Blowing up my world and seeking out new adventure

The following is a journal entry of mine from three years ago, back on January 11, 2016. Fast forward to today, when I spend a lot of time with independent professionals and Leapers — anyone actively changing the future of their work — and I have many conversations about what it was like to leave my work, what I wish I knew, how I did it, and so on. I rediscovered this journal entry and thought I would share it to provide a bit of insight into my initial intentions. Perhaps you will find something useful in there?.
Time to get out of the regularity of daily life; to break free of the mold and explore the world beyond computer screens, comfortable living and typical American city social interactions.

To liberate the mind, soul and entire being, and open up possibilities beyond imagination that only feel real while being experienced in the present moment.

To create the types of memories that imprint themselves on your mind and dramatically change your character, existence, and world view.

These are the types of experiences I’m seeking as I come to a close of the first phase of my professional career.

Allow me to elaborate.

In my mind, I just put in my resignation letter to the leadership team at the company I’ve contributed to for the past three years. While it hasn’t physically happened yet, mentally I’ve moved on, which means I’m over the past and am currently planning for and actively ushering in the next phase of my life. And I could not be more excited for it!

This essay will not focus on more than an ounce of negativity towards my previous employer, beyond this upcoming paragraph. See, I’ve spent the past year working towards ambiguous goals and navigating the complexities of a startup that’s growing faster than it needs to be due to leadership that consistently makes, in my opinion, questionable decisions. Couple that with the fact that very little attention has been paid — or action taken — to improve the health of the company, from the design of organizational systems and processes to the regularly friction-inducing communication and accountability issues. At this point I honestly feel I’ve done all I can do, and even though I have a burning desire in me to create the positive changes that will lead us towards success, I will not be supported by leadership, and therefore will fail before even getting started. There. That’s all I’ll say about that.

Commitments to design my future

Now that I’m committed to moving on and designing the next phase of my life, there are a few key strategies I think would be valuable to put in place before embarking on this journey. I envision them as guidelines, serving the purpose of helping keep my future self in check as time progresses and situations come and go. Seeking out unpredictable experiences brings about a higher probability of unknown unknowns, which, if unprepared for, may lead to higher stress levels and feelings of chaos and uncontrollability. AKA things I don’t like! And for someone who naturally operates at heightened levels of anxiety and stress (i.e. me), it’s in my best interest to do what I can to prepare for managing how I’ll handle myself in these hypothetic-yet-probable situations, and for how I’ll maintain clarity when the unknown unknowns finally surface themselves.

Of course, it would not make for a good story if there were not moments of fear, vulnerability, uncertainty, and adventure, woven throughout a tale of discovery, inspiration, exploration and creative endeavors. After all, the goal of this journey is to get lost in life and experience the world beyond my typical run-of-the-mill day to day, with the intention of opening myself up to a world of possibilities where inspiration and creativity run rampant throughout my mind, ultimately leading to clarity, insight, and focus for when the time comes to return to my world and transition back in to “reality.”

As I prepare myself for what lies ahead, this essay will attempt to document these strategies, explore the intent behind each, and lay out my ideal outcomes for both these highly anticipated adventures as well as these strategically designed guidelines.


1. Don’t overthink it

This is going go be damn impossible for me!

I make my livelihood on thinking, seek out wisdom by thinking, and make my choices by thinking. Sure, I have emotions and gut instincts and plenty of heart and soul, but I’ve aways been heavy on the logical implications of a given choice, which often leads to endless weighing of my options, probably because I’m scared of making choices and deciding on something when I know full well that that choice could be the “wrong” one. Whether a meal or a product purchase or a commitment that relates to my personal lifestyle, overthinking has become synonymous with breathing for me, which is something that I’m driven to change in my life.

Somehow this is not the case in my professional decision making career, but that’s a topic for another essay entirely!

For now, I’m laying down the guideline that these upcoming adventures will be led by my heart, more so than my brain.

