Self Sabotage And My Million Dollar Lesson On It

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I wanted to share a concrete example of my own experience of how unconscious self-sabotage likely cost me millions of dollars. By writing about this maybe someone out there will see themselves in the story.

Self Sabotage

I’m in this text group with a bunch of successful startup founders and recently a question came up around what your biggest investment mistake was?

There were lots of interesting stories and anecdotes which all brought a lot of collective comfort to everyone that they weren’t alone in their mistakes.

What I kept thinking about was why these scenarios happened to everyone including myself?

Most people write them off as bad luck, ignorance, or poor decision making, but I think there’s a lot more going on here as I’ve alluded to in the responsive reality and my thoughts on manifestation.

The more we understand these hidden forces that shape our lives, the better set up we are to have our life go well.

Abandoning Myself and A Pile of Cash

In 2014 I was living in Rio De Janeiro Brazil with a group of friends running a “creator business” that sold online courses on startup sales and business development. I was 25 making over $200,000+ a year running my own business while working probably around 15-20 hours a week. I wasn’t quite Tim Ferriss living the 4 hour work week, but I was on my way and felt like I had arrived.

In March that year, I went to SXSW and met all these people just like me that had their own podcasts. I loved podcasts and considered myself a good speaker so I thought I’d throw my hat in the ring. 

At the time, I was very focused on “crushing it” across all avenues of life so I decided to make the podcast about interviewing high achievers on how they got their “competitive edge” to become so successful. I named the show The Competitive Edge and launched it May 1, 2014.

The Competitive Edge

At the time podcasting and the creator economy wasn’t this big thing. It was much more fringe and most friends that were working in banking and consulting thought that I was pretty weird for using my Princeton education to become some blogger / podcaster who sold courses while living on the beach in a foreign country. 

So the idea of my podcast becoming a big business opportunity wasn’t really a huge motivator for me. I was more looking for my next act and it seemed like talking to interesting people would be fun. My hunch ended up being right and it turned out that I loved podcasting. 

Over the next year, the podcast started to become quite successful. At one point it was ranked #4 on iTunes in business and even featured alongside business inspirations of mine like Tim Ferriss!

After a year of publishing, the podcast grew to 100,000s of thousands of downloads a month.

I would email the shows out to my email list and post on social media. But most of the growth was organic because I was highly ranked in the iTunes app store where people would discover new shows. At the time, it wasn’t so crowded and there was lots of white space to grow on the back of iTunes if you were creating a good show.

Despite all this success, there was this feeling inside of me that I was “playing small.” I felt like there were all these people in my previous tech circles starting tech companies and raising millions of dollars and I was a guy selling courses, blogging, and doing a podcast. This was accentuated by the fact that many other online marketing people I was meeting felt kind of squirrely and not like people that I was aspiring to be like. There were obviously some gems too.

So despite the fact that by conventional standards all these things were going incredibly well, I felt like a chump and had massive imposter syndrome. 

Who was I to be giving people advice on how to be successful in life? 

When these uncomfortable feelings came up, the story I kept telling myself was that “I miss working with other people as part of a bigger mission” and “I really want to get back to tech.”

It’s not that I didn’t miss working with other people, but I now see that this compulsion to stop doing something that gave me creative energy and joy was much more a symptom of an unconscious sense of worthlessness and low self-esteem. In my unconscious mind, I wasn’t enough and even with a successful podcast and lots of money, I still felt that way. 

So I thought I had to go do something “bigger.” This was all a strategy to protect myself from facing the mental formation of being worthless.

There was also a desire to get away from any type of business where the product was “me” which included the podcast. I thought this was just because I didn’t like the burden of having to deal with people criticizing or expecting so much from me which happens when you grow a big audience. But the stronger unseen force was that it was very hard to sustain a “business of me” when the most expansive part of your consciousness (the unconscious) doesn’t think it’s worth much.

It’s obvious now that moving away from any “business of me” was a protective strategy:

If the product isn’t me, and I stay small, I avoid judgment.

You can see how that even if I stuck with it, getting too popular in any form of a “business of me” represented a threat. This is a very common force that causes people to unknowingly self sabotage themselves. If you look closely at people who seemingly leave things at the top of their game, there’s often something deeper going on than what is communicated at the surface level. Obviously, we can never know what is going on inside of these people’s internal experience to know for sure.

All of this may sound crazy, but this is how the ego and its self preservation mechanism works at less expansive levels of awareness that lead to self-sabotage. I wasn’t aware of these forces that were driving my behavior when this was going on. Instead, my consciousness came up with all these other stories to substantiate why I wanted to move away from things that were much easier to stomach than the potentiality of facing my low self-worth. 

