Chapter 3 – “Quit: You Make a Decision to Cross the Threshold”

In Chapter 3 of the podcast, J. Thorn challenges traditional principles of decision-making and underscores the importance of embracing change, despite its inherent difficulty. The episode posits that the quality of a decision cannot be judged solely based on its outcome, and decision-making becomes more challenging as one ages due to increased risk aversion. The stress associated with decision-making often stems from the anticipation of the decision, rather than the act of deciding itself. J. shares how he found guidance from entrepreneur and author Chris Brogan during a pivotal moment in his life.

Everything you know about decision making is wrong, but it’s not your fault because we were all taught those principles on faulty assumptions. Most of the variables are out of your control, including the element of luck. Because of that, you can’t base the quality of your decision on the outcome. This doesn’t seem rational at first glance, but it’s absolutely true.

For example, let’s say you order the shrimp fajitas from your favorite Mexican restaurant. You’ve ordered them dozens of times in the past and they’re your favorite dish. You decide to order them tonight, and then the next morning you wake up sick because unbeknownst to you, the shrimp was bad and gave you food poisoning. Did you make a poor decision? No. Even though the outcome was terrible, you made the best decision possible with the information you had at the time. Judging the quality of a decision based on the outcome is called “resulting,” and it’s a concept Annie Duke popularized in her book, “Thinking in Bets.”

“Crossing the Threshold” is the act of making a change, one that will have a profound impact on your life. Because of that, it’s always an important decision, but never an easy one.

As you age, decision-making becomes more difficult because you naturally get more risk-averse. Therefore, you end up staying in that bad relationship, terrible job, or money pit of a house simply because you dread the idea of making a decision, not necessarily the consequences. In fact, a strange thing occurs once you make a decision—you’re more at peace with it, regardless of the outcome. The stress comes from anticipating the decision, not the act of deciding.

A few helpful words

I was at a critical moment in my life, although I didn’t realize it at the time. I’d found a friend, mentor, and like-minded soul in entrepreneur, podcaster, and New York Times bestselling author, Chris Brogan. Although I wasn’t recording our conversation, I can still hear his words with clarity.

As I was trying to decide whether I should take a job with a small agency, Chris asked me a question that put me on my heels. He said, “Why would you want to wear someone else’s jersey on your back?” If you can’t tell, this was a sports metaphor. What Chris was really asking me was why would I join someone else’s editing agency instead of starting my own? He proceeded to tell me that I was capable, hard-working, and that I didn’t need anyone to make it on my own.

With a simple question, Chris cut to the core of my problem—a lack of self-confidence, and more specifically, my inability to be decisive about this issue. I had unknowingly become risk-averse and was ready to accept the easy path.

In much the same way that Gandalf guided Frodo but did not retrieve the ring for him, Chris didn’t do the work for me. He didn’t hire me or use his platform to get me clients. Instead, he mentored me by asking a hard question, and I’ll always be grateful to him for that.

As you’ll see, it’s not easy making decisions. I don’t want to make it sound like it is. But with a little guidance from those ahead of you on the path and with a plan for quitting before you begin, you can definitely make good decisions without regret. What I came to realize is that the worst-case scenario is never as bad as you think it is.

Writers, Ink // Episode 2 // April 20, 2020

This clip is from the “Writers, Ink” podcast, episode 2, first published on April 20, 2020.

I approached (er, pitched) J.D. Barker at Thrillerfest in 2019, and asked him if he wanted to start a writing podcast with me. J.D. immediately and enthusiastically said… no.

But I wore him down and we eventually started, “Writers, Ink.” For the first 150 episodes, I interviewed some of the biggest names in publishing, including Dean Koontz, James Patterson, Joyce Carol Oates, Gillian Flynn, and Seth Godin, to name a few.

Although I have since left the podcast for new challenges, J.D. and I remain friends and keep in touch regularly.

In this episode, I interview the author of “The War of Art,” Steven Pressfield and “Story Grid” editor, Shawn Coyne.

Pressfield talks about a passage in “Tides of War” where Athenian statesman, orator, and general Alcibiades says, “Fortune favors the bold.” Steven goes on to explain why the gods look with favor upon the risk-takers.

Both Steven and Shawn explain when Resistance is at its strongest and the ways in which it will attempt to confuse you.

And Shawn shares that he has a 50% success rate on projects, and commends me on my hard work escaping my golden handcuffs.

You’ll discover how to choose what to work on next. Steven Pressfield believes you should pick your craziest ideas because the Muse isn’t rational. All of your decisions are emotional, even though you believe they’re logical. But that doesn’t mean making decisions is easy.

