How to Evaluate (Potential) Job Fit & Satisfaction

An unsolved topic that fascinates me when thinking about early-stage careers: job fit & satisfaction.

If you’re reading this, you’re a probably young keen bean looking to learn some interesting stuff, work on cool products with some semblance of “meaning” and do it with some good people by your side.

But how the hecc do you know if you’re in the right job for you (or if an opportunity is a good fit for you)?

Generally, there’s a gut feel around these things, but throughout my working life as a student, I found that by formalising and regularly assessing my core drivers for job fit & satisfaction, I was able to make better decisions about:

Here are the 3 key factors I use to think about these areas.

  1. Learning

What sort of skills and knowledge do I want to build, and how quickly am I learning these?

Early in your career, the importance of learning is almost a cliche. There are two facets to learning that I think are helpful to think about more deeply:

  • Velocity of learning: This is probably the factor that people tend to jump to when they think about learning. How much/how quickly are you learning, and is this slowing down or plateauing? In the first few months of a job, the learning rate is usually relatively high. A lot of jobs will teach a great skill initially but then regress to more incremental optimisation, whereas others continually provide a high learning rate across distinct skills (especially helpful early in your career).

  • Alignment with nature of learning: You might be learning a ton of things, but are you learning the right things? With any role, consider not just learning volume, but what things you want to learn in the first place. Critical to this is the idea of leverage: are these skills and knowledge things I can extensively utilise in my desired future path and projects, or will they be forgotten and wasted?

  1. Impact

What sort of problems do I want to build solutions for, and how much impact am I having over these problems?

Similar to learning, the impact you have in your work should be considered both in terms of type and volume of impact. Here are three key dimensions to evaluate:

  • Alignment with nature of impact: What type of impact do you think is worth making in the first place? Not all industries and problems are created equal, and so there’s some soul searching to be done on what pain points and problems you most want to spend your time on. My general qualitative guideline here is to find problems that piss you off and find companies that you think are remedying these problems in the most effective way.

  • Degree of collective impact: What is the overall tangible impact of my entire company’s work collectively on the intended problem space? How many people are we affecting (niche or general appeal, local or global scale) and what is the average net impact on each of those people (mild benefit vs. life-changing)?

  • Degree of individual impact: What margin of impact am I having on the company? Does my role make a significant individual difference to core decisions around customers, product development, marketing, investment, and so forth? How would the company trajectory differ without me?

  1. Camaraderie

What sort of people do I want to build things with?

Learning a ton and working on a really cool problem with high impact doesn’t always guarantee fulfillment at work? For me, the biggest remaining ingredient is whether I have a sense of camaraderie (mutual trust and friendship) with my team i.e. I enjoy working with these people specifically, putting aside skillset and problem space. When shit hits the fan, being around people who you respect & trust can really help you push through tricky problems:

The core drivers of these relationships? Everyone will screen for different traits, but for me, the six most important characteristics in the people I want to be around are:

  • Honesty

  • Intellectual curiosity

  • Openness

  • Kindness

  • Ambition

  • Self-awareness