Brutal Honesty over Pure Hope

As I begin a new entrepreneurial journey, my mind constantly oscillates between excitement and worry.

The excitement part is clear as day. I am finally saying: "Fuck it, I'm going to do things I truly believe in." The way I currently see it, if I'm going to spend all this time and stress and risk instability and the relationships I have, I might as well pursue something I truly want to do. There cannot be any settling here; in the words of Mark Manson, "it's either a hell yes or it's a no." 

As I get a little older (I'm 29), I find that the same goes for people. You only have so much time and energy and need to allocate it towards the big things-- the people and ideas you truly value. The ones who, in many ways, both help define who you are and are there to support, push and teach you. 

At some point in life, you hit a crossroad where you need to decide if what you are pursuing is worth it to you, if it's something you are willing to dump your heart and soul into to develop and see through.

Too often in my own past I've been lukewarm on ideas, and after trying them out for a short amount of time I decided they were either too difficult, too unrealistic or unworthy to pursue further. These are all pathetic excuses derived more from indecisiveness of what I want out of life, than out of laziness. There is a serious difference between being opportunity-driven and being mission-driven. Your heart is normally only in the latter, where you'll do whatever it takes to make an impact in the market you seek to serve or disrupt. Mission is a stronger driver of perseverance than opportunity.   

At the same time, being too idealistic may be unrealistic and just about every entrepreneurship handbook will teach you to always be testing assumptions, not to marry ideas, to figure out when to pivot, and if your idea is going to fail, figure out how to fail fast. But this post is not about that; I'll leave those topics to another day. 

A mentor asked me the other day: "What really fascinates you?"  

I fumbled through a response. Too many things, ideas, people fascinate me. The concept of creativity and how it is manifested fascinates me. Community, rhizomes and processes fascinate me. 

Then, after explaining he suffers from the same problem of overextension, he changed his question: "What do you really want to do-- what would you like to do to drive yourself forward?"

Well, a shit ton of things. But let's be specific. 

I want to make content that bridge cultures, people, politics; I get an unbelievable high off of watching a documentary on polygamous mormon colonies in Arizona, the feeling of a camera in my hands while out on an iceberg in Greenland, sharing a meal with reindeer herders in a yurt in the middle of Siberia, driving through rivers to find hot springs, and the teasers from BBC's Planet Earth II send epic shivers down my spine. These are the stories and experiences I want to bring to life so that others can learn and find inspiration in them. 

I want to facilitate a bridge of information that promotes a more nuanced and acute understanding of other people and nature. Authentic content, real stories, and a genuine ability to learn from these stories. And to narrow that down more, I want to build that bridge with China. It's a country I've dedicated much of my adolescent and young adult life to; a language I've struggled to master for more than a decade; a place where I feel comfortable despite being regularly treated as a "dancing monkey."

At the same time, I want to build a community of people, not just a company, but rather a space, a "marriage of convenience" perhaps, somewhere where people can collaborate, combine skills, networks and knowledge to make great things.

I realize I have two very different ideas that pull form the same fascination. Fuck it, if I want cake and I'd like to eat it too, as long as I'm realistic with myself and those around me, I can do this or at the very least fight for it with all I've got. 

Now that I've come clean with what I want (and those are a lot of wants, so this is going to be challenging), I need to embrace my fears, worries and failures, all of them. And I need to be open about them, about my shortcomings and mistakes, not just to myself, but also to the people I'm developing these ideas with and all those individuals in my life who may be impacted by the decisions I am making. 

This all leads back to the worry half of what this post is about. 

Contrary to some cliché inspirational quote, life is not a classroom. A classroom implies a place where knowledge is presented to you while you just sit there. Perhaps a more nuanced metaphor would be to compare life to a fucked-up off-road adventure. Things go wrong, your car breaks down, you fix it, you argue with your friends, you climb over mountains, you run out of gas, you get stuck in the mud, you work together to dig yourself out, and sometimes you can make it all the way to the summit, but at the very least you all accept that as long as everyone gets home safely its not a total wash.

