a premium Kickstarter by now: a creamy paper version of a life planner where people could think with their pencils to make an annual plan. They’d then have a book of accompanying agendas, usable on a monthly basis to keep their scope narrow. Yet the slim agendas still had the space to gather all the thoughts that don’t get entered into their phones. I believe in paper agendas and it’s not a rocket science product to reinvent, but I did my own little twist.

I sent out the planner and three months of the agendas to my beta testers (lesson learned: create a not-your-market-obstacle to purchase, especially if the free product is costly; casual curiosity and social support/flattery were bounce points). But before the end of the three months, one of my beta users got back to me asking when April’s agenda would be ready.

Thus was born the monthly agenda-by-PDF subscription that struck me as sense-making, and with that, a new design cycle. But that also separated Life’s Battle Plan into two products: a life planner for people facing change when they need to sort their options for the long term, and agendas for people who like novel structures and have a need to keep it all on one place - not flipping back and forth between pages, different notebooks, and devices when it came to planning, journalling, and keeping track.

So I came up the name Tactical Chronograph, kept the moniker “Life’s Battle Plan” to mark it as part of a suite, and promoted it to my beta testers and anyone else intrigued by agendas, #bujo (bullet journalling), and productivity. (And I chose creative-operational men between 25–44 as the customer avatar.)

One year later…

Now that a full year of offering the Tactical Chronograph for free-for-feedback has passed, I’m turning it into downloadable bundles at various prices. I validated what I needed to do to build a better product; now, it’s find its market that is, buyers.

That means no more dedicated Tactical Chronograph email every month. If you sign up to the list for this, you’ll still get a welcome message with the links to the archives of everything everyone got for free – but thereafter, I’ll include a “merge block” for you and others who showed interest – so the quarterly newsletter I send out might have a paragraph just for all of you who buy, use, and love (or: hate and critique) my agendas.

The original story of “Why?”

The section below used to be what the people on my Tactical Chronograph list would get in the Welcome email, after an explanation of where to pick up their downloads at first signup.

Everything we do when we face forward has a bit of backward-facing in it. We like to solve our own problems and seek others who can relate. I thought sharing my original struggle with my subscribers - now you - puts a bit of humanity to what’s thought of as an innately-talented-and-extroverted class of people: entrepreneurs. We might be anything but.

Why did I create first the workbook?

Because wanting to become more focussed and effective was why I created my own Creative Vision that became “the LBP.”

I was sitting on my back patio one summer in the afternoon sun (yes, day after day), reading management books and wondering how I was ever gonna do all the things I wanted to do. “I used to want to do this, I still wanna do that, but there’s a conflict,” “how do I get the money, how do I find the time…,” basically overthinking it. How I could ever pick “just one” like everyone told me to –  and why was my life not on track like it should have been? (Feeling a little sorry for myself - ☑️)

This frustration really bothered me, so I wrote it all down and organized it. Then I brought it into a community youth entrepreneurship organization and met with Ernie, one of the business coaches.

He took a good look at it, and then he looked up at me over the wire rims of his glasses and said, “I think you’re confused.”

Well, yes - but this is a good step to get un-confused, right? Because if I walked in without that document and just spouted off All The Things I wanted to do, it might’ve been worse than confused! It might have been dreamer- level discreditable.

Then Ernie said: the best business to start is one that you have at hand, quickly, and then let it grow organically from there. He told me about a little company called Urban Seedling that was doing a residential service for urban agriculture- something I was already blogging about at Big City Little Homestead. He encouraged me to niche my AirBnb and develop more in that area.

The following year, I hired Urban Seedling – a local company doing urban agriculture, like I was doing, my own way – to help me convert my driveway to a green one, something I’d always wanted to do. I designed it myself and needed help with the labour and expertise. And with that, one of my two companies was born, out of my casual little blog, promoting and consulting on native landscaping, green driveways, and bird strike prevention. It aligns with skills and knowledge I had on hand, with something I wanted to do that has meaning: regreen the city, and prevent biodiversity collapse.

That’s an example of what can come from getting clearer about ALL the things you want to do. And it whetted my appetite to keep pursuing what I now call All The Things. And wrangling them is what Life’s Battle Plan is about.


Life’s Battle Plan is being re-released in a second edition as a PDF Workbook next week (December 21st, just in time for Christmas, if you or someone you love stated an intention to use the holidays for reflection). Order it in the Shop here.

I also created a walk-through version by email that anyone can take. All you need is a journal or notebook. It begins this weekend, on December 15th or 16th, so that you can reflect and plan in time for New Year’s. Go to this page and subscribe, and you’ll get Day 1 right away.

You can use the output of the e-mail course to populate the Workbook for posterity and future changes, as you might not want to carry that paper notebook around with you for the next 2 years.

What I promise is this: do the homework, and it will organize all the things you want to be, do, or have into a meaningful, actionable plan. You’ll be oriented and ready for 2019 and beyond.

You’ll come out with greater clarity, commitment, and congruency - a satisfying well-roundedness that connects your livelihood, relationships, interests, fun, and long-term vision. And with clarity, commitment, and congruency, you will earn results, wisdom, and integrity.

Bonus: I’ve decided to “leave the gate open” on the email course until Orthodox Christmas, or Epiphany (January 6th)  –  because I want you to have one (an epiphany, that is), and set up the best 2019 possible. Then I’ll close the gate until the next round.


By the way, my company’s name is Projectica. Its mission is kinda badass. I’m not a productivity guru, and I don’t want to be. I consider my tools a scaffold, and you can do what you want with it. I’m just someone who thinks creatively with a process. I want to enable more people, especially those who face extra internal and external challenges, to increase their capacity to do great and grounded work.

I hope you’ll join the course, or check out my other projects and products.

You can still join my mailing list below. If you’re up for a user interview - or have a great story to tell me about procrastination!–that link’s good, too. You can book directly in my calendar. And if you’re looking for a UX researcher or product manager or designer, I’m looking to learn more and be hired.

This story is also published in The Startup, Medium’s largest entrepreneurship publication followed by +399,714 people.

You'll need to confirm your e-mail to get on the list. There are more options in your profile such as your location, birthday, and topics you find interesting. But this'll get you started.