Transcript:

J.: How do you determine if an idea is crazy? And then, what if you have 15 crazy ideas? Sort of, what’s your thought process behind that approach?

Steven: It’s actually – I was just writing another post like two minutes ago. This whole concept goes very deep. When I say “craziest,” what I sort of mean is not obviously commercial, right? Not something that you think you’re trying to second guess the market, right? But also “craziest” in a sense of something that doesn’t necessarily feel like it’s really “you,” quote-unquote “you.” It’s like, “Wow, why should I write that book, you know, a book about Queen Bowdika?”

The whole idea behind that is that the muse, or whatever that second level of unconscious thing is, doesn’t operate by the same rules that rationality does. She has her own agenda for us. So when we pick something that seems quote-unquote “crazy” to us, we may really be picking the absolute right thing to do.

I sort of go back to the blog posts I mentioned, my own books, “A Legend of Bagger Vance,” and “Gates of Fire,” my first two books. If you think about those ideas from the jump, you know, you’re sitting there and you’re thinking, “Why don’t I write on mystical golf?” or “A story about a battle that nobody’s ever heard of from 2500 years ago?”

To me, those ideas sounded completely nutty, particularly since I really didn’t know about either of them. But they worked. So, for me, I kind of say, “Well, maybe I’m not so smart after all.” And that’s sort of the whole concept.

Want me to go a little bit deeper, James, if you’re okay with that?

J.: Sure!

Steven: Shawn—this goes back to “Tides of War.”

Shawn: Yes.

Steven: There was a real-life character, James, in the ancient world called Alcibiades, who was an Athenian general. He was sort of a predecessor of Alexander the Great, but a doomed predecessor, cut from the same mold.

Both of them kind of operated under the philosophy of, “Fortune favors the bold,” particularly Alexander. He used to, on his great horse Bucephalus, lead the charge into the enemy lines ahead of everyone in the army with a double-plumed helmet so that everybody could see who he was. So that every arrow and lance from the enemy was coming right at him.

But he was doing that because he believed that fortune favors the bold, and that by taking such an action, the gods would follow him. And of course, in the real world, his army would follow him. They saw their king going in, and they thought, “Well, I can’t stand around, I’ll charge right after him.”

J.: If a writer is in a position where they have a bucket full of crazy ideas but it’s taking a long time, however that person might define it, to make a decision on which one to charge into the battle with, could that extrapolated process be a form of resistance?

Steven: Oh, definitely. For sure. Absolutely. And that resistance will go away the instant they pick a project.

J.: So, making that decision, even if you’re not 100% confident that it’s the “craziest,” is still better than not making the decision at all?

Steven: Yeah, I think so. But resistance will also try to confuse you and go, “Oh, well, maybe this one’s really the craziest. Or this one’s really the craziest.”

And I think then you just have to sort of trust your instincts and make a decision. Those other voices in your head that are saying, “Oh, maybe number B is the craziest or maybe number 2 is,” those are pure resistance. It’s resistance trying to f*ck you up.

J.: Yep. Excellent. [to Shawn] Do you look back at your own track record and say, “Previously I picked this crazy f*cking idea and it paid off, or it didn’t pay off. Does that influence your future decisions?”

Shawn: Well, the beauty of it is, you know you’re crazy and an artist when all those shitty decisions you made before completely vanish in your head.

Yeah, I mean, I would say I’m probably batting 50/50. 50% of the things I take on reach their conclusion point. I don’t mean that they’re commercially successful, but they reach their conclusion point. And then it’s up to the gods whether or not they work. The other 50% don’t.

The relationship is destroyed with the people I’ve worked with before because we’ve ripped each other’s throats out trying to make something come to life. But when you know, you just know.

It’s like, what compelled you, James, to leave your profession to start a brand-new business and profession? You just deep down knew, “Ah shit. I know I have to do this.”

J.: Yeah, there’s no rational reason for it.

Shawn: You just kind of said, “Well, I’m just gonna do it. And whatever shakes out is going to shake out.” That’s a really difficult thing to come to terms with. But once you do, it’s just hard work. You know, it’s just grinding your ass in the dirt.

The Writer’s Well // Episode 37 // September 13, 2017

This clip is from “The Writer’s Well” podcast episode 37, first published on September 13, 2017.

Rachael Herron is truly my gay sister from another mother. Even before I asked her to podcast with me, I adored her eternally positive and warm approach. Since she’s moved to New Zealand I miss her dearly, and I pine for the podcast we recorded together, especially around the time we left our day jobs to become full-time authors. There are few people in the world—not just the publishing industry—who I respect more than Rachael.

