Here are the side quests you need to level up and be more interesting so you can quit the boring conversations and take over a room with great stories.

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If we’re not careful, life can turn into a pretty boring slog.

The same weekday routine of morning rush, let your soul waste away at a job that doesn’t light you up.

Hurry home to eat the usual dinner options.

Bedtime routines for the kids.

Maybe trash TV (or even more work).

Then off to bed to get ready to do it again the next day.

Weekends aren’t much better.

You spend the better part of Saturday mornings at a field somewhere making small talk with other parents with boring lives while your kids kick each others’ shins in the soccer scrum.

They’ve got boring lives. You’ve got a boring life. So your conversations are boring as hell.

It’s just a rotation of “What are you doing next weekend?” in hopes of impressing someone else that you’re going to spend a couple of days at a random cabin somewhere doing what you’d otherwise be doing at home anyway.

But now you want a little more.

You’re tired of the boring conversations.

You’d rather be the dude at the soccer field that has interesting conversations.

The one that people enjoy talking to about new things because you’ve always got some kind of insight or story to tell.

I promise that you don’t have to travel to Belize to snort ayahuasca with some tribespeople before riding a donkey to the summit of a mountain to be more interesting (as fun as that sounds … don’t threaten me with a good time).

You can be more interesting by just applying a few simple practices into your day.

Let’s get into it.

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Do more interesting things to be more interesting

I have the experience of being on live television. Of talking about sports for a living and attending some of the coolest sporting events imaginable.

Then I left journalism. Sold most of my stuff. Packed up the rest. Moved to New York City to pursue my dream of living in the Big City.

I knocked on doors and handed out my resume to anyone who’d take it.

After months, in the middle of the Great Recession, I finally landed a position at a public relations firm doing cool shit for brands like Guinness and MasterCard.

I even worked on the 34th floor of the Empire State Building.

Then I left my PR career to voice three audiobooks.

From there, I transitioned to my passion for fitness and built my fitness and nutrition coaching brand while being a stay at home dad to my two kids.

My point here is not that I’m necessarily cool; it’s that I’ve got a ton of stories and experiences that I can share with others.

I’ve got a different world view and perspective than many of the people I know.

I can talk about growing up as a biracial kid in a small Florida town (not awesome).

Or I can easily chat about the latest sports news or last night’s game from the perspective of a former sports journalist (kinda awesome).

Then I can dip into food, culture, travel, living in NYC, politics, changing jobs and careers, side hustles, corporate American lifestyle (it sucks) and pop culture.

My goal for you is not to have a laundry list of stuff like me; but to have some more interesting topics you can talk about going forward.

Interesting people live interesting lives

Being more interesting isn’t just about showing off at parties. But, I mean, it’s pretty cool to show off at parties, though.

In simple terms, if you are more interesting as a person, it stands to reason that you’d be living a more interesting life in general.

Which means you’d be breaking free from that boring ass cycle of mediocrity that I outlined at the start of this newsletter.

Instead, you’d be exploring new and interesting things.

You’ll start to light up the brain in new ways and encourage new thoughts, new ideas, new stories.

This might be the catalyst to your own reinvention. To do more. See more. To build or to create more.

The simple steps to become more interesting

By simply trying to become more interesting, you’ll end up being interested in more things.

You start to live life more proactively.

If life is like a video game, then these the side quests to level up and be more interesting:

Acquire more knowledge

Get out of your comfort zone and start learning something new every single day.

Read more books.

Go pull up YouTube and find a few things to expand your mind (just be careful not to get red-pilled by some bro who worships Jordan Peterson).

When you start to learn new and interesting things regularly, it will translate into you becoming more interesting, too.

Do more interesting things

It’s easy to start settling when you get older, especially as the kids start popping into the scene.

But, you’ve accepted that this is what you’re doing for life and you’re mostly fine and comfortable and you’re okay with that.

You get one or two vacations per year, and maybe take your kids to Disney.

But to get a bit of that European feel, instead of booking the trip to Paris (like you always dreamed about), you just opt to go to Epcot and check out the French area there.

I’m sure the croissants are fantastic.

But … that ain’t it.

If you have the means and ability, you need to start doing more interesting things if you want to be more interesting.

You are not too old for this.

It doesn’t have to be some kind of American Ninja Warrior epiphany that you’re going to learn to scale mountains.

But this is your life’s work to figure it out.

Go do something fun and interesting.

Develop a skill

I feel like most articles like this are then followed by some dudes telling you to buy his marketing and writing course to start your own business. Ugh.

If that’s your thing and you want to start your own business in the creator economy, cool. And bonus points if you want to really develop a better skill around writing (content, newsletters, captions, videos, screenplays, books, etc.).

