how to twenty-something
How To Twenty Something is a career and life advice podcast for young professionals. It covers topics like career development, relationships, and health and wellness. The show aims to help listeners gain confidence, take risks, and reach their full potential.
Episodes
Ep. 166 Are you the partner you want to date?
NEW COURSE: How to Make Adulting Suck Less: https://jessdiamondcoaching.com/suck-less/Watch my TEDx Talk: https://www.youtube.com/watch?v=RE_7I6vDKrIWe spend so much time talking about what we want in a partner that we rarely stop to ask ourselves if we're showing up the same way. In this episode, I'm challenging you to hold up the mirror and take an honest look at the qualities, habits, and stand
Ep. 165 Get Unplugged: How to Break Your Phone Addiction
NEW COURSE: How to Make Adulting Suck Less: https://jessdiamondcoaching.com/suck-less/Watch my TEDx Talk: https://www.youtube.com/watch?v=RE_7I6vDKrIYour relationship to your phone is destroying your relationship to your life. From the moment you wake up to the second you fall asleep, your device has a choke hold on you and I'm getting into exactly what that is doing to your mental health, your fo
Ep. 164 When is it time to work with a coach?
NEW COURSE: How to Make Adulting Suck Less: https://jessdiamondcoaching.com/suck-less/ Watch my TEDx Talk: https://www.youtube.com/watch?v=RE_7I6vDKrI Episode SummaryHow do you know if it's actually time to work with a coach?The truth is, coaching isn't just for people whose lives are falling apart. It's for people who know they're capable of more but feel stuck figuring out how to get there. In t
Ep. 163 This is not your forever, but it is your for now
NEW COURSE: How to Make Adulting Suck Less: https://jessdiamondcoaching.com/suck-less/ Watch my TEDx Talk: https://www.youtube.com/watch?v=RE_7I6vDKrI Episode SummaryHave you ever looked at your life and thought, "I know I'm capable of more than this."Whether you're living with your parents, working a job that feels beneath your qualifications, recovering from an injury, or simply feeling like lif
Ep. 162 This is why you operate the way you do with Adrienne Craighead
Claim your free Human Design Chart before you listen: https://bit.ly/HD101-AC WATCH MY TEDX TALK: https://www.youtube.com/watch?v=RE_7I6vDKrIHuman design is the ultimate personality test. In this episode, Adrienne Craighead, not only reads my chart, but breaks down how you can read and interpret your own chart. This is super valuable for helping you make decisions that align with who you are to yo
Ep. 161 How to talk to your parents so they actually hear you
WATCH MY TEDX TALK: https://www.youtube.com/watch?v=RE_7I6vDKrINEW COURSE: How to Make Adulting Suck Less: https://jessdiamondcoaching.com/suck-less/If you have ever felt like your parents just do not hear you no matter what you say, this episode is going to help you figure out why and what to do about it. A big part of the problem is not what you are saying but the dynamic you are both unknowingl
Ep. 160 Is Gen-Z really screwed in the job market?
NEW COURSE: How to Make Adulting Suck Less: https://jessdiamondcoaching.com/suck-less/The job market is tough right now and I'm not going to sugarcoat it. In this episode I'm breaking down the real statistics behind what's happening with entry level jobs, why AI is a massive driver behind it, and whether Gen Z is actually screwed or just searching the wrong way.Spoiler: it's a little bit of both.
Ep. 159 The Psychology Behind Your Quarter Life Crisis
WATCH MY TEDX TALK: https://www.youtube.com/watch?v=RE_7I6vDKrIHow to Make Adulting Suck Less: https://jessdiamondcoaching.com/suck-less/If your twenties have felt confusing, disorienting, or like everyone else somehow got the manual you missed… this episode is for you. In today’s conversation, I break down the psychology behind the “quarter life crisis” and why so many twenty-somethings suddenly
Ep. 158 This is your sign to lift weights
NEW COURSE: How to Make Adulting Suck Less: https://jessdiamondcoaching.com/suck-less/ Watch my TEDx Talk: https://www.youtube.com/watch?v=RE_7I6vDKrI In this episode I am breaking down why your twenties are genuinely the best time to build muscle and strength, what happens to your body if you wait until your thirties to start, and why this matters just as much for your mind as it does your body.
