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Risk-Taking vs. Risk-Adverse (Where's the Fine Line?)

Anything related to matters of the mind


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Nov 14, 2011
Yesterday afternoon, I went on a date with a girl who has the weirdest lifestyle.

Topics of this Post (Similar to an older post of mine):
  • Risk taking vs risk adverse
  • Making the transition from relying on external resources for certainty (and stability) to developing this internal sense of certainty within ourselves, to help us grow our businesses better.
As we began asking about each other's lives, she told me about her life:
  • Stability: She graduated college with a PhD and has a stable job,
  • Security: She is applying for teaching positions because they eventually provide tenure (a second layer of job security),
  • A Safety Net: The home she purchased when she was 23 appreciated $100,000 in value,
  • A Detailed and Safe Plan: She spent two years budgeting, planning, and saving up for a cruise for her sister's birthday.
Risk-Adversity & Certainty
Overall, she lives a lifestyle full of Certainty.

The other day I was at a business mastermind event up in Longmont, Colorado. The man who organized the group was talking about a neuroscience book her read:

He outlines the SCARF model when it comes to emotional drivers built into our very DNA.
  • S - Status
  • C - Certainty
  • A - Autonomy
  • R - Relatedness
  • F - Fairness
He said that these biological traits are pre-programmed into our DNA and are on auto-pilot to keep us alive. His wife has PTSD from a car crash where she lost family members. When he broke a glass in the kitchen, she got angry at him and her emotions went haywire. After some reflection and study, she never got upset over the glass...'That glass breaking' was the uncertainty that led to the death of her family...

For us, uncertainty (cold calling, moving to a new city, ordering $5,000 worth of products from China for the first time), equals 'death in the wilderness'...because it's not certain.

The analogy he used, which I've heard many times before is comparing modern-day behaviors to that of a tribal village 10,000 years ago. IF you leave the safety and security of the tribe, you're faced with certain death.

In this village, the girl I was on the date with has an abundance of resources saved up. If everything goes according to plan, she has a very secure, safe, and certain life ahead of her. This is what most 9-5 employees and most people value in life. The saving up of an external abundance of resources.

If...everything goes according to plan.
  • What if there is a natural disaster?
  • What if her village gets raided by a hostile tribe?
  • What if something happens?
What if...

A fear that I haven't had for at least a couple of years now...but one that used to plague me so often when it came to making this transition from 9-5 employee into internet entrepreneurship.

At the more practical level, she could lose her job, she could malpractice with her psychology job and get sued for everything she is worth, she could get barred from working or being a professor in this field.

Some of these are non-probably (but possible) examples.

In the tribal village analogy, the question comes up if she would have what it takes to survive in the wilderness on her own?
  • For me: Before embarking on this entrepreneurial journey of uncertainty, the answer was no.
  • For her: Never having been through the life tests (financially speaking) and allowing the resources outside her to provide the comfort and certainty she needs, the answer would most likely be no.
To be fair, I over-dramatize this story to demonstrate a point for people like you and I.

Then, she began to ask me about my life when I was in my 20's.

Risk-Taking & UnCertainty

Like her, I grew up with the same values in my life. My parents preached for me to get a safe and secure job with benefits, the whole college route white picket fence thing. But then, I stumbled my way into the world of entrepreneurship.

While I am sure I have misinterpreted some of the advice given on the topic (and the disastrous consequences that resulted below), I feel it's important to share this journey to see what happens when you go on the other side of the fence and take over-the-top risks that most people won't make.
  • A Detailed and Safe Plan: Six months after reading The Millionaire Fastlane , I drove 2,000 miles across the country with a $500 limit credit card and $250 to my name on two days' notice. I found myself gambling my final $250 at the poker tables of Talking Stick Resort & Casino so I could afford rent the following month. No safety net if I failed. She nearly had a panic attack just hearing the first part of my story, so I'm glad she's a psychologist trained to deal in this stuff...
  • Stability: In the summer of 2016, my website got hacked and I was facing a very volatile time with my business. At the age of 29, I was faced with a decision to either plant firm roots in Colorado and hustle with local marketing for my services, or to fly across the world to live with my college-aged girlfriend at the time who is studying abroad in Spain.
  • Security: After she turned out to be batshit crazy, I was backpacking through Europe by myself trying to grow my business while working out of hostels with spotty internet connection. I racked up a hefty out-of-country-cell phone bill doing client calls on my phone while walking through the streets. I found myself one night in Northern England with a drunk angry guy I was staying with throw everything I own (backpack, clothes, laptop, passport) in the middle of the street in an angry rage. Middle of November, 10 p.m. at night in the bad part of town.
  • A Safety Net: My two bank cards were frozen when I went to the ATM, and when one of the banks sent me a text message that my account was frozen due to suspicious activity (type YES if you approved of this transaction), my cell phone service cut out.
That last part was my worst fear in life unfolding.

