What Really Matters to You?

Are you making career decisions based on what’s really important to you, or are you playing it safe?  Are your priorities driven by internal values or are you overly influenced by what others think?

Are you relying on your cocktail party cred?

Have you ever been to a party and told someone you barely know about your job? Did you find yourself feeling either some superficial swell of pride or an insecure twist in your gut as you told them? Five minutes later, that person may never think about you again, and yet, just their perceived reaction could affect our mood for good or bad.

When we haven’t thought about what really makes us happy, we default to chasing titles, status or money, and worry more about the reactions of others.

To really understand what matters to you, you need to think about the big questions:

  • Stephen Covey’s 7 Habits of Highly Effective People is one of the best frameworks we’ve seen for orienting yourself around what’s important to you and the “circle of control” that you can impact. Here’s a summary of some of the key ideas, but you owe it to yourself to read the whole thing.
  • Covey actually takes a lot from Viktor Frankel’s Man’s Search for Meaning, one of the 20th Century’s most important books on finding meaning in one’s life. While Frankel shares his harrowing experience in the Holocaust, you’ll come away inspired by his empowering vision around how every individual can find meaning in focusing on what they can control in themselves and their response to any situation.
  • Dan Pink’s Drive talks about what psychology has learned about intrinsic motivation and highlights Autonomy, Mastery, and purpose. His Ted Talk is here.

We’ll get more into some of these broader philosophic frameworks in a different post, while here we’ll focus on assessing what’s important to you in your job.

Getting More Specific – A Self-Assessment Guide

The above frameworks are amazing at the level of life philosophy and can apply to everything you do. We wanted to get more pragmatic with more specific questions to dig into around your career. For the below questions, take some time to write your answers or share with someone who knows you well for feedback.

What motivates you most in a job?

  • Solving complex problems and learning new skills.
  • Working with smart people from whom you can learn.
  • Having a sense of autonomy and control over your work.
  • Financial reward – this could be about financial security, goals you have for your family, money for starting your own thing, or future flexibility.
  • Working at a company whose mission is inspiring to you or whose product is personally relevant

What are your superpowers? What are you good at?

  • Think about your biggest strengths. Where do you excel? Other people can be a good signal here. What strengths come up repeatedly in your performance reviews? What do your colleagues come to you for help with?
  • We often focus on “fixing” our weaknesses, but this may not be the best strategy for either contentment or effectiveness. Research has shown that we are better off leaning into our strengths and where we can be exceptional, rather than investing energy into becoming pretty good at our weaker skills.

What kinds of roles and activities made you happiest?

  • Which roles or projects do you enjoy most? What activities move you towards that “flow” state where time flies and it doesn’t feel like work?
  • What kinds of work has had the opposite effect, feeling like a grind or a drain of energy on you?
  • Is it digging in with data or technology, or doing creative work around language, messaging or visuals? Do you like working individually or in a team with well-defined ownership and hand-offs or do you like fully collaborative, integrated work with others with looser lines drawn?

What size of company or team resonates with you?

  • Have you enjoyed smaller teams and projects that were in a formative stage? Did you like knowing everyone and having more fluid, broad roles? Did you like needing to be scrappy with limited resources but having the opportunity to tinker and experiment with something entirely new?
  • Or, did you like larger, more developed environments? Did you like scaling and optimizing an existing product? Your role may have been more specialized, but you had the process and resources to excel and do things the right way. Did you like the breadth of a larger org, with a wider world of people to interact with?

Do you like to be more of a specialist or generalist?

  • Do you like going deep into a topic and becoming an expert? Do you enjoy mastery in a topic area where people come to you for the answer? Do you want to progress by running a team in that function?
  • Or, do you quickly get bored in a given subject matter area? Do you like the feeling of being out of your comfort zone in a new topic and having to figure it out? Are you comfortable NOT being an expert while making connections between disparate areas?

These questions are meant to tap into your authentic reactions to your actual experiences as a guidepost towards what makes you happy. You can test opportunities against these factors and they can also point you toward trying a new type of role or environment.