But, you don’t have to start your own business to feel more fulfilled.

Skill acquisition can just be something that entertains and provides some fulfillment in your life.

Okay. Got that off my chest.

Maybe you can learn a new language (I’ve been procrastinating on my goal to speak fluent Italian myself).

Learn to do a handstand if you’re physically capable.

My wife has been really getting into learning about all things Human Design.

Chess. Violin. Painting. Cooking. Find something new that lights you up and explore that for a few months.

Develop a passion for learning new and interesting things and you’ll be more interesting by default.

Become a storyteller

This one relates closely to the knowledge acquisition bullet. Because as you learn more things, you’ll have more stories to tell.

Pro tip: Most storytellers have a go-to list of greatest hits they can turn to depending on the event and audience.

Start here with an introduction to telling better stories.

If you start reading more, you’ll expand your mind a bit and have a lot more things to share.

Read more fiction, too.

The best storytellers are fiction writers for a reason. You’ll learn how to tell betters as a result of absorbing more stories.

Ask better questions

One thing that I truly value from my time as a journalist is my ability to ask questions.

To be truly curious and investigate things, situations and even people.

In order to get here, you’ve got to be actually interested in the other person.

Listen to what they are saying.

The best interviewers come prepared with topics, themes and questions they’d like to address.

But they also don’t get caught up in a prepared script, they are able to listen to the person they are interviewing and have a back and forth conversation.

They are able to ask a question, get a response and then ask more questions to go deeper on those responses.

A few layers deeper is where the real interesting stuff comes out.

So you have to shut up.

I know you followed the first three bullets and now you’ve got knowledge to share, a super interesting skill and you’ve mastered the art of storytelling.

But, read the damn room, too.

There’s a time for taking over the conversation. And there’s an equally important time to just shut your face hole and listen.

Doing so will help you find more interesting questions to ask.

And that might lead to a better prompt and invitation to show off just how interesting you have now become.

Use this article to help jog the brain and start asking better questions.

Consume interesting things

You spend far too much time consuming the thoughts and opinions of other people.

As soon as you pop out of bed, you don’t even get the morning boogers out of your eyes before you reach for your phone and start scrolling.

None of this stuff is terribly interesting.

(Except for my content, of course … We all know that consuming this newsletter is a great use of your time, so thanks and keep at it. But, then you’re done reading this … put the damn phone away.)

Start consuming with intention.

Pick up better books.

It’s okay to have a guilty pleasure show (my wife and I binge watch Love is Blind sometimes, sorry not sorry if you judge me now). But we still very much watch real, interesting and worthwhile shows and films with the vast majority of our viewing time.

Stop mindlessly reading thousands of words on Threads, on Facebook or in the captions on Instagram.

Instead, pick up better books, find better and more interesting newsletters (like this one) and shift from reading crap for cheap distractions.

Instead, become the interesting person that reads and consumes interesting things with intention.

Doing all of this will encourage and empower your brain to start sharing more relevant stories.

And that’s what’s going to make you more interesting in your 40s and beyond.

Hang out with other interesting people

There’s this cliche that if you are the smartest person in the room, you are in the wrong room.

Meaning, to really expand your brain you should challenge yourself to be with people smarter than you.

The same applies to being more interesting in your 40s.

Seek out other interesting people who don’t look or talk like you.

People who are from other walks of life and have different lived experiences.

I’m not saying you need to ditch your friends. Especially since adults are suffering from loneliness as we get older.

But, I am saying that it’s time to find more than just your high school pals for drinking buddies.

• Use local meetup clubs if you can.
• Go talk to more people at pick-up and drop-off for school.
• Chat with your barista a little more.
• Reach out to people every single day and strike up a conversation.

If you’re in a really homogeneous environment, maybe it’s time to branch out and explore more things.

You’d be surprised how many people are untraveled.

Do more than just go to Disney World for a break. Instead of trying to grab French culture from the EPCOT France, save the cash and go to the real France instead.

If you have to do so, look online for communities that you could join to expand your network and meet more interesting people.

You are interesting than you think you are

As this continues you’ll start to pattern your brain into more opportunities to seek out new, interesting, exciting and cool things.

You’ll learn more.

You’ll live more.

You’ll start sharing more.

And people will start thinking that you’re the coolest person in the room.

I hope you found this useful. If so, I’d appreciate it if you sent this newsletter to one person you think would benefit from my writing today.

And as always, if you have any questions, please feel free to reach out.

I answer all of my emails at pete [at] petecataldo [.] com … Hit me up with the subject line “how to be more interesting” and I’ll answer any questions you have to make this work for you.

Until next time,
Pete