The Powerful Lessons That Made Grown Men Cry at My Confidence Retreat
Jason asking the hard questions. Pictures courtesy of Ann-Marie VanTassell Photography.
In February I ran my second confidence retreat with my friend Jason Connell in Austin, Texas.
Jason brought the much needed spiritual and philosophical elements to the experience. His presence from professional speaking gripped everyone and kept us grounded in the moment. He always asked the perfect questions to uncover core issues necessary for profound growth.
Now where do I start with the wonderful city of Austin?
The weather was like summer in winter. Culture oozes everywhere you look — whether that’s with the stunning murals all over the city or the live music at nearly every venue.
On the famous Rainey Street, a developer bought a row of bungalows and turned them into nightlife venues. Almost every place has outdoor space in the back with tables, games like mini golf, and a band or DJ.
Walking into these spaces with a dozen people felt epic. At one point, we jumped up on the main stage with the DJ at a venue and led the whole crowd. We took our energy and took over the venue.
It was amazing to see men who had struggled with self-confidence become free. They let go of worry, got passionate, and tapped into their core strength the whole night. They became leaders.
On top of all that, Austin was the friendliest major US city I’ve been to.
Usually when you get an educated hipster culture it comes with an air of pretentiousness. Not here. Somehow they’ve managed to retain the southern hospitality Texas is known for.
Walking into any store and having people genuinely want to converse with you was so damn refreshing. I actually felt sad knowing I’d have to make my way back to the standoffish Bostonian world.
I feel blessed to have had another successful retreat where men walked away with a newfound sense of self. They also shared some emotional and vulnerable moments together.
Here are 7 powerful lessons that made everyone cry at the retreat, including me.
You really can meet people just about anywhere
Nobody believes you can meet people anywhere. I’ve been doing this for 10 years and everyone thinks it’s impossible or will turn out horribly.
The guys coming into the retreat thought it wouldn’t work for them. Jason was skeptical about certain locations since he doesn’t do many random day introductions.
Even our female photographer pulled me aside at the beginning of the retreat. She told me she thought it would be weird to talk to girls who might be reading a book on a bench or with headphones in. She said they wouldn’t want to be bothered.
By the end of the retreat, however, everyone’s eyes were opened.
The guys approached a group of girls at a restaurant. The girls invited them to sit and they all hung out for a while.
We talked to a handful of women at Whole Foods. One guy saw a girl looking at the prepared food and commented on it. She responded with enthusiasm, said she needed to get lunch, and literally grabbed his hand to pick out a meal together.
One guy told me how he thought the cashier was really pretty. I said he should invite her to do something while he checked out. Though he was still unsure, he took a chance and got her number (while she blushed and smiled the whole time.)
Another retreat member even met a girl while waiting to play Laser Tag and exchanged numbers.
While a number doesn’t necessarily mean anything, when these guys followed up, the girls responded positively — and that does mean something.
That doesn’t even include all the people we met during our nights out.
This is the story of my coaching life. I’ve watched thousands of people connect in the most ridiculous, unlikely situations. And at the end of the day, we all want to meet someone amazing and that often trumps all other circumstances.
This is something you need to experience for yourself to actually see the reality.
Those people will respond better than you ever expect
One of the main fears about approaching is that you’re going to get humiliatingly rejected. You imagine a woman is going to think you’re disgusting and brush you off.
At a bar or club, that’s occasionally the case. But during the day or at social events, it almost never happens.
In fact, every morning of the retreat I did a check-in with the guys. I asked them about their interactions and whether or not they’d had any negative experiences.
I kid you not — not one of the guys had a bad social experience the ENTIRE retreat in 50+ interactions.
I know this isn’t the norm and it helps that Austin is a super-friendly city. But usually the worst rejection you’ll get during the day is, “Thanks, but I have to get going” or “Sorry, I have a boyfriend.” That’s it.
In fact, the only person who had a terrible interaction was me!
