If I could tell my mid-20s self one thing
There’s a whole cultural narrative around our twenties - it’s the time to have fun, to party, to learn how to be an adult living on your own, to figure out what you want to do with your life and so much more. For a time that is constantly reinforced as a time for experimentation, there’s a lot of pressure.
In my mid-20s, I was deep in overachiever mode and was constantly in pursuit of feeling like I was doing the right thing. I wanted to get the promotion, be a girlboss and make more money. But at the same time, I was also trying to figure out the transition of my friendships from college into adulthood. How to date, when my experience at the time was a lot of lukewarm guys and situationships.
In summary, my 20s felt like I was constantly trying but not measuring up.
And I know this isn’t a unique experience. But since my mid-20s, I’ve changed a lot. I’ve learned a lot about how I feel about myself, about the life path I want to be on and about the things I thought then that were making it harder.
So this was the inspiration for today’s post. I know many of you are around here are in your mid to late 20s, and if so, this post is especially for you. (And any of my ladies in their 30s and 40s, there’s still an insight in here for you, I’m sure because it’s never too late to feel better about yourself and your life). So let’s dive in…
The confidence advice for your mid-20s that I wish I could go back and give myself
If I could zoom back like a modern day fairy godmother and give my mid-20s self one piece of advice it would be to…
Seek spaces of belonging, over fitting in
What do I mean by that? There’s an amazing Brene Brown quote, in her book Gifts of Imperfection:
Fitting in is about assessing a situation and becoming who you need to be to be accepted. Belonging, on the other hand, doesn’t require us to change who we are; it requires us to be who we are.
When I think back to my twenties, I think my entire life’s purpose, even in ways I wasn’t realizing, was trying to fit in. I wanted to work the way that my boss wanted me to in order to be accepted in the workplace. I wanted to look and act and date the way that I needed to be in order for the guys I was seeing to accept me. The days I drank, the games I played, the way I planned my schedule, the achievements I chased after were in pursuit of the acceptance of others.
And it makes sense why - we all have this intuitive, biological sense that if we are accepted, if we fit in, that we’ll be safe.
But here’s the problem (if you’re a Private Coaching client, you know exactly what I’m about to say)…
Safe is not the same as happy.
The sense of safety you get with fitting in is not the recipe for love, fulfillment, joy or satisfaction because you’ve anchored your entire sense of self in the opinions of others. And it’s really damn hard to maintain your “fitting in” status when you have dozens of people in your life, minimum, whose opinions matter to you.
Imagine an experiment where you have each of your friends individually and you ask them this: “I am going to buy all our friends’ dinner - where should we go?” What is the likelihood that without any coordination between the friends, they’ll all say exactly the same restaurant? What’s the likelihood that every single one of them will be even in the same cuisine? Zero. Nada.
And yet, that’s what we try to do with ourselves - let me survey all the people in my life and try to come up with the version of myself that will satisfy all of them. How impossible!
And it’s in this unwinnable game that we often find ourselves, sitting on the bed in our 2-bedroom apartment, dreading going to work the next day because you’re feeling stuck and looking over at your phone, knowing deep down that he hasn’t texted you and wondering, what am I doing wrong?
Or in my case, how I ended up one day sitting on the chair in the corner of my bedroom in a 4-bedroom apartment in the West Village, trying to keep my sobs to a low enough volume that my roommates wouldn’t hear as I had finally come to the realization that the guy I was seeing wasn’t looking for the same things that I was and that I still had to go to my job the next day and build another presentation to help big companies that I didn’t care about make more money. And all of this was going on inside of me while I knew, like KNEW that if somebody looked at my life from the outside, they’d be impressed. Where I lived, my friendships, my jobs, even the guy I had been seeing.
When you pursue safe, you pursue the average. The least offensive, least exciting, least interesting option because it’s the least likely to offend somebody in you world. But nobody really desires average. It’s not the thing you wake up going “oh my god, I’m so glad I chose the boring option.”
