30 Years of Hard Choices That Shaped Me (Part 1)

Decisions decisions

Life is a series of choices.

And I believe our quality of life is determined largely by those choices.

Of course there are other factors such as luck, genetic predisposition, upbringing, and overall mental health. But to a certain degree, your happiness and growth are greatly influenced by your actions.

When you encounter hardship, how do you handle it? When you’re doubting yourself, do you let it hold you back from trying? When you’re scared of judgement or uncertainty, do you act in self-love and compassion or simply stifle your needs?

I turned 30 two weeks ago. I’ve been pondering the decisions I’ve made that have changed me for the better. As a whole, they were tough choices that I knew would ultimately benefit me in the long run. They were based on having self-respect, staying true to myself, being vulnerable, and being bold.

It hasn’t been easy. In fact, some of the decisions were terrifying and didn’t always have the immediate gratification I’d hoped for. But in the end, they provided me with invaluable lessons, self-confidence, and a healthier connection with myself and other people.

In the first of two parts, I hope sharing some of my most life-changing decisions can inspire you to make better choices, too.

Quitting Done Right

When I first started this website, I enjoyed a cushy government job while I coached on nights and weekends. I was basically an entrepreneur who also had the safety net of a reliable salary and benefits – a situation most people would kill for.

However, new management soon took over my day job and grossly mistreated employees. Many co-workers I’d grown close to had their morale and feelings crushed.

And deep down, I knew coaching was my long-term passion.

So despite my fear of financial uncertainty, I decided to quit. I also decided that I needed to let management know the extent and repercussions of their abuse of the people I cared about. I wrote an uncompromising email detailing this and was then called in to face my three bosses alone in a closed room.

You can read the full story here.

How it shaped me: This experience reinforced that standing up for my values and my friends is more important than being comfortably ignorant of their mistreatment. I was reminded that humanity is more important than financial gain. It also showed me that I could endure even the most intense and stressful social moments.

Midnight Epiphanies

My epiphany

Back when I was a dating newbie, I went out with this really cute girl for a couple months. After a while, I started to notice she had some deep emotional issues and tended to take them out on me.

On multiple occasions, she’d sleep over at my place and struggle with her insomnia. She’d wake me up even though she knew I had stressful work days starting early in the morning. She’d then get upset when I wouldn’t stay awake with her.

Since I was young and inexperienced, it was hard to give up an intimate connection with an attractive woman…especially when there was no guarantee that I’d find someone else. But after an internal battle, I decided it wasn’t worth it. I drove her home in the middle of the night.

How it shaped me: This was one of the first moments when I prioritized my own worth and happiness over keeping a girl. It taught me that it’s better to be single and happy than in a toxic relationship. Just because you CAN date someone doesn’t mean you SHOULD.

This has helped me make more clear decisions on the romantic connections I’ve pursued. I haven’t wasted much time with the wrong women or dealt with a lot of drama because of it.

Far Out, Man

I grew up believing drugs were pure evil. Programs like D.A.R.E. taught me that people who did drugs were morally bankrupt criminals and using them even once would completely destroy my life.

Until I was about 19 years old, I was vehemently anti-drug (even though I’d drank alcohol a few times and thought that was okay. Go figure – media manipulation and social acceptance are powerful tools.)

Then one day I ended up at a party after an ex broke up with me. She’d smoked weed without telling me early in the relationship and it had led to a big fight. So when a good friend offered me a hit of a joint, I was in the perfect state of mind to say, “Whatever, let’s see what this is all about.”

To my surprise, I didn’t start selling my body for more weed. I didn’t turn into a degenerate. I got high and I had a fun night with my friends.

Eventually, this led me to try psychedelic drugs such as psilocybin (mushrooms) in a controlled environment.It launched my research into writers like Aldous Huxley, Timothy Leary, and Terrance McKenna.

As I’ve written before, these experiences had a permanent, profound impact on my way of thinking and personal development.

How it shaped me: Using these substances pulled the veil back from my eyes more than anything else. It helped me see that there’s a lot of misinformation (both intentional and unintentional) and hysteria out there. I started challenging new ways of thinking, doing more research on almost every subject, and being more skeptical yet open-minded.

They also helped me drop my ego at times and become more self-reflective. They encouraged me to let go of my insecurities to embrace personal growth. Those experiences helped me become less of an asshole in my relationships, recognize connections that weren’t good for me, let go of pain, and appreciate life more.

We’re seeing more and more research on how psychedelics can make people more happy, help overcome addiction, and facilitate brain activity in new ways.

This isn’t a PSA for drugs. I don’t care if you try them, nor do I think everyone should. It’s about accepting that they’re like anything else — tools with real pros, cons, and consequences. Some are more dangerous or risky than others and in general, they should be used in moderation.

Bro-ing Out

Fist Bumping Bros

I discovered the local pickup community at the beginning of my self-improvement journey. I joined the Boston online forum and noticed a guy introducing himself who shared a lot of similarities with me. We were both drummers, loved tech, and played Counter-Strike.

