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Risk Taking

By: Michael Blankenship |

Everything you do in life is a calculated risk. Even a cup of tea could burn you.

– Valerie Taylor

Greetings from LA and Oahu!

This week we’re talking about risk-taking — why risk is an illusion, how successful people see risk, and how to become less risk-averse. This email is a bit different in that we’re only discussing this one topic, but in a bit more depth.  

Let us know what you think!

This week’s email is sponsored by One Sentence News

One Sentence News is a concise, unbiased, stress-free summary of what’s happening in the news each weekday morning. 

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Your Risk Thermostat

We all take risks every day. Even getting out of bed, driving to work, or making yourself coffee are small risks… small enough that we don’t think about them. 

But what if you put $50,000 on the line to try and do something you’ve always wanted to do — say, start a business or move to a new country?

Would you do it? 

Or what if you wanted to do something that would require massive time and energy investments from you for several years before discovering if it would pay off? 

That’s it’s own type of risk: putting sweat and blood into something that could fail.

What’s your gut response? 

Most of us shy away from these types of risk, saving them for “another life.”

We consider them to be noble and desirable — maybe even worthwhile — but we aren’t willing to put our money, time, or ego on the line. 

And yet, the #1 regret of the dying is…

“I wish I’d had the courage to live a life true to myself, not the life others expected of me.”

Our risk thermostat, if you will, is set to a comfortable temperature.

And as Donald Miller writes, “Humans are designed to seek comfort and order, and so if they have comfort and order, they tend to plant themselves, even if their comfort isn’t all that comfortable. And even if they secretly want for something better.”

The Other Side

It’s been said that everything a person wants can be found on the other side of fear. 

There’s a good bit of truth to that. 

If I, for instance, want to pursue my dream of becoming a stand-up comedian, I’ve got to stand on stage and endure post-joke silence. 

Not only endure it… but embrace it as a part of the journey. 

I’ve got to get to a point where it doesn’t bother me so much that I turn tail and run. 

I’ve got to hold my ground in the discomfort. 

This is true of all worthwhile pursuits — building a business, investing, writing a book, raising children, so on and so forth. 

The things you want can only be claimed after conquering the mountain upon which those things sit atop. 

And yet, taking that first step is often so difficult. 

Instead of looking at the peak, we look at the path ahead. We see the bramble. We see the steep hills. We see the sharp rocks. 

We turn away and settle for a path that’s less daunting… but also less rewarding. 

Meanwhile, those who are willing to take the more difficult path either reap the rewards upon reaching the peak, or they stumble along the way and learn a valuable lesson they wouldn’t have learned otherwise. 

Even their failure becomes an asset to their future success. 

They come to understand, as Ryan Holiday, put it, “The obstacle in the path becomes the path. Never forget, within every obstacle is an opportunity to improve our condition.”

Where is the risk, then, that we were so afraid of? 

It’s not in the failure. That’s only a lesson. 

It’s not in the pain. That only makes us more resilient. 

It’s not in the loss. That only makes us less dependent. 

And thus with proper thinking, risk is only an illusion. There is no real risk for the person who is willing to learn and grow from all experiences, only forward momentum and life’s wild adventure. 

The Risk-Taking Mindset

That gives you an idea of the mindset behind risk-taking. 

But let’s go straight to the source. We asked some of our most successful friends how they deal with the risks involved (both financial and time-and-energy investments) in their pursuits. Here’s what they said…

Because investing massive amounts of my time and energy into other peoples pursuits is just as likely to fail. And because I value freedom over stability. – Bill Widmer, founder of The Wandering RV

I believe there is no failure, only feedback. My biggest lessons come from my biggest failures in life. Even a failed experience can teach me ten times more than taking no action at all. “Fail fast, fail forward” – That’s my motto in life and business. – Dr. Ai, founder of Classroom Without Walls