The experience is driven by its process, not simply by the end result. I'll take that one step further: the end result is achieved as a result of constant learning, analysis and acceptance of the entire journey, not just the easy parts, and continued learning informs future decisions. Similarly, learning itself is not just about which facts you can recite, it's highly social, dynamic and experience-based.

I'm still learning how to get over the fear of hitting the same potholes I've fallen into in the not so distant past. I worry because of the pain this has caused. On multiple occasions, I've questioned if the strain on my relationships and turning best friends into colleagues is worth it in the end, success or failure. Is the strain avoidable while still trying to grow something great together?

While the strain I am talking about is never completely avoidable, I think the potential to cause hurt can be greatly diminished if expectations are clear and everyone involved feels like they are working towards the same purpose. This requires being upfront in a couple of ways.

First, having hard conversations is not only the responsible thing to do, it is the best way to show your friends and colleagues, the people you care most about, that you truly respect and love them.

Second, setting honest expectations, being open with one's own insecurities and self-admitted shortcomings (whether true or not), and the uncomfortableness and pain in doing this is what forges trust in your relationships with others.

I've come to understand that suffering through insecurities instead of avoiding them is what builds courage, confidence, greater self-respect and respect for the people you care about-- the lives that are intrinsically connected to yours.

It's almost ironic, but positivity comes from accepting and reflecting on negative experiences-- past errors, failures and insecurities. Only pursuing positive things, while beautiful in theory, is hardly rooted in real experience, but rather in hope. And hope, without confronting latent insecurities, can unfortunately produce undesired, deceptive results, because in many ways to hope is to guess (odds are not in your favour). This is the definition of false optimism, and I've certainly been guilty of committing this mistake before. I'll tell you, the fall-out feels far worse in the long-run. 

It's like this: the more you find yourself wanting to achieve something, the more blind you become to figuring out how to get there. Why? Because you've become obsessed with want, hope and desire. You look only at the desired result but ignore the journey you'd need to take to get there. And this desire for a positive outcome more often than not leads to negative, painful repercussions or even a complete unravelling of everything you've built. 

On the other hand, if you learn from the negative experiences in life, admit your insecurities, be open and honest about them, take those lessons and inject them into your life, then you are at least on a more realistic path towards growth. Congrats, you've broken away from the vicious cycle of mounting insecurities and doubts. Get out and move on.  

My point in all of this, after having been on the brink and now back on what feels like more solid footing, is to not let unintentional deception cloud yourself and the people around you. If what you seek to pursue is really worth it, then do it, fight for it, test it, because if it's truly worthwhile, you have to be ready to overcome a lot of difficulties to get there.

Success does not just happen, it is built through a process, and that process is defined by layers upon layers of lessons derived from experiences-- positive, negative and everything in-between. To try to remove the negative experiences, ignore your shortcomings and avoid facing your insecurities only does yourself a disservice. 

Tough times will inevitably happen. This is life. This is entrepreneurship. It's not a path defined by security and a guaranteed monthly paycheque; it's a fucking adventure. Like adventures, life comes with pain; it's part of the journey. It is not possible to remove that pain. While you can numb it, try to avoid it, deceive yourself and those around you, intentionally or not, doing this will likely only prolong disappointment, or worse.

To live is to feel pain. Pain is part of our natural evolution, like dogs wearing electric collars, we (should) learn fastest from pain, where the dangers to our complex well-being are most evident. A real unravelling happens when you alienate your people and let yourself down by not confronting the negative outcomes in your life. Pain is part of that, and in a messed up way, it's a good thing.

If you care about your people, have the hard conversations, lay everything out on the table. I don't mean to dim excitement here; passion is a beautiful thing that can help you answer those hard life questions about what you ultimately want to do with your time on earth. However, starting from a position of brutal honesty is infinitely better than starting from a position of pure hope, because only one of those is derived from lessons learned through actual experience.