Purpose

I had been unhappy with my job, but I thought my company was great. I was looking for ways to introspect, both to debug my discontentment and consider my future career. A very competent and high EQ person suggested I think about the activities I like and dislike doing. I will use this post primarily to guide my career direction and also to explain some of my intrinsic motivations to others.

Defining terms

“Activities” in this context are categories of things that I do in a professional capacity.

“Liking an activity” means that doing the activity is rewarding and motivating. My skills are far more likely to concentrate around activities I like. It does not mean that the activity is a requirement for my job/career, but it will influence my career choices and performance on a given job.

“Disliking an activity” means that doing the activity can be demotivating and draining for me. For an activity I know that I dislike, I must have had enough experience with it to be wary and a good idea of how skilled I am at doing it. Again, this does not mean that I must avoid that activity in my job/career, but it will influence my career choices and performance on a given job.

Activities I strongly like

These are mostly in the areas of understanding complex systems. I find myself naturally gravitating toward performing these activities.

Understanding complex systems

Building mental models, often by extracting information. This is not building or changing complex systems, but those activities can be useful ways to develop an understanding of the system.

• Understanding how a company or department works - internal structure and processes of people.
• Understanding a tech product - use cases, underlying technical systems, history of changes.
• Understanding a person - what motivates them, what pressures they face, how they perceive the world.

Coaching

• Individuals - explaining to a non-technical colleague how to request a feature for our product.
• Teams - explaining a process I’ve seen in the past that may improve their performance.
• Activities - facilitating a meeting to ensure it is effective as possible.

Mentoring

• Career transitions - preparing someone for job applications (exploring roles/companies, guiding preparation strategies, cv review).
• Goal setting - recommending strategies and unpacking/improving goals.

Activities I like

These are mostly in the areas of building complex systems or collaborating. When I perform these activities, I enjoy myself and look for more opportunities to do them.

Building

• Software products - feature X for my product.
• Software frameworks/platforms - a framework for gradually automating expert tasks.
• Company processes - standardizing how customers are onboarded.

Summarizing

• Expressing mental models - documenting a product’s technical architecture.
• Explaining weaknesses of a complex system and recommending changes - explaining the solution architecture of how our product will be used by our customer.

Negotiating and debating

• A stakeholder requests a new feature for my product and asks when it will be delivered (negotiation + coaching).
• A problem must be solved by multiple teams and each have flexibility over how much they could contribute to the solution (negotiation + collaboration).
• In an enterprise integration, a customer’s tech team is incentivised to reduce the scope of their work by offloading it to your customer solutions tech team.

Activities I dislike

These activities are necessary for middle and upper management, so they will be unavoidable in my career.

Operating / maintaining

• Running the week-to-week of a team - making sure standups, retros, grooming, and planning happen and are effective.
• Monitoring and tuning the performance of a team - my team performed well on project X, but not project Y. I’m monitoring that this is the case and making changes.

Project management

• Resolving planning issues - project X is delayed, and this affects project Y so we have to figure out mitigations/risks and update stakeholders for both projects.
• Ensuring others’ work is on track - weekly check-ins with all the parties contributing to projects X/Y/Z to confirm they are on track.

Conclusions

I find a variety of roles interesting, but none of them are perfect matches or paths for my entire career.

As middle/executive management, I develop a great overview of the whole organization, but I miss out on deep understanding of systems/technologies that drive the company and are a source of great risk and uncertainty.

As a principal/architect individual contributor, I get a deep understanding of systems and many mentoring opportunities, but I miss out on understanding the whole organization.

As a consultant or solutions architect, I get to understand customer companies in my domain of expertise, but I’m not getting the deep and holistic understanding of my company that I would be getting in management or individual contribution roles, reducing my future ability to coach companies or mentor executives.