Everything I got wrong in my twenties

Welcome back to another episode of how to twenty-something and happy 150 episodes!!!!

This is crazy, 150 episodes in so i think it’s only appropriate to run through everything I’ve gotten wrong in my twenties

I’ve been hosting this podcast for nearly 3 years now.. Episode 156 will actually mark 3 years since there are 52 weeks in a year

But no one care about 156 like they do 150

So this episode is a break down on things I believed, things that felt broken, and what came about as a result

It ties into a theme that keeps running through my mind, especially when it came to my tedx journey and that is: i’m glad things didn’t work out so they could end up working out

And what I mean is that when you have a vision, a dream, a goal, a 5 year plan, whatever it may be and it feels like everything is going wrong or you can’t catch your break or no one is giving you chance to prove yourself

It’s frustrating

And it’s really hard to put faith in everything working itself out eventually

Because you want it to work itself out right now.. Rightfully so

And I can rewind to so many different moments where this was the case and that’s kind of what this episode is for

To help you see that everything that is seemingly going wrong in your life is to actually set you up for what’s meant to be

Relationships, career, friendships, your health, every single no.. all of it

And before I begin, I want to emphasize that we listen and we don’t judge

Because you don’t know what you don’t know until you know 

And you’re going to hear me talk about a lot of different moments where you’re going to want to reach through whatever device you’re listening on right now, smack me on the forward and say ‘should’ve had a v8’

If you don’t get that commercial reference, please go look it up

But the whole i’m glad things didn’t work out really came through with my tedx journey

You see, I applied to two tedx’s in 2024 and didn’t get either

And then applied again, when I actually had no intention in doing so last year, 2025

But I was on a walk and got hit with an idea of you’re not as special as you think you are and was like hmm. That would be a really good ted talk

So why not apply, what do I have to lose

I applied to one the next day and I actually got to the final interview where it went from 350 applicants down to 30 and was being brought down to 15

So less than top 10% which is a pretty big freaking deal

I thought I was a shoe in

It was at a university, my message is for college students and young professionals, I knew people involved, I had this

And then I didn’t get it

So I immediately applied with the same idea to tedx sugar creek women

I knew my idea was too good not to be heard to the world

Timeline wise, I found out I didn’t get the first tedx 45 minutes before going to an event where I ran into cara, who runs tedx sugar creek women

And at this event I was getting feedback on a talk I was giving to a networking group

So cara got to see my stage presence first hand, my ability to take and apply feedback, and I go to share my idea with her in person 

She told me she was finalizing speakers that day and that my idea fits perfectly with the women she’s already selected so I need to get my application in as soon as possible

I filled out my application on a tuesday and thursday night cara told me to call her

My grandma self was already asleep so i responded friday morning and at 9:15am she told me I’m going to be one of the speakers

Here’s where it gets even better

My entire tedx experience was so wonderful, it was supportive, it was relational, it was incredible through and through and I know had I gotten the other tedx I would not be able to say the same

I attended the other one, and the people, the talks, the format, the subjects, even the audience.. Would not have worked in my favor like tedx sugarcreek women

Things didn’t workout so they could end up working out

And there a lot of these moments that happened in my twenties where in the moment it sucked, but in the end it was for the best

So while you probably can’t relate to my ted story, it is the instigator for this episode idea

But let’s rewind things back a little bit to everything I was wrong about

Starting with where I was going to live after college

I spent my college career believing that after I graduate I was going to move to atlanta 

I only applied to jobs there, I got interviews pretty easily with different places, and what I got wrong was not asking for help 

I had too big of an ego of “I can do this on my own..” Like I had something to prove 

And all that did was get me ghosted by every single company I interview for in Atlanta

I’d like to say I learned my lesson, but truthfully I didn’t learn my lesson at any point

I spent that entire summer interviewing and hearing nothing or hearing no’s

And then I accepted my first job in celebration florida and it hit none of my requirements that I came up with which were: pay, location, and style of design

My requirements were minimum 45k, in a big city, and ideally corporate or entertainment design

This job was 36k, 30 miles outside of a big city, and retail and restaurant design

And where did that leave me? Unhappy in a job and in my commute 

And then unemployed 7 months later due to the pandemic

Nothing seemed to be working in my favor

I didn’t like living in Orlando, I didn’t like sitting at a desk all day, and I was bored out of my mind

