Summary

This episode of How To Twenty-Something talks about the complex world of imposter syndrome—how it shows up in our careers, relationships, and daily lives, especially in our twenties. Imposter syndrome, the persistent doubt in our abilities and the fear of being exposed as a “fraud,” is so common during this period because of all the new transitions and challenges we face. In the episode I shared how this can lead to underestimating our accomplishments, comparing ourselves to others, and even avoiding new opportunities. To combat it, I suggest building confidence with wins folders, embracing support networks, and pursuing your own path without constant comparison. 

Key Takeaways:

  • Your self-confidence is directly related to the severity of your imposter syndrome
  • Every new experience let’s imposter syndrome creep in
  • Create a wins folder so you have something concrete to refer back to
  • Relationship imposter syndrome is based on your own self-worth
  • Comparing yourself to other people will invite imposter syndrome into your head

What is imposter syndrome and why is it so common in your 20s?

It’s doubting your own accomplishments or skills and fearing you’ll be “exposed” as a fraud, often attributing success to luck rather than ability. Your 20s bring constant new transitions — first jobs, promotions, independence — that push you out of your comfort zone, which is exactly when imposter syndrome tends to surface.

How do I stop comparing myself to people online who seem more "put together"?

Recognize you’re comparing your real life to someone’s curated highlight reel — often literal strangers. Practical steps: change your social media algorithm, mute or block accounts that trigger negative comparison, and keep a running “wins folder” of your own accomplishments to reference when you’re doubting yourself.

How can I build self-confidence to overcome imposter syndrome?

Keep a “wins folder” documenting accomplishments as they happen (useful for career doubts and promotion asks alike), develop interests and hobbies outside your relationship or friend group so you feel whole on your own, and consider therapy or counseling if the feelings run deep — self-confidence is described as a muscle that needs consistent building.

Related Episodes

Ep. 1 Overcoming Your Negative Self Talk

Ep. 64 Your Sneakiest Fear: The Fear of Success

Ep. 88 In the face of rejection

Ep. 68 Stop Should-ing All Over Yourself

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

 

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Transcript

Overcoming Imposter Syndrome

 

Welcome back to another episode of how to twenty-something where today I am going to dive deep into the topic of imposter syndrome

 

For those of you who aren’t familiar with the term imposter syndrome, it’s when you doubt your own accomplishments or skills and have a fear of being exposed as a fraud with whatever you’re setting out on to accomplish

 

It’s attributing any success you do achieve to luck rather than your own abilities and then having this looming feeling that people around you will eventually realize you’re not as capable as them

 

It falls under the fear of success which I had as an episode not too long ago, but I think imposter syndrome is a subset of the fear of success because it encompasses both sides of accomplishing something

 

The before: where you limit yourself from going after an opportunity and the after: when you chalk your accomplishments up to luck and don’t believe you actually earned what you achieved

 

This is so so so common in your twenties because it’s often brouhgt on by new challenges or transitions that force you out of your comfort zone, which is a pretty regular occurrence throughout this decade and why I wanted to talk about it on this podcast

 

We are constantly getting thrown new experiences and it really makes you doubt your abilities as to whether or not you are capable of handling them or any other challenge that will arise

 

Part of the work I get to do with my clients is getting their shit together or in other words, breaking down different adulting responsibilities into more bite sized pieces so that by the end of our partnership you are a fully functioning adult and feel confident about who you are, how you exist in the world, and the direction you’re heading

 

And that confidence over powers imposter syndrome

 

Not to be confused with living in a state of delusion but rather being realistic around your own goals and aspirations and a reliable and sustainable road map to get you there

 

I had a client recently tell me, Jess when did I become an adult, and I joked and said when we started working together

 

She went from living life, a bit too much in the moment, to planning for her future, budgeting, eating three nutritious meals a day, seeking out a new job opportunity, balancing her social life, meal prepping, moving her body, god the list goes on

 

And this wasn’t achieved overnight either, this took months because it’s a process and it takes time to learn and then further develop these adulting skills

 

Most of us, if not all of us, get thrown into the adult world and are just expected to know how to do everything, but the part they don’t tell you, and by they I mean the older generations, is that they had to fall flat on their face multiple times before they got their shit together

 

Yet they expect you to just know what to do

 

They are so out of touch with their twenties that they forget about the struggles and tough life lessons they once experienced too

 

But it’s because they didn’t have a coach like me to make this transition through your twenties much much easier

 

That and it appears that our parents and grandparents generations had a much more straightforward path to follow where you go to school get a job and you’re set

 

Going off the beaten path wasn’t common because salaraies kept up with cost of living

 

Today, inflation is so high that many twenty-somethings need multiple jobs to keep their head above water or realize going off on their own will earn them more

 

I was part of the second group because my job choice had such a low cap of earnings where the most i would ever be able to make as a senior designer working under someone else is about 80,000

 

As an entrepreneur I have a very realistic goal of making 100,000 by 2026

 

But the decision to become self-employed also comes with needing your shit to be insanely together and your self talk to be able to overcome the imposter chatter that goes on in your head

 

However, I will say, if you do not feel like a fully functioning adult yet, then you are going to feel overwhelmed by your independence

