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What if the problem isn’t your job, but the version of yourself you had to become to succeed in it? Corporate jobs don’t trap us because they’re evil. They trap us because they slowly teach us to disconnect from ourselves. If you're in corporate America and your life looks successful on paper but feels empty in practice, you’re not alone.
This podcast is a space for the quiet questions you don’t say out loud at work. We explore the inner side of change: the fear of starting over, self-sabotage, the trap of external expectations, imposter syndrome, and the unsettling moment when you realize someone else’s definition of success isn't enough for you.
This isn’t about quitting your job overnight or chasing money, but asking what feels right for you and finding clarity before making your next move. We deliver actionable strategies for complex career transitions. From managing ADHD-related overwhelm at work to overcoming the disconnect of the corporate grind.
You’re not broken. You’ve just outgrown the life you built.
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Foreign.
Hello, and welcome to episode 95 of Working
towards our purpose. In today's episode, we're going to talk about
overcoming the fear of failure and
a mindset shift that we'll talk about at the end of the episode. Before
we get into that and before we get into the episode, just going to take
a moment to slow down, check in with ourselves and see how we're
feeling today.
All right. Yeah. Hopefully you got a second to slow down,
to take a breath in, perhaps a busy day.
So for me, if I'm checking in with myself, I'm. It's a little gloomy out.
Has been, I feel like, for the past few days, so
feeling a little bit lower energy, but. But got
some. Got some good things in the works. Been doing some
cool stuff and excited about that. Been working on
some music. Been playing some music.
Yeah, got. Got a quick little, like,
month, like, side gig that's related into audio, which I'm excited
about. Yeah. So feeling
good overall. And today, you know, this episode
is about overcoming the fear of failure. And
I'm not quite sure where I first started thinking about
this. I think I was talking to somebody who was, like,
starting a new job or a new career or making some sort of big move
and just talking about being, like, afraid of it. And, like, it's. It's scary. Like,
change is scary. And I think that we all
have a fear of failure. And. Well, maybe we don't all,
but I certainly did growing up. I actually
remember one time we were in, like, maybe middle
school or something, and we were, like, kind of filling out this sheet of
things about us, and one of the questions was,
like, what is something that you're afraid of? And
I can't quite remember how it went, but people were putting spiders and heights and
stuff like that, and I remember putting failure
on mine. I'm afraid of failing, and I don't even know
why. I don't even know if I knew what that meant at that
point. Um, maybe I just thought it was, like, a
cool answer or like something that the teacher wanted to
hear or something. I don't know. But it is quite interesting that, like,
the. This fear of failure is, like, so built into all of
us, it seems. Again, I don't want to speak for everybody in existence,
but I have talked to a lot of people who are afraid of failing, and
it makes sense. We don't ever want to, like,
do something wrong or. Or fail or be embarrassed
at getting something wrong. But I think,
and this is no shock, but the fear of
failure holds us back a lot of times. And I think if I were to
think back when I was leaving my corporate job, I was petrified
that I was making a wrong decision and
that it wouldn't work out. And I
don't know, I think anything you can kind of look, look back. Anything that you've
done and made a change
or got a new job or went somewhere
crazy for school or whatever, there's always
two sides of it. One, oh, this could be a mistake, or it could be
really good. And I think that, I don't know, sometimes maybe you have to
risk that looking dumb or doing
something wrong to. I don't know, I'm rambling.
But. Yeah. The point is, I think that the fear of failure holds us back
a lot. And it's understandable that. I think
even just the way that we're brought up in our school systems, that's kind of
all we know up until graduating high school. It's like, you take a class,
you have to pass or do well on the test in order
to continue on and get to the next grade. And everything is
just structured around not failing. And I mean, look
at the letter grades that we get, right? F is for failure.
And it's like this horrible thing. So it makes
sense as to why we're all kind of afraid of failure and why we're trying
to avoid failure. And especially that's not even
to talk about. If you had a parent or a parental
figure that was a perfectionist and wanted you to be perfect,
which I know a lot of people struggle with also just the
idea that you have to be perfect. So, yeah, it
makes sense why we feel failure. And I guess I was just kind of thinking
more into this. And I guess from my
perspective now, I'm like, yes, I
conceptually understand that fearing failure is
natural and not something that you have to let hold you back.
