On Thursday, January 2, 2025, I logged into work. I was six months into my role as Director of Engineering for Tessian, a business unit within Proofpoint, US-based cybersecurity company. While Americans take work seriously, Tessian is UK-based, and I’ve discovered Europeans take their holidays seriously. I was completely alone. Also, who in their right mind starts a working year on a Thursday??
At the six-month mark, I finally felt I’d successfully navigated the onboarding firehose and finally got to a point of keeping up with the daily demands of the role. Since I literally had nothing else to do that day, and it was second day of a new year, it was a perfect time to step back and think through my professional goals for the year.
I opened my journal, touched pen to paper, wrote some words, and… nothing.
Fortunately, I have a career coach I can now call upon at anytime. I opened a new prompt, outlined the situation, and asked for help. The coach came back with a solid framework:
- Define a theme for the year
- Identify high-level aspiring goals
- Break those into SMART objectives
It sounded great and got me excited. Armed with this structured approach, I went back to my journal, touched pen to paper, wrote some words, and… still nothing.
This is where I reached for method 2 in my AI as a Thought Organizer playbook. I returned to the chat and typed: “Give me a set of questions I should think through as I’m working through my goal setting.”
The coach generated ~25 questions across six categories. I pasted them into a Google Doc and spent over three hours doing an unfiltered brain dump. If I didn’t know the answer to a question, without slowing down, I’d just type “I don’t know” and proceed to explain why I was struggling.
When I finished, I pasted the massive document back into the same coaching session.
The output was nothing short of pure magic.
It took the disorganized thoughts bouncing around my skull all day and structured them. It echoed my own voice, interests, and desires back to me, articulating them better than anything I could have managed on my own.
This wasn’t the usual box-ticking exercise HR teams force upon everyone. It was the exercise HR hopes we do. I didn’t do it for them; I did it for myself, and I ended up with personalized goals and aspirations that were actually meaningful to me.
I got so excited by how well this process worked, I spent the following Saturday applying the exact same method to my other 5 core pillars (*) For each one, I began with, “If 2025 was a great year for X, what would have happened?”
Having on-demand access to a thought partner and a coach is the exact reason I discovered Kayak Ontario. That led to meeting some amazing people and joining them in March 2026 for a sea kayaking trip off the coast of Brazil. Never in my life did I think I’d end up in South America, but the trip was beyond incredible. And it all began on the first Thursday of 2025, just because I had absolutely nothing else to do that day.
* - Actually at the time of this exercise I only had a total of 5 core pillars in my my core pillars list. On that Saturday evening when I got to the end and I thought I was done, the agent all of a sudden replied, “great, now lets do your next pillar, Health.” At first I was taken a back and even asked agent to review our conversation and tell me what pillars I identified. It listed only the first 5. Then I asked, how did it come to the conclusion that I’d like to work with it on a 6th Health pillar. It reached into its own memory and gave me back a set of arguments that based on what it knows about who I am and what’s important to me, it believed I’d like to track Health as its own six pillar. Sadly, scary and funny enough, the agent basically won that argument and convinced me that I actually have six core pillars and not five.