Critical Habits & Behaviors — 2018 & 2019 (Part 1)

Part 1 — Three things from 2018

Unbelievably, 2018 is pretty much a wrap. It seems that every year has something to teach us, but 2018 had a few more lessons then I was expecting. Of course, challenges often bring change and I’m writing this post to share three personal behaviors I experimented with in 2018. In part two of this post, I’ll discuss a few changes I’ll be exploring in 2019.

Three behaviors/habits I tried in 2018

Habit #1: Networking as Practice

While I had historically approached network building as something that happened organically, I had an opportunity in 2018 to be more deliberate about my approach. It started in early summer when I emailed someone I had spoken with back in the spring. “Hey, we never got to talk after that panel in Austin, how about we grab a coffee and catch-up?”

His response was near-instantaneous, “I’d love to. I’ve got 2 slots open this month, how does next Wednesday at 8 AM sound?” I was instantly intrigued. “Slots open?” how deliberate was this guy’s approach to network building? I had assumed that he, a very successful local entrepreneur, would be incredibly hard to connect with.

When we met, I asked him how frequently he had coffee meetings such as this. The answer was “nearly every day” and in an instant, it all came together for me. I need to make network building a deliberate priority, not an afterthought.

Towards the end of our 20ish minute chat, I was equally impressed with how eagerly he listened to my story and opened his “Rolodex” to make a number of key introductions via email. This single conversation helped establish the core of my network building strategy around two simple rules:

Rule 1: Make network building deliberate, set a target number of meetings and proactively reach out to your extended network to fill them up on a weekly basis. I started by aiming for 2 meetings a week, typically coffee in the AM but sometimes an after work drink or lunch depending on the depth of our relationship.

Rule 2: Focus the conversation on them, catching up on their evolving professional life, if appropriate check-in on their personal lives. Most importantly, try to identify anything you can do to help. (Then do it.)

Over the following months, my tooling evolved. I started with a simple list of folks to re-connect with but quickly found a free CMS tool to more accurately track my contacts, follow-ups, and action items. But at the core, I’m still focused on the two “rules” laid out above.

Anecdotally the results have been impressive. I’ve deepened a number of personal and professional relationships, and I find these coffee meetings very rewarding. I accomplished the primary goal of my original networking push (to find a new employer) and also secured an introduction to a new client.

In summary, I networked like never before in 2018, and I plan to focus even more on this area in 2019. So if you’d like to connect (about anything), please reach out.

Habit #2: Discipline in Thought Leadership

For years blogging more frequently has been at the top of my new year’s resolutions, and despite a blog post here and there it’s one that typically fell by the wayside. In mid-2018 I renewed my commitment to blogging and I set a modest goal of 4 blog posts per quarter, a total of 8 posts before the end of the year.

I certainly didn’t hit that target. But I did post 4 stories on Medium with a 5th showcased on the Arcweb blog. If I publish this post before the EOY, I’ll have hit 75% of my goal. More importantly, the exercise of writing has taught me a number of lessons that I somehow missed out on previously. I’ll share some of my most important lessons below:

Lesson 1: Just start writing

One of the first things I did after I committed to blogging more frequently was to waste a few weeks fretting over exactly how and where I’d share my ideas. Should I just blog on LinkedIn? Should I set-up a simple WordPress website? Maybe I should blog on Medium? What even is Medium? Is their audience growing or shrinking? If I set-up my own blog maybe I could sell ads one day and make a few bucks. With absolutely no blogs written, every one of these lines of thought is a distraction and a trap.

One night in a fit of frustration (or moment of clarity, you be the judge), I just decided to start writing my first post in a google doc. When it was done, I decided to quickly set-up an account on Medium and get it into the wild. Turns out, that writing great content is exponentially more difficult than finding the right site to host it on. (At least for me.)

My advice here is simple if you’re just getting started, pick a simple platform and get writing. If you start to pick up steam, and decide that you should be on a different platform, or perhaps set-up your own website there’s always plenty of time to do that. Your small and growing audience will happily follow you anywhere.

Lesson 2: Write like an onion

I’m 110% not an expert on writing, blogging, or anything else in this arena. However one of the things that came as a surprise to me was how important it was to approach my writing iteratively. I wrote almost all of my posts this year in three or four iterations depending on how you count. Here’s how it typically went down:

Iteration 0: I don’t know if this counts but one of the habits that really helped was to keep a running list of potential blog topics at all times. I used a simple Evernote file and continually added new topics to it whenever anything occurred to me. Good ideas, bad ideas, other peoples ideas it didn’t really matter, I wrote them all down. This paid dividends when I was staring at a blank sheet deciding what to write about.

Iteration 1: From there I typically wrote an outline of the blog I wanted to write. Sometimes this was a simple set of bullets, other times I posted in links to other articles or a diagram I wanted to discuss. A few times I wrote out a few introductory sentences and outlined the rest of the article’s headers and sub-headers. Just getting these ideas down on paper was a huge first step towards actually getting a post ready for sharing with the world.