So when I think back to that girl in that moment, my first thought is: “I love you.” And then if I could go back and give her advice, it would be to seek belonging instead.
What does it mean to fit in
But let’s take a moment here - what is fitting in, really?
Some common examples of fitting in:
Dressing to trends out of a desire to be perceived a certain way
Staying quiet about your desires for anything (where to go to dinner, what type of relationship you want, your career dreams) out of a fear that you will be seen as weird or out of line
Pursuing a career that you know that your parents or family system will approve of, or even because it’s “stable and dependable” (which is often just the way that you’ve internalized your parents value of stability and safety)
Participating in social behaviors that you don’t particularly like or approve of like gossiping, drinking, judging, or certain lifestyle habits because you worry if you stop your friends might challenge you or feel rejected by you
These behaviors can feel small in the day-to-day but the message that you’re sending yourself anytime you participate in them is “who I am isn’t enough.” And then we wonder why we struggle with worries about not feeling enough for the guy we’re seeing or doubting our worthiness for the promotion!
When we have molded a version of ourselves around the opinions of other people, it generally means that we have trimmed away, we’ve compromised on the parts of ourselves that matter to us.
We are so worried about being rejected by others that we reject ourselves in order to avoid it.
And this is where that feeling of malaise, the sunday scaries or the “not enough” feelings start to percolate. Not because we’ve miscalculated on how to manage a situation or somebody else’s opinion, but because at the end of the day, the opinion we live with the most often, every single day is our own.
When you strive for fitting in, you create a world for yourself where you might find momentary calm of having everyone around you satisfied but you basically guarantee that in those moments, your internal world will be in turmoil.
And I don’t know about you, but I hated that feeling. When I think back to my mid-20s, that is the feeling I wish I could help her through, to help her see that she didn’t have to live with that inner turmoil in order to maintain the outer peace.
And this is where belonging comes in…
What does it mean to belong
Here is what the amazing Brene Brown says about belonging:
Because true belonging only happens when we present our authentic, imperfect selves to the world, our sense of belonging can never be greater than our level of self-acceptance.
If you’d like to drink less on Saturday nights but your friendship will fall apart if you don’t keep up with your friend’s binge drinking, then the friendship is with an idea of you, not the real you.
If you only get approval at work when you maintain inhumane working hours, then their approval of you is actually of the robotic, perfect employee version of you who doesn’t need rest or personal time, not the real human.
If we cannot be our authentic, imperfect selves and be accepted, then we are not really accepted at all.
I wish so dearly that I could get this idea through to my mid-20s self.
Now, if you’re in this place, I know you’re smart enough to rationally understand that if you have to pretend to be somebody you’re not in order to get them to like you, that they don’t really like you and the relationship, friendship or working relationship won’t be sustainable in the long term.
And yet, even though we understand this on a rational level, we still obsess as to why he has pulled away and should we be texting him less often and maybe we shouldn’t have said that thing about wanting a relationship and… spiral.
In that overthinking spiral, the undercurrent is “who do I have to be in order for him to like me?” Fitting in.
If instead, we were to pursue belonging, we’d be focusing way more of our time on becoming the version of ourselves we are most proud of - not for the approval of others but to be able to look at ourselves and the way we live our lives and feel proud.
Looking back to the Brene quote, “our sense of belonging can never be greater than our level of self-acceptance.”
In order to belong, you are the ultimate arbiter of whether you approve of yourself. You cannot rely on the positive (or negative) feedback from others. So it requires much more self-trust and self-reflection to really get clear on who you are and who you want to be, the areas that you’re already doing great and the areas where you’d like to improve.
To belong, we have to show up before we’ve got it all right. Because we will never have it all right.
If we wait until we’ve perfected our body, gotten the promotion, figured out our abandonment issues, started working out 3x a week and are hosting monthly dinner parties, it’s likely that we’ll continue to berate ourselves with the things that aren’t yet right.
This is the hardest part about belonging and the thing that I am still working through as a 30 year old.
