Use Obsidian to track your work history
I’ve been using Obsidian for over a year. I spent months figuring out how to structure notes and get the most out of my second brain. In this series I’d like to take a whistle-stop tour of some of the specific areas where tools like Obsidian can be really valuable. There are a ton of blog posts and videos out there preaching about how great it is to have a “Second Brain” capable of storing all your thoughts and ideas. Putting all your ideas into an app is quite a commitment if you aren’t sure of the payoff!
I use Obsidian to track my work history. Every major project goes into my vault (Obsidian’s term for all your notes). Having just landed a new job, I can say with confidence that this was incredibly valuable. ext time I need to find a job, it’ll be even better.
Why track your work history at all?
Think back to the last time you were applying for a new job or a promotion. Would you say you were adequately prepared? Was it easy to find all the information you wanted to gather? Was it a positive experience? Or did it feel like a huge struggle? For me, it was definitely the latter. This is where a brag document can come in handy.
The idea is simple. You write notes each time you finish a project. I’ll leave it up to you to decide what constitutes a “project” - it could be a huge year-long upgrade to a system, or something you spent a few hours on to help someone else out. Essentially, anything worth bragging about.
Then, whenever you need to dig out this information, you have it all to hand. And you will need to dig out this information. Whether it’s applying for a new job, putting yourself forward for promotion, or going through a scheduled performance review, you will have to answer “what have I actually achieved?”
Why Obsidian?
Similar to the recommendation tracker, the key reason is bidirectional links. You can build up two lists in parallel. One is a list of “evidence” - your contributions and achievements over time. The other is a list of “skills”. As you advance through your career, different skills will start to be more important. Each of your achievements might demonstrate multiple skills. You might (and probably should!) have multiple pieces of evidence to back up each skill you possess.
There’s another benefit to Obsidian, which is portability. An Obsidian vault is stored as a local folder full of Markdown notes. Markdown is a widely supported plain text format. That means your notes are built to last. Unlike a SaaS platform like Evernote or Notion, there’s no risk of having the rug pulled out from under your feet. Your data belongs to you! Given your career will last for decades, you want confidence that your work history notes will last too. (Make sure you back up your vault)
You might wonder how this note collection is different from your CV. Your CV is a linear document designed to give bullet point highlights of your greatest hits. The brag document can fit a lot more detail. It can also be a lot scrappier. As you advance in your career it becomes more important to tailor your CV for each job application. You need to select evidence that matches the skills that the hiring manager is looking for, even if that means cutting some of your proudest achievements. Don’t worry though, the brag document is a goldmine for interview prep. Can you say the same of your CV?
OK, so how do I get started?
The best time to start is right now! You can start small and add to the document over time.
Start with a single note: My working history. This serves as your entry point for the rest, to avoid things getting lost. You might choose to group this chronologically (to match the format of your CV), but you don’t have to.
Add a bullet point to My working history for each project, linking to a note for that project like - [[I upgraded the Billing Service]]. Note the “I”. This helps you focus on your own contributions, rather than writing a report of the whole project. This is no place to be humble!
If you find a note getting too big, you can split it apart. Maybe you end up with a note like I helped Jill get comfortable with FastAPI. You can use bullet points, full sentences, or a mix. There doesn’t need to be a fixed structure. Extra nuggets of concrete data are super valuable here - these are exactly the kind of thing you’ll forget. It could be quantitative (Reduced deployment time from 10 minutes to 2 minutes) or qualitative (Customer said the new workflow was "a joy to use"). Make sure you include enough context so that you’ll remember later: Made it 5x faster might make sense now, but will you still know what exactly was 5x faster in 6 months or 6 years?
Now that you have a bank of evidence, you can start building up a bank of questions. Write one note per question. These can be things like “Tell me about a time a project didn’t go to plan” or “Tell me about a time you set effective goals for your team”. If you’re not sure where to start, try searching for a list of “most common interview questions for [your job here]”. If you’ve set any goals with your manager, you could list your current goals as questions too.
As you add new questions, find and link a few pieces of evidence to help you answer. You can add any extra context here. It might also remind you of old projects that you haven’t included yet. If you’re struggling to answer a specific question, maybe that’s an area for you to work on.
As you add new evidence for each project, think about where you contributed, and which questions it answers. Did you focus on mentoring? Did you have to act quickly when circumstances changed? What went well? What went badly? What did you learn?
I hope it’s clear how valuable these notes can be. The payoff will only increase over time. You’ll be able to go into your next interview or performance review with greater confidence. You can learn to spot gaps and have better career conversations with your manager. What are you waiting for? Go write that first note!