Why Relatability Matters More Than Advice in Your Twenties

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You’re listening to how to twenty something, the best podcast that helps both men and women navigate their twenties and learn how to “adult” across all aspects of their lives

We’re going to focus on career, relationships, finances, fitness, nutrition, and all of the common challenges and obstacles a typical twenty something will face in this post-college life

I’m your host, Jess Diamond, and I am the CEO and founder of Jess Diamond Coaching where I help young professionals get their shit together, gain their confidence, and own their life

No one prepares you for this adulting world so allow me to help you feel like you are no longer a chicken running around with its head cut off, and that you actually know what the hell is going on and what your next step to take is

Welcome to How To Twenty Something

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Welcome back to another episode of how to twenty-something where today I’m going to be talking to you about the importance of finding the people who just get it

This is something I very much pride myself on when it comes to being a twenty-something who works with twenty-somethings

And even once I enter my thirties I think it’ll still apply until the next catastrophic life altering event shapes the next generation of twenty-somethings

So until that happens, it’s the pandemic and the age of ai that has grouped us all together for the foreseeable future

And that is very important when it comes to feeling supported in your twenties

You need to surround yourself with the people who just get it more than you need to seek out advice from the people you know

There is something so important around finding who you relate to and it’s something that isn’t even necessarily dependent on age but rather dependent on experience

Age just happens to be a big point behind this opinion of mine as it pertains to twenty-somethings and it’s something you hear me say a lot: that if you were not a twenty-something within the last 6 years you cannot relate to a twenty-something today

But this opinion of mine was even further confirmed when I went and volunteered at experience camps at the end of July, which for those who don’t know experience camps is a nonprofit for kids who have lost a parent, sibling, or caregiver and the kids go to camp for a week for free 

I’ve been a camp counselor there for three years now

And each bunk is assigned a grief specialist who is a mental health counselor in the real world

The girls I had this year were new to me and 15 and 16 years old and their grief specialist was a women in her fifties if i were to guess

So when i tell you there was zero relatability or understanding between grief specialist and camper, i mean zero

Not in terms of understanding grief, but more so in terms of understanding them as a person which I find to be an incredibly important factor when it comes to feeling heard as you get older, regardless of shared experience like someone in your family dying

And i’m not claiming to understand and be a perfectly relatable match to an incoming sophomore in high school, nor am I saying that high schoolers should seek out other high schoolers for help but I sure as hell am not as outdated as a fifty something

This is no hate to this women, she is a really good counselor for little kids, but not for teenagers, teenagers are a different breed, just like twenty-somethings.. Which is exactly the point i’m trying to make

And it’s why you need to find your people who do get you, but can challenge you at the same time, support you along the way, and be able to explain why you think certain things or view the world in a certain way from a relatively current point of view

It’s finding people who share a similar perspective of how the world works based on the time you grew up in

Not to be confused with avoiding people who have opposing views as you politically, religiously, other worldly, and so on

And also not to ignore people of older generations

This is specifically in relation to your life and the factors that have influenced it

For example, I am THE coach for recent grads and twenty-somethings who want help figuring out their career and life direction because I personally had a really messy and rough start to my twenties

Filled with friendship breakups, relationship changes, and career struggles

I found my way through and for the last 5 years have helped other twenty-somethings within the context of their life and the context of the changing world

But my story and sharing my experiences with my clients, helps them see that 1. They’re not alone and 2. I get them

So this episode is designed to explain why relatability matters way more than you might think when it comes to finding friends, developing relationships, and even seeking out support through a coach or therapist; what to look out for in terms of relatability, and what not to do when it comes to finding the people who just get it

For starters, relatability is knowing the difference between people who can sympathize and people who just get it

People who can sympathize with you is when they say something like ‘i’m sorry, that must be really hard for you’

Key words here: for you

Because they can’t personally relate to your pain, but they can see that whatever is happening in your life is causing you pain and they’re sorry that you’re experiencing pain

It’s kind and they mean well

But finding someone who can sit you down and say “I have been there, I know exactly what that feels like, and here is what helped me”

That’s someone who gets it

Who makes you feel seen and that you’re not this oddball or, dare I say, special exception? 

Which if you haven’t watched my tedx talk: you’re not special, you’re just adulting be sure to check it out in the show notes because it relates to this episode topic

But with what I was saying between a sympathizer and someone who gets it is the quality of guidance you’re about to receive 

It goes from generic and textbook to real, proven, personal, authentic

I mean think about it, if you’re a twenty-something listening and you’ve gone back and forth with your parents at any point in your twenties around job searching, I would almost guarantee you guys have butted heads

When a parent is financially involved in their kids coaching, I also meet with them twice in the 3 month partnership and I can see it for my own eyes how wrong their views are in 2026

Your parents have probably said something like: just go online and apply, you’re wasting time by not doing that

Then I come in as your coach and say that actually is a bigger waste of time and much more frustrating than expanding your network in person and online 

Going online to apply does not work for the vast majority of college grads entering the work force in the last few years

Giving someone career advice in the 1990s and in the 2020s is so different.. What worked back then does not work now

Because now we have google, ai, and less job availability all around with more applicants than ever before fighting for the same one position 

Both your parents and me, as your coach, have your best intentions at heart and want to help you get a job

Your parents just don’t understand today’s world they only understand the world from when they were in their twenties

