Summary

In this episode of “How to Twenty-Something,” I address the common issue of “shoulding” on ourselves – the tendency to set unrealistic expectations based on societal pressures or comparisons to others. I discuss how this mindset can lead to feelings of inadequacy, stress, and low self-esteem. Throughout the episode, I offer strategies to reframe these thoughts and focus on personal growth and individual paths. Key topics include understanding the root of “should” statements, the impact of social media on our perceptions, and how to shift from “should” to “could” thinking.

Key Takeaways:

  • Recognize that “shoulding” often stems from unrealistic expectations and comparisons
  • Understand that everyone’s life path is different and valid
  • Reframe “should” statements to “could” statements to open up possibilities
  • Focus on personal values and desires rather than external expectations
  • Limit social media consumption to reduce unhealthy comparisons
  • Practice self-compassion and acknowledge that you’re always “on time” for your own life

Why do I feel so behind in life compared to my friends?

Because up through high school, everyone moves at roughly the same pace, but after graduation people scatter onto totally different paths. That contrast feels jarring, but “different” isn’t the same as “behind.” You’re comparing your current chapter to everyone else’s highlight reel, not their whole story.

How do I stop comparing myself to a timeline I set for myself years ago?

Recognize that the timeline (engaged by 25, house by 26, married by 27) was usually borrowed from your parents’ generation or society, not something you actually chose. The world you’re building a life in now looks nothing like it did 20-30 years ago, so holding yourself to an outdated blueprint is setting yourself up to feel like you failed at something that was never realistic to begin with.

How do I figure out what I actually want instead of what I think I'm supposed to want?

Write down your ideal life and the values behind it, on purpose, without attaching a timeline to it. Then pick one small action this week that moves you toward it. If you get stuck figuring out even that first step, that’s usually the sign it’s time to get outside support (a coach, mentor, or someone who can help map the path).

Related Episodes

Ep. 128 Stop Getting Ahead of Yourself

Ep. 1 Overcoming Your Negative Self Talk

Ep. 23 What are you grateful for?

Ep. 76 Overcoming Imposter Syndrome

Ep. 157 How to Stop Letting Your Mistakes Live Rent Free in Your Head

 

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Transcript

Stop should-ing all over yourself

 

Welcome back to another episode of how to twenty-something, with me your host, Jess, and today I want to help you to stop shoulding all over yourself, god I love puns

 

We all love to play the game of should’ve could’ve would’ve and I’m here to help you reframe all of that and to know that no matter what, hindsight is always going to be 20/20

 

It’s a tough concept to grasp for sure but it’s coming to terms with you made a decision based off of the information you had in that point in time, then you learned something based on that outcome and beat yourself up over the better decision you could have made given this new information

 

I think it all really boils down to stop being so hard on your current self for the decisions your past self made

 

We can’t go back in time, at least not yet, time travel hasn’t finalized at this current moment and besides if you’ve ever seen any time travel show or movie, then you would that’s dangerous to go back and change something as it throws your whole trajectory off and the entire world blows up

 

But anyways we can’t go back in time and do something different, all we have is right now

 

And the concept of shoulding on yourself stems from uncertainty in the decisions your making and society’s pressure on you to get it right the first time around and be born into the adult world having it all figured out

 

Which is pretty absurd when you think about it because we are the toddlers and children of the adult world and as a result have many many mistakes to be made in our future and lessons to be learned

 

It’s inevitable

 

There’s a saying that fits well with this episode topic and that is, the best time to plant a tree was 100 years ago, the second best time is right now

 

Meaning, sure making a different decision a year ago would have put you in a better position today, but you can still choose to change your path right now, it’s not too late

 

Take your health for example, if you had started your health journey last Summer, when you were feeling crappy about yourself, then by this Summer you would have looked and felt entirely different

 

That doesn’t mean you will never be healthy and feel good about yourself, it just means you didn’t start earlier but you can still start today

 

Now, throughout this episode I’m going to be giving you many examples that will help you to move forward without letting your awful, negative thoughts hold you back

 

Or in other words, not let your feelings of regret enter the chat

 

