How to Stop Letting Your Mistakes Live Rent Free in Your Head

Welcome back to another episode of how to twenty-something where today I’ll be talking to you all about what to do when you make a mistake

Whether it’s at work, with a friend, in your own privacy, and pretty much any situation where you were like oh shit

Now, i’m not talking about the big giant mistakes like cheating on your partner, saying yes to a job you end up hating 1 month in, driving drunk, gambling all your money away, or anything else pretty major 

No 

These are the tiny things

Saying the wrong thing and accidentally hurting someone’s feelings

Emailing the wrong person

Tripping in front of your crush

Inputting the wrong order or wrong numbers at work

At one point or another we’ve all made a mistake and then if you’re anything like me or my clients, you dwelled on it far longer than you know you should have

Where your mind gremlins take over and tell you the worst things about yourself bringing all of your insecurities to the surface like 

This is why I don’t have a lot of friends

I’m so stupid

I can’t do this

I’m going to lose my job

This episode topic actually came up after a client of mine made her first mistake at her first full-time job

She texted me freaking out and since I know this client very very well at this point in our partnership I knew how to support her and remind her that she’s spiraling because she cares

That this is a normal reaction to being human, BUT we don’t want to dwell here

She found out about this mistake as soon as she left work for the day… why she was checking her email at her car 5 minutes after walking out, I have no idea

But she let this mistake ruin her entire evening and then felt guilty for ruining her boyfriends evening as a result

It was one spiral into another into another 

Thankfully she texted me about it so I could talk her off of her ledge and remind her she’s not going to lose her job, if there is nothing you can do about it right now then you need to switch into self care mode, and being 3 weeks into a job means it is totally inevitable that you are going to make a mistake

Even 3 years into a job you’ll find yourself making mistakes, why? Because you’re a human

And humans aren’t perfect

Now, this client is a known spiraler and lucky for her I am great at getting people to stop spiraling

So much so that I turned it into an easy 3 step process and packaged it into a free pdf just for you, all you have to do is click the link in the show notes or go to jessdiamondcoaching.com/spiral so you can access the 3 ways to stop spiraling 

And while you go fill out your name and email I’m going to get back to the episode you’re listening to which is how to stop letting this mistake take over your entire day 

To quote the fabulous hannah montana, everyone makes mistakes, everyone has those days

And this client was having one of those days

When you have a fuck up whether it’s at work, in your relationship, when you’re on a nutrition plan, the worst thing you could do for yourself is continue to think about the thing you did wrong

There’s a high probability that you’re tying this mistake to your worth and capability as a person and that’s why you start spiraling into worst case scenarios about how you suck and would be better off crawling in a hole and dying

Dramatic I know

But that’s basically what your thoughts are doing

This client was turning a little oopsy into her entire personality and because she cares and wants to do well in her new job and is someone who is very very polite and apologetic I knew I needed to tell her one thing and coach her around another thing after 

I told her the one thing she needs to absolutely make sure of is to not over apologize

You’re naturally going to turn something into a bigger deal than what it actually is

So here’s what you do when it comes to apologizing, say you’re sorry when you learn you made a mistake, acknowledge what you did wrong then move on to the next thing.. That’s what an apology is

It’s a oops I didn’t mean to and I will try my very hardest to not let that happen again

Then ask how to do it correctly or better, apologize maybe one more time and then and I’m going to repeat this: MOVE ON

It’s done, it happened, you can’t go back in time, all you can do is learn and move forward

Shake it off, go for a walk, switch to another task but stop apologizing 

The part I coached her around was her sense of control

When she texted me, freaking out, the very first thing I asked her was, is there anything you can do about this right now or does it have to wait until you’re in the office tomorrow?