 

No one is checking in on you and making sure you’re paying your bills, eating healthy foods, moving your body, and navigating your career path, social life, and finances, just to name a few

 

So what happens is you get overloaded with the uncertainties behind these new responsibilities, thus making you question your ability to handle them

 

And that is imposter syndrome

 

Imposter syndrome is very normal, but it’s time you learned how to identify it and overcome it so it doesn’t talk you out of going for something or being recognized for something you did

 

This episode is going to highlight what happens when you let imposter syndrome take over your mind, where it might come up for you and what you can do about it

 

Or, in other words, create your own antidote to this unavoidable syndrome

 

To begin, I primarily see imposter syndrome show up in people’s lives when it comes to their career and any career related transitions like a new job, a promotion, a recognition, going back to school, or starting your own business

 

And then outside of your career, imposter syndrome even surfaces when you compare yourself to those on social media or around you and if you are someone who suffers with perfectionism 

 

It even shows up in your relationships when you lack confidence in your own worth

 

When imposter syndrome controls your mind you’re also letting it control your actions so you’re more likely to avoid new opportunities and hide out from the world

 

It prevents you from taking risks like applying for a new job or promotion because you don’t think you are capable or ready

 

Statistically, this is more common for females than males

 

Hewlett-packard did an internal review back in 2014 and found that men will apply for a promotion where they meet 60% of the requirements, whereas women will only apply when they feel they meet 100% of the requirements 

 

Now, that is not true for everyone and every job, but it is referenced a lot and it directly relates to your self-confidence and your relationship to imposter syndrome

 

Women are more likely to go after something when they feel qualified, if not overqualified for it and will otherwise self-select out of opportunities and men will are more likely to apply despite not meeting certain qualifications

 

It’s just something to keep in mind when you’re looking for a new job or wanting to apply for a different position, just go for it, the worst that happens is that they say no and you stay where you’re at

 

But better staying where you’re at because you tried versus not even bothering because you didn’t meet every single requirement listed

 

Another example in life where you’re strengthening your imposter syndrome is when you compare yourself to people you see online 

 

We all know this is not a good thing, because you are viewing people, who are most likely strangers and influencers showing you a snapshot of their life, and leave you feeling like everyone your own age is more successful, confident, or quote on quote together than you and therefore you are fucking up adulting

 

And when you compare yourself to others you’re going to start to doubt every decision you’ve made and are making

 

And for my fellow entrepreneurs your imposter syndrome will scream at you and cause you to worry about your capability in running a business and being successful, and as a young entrepreneur you will worry about not being taken seriously

 

I started my business when I was 24 and that was a big fear of mine, that no one would want to work with a 24 year old because of how young I was

 

And while it’s true, I was very young, I was also extremely capable in helping other people get their life together because I was forced to early on and had to overcome my own struggles all by myself

 

I had no other option but to grow up right then and there before I was ready, before I knew how, and my god it sucked but it brought me to where I’m at today and now I get to help you grow up at a much easier, slower, and more manageable pace so life doesn’t force you to in a moments notice

 

That being said, I have had people who are older than me work with me and trust me and I have had people who are older than me choose to not work with me because I was younger than them

 

That was a tough learning experience and looking back i know it had nothing to do with me and everything to do with their insecurities and ego, possibly even their imposter syndrome was taking over

 

Even after running a business for 3 years, my coach still helps me to word things so it’s not interpreted as who does this 27 year old think she is but rather listen to the value, knowledge, and expertise I do provide, regardless of my age

 

I also think imposter syndrome comes up in the entrepreneurial world when you compare your chapter 1 to someone else’s chapter 20

 

Because the truth is, unless you sit that person down and listen to the their whole story and their struggles and the time it took to build their business to where it’s at today, you’re only going to leave yourself to fill in the missing gaps

 

And I would put money on that fact that those gaps you are filling are making yourself feel worse not better

 

Now whether you’re an entrepreneur or a corporate world employee, the best way to combat imposter syndrome that’s centered around your career is to keep a wins folder

 

You need to document every win you collect as you collect them so you can bank to refer back to for when you start to doubt yourself or your success

 

P.s. it’ll also be helpful to have this folder to help you feel more confident about asking for a promotion because you have the proof to back up why you deserve a pay increase 

 

And with that you won’t even give your imposter syndrome a chance to talk you out of it because you have the concrete evidence as to why you earned this promotion

 

Outside of career related instances, imposter syndrome also likes to creep in on your dating life

 

Like who am I to receive love or why would this person like me and it becomes more of a question of your self worth

 

Do you believe you are worthy of a healthy and loving relationship?

 

Are you questioning if you’re good enough or if your partner deserves someone better?

