Jess Diamond

how to twenty-something

How To Twenty Something teaches young professionals how to “adult” across various aspects of their lives from career, to relationships, to overall health and wellness, so they can gain the confidence to take risks and try new things, helping them to reach their full potential.

Author

Jess Diamond

Category

Education

Latest episode

Jul 6, 2026

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Episodes

Ep. 85 Living location free to travel the world with Liz Erhartic 27.01.2025

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...

Ep. 84 The Loneliness Epidemic 20.01.2025

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...

Ep. 83 Speaking to Your Strengths: LIVE Coaching Call with Orien Dalton 13.01.2025

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...

Ep. 82 Where is your career going? 06.01.2025

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...

Ep. 81 What it takes to reach your full potential with Corinne Eckert 30.12.2024

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...

Ep. 80 Becoming Decisive 23.12.2024

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...

Ep. 79 Mental Health in Your Twenties with Dr. Lauren Chase 16.12.2024

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...

Ep. 78 Flying Solo at Weddings 09.12.2024

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...

Ep. 77 Breaking Relationship Patterns with Adele Currin 02.12.2024

Do you find yourself trapped in your relationships or constantly attracting the ‘wrong’ person to your life? Well this episode of How To Twenty-Something breaks down your patterns and ways you can focus on improving yourself so you can improve your relationships. Relationship Coach, Adele Currin, helps her clients develop the skills needed to have healthy relationships and explains that you need t...

Ep. 76 Overcoming Imposter Syndrome 25.11.2024

This episode of How To Twenty-Something talks about the complex world of imposter syndrome—how it shows up in our careers, relationships, and daily lives, especially in our twenties. Imposter syndrome, the persistent doubt in our abilities and the fear of being exposed as a “fraud,” is so common during this period because of all the new transitions and challenges we face. In the episode I shared h...

Ep. 75 When is it good to add weight with Jake Packett 18.11.2024

This episode of How To Twenty-Something talks about why it’s good to add weight to the bar when you’re in the gym and muscle to your body. Jake Packett and I debunk common fears around the gym, how to add healthy weight to your body, defining what it really means to eat clean, and how to remove the ‘noise’ of the people who have unearned superpowers. At the end of the day, we don’t want you to fea...

Ep. 74 Burnout: Prevention & Relief 11.11.2024

This episode of How To Twenty-Something encompasses the root causes of burnout and its impact on different aspects of life—whether it’s careers, relationships, health, or the pressures of life in your twenties. I explain that burnout often stems from poor time management, lack of boundaries, and insufficient planning, all of which can be overwhelming when juggling new responsibilities. I offer act...

Ep. 73 Developing Reciprocity in Your Relationships with Melinda Rae 04.11.2024

Having reciprocity in your relationships means you are showing up and pouring yourself into another person while also receiving the same in return; it’s reaching an equilibrium. This episode of How To Twenty-Something brings on Melinda Rae to discuss how she transformed her relationships by prioritizing reciprocity and certain negotiables that helps her feel free and alive. During this episode Mel...

Ep. 72 Living in the moment vs Planning for the future 28.10.2024

In this episode, I dive into the delicate balance between living in the moment and planning for your future. I firmly believe it's not only possible but crucial to do both. I introduce my concept of "thinking with your future self in mind" and explain how this mindset can transform your daily decisions. We explore the benefits of being present, like reduced stress and increased happiness, while al...

Ep. 71 How's your anxiety? With Morgan Pambianco 21.10.2024

This episode of how to twenty-something invites on Anxiety Coach, Morgan Pambianco, to discuss dealing with anxiety throughout your twenties. Her own story of being hospitalized for panic attacks when she was 23 inspired her career change to help others who are going through their own anxiety battles. Using her message, 1% better, Morgan shares invaluable insight into how you can overcome your own...