Ep. 157 How to Stop Letting Your Mistakes Live Rent Free in Your Head
WATCH MY TEDX TALK: https://www.youtube.com/watch?v=RE_7I6vDKrIHow to Make Adulting Suck Less: https://jessdiamondcoaching.com/suck-less/If you've ever let a tiny oopsy consume your entire day, your evening, and your 2am thoughts, this one is for you. You’ll hear me share a client’s story who made her first mistake three weeks into her new job and let it ruin her whole night, and why that reaction
Ep. 156 Are you quitting or just running away?
How to Make Adulting Suck Less: https://jessdiamondcoaching.com/suck-less/ This episode discusses something that's a lot harder to figure out than it sounds: knowing whether you're strategically quitting something or just running away from it. Because on the surface they look identical, but the difference between the two will determine whether you're setting yourself up or selling yourself short.
Ep. 155 When everything falls apart at the same time
How to Make Adulting Suck Less: https://jessdiamondcoaching.com/suck-less/ This episode is all about what to do when life decides to life… and by that I mean everything falls apart all at once and you can't seem to catch your breath. The truth is, you can't hit pause on life while everything falls apart, but you can learn how to handle it without burning yourself out in the process. I break down h
Ep. 154 You did it! Now What?
How to Make Adulting Suck Less: https://jessdiamondcoaching.com/suck-less/In this episode, I'm talking about the low that follows a really big high… that "now what?" feeling that hits after you finally accomplish something you've been working toward. Whether it's landing a job, getting married, finishing a big project, or hitting a major milestone, I share why that post-achievement drop is complet
Ep. 153 The problem with always accomplishing things
How to Make Adulting Suck Less: https://jessdiamondcoaching.com/suck-less/This episode breaks down the problem with always needing to accomplish things and why getting everything done doesn’t always mean you did it well. I talk about how constantly saying yes and rushing through your life leads to mistakes, poor communication, and people feeling overlooked.It’s time to start looking at your days d
Ep. 152 Why skinny doesn't mean healthy
How to Make Adulting Suck Less: https://jessdiamondcoaching.com/suck-less/TRIGGER WARNING: Discussion of bodies, eating disorders, and skinniness, listen at your own discretion.This episode is designed to call out the problem in today’s society: the overuse and abuse of weight loss drugs and practices. We went from chasing strength to once again chasing skinny with the goal to take up less and les
Ep. 151 The biggest conversations you're not having with Brittany Scantland-Lall
How to Make Adulting Suck-Less: https://jessdiamondcoaching.com/suck-less/ Let’s face it, we’re not immortal.. There will come a day when we die. Which means it’s time to have the conversations with your loved ones about what happens to your entire belongings when that time comes. Because, yes, something could happen in this decade. We’re talking your pets, subscriptions, bank accounts, literally
Ep. 150 Everything I got wrong in my twenties
How to Make Adulting Suck Less: https://jessdiamondcoaching.com/suck-less/ In this special 150th episode, I’m reflecting on everything I got wrong in my twenties — from my career path and health habits to dating, friendships, and self-worth. Looking back, those “wrong turns” were actually the experiences that led me exactly where I’m meant to be today. This episode is a reminder that you don’t kno
Ep. 149 What is your paycheck costing you?
How to Make Adulting Suck Less: https://jessdiamondcoaching.com/suck-less/This episode is all about your money story: the beliefs you developed about money growing up… and how those beliefs can shape the jobs you take, the lifestyles you build, and the sacrifices you make. I challenge you to look at what your paycheck might actually be costing you from your health, to your relationships, your time
Ep. 148 The reality of being self-employed in your twenties
Being self-employed isn’t as glamorous as social media makes it out to be. We’re talking numbers, emotions, expectations, timelines, doubts, and the grit that comes with this kind of decision. I walk you through my real income from my first job out of school through my first four years of being self-employed. I talk about the mental and emotional toll of entrepreneurship… the uncertainty, the self
Ep. 147 Why you feel out of place in your twenties
Feeling out of place is a normal part of your twenties. From identity shifts, to unexpected setbacks, to returning home, and the quiet disorientation that comes with becoming a new version of yourself.This episode highlights the gap between expectations and reality, and what happens when your life doesn’t look how you thought it would. If you’ve been feeling unsettled, disconnected, or like you do
Ep. 146 For if you overthink what you say with Dayna Gowan
Welcome all overthinkers! This episode talks about how improv translates into the real world by inviting you to play, be silly, and create a non-judgemental space.. All of which will help you with your overthinking tendencies. Public Speaking Expert and founder of Improvly Speaking, Dayna Gowan, breaks down her relationship to Improv and how it’s made her a more confident person. We talk about the
Ep. 145 Top 10 Red Flags in Your Relationship
This episode breaks down the 10 sneaky red flags to watch out for in your relationship. Not the obvious things like cheating or abuse, but the quiet ones that don’t seem like a big deal at first but slowly change how you feel about yourself. I share personal experiences and real examples to help you see what’s actually happening behind the scenes in your relationship. If you’re looking for a sign
Ep. 144 How far should you live from work?
