Why I started using a brag document (and you should too)

Two things I struggle with:

1. Remembering what I’ve done.
2. Sharing my wins.

Keeping a brag document has helped me with both.

Here’s the story of how and why I created my first brag document, and how that evolved into building a tool to help anyone create one.

I couldn’t think of a single thing I did

I got pretty lucky with my first couple of "big boy" jobs. I got my first one after freelancing for a company, and the second one from a connection I made. So up until that point, I hadn’t had to go through a traditional interview process.

My skills and relationships did the work.

But when I was ready to leave my second job, I was officially in the job market and had to go through the formal application and interviewing process.

When I would jump in on interviews and people would ask, “can you tell me about a time when you did xyz?” I scrambled to come up with something that sounded somewhat coherent.

It wasn’t that I didn’t have the experience. My problem was that I could only remember a few highlights, but not the more detailed work I accomplished.

And it turns out that those smaller, more nuanced stories and experiences can make you stand out during interviews.

After a couple of rounds of that, I started jotting down any significant wins I could remember in a Google Doc and even took some screenshots as proof of the results I got.

It wasn’t anything fancy. In fact, it was pretty bad now that I look at it. I didn't even know what a brag document was at the time.

Eventually, I landed a new job and completely forgot about that Google Doc. Since I had a new job, I figured I didn’t need it and abandoned it for a few years.

I sucked at telling my story

As someone who's literally built a career on the ability to make boring topics sound interesting, this is embarrassing to admit.

But when it comes to turning my work wins into a compelling story, I haven't had the best track record.

To be fair, early on in my career, I didn't get much practice.

I’ve mostly worked for startups that didn’t have formal performance reviews. OKRs, 360-degree reviews, and other performance evaluation methods were new to me.

So when I actually needed to do them, the only thing I had to work with was my memory.

I remember looking through old emails, Google Docs, Slack, and anywhere else I could think of to piece together everything I accomplished during annual reviews at one job.

It was a struggle, and I usually could only track down large projects I worked on. It was enough to get an occasional pay bump, but I did a terrible job of advocating for myself.

Hindsight is 20/20, but I know if I had learned how to tell the story of my wins more effectively, I could’ve had more growth opportunities early on.

I needed a consistent way to track my wins

I didn’t realize the two problems above until after I reflected on them. In the moment, they were just temporary problems I was trying to address.

As I’m sure some of you can relate, my focus was on doing my job. I rarely paused to think about or document my wins along the way.

In fact, I didn’t get serious about tracking my wins until the past couple of years. And even then, there has been a lot of trial and error.

I already told you about my failed Google Doc. But I also tried a version with Notion. I stuck with that for about a month or so, then stopped because it felt like a chore.

Then one day I stumbled across the idea of a brag document. This post from Julia Evans, in particular, got my wheels turning. The idea of a living document to track all your wins across your career seemed like a great idea.

Then I looked on Instagram, Reddit, and TikTok and realized I wasn’t the only person struggling with tracking my wins.

I started looking for the best way to create a brag document but wasn’t impressed with anything I found.

I saw templates that I knew I wouldn’t keep updated, and people suggesting things I’d already tried, like Google Docs and Notion.

That led me to create Brag Doc. A free tool that makes it easy for anyone to build a brag document.