In this episode, we try to answer the question, “How does your age affect your outlook and/or decision-making?”

Rachael shares a story from college, a time when a professor told her, “You haven’t lived enough yet.” Although this upset Rachael at the time, she came to draw comfort from her vast life experience with the understanding that you never stop learning.

We both talk about the ways in which our huge risks have paid off and for the ones that haven’t, those failures have made us more comfortable taking risks.

You’ll discover how you get better at making decisions by making decisions—that you’re always learning, and the older you get, the wiser you get. Even though it is frightening, huge risks pay off. The worst-case scenario is never the worst case.

Transcript:

J.: How do you think your age affects your outlook and or decision making?

Rachael: Oh, that is a large… my outlook and or decision making.

J.: And this could be – I mean, this could be really related to your author business or your sort of general risk-averse risk-taking behavior. Like, I mean, just, in general, like, you know, another way to phrase it, too, would be like, “Would you give different advice now than you would have 10 years ago?” Or do you like – if someone asked you for advice, knowing them and where they are, does that influence what advice you give them?

Rachael: Yeah, and the first thing that I land on in my head is I had a professor in college. I was probably about 22 or so because I took forever to get through college. But I remember him telling me that he thought I was a really good writer, and that I had a lot of talent, and that he didn’t think I had lived enough yet.

And, and I just remember being so offended. “You know, you don’t know my, my being in his brain. I know so much about life.” And of course, I didn’t really know anything about life. And that’s the funny thing and he was completely right.

But there is this, there is this comfort that I take in being 45. And having gotten to the place, I am kind of the hard way. And I do have that life experience, and I have enough life experience to know that I am quite smart right now. And I don’t know half of what I’ll know, when I’m 65. You know what I mean?

Now that I know that you can learn so much in just, you know, sometimes just a few weeks, you can learn more than you’ve learned in the last 20 years put together, depending on circumstances. That’s a comfort to me.

So can you repeat the question again? One more time? There were two parts at the end?

J.: Yeah, your outlook or your decision making?

Rachael: Oh, decision making. Yeah, I wanted to touch that because I have always been a risk taker. And I don’t know if it has something to do with my ADHD. ADHD people are higher risk takers, more impulsive. So I have that impulsivity thing.

But being 45, I have learned that most of those huge risks that I take, pay off. And I am so much more comfortable. I’m more comfortable risking. And I’m also much more comfortable failing. Because when you risk you do fail, and I heard something I was listening to Joanna’s show the other day, and there was a woman on it. And she was really, she was really cool. And she was talking about how she dreamed about writing – it was her one big dream. And this seems like such an obvious thing to say, but I’d never thought of it just this way. She said that the reason she didn’t do it was because if she failed, that was the thing that was most important to her.

So if she tried it and she failed, then she would have failed to basically her whole life.

J.: And then it’s kind of like a, “Then what?” situation.

Rachael: Exactly, exactly. And I love that and that that rang really, really true for me. And I think that that is what prevented me from being serious about writing for so long. But when I did – when I did jump and take it seriously, the world changed and – and you know and I’m talking about like you know 12, 13 years ago when I decided to go full bore really hard on the writing thing.

But the risk taking in terms of my age is in everything – it’s in car buying, it’s in house buying, it’s in the decision to get married kind of thing. I make big decisions quickly and now I know that usually I’m kind of right and if I’m not right, it’s gonna be okay. Anyway.

J.: Do you think that’s a function of seeing that happen for years and years and years?

Rachael: I think it – I really think it is because I used to be – I was always a risk taker but I was always a lot more scared too. I spent a lot of time in anxiety about basically everything – like the wind would change and I would get anxious about it and that has calmed down a little bit as I just, I just kind of keep surviving, you know, and not even surviving but flourishing.

I know that – this is gonna sound so hippy, but like, you know, I know that my roots are strong enough and that if somebody yanks me out of the pot and sticks me into more dirt, I can establish roots there too, right? I know that – or if I put myself in a different pot. And I’ve learned that and I’m confident in that.

I’m also – I think I get a little bit more scared as I get older though too. Just that, I am very, very conscious of my body now and how it works and thinking about what I put into it and I, you know, at 25, all I ate was Cocoa Puffs, you know, for – for chocolate cocoa puffs and like grilled cheese sandwiches. Can you imagine?

So, I am really a lot more careful. I’m careful with the Yoga I do. I don’t want to do things that I could break a hand or a wrist or, you know, anything like that. I’m careful that way. So, I think that might also be a function of age – the other opposite kind of function.