One of the biggest fears my clients come to me with is a fear of regret, they are so afraid they are going to make a wrong decision that will result in them looking back on this time in their life and feeling like they did it all wrong or missed out on a major opportunity

 

What I get to help them with is get really clear on what it is they want out of their life and then formulate the steps necessary to help them get there while simultaneously making sure they aren’t the ones standing in their own way

 

And that whole process helps them to stop shoulding all over themselves

 

I think we need to begin by first recognizing what is actually happening in your mind when you do begin the shoulding process

 

When you should on yourself you are setting unrealistic expectations for yourself either based on society’s expectations for where you’re supposed to be in your life by a certain age or from your family and friends with what they say or by seeing where they’re at in life or worst of all, by yourself and the timeline you created based on those other factors

 

You might find yourself saying things like I should be engaged by now, I should have 100,000 in my bank account, I should have a house, I should be promoted, I should have a great group of friends, I should have a better body, I should have it all figured out and insert any other should that you conjure up for yourself

 

This way of thinking becomes prevalent in your early twenties and doesn’t go away because this is usually the first time in your life where everyone in your same age bracket is off doing something different

 

And as you age, everyone will continue to be off doing something different from you

 

That doesn’t mean you’re doing life wrong or that you’re behind, it simply means you are doing life differently than what you’re seeing around you

 

Social media likes to constantly throw everyone else’s lives in your face

 

But up until graduating high school everyone moved through life at a similar speed, yes some people were smarter, some were more athletic, some had jobs starting in high school, but for the most part you guys all grew up together

 

Then by high school graduation a majority of people follow the college route and by college graduation everyone splits to their own unique paths

 

For example, all of my friends had jobs lined up right after school or new what they were doing next and where they were going

 

I had other friends know they were going to grad school

 

Other friends who knew they wanted to move back home

 

And here I was feeling really crappy about myself for not knowing where I was going next, and getting ghosted by every job I received an interview for over that entire Summer

 

It didn’t help that everyone in my family would ask for updates all summer long and I would say if there was an update I would tell you

 

Fast forward to being out of school for a solid five years and some friends are back in school, some are getting married this year, some bought a house

 

Some got married right after graduation and have two kids now, which is crazy for me to think about

 

Others didn’t get married but have kids now

 

Everyone is in very very different places in life and it can make you feel poorly about yourself because it provokes this self talk of where you’re supposed to be instead of acknowledging where you are and how far you’ve come

 

So I want to help you, while honestly helping myself, feel better about our individual trajectories and how we show up day in and day out so we stop shoulding all over ourselves

 

And this all stems from the comparison game – you’re either comparing yourself to someone else or comparing yourself to where you thought you were going to be by a certain point in time

 

When you should on yourself you are making yourself feel inadequate or behind in life and that causes a lot of unnecessary stress and anxiety which then results in lower self-esteem

 

Low self-esteem is probably one of the most significant factors that demotivates you to do something about the part of your life that you feel behind in

 

So now, not only are you tearing yourself down for not reaching your self-imposed expectations, but you’re also decreasing your likelihood of doing something about it because you’re stuck in this oh fuck me mentality

 

And I think the most ironic part of shoulding all over yourself is that you probably don’t even want that specific life anyways

 

But since everyone around you wants it you think that you need it too

 

It’s why I stress that if you’re single you need single friends as much as friends who are in healthy relationships

 

Take it a step further, if you have kids you need friends who also have kids

 

If you feel all alone on your little island you’re going to start doubting every move you make, even though you originally got to your island by making decisions that aligned with your values and what truly matters to you

 

Or with the way life unfolded itself for you

 

When I lost my job during the pandemic, the job I originally struggled to land in the first place, I felt all alone on my little island

 

I couldn’t control my furlough, I couldn’t control the global pandemic, I couldn’t control my friends situations, or the fact that the government wouldn’t give me unemployment assistance for the first three months

 

Those were not my decisions to make

 

However, what I did with my new found free time was up to me

 

My decision to begin my personal training certification, to take up reading self help books, listen to podcasts, and help my mental health in as many ways as possible was up to me 