 

If you frequently visit these questions in your own mind then you are succumbing to imposter syndrome

 

This can also come in the form of struggling to believe the compliments your partner gives you or that anyone gives you, for that matter and maybe you think oh they don’t really mean it, they are just being nice

 

It’s because imposter syndrome drives this need for constant reassurance that they do like you, that they would love you even if you were a worm

 

And if you are one who suffers with imposter syndrome in relationships then you have this looming fear that they’ll leave you once they find out who you really are or they’ll leave you when they finally come to their senses and see that you’re not good enough for them

 

As a result you’ll close yourself off emotionally because you won’t let yourself be vulnerable with this person with a fear that they will leave you when they see your weak points, or worse, use your weak points against you

 

And that lack of vulnerability creates distance between the two of you which will only further confirm your original beliefs that they won’t accept you for you because someone better is out there for them

 

Because remember that your beliefs create your experiences and your experiences confirm your beliefs

 

So if you believe you aren’t worthy of love then you will hide out from potential mates or current partners, and as a result no one will love you which will then confrim that belief that you aren’t worthy of love

 

Imposter syndrome in relationships becomes a really big issue when your partner is also suffering with similar thoughts 

 

For example, my ex would constantly bring me down, so instead of talking about his vulnerabilities and insecurities he would point them out on me

 

He would play connect the dots with my acne because he used to have really bad acne and went on accutane when he was in high school

 

He would tell me he would leave me if I gained 5lbs but it’s because he noticed his own weight gain and would feel self conscious about it

 

He would remind me all the time that he was settling and I was reaching because a lot relationships do have a settler and and reacher

 

It didn’t help that at the time my guy friends would also say the same thing, come to find out later that they were messing with me and said all along i was settling 

 

And let me tell you, I was settling, maybe not at first but I grew so much and became such a stronger and better version of myself, that I was settling and holding myself back by staying with him

 

But I honestly never experienced imposter syndrome in that relationship, I was however a victim to his imposter syndrome and it damaged our relationship

 

If you’re the one suffering you might unknowingly find your self sabotaging your relationships like pulling away or even ending a relationship because you think your partner will eventually leave anyways so you might as well cut it short now before your heart becomes too invested

 

And insert fear of commitment to the chat

 

No but seriously, if you’re suffering with imposter syndrome in your relationships then please know there is a cure, so here are some things you can do to at least begin the process of overcoming it

 

You need to communicate your insecurities with your partner

 

Yes that sounds scary but trust me when I tell you this: everyone has insecurities so if you open the door the other person will most likely contribute to what they feel insecure about

 

And if they shame you for your insecurities then please leave that person

 

Another tactic you can begin doing is accepting compliments and love at face value, meaning don’t give one back or downplay the one you’re receiving

 

Practice saying thank you and then shutting your mouth

 

You can also practice building your self confidence outside of your relationships by developing interests and hobbies outside of what you guys do together

 

Find your own thing to do and step into it

 

Doing things a lone helps you get to know yourself better and helps you find a partner that adds value to your life instead finding someone who completes you

 

Because you’ve already built a life that is hole and complete by yourself

 

Finding someone who completes you implies that you aren’t a whole capable being outside of this relationships which enhances that imposter syndrome because you become so afriad of missing a piece of you if the relaitonship comes to an end

 

Versus going into a relationship already whole and wanting someone who can help you uplevel and make your life even better

 

And then if you’re really down bad in this syndrome, please seek counseling or therapy to help you dig deeper as to where these feelings and thoughts come from and how you can grow past it

 

There is nothing wrong with getting support with something you are struggling to overcome on your own

 

But at the end of the day, you are going to experience imposter syndrome in multiple different parts of your life

 

The ones I mentioned are the most common occurrences and they all really boil down to one thing and I’ve said it several times today already: your self-confidence

 

You need to work on building that muscle up so it’s strong enough to withstand the pesky thoughts that talk you out of being able to achieve what you’re after

 

Stop comparing yourself to what other people are doing versus what you’re doing, change your social media algorithm, block people’s stories that enhance negative thoughts about yourself, and create a folder of accomplishments to be able to reflect back on for when you are feeling crappy about yourself

 

It doesn’t even have to be work realted accomplishments but a life folder of you winning and acknowledging those wins

 

I have a client who just started working with me and on our first call before we were even in a coaching partnership she mentioned that she sees her friends and her boyfriend living full lives and she’s messing everything up

 

Yet when we dove a little deeper she realized that she was living her life based on other people’s priorities and not her own so when she would be alone during the week, if her boyfriend was traveling, she would feel empty, lost, and confused and on the weekends only go out with him

 

So she started doubting her career choices and her ability to find and make new friends by herself

 

Her imposter syndrome came from looking at other people’s lives and comparing it to her own and her remedy was to start showing up for herself and take action based on what aligns with her top priorities

 

As her coach, I make sure she is doing that and folllowing through on what she says she wants from her life

 

And with every win she collects her imposter syndrome voice softens

 

Imposter syndrome is sneaky, but hopefully by now you are better able to understand it and catch it in the act

 

And please know that if this is something you struggle with, because if you’re someone in their twenties listening to this, then I’m 99% sure you do, that I can help you

 

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

 

Otherwise this does include another episode of how to twenty-something, if you liked what you heard, learned something new, or know someone who struggles with overcoming their own imposter syndrome then please share this episode

 

Send it to a friend, post it on social media and tag me at coach.jessdiamond when you do, and give me a five star rating so more twenty-somethings can receive support and help

 

And as always, I can’t wait to be in your headphones again next week with another brand new episode

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