How to stop being boring: the f*ck it philosophy

Let’s say you’re boring.

Maybe no one’s ever told you that but you sometimes get a sinking feeling in your stomach that hints at it. Or maybe someone has told you you’re boring and it makes you feel like a worthless piece of ####.

You want to be interesting and fun, but you’re trapped in the prison of your limited social skills.

… But what makes you so boring?

You do.

The prison bars are made of your own negative beliefs and you can’t seem to squeeze through them. If there’s one thing you’re good at it’s tricking yourself into believing that you suck. How fun. Though the fact that you did this to yourself is actually good news. You can turn it around.


Once upon a time, when you were about 3-feet tall, you were all about fun. You were an explorer learning to navigate your world and nothing was off-limits.

You burnt your hand on the stove. It didn’t stop you from playing with fire.

Then along came social rules and the idea that you were “supposed to” behave in certain ways in certain situations. You learned that there were consequences to your actions and doubt replaced abandon. The world became more complicated than it had previously seemed.

Take Little Pete for instance. At 3-feet Little Pete liked to run around the house naked playing cowboys and Indians, screaming his lungs out. He didn’t give a shit.

At 4-feet Little Pete had his first crush. We’ll call her Lacey. Their class was putting on a dance for the school and the teacher asked the boys to choose their partners.

The problem was that Lacey already had a boyfriend, or at least a boy she held hands with at lunchtime (the little turdburger!). But when Miss Hudson told the girls that they had to say yes to the first boy who asked to be their dance partner Little Pete saw his opportunity. None of the other boys moved. Little Pete pounced! Lacey said ‘no’ but Miss Hudson sealed the deal.

They danced together for the weeks that followed and, slowly but surely, he won Lacey over. She told him she liked him.

Little Pete didn’t know what to do in this foreign scenario so every day he sent his best friend to ask Lacey if she still liked him. That was the extent of his contact with Lacey. She said yes for 3 days then changed her mind.

Little Pete was devastated. He developed a fear of talking to girls which dragged on until he was 18.


After a few more run-ins with “the consequences of his actions” he stopped taking chances. He made his decisions based on what people would think of him. He agreed with opinions, he avoided stepping on toes, he suppressed his desires. He was good little boring boy.

There was a time when you too used to act first, think later. Not anymore. Now you worry about all of the negative & far-fetched possible outcomes that your mind can conjure up, and they’re usually enough to convince you to be boring.

It goes something like this in an uncertain situation:



“I’m not sure what to do.”

1.     Do I have to do something (or say something)?

·         No: Do nothing. Play it safe.

·         Yes: Go to step 2.

2.     What should I do?

·         Option 1 — What is the polite thing to do?

·         Option 2 — What do I think is normal in this situation?

·         Option 3 — What is the easiest (least scary) thing for me to do?

3.     Choose an option and act.

You’ve run this process over and over again. You said ‘no’ to your inner explorer. Congratulations, you made yourself boring.

But the good news is it’s not you that’s boring. It’s the boring shit you choose to do that’s boring. And all it takes to stop being boring is to do something different.


There’s a problem with the Boring Boris process: we designed it to keep us safe and we feel safest when we use it, but we feel like crap afterwards.

Most people don’t dislike us when we use Boring Boris because we put none of our self in our actions, hence there’s nothing to dislike. They don’t see us at all. We make ourselves easy to ignore.

·         If I do the polite thing I make no connection;

·         If I do what I think is normal I’m not even copying a real person. I’m copying a hypothetical average and turning myself into a characterless bore;

·         If I do the easiest (least scary) thing I’m hiding as much of my self as possible. Only sharing what I have to. It’s like taking out a hair clip when you lose at strip poker. Boring.

If you want people to actually like you you have to get naked, or at least show some skin — figuratively ;). Give them something to like. Put your self in your actions.

Yes, there’s a risk in not being boring. Some people might not like what they see when you stop hiding, but their disapproval means nothing when you find the people who do like you. Those are the connections that will fuel you. Being truly accepted for the weird monkey that you are inside is the greatest feeling in the world.

It’s a much bigger risk to be boring. You’ll never make strong connections.

Imagine yourself in this situation: it’s your first day at university. You’re sitting in the lecture hall and you don’t know anyone. Imagine the speaker asks for a volunteer to stand up and tell the class something that you did in the past week as an ice-breaker.

Did you get a physical reaction to that last sentence? Lump in your throat, maybe? Are you unsure what to say?

Most people in the class will go through a thought process that looks something like Boring Boris.


“I’m not sure what to do.”

·         Do I have to do something (or say something)?

·         No: Do nothing. Play it safe. Hide.

Or if they’re singled out they take the easy option. They share nothing risky about themselves: “I don’t know… I did lots of things this week. Umm, I bought some textbooks.”

Not Felicity though.

Felicity used to play it safe but now she’s the first to put her hand up. She’s a risk-taker. She doesn’t mind looking foolish because she’s learnt there’s more to gain than there is to lose.

