The Top 5 Decisions I’ve Ever Made

If you’ve been following my work for a while, you know that I draw heavily on my experiences to shape the things I tell you. Well, I thought today, for once, I might talk about myself a bit more than usual and give you more of a window into my life.

Of course, I can’t help but sprinkle in little pieces of advice, but I decided to write this article based on a question I saw on Quora.

The question is in the headline – “What are the top 5 decisions you ever made?”

All the decisions are interwoven. A hint for you — all yours are too. I can never understand things perfect looking backward and of course, hindsight bias comes into play, but here are the most formative decisions I feel I’ve ever made.

I Started Writing

A little over five years ago, a friend of mine asked me to write articles for his website. I’d been studying self-improvement a ton, reading a lot, and sharing updates about it on social media.

My ‘updates’ were pretty long, more like essays, and my friend must have picked up on my interest in writing — something I’d thought about doing in the back of my mind for a long time. I wrote one article for the website, then two, then three. And I just never stopped.

Now? I make a living doing what I love. The key lesson here? If you have a chance to follow that inkling and scratch that little itch, do it. Maybe you won’t be lucky to have someone literally ask you to do the thing you’ve been thinking about doing, but you can give yourself permission to do it today.

People build empires on inklings. I saw a tweet from Joe Rogan a decade or so where he said something along the lines of “Podcasting seems like a blast. I think I should try it.” Think he was right?

All those little thoughts and inklings are the seeds. Looking back on it all, I just feel so lucky that, for whatever reason, I decided to follow that inclination. That decision dramatically shifted the trajectory of my life forever.

Just like Joe’s decision did. Just like yours could, too, if you make it. That’s the thing, you don’t have to decide you’re going to achieve world domination. Just follow that inkling and see what happens next.

I Kept Following the Bread Crumbs

I followed through with the ‘see what happens next’ technique until I built an entire career from that little inkling. After writing a few articles, the idea of making a full-time living never crossed my mind at all. But I was curious. What would happen if I kept writing? So, I just kept doing it.

I noticed little opportunities to level up along the way. A woman I knew had her work published in this online magazine called Thought Catalog. I checked the site to see if they allowed contributors. They did. I submitted an article. They accepted it. This lead to a crucial time in my writing career — writing 18 months straight with a dedicated editor from the site helping me improve my skills.

I kept looking for more little opportunities. Anytime I saw something that I thought had the slightest chance of improving my writing career, I jumped on it.

People try to gain clarity the wrong way, by theorizing. They think that they can somehow assemble the playing field in their mind without actually playing, which they can’t, so they stay stuck.

If you stop trying to find all the answers up front and just start ‘doing’ the answers will reveal themselves to you.

It’s crazy.

People ask me all the time “How did you pull this off? Millions of yearly readers, three published books, one of the few people to try to make a full-time living blogging and actually get it to work. I just never stopped. On a long enough time scale with experimentation and iteration, you eventually get what you want.

I Took a Leap of Faith at a Crossroads in My Life

I separated from my wife and quit my job in a span of weeks.

I’d already been doing pretty well with my writing by this point, well enough that I could quit my job, but I was hesitant. Why? Because being all on your own is scary. Maybe if my marriage hadn’t fallen apart, I would’ve spent another six months at my job. Who knows.

Anyway, as my writing career was reaching this tipping point, my marriage was falling apart. It was pretty clear to me at this point that the relationship was unsalvageable, so I moved out of the house.

I went to visit a friend in D.C. As I was going through TSA, I get a text message “are you joining the call?” It was my business coach. With everything going on, I’d totally forgot about the meeting. I didn’t want to take the meeting, but I did.

So I’m walking through the airport on a Zoom call with my business coach and instead of talking about business, I’m just venting. I describe the details of the crossroads I was in and she suggested that I ask my job for a month-long sabbatical. That way I could try ‘being on my own’ for a month to see what it was like. I followed her suggestion.

After a few days of being on my own, I knew I was never going to work for anybody again.

