Get comfortable being uncomfortable: Learning the art of the humble brag

Do you know what the four words that are, more often than not, the most daunting you can hear when you meet someone for the first time?

Before I tell you: think hard about what it’s like to meet someone for the first time and want them to get the right impression of you.

What is the process like for you? Do you have a formula on how you’ll introduce yourself?

This is how an introduction typically goes down: You shake hands, you introduce yourself by your first name and title, and then your new colleague/friend asks you….

Tell me about yourself….

And there it goes.

The bomb has been dropped.

There is no turning back…. You now have to answer one of the most open-ended, vague, and slightly awkward question anyone could possibly ask you – especially if there’s a job on the line too.

This question can immediately send many of us into heart palpitations. As in call “CODE BLUE, 911, I need an ambulance because this question is terrible and I don’t know how to answer” kind of palpitations.

How in the world do you begin answering this dreaded question?

Do you talk about where you grew up or which college you went to? Which job descriptions should you start memorizing to blurt out when answering this question? Do you talk about your nephews or your cats or your recent vacation to Seattle? Do you talk about your favorite shows on Netflix?

Believe it or not, THIS basic question is one of the biggest hurdles many of the clients I work with struggle to face and answer confidently.

In this blog, we’re going to talk about how you can overcome your fears of sounding “braggy” so that you can truly sell your skills during an interview while simultaneously (and confidently) NAILING this conversation starter.

First things first: Accept that this is new and will require some work

There are a ton of reasons on why talking about yourself can be so tricky.

First: no one ever teaches us this stuff. In the hundreds of courses I’ve taken, I never came across a class that specifically teaches us how to master the HUMBLE BRAG.

Second: many of us don’t invest the time it takes to really think about our skills, solidify our goals, or create a true vision for our career. Many of us jump the gun, put together a fancy resume, apply to jobs online, and think that our education or in-job-training is enough.

And, lastly, when it comes to talking about yourself, there’s a HUGE difference between how we feel talking to our friends or family and how we feel when talking about ourselves to employers, clients, or prospective employers.

Having a basic understanding of what to say and when to say it is key to answering this question.

Next: Why do so many people feel weird talking about themselves?

Psychologically speaking, there’s a lot that goes on when it comes to the discomfort associated with someone talking about themselves.

Partially, the problem lies in someone not wanting to sound like they’re bragging about their experience. Another speed bump lies in anxiety and a fear of being judged negatively.

Another reason that talking about yourself, especially in a professional setting, is so difficult is the way that professionalism tends to place a filter on our true selves.

Suddenly, we have to narrow down years and years of experience and figure out what to say in just a few minutes. On top of that, we need to make sure we don’t talk too much or too little to give the interviewer the wrong impression. And don’t forget to inject some personality in there without becoming too overzealous.

It’s a balancing act that can be much more overwhelming and scary than it needs to be.

When it comes to overcoming this anxiety, it’s important to understand that the issue isn’t that you don’t have, or don’t know, what to say – you just need to find the right way to articulate it to give yourself the credit you deserve!

And that’s where practice comes in.

Getting Over the Awkward Stage

It’s safe to say that the public speaker you look up to, who talks about themselves and their accomplishments effortlessly, also felt uncomfortable about it at some point (including myself!).

The more you prepare for the “tell me about yourself” interview prompt, the more casual and informative you can be with your response.

If you can work on, or get over, the fear of “SELLING” yourself, versus simply explaining yourself ad hoc, you’ll be able to get the results you want (that new dreamy job!) while solving your panic problem at the same time.

For people wondering how it’s possible to become comfortable talking about yourself, you should ask yourself: what’s at stake if you don’t gain the courage and confidence to get your point across?

Trust me when I say that the discomfort that comes with practicing your “This is Who I Am” speech, and rocking it in-person, is worth that dream job you want!

In the past, I had no solid approach on how to talk about myself. I would start talking about where I grew up and somehow end up talking just about my rescue dogs. In other cases, I’d rapid-fire different facts, stumble over my words, and sometimes forget to talk about my professional life. Thinking about this actually makes me cringe because it was just SO BAD.

So, how did I stop that cycle AND how do I coach clients to practice to specifically NAIL this question?

The answer is simple: PRACTICE. Being able to get comfortable in uncomfortable situations is typically a skill that can’t sprout up overnight. You need to allow yourself the space and time to get used talking about your skills, your values, and your vision for your career.  

Learning the Art of the Humble Brag

Instead of dwelling in anxiety and hoping for the best, it’s time to change your perspective. When I went through this shift in attitude, I needed to ask myself a few difficult questions, which I’m going to share with you now.

My magic formula on how to NAIL the “so, tell me about yourself” question is pretty simple.

Take a moment to answer these three questions below.

1.     Who are you?

2.     What are you currently doing?

3.     What are you trying to transition into?


There you go!!

Once you have all of these questions answered, it’s time to craft a story.

As I pointed out, mastering the humble brag doesn’t mean that you are downplaying your skills. Instead, you want to craft a good narrative about why you’re a skilled and valuable professional as well as someone who would fit in great with the team.

Stating the facts IS NOT bragging. Talking about your strengths is NOT interview suicide!

Remember: prior to going into an interview, or meeting a key stakeholder for the first time, it is critical you solidify this story about yourself.

Make sure that you’re acknowledging all that you can and practice, practice, practice until you feel as comfortable talking about yourself to a potential employer as you do with your friends!

Ashlee Klevens Hayes2 Comments