There’s no one “right” answer when it comes to how far you should live from work, there’s only the choice that best supports the life you’re trying to build right now. This episode breaks down the real factors that matter when deciding on a commute, from time, money, and energy to community, lifestyle, and what your priorities look like in this current season. I talk about how to survive a longer
Ep. 143 Life really does get easier
In this birthday episode, I’m reflecting on my last year in my twenties and why, despite everything I’ve been through, life really is getting easier. Not because life stops throwing curveballs, but because you get better at handling them. I talk about why your twenties feel so hard in the first place, how every experience is brand new, and why learning to recover from breakups, job loss, friendshi
Ep. 142 What your coping mechanism says about you
This episode breaks down the coping mechanisms most twenty-somethings use when life feels overwhelming and what those habits actually say about you. I run you through the top 10 coping mechanisms ranked in order from worst to healthiest while calling you out in the process. Consider this a wake up call to start paying attention to how you cope with stress, discomfort, and hard emotions so you can
Ep. 141 Why quick fixes aren't quick
This episode breaks down the quick fixes we’re constantly being sold and why they don’t actually work when it comes to obtaining results. I explain why these tactics feel productive in the moment but leave you burnt out, frustrated, and stuck long term. Think 75 Hard, going on a diet, a new workout regimen, dating apps, and online job applications.. All of these AND MORE are quick fixes. This epis
Ep. 140 Building a routine from scratch
You are nothing without a routine! This episode is all about building one up from scratch so you create one that’s actually going to work for you. From nighttime and morning routines to daily and weekly ones, as well as adapting your routine to changing schedules, how you structure your life is crucial to your success and goals. Whether you’ve never had one, the one you had fell apart, or you’ve a
Ep. 139 When You’ve Already Communicated It (and Nothing Changed)
If you’ve communicated clearly, calmly, and more than once, and nothing has changed, this episode is for you. It isn’t about learning how to communicate better in the moment; it’s about recognizing when communication stops being the problem and becomes a decision point. We’ll talk about boundaries, changing expectations, and why sometimes leaving is the answer, so you can keep the right people in
Ep. 138 You need to be more picky
This episode breaks down why being picky is not a bad thing and how this doesn’t only apply to dating. The truth is your friendships, career, and relationship with yourself all deserve the same level of discernment. This episode is about learning to communicate your needs, noticing when something never fully feels right, and giving yourself permission to walk away even when nothing is “that bad.”
Ep. 137 The fear of wasting your twenties
This episode breaks down why we all fear wasting our twenties. The pressure to travel, date, go out every weekend, and have life “figured out” can make it feel like one wrong choice will mess everything up. There are two sides I discuss when it comes to this fear: fear of missing the fun parts and fear of falling behind the milestones your peers are hitting. If you’ve ever worried that you’re behi
Ep. 136 Why more money isn't the answer
In this episode, I’m breaking down one of the biggest money myths twenty-somethings fall for: the idea that more money will magically fix your financial stress. The truth is that most of us go from living within our parents’ means to suddenly trying to replicate that same lifestyle on an entry-level salary. I walk you through why side hustles and second jobs are usually just bandaid solutions, how
Ep. 135 If you're unhappy with where you're at
This episode is for you if you’re facing a season of discontent. Whether it’s career dissatisfaction, friendship shifts, relationship anxiety, and even how the city you live in can make you feel stuck, it’s important for you to figure out what’s in your control, how to give yourself a deadline, and how to take action without burning your life down. My goal is to help you stop tolerating a life tha
Ep. 134 Rewind and reflect for what's next!
