Episode 65: Beware of Labels
September 11, 2025
The classifications we accept can shape more than we realize.
Labels are tempting because they simplify, but they rarely capture the full picture. Once we accept a description of who we are, it can quietly shape our choices and limit what we attempt. A label repeated often enough can become a story that feels fixed, even when it is not. This episode considers the risk of letting those shortcuts define us, and why leaving space for change may open the door to new abilities, interests, and opportunities.
Transcript
I've never 100% figured this out, but I've always considered myself either an optimistic pessimist or a pessimistic optimist.
Optimism and pessimism being, you know, the glass half full, half empty kind of thing.
Do you generally look at the world through a more negative and deficit lens, or do you generally look at the world through a more positive and, well, optimistic lens?
I've never really fit into either of these camps, not all that cleanly.
I think about this in terms of how I go about not just viewing the world, but in particular, problem solving and working through challenges.
There are people I've met through life who I've always envied, and maybe the fact that I envy them gives the whole thing away.
But, you know, people who just radiate positivity.
I'm sure you've met people like this in your life.
Maybe you are one of these people.
I have a great deal of envy for this, where just no matter what comes someone's way, it's just good and positive.
And not that it is good and positive, but that their outlook on it all is just wonderful.
And then there are people I've met through my life who are definitely in the pessimistic camp.
And these are people that I do not envy.
And the biggest trademark that I think I've seen about these, you know, folks who very much squarely fit into the pessimism camp, it's almost like they have chronically bad luck.
But they don't, right?
It's that they make their own – people make their own luck.
I'm a big believer in that.
And whatever comes their way, it has – it inherently ends up with a negative spin because they see the worst in it and then lean into that, right?
And I'm sure there have been times in my life that I have fit – it's like anything else, right?
You're not the same person always day to day.
And so on – I'm sure there have been times and occasions where I have been a very blatant optimist and times and occasions I've been a very blatant pessimist.
But generally speaking, I tend to find that I'm a blend of the two and in a very specific way.
When challenges are brought to me – and this is very, very clear in professional settings, but I – personally, I do the same thing, really.
When a challenge is put in front of me or a – we won't even talk about a challenge, an opportunity, anything, right?
Let's say someone you're working with comes to you and says, hey, I really want to do this thing.
I really want to push forward this initiative.
The way my brain works is that I find all the problems with it that I can, just inherently.
That's where my brain goes.
All of the problems that whatever this thing is, all the challenges and issues and roadblocks and everything I can think of that would stand in the way of this thing.
But I've come up with all of those things in service of how do we – how can we tackle all of these things in order to push the thing forward, right?
So, at the end goal is an optimistic goal.
It's that I want to make this thing work.
But the way I get there is by pessimistically identifying everything that can go wrong with it.
And that's where I've always operated this way.
And it's where I do see a difference because having worked in an organization – you know, I worked in an organization for 15 years.
And there was so many meetings where someone would throw an idea out and then I would watch the other people in the room find everything wrong with it, right?
Much like I was just describing about myself.
But they would stop there.
And the purpose of finding – poking all these holes was not in service of pushing it forward but in service of shooting it down.
And that's not me, right?
I'm the other side where I find all those holes in it because that's how my brain operates.
It just finds all the problems.
But it's usually in service of how do we tackle those issues to get to the end goal.
How do we push your thing forward understanding all of these problems?
And there's a very big difference.
And, you know, if any of this sounds familiar to you, I'm sure you've been in those meetings.
There might have even been times when you were those people, that person in those meetings, where someone comes up with an idea and rather than trying to lift that up – see, the pure optimist would just lift that idea up.
It's all going to be great.
But the pure pessimist, which the higher you get in leadership, the more pessimism you tend to be surrounded by.
When new ideas come up, particularly at larger, stagnant organizations, the knee-jerk reaction is to find all the problems and squash the ideas.
I'm not even sure why.
There is research on this subject.
I've bumped into it before.
But it's amazing how it's like, oh, I've got this idea and people would far rather find the problems and stop there.
So anyway, that's where I get to this place where, like, I've always viewed myself as – and I think it would be a pessimistic optimist because at the end of the day, I'm actually trying to do the thing.
I'm not trying to find reasons that it won't work and stop there, but I'm trying to find reasons that it won't work so that we can overcome those to get to the end goal or something resembling the end goal, right?
You don't always get exactly where you're trying to go, but somewhere near it.
Optimism, or calling someone an optimist or a pessimist, is a label.
It's a label you put on someone.
And my advice to anyone would be to be very wary of labels.
The human brain likes to categorize things and put things in buckets.
And even from a scientific standpoint, you see problems with this from time to time.
You know, a famous example of this is the way that, you know, like biological species and whatnot are categorized.
And even there, there are times when things don't fit cleanly into one bucket or the other.
But when it comes to people and labels that either others put on us or we put on ourselves, it's very rare that you fit totally cleanly in one bucket or another.
At least somewhere, right?
I'm not saying it's always true.
Like, obviously, there are labels and things that we do fit cleanly into some bucket.
However, there are other times where people will say, oh, and here's some, like, telltale things, right?
Oh, you're so bad at this.
Or you're so good at this.
Or you have no interest in this.
Right?
Like, oh, you know, you have no interest in learning a language or learning an instrument.
Or, oh, you're so good at picking up an instrument.
Or, you know, whatever.
Like, pick anything you've heard sentences like this said about you or you have said them to yourself.
The danger, I think, is hidden.
And it's that it becomes a narrative if you're not careful.
Because what happens when you tell yourself your whole life, you know, I'm really bad at learning languages.
Or someone else told you that along the way, but it gets internalized.
And what happens on that day when you decide you do want to learn a language and that maybe you could be good at it,
but you have this internal monologue or this internal thing that says, well, yeah, but I don't fit into that bucket.
I don't have that label.
I don't have the label of the person who can learn a language.
If you're not careful, that will cease the whole thing.
It will stop the whole thing right in its tracks.
And maybe you're not very good at learning languages.
But maybe this one specific language that you were thinking about picking up,
maybe that was the one you could have been good at.
But because you put yourself cleanly into one bucket or the other, you didn't.
Or you couldn't push that forward.
Or you couldn't overcome that mental piece.
So I have no problem thinking to myself that I'm a pessimistic optimist or an optimistic pessimist.
Or, and probably even better, that some days I'm one or the other.
We're a blend of the two.
But just be careful, is the message here, of adopting a label or cleanly adopting really any characteristic.
Because there will be days, and it could be a time thing, there will be days when you are or are not that thing.
And there also could be situations where you can adopt the opposite set of characteristics or buckets or labels,
at least for some short period of time.
And for that to be out of characteristic for you, it only expands your world.
So be careful of people who say things like, oh, you're so like this, or you're so like that.
Because maybe that's true that day, but it might not be true the next day.
And leave your mind open enough where you know that even if there are labels that either you have placed on yourself or others have placed on you,
that any day you could wake up and not be that anymore.
At least temporarily.
And at least when striving toward something new and different.
Even if it's just an experimental kind of way.