And that makes a huge difference in your experience, and in this example, your job hunt to success timeframe

This isn’t an intelligence gap, it’s a relevance gap

It’s not a jab at older generations, it’s being realistic about this fast paced and constantly changing world

Which is why finding the people who actually share your context, your era, your specific version of navigating adulthood is one of the most important things you can do for yourself right now

And this doesn’t just apply to finding a coach or therapist who understands you, it’s people you’re interacting with on a regular basis

Yes there is value in learning from the older generations, this is more about being a twenty-something navigating today’s world

Because one of the hardest parts of your twenties is realizing that everyone is living very different lives

Someones living at home

Someone else is going to grad school

Someone else is getting married

Someone else is solo traveling

Someone else just lost their job

And in the same week someone else just got promoted

Everyone is all over the place

It’s why you might have grown apart from your high school bestie solely because you guys are on entirely different life paths

I will say my best friend Katie and I got closer when we were both figuring out our long distance relationships 

There were certain shared frustrations that only those also in a long distance relationship could understand

And I know I would have been so much more lost if I didn’t have her to talk to

Similarly, I know I definitely was very lost when I was the only one of my entire friend group to lose her job less than a year into graduating college and I was the only one in my friend group who didn’t even have a job lined up prior to graduation

And when you are the only person in your friend group who is unemployed or say single or dealing with some health problems, it can feel very isolating

Not because your friends don’t care about you or don’t want you to succeed, it’s because they don’t live where you currently live.. In this moment, moving through this experience 

People can love you and people can understand you

Sometimes those are one in the same and sometimes they operate in entirely different people

And one of the healthiest things you can learn in your twenties is know who stands where in your life, or in other words, that different people serve different purposes

And not expecting one friend, parent, sibling, partner, even therapist or coach to understand every part of your life

I will say, something I am very good at is understanding the way my clients think so when different situations arise in their life, i can help them work through it through their perspective

Regardless of whether or not I’ve also encountered something similar 

Although, I usually have encountered something similar to some extent because of how wild the first half of my twenties were across basically every area of my life

But relying on one person to be your everything: your confidant, celebrator, challenger, sound board, comfort, is a recipe for disaster 

Diversify your areas of influence and within that, know who you want advice from and who you don’t

Because I love my boyfriend, but he has no idea what it’s like to run a business so asking him for business advice would not be helpful in the slightest

His career expertise lies only in the 9-5 and he loves being a corporate cog life

Which is great for him, but not helpful for me when I have a business question

Or if you’re having trouble in your relationship, you’re probably not going to turn to your single friend because, and I’m speaking from a friend’s experience here, they have a skewed view of relationships right now

They may love you and also want a single friend to go out with 

Or they may love you and hate relationships

You want to talk to people who are on the same roadtrip with you, not the people who are in a totally different country

And I think we get ourselves into trouble because we ask the wrong people the wrong questions.

Then we’re frustrated when their answer doesn’t resonate.

But taking the road trip analogy, you need to stop asking people for directions on a road they’ve never driven on

Think about it, you wouldn’t ask someone who’s never been to Banff, Canada using that as an example since I went in July, what roads to take or trails to hike

You’d probably ask someone who went fairly recently, within the last few years

What to pack, where service drops off, what to avoid, and what you must see

In a similar sense, you’re not going to ask someone who went 15 to 20 years ago because so much has changed by then! So their reference points are practically irrelevant 

It’s the same thing with your life

Your single friend isn’t on the relationship road

Your employed friend who has never had to qualify for unemployment, doesn’t know what you need to do or the burdens you’re encountering

Your mom’s salary when she was in her twenties gives you no data points to your salary and cost of living now 

Your 9-5 friend isn’t anywhere near your road trip of entrepreneurship 

They’re just holding different maps and that’s ok

It’s up to you to find someone who is a few stops ahead of you or recently completed the road trip to help you out, point you in the right direction, give you some feedback

So if there were any actions you could take right now as you move through this next week or even month it’s this

1. Identify who your sympathizers are, like your mom for example
2. Who your “Get It” People are for your career, your relationships, and your personal growth.
3. Stop looking for people who have all the answers. Start looking for people who understand the question.

And then keep this in mind with each new life circumstance that comes your way

Because you need to find your people

The people who just get it

Where you don’t have to explain yourself

Because that is probably one of the best parts of experience camps, you can walk right up and know that everyone around you gets it

They know what unimaginable loss feels like, they are roughly around your age, and dark humor is widely accepted

I mean I found out one of my campers birthdate like the exact day and year she was born is the exact day my dad died and we got to joke about it

I was like oh my god, are you my dad reincarnated

When I told other people at camp, they immediately laughed and when I told people when I got home, they were a bit uncomfortable

So I’d add: it’s okay her dad’s dead too

I’d have to further explain the joke and that laughter is an appropriate response

That’s the difference

How you think about your life, operate in it, even joke about it, is best done in the crowd of people who also get it, have operated in it, and also joke about it

Because across different phases of your life: relatability is going to be more important than blanketed advice 

And by now you should have a pretty clear understanding as to why

So, on that note, this does conclude another episode of how to twenty-something

If you liked what you heard, learned something new, or know someone who collects advice from the wrong places, then please share this episode

Give it a 5 star rating, post it to your story, send it to a friend

Just do something to help me reach all of the twenty-somethings navigating the most confusing decade of their life

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