The times in my life when I’ve felt the most successful are when I was completely focused on my goals to the point where I chased them on autopilot, and I knew exactly what needed to be done.

On the other hand, when I’ve felt the least successful was when I work on things without a clear plan or vision, or feel generally confused about a situation.

I’ve gone back and forth between those mental states a lot in my life so far, and to be honest most of the time I have been somewhere in the middle. But it wasn’t until recently that I started to understand that, and notice the patterns.

Looking back, I can see many different examples of when clarity, focus, goals, and most importantly, JOY, brought me success. And many times where confusion, self-doubt, or poor planning led me to despair. I’m not talking only about business success, either, but success in every aspect of my life: personal, social, business, and romance.

Early Success with Sailing

The earliest meaningful example of success in my life, that I can remember, was when I first learned how to sail. I was only nine years old, a guest at sailing camp on Long Island with my cousins. They let me drive the boat, and as soon as I grabbed the tiller, I knew that sailing would stick with me.

Sailing demanded and received my full, undivided attention. It brought me peace, joy, and friendship. I became verifiably obsessed with it, and as a result, I developed a level of expertise that many people never master. Sailing to me is automatic, like a flow state between myself, my boat, and the wind. I’m not the best sailor in the world, but I can sail using my raw intuition, and to this day it remains one of my most treasured activities.

In fact, for a time I thought I would pursue a career in sailing, even getting my 100 ton and becoming a professional captain. After doing that for a while, I began to feel stagnant, and understood that there was more that I wanted to do, outside of being paid to drive someone else’s boat.

I yearned for more. To make sailing my hobby instead of my profession. I became obsessed with freedom, and I knew that I needed to get out of a sailing job and into something that I control.

Before I get into how I briefly achieved that freedom, I want to talk about a consistent point of failure in my life, which has been a sticking point for me since childhood.

Confusion in Romantic Relationships

For as long as I can remember, I have struggled with romantic relationships. I lacked confidence, never knew the right things to say, and never felt that I was good enough to have a girlfriend. As a result, any time I did have a chance with a woman that I really liked, I totally screwed it up, because I didn’t bring my best self to the table, and I made poor choices.

Soon, they would want nothing to do with me, and I became filled with confusion and despair. The problem is, I was always determined to win them over, and I would allow myself to be strung along in hopes that I could find the right words to say that would get them to see my value.

The hard truth there is that those women were never right for me in the first place, and my acting from a place of confusion rather than clarity is what led me into those situations. It took me years to recognize this pattern and break free from it. I kept finding myself in the same situation, with different women, all through high school, college, and even into my 20s.

The last one completely broke me, and while I was confused for a very long time at the end, I’ve come to understand that I shouldn’t have cared so much about that person, because they never cared that much about me in the first place. That lack of clarity and focus had me spinning my wheels instead of moving forward.

Now, I may be single, but I’m comfortable with it. I’d rather be single, with no prospects, then chasing around a woman, trying to bend myself into what I believe she wants me to be. I now know that the right person will recognize my value and want to be with me because they appreciate my genuine qualities.

Those qualities shine when I am focused on my goals and living the life that I desire. There were times where I would get the girl, and that always happened when I was in a good mental state, and not entirely focused on the relationship. They came when I was doing what I love, and doing it well.

I think that mindset applies whether you are man or woman, straight or gay. When you believe in yourself, and focus on what matters most to you, instead of acting out of despair and confusion, you will find success.

Success with Extra Chill

While romantic relationships cannot be compared directly to business success, I do believe there are parallels to be drawn in my own life that suggest my mindset is often what determines the outcome.

I mentioned earlier how I desperately wanted to get out of sailing for a living, because I desired freedom. At that point, while I still loved the act of sailing itself, the employment aspect of it began to feel like a burden. However, instead of letting that deter me from chasing my actual dreams, I used it as fuel for my focus, which helped me reach my goal of self-employment.

Extra Chill is a music blog that I started in college. For a long time it was just a hobby, but I always wanted more from it. Over time, I learned a formula to success with SEO, and eventually scaled it to the point where it paid me twice as much as my full-time job as a captain.

I was able to quit my job, live off display advertising, and chase my dreams without constraint. I had a plan and a drive to make that plan a reality, and it paid off big time. I was fully determined, I knew exactly what needed to be done. And I did it.

Of course, if you’ve read any of my other posts on this site, you know that the success didn’t last for long, and soon I was back into a spiral of confusion and despair.

Spinning my Wheels with Extra Chill

Google’s September 2023 Helpful Content Update began the process of undoing my hard work, and I watched Extra Chill’s 300,000 monthly visitors shrink down to just 20,000 over the course of about two years. The mindset of failure I experienced here was oddly similar to the mindset of failure with women that had plagued me my whole life.

I wasn’t sure what to do, so I started to try everything I could think of to please Google. Like an uninterested lover, nothing I did pleased them, but I continued to try. This is indicative of the failure mindset, and while there may have been external forces at play, my refusal to accept reality caused a lot of stress and wasted time.

This creeped over into other aspects of my life, and kept me in a rut for longer than I’d like to admit. However, eventually I had a similar realization that I’d had about failed relationships. Sometimes you just have to let go and find the path that you’re meant to be on once more.

What’s Next?

At the moment, I feel that I’m on the verge of another breakthrough in life. I have broken free of the despair caused by the traffic spiral, have managed to avoid toxic relationships for several years, and I’m now focused on things that I believe have a proven path to success.

I have created this website to showcase my skills and mindset as an entrepreneur, honed over years of determination. I know that I have the ability to achieve great things with my brainpower, and pure iron will. I want to help other people with my skills, by helping them build their businesses and providing high ticket services.

In the process of learning sales for these services, I developed a bespoke plugin that solved a unique pain point for me. It helps me automate the lead-gathering and outreach for sales emails. While I built this for myself, this is a universally needed service in the world of sales, because everybody is doing cold outreach. So, in the process of creating a tool for myself, built out of focus and drive, I ended up creating a product that can be sold to others.

Focused Refinement of Extra Chill

Not only am I using this tool to sell my services, but I am also refining it to package up and offer to others. This has been built out of drive, clarity and focus, not from spinning my wheels. Additionally, I have refined the focus of Extra Chill onto my authentic voice and a desire to uplift the underground community, and it has entered a new, albeit slower, growth period.

I have a free ticket to SXSW for the second year in a row, and I am now living in Austin, TX instead of the smaller, relatively stagnant lifestyle of Charleston, SC, my home for 13 years.

This coupled with the fact that big name artists & PR companies have begun to reach out to me for interviews and coverage, and offer me free tickets, leads me to believe that I have found another good avenue for success with that venture. Perhaps not as astronomical as it was with SEO, but highly valuable in its own right.

I am on the same path that I’ve been down a few times already. I know what it feels like and what needs to be done. Except now, all of my skills and experience have compounded to the point where I not only have a plan, but can also recognize my own thought patterns, and see the big picture in my life.

Let’s See How This Goes

The time has not come yet, but with this determination, a clear idea of what must be done, I am going to achieve it. How do I know? I feel it in my actions and daily activity. Everything I do is in pursuit of this goal once again, and I know exactly what must be done.

Of course, I must remain vigilant, because it is easy to slip into the same old patterns. Recognizing the patterns and avoiding them are two different things. But the recognition is a huge step, and it helps to fuel my confidence that I am going to achieve my goals.

Now, let’s see how the rest of the year unfolds, shall we?