Work Journaling

Toward the tail end of last year, I started keeping a work journal. For as long as I can remember I’ve always maintained a journal about my personal experiences, but a work journal is a new endeavor for me. I started a work journal for three reasons. First, I want to be more deliberate about documenting things I learn from others within my firm and within my industry. Second, I want to develop a set of principles to follow when I encounter circumstances in the future that are similar to circumstances I face in the present. Lastly, I want to pass along what I learn to others who come behind me so they have a head start in whatever they’re endeavoring to do. 

I first started journaling after I graduated college and entered adulthood in May 2005. I mark my entry into adulthood (i.e., the real world) as the day I could no longer wear pajama pants outside because I was no longer going to an on-campus class. I was now going to work. My first journal entry as an adult was on September 15, 2005, and it was titled “Goals for the next four months.” My wife and I had just moved to Chicago, so my top goal was to ‘build new friendships’ followed by a slew of other items including ‘start a side business,’ ‘participate in an investment club,’ ‘make a 20% profit in my brokerage account,’ ‘take drum lessons,’ and ‘start a scholarship fund for my high school.’ I had a lot of things to get done in four months! LOL. 

I’ve journaled (mostly) every day since then. I enjoy going back and reading about the things, people, and places I’ve experienced. Some experiences were great, some were sad, and some of them were priceless. My experiences are no more unique than what other people experience, but what makes them valuable and useful is having the opportunity to look back and learn from those experiences to hopefully do things better in the future.  

It is with this mindset that I started keeping a journal specifically for work. Over my professional working years, I have extemporaneously kept a record of accolades I’ve received from co-workers or written down insights collected at various conferences or from industry peers. But I have never deliberately journaled about my own achievements, setbacks, and mistakes so that I could go back and study them at a later date. Like most people, I simply tried to remember what I did well and repeated it. Or, remember what I did wrong and tried to avoid making the same error.  

I’m reading a book right now called Thinking in Bets, by Annie Dukes. One of the concepts she discusses at length in the book is the concept of resulting. Resulting is when you look back on the outcome of a decision to determine whether or not that decision was wrong or right. The problem with resulting is that it is riddled with bias and it prevents you from properly assessing when to separate luck from skill. When things work out in our favor, most people attribute that to skill (especially in professional environments). Contrarily, when things don’t work out in our favor, we attribute it to (bad) luck. Annie states that in reality it’s a combination of the two (skill and luck). When we succumb to the allure of resulting, we don’t learn as much from these experiences because we don’t take the time to reflect on the ‘why.’ As it pertains to journaling about our experiences, I find adopting this frame of thinking exceptionally valuable because it forces us to think about what we’ve learned versus congratulating or beating ourselves up about the outcome of our decisions.  

My process for work journaling is separated into two parts. First, I have a Word document on my desktop that I use to write down specific operational tactics and procedures that are helpful in my day-to-day job. The things I write here are generally rote, but are helpful in creating consistency and intentionality for how I do them. For example, I created a list of quantitative and qualitative due diligence items that are commonly used in my industry when making investment decisions. This list is comprised of things I’ve learned from my own professional experiences, things I’ve learned from my colleagues, and things I’ve learned from others within the industry. I don’t write in this journal every day because its content is largely driven by specific operational tasks or tactics that occur with irregular frequency. I find myself writing in this journal probably two or three times a week. 

Second, and probably more important, I keep a separate journal that I write in at the end of each day where I reflect on conversations I had, emails I sent or received, feedback I was given, conversations I listened to, or situations I observed. It is from these experiences that I reflect, collect, analyze, and document things that I did (or said) that went well and/or document things that didn’t do well that I would like to improve on. I’ve only been doing this style of journaling for a month now and I feel like I’m learning so much more (and learning things faster) because I’m deliberately challenging myself to catalogue what I’m learning versus relying on pure memory.  

Ray Dalio wrote a book about his process of work journaling that established the foundation for his most popular book, Principles. I read this book when it was first released in late 2017, but to my chagrin I didn’t think to emulate his philosophy of journaling into my own professional life in the way he was at his firm, Bridgewater Associates. 

I’m super excited about the year ahead and I look forward to the process of documenting what I’m learning in all aspects of my life so I can do things better and be a resource for others. If you choose to start journaling about your work experiences, I’d love to hear what you’re learning. I personally believe there’s at least one thing we can learn from everyone, so hopefully we can exchange ideas over the course of 2021.  

Cheers – KM 

Photo by Thomas Martinsen on Unsplash 

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