This episode guides you through a real rewind and reflection of my 2025 — the wins, the hard stuff, and how I’m using both to set more intentional goals for 2026. I share some of my biggest highlights, most painful losses, and help you pause, reflect on your own, and actually celebrate what you’ve done instead of brushing it off. I also walk you through how I’m setting goals for 2026 and share som
Ep. 133 When nothing sounds like a good idea
What happens when nothing sounds like a good idea and you feel completely stuck in your life? This episode talks about how we usually end up in one of two places: the Land of No or the Land of I Don’t Know, and how both keep us stuck even though they look different. It’s filled with real stories from my life and my clients' lives and how we’ve worked to book our one way ticket out of these lands.
Ep. 132 Why adulting is so exhausting
If you’re always tired, you’re not alone, but you also might be the reason for your exhaustion. From shorter days and less sunlight to sitting for 10 hours straight, I explain how our modern world completely goes against the natural rhythms our bodies were built for. Getting around this exhaustion looks like getting back to the basics, while also recognizing that being an adult is exhausting!Key T
Ep. 131 Prepping for an interview
In this episode, I’m walking you through everything you need to know to prep for your next interview: what to do before, during, and after. I share how to make a strong first impression, the key research steps that’ll help you stand out, and how to answer common questions without sounding rehearsed. I also talk about managing nerves and how your body language can make or break your confidence. Plu
Ep. 130 The Truth About Networking in Your Twenties with Dana Alfirevic
Networking… something we all know we need to do, yet are so turned off by the idea of small talk and dead end connections. Which is why it’s time for you to learn how to network, redefine what it means to network, and how to build meaningful professional relationships that will help you achieve your career goals. Networking is for more than when you’re looking for a job, it’s part of every relatio
Ep. 129 The Lazy Guide to Good Habits
If you’ve ever called yourself lazy or felt guilty for not having the energy to keep up with your “good habits,” this episode is for you. Laziness gets a bad rap, but what if it’s actually a sign that your brain is trying to make life easier? In this episode, I share how to use your lazy tendencies to your advantage by creating systems that remove friction, reduce decision fatigue, and make your g
Ep. 128 Stop Getting Ahead of Yourself
Show notesIf you’ve ever caught yourself spiraling about outcomes that don’t even exist yet, you’re not alone. We all want answers before they’re ready to come, but that need for control only creates more anxiety. In this episode I share why this happens, how it shows up in different parts of your life, and what to do when you find yourself jumping the gun. Key Takeaways:How your fears and im
Ep. 127 It's okay to be selfish... until it's not
In this episode, I talk about the fine line between being selfish in a healthy way… the kind that protects your energy and honors your needs and the kind that starts to isolate you or hurt the people around you.In your twenties, everyone tells you to “put yourself first,” but few people teach you what that actually looks like in practice. So today, I unpack what it means to choose yourself without
Ep. 126 Are they the one or is it time to run? with Rebecca Williams
How do you know if the person you’re with is your forever person? This episode dives into what to look for in your relationship and ends with the number one question you should ask yourself if you’re doubting your relationship’s longevity. Knowing when to walk away, how to manage conflict, what to look out for as red and green flags in your partner, and how to break the bad relationship patte
Ep. 125 What it takes to be a good friend
Friendship in your twenties is messy, complicated, and always changing. In this episode, I’m breaking down what it actually means to be a good friend and how to avoid falling into the trap of being a “shitty” one. I share my own struggles with wondering if I’m a bad friend, what reciprocity looks like, and why communication matters more than constant texting. From how you respond when someone init
Ep. 124 Your twenties are a decade of loss
No one warns you about the different types of loss that comes with growing up. It’s not all bad, but it is bittersweet. You lose old versions of yourself, friendships that don’t fit anymore, jobs that once felt stable, and even the direction you thought your life was headed in. This episode is to help you identify where you’re experiencing loss in your life and why you’re going to be confused arou
Ep. 123 How to Pivot When Life Doesn’t Go as Planned
Your twenties are basically one big pivot, so let’s talk about how to handle them without losing your mind.From careers to relationships to moving cities to changing habits, pivots never feel easy in the moment. In this episode I share some of my own pivots, stories from my clients, and why your brain freaks out every time you’re about to make a change. Most importantly, I’ll walk you through how
Ep. 122 Living With Roommates vs. Living Alone: What No One Tells You
In this episode, I’m breaking down one of the biggest living decisions you face in your twenties: should you live with roommates or live alone? I share stories from my own experience, the real pros and cons of both options, and what it takes to be a good roommate versus a bad one. Whether you’re craving independence, trying to stretch your budget, or figuring out how to not lose a friendship
Ep. 121 What's the point?