You might like Felicity or you might hate her, but would you say she’s boring? Read on and compare.


How do we put our self in our actions to become more fun? More interesting?

We replace the ‘should’ in Boring Boris with ‘want’. We stop reacting and start creating. It looks like this:


“I’m not sure what to do.”

1.     What do I want to do?

·         Option 1 — What experience do I want to create for myself?

·         Option 2 — What gets me excited?

·         Option 3 — What am I afraid of doing, that at least part of me wants to do?

2.     Choose an option and act.

Felicity’s heart is racing from what she’s about to say. She’s scared but she wants to connect, so she seizes this opportunity to share with the class. Because fuck it.

“I levelled up my Mage in World of Warcraft and my guild is raiding a dungeon tonight! If anyone here plays WoW come say hi.”

Now everyone in the class knows something about “Fuck it” Felicity. They have something they can talk to her about. They might even feel a bit closer to her. She certainly didn’t bore them.

Meanwhile no one knows anything about Boring Boris.

(Note: If you want to learn how to connect with people on a deeper level, there’s a free 10-minute PDF guide at the end of this article.)


Becoming interesting can be scary at first. But you want it. Do you know the combination of fear and desire that I’m talking about? That’s your green light. That’s your brightly-lit path away from boring.

Felicity didn’t stop being boring because she was particularly interesting. She stopped being boring because she decided to “get naked”. Now she expresses her opinion, she steps on toes, she chases what she wants… and the funny thing is people love her for it. She’s real.

The next time you’re unsure what to do in a given situation, try running “Fuck it” Felicity instead of Boring Boris. Start small, make mistakes and learn from them.


A few readers have asked questions about connecting with people better. I thought I’d use their questions as examples.

A real estate agent told me he wants to build trust with his clients. “I’m not an average agent. I care about them and getting their home. I want them to know I’m the best agent and they can trust me with one of the biggest investments of their lives.” He tries to connect with his clients but the majority of the time they give him one-word answers. The stress of trying to sell them a house gets in the way of connecting.

Boring Boris would act the way he thinks a real estate agent “should” act in this situation. He’d make polite small talk and tell the clients how spacious the bedroom is and how much light the living room gets because the windows face east, where the sun rises.

“Fuck it” Felicity might say “Listen, before I show you some houses I want you to know that I actually care about you finding a home that makes you happy. Some agents just want to offload as many houses as possible but I can’t do that… I’d feel too guilty if I forced something on you. Plus I’m a terrible liar. So I actually want to know what you like and what you don’t like. If you promise to tell me, I’ll promise to not pretend a crappy house is great for you.”

Another reader is having trouble connecting with people because he’s too eager to connect. He says he has a weird personality and sense of humour so he resorts to polite conversation to play it safe… meaning he’s essentially running the Boring Boris process. His conversations look like this:

Him: Hey! How are you?
Them: Good, how about yourself?
Him: Pretty good.
Him (in his head): (Okay what’s next? — awkward silence)
Him: Gloomy weather, eh? or What’d you have for lunch?

“Fuck it” Felicity would make it personal. She might read the other person’s body language and say “Hey, you look (happy/focused/full of energy/excited/chilled/etc!). What’s happening?”


Even if you read them wrong they’ll appreciate that you’ve taken the time to notice them. And now you can talk about what’s really going on, instead of the weather. Try to avoid making negative observations like sad, tired, sick, etc. because it can make them self-conscious. You could put a more positive spin on it with something like “You look like you’ve been working hard.” or “You look like you’re deep in thought.”

If they seem like they don’t want to talk, because sometimes we all don’t, you can follow it with “Anyway, you look like you’re on your way somewhere.” or “You look like you’re really busy.” They’ll appreciate you giving them an easy out and will remember how socially aware you are next time.

A third reader rarely shares things about himself because he feels like he’s too boring or not good enough for his friends. He talks to his friends about football, wrestling and topics he thinks they want to talk about, because they’re easy. He judges himself based on how interested they are in what he says, yet he puts no self in what he says. Textbook Boring Boris.

If you’re scared to share something because you think “it’s too boring”, you’re probably wrong. Most things that are scary to share are actually rather interesting. People have similar fears. They can relate.

When you share things that scare you people recognise that you’ve trusted them enough to share something scary. They admire that you’ve taken a risk for the benefit of connecting with them. You stop being boring, you become real.

That’s why when “Fuck it” Felicity feels like she’s too boring she might say to her friends “Hey guys, how do you always come up with interesting things to say? Sometimes I think I’m a bit boring.” Because she’s real. Be real.

Boring Boris’ fears come from low self-esteem or insecurity. We all have them to some degree. Applying “Fuck it” Felicity’s approach can help you change not just your outcomes, but also the root of the problem over time.

Now go get back in touch with your inner 3-foot-tall explorer. Go play with fire.

If you want to learn how to connect with people deeply through conversation check out Make Real Friends: 3 Conversation Hacks You Never Knew. It’s a free 10-minute guide that tells you what to say, how to say it and why to say it.

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