Things most people avoid. Things I don't publicly suggest people do. Some people can handle it and thrive off of uncertainty, and others collapse under pressure. I used to fall into the latter category.

Mixed in with a lot of other crazy shit I've done and similar experiences I've faced on my own personal entrepreneurial, location-independent, risk-taking journey...these were a few of the hi-lights.

I used to be risk-adverse.

But somehow, maybe in some type of unconscious desire I had within myself, for the past 5 years of my life, I threw myself in some of the most uncertain and 'what if...' fear-based situations I could imagine in my life (short of going to a war-torn country).

When her anxiety from hearing my words subsided, she began to lecture my of the stupidity of my decisions and try to reel me into her direction of a more secure and stable life. To the extent that goes against the values of many people in this entrepreneurship community (too safe, too secure)

Immediately, my ego kicked in and I began defending myself: I began verbalizing the benefits that arose from my life experiences compared to hers.
  • I asked her if she has any sales skills. With her psychology work, if the university she works through pulls the rug, would she be able to go out and provide clients and an income for herself? No.
  • If the shit hits the fan like it did for me in the middle of the desert in the casino, or in Europe when all of my resources were pulled away from me; does she have what it takes to survive on her own? Most likely she'd be ok on the support of friends and family. But I value self-sufficiency an the ability to take care of others when I choose to get married/maybe family stuff.
  • But gauging her anxiety coming up just hearing my story, would she have the emotional balance and clarity to not only survive, but to be able to thrive when the shit hits the fan? It'd be tough, just like the first time I put myself through this. This is where most people break, but this is where I feel it's important for self-employed people to thrive.
The direction I was trying to pull her was that TRUE CERTAINTY does not come from the external resources she has saved up, because we live in an uncertain world where we lack that control with jobs and such. And that through all the shit I put myself through (stupidly, unconsciously on my personal growth journey, or by same external force or whatever), I developed a true sense of certainty that I have what it takes to thrive 'in the wilderness by myself' and that I'm emotionally balanced and centered to act with mental clarity through the toughest of times.

For you, you might value something different. But this is something that I've been working on in my life for a while, and through the 'uncertain experiences', that's the only way I found it (not by reading a forum or books somewhere).

By the time my little rant was over, my ego was through the roof, I developed a deeper sense of inner confidence that I've never experienced before in my life, and a true sense of pride in what I'm capable of. I threw out a flirtatious witty comment to her as a result of my boosted ego, "C'mon, you know you'd want to be with a man who knows how to make it in this world when shit goes wrong, whether that's 3, 5, or 10 years from now. Or you could date Jake, the CPA who's never been through some real shit in his life ;)."

She tried to suppress her smile and laughter at the last part; but the look left on her face was the anticipation for her turn to put the boxing gloves on and tear my ego and everything I said to shreds...and I listened to her with an open mind.

To frame this up in the context that we are both in the stage of our life suiting potential long-term partners, and in the relationship frame of this...

Her perception of me as living an overly-risk-taking reckless lifestyle concerned her. That for the long-term relationship she wanted, she wanted a partner with roots planted and stability and responsibility in his life. My actions between the ages of 25 and 30 years old were the complete opposite of that. Just like I preached the benefits of developing character traits through placing myself through unstable situations, she preached her values of the benefits of stability and more risk-adverse behavior in her life.
  • I would never have the character traits I had today if I didn't take the risks. My life would be pretty much the same as it was 5 years ago.
  • But, now that I developed them, did I take my actions too far? Or is it simply time to scale them back to the middle?
While at the beginning of my entrepreneur journey, my values were aligned with her; and in recent years I went in the complete opposite direction to avoid the type of life she has...I feel that after I experienced the other end of the spectrum, it pulled me back into the perfect balance between the two.
  • While I told her that the business owner life (in the short term) is not as stable as hers (I could make $10,000 next week or I could make $0 next week - who knows), it's a path that I'm comfortable with and choose to live.
  • That if I decide to move to a new city on a whim, I've done it a dozen times before, and it's just as natural as going to the grocery story for me.
After only one date together, it is already a common witty phrase she throws at me, "Andrew, let's not pull another Europe fiasco." in regards to whatever lol

At the same time, I notice that in life when we start at one far end of the spectrum (employee craving security) and some of us go to the complete opposite end of the spectrum (chaos with no access to resources in a foreign country), that it's important to find the right balance between the two.
  • To not fear taking risks that most people don't make (developed through being uncertain),
  • But to be calculated with the risks you make in your life (developed through facing the pain of taking uncalculated risks).
It's not something you can really get logically. It's to feel it out through experience.