The Writer’s Well // Episode 84 // August 15, 2018

This clip is also from “The Writer’s Well” podcast, episode 84, first published on August 15, 2018. In it, Rachael and I try to answer the question, “How do you know when to let go?”

We go deep, talking about how and when to let go of something that isn’t working. The conversation explores the difference between “working” on something versus “forcing” it. Both of us acknowledge the power of the sunk cost fallacy and our internal programming that drives us to always finish what we’ve started.

Although I talk about how I’ve gotten more comfortable failing, it still sucks. Until you cross the threshold and take a risk, you’ll never know how it feels when it pays off.

You’ll discover when it’s time to quit, and when you should keep going. Annie Duke often writes about making decisions, and more importantly, how to judge the quality of those decisions. We’re biased to see things through to the end. “Quitters never win,” and all that. But sometimes quitting is exactly what you need to do before you can start something new.

Transcript:

Rachael: What about you? I’m interested. I’m wondering if I went too philosophical for you.

J.: No, didn’t.

Rachael: You know, not practical enough?

J.: No. But you went in a different direction, which is very pleasant and surprising.

Rachael: Oh, good! And I want to hear what you say.

J.: I’m, I’m terrible at not sensing when I have to stop investing in something, or someone. Yeah. So, I was looking at letting go. Maybe I was being more philosophical about it, thinking about like, okay, there’s still responsibilities, or there’s still things that I have to do, but emotionally, how do I let go of something that isn’t working, or causing me pain or causing somebody else pain, and I’m not being a podcast tease, but there will be things I’ll talk about in a few months from now, later, maybe next year that I can specifically refer to.

But one of my problems and it’s good that I have Zach as a partner because Zach is really a really good sounding board for me. And he notices this and he brings it to my attention. I don’t always listen to him, but I need to start listening to him more often.

But it’s like, I get into a project. And I am so headstrong, and I am so determined to make it fucking work that I force stuff. And, and I, when I cross the line from sort of working on it to forcing it, I’m not aware of that.

And, and there are certain projects and certain things and certain people that I know, I just need to let go. And letting go could just mean like, we’ll finish what you committed to, but stop investing all the emotional calories into it.

Rachael: Does it come down to worry about kind of that sunk cost fallacy that you’ve already spent so much time and emotion and money into a project, it’s very hard to let that go?

J.: That’s a huge part of it. Yeah, that’s a huge part, I feel like, once I get into a certain point, I can’t, I can’t back out because I’m so invested in it. That’s one part of it.

Another part of it is I have this, maybe it’s an Aries, I’m an Aries. Or maybe it’s my firstborn, or my family upbringing, but I have this, like, you finish what you start. Loyalty is not the right word because that sort of implies this loyalty to somebody. I have this loyalty to the finish. Like if I say, I’m going to do something, I’m going to fucking do it. And even if it kills me, like, I’m gonna get it done.

And, and I think the word done like, that’s where I’m starting, I think, to learn a little bit, and hopefully gonna get better at that. Because you can still be done without investing your entire soul into it knowing that like, it’s just not working. Like, it’s, you just gotta let it go. Like, you’ve got to emotionally detach, but still fulfill your responsibilities. And that’s so hard, because I think a lot of people like me, just charge through and they’re, like, determined they’re gonna do it. And other people just walk away completely, like, drop the mic. You know what I mean?

And like, neither of those are good.

Rachael: Exactly. For does it relate in your head or body or whatever, for me, for me, that kind of charging through and the determination to finish what I started, no matter what it was, comes to this weird, stubborn pride that I have. If I at one point decided that it was something I wanted to do. That means that I decided I would do it and succeed at it.

And I’m so stubborn, and I and I want to fulfill all these things that it’s, I mean, you and I talk a lot about our comfort with failing. Which is very true. I am pretty comfortable with failing now. But that’s only because I had to, I think you and I have both had to let go of a lot of things and, and hit our head against that wall and realize, oh, sometimes we just… Even every year, I feel like I’m learning more and getting better at this job. And every year I still try to do things that I can’t do or that I shouldn’t have done. And that pride of admitting that like I was just wrong about that hurts.

J.: Yeah, there’s definitely a pride element there. There’s an interpersonal piece in that I hate letting people down. And it’s so important to me to fulfill my commitments, and if I tell someone, I’m going to do something, including myself, then I’m going to damn well do it.

