I’ve been catching up on some memoirs and recently finished Wild by Cheryl Strayed. (I haven’t seen the movie.) I mention it here because the author did a “Big Awesome Thing” in hiking the Pacific Crest Trail and I think achieving financial freedom is also a “Big Awesome Thing”. I thought – What makes a person able to accomplish a “Big Awesome Thing”?

First, instead of rehashing another plot summary for the book, I’ll steal the blurb from Amazon:

At twenty-two, Cheryl Strayed thought she had lost everything. In the wake of her mother’s death, her family scattered and her own marriage was soon destroyed. Four years later, with nothing more to lose, she made the most impulsive decision of her life. With no experience or training, driven only by blind will, she would hike more than a thousand miles of the Pacific Crest Trail from the Mojave Desert through California and Oregon to Washington State—and she would do it alone. Told with suspense and style, sparkling with warmth and humor, Wild powerfully captures the terrors and pleasures of one young woman forging ahead against all odds on a journey that maddened, strengthened, and ultimately healed her.

Cheryl Strayed father also left her when she was young. An excerpt from the book:

The father’s job is to teach his children how to be warriors, to give them the confidence to get on the horse and ride into battle when it’s necessary to do so. If you don’t get that from your father, you have to teach yourself.

In my opinion, the lack of a strong father figure and the early death of her mother left her without the support or belief that she had power over her own life. But by pushing herself to do this seemingly random but difficult task and overcoming many obstacles along the way, she discovered that she did have that power inside. Perhaps each person is drawn to a different “Big Awesome Thing” that can be the first stepping stone to a life lived consciously. Hers was being free in the wild:

It had only to do with how it felt to be in the wild. With what it was like to walk for miles for no reason other than to witness the accumulation of trees and meadows, mountains and deserts, streams and rocks, rivers and grasses, sunrises and sunsets. The experience was powerful and fundamental. It seemed to me that it had always felt like this to be a human in the wild, and as long as the wild existed it would always feel this way.

After that, Strayed could attain happiness and fulfillment because she had the belief that she could change her own circumstances. Her actions mattered. It was worth trying, taking that risk to make your life better. I fear that many others have lost that self-belief and thus don’t even try.

I enjoyed the following excerpt from a poem that was included in the book – “The Summer Day” by Mary Oliver.

Tell me, what is it you plan to do
with your one wild and precious life?

Eric Barker writes at Bakadesuyo.com and his talent/skill is synthesizing hundreds of different sources of academic research and historical anecdotes into actionable ways to improve your life. That’s kind of a crowded field these days, but I enjoyed reading his book which combines a lot of his past work: Barking Up the Wrong Tree: The Surprising Science Behind Why Everything You Know About Success Is (Mostly) Wrong.

If I had to sum up this book in one word, it would be “nuanced”. Be nice but not too nice. Work hard but not too hard, especially on one single area of your life. Grit is good, but time is finite. Thus, quitting and working on a better thing instead can also be good. Is it better to be an extrovert or introvert? It depends. (The book details why.) With so many tips and examples, this was one those books that kept my attention when reading it, but after I finish I had trouble remembering something specific to carry with me.

After looking back on my notes, I decided to make this my takeaway: Be mostly optimistic. For the most part, being optimistic opens you up to more opportunities that more than offset any failures. If I had to use a number, be 80% trusting, 80% optimistic. However, don’t be 100% trusting as that opens you up to abuse. Here are some examples.

Your great weakness may also be your greatest advantage. Consider what makes you unique, and look at it optimistically. You might not make a lucrative career out of your quirks, but it’s still your best shot. You have to align your life and environment to maximize your differences. If you love working within structure, use that. If you need to blaze your own path and can’t stand structure, use that. If you happen to love one thing 1,000x more than anything else, well you better get on that.

Prisoner’s dilemma. This game theory experiment involves two individuals faced with the decision of whether to trust or betray the other person (from Wikipedia):

Two members of a criminal gang are arrested and imprisoned. Each prisoner is in solitary confinement with no means of communicating with the other. The prosecutors lack sufficient evidence to convict the pair on the principal charge. They hope to get both sentenced to a year in prison on a lesser charge. Simultaneously, the prosecutors offer each prisoner a bargain. Each prisoner is given the opportunity either to: betray the other by testifying that the other committed the crime, or to cooperate with the other by remaining silent. The offer is:

If A and B each betray the other, each of them serves 2 years in prison
If A betrays B but B remains silent, A will be set free and B will serve 3 years in prison (and vice versa)
If A and B both remain silent, both of them will only serve 1 year in prison (on the lesser charge)

As one of these prisoners, what would you do? What if you had to do it 20 times in a row? You could always trust. You could always betray. You could do something in between. It turns out that a really simple algorithm does nearly best overall: tit-for-tat. The strategy is simply to cooperate on the first iteration of the game; after that, do what your opponent did on the previous move. If they trust, then you trust. If they betray, then you betray.

You know what is a even a little bit better? Tit-for-tat plus occasional forgiveness. Once in a while, you should trust again even if they betrayed last time. This stops a negative feedback loop of repeated betrayals.

The lessons: Start out nice (be optimistic!) and hope to stay nice, but don’t be a doormat if abused in return. Be consistent. Forgive once in a while.

Optimist vs. Pessimist explanatory style. The book includes an interesting contrast as to how each would react to a setback. Pessimists tell themselves that bad events:

• will last a long time (I’ll never get this done)
• are universal (I can’t trust any of these people)
• are their own fault (I’m terrible at this)

Meanwhile, optimists tell themselves that bad events:

• are temporary (This happens occasionally, tomorrow will be better)
• have a specific cause (It is just because the weather is bad today)
• are not their own fault (I’m good at this, but today wasn’t my lucky day)

It is suggested that you can indeed change your natural optimism/pessimism levels by altering your explanatory style.

This is not to say that you should be only optimistic. Here’s a good post exploring the pros and cons of both sides. The overall conclusion:

The majority of the time, think positive. Happiness and health trump pretty much everything else. There are situations where negativity can help, like when we’re making high-stakes plans or trying to improve skills.

Be optimistic socially. Even if you aren’t a natural extrovert, you can still build your network in a positive way without being sleazy. Meet new people by finding shared interests and/or shared challenges. Help others first when you can, without expecting anything in return. Most people are good and will look to reciprocate. Join groups. Try to maintain contact.

Luck school = try new things. Dr. Richard Wiseman studied “lucky” people and found that the most important characteristic of lucky people is that they are much more likely to just try new stuff, which opens them up to opportunity. In other words, luck wasn’t random; it was due to choices. So he started a “Luck School”, teaching a group of people to act more like lucky people. It worked. Yes, trying more being failing more too, but people tend to regret a failure to act, while the failures didn’t really do any damage. You can often learn from failure, anyway. Finally, we tend to remember the good things and forget the bad. (This selective memory is probably why I have three kids.)

Bottom line. Being mostly optimistic appears to be the best available strategy for many things in life. Try a lot of new things. Meet new people. Optimists are more likely to create opportunities for career success and personal happiness. You will also fail more, but those failures don’t tend to cause permanent damage. Optimism is even associated with better health and longer lifespans. Don’t go overboard. Don’t be a overly-trusting doormat, and don’t be dangerously overconfident. Think 8/10 optimistic. (I’m not naturally this optimistic, so I’ll have to consciously try and change my attitude and explanatory style.)