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. 143 Life really does get easier

    In this birthday episode, I’m reflecting on my last year in my twenties and why, despite everything I’ve been through, life really is getting easier. Not because life stops throwing curveballs, but because you get better at handling them. I talk about why your twenties feel so hard in the first place, how every experience is brand new, and why learning to recover from breakups, job loss, friendship changes, and identity shifts on your own is so overwhelming. Key Takeaways: Life doesn’t get easier because problems stop… it gets easier because you trust yourself to handle themYour twenties feel so hard because everything is new A lot of growth comes from experiences you didn’t ask forAs you get older, you stop taking everything so personally and start separating situations from your worth Helpful Resources:  Let’s chat: https://calendly.com/coach_jessdiamond/success  Email me: coach.jessdiamond@gmail.com Tedx Tickets March 28th: tedxsugarcreekwomen.com  Use code: VIP25 at checkout 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

    12 min

  2. MAR 2

    Ep. 142 What your coping mechanism says about you

    This episode breaks down the coping mechanisms most twenty-somethings use when life feels overwhelming and what those habits actually say about you. I run you through the top 10 coping mechanisms ranked in order from worst to healthiest while calling you out in the process. Consider this a wake up call to start paying attention to how you cope with stress, discomfort, and hard emotions so you can begin replacing the habits that hurt you with ones that actually help. Key Takeaways: Coping mechanisms are not necessarily good or bad, they are survival tools you picked up for a reasonEveryone has coping mechanisms, whether they realize it or notThe habits you reach for under stress say a lot about what you are avoiding or soothing.You cannot eliminate a coping mechanism without replacing it with something elseSome coping mechanisms look productive or healthy but still keep you stuck Helpful Resources:  Let’s chat: https://calendly.com/coach_jessdiamond/success  Email me: coach.jessdiamond@gmail.com Tedx Tickets March 28th: tedxsugarcreekwomen.com  Use code: VIP25 at checkout 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

    19 min

  3. FEB 23

    Ep. 141 Why quick fixes aren't quick

    This episode breaks down the quick fixes we’re constantly being sold and why they don’t actually work when it comes to obtaining results. I explain why these tactics feel productive in the moment but leave you burnt out, frustrated, and stuck long term. Think 75 Hard, going on a diet, a new workout regimen, dating apps, and online job applications.. All of these AND MORE are quick fixes. This episode is your wake-up call to stop searching for the fastest way out and start building routines, systems, and habits you can actually maintain. Because if it’s something you can’t do on your worst week, it’s probably a quick fix. Key Takeaways: Quick fixes gives you results right away, but will not lead you to your goalsIf something promises results without requiring skill, structure, or consistency, it’s not sustainableQuick fixes help you feel better right now while keeping you stuck long termIf it’s something you can’t do on your worst week, it’s not your long-term solution. 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

  4. FEB 16

    Ep. 140 Building a routine from scratch

    You are nothing without a routine! This episode is all about building one up from scratch so you create one that’s actually going to work for you. From nighttime and morning routines to daily and weekly ones, as well as adapting your routine to changing schedules, how you structure your life is crucial to your success and goals. Whether you’ve never had one, the one you had fell apart, or you’ve always resisted routines altogether, it’s time to build up a realistic schedule that takes you out of overwhelm and chaos and into a place of control. Key Takeaways: Your nighttime routine is more important than your morning routineThere are different ways to a create a routine that doesn’t leave you feeling trappedRoutine helps with decision fatigueAssigning tasks to specific days helps prevent procrastination You don’t need to remember everything - write it down as a list! 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

  5. FEB 9

    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

  6. 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

  7. 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

  8. 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
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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
    144
  • Rating
    Explicit
  • Copyright
    © Copyright 2026 Jess Diamond
  • Show Website
    how to twenty-something