In this episode, I’m diving into the big question we all ask at some point: what’s the point? Whether it’s about college, your 9–5 job, dating, or just life in general, it’s normal to hit those crossroads where you wonder why you’re even doing what you’re doing. I talk about why this question shows up most when we’re burnt out, bored, or in a season of transition, and how you can start to uncover
Ep. 120 What no one told you about being an adult
In this episode, I’m diving into all the things no one really tells you about being an adult. I share the story of my very first “oh crap, I’m an adult” moment and how that experience set the tone for learning that adulthood is full of unexpected challenges. From jobs that don’t feel like your calling, to the struggle of making and keeping friends, to the identity shifts that make you feel out of
Ep. 119 When everyone is hanging out without you
This episode talks about the gut-punch feeling of “everyone is hanging out without me,” why it hits so hard in your twenties, and how to tell the difference between being excluded and just not being included. I share my own stories (past and very present) of feeling left out, the way our brains love to spiral into the worst-case scenario, and why social media is the absolute worst for feeding that
Ep. 118 Stuck in the in between
In this episode, I’m breaking down what it feels like to be in the in between—that frustrating, uncomfortable space where you're actively working toward your next thing but not there yet. Whether it’s a new job, a relationship, a body goal, or a big life shift, this episode is for anyone stuck in that “not quite yet” phase. I’m sharing five powerful reminders to help you stay grounded, patient, an
Ep. 117 In Your Single Era with Danielle Facchine
No, this is not your typical ‘love yourself’ kind of episode, but rather getting into the real thoughts and real emotions behind being single – the good and the bad. Danielle Facchine, founder of the Single Life Revolution, sheds light on how to keep living your life when you’re single (and why it’s the absolute best time to do so). If you’re deep in the pits of the single life and trying to claw
Ep. 116 The 5 Steps I Would Take To Land My Next Job
If I had to land a full-time job in today’s market, here are the exact five steps I’d take. In this episode, I’m sharing the strategies I wish I knew back when I was mass applying on job boards and wondering why nothing was working. I walk you through how to narrow in on the right industry for you, how to update your resume strategically, and how to actually use LinkedIn the right way. I also talk
Ep. 115 Is it time to move in together? With Mylira Green
Moving in together is a big next step for a relationship and there are so many conversations that need to be shared prior to making this decision and progressing your relationship. Which is why I brought on Mylira Green, Relationship Coach and Therapist, to highlight common pitfalls, perspectives, and insight into being confident about deciding to move in together. From finances, to chores, to exp
Ep. 114 Why every adult should go to camp
After spending a week at Experience Camps in Georgia, I’m more convinced than ever that every adult needs to go to camp. In this episode, I reflect on what it meant to step away from my daily routine, disconnect from social media, and fully immerse myself in a world built around connection, play, and presence. Whether you’re volunteering at a cause that speaks to your story or attending an adult s
Ep. 113 Everything you know about nutrition is wrong with Dee Jackson
Everything you know about nutrition is wrong! That’s why I brought on Dee Jackson to help me discuss common nutrition statements and break down the truth and the falseness behind each one. From knowing calories, to different macros, to your own habits and priorities around food, we debunk what you’ve previously seen online that probably isn’t correct. And yes, that includes salads and how they are
Ep. 112 Why are your twenties so confusing?