I decided to message him and ask if he wanted to meet up for a drink. It felt super strange to invite a random internet guy out for a beer — especially 10 years ago when that wasn’t common. But with most of my friends moving out of state, I had no one to go out socializing with.

We ended up getting drinks a couple nights later. From there, we went out to meet women together regularly and became best friends. We pushed each other relentlessly and grew quickly because of it.

The night I saw my future wife across the room, he was the one who encouraged me to go say hi. When he wasn’t sure how to introduce himself to the woman who became his future wife, he remembered the skills I’d taught him. I ended up being the best man at his wedding.

How it shaped me: I learned that you can connect with someone in the most unlikely of ways. Some of my best friends in real life also started out from online communities or when they e-mailed me as a fan.

I saw how one decision can create a massive chain reaction that changes your life forever. Neither of us would have likely met our wives if I didn’t decide to send a PM on a message board.

Risking It For Love

As written above, I was out one night at a cocktail bar in downtown Boston with that drummer friend.

I saw a girl hanging out with her two friends. They seemed like they were having fun in their own world. She had an artistic style and a radiant smile.

I was little intimidated by the fact that there were multiple girls and they were standing off to the side, purposely secluded. It would have been easy for me to make an excuse not to talk to her like, “She probably doesn’t want to be bothered.” or “It’s probably better if I just keep this a guys’ night.”

But luckily, I’d built up enough positive social reference experiences and had brought a friend who motivated me. Having the courage to say hello that night led to the most important romantic connection of my life…my wife.

How it shaped me: This experience really showed me the power of a single moment. It further inspired me to teach others to take healthy social risks. Because at the worst, you might feel a bit of awkwardness. At the best, you might find love or a best friend.

This doesn’t mean you should obsess or idealize approaching one person. But you should understand that finding the right person requires a little effort and a lot of luck. You need to meet a compatible partner with mutual respect, attraction, and similar values (or at least open-mindedness).

Every time you miss out on an opportunity, you could be throwing away a meaningful connection and delaying finding an amazing relationship.

Burning Bridges

When you’re young, you don’t consider the quality of your friendships. You make friends with just about anyone, despite how they may treat you.

Sometimes those friends make fun of you. Sometimes they talk behind your back. Sometimes they try to hook up with your girl or sabotage your relationships out of jealousy. And sometimes, they’re not there for you when you need them.

Regardless, I still had a sense of loyalty to my friends. That’s just the way things were.

But through my self-development, I began respecting myself more. I took to heart the advice, “You are the product of the 5 people closest to you.” I stopped seeking approval and started seeking out nicer people.

Because whenever I thought, “Would I treat this person this way?” The answer always was an unequivocal no.

I expressed my concerns to give my friends a chance to change if they were unaware of their behaviors. If nothing changed, I cut those connections. Other so-called “friends” I recognized immediately weren’t good for me and walked away.

I left friends who joined pyramid schemes and to take advantage of others. I left friends who repeatedly tried to sleep with girls I was dating. I left a friend who tried to steal from me. I left a friend who was so manipulated by his girlfriend he cut off all contact with his family and friends.

I’ve never regretted those decisions since.

How it shaped me: This helped me realize that healthy friendships consists of more than  good laughs and fun times. They require mutual respect, compassion, and kindness.

It also helped me focus on finding real, meaningful friendships. There’s only so much time in the day – you’ve got to let go of people who drag you down in order to move on to bigger and better things.

Since surrounding myself with nice people, I’ve had less drama and more support. I’m excited to spend time with them because I know they’re a positive influence and actually care about me.

Ditching the Habit

Quitting smoking

I was talking to my mom while she lay in a hospital bed.

She was sick again due to complications from her smoking. She had about 40% of normal breathing capacity and was on breathing treatments three times a day. The man next to her, my father, had survived two heart attacks and a quadruple bypass a couple years prior (also due to smoking).

They had both been lifelong smokers. To their credit, they’d tried to quit many times over the years. They’d used nicotine patches, tried smoking pills, and even told my brother and I to hide their cigarettes.

And here they were, both still talking about how they needed a smoke. I was terrified and had had enough.

I looked into my parent’s eyes and told them how scared I was. I was scared they would keep getting sick and I would lose them. I was scared they wouldn’t see my future children. And I told them it was killing me inside.

I could tell those words made an impact and sparked a new determination in them. From that day forward, my parents both quit smoking after 40 years of addiction. Unbelievable.

How it shaped me: I firmly believe you can’t change someone else. But this situation showed me that having the hard conversations you’ve been avoiding can be a catalyst for other people to WANT to change

I’ve also been grateful to spend many more years with my parents. They haven’t been sick and my dad’s heart and lungs are in great shape. We’ve been able to travel to Europe, go hiking, and stroll along the beach.

If I hadn’t spoken up then, they might not be with me today.

As I said, life is a series of choices. You will always have more opportunities to make different ones.

We aren’t perfect. Sometimes we make choices we regret. But even those carry meaningful lessons and help us see the better path for the next fork in the road.

Tomorrow is a new day with another new decision. What choice will you make?

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