Ep. 70 Dealing With Life Changes 14.10.2024

This episode explores the challenges of navigating life changes in your twenties, emphasizing that change is inevitable and crucial for personal growth. I help you distinguish changes that you choose and those that happen unexpectedly, offer strategies to approach both types effectively in the form of question asking, and taking control over your response to change. The episode stresses the import...

Ep. 69 What it takes to be an entrepreneur with Transformational Business and Life Coach, Stacey Brass-Russell 07.10.2024

Ever thought about ditching the corporate world for your own business, but maybe you don’t know where to start or what it takes? Well this episode of How To Twenty-Something invites on an extremely successful entrepreneur (and my business coach), Stacey Brass-Russell. Throughout this episode we talk about mindset, building your team, order of operations, common mishaps to avoid, and how to sc...

Ep. 68 Stop Should-ing All Over Yourself 30.09.2024

In this episode of "How to Twenty-Something," I address the common issue of "shoulding" on ourselves – the tendency to set unrealistic expectations based on societal pressures or comparisons to others. I discuss how this mindset can lead to feelings of inadequacy, stress, and low self-esteem. Throughout the episode, I offer strategies to reframe these thoughts and focus on personal growth and indi...

Ep. 67 Do you want to go back to school? with Carlos Piedrahita 23.09.2024

Going back to school is a common thought amongst people in their twenties, but I’m here to tell you that this decision is not for everyone! In this episode, I brought on Carlos Piedrahita, rising second year at Harvard Business School pursuing his MBA, to talk about his experience and decision around going back to school. Whether it’s to pivot careers, further your current one, or expand your netw...

Ep. 66 Top 5 Shared Experiences in Your Twenties 16.09.2024

FIND MY FRIENDS WORKSHOP on 9/25: https://jessdiamondcoaching.com/friends/   This episode explores the common shared experiences either I've gone through in my twenties or have seen my friends, family members or clients go through. This topic aims to normalize the uncertainties and challenges of this formative decade, covering topics like losing your job, going through a breakup, navigating c...

Ep. 65 Be the leader of your life with Laurie Schible 09.09.2024

This episode brings on guest expert, Laurie Schible, to talk about stepping into the leadership role that your life demands. Throughout this conversation, Leadership Coach Laurie, shares her insight on what it takes to own your life and how your decisions, core values, thoughts, and responsibilities all come together to help you be the leader of your life. Gone are the days of sticking to the stat...

Ep. 64 Your Sneakiest Fear: The Fear of Success 02.09.2024

In this episode of "How to Twenty-Something," I introduce the sneakiest fear of all: the fear of success, also known as achievemephobia. I further explain where the anxiety around success comes from which is usually accompanied with additional changes, responsibilities, and unknowns that freak your brain out. This fear is relevant in any area of your life, which I identify throughout the episode f...

Ep. 63 Giving Back (Volunteering at Experience Camps) with Justin Weidenfeld 26.08.2024

WARNING: MENTION OF DEATH AND SUICIDE, please consult a mental health specialist before listening to this episode if you suffer with any mental illnesses.  I took a week at the end of July to volunteer my time with Experience Camps, a nonprofit organization that sends kids who have lost a parent, sibling, or primary caregiver to a one-week free overnight camp. This episode is to bring to ligh...

Ep. 62 Being an introvert in an extroverted world 19.08.2024

In this episode of "How to Twenty-Something," I dive into the dynamic between introverts and extroverts in a world largely designed for extroverts. I discuss the unique challenges we introverts face in social and professional settings, offering strategies for navigating an extroverted world while honoring our needs. Key topics include understanding the core differences between introverts and extro...

Ep. 61 Buying Your First Home with Julia Watkins 12.08.2024

You’re probably going to buy your first home in your twenties, if not early thirties, so you might as well become familiar with the process earlier rather than later. This episode of How To Twenty-Something invites Julia Watkins, Realtor, to break down what exactly goes into buying your first home. We discuss what to look out for, how to handle the inspection, how much money you should have going...

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