Stop SHOULDING All Over Yourself: Podcast 23

Stop SHOULDING All Over Yourself: Podcast 23

Stop shoulding all over yourself

Is “shoulding” even a word, Jeannie?

Well, sorta kinda.

Shoulding almost sounds inappropriate, which I find hilarious! 

So, shoulding. 

What the hell am I talking about? 

I’m talking about how many of us go through our lives judging past decisions super harshly.

I’m talking about beating ourselves up for every teeny tiny mistake we have ever made.

I’m talking about regret, when it’s totally unnecessary.


So I first heard this term coined by my beloved and awesome transformational life coach, Betsy Pake. 

Not sure if she actually coined the phrase or not, but I’m giving her the credit since she’s the first person I heard say it.

And what she said was something akin to: “Yeah, some of us are really bad about shoulding all over ourselves.”

I was in my car listening to her podcast – which I highly recommend (link in the show notes).

And I laughed out loud. 

One, because I have a demented and weird sense of grammar-nazi humor.

And two, because I can relate!

I’m always shoulding all over myself.

Shit! I should’ve remembered to get turkey bacon at the grocery store! 


Damn, I should’ve recorded an extra podcast so I’d be ahead (and not have to release one a day late because I was sick). 


I should be further ahead with my online course. 


I should refresh my resume.


I should just trust the Universe and just freakin’ quit my sucky ass day job. 

Because I want to.

I really, uber want to.

So I’ve been shoulding all over myself a lot lately. 

The problem with shoulding all over yourself is that you’re not being compassionate and loving with yourself.

Daring to change and think new thoughts is a rarity. 

It’s difficult and brave and courageous.

It freaks out your mind, makes you panic, and makes you question why you ever decided to think outside of the box to begin with.

Because going outside of the box – challenging beliefs you’ve probably been carrying around for a lifetime – is scary as hell.

It’s not familiar.

It’s not comfortable.

It’s the unknown. 

And our minds think it’s this deadly abyss of doom. 

It’s not. 

But our minds keep telling us it is.

Hence all the shoulding.

Our minds say, “You should stop applying for other jobs. You’ve had the job you have now for years. It’s safe.”

Even when our job is literally making us sick due to stress.

Even when we’re scheduled to work so many days in a row that even making time to go on interviews is difficult at best.

Even when we know in our heart of hearts that what we want to do is strengthen our business, but have a hard time doing so due to the hours required by the evil day job.

 Or, shoulding could go like this…

I should record that video, create those slides for online, and do a Facebook live or my business is never going to take off.

I should, I should, I should.

Or maybe you use similar but different terminology:

I have to do this.

I need to do that.

That’s shoulding, too.

And yes, to make progress, there are actions that we will take.

But if you’re not coming from a good emotional state when you take those actions, they likely will not work out.


I applied to this amazing online teaching program this week.

It entailed teaching English to children in China, and since its online, you get to do it from the comfort of your own home. 

It’s part time, but the pay per hour is better than my day job.

So, I gotta do this, right?

It’s a no brainer.

But there’s more to it than that.

Since you’re teaching children live in China, the time difference means you teach when you’re normally sleeping. 

Also, this process moves tremendously fast.

I applied on Friday, interviewed on Saturday, was given an appointment to train on Sunday, and was given a trial class – a class which evaluators watch and decide whether or not they want you – on Tuesday morning at 8am.

They want you to have the correct equipment set up and a fully designed classroom backdrop, toys, flash cards and games all ready to go for this trial class.

They also want you to have hours and hours of training videos watched before that first class.

Now I’ve taught middle school before, so I wasn’t that worried about it.

I also taught ESL to adults.

I thought, this’ll be fine.

The problem was I didn’t have any days off from the day job. 

I worked long hours Friday, Saturday, Sunday and Monday, and still had to find time to go shopping for teaching supplies, get new computer programs and headsets ready, and watch all those videos before 8am Tuesday.

Turns out, that’s a really tall order. 

I knew I had to watch a few videos, but I had no idea there would be hours and hours of them. 

Because watching these videos is required, I stayed up most of the night right before my class watching them.

I thought I understood the program interface, but apparently I didn’t.

So in the middle of this crucial class, I go to type something for my adorable 10 year old student – knowing all these eyes are on me -and it didn’t work. 

My lack of familiarity with this new system also meant my pacing was off. 

The fact that I forgot to shut my door so my cat Tink also came in and interrupted didn’t help matters much either.

So, here’s this great opportunity, an opportunity I’ve been asking for, and I blew it.

After the class, I tried to stay in a positive frame of mind and decided to go walking. 

But the shoulding started anyway.

I should’ve called in to work so I could focus on training and getting better rested.

I should’ve asked if I could practice with the software ahead of time.

I should slowed down, sped up, shut the door.

I should’ve… on and on and on.

So by the time I’m done walking, my worn out mind has pretty much left me in tears.

I look into the office I converted into a classroom last night, shut everything down, and depressed and exhausted, go to bed at about 10 this morning.

I play some meditations from the wonderful Rachel Thompson’s Mindful Mondays podcast, and slept for three hours.

When I woke, I was resigned to the fact that I’d lost my chance.

I kept telling myself that other opportunities would show up and to not feel so upset and down.

When I checked my email and saw one from the online teaching job, my heart sunk.

I was afraid.

This would be my nail in the coffin.

Deciding to just get it over with, I saw that they decided not to reject me outright.

They advised me to work with what they call a tutor trainer, so that’s the next step.

In short, all may not be lost. 

This job may be my saving grace or it may not be, but throwing in the towel is not the answer.

All I know at this point is that regretting the past is not helpful.

Sure, we can learn from our mistakes – the door will definitely be shut for the tutor training – but crucifying ourselves will not ever further our cause.

I’ll keep you updated on the new job front.

In the meantime, I continue to remind myself and you that all of this is a journey of discovery.

When you decide to grow and expand, you will sometimes run into difficulties.

It that part particularly fun?


But it is part of our becoming.

We are discovering who we really are and what we’re really capable of.

So the next time you start shoulding all over yourself about something that has already happened, stop.

Give yourself a break.

Remember how wonderful and amazingly brave you are for doing this in the first place. 

And know no matter what happens with any one opportunity, there are plenty more where that came from.


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