And sometimes it’s just not the right approach. And I think your point to like, I don’t regret this because I’m this is what causes me to fail a lot. And when I fail a lot, that’s where I learn. And, and even if one out of 20 of those failures turns into something cool, it’s super fucking cool.

But it’s also good to remember and remind ourselves that just because we grow, it doesn’t mean it’s easy. Like failing still sucks. It still hurts.

Rachael: We like to talk about failure, and we laugh about it. But it’s not fun.

J.: It’s not pleasant at all.

Rachael: It’s always funny later. But in the moment, you’re, you’re looking at yourself as a failure. And those are the moments at which I literally always want to, and sometimes do, just go get in bed and pull the covers over my head, and, you know, read a book and fall asleep.

My go-to absence of mind right now is, you know, sleep. That’s because I don’t have any of the other coping tools I used to have. So I know that when I’m trying to sleep more, I need to be looking at like, what are you feeling ashamed of failing at right now? And it’s usually something.

But like you, I would, I would much rather. But myself, I don’t know if you said this. So I don’t know if you said this, but for me, I would much rather let myself down than anyone else. I will go to extreme lengths not to let down a guy I’ve never met who was in northern London, who asked me for a favor. I would, I would do anything for him. And sometimes, you know, that’s just that’s absolutely wrong.

That’s a really good difficult question. How do you know when to let go? And so it’s so big, like it can it can be in terms of you know, partnerships, and friendships and business decisions and, minute little tiny projects that you might be doing, you know, might you might take 15 minutes this afternoon to do it? Or should you let that go?

J.: Even as far as, like you, could you could you talk about people, maybe you have a friend or even a relative, who you know, is not good for you, and it’s letting go can just mean emotionally detaching, it doesn’t mean you quit talking to them.

Rachael: It doesn’t mean you have to divorce them and say, we are no longer friends, we are done. We’re cutting off the family.

J.: Yeah, letting go is not a binary decision. Like you can, you can still sort of pull back and, and have a surface relationship or be cordial or polite, but not invest emotionally so much. And that’s, that’s the gray area that I just have to continue to work on to learn. And because so many times I just don’t see it myself. And, and I easily cross the threshold from working hard to, you know, just fruitless labor and, you know, hitting walla.

Rachael: Exactly. And speaking of speaking of people, just real quickly, something that I’ve realized lately, and it’s a very good litmus test for myself, because I’m that ambivert, I’m a really I’m mostly introverted, but I do excel in extraversion sometimes.

But when I’m choosing to be around people lately, I’m only choosing to spend my time because I get to do this because I run my own business. But I’m only spending time around people from whom when I leave, I feel energized. And you can be around equally delightful people. But when you leave them you just feel like your energy was sucked in so that’s the energy vampire.

I prefer to be in the presence of somebody where the energy is flowing back and forth. And we both leave feeling great about being with each other. And I’ve let go of a bunch of people who don’t make me feel like that. And that’s okay.

J.: Yeah. It is okay.

Closing Thoughts

I won’t lie to you because I’m terrible at it. Making decisions is difficult. You have to surrender to things beyond your control. Even a simple decision, like choosing shrimp fajitas over a chicken burrito, can have unintended consequences.

The conversations you’ve just heard came at critical moments in my life, although I only know that in hindsight. At the time, each decision felt life-changing with high stakes. They were, and they weren’t at the same time. As I’ve said to my children often, if you don’t like the outcome of a decision you’ve made, just make another.

In 2017, I made the decision to cross the threshold. I left my ordinary world for what would become my extraordinary world. As you’ll see, it wasn’t all rainbows and roses. But looking back now, I have no regrets because I made the best decision I could with the information I had, and I didn’t concern myself with things out of my control.

With a little help from a mentor and an awareness about your tendency to avoid making decisions, you can design the life you want. You’ve seen that it’s never easy to make decisions, and no matter how rational you think you are, you often decide with your emotions.

Question

How do you make decisions? What would you have to surrender that is beyond your control?

Up next…

In the next chapter of the story, we’ll encounter some tests, obstacles, and setbacks that are all a normal part of change, including a decision to max out the credit card and go all-in on a new career. This is the biggest Point of No Return in my life so far.

Credits

Mentorship by Brian Clark, Jerod Morris, and Trudi Roth

Podcast concept by Jerod Morris

Written, narrated, and produced by J. Thorn

Editing by Miranda Weingartner and Trudi Roth

Audio editing and production by J. Thorn

“Twisted” and “RetroFuture” courtesy of Kevin MacLeod at incompetech.com

Licensed under Creative Commons: By Attribution 3.0 at creativecommons.org