 

Those were all decisions I made based on the situation I was in and that aligned with what mattered the most to me in that moment

 

One of my pillars in my own your life signature transformational system is control and that’s because we need to learn what we have control over and release the parts we don’t – we can control our actions and reactions

 

And we can’t control literally everything else

 

But they way you react to a situation that is out of your control will help you make an empowered decision as to what to do next

 

Regardless of what everyone else around you is doing, seeing, being, or having

 

Because what you see is what you believe and if the way you’re living doesn’t look like what you see around you then you’re going to have more self-doubt and insecurities and feel less inclined to share yourself with the world around you

 

Or you’ll feel like the odd man out who is doing something wrong

 

That self-doubt and low self-esteem comes together to lower your self-confidence

 

Now you’re going to feel super insecure about sharing your lifestyle with the fear of other people judging you for not living up to their perceived standards

 

When in reality, it’s all in your head

 

People are far too concerned with their own lives and where they are lacking to even give one ounce of care towards what you’re not doing or achieving right now

 

Basically, the should game is your one way ticket to unhappiness

 

It goes back to feeling the need to check all the boxes by the time you’re thirty

 

I think growing up a lot of us, myself included, would say something along the lines of I’m going to be engaged by 25, have a house by 26, married by 27, and my first kid at 29

 

And then you reach the age 25 and you realize how far off you were from that original timeline that you created for yourself when you were in middle school

 

That timeline was exemplified by our parents generations so it’s something we thought would stay true for ourselves, but what we failed to take into account is how different our lifestyle and world in general is today compared to what it was say 20 to thirty years ago

 

So we feel defeated for not being quote unquote on time

 

When in reality, you are always right on time for your life

 

And maybe some of you did follow life in that order which is fine, it’s not saying that that timeline is incorrect it’s simply saying that it is unreasonable for everyone to achieve

 

We all live very different lives with different dreams, goals, and situations that it’s unfair to you to create some absurd timeline based off of society’s recommendation

 

But it makes you feel like you’re an outcast or not normal for wanting something different than your peers

 

When in reality, they probably want something different themselves they just don’t know how to make that change happen or are afraid of the judgment that my be accompanied by this change

 

That judgment and rejection creates a shame spiral that serves as a distraction to what it is you truly want and not what others want for you

 

This shame then drives you away from talking about your current lifestyle or what you’re working towards and results in weaker relationships because you’re not sharing a big part of who you are and who you’re trying to be

 

I remember in college everyone would ask you your five year plan, and for me it was graduate school, move to Atlanta, live there for 3-5 years, meet the love of my life, move to North Carolina, get a house and settle down

 

That five year plan was dead wrong when I got ghosted by all of the firms in Atlanta and ended up with a less than ideal job in the greater Orlando area

 

And from that point on I stopped planning out five years in advance

 

As I’m planning out this episode my book club is reading Brene Brown’s book, I thought it was just me, and it talks a lot about shame and vulnerability and I think shoulding on yourself ties right into that theme

 

So the next time you catch yourself shoulding all over the place, I want you to pause for a moment and ask yourself are you making a decision or having a thought, based on an external expectation or your own personal desires?

 

And if you are having a thought based on an external expectation, how can you reframe that thought with could as in what could you do so you feel in control of your life

 

Like I said earlier, should is feelings of regret it’s wishing the ability to go back in time and make a different decision somewhere along the way to bring you to a more desirable result in the present moment

 

It’s also a word for giving up, or in other words, there’s nothing you can do about it besides throw yourself a pity party

 

Versus swapping the word should with could means you’re learning from a past experience and are willing to change something to have a different future outcome and not be left in the same cycle

 

For example, I should have 100,000 dollars in my bank account right now to I could have 100,000 dollars in my bank account right now if I start saving it’ll be possible down the line

 

I should is a failed expectation

 

I could is it’s possible for me, now how do I make it happen?