Show notesYour twenties can feel like one giant WTF moment—and in this episode, I unpack why that is and what to actually do about it. Throughout this episode I share my own story of thinking I had a plan only to have the rug pulled out from under me during the pandemic, why confusion is a signal to listen to, and why societal timelines are irrelevant. It’s time you learned how to shift out of con
Ep. 111 The power of attracting, not demanding with Becca Ploener
In a heavily masculine dominated world (the patriarchy), it can be really difficult for people to shift into their feminine side. The truth? We need both to create relationships and exist in this world – which brings me to the topic of attracting who and what you want; NOT demanding. This episode brings on Feminine Adventure Coach, Becca Ploener, to help you shift out of your wounded feminine and
Ep. 110 Top 5 Fitness Myths Holding You Back
In this episode, I’m diving back into the fitness world and calling out five major myths that so many of us fall for. Whether you’re a seasoned gym-goer or someone just starting out, these misconceptions can seriously mess with your mindset and your results. From thinking sweat equals a good workout to fearing that a week off the gym will erase all your progress, I’m breaking down what’s actually
Ep. 109 Breaking Off Friendships with Ciara Rubin
What are your red light, yellow light, green light moments in your friendships? This episode highlights behaviors that signify a good friendship from a bad one, how you can use this information to reflect on yourself and the friendships in your life, and what to do if you’re ready to end a friendship that isn’t working. Ciara Rubin, is a bestselling author, singer, and mystic with a mission to hel
Ep. 108 Jealousy is good for you
Jealousy is one of those emotions we all experience but rarely talk about—especially in our twenties when comparison is everywhere and progress feels like a race with no clear finish line. In this episode, I’m breaking down why jealousy isn’t a bad thing and how it can actually point you toward what matters most.This episode is meant to help you feel understood, reflect on what your jealousy might
Ep. 107 What to do With Your Money Now That You're Finally Making Some with Julia Cancro
You’ve heard the saying, “make your money work for you,” but that can mean so many different things. Author of More Than Cash, Julia Cancro, introduces the easiest ways to invest your money (in a non-scary way) so you can set yourself up for financial success - even if you feel like you’re living paycheck to paycheck. I get it, inflation makes it seem like saving money in your early-mid twenties i
Ep. 106 Navigating Your Relationship with Your Parents in Your Twenties
Whether you're super close with them, feel distant, or have complicated dynamics, your relationship to your parents is something most of us are quietly navigating. In this episode, I reflect on how these relationships evolve in our twenties and what it means to relate to our parents as adults rather than children.This conversation is meant to help you feel seen, get curious, and maybe start approa
Ep. 105 Time is on your side with Lou Smith
Time is a funny concept. We all measure it differently based on what we’re going through and what we’re seeing around us. Lou Smith went from professional basketball player to bar manager, to personal trainer, to videographer and with every pivot he made, he never felt behind. Lou exemplifies why it’s so important for you to believe that time is on your side, otherwise you risk staying stuck and u
Ep. 104 What ghosting really means
Whether you’ve been ghosted, done the ghosting (yep, I see you), or just hate how common it’s become, this episode is for you. I’m calling ghosting out for what it really is—a sign of immaturity, poor communication, and a lack of respect. And no, it’s not just a dating thing. Ghosting happens in friendships, jobs, clients—you name it, it’s everywhere.In this episode, I walk you through why we ghos
Ep. 103 If you want to make more money, do this... with Karishma Wadhwani
We all want to make money.. It’s how we’ll be able to live our lives, travel the world, create experiences, but knowing how to ask for more money requires thought, preparation, and practice. Karishma Wadhwani is a Holistic Career Coach and she breaks down exactly what you need to do and believe when it comes to creating your own opportunities (and earning more money). She emphasizes how important
Ep. 102 Why quitters sometimes win
In this episode, I’m challenging the age-old idea that “quitters never win.” Sometimes, quitting is the bravest and wisest choice you can make—and that’s exactly what I unpack in this episode of How To Twenty-Something. I talk about how quitting doesn’t always mean giving up; it can mean choosing yourself, setting boundaries, and making space for something better. As well as when to know if it’s t
Ep. 101 So you found yourself in a toxic workplace... with Dr. Kristy Taylor
If you are not happy with where you’re working, toxic or not, you need to get out! This episode brought on Career and Executive Coach, Dr. Kristy Taylor, to break down what you need to do if you find yourself in a toxic work environment. Dr. Kristy explains workplace boundaries, setting expectations you want to uphold, what to look out for in an interview to avoid a potential toxic work environmen
Ep. 100 Be YOU!