But it doesn't mean that it's easy to fail
or that you want to go fail. I think I still,
like. I know that it's like fake, like the fear of failure
doesn't. Doesn't matter. But I still
will sometimes not do things because I'm afraid of looking stupid or
like looking dumb or sounding bad in music.
So, yeah, I mean, just because you understand something doesn't mean that, like,
you'll act in that way because it's still hard because you still have to
overcome years and years and years of
trying to stay as far as possible away from failure.
So just because you maybe want to face failure head on
now doesn't Mean that all the time you can.
So for whatever that means. But anyways, as I was kind of
thinking more and more about failure and the fear of failure, I guess I like
to dissect things. And maybe that's not a surprise if you've been listening
to this podcast. But I've been trying to think about how I felt as
a kid as failure. And there was kind of two things
that. Two
thoughts that came to me that were kind of planted into my head when I
was a little kid and growing up and adolescence and that sort of thing.
The first one, and they kind of have to do with the fear of failure.
And the first one was that things can either be done right or
things can either be done wrong. So you're either doing something the right
way or the wrong way. And
this is very black and white thinking, and
of course not true. I think almost
everything can be done more than one way
correctly. You could do a math problem different ways and get the same
answer. So there's not just one way of doing something. And I think
that may have come from schooling too. But I think for me, a lot of
it came from my father wanting to have me
succeed and having good intentions for me and wanting me to learn
and that sort of thing. But he was very much of the mindset of the
way that I know how to do it is the right way and anything else
is not the right way. So it gave me this idea that
in life you either do something the right way or
you mess up and you do it the wrong way. And for a long time
I thought like that. And for a long time I thought like,
gee, I hope I'm doing this the right way. Like if, you know, if I'm
doing something new or, yeah, going out and like,
starting my side business and stuff, I was like, I was really worried about doing
something wrong. And it kind of like makes you afraid
to do something because you're afraid to do it the wrong way. And
I've learned since that there's not the right way and the
wrong way. There's like a multitude of different ways you can do something and
they all teach you something. So none of them are really the wrong way.
But that's now with a different perspective on failure and not being afraid
of failure, but knowing that, quote,
unquote, failure will teach us something. So that was the first thing.
The first thing was the black and white thinking of right way, wrong way.
And I thought like that for a long time. And
then the second thought that came to mind
in thinking about how I felt about failure as a kid was
that the wrong way is the hard way or the hard way
is wrong? The hard way is wrong. That's a tongue twister.
And again, I think for me, this came a lot from my father of, like,
he would always say, like, work smarter, not harder. And a lot of
times, not that that's maybe a bad phrase, but I
think a lot of times that came off to me,
the way I understood that was like, if I don't do it the way that
he thinks is right, then I'm doing it wrong, and I'm wasting my time and
I'm doing something bad. So I always thought that
doing something the hard way was a bad thing. So I would always
try to find the easy way to do something. I would always overthink things and
try to think my way through something Instead of just using my
intuition or hitting an opportunity when it came
and figuring the rest out later. I would always overthink things. And
I think that this isn't special to me. I think a lot of people think
that the hard way is the wrong way. And I guess it kind of. You
know, in thinking about this episode, I questioned myself, and I was like, yeah,
huh? I guess I kind of still do believe that the hard way is the
wrong way. But is it?
Is doing something the hard way the wrong way to do it? Is it not
worthwhile if you do something the hard way? And I think I just
started questioning more that maybe that's not
a bad thing. Maybe doing something the hard way is what's
needed. Because you just. I don't
know, you think about all the courses you see online and all these classes
and people trying to teach you how to do stuff. And not that they're
bad, but a lot of them are always like, here's the best way to do
this. Here's the fastest way to make money. Here's the easiest way to do
this. And again, not that that's not valuable,
but I think sometimes we. We forget
that doing something the hard way actually teaches us something
valuable, like determination and
willpower or grit. Maybe I'm
hesitant to use that term, but I think back to when I
learned how to play guitar. And there's no easy way to learn how to play
the guitar. You have to sit there and fuck up your fingers
for weeks or months, and it's super
painful. And then eventually you can start
playing notes and playing chords and playing songs that you want to know, that you
want to learn. There's no easy way to do that. And
everything probably shouldn't be done the hard way, but
just something for consideration.
