Assessing Jobs Personal & Professional Fit

A deep dive on the framework I use for assessing jobs and future opportunities across personal and professional axes.

Photo by Ben Wilkins on Unsplash

I recently appeared appearing on The Courage Effect, a radio show/podcast hosted by my friend Suzanne Weller. I believe that the way to find a fulfilling job is to test and test and test some more. With Suzanne’s show, I was able to test three things:

• Public Speaking - something I used to enjoy but hadn’t done in over a decade.

• Personal Storytelling - something I was curious about that felt riskier than speaking about my work in corporate sustainability.

• Listening to Myself with Grace - I’ve avoided listening to myself. When I have in the past, I focused on the negatives. This time, I emphasized listened for the high notes, though I still noticed things I could’ve done better.

I went on the show because I had something to share. In particular, I wanted to explain the Can’t to Love Framework I use to assess jobs and career opportunities. In this post, I go into the framework in more detail.

There are two axes: Personal and Professional. Each axis runs from Can’t or Won’t to Could, Can, Like, and Love. Here’s how I define the steps:

• Can’t or Won’t - this is a bright red line I won’t cross. Right now, taking a job that requires me to be away from my family every week is a no-go.

• Could - this is something that I could talk myself into if I squint hard enough. I could spend all of my time building Excel models. Am I great at it today? No. Does it drain my energy? Yes. But could I do it if forced to — I think so.

• Can - this is something that I can actually do. For example, I can (and do) work at a job that’s fully remote and occasionally requires me to take calls early in the morning or in the evening. On the plus side, I have lunch with my baby and kindergartener everyday. On the down side, I miss the energy that comes from collaborating on a hard problem with colleagues in real life. Things in the can column don’t drain or energize me — they just are.

• Like - this is something that brings me joy and energy in moderation. For example, I like editing, but I wouldn’t want it to be all I do.

• Love - this is all about getting into flow. This could happen when I’m writing an article, solving a problem at a whiteboard with colleagues, or finger walking with my baby daughter. I lose track of time and feel at my best.

Now let’s bring the framework to life. When thinking about my current role or considering a change, I start be placing dots on the graph where my current role is and where I think the other opportunity will be. Every six months or so, I do a self check-in to see how the role and/or my preferences have changed. This keeps me aware of how I’m learning and growing—and helps prevent me from becoming complacent in a role that drains my energy. Based on a lot of reflections, I’ve developed the following color scheme:

• Grey - this is a hard no for me, but opportunities on the cusp of grey and light yellow can be hard to pass up. For example, I considered a job under a leader I deeply respect that simply can’t work for my family. It was intriguing enough that we explored shifting the requirements into my personal could zone. It wasn’t possible for that role, but we both left that engagement with a clearer sense of what could work for me should a new opportunity arise in the future.

• Red - this is the danger zone. There are many things I can/will do in this zone for a certain amount of time if I am confident I’ll have an opportunity to move into a more hospitable color. When I started at Amazon, I worked in retail. I could do my job well — I even liked parts of it — but it wasn’t good for my mental health or relationships. It was in the red. After about 18 months in retail I was offered an increase in scope that would’ve lead to a promotion. I was a decade older than my peers, so a promotion was intriguing. But I knew that taking the job would lock me into the red zone for longer—maybe way longer if I accepted being in the red zone. After waking my wife up with my anxiety dreams, I decided to turn down the role, which eventually allowed me to move into sustainability, where I had some time in the blue zone (not all, but some—and it was great).

• Yellow - if I find myself in the yellow zone, I start thinking seriously about running an experiment (see Always be Experiments for details on how). I found myself in the yellow zone trending to red during the pandemic (didn’t we all?). After a few months of two jobs with two small children at home, aspects of my job that I could handle previously moved to can’t. Something needed to give for my family, so I resigned. This allowed me to test teaching remote kindergarten (fail), working with a career coach (win), living without a paying job (wow is it hard), and landing roles that’ve allowed me to test professional identities (win).

• Green - this zone feels the most personal to me. Some folks are satisfied in this zone, others aren’t. When I’m in the green zone, I start looking around for ways to move closer to blue. If I notice myself drifting towards the red or grey, I get more serious about considering bigger changes.

• Blue - if you get here, stay as long as you can. This is where you’re in balance, contributing at work and showing up how you wanted to personally. In my experience, it’s hard to stay in the blue zone. Perhaps it’s because I’m restless.

What do you think? Is your color coding different? There is no “correct” color schema or definition of each stage in the progressions from Can’t to Love—these types of frameworks are meant to be both universal and highly personal. For me, the key is findings tools that help me be the person I want to be and reach my goals.

Please let me know if this model resonates with you and if there are any other parts of my conversation with Suzanne that you’d like me to unpack here. As always, thank you for reading.