Happy 100th Episode of How To Twenty-Something!!! This episode is a full-on celebration, a reflection, and honestly, a love letter to being yourself. I’m talking about what it really means to be you—even when it feels easier to just blend in. I share how learning to own who I am has completely changed my life and how I help my clients do the same. We cover everything from ignoring the noise, findi
Ep. 99 Take the career risk with Somer Dice
People always say, ‘You’re young, take the risk,’ but what they don’t talk about is what that looks like, how you can do so, and why your twenties are THE time to take a risk in your career. This episode has a guest, Somer Dice, dive into her own left turn experiences that she has taken throughout her career. Somer explains why it’s important to focus on accruing knowledge and experience over stic
Ep. 98 The REAL reasons you procrastinate
This is NOT Your Life on 4/29: https://jessdiamondcoaching.com/noise/Procrastination isn’t just about laziness—it’s often rooted in fear of failure, perfectionism, or avoiding discomfort. In this episode, I break down why we procrastinate, how it holds us back, and what we can do to overcome it. I share personal experiences, practical strategies, and mindset shifts to help you take action, even wh
Ep. 97 Living Life on Your Own Terms with Jenna Heath
Living a life that you are proud of and happy with means living a life that is built on your own terms. We all have different views of the world and those views help us take action in the direction that works for us, but what happens when the direction you want to take is unconventional or unpopular? This episode invites on Jenna Heath to share her own experiences when it comes to taking the path
Ep. 96 Online Dating vs Organic Dating
This is NOT Your Life on 4/29: https://jessdiamondcoaching.com/noise/This episode dives into the differences between organic and online dating, exploring how mindset, expectations, and experiences vary between the two. While online dating offers convenience and clear intentions, it can also be mentally draining due to the sheer volume of options and the paradox of choice. Organic dating, on the ot
Ep. 95 Leverage Your LinkedIN with Katie McKiever
I know you probably know what LinkedIN is, but are you optimizing it’s existence to your advantage? Social Media Manager, Katie McKiever, is the guest for this episode where she fully breaks down why you should be hopping onto your LinkedIN account regularly, who you need to be connecting with, how to best set up your profile, and what content you post to showcase yourself in a professional space!
Ep. 94 Moving to a new city
Moving to a new city is scary, but it doesn’t have to be. This episode dives into the challenges and excitement of moving to a new city in your twenties. I offer practical advice on researching neighborhoods, budgeting for a move, and finding cost-effective ways to transport belongings. You’ll hear strategies for getting involved in local events, joining social groups, and adjusting your mindset f
Ep. 93 Building Your Own Identity with Aaron Gordon
How do you break down who you are in a world that is constantly trying to define you? Aaron Gordon is a twin and took over his family business, so he knows exactly what it means to build your own identity. Which is why this episode breaks down the different ways you can break your identity down until you lean into the version of yourself that you are the most proud of. Identity is a combinati
Ep. 92 What are your non-negotiables?
In this episode of How to Twenty-Something, I’m diving into the power of non-negotiables—those personal standards that shape your decisions, relationships, career, and daily life. I break down how to identify your non-negotiables, why they matter, and how they evolve over time. Whether it’s dating, friendships, or your job, having clear boundaries keeps you aligned with what truly serves you. Your
Ep. 91 Braving Through Your Twenties with Hannah Sol Marie
Being brave does not mean you are without fear, in fact it means you are filled with fear but you are able to take action despite it. This episode of How To Twenty-Something invites Hannah Sol Marie of Brave Bitches to discuss how she owned her bravery throughout her twenties. We talk about how bravery shows up, what being brave is, and all of the mindset that comes with stepping into your most br
Ep. 90 Develop Confidence In Your Twenties
Developing confidence is definitely one of those things that feels intangible or hard to come by. But here’s a secret: the most confident person you know also had to build this skill at one point in their life. During this episode, I share why confidence isn’t about being free of insecurities but rather trusting in your ability to handle challenges and take action. Together, we explore three key t
Ep. 89 The Power of Self-Defense with Elicia Ybarra
TRIGGER WARNING: mention of assault, rape, and abuse in this episodeNational Domestic Violence Hotline: 800-799-7233 or text BEGIN to 8878821 Days to Unbreakable is a 21-day women’s self-defense confidence training with video lessons, a guided workbook, practice drills, and community support. Enrollment opens March 2. Use code: HowToTwenty2026 for $50 off https://www.prettyhandshardpunch
Ep. 88 In the face of rejection
No matter how hard we try, rejection is unavoidable—it shows up in our personal lives, careers, friendships, and even the unexpected moments. In this episode, I share my own recent experiences with rejection, from professional setbacks to personal heartbreaks, and the toll it can take emotionally. But instead of wallowing, I focus on how we can recover and redirect, turning rejection into an oppor
Ep. 87 You Are Your Brand with Abbie O'Leary
SELF REFLECTION! SELF REFLECTION! SELF REFLECTION! That is the theme of this episode when it comes to building up your own personal brand. This episode talks about what you need to do, think, or become when it comes to building your brand professionally, personally, and within your own business. Branding is more than a logo, a catch phrase, and a color scheme, it’s YOU! With guest expert Abbie O’L
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