how to twenty-something

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...

Have you ever thought about leaving your belongings and life behind to become a travel nomad? I know I have and this episode of How To Twenty-Something brings on Liz Erhartic to talk about how she’s set herself up to leave the corporate life behind and become location free. Not only does she share her strategy for making this possible, but she also shares her fears, limiting beliefs, and best sust...

Despite living in a world designed for connection, many of us feel more isolated than we ever imagined, especially during a decade full of transitions. In this episode, I share my personal experiences with loneliness, from friendship breakups to navigating life in a new city, and explore how these feelings often stem from a lack of meaningful connections. Together, we’ll identify the signs of lone...

From door to door sales, to logistics and cold calling, to advertisement, to procurement analyst, to taking a 3 month hiatus in Alaska, Orien has had quite the career path and is currently back on the job market after returning to North Carolina. Much like other twenty-somethings, Orien is struggling to land his next role so we used this episode of How to Twenty-something to help him confidently s...

Your career impacts every aspect of your life, and it’s crucial to make moves that align with your values while embracing the flexibility and risks unique to your twenties. This episode is designed to help you feel better about job hopping, the decisions you’re making in your career, and how to know if it’s time to change jobs so you do know where your career is going. Wherever you’re at in your c...

What you believe to be true, will become the truth for you. This episode of How To Twenty-Something invites on High Performance Coach, Corinne Eckert, to discuss how your identity and belief system can either propel you forward or keep you stuck. Throughout this episode we dive into how your own beliefs determine your outcomes and what is possible for you, your self talk if you are a people please...

In this episode of How to Twenty-Something, I explore the importance of becoming decisive and how it can transform your twenties. I share practical tips, like starting with low-stakes decisions to build your decision-making muscles. I explain how indecisiveness often stems from the fear of the unknown and how it can lead to missed opportunities and unmet needs. By aligning your choices with your v...

There are so many changes and transitions that happen in your twenties, most of which take a toll on your mental health. So this episode invites Dr. Lauren Chase to discuss mental health practices, defining what self care really is, common threats to your mental health, positive outcomes as a result of improving your mental health, and how boundaries are the most important skill you can learn to p...

In this episode of How to Twenty-Something , I dive into the realities of being single at weddings. As someone who’s often flown solo to weddings, I get into the highs and lows that come with it. From setting boundaries, like declining invites if you're struggling with being single, to budgeting hacks that make attending weddings a little easier, I share my personal experiences and tips. I also ta...