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This episode integrates the Plumb as a practical decision test, using the “nice guy finishes last” pattern as a concrete example. The focus is on how unstated objectives and misaligned behavior pull people out of plumb, and how explicitly naming what you want restores grounding, agency, and honesty.
🔑 Key Takeaways
- Many pro-social behaviors are driven by unstated objectives.
- “Nice guy” behavior often trades clarity for implied social pressure.
- Misalignment occurs when behavior is not visibly connected to a stated goal.
- Naming what you want removes resentment and martyrdom.
- The Plumb can be used in real time to test whether behavior can actually produce the desired outcome.
💬 Featured Quotes
- “Nice guys finishing last is a plumb problem.” (1:06–1:13)
- “It is a misapplication of behaviors to achieve an unstated outcome.” (1:13–1:18)
- “They are trying to do the right thing in order to achieve an outcome.” (1:26–1:39)
- “There is a disconnect somewhere in the line.” (1:39–1:47)
- “The unstated expectation… that I was going to exchange this behavior for some form of social capital.” (2:18–2:37)
- “That unstated objective is the core of the nice guy problem.” (2:41–2:46)
- “That’s not plumb behavior and it’s not building plumb relationships.” (3:42–3:46)
- “First things first, state what you want.” (4:15–4:21)
- “That’s going to solve 99% of your problems.” (4:21–4:29)
- “Stop trying to expect the world… to become a mind reader.” (5:23–5:29)
- “Figure out what it is you want.” (5:53–5:55)
- “Is the behavior I’m undertaking able to create that outcome?” (6:10–6:14)
- “If the answer is no, you’re operating out of plumb.” (6:14–6:19)
- Tim Dedman
- Jorge
Creators and Guests
What is A Mason's Work?
In this show we discuss the practical applications of masonic symbolism and how the working tools can be used to better yourself, your family, your lodge, and your community. We help good freemasons become better men through honest self development. We talk quite a bit about mental health and men's issues related to emotional and intellectual growth as well.
So I was working with the plum in reflection the other day and I learned and learned something
really productive.
You've probably heard like I have the statement or the sentiment that nice guys finish last.
And if you've ever experienced nice guys finishing last for yourself, there is a lot of positive
emotions that come from this.
I know it sounds crazy right because you finished last, you didn't get what you wanted.
But the martyrdom that comes with being the nice guy, the self-righteousness that comes
with it, all of the kind of sort of self-soothing indignants that comes with being the nice guy
that finishes last is
a big part of the objective of being that nice guy.
Another part of that conversation that's really important to understand is then the nice guy
finishing last is a plum problem.
And it's a plum problem because it is a misapplication of behaviors to achieve an unstated
outcome.
Though let me be clear, when we talk about somebody who's a nice guy and they are trying
to do the right thing, more often than not, they are trying to do the right thing in order
to achieve an outcome.
There is a disconnect somewhere in the line and instead of being upfront, they are creating
an implied social pressure to deliver on a result.
So you'll see it a lot in the dating sphere.
It's where a lot of toxic sort of men hang out.
They will create, they'll do the nice thing, whatever that is.
I loaned you money to a picture car, I X or Y or Z.
Examples about with the expectation, the unstated to be clear and this is where the nice
guy problem starts.
The unstated expectation that it was going to turn into something else, that I was going
to exchange this behavior for some form of social capital, which I was then going to leverage
to get one of my needs met, whatever those needs might be.
And that unstated objective is the core of the nice guy problem.
It's that the behavior is not aligned to not visibly and obviously aligned to the plum.
It's like, well, why are you doing this?
Why are you doing this nice guy stuff?
I don't know because someone told me to because somebody sold me along the line this idea
that if I did these nice pro social things, then my outcome would happen automatically.
And if you've watched any of the Sunday morning cartoons growing up, the back when Sunday
morning cartoons or Saturday morning cartoons were a thing, that was clearly communicated.
In almost every show, go do the right thing and the outcome you're looking for will happen.
But it was just like a big question mark in the middle.
Well, how is that going to happen?
Don't worry, it'll work itself out.
That's not plum behavior and it's not building plum relationships.
It's not building relationships based on mutual respect, all that kind of stuff.
This nice guy finishes last sort of sentiment is essentially that question mark.
Like I did all of the nice things, but I didn't get what I was looking for.
First things first, you were fine yourself saying this to yourself in a regular conversation
internally.
When you say, man, I did all the right things that I didn't get what I want.
First things first, state what you want.
State what you want.
That's going to solve 99% of your problems and you will not feel put upon if you want
a date, ask for a date.
If you want money, make it clear that you're going to do some things for money, whatever
they might be.
Don't let the unstated question mark of what your objectives are.
Lead you down this path where this pro-social behavior that you're trying to do essentially
becomes this badger suffering that you wear so that you can get that social approval
from your friends because I did all the right things.
Look how unfair the world is.
Look how put upon I am.
When in fact, the answer was, stop trying to expect the world, whatever that might be,
to become a mind reader, to give you what you think you want without you having to do
the work, the discomfort, the other things that come with trying to get that outcome.
You'll find that the whole conversation shifts and just try this across the board when you're
out and about and you're trying to figure out why things aren't going your way.
Start by defining what your way is.
What is it that you want?
I know.
It sounds crazy.
Figure out what it is you want.
Write it down.
Write it down on paper.
And put it in a text message to yourself.
This is what I want.
And the moment you write that down, you'll grab your plum and say, is the behavior I'm
undertaking able to create that outcome?
If the answer is no, you're operating out of plum.
See you next week.