I was wrong about where I said yes to my first job, but it led me to navigating unemployed life, questioning my purpose, becoming a personal trainer, seeing the world of entrepreneurship at a time when I had nothing to lose, and later becoming a coach for all of you

The expectations I got wrong about my career turned out to be the best thing I could have ever imagined for myself

I mean I could even take it back even further and say I was wrong about what to major in in college

I was never an interior designer, I knew it from the first day of classes when I ran into a girl I did gymnastics with who I had nothing in common with and we were in the same major

I remember that day so vividly, but I was stubborn and I viewed changing your major as a failure

Since no one else in my family changed their major

I was wrong

I was wrong that you shouldn’t change your major… you absolutely should trust your gut when you know something isn’t a good fit.. Regardless of what people will think or say about you

But again, the wrong major, led me to the wrong first job out of school, that led me to learning a lot about growing up in a short time frame, that led me to being the coach for twenty-somethings 

So that’s pretty much everything I got wrong about my career in my twenties

The next category of what I got wrong is in regards to my health

I was always someone who was very conscious of my body, the way I looked, the identity that came with being small, petite, skinny

So I was terrified of the freshmen 15

I developed the worst habits like skipping meals, or eating dry cereal and a banana or apple until 1pm

So when I was 20 I was diagnosed with pcos

Now for me, it was actually a sugar problem in my body since i was not eating healthy in a way I thought was conducive to keeping me small

I was on a prediabetic track

I was afraid lifting weights would make me bulky, so I mainly did cardio, I was afraid of eating food because I didn’t want to get fat

The result was breaking my foot at 19 and getting diagnosed with pcos at 20.. Two big health wake up calls that I still didn’t take seriously

These patterns carried on for the next few years and I became obsessed with working out and eating less

We’re talking 1200 calories a day and if I ate more than that I felt really bad about myself

So my other foot broke when I was 21

And part of my recovery after being in a cast for 6 weeks and a boot for 6 weeks was physical therapy

They taught me to squat, deadlift, lunge.. Lift weights

And I began building muscle and looking good, and eating a little more

So I thought more is better

And more is most definitely not better

I would walk an insane amount miles and lift for 2 hours almost every single day

And would excuse this routine as it’ll normalize once I have a full time job

Which it did.. I was right about that

But I was wrong about pushing your body in the gym every single day

Fast forward to now, I’ve been consistently lifting weights twice a week.. Yup that’s it.. Two times a week for the last two years

I’m eating more than I ever have in my entire life, and I look and feel the best I’ve ever felt

And here’s the biggest thing that changed

I was wrong to chase a number on the scale or a clothing size or to keep my high school pre-pubescent body.. Things that probably sound obvious

I was also wrong that lifting weights makes you bulky and eating more than 1200 calories makes you fat

I was wrong that you need to workout 6 days a week otherwise you’ll gain weight

I was wrong about the metrics I was chasing for my body

It wasn’t until I started chasing a regular period, did I start to see the results i had been craving for a while

There’s a saying I want you to pay extra attention to if you’re someone who has fallen into the same traps I previously had and it’s:

If you chase aesthetics your health will fall, if you chase your health aesthetics will follow

And it’s true and it’s something that took most of my life thus far to actually believe

So that’s what I wrong with my health

The next category is dating.. Remember we listen don’t judge 

I will say a lot of what I got wrong with dating had more to do with my own self worth and being a child of divorced parents who didn’t see her dad all that much, wasn’t your typical father figure, and passed when I was 13

I had a lot to learn on my own

And those lessons came with being wrong about who I let into my heart

I’ve talked a lot about my ex on this podcast and it’s because that relationship taught me so much about myself

About what I was looking for and most definitely what I wasn’t looking for

But I’ll say a lot of what I got wrong was also from dating random people for 3 years between relationships 

I was wrong about how I am to be treated by the guy I’m dating

You should almost never feel unloved, disrespected, scared to bring up certain conversations, uncared for, you’re too much, you shouldn’t be anything but happy, or just not a priority in this other person’s life

If you’re heart is pounding or your stomach is doing flips, those aren’t butterflies or nerves, those are warning signs

Your nervous system should feel pretty calm 95% of the time

EVEN if you’re an anxious girly like me

That’s what that 5% is for

I was wrong about what I thought I deserved

I tolerated bare minimum behavior because I didn’t think I deserved anything more or I’m not worthy enough to receive more or ask for more

I was wrong about what I thought love was supposed to feel like

I was wrong about holding onto the potential someone has instead of looking at the patterns

You should never hold on to the hope of who someone could be and instead ask yourself: if nothing changed about this person 10 years from now, would you still be happy?

