202206122047 Career checkup template

Sourced from Will Larson's blog Irrational Exuberance¹

This is a simple template for checking in on your career. Here’s how to use it:

1. Look through the sections. If there are any sections that don’t resonate with you at all (as opposed to just feeling hard to fill in), then remove or edit them.
2. Fill in the sections. Feel free to jump around to answer the parts that you have the most energy for.
3. Revisit a few days later: anything you want to change after sleeping on it?
4. If possible, find peers or friends to share and discuss each others checkups together.
5. Store it away somewhere to review a year from now.

Summary

Write this section last! How would you summarize everything else you wrote below? Try to keep it to max of two paragraphs.

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How are you feeling about your career right now?

Write a few paragraphs about how you’re feeling about your career right now. Don’t worry about writing this for consumption, focus on finding words that resonate with you!

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What did you expect / what happened in the last 5 years?

When you think back to five years ago, what did you expect to happen over the following five years? What has happened? How do you feel about the difference between those two?

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Things you’re proud of in your career

Add short bullets of things you’re proud of, why you’re proud of them, and links if you have them! Don’t worry about editing down, just add whatever you’re proud of. If you’ve been working more than ten years, it may be helpful to think in buckets of ~5 years to help remember!

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What are 2-3 moments in your career that you cherish?

Write a few bullets capturing two to three moments in your career that are very meaningful to you. They may not necessarily have been the happiest moments, but they should be meaningful moments to you.

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Things you’re anxious about in your career

Add short bullets of things you’re anxious about in your career, and why you’re anxious about them.

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Who are some people that have impacted your career?

Write the names and some brief context of folks who have impacted your career in meaningful ways. (Consider reaching out and letting them know!)

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What are your most impactful sources of prestige?

Prestige is an important part of a successful career. What are the sources of prestige that have been most valuable in your career?

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What have you learned recently (in the last ~3 years)?

Ongoing learning is an important part of a meaningful career. What are some things that you’ve learned over the past few years?

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What’s your ideal career checklist

What are the things that you haven’t done yet in your career that you’d like to do? Don’t spend a single moment worrying about whether they’re attainable or what anyone else would think about them!

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What do you feel might be holding you back?

Many folks have a long list of things they feel might be holding them back from accomplishing things that are important to them. What are the things that you feel like might be holding you back?

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What’s your biggest goal for the next year?

If you think about your current goals, as well as your ideal career checklist, what’s the most important thing that you want to focus on right now? Why this one? How are you balancing attention to profit, learning, people, pace or prestige?

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Is your work compounding?

It’s possible for the work you do this year to make the work you do next year even more valuable. For example, if you spend a great deal of time hiring and become more visible, it might be much easier to hire. Is your recent work compounding to create richer future opportunities for you? Is there an approach you could take to make it compound differently? Do you even care about this idea at all?

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What do you regret spending time on right now?

What are the things that you’re spending time on right now that you wish you weren’t spending time on? Why are you doing those things? Could you stop doing them?

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