The intention behind this trip — we’ll talk a lot about intention — is for me to get lost, find myself, and begin building towards my future. Simple as that. Logic certainly need apply to many situations, but the drive behind this guideline is that logic does not need to overtake emotion, weighing options cannot go on endlessly, and overthinking cannot prevent me from making decisions while exploring myself and the world I live in.

2. Learn to operate with less structure than you’re used to

Another theme in my life that will be tough to overcome! Which is why I’m directly challenging it…

I like structure. Routine. Known variables. I like my day laid out a certain way, with time blocks for everything — even down time — so that I always know what I’m supposed to be doing. That way I maximize for productivity, creativity and efficient use of time, and minimize wasted time, risk, and inefficiencies. Except I’m learning that this does not always work, as life is not full of structure, yet is full of unknown unknowns! Things happen, situations arise, and not everything can be controlled. Which is a major challenge for me, and another change I’ve been waiting to make in my life.

So, this is a perfect opportunity for me to learn to live and operate throughout my day with less structure, less definition, and less rigidity. Remember, I’m talking about less, and not none. Major difference!

To explain, the biggest issue my need for structure creates is that when it comes time for down time, and/or I have a large block of time in my calendar to do nothing, which has been intentionally planned, I end up feeling lost, useless, and unsure of what to do with myself. This leads to anxiety and feelings of self-deprecation that certainly aren’t healthy, especially given I was designing time for me to relax and unwind, and not stress and “be productive.” No bueno.

We live in a world of porn: productivity porn, entrepreneurship porn, creativity porn and more. Blogs and publications always talk about how to increase creativity, become more productive, and use your time more wisely. While these are valuable goals to focus on, they seem to be driving people a bit mad, as I (and many others I speak with) often feel unproductive even when we’ve produced a ton! Whatever my personal output, much of the time I’ll feel as though it’s not enough, which leads to added (and unnecessary) anxiety and stress.

And as mentioned, even in times of scheduled downtime, I’ll have anxiety arise that I’m not using my time properly, and that I should be doing something else other than why I’m doing. So, I guess I’ve compensated by settling on the idea that I always need to be productive, even in my downtime. Which is absolutely batshit nuts! Hence the reason for guideline number two.

3. Embrace serendipity yet be prepared to capture inspiration

This is an interesting one that I just made up right now!

I believe in inspiration, and love the feelings and thoughts it brings. I seek it out through walking, reading, hiking, listening, questioning, researching, exploring and more. I’m always looking for that spark, which often ignites itself when I’m least expecting it and least prepared to capture it. Yet, inspiration is regularly my desire, as I love the feeling of flexing my creative muscles to connect threads in my life and string together words that capture ideas that impact people’s lives. It’s really an awesome feeling; telling stories by balancing ideas, flowing with words, and sharing the world as I see it. Apparently I have a unique perspective…Who knew!

Anyway, this guideline is designed to make sure that I let go of any routines (as we’ve talked about) and lean in to the uncertainty that is unpredictability, while continually seeking out those serendipitous moments that lead to inspiration — and then making sure I’m prepared to capture it, regardless of when or where it strikes.

In simple terms, I will seek out serendipity and inspiration, and always make sure to take the time to capture my ideas when I feel the urge. Always.

Desired Outcomes

  • Let go of the chaos, stress and frustrations of the past few years of troubled startup life
  • Grow into my new skin and become more comfortable living with uncertainty, operating without structure, and making decisions more easily
  • Create streams of income, one step at a time, that will will help fund my adventures and explorations
  • Step up to the plate and become the entrepreneur you’ve always been
  • Design brands for myself and my business, and clearly articulate who I am, what I do, why I do it, and how I can help you
  • Experience the world outside of what I’m used to, feel small and insignificant, and turn this into inspiration, writing, and creativity
  • Become more comfortable traveling and interacting with people from different cultures while learning to connect with humans who are different from you