You will be both your biggest critic and your biggest fan. This is because you, like everyone else, are a human being, and human beings are selfish. It’s not inherently bad that people are selfish, but it is human nature. So, when you approach how you interact with people, people won’t be chomping at the bit to let you know how excellent you are.
This is why you need to learn to sell yourself, without coming off as a boor. Letting people know your accomplishments in a way that’s refined is GREAT, because people will better understand what you can bring to the table. Failing to talk about the things that you’re good at means people will rely on stereotypes and first impressions, rather than the substance of who you are.
With this in mind, the question is not if you’ll brag, but how you’ll brag. Obviously there are some boors, people who go on and on about their excellency, and they don’t let people get words in edge-wise. You don’t have to be this person, and many times sharing your story with appropriate decorum actually makes you appear more impressive.
First, try and think about the things you have to sell yourself. What are your values, goals, and accomplishments. What have you done so far in order to accomplish them? Thinking about this both allows you to realistically assess how you’re doing, and also to think about how to spin your story positively. You are your own protagonist, and you can have a hell of a story if you understand what’s going on around you.
Next, you want to start to contextualize your story in terms of your values, goals, ambitions, etc. Doing this is really great because you set up why you’ve done what you’ve done, and everyone loves a hell of a story. I’ve gone from A to B through C. Now, you fill in the details of this story, excluding that which doesn’t serve you. Finally, you learn to tailor your communications for the social setting. In a short discussion, you won’t blabber, but you may have a moment to introduce yourself. Learning which levels of communication work for which audiences will allow you to absolutely kill it!
Good luck, and keep boasting!