Stack Your Apps for Maximum Productivity

I stopped chasing an all-in-one solution and instead built a stack of the best tools for the job.

I was always trying to find the best way to squeeze my whole life into one application. While I honestly believe the more connections built in a Life Operating System (LOS), the better, I felt I was constantly pushing the boundaries of tools too far, trying to get them to be all-in-one systems.

Therefore, I decided to drop the assumption that one app can cover the entirety of life and pick the best product for the job. I am embracing a ‘stack’ methodology. In the IT world, what technologies you use are typically abbreviated into a ‘stack.’

For example, a top stack for 2020, the MEAN stack, consists of MongoDB, ExpressJS, AngularJS, and NodeJS. I have stopped trying to stretch things beyond their purpose and instead have stacked several products together in my LOS to ensure I use less time tweaking tools — and more time getting stuff done.

How I Learned About Productivity Applications

I learned the world of productivity software through my corporate job. When in school, pen and paper were my only means of organization — and it seemed to work for my education.

When I entered the workforce a decade ago, I saw the impact technology could have on productivity. For example, I oversaw the implementation of an ERP system for a boatyard where we could predict material costs for next year’s budget forecast in one click, given that we were able to log each ounce of epoxy resin used. Previously it was just a shot in the dark based on those who had been in the yard for decades.

The scope of my programs increased from one boatyard to multiple continents over time, and so did the scale of the applications required to run them. I took the opportunity to try out many different tools to facilitate change, given that my company did not have a hard and fast rule of which to use. I started in the Microsoft O365 suite (Project, Planner, and To-Do) and then moved to an application Product Owner role and implemented work through Azure, Atlassian, ServiceNow, Asana, and others.

But when it comes to running my personal life via a Life Operating System, I felt the large enterprise applications either too costly or too heavy just to run someone’s life. On top of that, these huge enterprise applications often lacked the flexibility to manage things other than tasks. How would I manage my OKRs coherently in JIRA? How could I save websites easily from the browser into a project database?

The Mistake I Made With My First Setups

Out of a desire to be as efficient as possible, the first mistake many make, including myself, is to try to find the one application that can fit your entire life into it. I spent years chasing this goal and several times came pretty close. However, the end outcome was my realization that if I wanted an application tailored to my life, I would have to build it myself.

I recently got the closest when using Notion for pretty much everything in my life except for specialized activities like banking. However, I was stretching the tool to its limits. Some of the features I had sacrificed became more important to me.

Below are some essential features that I have placed new importance on.


I have always been super privacy-focused, but not so much as to not have a public blog. I have been wary of putting health and finance information in anything not encrypted. However, I had horse blinders chasing the one tool to rule them all and put all my finance and health information into Notion. I have since deleted that, given their current encryption policies, and decided that the best course of action was simply pen and paper. Who wants someone to read your diary after they hack into a server with the password “solarwinds123”?


I enjoy supporting new companies. However, sometimes when you put all your eggs into a small company’s basket, their blackout becomes your blackout. I overlooked the first few blackouts with Notion, but it happened with enough frequency to put this requirement higher on my list than in past years. As detailed below, though, a particular job might be okay at lower reliability, making the trade-off easier. Still, things like task management require much higher reliability for my LOS than a note-taker.


I love tinkering around. In Notion, I extended it quite a bit through scripting and custom visuals. However, Notion and many other tools looking to replace all your applications often deprioritize integrations. This deprioritization is okay when you are looking for an all-in-one tool. Still, once the assumption of an all-in-one tool exists disappears, the available integrations and APIs become paramount.

I removed the illusion that I would ever reach a perfect all-in-one tool and instead went down a path of job stacking.

How I Started Looking at Tools Differently

Once I let go of the all-in-one illusion, I decided to take the “jobs to be done” approach. This framework was popularized by Anthony Ulwick and culminated in his book “Jobs To Be Done” (free ebook here). In a nutshell, it’s the idea that product owners should dig deeper than the product and focus on the needed outcomes. For example, someone building a house might be more invested in a water-tight foundation with a 500-year lifespan for their house construction (outcome) than simply a truckload of concrete (product).

