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. 4d ago

    Ep. 157 How to Stop Letting Your Mistakes Live Rent Free in Your Head

    WATCH MY TEDX TALK: https://www.youtube.com/watch?v=RE_7I6vDKrI How to Make Adulting Suck Less: https://jessdiamondcoaching.com/suck-less/ If you've ever let a tiny oopsy consume your entire day, your evening, and your 2am thoughts, this one is for you. You’ll hear me share a client’s story who made her first mistake three weeks into her new job and let it ruin her whole night, and why that reaction is so much more common than you think. The problem isn't the mistake itself, it's that you start tying it to your worth as a person and suddenly you're not someone who made a mistake, you're convinced you are the mistake. It’s time to learn how to not dwell on this mistake for longer than you need to. Key Takeaways: Making mistakes is the most human thing you could doWhat are you making this mistake mean about you or your capabilities?How to not let imposter syndrome convince you you’re not good enoughStop over apologizingFix what you can fix, learn what you can learn, and then let it goThe goal is never to never make a mistake again, it’s to react better Helpful Resources: How to stop spiraling: https://jessdiamondcoaching.com/spiral/ 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

    13 min

  2. Jun 8

    Ep. 156 Are you quitting or just running away?

    How to Make Adulting Suck Less: https://jessdiamondcoaching.com/suck-less/ This episode discusses something that's a lot harder to figure out than it sounds: knowing whether you're strategically quitting something or just running away from it. Because on the surface they look identical, but the difference between the two will determine whether you're setting yourself up or selling yourself short. If you've ever had the itch to leave a job, a relationship, school, or any kind of commitment the second it gets hard, this one is for you. Key Takeaways: Quitting and running away look identical on the outside but the difference lies in the why behind the decisionRunning away doesn't make the problem disappear, it just delays it and guarantees it shows up againThere's a big difference between making a decision and having a reaction Staying somewhere longer than you want to can actually set you up for a much smoother transition into what's next Helpful Resources: How to stop spiraling: https://jessdiamondcoaching.com/spiral/ 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

    17 min

  3. Jun 1

    Ep. 155 When everything falls apart at the same time

    How to Make Adulting Suck Less: https://jessdiamondcoaching.com/suck-less/ This episode is all about what to do when life decides to life… and by that I mean everything falls apart all at once and you can't seem to catch your breath. The truth is, you can't hit pause on life while everything falls apart, but you can learn how to handle it without burning yourself out in the process. I break down how to shift your priorities, focus on what you can actually control, and stop looking at everything as one giant overwhelming mess. If you're in the thick of it right now, this episode is your reminder that your only job is to show up. Key Takeaways: Trying to power through when everything falls apart only makes things worseNot everything needs your attention equallyFocus on what you can control and let go of what you can'tHard seasons build resilience you'll need for the rest of adulthoodThis feeling is temporary, even when it doesn't feel that way Helpful Resources: How to stop spiraling: https://jessdiamondcoaching.com/spiral/ 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

    13 min

  4. May 25

    Ep. 154 You did it! Now What?

    How to Make Adulting Suck Less: https://jessdiamondcoaching.com/suck-less/ In this episode, I'm talking about the low that follows a really big high… that "now what?" feeling that hits after you finally accomplish something you've been working toward. Whether it's landing a job, getting married, finishing a big project, or hitting a major milestone, I share why that post-achievement drop is completely normal and what to do about it. The goal was never just to get the thing – it was to build something meaningful once you did. Key Takeaways: The process of working toward a goal was keeping you occupied and giving you purpose, so its absence is what creates the empty feelingI’ll be happy when syndrome sets you up for disappointmentHow to have something new on the horizon before the big thing happensLearn to live in the mundaneHow this achievement can be the launch pad for what’s next 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

    12 min

  5. May 18

    Ep. 153 The problem with always accomplishing things

    How to Make Adulting Suck Less: https://jessdiamondcoaching.com/suck-less/ This episode breaks down the problem with always needing to accomplish things and why getting everything done doesn’t always mean you did it well. I talk about how constantly saying yes and rushing through your life leads to mistakes, poor communication, and people feeling overlooked.It’s time to start looking at your days differently, not just by what you got done, but by how you showed up while doing it. This episode is a reminder that being busy doesn’t excuse being inconsiderate, and that your self-worth isn’t measured by how much you accomplish. At the end of the day, the goal isn’t to rush through your life… it’s to actually be in it while you’re accomplishing it. Key Takeaways: Your urgency doesn’t stay with you… it spills over onto everyone around you.Success on paper is not the same as success in real life.You don’t need more time, you need better boundaries around your timeWhat can you say ‘no’ or ‘not right now’ to?Stop wearing your busyness as a badge of honor 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

  6. May 11

    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

  7. 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

  8. 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
See All (158)

Trailer

4.9
out of 5
12 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 - 2026
  • Episodes
    158
  • Rating
    Explicit
  • Copyright
    © Copyright 2026 Jess Diamond
  • Show Website
    how to twenty-something