Maybe some things are worth doing the hard way.
So, yeah, that was interesting to me. That thought was interesting to me.
And I thought I'd share in this
conversation of failure and thinking about
how we can let failure hold us back. So, you know, if. If that made
any sense, take it. If it doesn't, then don't. But. But those were two thoughts
that kind of came to me as I was thinking about failure and, like, how
we can deconstruct. How I can deconstruct failure and not
be. Not play into it, not let failure
or the fear of failure drive my decisions.
Because I think that if we can make
decisions based off of not fear, like, if we
can make decisions based off of our gut and
hope and positivity and that sort of thing, that ends up
maybe leading our lives in a better direction than kind
of just bouncing around and being afraid of things.
So, yeah, those are the two things.
These are, I guess, maybe the two myths that from my childhood
and my growing up, that things can only be done the right way or the
wrong way. Very black and white thinking. I think that's a myth, and then
that the hard way is the wrong way. And I also think that that's a
myth. So now moving past this, okay,
we understand maybe failure isn't such a bad thing
and maybe it has a lot to teach us. But
how do you go from somebody who's always avoided failure
to now somebody who can take failure head on? And
I don't think there's an easy answer to this, but I think
the answer for me has been exposure therapy
and just doing it, just failing, going and doing
something. Maybe it's not a huge thing. Maybe you don't go take out a
business loan and then default on it, but go do something that
is hard and fail and
not even failures. I don't know, it's not even a good word. But
I guess for me, if I'm thinking about something I've done recently,
this year I started going to open mics and
playing my music out, which is something I've never done. My own music, singing
guitar. And the first one was really hard.
And actually all of them were probably pretty hard. None of them are, like,
easy, but I had one,
like, two weeks back. And I don't know, it was like the perfect
setting. I was feeling comfortable and
I felt like I did okay. I felt like I was like, okay. That wasn't
too bad. That was pretty good. And that's big for me because I always am
super hypercritical. But it was just a reminder
of the repeatedness before I go. Every time I'm like,
do I really want to go? I don't know. It's so much easier to sit
home and not go, but forcing myself,
exposure therapy, doing the thing that you're afraid of and repeating
to do it, repeating it
and putting in the reps and slowly it becomes easier.
And I think, I think in doing that
it's gone on to different areas of my life.
Practicing going up and sucking sometimes
and making it through and still being alive and being like, you
know what? Afterwards I always feel this. I'm always like,
well, I'm proud of myself. Either way I did it. Even if it wasn't perfect,
who cares? I tried and I'm getting better and that's great.
Um, so confronting that like
fear of doing bad or embarrassing myself,
I think it's made me more courageous in other areas of my life too. And
I think like the other opportunities I alluded to earlier, I think
you know, part of that is like, like, you know, applying
for things that maybe I think I'm not that qualified for on paper and just
like taking a chance and like not being afraid that of a no. Not being
afraid of. Not being afraid of a no and it leading
to good things. And yeah, I think that
all that to say is that if you're afraid, maybe if
you're someone right now that's afraid of making a change in your life or afraid
of failure, I would say start small and
just fail at something. Just try it and see where it
takes you. Because I think there's real
good stuff, there's real knowledge
and perspective in failing at something. And
yeah, you just, you learn so much more from failing. And
not that it even has to be a big massive failure, it could just be
like a little thing. But yeah, I mean I know
this is a probably super over talked topic about fearing failure,
but these are my thoughts and hopefully they're
helpful. If not, that's cool too.
But thank you for listening, thank you for being here,
thanks for making it to the end and if you did, and maybe if
you're somebody who is hard on yourself and you're
your own worst critic, I know what that feels like
and it's not fun and it holds you back from, from trying
things. And if you would like some help with
trying to soften your inner critic, I've made a free seven day
guide to try to help soften your inner critic. If that's something that interests you.
There's a link in the show, notes in the YouTube description.
Wherever you're watching this, there's the link everywhere. It's
free to download and it's everything that I've learned about being hard on myself
into one like PDF document. So hopefully it can be
helpful to you if you enjoyed this. But that's all I got for you today.
I will see you on another episode real soon. Thank you for listening
and have a great day out there. Take
care.