The path to belonging requires accepting yourself for being a work-in-progress and letting other people see you that way. Because that is a very important part of who you authentically are.
I am a recovering perfectionist and it’s my general desire to show an image to the world of authentically imperfect in the perfect way. I want to be relatable in my imperfections but not confronting or challening. I want to show you all that I am still working through my own stuff, but not share the messy uncomfortable parts.
This is what I work through regularly - trusting that even if I share a problem before I figure out a solution, that I will be okay and that I can love myself through that (and others will love me too).
If I were to be speaking to my mid-20s self to try to explain this to her, I would remind her of a few things:
“You love your friends even when they’re in the midst of a breakup and an emotional mess, or when they’re feeling lost about their work or when they have a hangry, low patience day. Part of this experience even feels good to you because you can help them see how worthy they are even when they can’t see it. But if you never show the same in return, not only do you rob yourself of the support but you rob them of the experience of getting to do the same for you.”
“What you feel to be imperfections might be the thing that somebody loves most about you. Your journey to figure out dating might, if you were willing to more vulnerably share it, help somebody feel seen and understood [editorial note: this is often what I feel about this business I’ve built!] or your process to work through the stuff that’s coming up for your family might show somebody a vulnerability that they find incredibly attractive. Just because you think something is a weakness or unattractive trait, doesn’t mean that other people see it that way.”
“You’re never going to be able to keep doing this forever anyway. So why delay the inevitable of trying to figure out another approach?”
I’m sure that if my mid-20s self needed to hear these things, some of you do too.
How to start moving in the direction of belonging
Okay, so you’re bought in that belonging, not fitting in, is the long term goal. But what do you do about it?
First of all, I’m proud of you and I know it might feel a bit scary right now but this journey is worth it. I speak from experience. As I have gone on the journey in pursuit of belonging over fitting in, I have:
Accepted that I didn’t want to climb the corporate ladder and left a job I wasn’t happy in to start my own business which I love
Started communicating my preferences more openly with my best friends (previously, I had kept quiet about certain topics like my opinions on work, my ideal lifestyle and relationship dynamics because I knew they held different beliefs) and to my surprise, they absolutely supported my point of view even though it was different than theirs because they acknowledged that we were different
I stopped trying to maintain the lifestyle that I thought “looked good” living in NYC and started traveling more and spending more extended time out of the city which has been incredibly nourishing and enjoyable and my friendships haven’t suffered as a result (like I feared)
And that’s just scratching the surface. So just remember that there’s so much promise in this journey for you.
If you are just coming to this conclusion and starting out, here’s what I recommend you do first:
Spend some time reflecting on why you want the various points of your life you have now - can you trace the desire to something your parents wanted for you or something that’s popular in your group of friends. Then ask yourself, do I authentically want this thing? Does it give me intrinsic joy or satisfaction? A powerful question to ask yourself, “If nobody was around to see it, would I still want this thing?”
Start tuning in your day-to-day life when you feel the most satisfied or fulfilled. Let yourself daydream, if you were to turn those things up to 11, what would it look like? Pay attention to the fears and stories that come up about logistics and what people will say - these are your fitting in narratives and they’re the pieces that you can begin to work through to make it feel more safe to actually pursue belonging
Begin adjusting to the idea that there is some loss in this process. Some people are only comfortable with us when we are convenient for them and as painful as it is to lose a relationship, whether a friendship, romantic or familial, because they are only willing to invest in us when we’re compliant, it is absolutely long term for the best because that friendship, relationship or family member will keep you stuck in fitting in mode. The sooner you figure out who these people are, the easier it will be for you to pursue belonging.
Once you have begun clarifying your vision for what you think might authentically satisfy you, the challenge is just to start chipping away at creating that life for yourself. Remember, your belonging can never be greater than your self-acceptance so the journey is to look at the life you’re living and feel proud and satisfied in yourself. We will never get 100% of the way there, but the more secure we feel in this, the easier it is to disregard the people who want you to be something that’s not authentic to you.