Just like that, I found myself single, no job, in a brand new city, starting all over again. Taking a leap of faith while in the midst of chaos hurled me into the new arc of life I’m in now. The universe almost forced my hand into leveling up. I’m glad I followed the signs.

What does this mean for you?

I can’t tell you what decisions are going to be right for you. I just know that tough decisions are…tough. You develop so much weight and baggage prior to making tough decisions that they seem too daunting to make.

I’m not guaranteeing you’ll be successful if you make the decision to leap either. But I am saying decisions have consequences. All of them. Do with that information what you will.

I Had Unprotected Sex

My ex-wife and I had always had a rocky relationship. You know this couple – they makeup and break up every five seconds. Fight, makeup, sex, fight, makeup, sex. Well, during one of those makeup sessions we conceived my daughter, Nyvia. She turns 5 on this upcoming Valentine’s day.

She’s precocious and bright, you can just tell (*cough* like her father). She’s an attached, touchy-feely, never leave your side type of kid. She loves to sing, dance, perform. The kid’s a star.

I regret nothing at all about my past relationship because it brought me Nyvia. And we’ve experienced an even deeper bond this past year since I’ve had so much more free time with control over my schedule.

The thing about having a kid? Now, you have no excuses to live below your potential because it’s no longer just about you. At least that’s the way I feel. Your kids reflect everything back onto you. You can’t hide from them. Hell, they might be the only people in the world who can really see you.

I love watching the level of presence she has. Kids have no concern about their futures whatsoever, just bound to whatever is happening right now. Kids are happier and more intelligent than all of us. We unlearn the meaning of life as we supposedly become wiser.

I think everyone should have kids. I think the people who say they don’t want kids just don’t know they want kids. How can you not want to see a piece of you manifested into the real world? I dunno. To each their own.

But I’m glad I ‘made the mistake’ of staying in a bad relationship and conceiving Nyvia. Do I believe everything happens for a reason? No, but I believe you can draw lessons from everything that happens and the things that happen can help shape you.

I had Nyvia right around the time I started writing and I took writing more seriously overtime because I wanted to build a better life for her and not be one of those parents stuck in a miserable job, thus passing that misery to their kids through osmosis. I wanted to be someone she looks up to. And she does. I love it.

I Royally Screwed up my Life 

I’ve made some blindingly dumb mistakes in my life.

I dropped out of school with only 3 credits left for graduation after piling up $70,000 in debt. I still don’t have that degree. After getting arrested for selling weed and getting put on probation, I kept selling weed and doing drugs until I was arrested again.

With a criminal record and no education, I found myself working not-so-great jobs. One could say I had thrown my future away. But, I say these mistakes were the best things that ever happened to me. Didn’t feel like it back then, but looking at my life now I realize a few things.

Had I graduated college and done everything right, I probably would’ve gotten a really good job. Not a fulfilling one, but a good one that paid a lot. One that might have given me ‘golden handcuffs’ and reduced my desire to follow my dreams.

I started to focus on my writing so much because I didn’t think I could even get a great job with my record. Also, making all those mistakes led to me looking for answers to the problems I created. I found self-improvement and used it to improve my life. Then, I wrote about the lessons I learned in the process.

The blemishes on my record made the story more real. Also, I’ve had great stories, cautionary tales, to share in my writing — from putting my arm through a window and needing 35 stitches to doing lab-made hallucinogens instead of going to my probation meeting to waking up in the middle of the night in jail from my best friend sobbing like a toddler, let’s just say I’ve lived.

The point isn’t to screw up your life. The point is that you can learn a ton from your mistakes. Also, sometimes bad things happen in your life so better things can happen in the future.

Again, I don’t think everything happens for a reason. But I do think the attitude that everything happens for a reason is the right attitude to have even if it’s not true.

That way, you look at the universe as somehow being on your side. This leads to you thinking that every move you make will turn out well in the long run. You have a lens to see the world that benefits you. Develop it. Use it.