She said she can’t do anything right now that she replied to her boss’s email apologizing and that they’ll figure out a solution in the morning

Then she stopped texting me for like 3 hours and came back saying she’s still very upset about it

And that my friend is because you’ve entered into imposter syndrome

That’s where the tying the mistake to your worth comes into play

Especially when you’re new in your career or new to a job that maybe you feel you’re not the most perfect fit for… a stretch role if you will

So when you mess up your brain doesn’t go I made a mistake, but instead convinces you that you are the mistake, that you don’t know what you’re doing, they’re going to realize they hired the wrong person, you don’t belong here

Your first mistake as an adult, especially at work, will feel like the end of the world but it’s because you haven’t had time to build up your own proof that one mistake doesn’t define you

So now you’re wide awake at night freaking out over this, while your boss is happily tucked into bed snoozing away knowing it’s not that big of a deal and will be taken care of during working hours

Because everything is always figuroutable

You’re letting this mistake live rent free in your head, so let’s shift gears into what’s actually true here

Making mistakes is part of the process, it’s how you learn

Your boss makes mistakes, the ceo makes mistakes, I’ve made mistakes as a coach, friend, employee, girlfriend, daughter, sister

Mistakes are part of being a human

I could go and on about different mistakes I’ve made in my life and some that haunt me to this day but I don’t shudder at the thought of them anymore, I use them as reminders of what I can do differently next time

For example, I messed up with communicating with a client once where she kept canceling and/or rescheduling last minute for different reasons and I was ready to talk to her about it during our session.. To which she canceled 30 minutes beforehand so I said it over text how unfair this is to my schedule.. I did say it better than what I’m paraphrasing for you right now 

But it was her reaction that made me realize i messed up and now I’ve learned to always lead with compassion first

When a client needs to reschedule the very first thing I ask is ‘is everything ok’

And that has made all the difference

Now my client feels supported and we move through this together and then discuss my cancellation policy

That mistake happened in 2024 

And i’ve signed a ton of other clients since then but it’s something I replay in my head a lot… as a reminder not as a dweller or spiraler

I like mistakes, not in the moment, in the moment they suck

But mistakes keep you humble, they show you you’re human and that you’re open to learning, that you’re not perfect and you’re relatable 

What matters is how you recover from the mistake, the way you handle it is what people will remember

You might remember this until the day you die, but anyone affected will remember your reaction and then action to it

Which is what control is

Your mistake wasn’t intentional, you’re not a bad person, and you’re going to try your best to right your wrongs

So let’s shift into the recovery part

First things first

After the obvious, acknowledge you made a mistake and apologizing, the next thing for you to do is give yourself a window to feel bad or space where you can throw yourself a pity party and then you have to decide that when that time is up you are going to move on

And the reason why I say this is what you need to do first is because your brain is not going to think logically about this until you let some emotion out

You’re allowed to feel embarrassed, frustrated, disappointed, ashamed, upset… literally any and all the feels 

So make sure you’re not burying them down but acknowledging what’s coming up for you

This time limit you give yourself is going to vary based on the situation 

For example, if it’s the middle of the work day, you probably have 5-10 minutes to walk it off or be somewhere private

But if it’s like my client’s example and it occurs at the end of the work day you get to decide if you want this moment to consume your entire evening or if you want to set a shorter limit

Neither answer is necessarily wrong, but remember you’re not getting paid to overthink off of company time

So do with that what you will

Step 3 is come up with solutions, if you can… basically fix what you can fix with the information and accessibility you have

This is where you’re not making excuses for what happened but you are providing solutions to help right your wrongs

Step 4 is the coaching part.. What can you learn from this

Now the mistake will become something useful like how I now learn to lead with compassion when someone wants to reschedule even when it is annoying on my end.. Their experience matters more to me

So why did this happen, what can you do differently next time

This isn’t ruminating on the oh me’s oh my’s of this fuck up, it’s reflecting so you can grow forward from it

And step 5 is reminding yourself that you are not the mistake, you made one.. They are separate and it in no way means you’re wrong for the job, the friendship, the relationship, the world, or whatever other scenario you want to fill in

The goal is never to never make a mistake, it’s to become someone who knows how to handle it when they do.. Because you will

This isn’t your last one, it’s probably not the first one you’ve made in your life either

But replaying what you did on repeat in your head is why it’s living rent free… and free in this economy is a foolish choice

So make those thoughts vacate the premises because now you’ve learned what you needed to and are able to move on

And that my friend is how I am going to wrap up this episode of How to Twenty-Something.

If you liked what you heard, have ever made a mistake at work and spiraled from it, or know someone who is currently in that spiral right now — please share this episode.

Give me a five star rating, post it to your story, send it to a friend, just do something that helps me reach all of the twenty-somethings navigating the most confusing decade of their lives.

And as always I cannot wait to be in your headphones again next week with another brand new episode.