The ironic and kind of funny thing is that everyone including myself at the time, thought I was incredibly confident. You must have huge balls to move to Brazil, start your own business, and create a talk show that interviews successful people way older than you at age 25! I know see that for most of my experience, I was just a very resilient and effective strategist at avoiding the feelings and mental formations in the depths of my unconscious.

It’s frickin crazy how this all works.

The Hidden Escape Hatch of Self Sabotage 

In early 2015, I moved back to New York and started working on Troops with my co-founders Dan and Greg. A few months in we raised $1.5M from First Round Capital and shortly after I shut the podcast down. 

Despite the fact that I loved doing it, knew it was a valuable asset, and was connecting with all these amazing people that could propel me in all walks of life, there was also a mental formation that “I was being disloyal” to my teammates and investors by engaging in any outside business activities. I don’t blame any of my teammates or investors for this idea. It was definitely rooted in all my own programming which was created by merely existing in my own subjective experience.

The first part of this programming was from startup culture which loves to think in polarities and extremes like you should burn the boats when you start a company. It was also a derivative of my competitive athletics background which often imbued messages of self-sacrifice vs. self love; concepts like “there’s no I in team”, “first one in, last one out”, and leaders eating last. It’s not that there isn’t some value in parts of these ethics. It’s just that they must be balanced and weighed with appropriate context. Clearly, I did not have the awareness to do this effectively at this point in my evolution.

If you would have asked me who was running the show in these decisions I would have told you that I was! I was making logical, calculated decisions. But the truth that I can see now is that my conditioned consciousness was. There were these unseen forces that were driving all behaviors and decisions, and I just didn’t know it.

This is how the evolution of consciousness and human experience works. You think you’re aware, but you’re actually like a robot that’s asleep following unconscious programs. Until you’re not. And at this point, you can start to take more authorship of your reality vs. being the subject to inherited programs. 

This is why I am so passionate about helping myself and others expand their consciousness. It’s kind of impossible not to be interested in helping others once you go through all this.

Everyone’s Got Their Own Story of Self Sabotage

We all have life and business decisions that “if only I would have done x, I would have y.”

Just bring up the word “crypto” and someone will tell you how they’d be a millionaire if they had listened to their friend to buy bitcoin in 2013. I feel like I have at least 10 of these stories in my own experience.

In this particular example, I have no doubt that if I would have kept doing the podcast that I loved doing, it would be a multi-million dollar a year media property today. In fact, I’ve run the projections on my original growth curve and it tracks! 

But this is life : )

And each time these things happen we have the wonderful opportunity to learn these lessons. In this story, there are certainly many lessons on self-sabotage, but the big theme for me is the importance of becoming aware of the subconscious programming that drives your experience. 

It’s my belief that the less awareness you have, the higher likelihood you run the risk of some form of unconscious self-sabotage. There is also the big lesson of moving beyond either/or thinking & polarities and realizing that in almost all scenarios, there is an opportunity to find creative ways for “both/and.”

With this in mind, I will always find a way to make time for creative expression like this writing and my new podcast EvolutionFM regardless of where my career takes me.

The Big Lesson FOR YOU In My Million Dollar Lesson

We are constantly manifesting both the conscious and unconscious mind. The algorithm of reality brings forth situations and experiences so that we can increasingly become aware of the unconscious until eventually consciousness can realize itself (enlightenment).

Once we dedicate ourselves to removing all these layers and treating this pursuit as the primary purpose of our lives, it’s my experience that everything in life only gets better. It’s not like you have to “give up” everything and live an ascetic lifestyle despite what some outdated programming tells you. And yes, you will go through some tough times as your previous reality and self-view deconstructs.

But on the other side you will emerge to a much more expansive and exciting world. I was listening to a podcast with Bo Shao & Tim Ferriss recently and he compared his life now vs. before like watching TV in Black and White TV vs. Color.

manifesting both the conscious and unconscious mind

I love this analogy and find it to be true in my own experience.

And it’s not just like it’s only your inner experience that gets enriched which is a common misconception. The outer world starts to more effortlessly match our deepest inner desires once we clear all the junk out of the way. I think this is actually what’s happening with manifesting.

I’m sure I’ll have some more examples of self sabotage that will come up. I’m okay with that.

I’m just happy to have the tools to use my response to everyday life as a path to having less of them while making sure to have fun along the way : )

If you’re reading this and wondering, how you can apply this maybe think about your own experience.

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