Published July 1, 2021

Blocking and tackling, rucking and tackling, passing and finding the angle, building your base mileage. Pick your activity or sport, and there are fundamental skills that aren’t sexy and seem mind-numbingly repetitive.

But they are critical.

Investors, myself included, like to focus on the next idea or narrative. It’s fun and adventurous with the prospect of a pot of gold beyond the horizon. But you know what’s not fun, at least for me? Journaling every day, making sure my portfolio stats are up to date, and documenting why I do things, whether they end up being right, wrong, or still yet to be determined.

These mundane activities are the backbone of my process. I cannot eliminate them, but I often focus on making them less inconvenient or, dare I say, fun.  

Everyone’s investment strategy is different, but journaling and keeping good records should be universal, albeit customized. An algorithmic trader may journal less than a more active fundamental investor. A fundamental investor investing through multiple accounts will probably have a more complicated dashboard than a trader focused on one market or security. You get the idea.

Today, I’m writing about the cornerstone elements of my process (the blocking and tackling) and will share some of the trading tools I use to keep good habits and make things a lot easier.

The Key Elements of My Investing and Trading Processes

I breakdown the elements of my system into four pieces:

  1. Idea Research
  2. Journaling
  3. Portfolio Tracking
  4. Reviews

All of these pieces overlap at the seams and interrelate. For example, journaling is a precondition for reviews, and reviews often guide idea research.

Idea Research

How do I figure out what to invest in or trade? Sometimes, it comes from a quick scan of a chart where something technical pops out. Then, I journal why I want to trade the name and list some rough expectations.

Normally, however, there is a multistep process for evaluating a fundamentally driven idea. If you’ve seen an emerging fund manager pitch book, this is the slide with the funnel. How do you distill a world of noise and come up with ideas?

As I alluded to earlier, reviews often tell me where I should go fishing for ideas. Once I have a few ideas, I run them through a process, where at the end of each stage, there is a choice to continue, delay, or scrap. There are three stages in total.

In the first stage, I do a quick review and look at cash flows, liquidation value/replacement cost, how the idea fits with other themes, and technicals.

The second stage seeks to validate and explore the idea through a deeper fundamental analysis of the financials and industry. Was the initial idea too good to be true?

The final step is to pull the info together into a trade/investment analysis page in which I summarize the thesis and risk-reward based on fundamentals, technicals, catalysts and liquidity.  It also includes a premortem and an admittedly simplistic analysis of how it integrates with the rest of the portfolio (concentration and correlation risk).

At the end of the last step, I have a trading plan and a risk budget for the idea.  


Nearly every day, I take in my observations, feelings, and actions on the market and my positions. I prompt this through a mini-checklist.

This checklist includes reviewing the charts of portfolio positions and watchlist names and prompting questions on news, fundamentals, and technicals. It is also where I record any trades as well as the rationale behind them.

Lastly, I attempt to understand my emotional state versus that of the market. How confident am I that things are working, and how confident is the market? This context in review can help explain behaviors or patterns as they emerge.

Portfolio Tracking

Everyone needs a system to keep track of their portfolio(s) and where they’re headed. I think this is deeply personal simply because people’s styles of investing and trading are so different.   Aside from the basics of P&L, position size, and perhaps sector, theme, or geographic concentrations, everything else is as the creator sees fit.

I will make a case for building your own systems rather than relying on the one your broker provides you. First, you can take the system with you, so you are never locked in, which is not necessarily bad, but a basic risk. More importantly, though, most broker systems miss certain critical details. 

A case in point is receiving dividends. No brokers’ system that I have seen allocates divide to the specific stock you invested in. So if you have a stock that doesn’t appreciate but pays out high dividends, the stock will not appear profitable.


As part of my process, I like to go over certain things monthly or annually. I attempt to suss out patterns, good or bad, to improve my investing process. These reviews have a structure similar to my journaling, but instead of reviewing a day, they review a month.

The first such review is macro. I review PMI’s, relative market performance, and my own sentiment assessment and compare it with prior months. The main objective is to generally understand where we are in the cycle (see prior posts on cycle here and here) and highlight any attention-worthy markets or countries. Lastly, it provides a goal post for portfolio allocation. On the margin, should I be raising cash or allocating more to certain sectors?

I also review my journal entries monthly to catch good or bad trading patterns or processes. Did I try something different that worked, or is there a part of my investment process that needs immediate improvement? I don’t always find something, but I always look.

Finally, I review my monthly journal reviews at the end of every year. Time and detachment allow for greater reflection, and that’s the goal. With either the monthly or annual journal reviews, the usual outputs are tweaks to the overall system.  

Examples include the following:

  1. Do I need to add another question to the fundamental checklist?  
  2. Is there a better way to calculate the capital I am willing to risk?  
  3. Is there a new indicator that worked for a few investments that I need to incorporate permanently?

These are the types of adjustments that come from trial, error, and review.

Considerations for Building a System

What a trading system looks like depends on the person or team implementing it. However, there are a few key questions that can guide you:

  • How much time do I spend on my investing?
  • Does my strategy require bottom-up fundamental research?
  • Does my strategy fall outside prepackaged systems?