And the biggest thing I got wrong when it came to my relationship with my ex was that ending it meant I was a failure

It’s the same thing when it came to changing majors in school, changing your mind or bringing something to an end meant I failed and that is 100% not the case

Having the courage to walk away means you succeeded 

You found your worth, you said yes to yourself, that’s so much more valuable and impressive than staying where you know you don’t belong 

And that brings me to the last area of life that I got wrong in my twenties: friends

Friend groups, what a friend is.. And isn’t, and what to look for in a friend

I thought I needed a big group of friends and that it was embarrassing to go to the bar or to an event with just one other person

Truthfully? I still think going to events with a group of people is more fun, but it’s not how you deepen the relationships you have with these people

There’s also more drama when you’re dealing with multiple different people, personalities, and opinions

I was wrong in how I define friendship.. I used to define friendship as anyone to go do stuff with

And I’ve learned that friendships are the people you trust, confide in, and open up to

I was wrong in what qualities I looked for in a friend

I went from seeking out the planners, the life of the party, the people who have high social status

To seeking out the people who think of me, include me, support me and who also thrive on one on one interactions over the flashy highlight reels on social media

Something that still trips me up is what a best friend looks like in the city I live in

Because while I would love to be spontaneous with someone and just show up to their place or vice versa or make last minute plans.. I also know I can’t be that person in return

But when there are gaps in my weekend it’s all I can think about

I know I don’t want someone who is always available, but it’s also nice to have another person to do life with outside of ryan 

It’s just it always feels like everyone is too consumed in their own lives to make room for a new friend and that’s hard on the mind

This topic is so relevant that I actually decided to create a course around it called how to make adulting suck less

Because it sucks to do life alone

And I’ve also learned that people want villages but haven’t thought about becoming a village first

So i made a 5 video series course for $37 that is game changing when it comes to deepening your relationships, how you show up, and what you believe to be true about how you relate to other people

You can head to the show notes or go to jessdiamondcoaching.com/strengthen to read more about it

But when I tell you this is the best thing I’ve ever created, believe me

It truly is the best thing I ever created and I want you to become the person who believes they are worthy enough and capable enough to have strong relationships in your twenties and the rest of adulthood

So go check it out right now

And as you do so I’m going to zoom out of the individual categories of my twenties and sum it all up as the main theme across it all that I got wrong in my twenties was thinking that I had to earn my worth

That quitting things or ending relationships or leaving situations meant I was a failure

That asking for help is a sign of weakness

That no one actually cares about you’re going through

I was wrong about all of it and I’m sharing this with you so you know that the opposite is true

That self worth is not earned

That quitting, leaving, or ending things takes a lot of strength and courage

And so does asking for help

And that the right people care so so so much about what you’re going through

And I don’t blame myself for getting these things wrong.. It’s what your twenties are designed to do for you

And as you get closer to thirty you become so much more sure of yourself and everything you’re inviting into your life

It’s part of the decade long learning experience

So if you’re listening and you’re in your twenties.. Learn from what I got wrong but also know that the things you’re getting wrong are part of this phase of life

And you don’t know what you don’t know

And like i said.. I’m glad things didn’t work out so they could end up working out

Because if everything worked out like I originally planned from the get go then I wouldn’t be here talking to you, giving a tedx talk, creating my first ever course, feeling so fulfilled in the business i created from scratch, dating my boyfriend, I wouldn’t be exactly where I am

And I happen to like where I’m at

Finally, as I wrap up this 150th episode I want to speak to those of you who have grown up with me over these last three years… Thank you for letting me be wrong out loud.. Even though I only really share when i’m wrong after the fact

But seriously, thank you for listening to another episode of how to twenty-something

If you liked what you heard, learned something new, know someone who is hard on themselves for getting things quote unquote wrong in their life.. Then share this episode

Post it on social media, congratulate me on a 150 freaking episodes, send it to a friend just do something that helps me help all of the twenty-somethings navigating the most confusing decade of their lives

Here’s to another 150 episodes

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