We were out late one night and met a girl with her two friends. She was heavily intoxicated and was rude to me from the first few seconds. She flung obscenities at me, called me a loser, and told me to “shut the fuck up” about 15 times in a row.
She then accused me of trying to get with all of them. When I calmly explained that I was happily married, she laughed in my face and said I was lying about my intentions.
I gave it one last hurrah and continued to kill her with kindness. She gave no fucks and wouldn’t relent so I walked away.
These are the worst-case scenarios guys worry about. And I’ve rarely witnessed them in all my years going out.
The point is, if something like this ever happens, you can’t stress about being rejected in such a rude way. Because personally, I wouldn’t keep trying to connect with someone who treated a stranger like that.
Build a fulfilling social lifestyle that meets women, not the other way around
Whenever guys begin their self-improvement social journey, they focus on relentless cold approaches. They go out constantly by themselves with the sole purpose of meeting women.
As a result, they do talk to a lot of women.
But they don’t always have great results. Nor are they working towards cultivating a healthy mindset.
And here’s why: when you’re going out alone just to approach, you tend to carry high levels of stress and anxiety. You’re not actually enjoying yourself and having fun. You’re not hanging with friends or indulging in a favorite hobby.
Your interactions then suffer because you’re not presenting your most charismatic self.
Additionally, you’re basing your “success” on whether or not your approaches go well. You’re seeking approval and letting your worth be judged by random women.
This makes it extremely difficult to stay motivated and build real self-esteem. Instead, it’s much more rewarding to prioritize building a great social lifestyle for yourself.
That means trying out new hobbies and attending events. Going to live music venues. Dancing, hiking, or playing sports. Making friends through those avenues. And that also means going out to these places with your existing or new friends.
Then, coincidentally, there will be an abundance of women in these environments who you can talk to!
And now, you’ll actually be in a great mood with great energy. You’ll be supported by friends (which makes thing so much easier.) Women are naturally drawn to social guys with cool people around them.
Think about the girl you’d like to meet: an awesome, independent woman. Would she want the guy who obsesses over only meeting women and doesn’t have much else going for him? Or would she want the guy who’s got his own happy life, hobbies, and friends?
At the retreat, we played laser tag and a girl started a conversation with us. We played Frisbee in the park and had people chatting us up.
We went to a spray paint park and had a girl offer us some cans to paint with her. We met a professional dancer shooting a video. Two girls doing a cross-country tour come over to hang out with us.
And every night out people welcomed us into their social groups after seeing us have a great time.
Focus on approaching girls and that’s all you’ll accomplish. Focus on the bigger picture and you’ll be a well-rounded man women can’t get enough of.
Male bonding is just as important as anything else
When Jason and I started interviewing potential retreat members, we asked them about their male friendships.
All the men said they had some guy friends and making more wasn’t an important focus for them. They couldn’t have been more wrong.
By the end of the retreat, the guys couldn’t stop talking to each other. Multiple guys came up to me before it ended and told me how the friendships alone were worth the entire experience.
And now after the retreat, they’re constantly posting in our Facebook group. They share experiences, challenge each other, and hold each other accountable.
The same thing happened at my previous retreat in Mallorca. Everyone came in looking to gain confidence and meet women, and ended up with friendships they cherished. They’ve even made plans to hang out again.
I don’t think a lot of men realize how incredibly important it is to have other male friends — especially close ones.
Intimate experiences build friendships with almost anyone
When guys tell me they have friends, they usually mean acquaintances or casual friends. Let me explain…
They hang out with those guys. They go out and socialize. They play video games together. They shoot the shit about work, women, travel, and more.
But they don’t always reveal their deepest thoughts. They don’t talk about their personal struggles. They don’t open up about their fears and insecurities.
And it stops them from developing a stronger bond because vulnerability is the birthplace of real human connection. And it can bring together people you’d never expect.
That’s what I try to explain to skeptical men who believe they have enough good friends. Or when they think that meeting new guys at events isn’t worth the effort.
The guys at the retreat were of different ages, ethnicities, and social statuses. If they met out in the world and only kept conversations surface level, they may have only been casual acquaintances.
