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. 3D AGO

    Ep. 147 Why you feel out of place in your twenties

    Feeling out of place is a normal part of your twenties. From identity shifts, to unexpected setbacks, to returning home, and the quiet disorientation that comes with becoming a new version of yourself.This episode highlights the gap between expectations and reality, and what happens when your life doesn’t look how you thought it would. If you’ve been feeling unsettled, disconnected, or like you don’t quite fit in your own life right now, this one’s for you. Key Takeaways: Feeling out of place doesn’t mean you’re failing, it means you’re in transitionReturning home, experiencing setbacks, or changing life direction can all create internal disorientationYou can’t fix internal transitions with impulsive external decisionsTransitions are supposed to feel unstable Helpful Resources:  Let’s chat: https://calendly.com/coach_jessdiamond/success  Email me: coach.jessdiamond@gmail.com How to stop spiraling:https://jessdiamondcoaching.com/spiral/  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

  2. MAR 30

    Ep. 146 For if you overthink what you say with Dayna Gowan

    Welcome all overthinkers! This episode talks about how improv translates into the real world by inviting you to play, be silly, and create a non-judgemental space.. All of which will help you with your overthinking tendencies. Public Speaking Expert and founder of Improvly Speaking, Dayna Gowan, breaks down her relationship to Improv and how it’s made her a more confident person. We talk about the power of “Yes And,” what happens if you make a mistake, and why being present is the best way to get out of your own head. If you’re like me and are burdened with overthinking what you say, this episode is for you! Key Takeaways: The most important improv skills that carries over to real lifeWhat you can do to improve your workplace comfortability and cultureWhat to do if you’re overthinking what you saidWhy you don’t need to take an improv class to be an improviser The power of “Yes And”How to take off the jacket of judgement Helpful Resources: Let’s chat: https://calendly.com/coach_jessdiamond/success 3 Ways to maximize your 5-9 after your 9-5: https://jessdiamondcoaching.com/maximize Email Me: coach.jessdiamond@gmail.com Contribute to an episode: https://forms.gle/QwvBrZFbZXRdCjQv9 Be a Guest: https://forms.gle/oiLVCbrydjzaK5pq5 Connect with Dayna Gowan: Instagram: https://www.instagram.com/improvlyspeaking/ LinkedIn: https://www.linkedin.com/in/daynagowan/ Website: improvlyspeaking.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

    55 min

  3. MAR 23

    Ep. 145 Top 10 Red Flags in Your Relationship

    This episode breaks down the 10 sneaky red flags to watch out for in your relationship. Not the obvious things like cheating or abuse, but the quiet ones that don’t seem like a big deal at first but slowly change how you feel about yourself. I share personal experiences and real examples to help you see what’s actually happening behind the scenes in your relationship. If you’re looking for a sign to stay or leave your partner, this episode is for you. Key Takeaways: The person you date will determine how you feel about yourself and your lifeSubtle red flags are often more dangerous than obvious onesConsistency matters more than apologiesRepeated patterns are information, regardless of the reason behind their behaviorYou don’t need proof something is “bad enough” to leave Helpful Resources:  Let’s chat: https://calendly.com/coach_jessdiamond/success  Email me: coach.jessdiamond@gmail.com How to stop spiraling:https://jessdiamondcoaching.com/spiral/  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

    21 min

  4. MAR 16

    Ep. 144 How far should you live from work?

    There’s no one “right” answer when it comes to how far you should live from work, there’s only the choice that best supports the life you’re trying to build right now. This episode breaks down the real factors that matter when deciding on a commute, from time, money, and energy to community, lifestyle, and what your priorities look like in this current season. I talk about how to survive a longer commute if you choose one, when a commute becomes a problem, and why optimizing your entire life around a job you won’t have forever can backfire. You’ll walk away knowing your number, what trade-offs you’re actually making, and how to decide where to live based on work, play, and everything in between. Key Takeaways: Your commute impacts more than time; it affects your energy, money, mood, and how much life you actually have after work.Choosing where you live based on lifestyle and community can matter more than weekday convenience, especially in your early twentiesIf you choose a longer commute, you need to work with traffic patterns Write down your priorities for this season of life, and make a decision that supports them 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

    15 min

  5. MAR 9

    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

  6. 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

  7. 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

  8. 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
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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
    148
  • Rating
    Explicit
  • Copyright
    © Copyright 2026 Jess Diamond
  • Show Website
    how to twenty-something