how to twenty-something

Jess Diamond
  • 4.9 (11)
  • 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. 4D AGO

    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 your inner circle and walk away from the rest. If you’ve ever felt stuck having the same conversation on repeat, this episode is for you, because at some point, it’s time to believe the behavior, not the potential. Key Takeaways: Believe the behavior not the potentialWhat boundaries you can set when you’re constantly repeating yourself and what you needSomeone can hear you, validate you, agree with you, and still choose not to changeApologies over time need actionYou’re not under-communicating, you’re overcommunicating Helpful Resources:  Let’s chat: https://calendly.com/coach_jessdiamond/success  Email me: coach.jessdiamond@gmail.com 3 Ways to maximize your 5-9 after your 9-5: https://jessdiamondcoaching.com/maximize  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

    15 min

  2. FEB 2

    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.” Because you’re not too picky.. you just have high standards, and honoring them will make your life a whole lot healthier. Key Takeaways: Being “too picky” is usually just another way of saying you finally have standardsIf someone consistently leaves you feeling drained, confused, anxious, or disappointed, it’s time to walk awayHow someone shows up early on is who they areThe wrong someone is not better than no one Helpful Resources:  Let’s chat: https://calendly.com/coach_jessdiamond/success  Email me: coach.jessdiamond@gmail.com 3 Ways to maximize your 5-9 after your 9-5: https://jessdiamondcoaching.com/maximize  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

    15 min

  3. JAN 26

    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 behind, doing something wrong, or running out of time, this episode is for you. Because changing your mind, starting over, and choosing what feels aligned isn’t wasting your twenties, and this episode breaks down why. Key Takeaways: The fear of wasting your twenties usually shows up in two ways: having fun and hitting milestonesThere is no universal blueprint for how your twenties are supposed to lookComparison will always make it feel like everyone else is aheadThe only real way to waste your twenties is by staying in situations that no longer serve you because you’re afraid to start over. Helpful Resources:  Let’s chat: https://calendly.com/coach_jessdiamond/success  Email me: coach.jessdiamond@gmail.com 3 Ways to maximize your 5-9 after your 9-5: https://jessdiamondcoaching.com/maximize  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

  4. JAN 19

    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 more income actually magnifies your spending habits, and what it looks like to finally live within your means instead of someone else’s. If you feel like you’re scraping by and don’t want to give up all of your favorite things, then this episode is for you. Key Takeaways: If your spending isn’t intentional now, a bigger paycheck will only magnify what’s already happeningYou need to know your real monthly expenses—rent, utilities, groceries, subscriptions, everythingChoose 3–5 things you’re unwilling to give up, and allocate money toward them intentionally instead of impulsivelyYour early twenties are financially unfair.When you build a realistic foundation that matches your income, that’s when making more money actually starts to help. Helpful Resources:  Let’s chat: https://calendly.com/coach_jessdiamond/success  Email me: coach.jessdiamond@gmail.com 3 Ways to maximize your 5-9 after your 9-5: https://jessdiamondcoaching.com/maximize  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

    14 min

  5. JAN 12

    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 that feels “meh” and start recognizing unhappiness as a sign that it’s time to make changes in your life.  Key Takeaways: A deadline can help you stop tolerating situations you’ve been settling forThere are always more options than the extreme ones your brain offersNothing changes until you get honest about what is in your control.The three questions to ask yourself when it comes to becoming happierYou are only in control of yourself: your own actions and reactions Helpful Resources:  Let’s chat: https://calendly.com/coach_jessdiamond/success  Email me: coach.jessdiamond@gmail.com 3 Ways to maximize your 5-9 after your 9-5: https://jessdiamondcoaching.com/maximize  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

    16 min

  6. JAN 5

    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 some pretty exciting announcements about what’s coming next (including my first ever TEDx Talk). My hope is that this episode helps you reflect with honesty, get clear on what you want, and feel excited about the version of you you’re walking into this year. Key Takeaways: Walking away doesn’t mean you failedWhy you need to look back before you can look aheadWhere most people mess up when setting new years resolutionsThe different types of reflectionsHow to set yourself up for the year ahead Helpful Resources:  Let’s chat: https://calendly.com/coach_jessdiamond/success  Email me: coach.jessdiamond@gmail.com 3 Ways to maximize your 5-9 after your 9-5: https://jessdiamondcoaching.com/maximize  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

  7. 12/29/2025

    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. If you feel like you’ve been the mayor of either land, this episode will help you start building momentum again and finding your way out. Key Takeaways: The Land of No shows up when you reject every idea immediately because you’re trying to protect yourself from disappointment or failure.The Land of I Don’t Know disguises itself as overthinking, caution, or being “open-minded,” when it’s really fear of choosing wrongHow being in a funk can keep you in your respective landThe tiny actions you can take today to find your way out of your land. Helpful Resources:  Let’s chat: https://calendly.com/coach_jessdiamond/success  Email me: coach.jessdiamond@gmail.com 3 Ways to maximize your 5-9 after your 9-5: https://jessdiamondcoaching.com/maximize  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

    16 min

  8. 12/22/2025

    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 Takeaways: Inheriting all of the responsibilities once held by your parents means all of the mental load falls on youOur society expects consistent productivity year-round, but humans were designed to ebb and flow with the seasonsSitting all day tells your body it only needs enough energy to sit — which is why you feel wiped out after workEveryone’s tired, but if you want to feel less drained, you have to master the basics: sleep, nutrition, and movement. Helpful Resources:  Let’s chat: https://calendly.com/coach_jessdiamond/success  Email me: coach.jessdiamond@gmail.com 3 Ways to maximize your 5-9 after your 9-5: https://jessdiamondcoaching.com/maximize  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

    15 min
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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 - 2026
  • Episodes
    140
  • Rating
    Explicit
  • Copyright
    © Copyright 2026 Jess Diamond
  • Show Website
    how to twenty-something