how to twenty-something

Jess Diamond
  • 4.9 (10)
  • SELF-IMPROVEMENT
  • UPDATED WEEKLY

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.

  1. 5H AGO

    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 over dirty dishes, this episode will help you think about what living situation makes sense for you in this season of life. Key Takeaways: Living with roommates can save money and provide built-in companionshipLiving alone gives you total freedom, peace, and control over your environment, but comes at a priceA good roommate communicates, respects boundaries, and follows through on shared responsibilities; a bad roommate does the opposite.Safety and lifestyle matter as much as finances – know whether you thrive in companionship or solitudeYou can change your mind multiple times over between living alone or with other people Helpful Resources:  Let’s chat: https://calendly.com/coach_jessdiamond/success  Email me: coach.jessdiamond@gmail.com 3 Ways to walk in a room with confidence: jessdiamondcoaching.com/confidence Contribute to an episode: https://forms.gle/QwvBrZFbZXRdCjQv9  Be a Guest: https://forms.gle/oiLVCbrydjzaK5pq5  Music: Hide and Seek by Free Music https://soundcloud.com/fm_freemusic  Music Promoted by https://www.free-stock-music.com Creative Commons/Attribution 3.0 Unported License (CC BY 3.0) https://creativecommons.org/licenses/by/3.0/deed.en_US

    17 min

  2. OCT 6

    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 your own reasons for showing up. By the end of this episode, you’ll have tools to figure out your “why,” decide who you’re really showing up for, and remember that your point is going to continue to change. Key Takeaways: Understanding why the question ‘what’s the point?’ comes up so often in your twenties“Finding your point” doesn’t have to mean discovering your life’s purposeYou have control over your point and uncovering what that means to you Helpful Resources:  Let’s chat: https://calendly.com/coach_jessdiamond/success  Email me: coach.jessdiamond@gmail.com 3 Ways to walk in a room with confidence: jessdiamondcoaching.com/confidence Contribute to an episode: https://forms.gle/QwvBrZFbZXRdCjQv9  Be a Guest: https://forms.gle/oiLVCbrydjzaK5pq5  Music: Hide and Seek by Free Music https://soundcloud.com/fm_freemusic  Music Promoted by https://www.free-stock-music.com Creative Commons/Attribution 3.0 Unported License (CC BY 3.0) https://creativecommons.org/licenses/by/3.0/deed.en_US

    13 min

  3. SEP 29

    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 place, I cover the hidden parts of your twenties that no one prepares you for. Adulthood comes with a lot of responsibility, but also the power to create the life you want for yourself, and this episode breaks down all the secrets and steps that no one tells you about.  Key Takeaways: Your first full-time job is more about learning how to work than finding your life’s callingAdulthood is full of unexpected crises, and part of the job is learning what you can and can’t controlJob loss, quitting, or career pivots are common in your twentiesMaking and keeping friends as an adult takes far more effort than it did in school or collegeFeeling out of place and questioning your path is normalYou’re responsible for your life and future Helpful Resources:  Let’s chat: https://calendly.com/coach_jessdiamond/success  Email me: coach.jessdiamond@gmail.com 3 Ways to walk in a room with confidence: jessdiamondcoaching.com/confidence Contribute to an episode: https://forms.gle/QwvBrZFbZXRdCjQv9  Be a Guest: https://forms.gle/oiLVCbrydjzaK5pq5  Music: Hide and Seek by Free Music https://soundcloud.com/fm_freemusic  Music Promoted by https://www.free-stock-music.com Creative Commons/Attribution 3.0 Unported License (CC BY 3.0) https://creativecommons.org/licenses/by/3.0/deed.en_US

    18 min

  4. SEP 22

    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 narrative. We’ll dig into how to stick to the facts, communicate what you need without playing the blame game, and create connections for yourself instead of waiting for someone to hand you an invite. So if you’re tired of feeling left out and letting your spiraling thoughts take over, this episode is for you. Key Takeaways: The difference between being excluded and not being includedUnderstanding friendship cycles as you move through your twentiesWhy social media isn’t the mind-numbing resource you think it isWays to communicate your feelings without sounding accusatoryWhy it’s usually not about youStop waiting for the invite, create the event Helpful Resources:  It's Me, I'm the Problem 9/22: https://jessdiamondcoaching.com/problem/ Let’s chat: https://calendly.com/coach_jessdiamond/success  Email me: coach.jessdiamond@gmail.com 3 Ways to walk in a room with confidence: jessdiamondcoaching.com/confidence Contribute to an episode: https://forms.gle/QwvBrZFbZXRdCjQv9  Be a Guest: https://forms.gle/oiLVCbrydjzaK5pq5  Music: Hide and Seek by Free Music https://soundcloud.com/fm_freemusic  Music Promoted by https://www.free-stock-music.com Creative Commons/Attribution 3.0 Unported License (CC BY 3.0) https://creativecommons.org/licenses/by/3.0/deed.en_US

