I’ve always been a private person. I’ve never been afraid to share my intimate details but I wanted it to be with people I trust. It also had to be in the right moments.
In my previous article, I reflected on the hard choices I’ve made in my 30 years.
And one of the hardest choices for me has been giving up my anonymity with this blog. I’ve had to accept that whatever I put out to the world will now be there forever.
But I know in my heart that the more I open up to you, the more connected you feel to me. People draw all sorts of inspiration and lessons from personal anecdotes and stories.
When I published the first part of this article, I was touched by everyone that commented and reached out to me. I had more emails with people sharing themselves than maybe ever before. It was incredible and allowed me to become closer to you, too.
That further inspired me to dig deep and share more of my world with all of you. I hope these stories continue to help you when faced with hard choices in your own life.
Table Of Contents
Just Say No
Once I started working on myself and being more social, I received more attention from women. Attractive coworkers, friends, and acquaintances showed increased interest in me. I was still learning how to navigate these new waters.
One night I was having cocktails with a female friend. We talked about traveling and vented about our jobs.
She ended up getting a little too drunk and tried to kiss me when I dropped her off at her place. I backed away before she could and said, “I don’t think this is a good idea.” She stood shocked for a moment, said a brief goodbye, and then went inside.
Another time I was at a company dinner sitting next to a female coworker. She gave all her attention to me throughout the night – leaning in close to talk and touching my shoulder.
When everyone was getting ready to leave, she asked if I could give her a ride home. She stayed close to me in the car and then invited me to hang out when we got to her apartment. I told her, “I think I shouldn’t, I have to get up early tomorrow.”
Something must have clicked because she suddenly realized that I hadn’t been reciprocating her affection and gracefully left.
In both scenarios, I knew these girls weren’t right for me even though I found them attractive. Each of them was looking for their next boyfriend and I wasn’t interested in a relationship. So I knew casual sex would just likely leave someone hurt.
We were also too different. The first woman was a party girl with substance control issues and deep insecurities. The second was a brilliant woman but she was very vanilla, didn’t have much of a sense of humor, and wasn’t adventurous.
I most importantly valued their friendships. And I knew if I hooked up with them without wanting more, it would be difficult to maintain that friendship (and work relationship).
So I let both girls down gently. It hurt their feelings in the moment but I believe I’ve been able to stay friends with them because of it.
How it changed me: For a long time, I chased every attractive woman who showed me attention. I was desperate, needy, and went into every interaction with a mindset that I needed to win a girl over and get her approval.
I tried every trick in the book to break that mindset and not put beautiful women on a pedestal. I approached like a madman and slept with random girls.
Only when I became willing to lose the wrong girls to find the right ones did I develop real self-esteem. I could finally see past the beauty and see the real people in front of me. I was no longer desperate for approval and could cherish female friendships.
And because of all this, I stopped being terrified of talking to pretty girls.
A Friendly Start
My wife and I were having dinner in Siena, Italy at a small local restaurant. A couple in their early 50’s sat at the table next to us. At the end of their meal, the server offered free glasses of Amaretto or Grappa. They chose the Grappa and the man took a swig.
He recoiled from its overpowering fermented flavor. I turned to him and said, “Guess it looks like we’re getting the Amaretto.” We laughed and all began chatting about where they were from, what they were doing there, and their overall impressions of Italy.
As we paid for our bill, we said our goodbyes and left. I turned to my wife and said, “I really liked them.” She said she liked them a lot, too. I decided to go back in the restaurant and invite them to get together again.
When I approached them and asked if they’d like to have dinner at our next stop in Florence, they both exclaimed, “Yes!” We traded info and went on our way. We met up again, shared pictures while traveling, and have now made plans to spend time together at their estate in Mexico.
I’ve had numerous friendships with people from all over the world begin under similar circumstances – all it takes is some small talk and taking the leap on making future plans.
How it changed me: Experiences like this remind me that everyone is yearning for connection. The problem is that everyone is waiting for someone else to initiate it.
A lot of you tell me you can’t make or maintain friends. You go to parties, fitness clubs, dancing classes, and other social events and yet never make future plans with anyone. You tell me you don’t talk to or hang out with your existing friends that often.
Most of the time, your problems will be solved when YOU initiate. That means talking to more people and extending offers to meet up again and go do something together. It also means checking in on friends with kind words, genuine curiosity, an interesting article, or a silly snap.
I know you’re upset because you wish more people would do that for you. But swallow your pride and take the lead, your vulnerability will give others the strength to start reaching out first.
A Different Path
My father gave me the devastating news: we were going to have to give up the family restaurant.
He’d had a second heart attack and a quadruple bypass. The doctors told him he wouldn’t be able to work during the recovery process. With the business already struggling, he was officially forced to give it up.