How Much Time Do I Spend on My Investing?

If you’ve read this far, you probably spend a considerable amount of time on your investing. Regardless, it’s still important to consider. For example, if you just allocate across ETFs and adjust things monthly or quarterly, you’ll probably need a level of detail that is different and likely simpler and leaner than others. Following charts daily will not make sense. 

Does My Strategy Require Bottom-Up Fundamental Research?

Fundamental discretionary strategies require more bells and whistles when setting up a system. For example, decisions based on discretionary analysis (as opposed to hard rules) require points in a system to record the decision (and the rationale). Since no one’s decision process is the same, these types of strategies usually require more customizations.  

The difficult undercurrent is also converting a discretionary analysis into a prioritized or relatively ranked set of ideas. No two investments are the same, and discretionary investors should be explicit in recording why they prefer or act differently with one versus another.  

This isn’t easy. I find that it’s better to start imperfectly and iterate rather than wait until the perfect protocols are in place.

Does My Strategy Fall Outside Prepackaged Systems?

If someone has already created your system, it would be crazy to build it again from scratch. Sometimes, however, you need to build the system for yourself with tools.   

I invest in many foreign markets that no single broker or account aggregator like Personal Capital covers. So I need to build my own system to capture all of them in one place.  Also, no systems allowed me to create a journal template to ask myself the same questions. So, I created it myself.

This issue is a trade-off between the first question in this section. The less time you spend, the fewer customizations you will ultimately need.  

3 Useful Productivity Tools for Investing

With all considerations on the table, here are several trading tools that I’ve incorporated into my systems. These are general productivity tools that help immensely by allowing for a high degree of customization to fit my esoteric needs.

Process Street

Process Street

Process Street is a cloud-based workflow documentation and execution tool. It allows you to create workflow templates (in older versions, they were called templates) and, once set up, use those templates to execute a workflow (checklist).

Perhaps it isn’t exciting, but there is a lot of benefit to laying out your investment routines and processes. I use Process Street to standardize my journaling and reviews, build out blog ideas, and archive completed workflows for future review. As we’ll discuss later, you can also export them to a more user-friendly format as well.  

This template/workflow model reminds me to regularly consider certain factors and does not let me skip steps. This repeated activity forces me to put my thoughts down and is necessary for subsequent reviews.  



OneNote is Microsoft’s note-taking app. Before we go any further, I want to clarify that I am not wedded to this app, specifically. If you use Evernote or any other app, you get the same bang for your buck.

OneNote is my final repository for my journaling and reviews. Using the tool discussed below, my journals, periodic reviews, earnings call notes and fundamental research notes are uploaded and stored in OneNote. 

Why do this instead of a sheet in Excel or multiple Word documents?

For me, it’s for searchability and organization. If you use tags or references, you can search for any reference to a company within ALL of OneNote. This feature is more difficult if the information is across different Excel or Word documents. You can also get a similar level of organization to directory files within the OneNote application itself. I have a folder for journals, reviews, call notes, general notes, etc.  

OneNote is the repository for my thoughts. I use other tools to deposit primary sources or third-party info.  



Zapier is a cloud-based tool that links applications and automates repetitive processes.  Here are a few examples that I currently use:

  • Each time I complete a journal, Zapier automatically creates a new note in OneNote and duplicates the journal’s contents there.
  • Every day, Zapier pulls exchange rates and share prices from a Google sheet I run and transfers them to another excel spreadsheet where I run my NAV analysis for Yellow Cake (LSE: YCA, OTC: YLLXF) and Uranium Participation Corporation (TSX: U, OTC: URPTF).
  • I use it in conjunction with spreadsheets to create a portfolio management system. I have a blotter page where I add new trades. Zapier updates new quantities and cost bases in the main sheets automatically.
  • It periodically sends me my P&L and risk metrics, so I don’t have to stare at my spreadsheets. I note this does not work all the time!

Zapier works by creating a workflow every time a trigger event occurs in an application. Triggers include an updated row in Excel, a new workflow in Process Street, etc.  


I doubt this post will rank in my top 5 for popularity. That’s okay. People may be dialed into their processes already or might not be ready to take a hard look at their routines.

For others, however, I hope the tools and ideas covered in this post spark a review and optimization of their back-end portfolio and research management. The goal is to make these repeatable tasks as efficient as possible so you can focus on finding and vetting new ideas.

With the treasure trove of information on rationales, expectations, and outcomes in a portfolio, investors can more easily and fine-tune their investing rules, a virtuous cycle if there ever was one.

If you’ve found this article or any others I have put out, please share it with friends or colleagues. 

The Castaway Capitalist

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IMPORTANT DISCLOSURE: As of the date of publication, the Castaway Capitalist maintains a position in YCA.

Disclaimer: No content on this website is intended to provide personal financial advice. This information is provided for information purposes only. We are publishers and not financial advisors. You should consider your personal situation, conduct your own analysis, and consult with a licensed professional advisor before making any investment decision.  No content on the site constitutes – or should be construed as —  a recommendation to enter in any securities transactions or to engage in any of the investment strategies presented here, nor an offer of securities.