But because they had an opportunity to get vulnerable with each other completely judgment-free, they transcended their differences.
You can replicate this with many people. You don’t always have to get deep the first time you meet (and often it’s not advised), but through further interactions where you do, you’ll connect with people you never considered.
I’m not saying everyone will be or needs to be your best friend. But you should give people the opportunity to see the real you and for you to see them. Take that first leap and incredible things happen.
If you haven’t cried in a while, you probably need to
I don’t cry often. Yet at the retreat, I cried my eyes out and so did everyone else. It was awesome.
Men are told that we’re not supposed to cry. We think it’s a sign of weakness. And we wouldn’t dare be caught crying in front of another guy for fear of being mocked.
So in turn, we walk around protecting our hearts. We don’t open up to people. But what I learned at the retreat is that we often don’t open up to ourselves, either.
We refuse to think about our pain. We shove it away or just call ourselves stupid. We never talk about it with anyone or and never show ourselves enough love or compassion.
And the moment we do…we cry. A lot.
The first day of the retreat, nobody cried. But by days two and three, where we started pushing each other to our emotional depths — the first person cracked.
Hearing his true pain and flood of emotions immediately affected everyone else. One by one we all fell like dominos and started crying, too.
This went on for two hours and was a highlight of the retreat for me. I know that experience made me feel alive. I felt human and normal. I felt connected to people. I felt connected to my soul. I felt liberated and stronger from that moment.
And I know it had the same impact on everyone else. Two different guys told me they hadn’t cried in many years. One of them was in his 30s and said the last time he cried was at 13 years old when his dog died.
I couldn’t believe it! That story alone was enough to make me well up again.
Sometimes digging into yourself to get a good cry is exactly what you need to grow.
Men and women fear what they don’t understand about each other
More than ever, I see men and women at odds with one another. Everywhere on social media and blogs someone’s shouting about how men are all pigs and women are all heartless.
It almost always comes down to misunderstandings. Those misunderstandings lead to fear and animosity.
It breaks my heart to see that shit. Because I know that the second you get men and women together in a vulnerable, open space — those differences dissolve instantly.
I saw it again at the retreat…
Many of the men were holding onto anger and resentment towards women. They had dealt with rejections, flaking, and overall hesitance. They felt like many women had no compassion.
That changed when I shared how women are often bombarded by men — sometimes in very lewd and threatening ways. I explained how much scarier it is for women to put themselves out there.
Even our female photographer revealed how her friends had dealt with really intense experiences.
All those things combined shape how women are cautious about meeting up or moving forward with a new man.
The guys never realized how critical safety is to a woman because they hadn’t ever thought about that for themselves. Being more informed made them much more sympathetic and understanding to why some women act the way they do in dating.
The guys also talked about how terrified they were of putting themselves out there because they didn’t want to be seen as predators. They didn’t want women to feel creeped out, like they were objects, or uncomfortable in any way. This shame about their sexuality took control of their lives for years. They were racked with anxiety and fear with women.
This, in turn, made a great impression on our female photographer. She couldn’t believe what she’d heard.
She never thought men could have so much sexual shame about showing interest. She didn’t even realize that would be a problem and thought men would always be thinking about how to get in a girl’s pants. She was amazed that the men were so thoughtful of women’s comfort.
Most of all, she realized that men dealt with shame just like women, albeit in different ways. While they were worrying about being predators, women were often worrying about being too promiscuous.
Honest communication dispels misconceptions and cultivates empathy. It makes us realize that we’re not enemies and we’re not all that different.
Another retreat…another unforgettable experience. I’m ready for more.
Stay tuned — I’m announcing my exotic summer retreat in the next few days.
Special thanks to Jason Connell for his incredible scope of knowledge, dedication to the work, and for embracing my boundless energy. The retreat wouldn’t have been the same without you man.
I also want to thank Ann-Marie VanTassell for the wonderful photos. We’re so fortunate to have beautifully documented memories and pictures that made us all look damn good.
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