Our income stream vanished. He could no longer pay my college tuition.
I had a decision to make. I could work and put myself through school, but not be able to support my parents. Or I could give up school entirely and get a full-time job that would ensure their financial stability.
I looked at my father and said, “I’m quitting school and getting a job.”
He immediately rejected the idea. I tried to argue my point and he became furious. He shot down everything I threw at him.
Finally, I raised my voice and sternly said, “Dad, you know there’s no other way. This is our only option and I’m taking it.”
He started crying. He wasn’t angry with me for having the idea. He was angry that he knew it was the truth. He was ashamed that his young son had to give up his dreams and he felt responsible. Both he and my mother had made some big mistakes that led to this.
The following years were tough. We lived month-to-month, had to borrow money, and were always aware of the dark cloud of homelessness looming over us.
It killed my self-confidence. I felt like a loser. My dream had always been to get a degree, especially because my parents never had, and make something of myself. I had placed my entire identity on becoming that educated man and now all hope was gone.
I resented my parents (they were still heavy smokers at this time and damn that cost a lot). Whenever they asked me about myself or my work, I got defensive and lashed out.
I felt everything I’d planned for my life had spun out of control. So I started trying to control the only thing I had left at the time — a relationship with a great girl. Eventually, she left me, too.
In the moment, giving up the life I wanted was the worst decision ever.
How it shaped me: Sometimes choices take years to show their consequences.
First, I learned that things never really go as planned. Shit happens that you have no control over that will forever change your path.
But this experience also helped me accept that different does not have to be seen as better or worse, just different.
I had the “perfect” path all laid out. And giving it up made me discover an entrepreneurial career I’m infinitely more passionate about. It also forced me to relentlessly work on myself, become self-reliant, and grow much more than I would have otherwise.
If you’re rigid and holding onto perfection, you will always be disappointed. You’ll always be trying to manage every situation beforehand instead of developing your ability to adapt to whatever’s thrown at you.
Your need for control will end up controlling you.
Finally, I was reminded that family comes first (whether that’s blood-related or friends). You have to care for the people you love.
At the time, I questioned the choices I made because I was terrified and angry. I have no regrets now and I wouldn’t have changed a thing.
The choice to stand by my family has made me a better man and brought us closer together.
When I had to drop out of college to support my family, I technically had nothing to offer. I had no degree and no real-world job experience.
It would’ve been easy to take a minimum wage job or two. And I would have if that’s what it came down to.
But I knew that if I really wanted to support my family and myself, I needed more. Despite everything in my body telling me I wasn’t good enough, I had to try.
I saw the housing market was booming. With a bit of research, I realized that I could teach myself the loan side of the business. All I had to do was learn how to sell.
So I sent out applications and personally called a bunch of mortgage companies. I was honest with them. I told them my situation and that I knew I was young. But I promised that I would bust my ass at all costs, I would keep an open mind, and I was eager to learn.
Eventually, someone took a chance on me and launched my two-year stint as a loan officer. Early on, I stood out from the pack and did well for myself. It wasn’t that I was necessarily better than the other employees; in fact, many people were much better at selling than I was.
But I worked harder and hustled more than almost anyone else in there. I made a statement for myself out of sheer willpower. I got better and better at selling, too.
When I left the industry due to ethical concerns and feeling the impending doom, I applied my same determination to government technology. I saw an opening at a company and approached the CEO with the same persistent mindset.
I told him I was willing to do whatever it took and be a sponge. He knew I was sincere and took me under his wing. I worked there for over five years and made myself a linchpin within the company.
Finally, I started getting involved in the pickup artist community. While at my government job, I felt more and more passionate that I wanted to teach these skills to men as a career. Again, I had no credentials but I reached out to professional companies.
I got recruited to two of them and spent years learning the craft. I eventually left to start my own business, but the mentorships and guidance I received were invaluable.
How it changed me: I started to see the transformative power of healthy passion and ambition. I saw how there was no harm in shooting for the stars and letting people meet you halfway. This can apply to every avenue in life.
I’ve also helped friends apply that to their career situations. They’ve asked for higher starting salaries and gotten them (much to their surprise). They’ve written a letter to the company they freelanced for and gotten a full-time job despite more “qualified” candidates.
Even reaching out to powerful figures with free value, an intriguing question, or engaging dialogue can spark opportunities you’d never thought possible.
I learned that if you show people your heart, your willingness to fight for more, and desire to connect with them — that can trump everything else. You cultivate your own reality where you gain important relationships, referrals, and job offers.
I’m not saying it’s easy and it’s definitely gotten harder since the recession. But if you know how to connect with people on a meaningful level, it’ll take you to new heights.