Iteration 2: From a rough outline, I’d focus my next writing time on putting together a complete rough draft from beginning to end. Without the emphasis on that complete draft, I’d spend my time writing, and re-writing, my introductory sentences or first paragraph and never move on beyond there. Reassuring myself that I was going to have a chance to revise and edit my writing was huge. I simply needed to get the ideas out of my head. Perfection is the enemy of the good.

Iteration 3: After sleeping on my 1st draft, I’d take another complete pass on the article from beginning to end. At first, I was amazed at what I found. Sections that I thought were crystal clear read like complete gibberish, other sections had important insights that needed to be clarified or emphasized. I made structural changes, moving whole paragraphs around within the article to improve flow and readability. It was often this third iteration that transformed my writing from a combination of promising thoughts to a “blog post” with a discrete beginning, middle, and end.

For me, just writing these few posts really helped me discover how to write. 19 years of schooling had simply never drilled into me the importance of writing iteratively instead of simply starting at the beginning and writing till the end.

Lesson 3: Make it work for you

My third lesson-learned was that the entire process needs to work for you. Narrative writing isn’t something you can force (or at least I can’t) there were days that I wanted to write that I simply couldn’t get it going. Other days I didn’t plan on writing and yet I ended up cranking out page after page. If you’re sitting down and the words aren’t flowing try switching gears for a while and perhaps you’ll find a better flow at another time.

Just as important as well as to make sure you’re enjoying the subject and structure of the content you’re writing. Just a month ago I realized that I was so focused on striving for a specific number of posts that I wasn’t writing the kind of content that I might like to read. I had actually written a post that I never shared simply because I wasn’t happy with the subject matter. In 2019 I’ll continue to pursue thought leadership through a number of channels but I’ll be re-focusing the topics I discuss.

Check back here in early 2019 for more insight into the subject matter and formats I’ll be prioritizing for the next 12 months.

Habit #3: Daily Journaling

Another daily habit I added in 2018 was a commitment to daily journaling as a form of deliberate goal setting, and as a strategy for self-accountability. Inspired by a variety of sources I mushed together a number of approaches until I found one that worked for me. Here’s where I landed:

My journaling practice was more about deliberate goal setting then it was reflection and processing of the previous days’ events. Each afternoon I completed my journal entry for the next day which was primarily composed of 4 sections.

A template of my “daily journal”

Section 1 — My Long-term view

Each day I re-wrote this single sentence starting with “James is…” Although it evolved over time this sentence lately has resembled “James is a techno-optimist, helping companies tackle big challenges through digital technology.” Although re-writing the same sentence on a daily basis seems quite inefficient I’ve found it a helpful daily reminder of what I’m most passionate about. (More information on my personal optimism around the potential of technology coming in early 2019)

Section 2: My Goals & Priorities

If section 1 is an open-ended and unbound vision of my “future self” the 4 boxes that dominate the page help articulate the specific steps I believe will move me towards that vision. In each box, I’ve set three goals or priorities for a given timeframe (Quarter, Month, Week, and Day) and refresh each one accordingly. Every day I set three priorities for the next day which should align with the 3 goals I set for the week, which should feed the 3 goals I set for the month, which should get me closer to the 3 goals I set for the quarter.

Yes, I also re-write each of the goals every single day, which means that I write down my quarterly goals a total of 90ish times between when I establish them and when they’re complete. Again I believe this deliberate approach really helps my priorities stay top of mind as I work through each day. There are also many many little things that aren’t important enough to even make my daily priorities list and I track those separately via Asana. We can talk about that at another time.

Section 3: I Still Don’t Know

In my picture I’ve titled this section “I still don’t know what to use this space for!!!” and it’s true.

I’ve tried using it for things to remember, lessons learned daily, random meeting notes, and none of these options has felt quite right. Most days I simply leave this section blank although I’m going to experiment with taking a bit more time to actively reflect on each day here.

Section 4: Daily Habit Tracker

Across the bottom of each page, I’ve listed a number of additional check-boxes that I use to track important behaviors daily. The 5 things I’m currently tracking down here include:

  • Workout: Did I complete my daily workout?

Most days I get to check nearly all of the boxes in this list, and again they are just simple reminders of what my priorities are.

I’ve found this daily practice incredibly helpful in 2018 and I plan on carrying it forward into 2019 as well. Even on the days where I forget to check off the boxes that are complete, and despite that fact that I’m not doing anything fancy with the “data,” I find the act of writing down these priorities has been a great focus.

2018 Wrap-up

For me, 2018 was a year in which I was more deliberate than ever about crafting the habits and behaviors that I believe will help me be successful. Obviously, the jury is still out but I feel each of these has been a positive addition to my life in their own way. I plan to carry each of the 3 forward into 2019, still continually looking to optimize each.

Check out Part 2 of this post in which I share three new behaviors and habits I’m working on in 2019.

Helping companies navigate technology-driven change.