how to twenty-something

Jess Diamond
  • 4.9 (12)
  • 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. 1D AGO

    Ep. 152 Why skinny doesn't mean healthy

    How to Make Adulting Suck Less: https://jessdiamondcoaching.com/suck-less/ TRIGGER WARNING: Discussion of bodies, eating disorders, and skinniness, listen at your own discretion. This episode is designed to call out the problem in today’s society: the overuse and abuse of weight loss drugs and practices. We went from chasing strength to once again chasing skinny with the goal to take up less and less space. I use this episode to break down why skinny does not mean healthy, how the media is influencing your perception of your own body, and the very real difference between being naturally thin and being undernourished. I also share the actual markers of health that I use in my own life and with my clients: things like energy, strength, hormones, and your relationship with food. This is meant to be a reality check so you can stop chasing a trend and start paying attention to what your body actually needs. Because skinniness is a trend… but your health is something you have to live with for the rest of your life. Key Takeaways: Just because someone is small doesn’t mean their body is functioning wellYour body has a natural set point, and forcing it below that comes with consequencesEnergy, strength, hormones, and your relationship with food matter more than your sizeStop trying to take up less space 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

  2. MAY 4

    Ep. 151 The biggest conversations you're not having with Brittany Scantland-Lall

    How to Make Adulting Suck-Less: https://jessdiamondcoaching.com/suck-less/ Let’s face it, we’re not immortal.. There will come a day when we die. Which means it’s time to have the conversations with your loved ones about what happens to your entire belongings when that time comes. Because, yes, something could happen in this decade. We’re talking your pets, subscriptions, bank accounts, literally everything that has your footprint on it. Brittany, a Licensed Estate Planner in the State of North Carolina, helps you break down what you can do today if you don’t want to create a whole written will. Key Takeaways: What estate planning and why does it matter in your twentiesThe different types of assets you’re not thinking aboutHow this is the biggest gift you could give your loved onesEasy steps you can take today to help you plan your estateAssigning people to have access to your digital footprintYour parents are no longer defaulted on your accountsMake these decisions while you’re healthy and level-headedWhen you should think about creating or updating your estate plan Helpful Resources: Let’s chat: https://calendly.com/coach_jessdiamond/success 3 ways to stop spiraling: https://jessdiamondcoaching.com/spiral/ Email Me: coach.jessdiamond@gmail.com Contribute to an episode: https://forms.gle/QwvBrZFbZXRdCjQv9 Be a Guest: https://forms.gle/oiLVCbrydjzaK5pq5 Connect with Brittany Scantland-Lall: Instagram: https://www.instagram.com/estateplanvan/ Website: www.EstatePlanVan.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

    56 min

  3. APR 27

    Ep. 150 Everything I got wrong in my twenties

    How to Make Adulting Suck Less: https://jessdiamondcoaching.com/suck-less/ In this special 150th episode, I’m reflecting on everything I got wrong in my twenties — from my career path and health habits to dating, friendships, and self-worth. Looking back, those “wrong turns” were actually the experiences that led me exactly where I’m meant to be today. This episode is a reminder that you don’t know what you don’t know and that getting things wrong is often the very thing that helps everything work out. If you’re in your twenties and feel like you’re messing everything up, this conversation is for you. Sometimes the things that don’t work out are exactly what set your life up to work out better than you planned. Key Takeaways: The moments that feel like rejection or failure can actually lead you to better opportunities than you originally plannedDon’t let your ego stop you from asking for helpWhether it’s a college major, a job, or a relationship, choosing a different path is often a sign of growthAsking for help, setting boundaries, and choosing yourself takes strengthThe “wrong” job might be the thing that leads you to the right one.Pay attention to patterns, not promises. 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

    20 min

  4. APR 20

    Ep. 149 What is your paycheck costing you?

    How to Make Adulting Suck Less: https://jessdiamondcoaching.com/suck-less/ This episode is all about your money story: the beliefs you developed about money growing up… and how those beliefs can shape the jobs you take, the lifestyles you build, and the sacrifices you make. I challenge you to look at what your paycheck might actually be costing you from your health, to your relationships, your time, and your overall quality of life. This episode is a reminder that while money matters, it’s only one way to be rich and it’s on you to build the rest of your life around it. Key Takeaways: The way you spend, save, earn, and even talk about money usually comes from what you saw and heard growing upA big salary, nice benefits, and a respectable title can make it feel impossible to leave… Even when you're miserable.The job, apartment, travel, dinners, and subscriptions all start depending on that paycheck to existMoney isn’t helpful if you’re too burned out or sick to actually enjoy the life you're buildingFind the other ways you can be rich in your life... Outside of your paycheck 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

    17 min

  5. APR 13

    Ep. 148 The reality of being self-employed in your twenties

    Being self-employed isn’t as glamorous as social media makes it out to be. We’re talking numbers, emotions, expectations, timelines, doubts, and the grit that comes with this kind of decision. I walk you through my real income from my first job out of school through my first four years of being self-employed. I talk about the mental and emotional toll of entrepreneurship… the uncertainty, the self-discipline required, and why it’s not the “freedom” social media makes it seem. If you’re thinking about leaving your 9–5, this episode will help you decide whether you’re chasing the aesthetic… or you’re actually ready for the reality.  Key Takeaways: Expect 3–5 years of hard work before your business feels stable or sustainableSet a clear timeline and savings goal, because dreams without deadlines stay dreamsKnow your backup plan before you dive inYour money will leave your account faster than it’ll go inSocial media shows the aesthetic, not the years of survival mode underneath 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

    20 min

  6. APR 6

    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

  7. 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

  8. 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
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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
    153
  • Rating
    Explicit
  • Copyright
    © Copyright 2026 Jess Diamond
  • Show Website
    how to twenty-something