    20 min

  5. SEP 15

    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, and hopeful as you bridge the gap between where you’ve been and where you’re going. I talk about why it’s so tempting to put your happiness on hold, how to actually measure your progress in the meantime, and what it means to reshape your identity before you arrive at your next milestone. Key Takeaways: You’re going to encounter multiple different in between moments as you grow through your twentiesWhy “it’s not forever, it’s for now” is the most powerful motto to adoptUse this time to prepare, plan, and gather the tools you’ll need for your next moveHave an end date to getting out of the in betweenClaim who you’re becoming, not where you’re currently at Helpful Resources:  It's Me, I'm the Problem 9/22: https://jessdiamondcoaching.com/problem/ Let’s chat: https://calendly.com/coach_jessdiamond/success  Email me: coach.jessdiamond@gmail.com Contribute to an episode: https://forms.gle/QwvBrZFbZXRdCjQv9  Be a Guest: https://forms.gle/oiLVCbrydjzaK5pq5  Music: Hide and Seek by Free Music https://soundcloud.com/fm_freemusic  Music Promoted by https://www.free-stock-music.com Creative Commons/Attribution 3.0 Unported License (CC BY 3.0) https://creativecommons.org/licenses/by/3.0/deed.en_US

    22 min

  6. SEP 8

    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 your way out, it’s time for you to learn how to be okay with being single in this current era of your life, why rushing to get into a relationship will not solve all your problems, and how your happiness doesn’t go on pause just because you don’t have that special someone to make memories with.  Key Takeaways: Why it’s so important to spend time being single in your twentiesHow to get over the feeling of being behindWanting a relationship vs no longer wanting to be singleBeing in a relationship will not magically solve all your problemsGo to things by yourself, even if it’s uncomfortable Your happiness is your responsibility Find reasons to celebrate yourself The level of abundance that comes with singleness Helpful Resources:  It's Me, I'm the Problem 9/22: https://jessdiamondcoaching.com/problem/ Let’s chat: https://calendly.com/coach_jessdiamond/success  Email Me: coach.jessdiamond@gmail.com Contribute to an episode: https://forms.gle/QwvBrZFbZXRdCjQv9  Be a Guest: https://forms.gle/oiLVCbrydjzaK5pq5  Connect with Danielle Facchine: Website: www.daniellefacchine.com  Instagram: https://www.instagram.com/danielle_facchine/  Email: danielle@daniellefacchine.com  Music: Hide and Seek by Free Music https://soundcloud.com/fm_freemusic  Music Promoted by https://www.free-stock-music.com Creative Commons/Attribution 3.0 Unported License (CC BY 3.0) https://creativecommons.org/licenses/by/3.0/deed.en_US

    58 min

  7. SEP 1

    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 about building real relationships, both online and in person, and why following up might be the one thing you’re not doing that’s holding you back. Whether you're a fresh grad, switching industries, or just feeling stuck, I break it all down in a way that’s actionable, honest, and rooted in what’s actually working right now.  Key Takeaways: Submitting mass applications online is often a waste of timeIdentify your strengths and interests, not just your degreeBuilding connections and relationships everywhere will serve you in the long runNetworking doesn’t only happen at “networking events”Follow up, Follow up, Follow up Helpful Resources:  Let’s chat: https://calendly.com/coach_jessdiamond/success  Email me: coach.jessdiamond@gmail.com 3 Ways to walk in a room with confidence: jessdiamondcoaching.com/confidence Contribute to an episode: https://forms.gle/QwvBrZFbZXRdCjQv9  Be a Guest: https://forms.gle/oiLVCbrydjzaK5pq5  Music: Hide and Seek by Free Music https://soundcloud.com/fm_freemusic  Music Promoted by https://www.free-stock-music.com Creative Commons/Attribution 3.0 Unported License (CC BY 3.0) https://creativecommons.org/licenses/by/3.0/deed.en_US

    19 min

  8. AUG 25

    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 expectations, and keeping the spark alive in your relationship, there are so many important conversations you need to have, and factors to consider, that will keep peace in the household and your relationship healthy - whether this is the person you end up marrying or not. Key Takeaways: Are you moving in together out of convenience or because it’s the next right step?The difference between a roommate and a romantic partnerHow and why to have the money talk… repeatedly Common conversations that MUST be had when you move in togetherIt’s healthy and highly recommended to have regular check insSetting shared expectations across an array of subjectsHow to use your love language to pour into one anotherWhat being intentional looks like now that you’ve moved in togetherSigns you have a strong foundation in your relationship Helpful Resources:  Let’s chat: https://calendly.com/coach_jessdiamond/success  Walk into any room with confidence: https://jessdiamondcoaching.com/confidence/  Email Me: coach.jessdiamond@gmail.com Contribute to an episode: https://forms.gle/QwvBrZFbZXRdCjQv9  Be a Guest: https://forms.gle/oiLVCbrydjzaK5pq5  Connect with Mylira Green: Website: www.myliratransforms.com  Music: Hide and Seek by Free Music https://soundcloud.com/fm_freemusic  Music Promoted by https://www.free-stock-music.com Creative Commons/Attribution 3.0 Unported License (CC BY 3.0) https://creativecommons.org/licenses/by/3.0/deed.en_US

    57 min
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Ratings & Reviews

4.9
out of 5
10 Ratings

About

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.

Information

  • Creator
    Jess Diamond
  • Years Active
    2023 - 2025
  • Episodes
    123
  • Rating
    Explicit
  • Copyright
    © Copyright 2025 Jess Diamond
  • Show Website
    how to twenty-something