Honestly I get off on risk. I fly paramotors, drive race cars, rock climb, and run businesses. I enjoy the flow state that risk creates of requiring 100% of my focus. I feel most relaxed at 130mph, under a paraglider, or with tens of thousands on the line. This is my favorite quotes as of late: “Life should not be a journey to the grave with the intention of arriving safely in a pretty and well preserved body, but rather to skid in broadside in a cloud of smoke, thoroughly used up, totally worn out, and loudly proclaiming ‘Wow! What a Ride!’” – Ryan Dossey, serial entrepreneur & real estate investor

Because my life mission is to eliminate despair, and the only way to do that is through building businesses of impact that then feed back currency in exchange for elimination of despair. Be it through the companies itself and currency being client success or financial currency — both become synonymous. If there was 0 possibly of failure then there would be 0 possibly of success. Failure is fine, it’s expected and welcomed. My emotional currency is paid through the impact my companies make on others, I’m willing to pay back that currency through failures — and I focus on reducing personal impact of failure through financial intelligence. – Tyler Austin, founder of REISift

In other words, the “risks” are worth it for the lessons, rewards, and adventure that’s on the other side.

Turn Up The Heat!

Bigger, calculated, meaningful risks stand in the way of the things we want. 

In order to be more willing to take those risks, we need to raise the level of risk that we’re comfortable with. 

How? 

Well… by taking bigger and bigger (always meaningful and calculated) risks!

The more risks we take, the better we’ll get at risk-taking. 

Here are seven ways, from Fast Company, to “cure yourself of risk aversion”, annotated. 

  1. Start with small bets — Find risks that are just outside of your comfort zone and start there. 
  2. Let yourself imagine the worst-case scenario — What’s the worst thing that could happen? Actually answer that question and you’ll discover it’s not as scary as it seems. 
  3. Develop a portfolio of options — Don’t pull all your eggs in one basket. Spread your risk across a few different pursuits to increase your likelihood of success. 
  4. Have courage to not know — Don’t be afraid of the unknown. Embrace it as evidence that you’re learning and growing. 
  5. Don’t confuse taking a risk with gambling — There’s a big difference between putting money in a slot machine and taking calculated and meaningful risks. Take risks that mean something to you and are worthwhile. 
  6. Take your eyes off of the prize — Don’t just focus on the mountaintop. Look at the journey and learn to enjoy it. Think about all of the things you’re going to learn along the way. 
  7. Be comfortable with good enough — Nothing needs to be perfect. Just do the best you can in the season you’re in and keep moving forward. 

Extra Stuff

Here is some other random stuff we found interesting this last week!

Books We’re Reading

Here’s what the tribe is currently reading (let us know books you’re loving and we’ll include them in future emails!)…. 

  • Do Hard Things by Steve Magness“Steve Magness, a performance scientist who coaches Olympic athletes, rebuilds our broken model of resilience with one grounded in the latest science and psychology. In Do Hard Things, Magness teaches us how we can work with our body – how experiencing discomfort, leaning in, paying attention, and creating space to take thoughtful action can be the true indications of cultivating inner strength. He offers four core pillars to cultivate such resilience.”
  • Super Coach by Michael Neill“In this fun, easy-to-read book, best-selling author and internationally renowned success coach Michael Neill shares the secrets of transforming your life and the lives of the people you care about most—your family, friends, colleagues, and clients.”

This Week’s Image

“A train moves through shallow water near a salt-harvesting site in Burlinskoye salt lake in Russia’s Altai Region, on July 20, 2022.” via The Atlantic

This Week’s Riddle

Here’s this week’s riddle — the answer is at the bottom of the email!

Dead on the field lie ten soldiers in white, felled by three eyes, black as night. What happened?

This Week’s Journaling Prompt

Take some time to think through the following journaling prompt. 

To you, what’s a risk worth taking that you haven’t taken yet? 

This Week’s Challenge

Take a meaningful risk! This could mean doing something that will require time or financial investment on your part. Maybe it just means setting aside time to do something you’ve been wanting to do. Or maybe it means paying to get started. Either way, accept life as an adventure and give yourself permission to take a little bit of risk. 

Until next week, 

Mike & Alec

Riddle Answer: A bowling ball knocked down ten pins.

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