 

It’s such a slight difference with a huge positive mental shift 

 

Let’s do another, I should be married by now

 

Meaning everyone else around is married, I’m single as shit, and I feel undesirable because no one loves me in a romantic way

 

Compared to I could be married by now

 

Meaning, and mind you this is no jab to people who got married young and solely for my shoulders who are single, by changing it to could you’re saying I could be married, but I choose to wait until I find someone that adds value to my life and is a marriage that is really healthy

 

I could marry the next person I lay my eyes on but by waiting I am making sure I find a person that is right for me and the life I want to build

 

This is fun, let’s do one more

 

I should have a better body

 

This is a tough one for me because I say this to myself all the time, I eat well, I move my body, I get good sleep, I have the perfect formula for having an amazing body, and yet I feel as though it should look better

 

That’s me comparing myself to past me and to other females

 

Switching it to I could have a better body but that might mean sacrificing my internal health like my hormones and my energy levels

 

Should narrows in on the one thing you’re lacking, whereas ‘could’ widens the lens and looks at what else is happening as a result or what actions are you in control of to help you overcome your own self-pity

 

When you’re focusing on what you don’t have based on what you see other people around your age do, you’re letting yourself lose sight of what truly matters to you or what your definition of success looks like

 

Another easy fix for overcoming the should game is to write down your ideal life, the things you really want to achieve or create for yourself, pull out the values that are aligned with those goals, and do not, I can’t stress this enough, do not put a timeline to this life

 

Just acknowledge what it is you’re working towards and come up with one action you can do this week to help move you towards the life you want

 

And if you don’t know what that one action is or even the next one after that, then that’s when it’s time to work with a coach

 

This is my specialty I help create your roadmap and guide you along so you don’t feel so stuck in your current life

 

Think of me as the lion, the scarecrow, and the tin man and you’re dorothy trying to get to Oz

 

So I’m guiding you along your yellow brick road to prevent you from getting lost

 

My coach teaches a yellow brick road system to organic marketing but I feel like this analogy also works to help you conceptualize how working with a coach moves you along your path of life

 

The last tip I’m going to give to help you stop shoulding on yourself is to limit your social media consumption

 

I know I mentioned this is the social media episode from a few weeks ago, but it’s true, when you get caught up in the death scroll you’re exposing yourself to unrealistic portrayals of other people’s lives

 

Remember, people are only going to show you their milestones

 

No one outside of my close circle knows when I have a breakdown or feeling stressed beyond belief

 

Instead my social media followers see success and happiness or a story about a past struggle that I’ve already worked through

 

When you let go of all of the shoulds in your life you are releasing this giant pressure weighing you down to meet certain expectations in a certain order and on a certain timeline

 

You start to make choices that align with the future you want instead of a life someone else is living, thereby increasing your confidence behind the decisions you’re making

 

You become better equipped to handle life’s ups and downs and have more faith in the universe that you are exactly where you’re supposed to be you’re not behind or ahead, you’re right on time

 

And you fully accept your life path for what it is that you’re working towards and feel fully in control of any past present or future experience that comes your way

 

Now, like everything, changing your mindset is a process, so for this next week think about the most prevalent should you have in your life and find a way to start moving the needle from should to could to can to will

 

It’s time that you start living life by your own terms

 

Shoulding on yourself aint cute honey so cut it out

 

I mean we all do it, we’re all guilty of it, but hopefully by now, as I wrap up this episode you feel a little more equipped to standing strong with where you’re at in your life and inspired to move forward

 

And like I said earlier, if you need help with this, if you need someone to guide you through your life and help you develop the confidence you need behind the decisions you’re making and the path you’re on, then please schedule a call with me

 

It’s completely free and it’s just a way for us to connect and for me to get you started with how to alter your life for the better

 

All you have to do is click the let’s chat link in the show notes and pick a day and time that works best for you

 

And as always thank you for listening to another episode of how to twenty-something, if you liked what you heard, if this episode resonated with you or you’re taking action based on what you just heard, then please share it with a friend or post it on social media and tag me at coach.jessdiamond when you do

 

Help me reach other twenty-somethings who are shoulding on themselves

 

Otherwise this does conclude today’s episode and I can’t wait to be in your headphones again next week with another brand new episode



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