The reason I write this is two-fold. One one hand, some people here are too far on one end of the spectrum (like the late-20's version of myself) and (in my opinion), she was too far on the other end of the spectrum for the type of life I want to live (not trying to change hers - to each their own).

The main reason for me writing this: Is on the topic of CERTAINTY.

Going back to the SCARF model in the book my business mentor suggested
  • S - Status
  • C - Certainty
  • A - Autonomy
  • R - Relatedness
  • F - Fairness
You feel stress, anxiety, and fear when you do uncertain things. This is equated (in your emotions and behavior to survival). We need certainty in our lives at a biological level, because (unconsciously), it has to do with our very survival. "If you leave the tribal village, you will be in uncertain territory and you will die."

But what I did on my own personal journey was reframe where the certainty comes from.
  • Does the certainty depend on external circumstances and current resources?
  • Or does true certainty come from internal character traits and abilities that you develop when you get comfortable doing things outside of your comfort zone?
While reflecting back on my own personal choices, I went on the spectrum of overly risk-taking and perhaps reckless on many occasions. But it's through those 'uncertain' events where I developed the certainty within myself to provide myself with the confidence that I have the resourcefulness to make things happen in the most uncertain of times.

I'm not telling anybody what decisions to make or to not make, but for a past version of myself who might be in the shoes of many people who are reading this now...

"When you go out there and do those Risk-Taking things that might have felt uncomfortable and uncertain in the past, the very action of doing these new things in your life is actually providing you with the certainty you are looking for as an entrepreneur."

Can you see how uncertainty actually is certainty in this way of viewing things?
  • I am certain that I am gaining the skills to cold call and sell anybody.
  • I am certain that the $500 I lose on this marketing campaign test will provide me with a deeper-level understanding of the market, so I can make up for it int he long run.
  • etc.
The last 3 years of your life went eye in the blink of an eye.

Imagine having this level certainty in yourself and abilities:
  • Your ability to create solutions for the market,
  • Your ability to influence and sell your solutions to complete strangers, and
  • Your ability to do the marketing and advertising needed to reach enough customers to provide you a secure and stable business that you are in control of..
Regardless of if you have any current resources outside of you, that actually doesn't matter.

It's that resourcefulness to operate in any environment and any uncertain time that I now value the most in my life now.

While my reckless days are (mostly) over...and I went over-the-top compared to most, I feel the experiences we gain from these decisions last us a lifetime, and perhaps talking a little bit about navigating through these worst fears and showing where it leads on the other side could be of inspiration to some of you who read this today...

Just don't do what I did.
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Great write-up. Although maybe conflating risk and confidence. True enough, acting without confidence is extremely risky, but solved with education and experience.

For example - all things being equal, your date is better-suited to take advantage of opportunities than someone who chases masterminds. She clearly has a system and real achievements that are leverageable. The space between her and her own business is merely experience whereas the space between a risk-seeking person and success is a complete change in mindset.

I’d argue that while some “rich” people love risk, all wealthy people abhor it. So maybe our definitions of it are different.


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Jul 19, 2017
Solving Pain
This is a suberb write-up.

I can especially relate to the feeling of being judged and seeing as an affirmation to who I am.

The best takeaway was that each cold call or dollar spent on ads. brings one closer to certainty. This is so simple and so profound.

I think deep down, I was most drawn to Fastlane/Unscripted lifestyle because even if world went back to the 1800's level of technology, selling doesn't ever go away. Confidence is not knowing exactly what will happen, only that I will handle whatever it is.

It is really the process of tracing rejection to find success on the edges others are intimidated of facing.

80/20 Takeaway = Each smart risk invests towards future certainty.
Edit: before this, I still perceived smart risk as only a necessary evil. Now I see it as a very positive thing that I have nearly unlimited potential control over taking.
Thanks for this post. Rep added.
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