how to twenty-something

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...

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...

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 migh...

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...

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 appro...

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...

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 gho...

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...

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...

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...

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, find...

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...

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 w...

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...

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 o...

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!...

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...

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 combinat...

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. You...

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...

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...

TRIGGER WARNING: mention of assault, rape, and abuse in this episode National Domestic Violence Hotline: 800-799-7233 or text BEGIN to 88788 21 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.prettyhandshardp...

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...

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...

In this episode, I share my journey of leaving the corporate world to become self-employed at 25 and how I’ve helped other twenty-somethings do the same. I talk about the year and a half of planning that went into my transition, the challenges I faced in my first year, and the key lessons I learned along the way. We’ll explore the importance of patience, dedication, financial planning, and having...