So what are some of the jobs to be done when managing work (in your own life or job)? How does the landscape for tools look?

Note: Below are tools that I have personally used. I could have put hundreds more, but I just wanted to make sure I only showed my experience to have educated discussions with you if needed.


Job: I want to retain portions of media and make them available for future use.


notes productivity tools

Sometimes a highlighter is the best product to use. My fiancé makes fun of me because many of the books I read are literal textbooks, and when they are meant for reference and are in physical form, highlighting key passages is the easiest. Sometimes, after I have completed a book that I want to write further about, I type out my highlights into a digital tool like those above. Typing out my highlights helps me retain the critical information as well!

Goal and task management

Job: I want to reduce the administrative time required to manage my activities to ensure the majority of my time is for value-adding work. I want to always stay on course with my goals.


Task productivity tools

When organizing dozens of people across the world, sometimes the big players are the best. I have even run large projects in Salesforce of all things. However, personal projects lend themselves to more lightweight and cheaper options like those on the left side of the above picture. I have had high levels of success in Notion and Clickup for task management. When you put the upfront effort into designing the system, day-to-day work management becomes relatively easy!


Job: I want to present a consistent voice to the world across all my writing and manage all of my content in one place.


Communication Productivity Tools

There always are extensions and mini-tools that orbit the core tools you use. For example, I use Grammarly across most of my tools for writing and various add-ins for extensibility. I have used all but Samepage in the above picture but have fallen back on the Office 365 suite time again. But these landscapes provide a great foundation to intertwine all the other jobs!


Job: I want to plan and reflect on each day in a safe environment where I can be transparent. I also want to improve over time by revisiting my thoughts.


journal productivity tools

I have done electronic journaling most of the time, but I feel much more open and freer to write after switching to pen and paper. I enjoyed the structure of Day One and Goals Wizard. I also loved my templates for daily, weekly, and monthly reviews in Notion as well. However, the overwhelming feeling of fear I had about putting my soul into a database I had no control over led me to eventually revert to pen and paper. I am developing my journal to try this year as I have incorporated standard elements that help structure a productive review of the current course you are charting! Stay tuned.

Health, finance, and entertainment

I wanted to put these types of jobs to ensure we are not leaving out all the tools that we typically have to use for specific aspects of our lives. For example, finance jobs have their tools directly with banks. Health apps (which I appreciate now in Denmark) are usually standalone. Products like Plex and Netflix make up a cluttered landscape of niche tools that are not often integrated into the rest of your life. For a good reason, too, sharing health and finance information with more companies than required is one of the first reasons I abandoned the one-app-to-rule-them-all mentality.

Why Productivity Stacking Is Best

At first, partitioning your productivity seems counterintuitive. Won’t you be at a disadvantage having to switch back and forth between products? In my experience thus far, the answer is no. Given that you chose a product for a specific job, and I find I am most productive when doing one job at a time, I am typically only working on one or two products.

Another reason having a stack of products is not as terrible as it sounds is that many of these products invest in open APIs to increase interoperability. Available APIs are crucial for my previous thought process that the only tool that will fit all my requirements is one I build myself.

I envision that I will build my products to augment my stack. I have already looked into dusting off some old python projects to make some dashboard MVPs. I subscribe to the topic of making progress visible, and what better way to be able to extract essential information from your stack and put it on the family TV in the morning.

As I mentioned in a previous article, I envision that even managing our future homestead — and the products we use for those jobs — become inputs for a family dashboard where even the daily chores get allocated across the family!

mock productivity dashboard

Conclusion: Don’t Chase the Impossible “Life-in-One-App” Idea

Think about what job needs to be done, and find the best product for it.

Therefore, I dub my current Life Operating System stack as CONN (Clickup, Office 365, Notion and Notebook).

CONN Productivity tool stack

What stack are you using right now? Leave a comment below! There is no right or wrong answer; only you know what jobs are in your life.

#LifeOperatingSystem #Productivity #SelfImprovement #Project #Notion