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. 15h ago

    Ep. 163 This is not your forever, but it is your for now

    NEW COURSE: How to Make Adulting Suck Less: https://jessdiamondcoaching.com/suck-less/ Watch my TEDx Talk: https://www.youtube.com/watch?v=RE_7I6vDKrI Have you ever felt like the options in front of you are a few steps behind where you thought you'd be by now? Maybe it's the job that feels beneath your skill level, living at home longer than planned, or watching everyone else seem to move forward while you're stuck standing still. In this episode, I'm talking about why those "for now" seasons can feel so frustrating and the three things that often make them harder than they need to be. We'll dive into the role ego, expectations, and comparison play in keeping us stuck, and why the stepping stones you're resisting might actually be the things moving you forward. Key Takeaways: Why ego is disappointment in disguiseYour current capabilities and circumstances matter more than what you think you should be able to doThe version of you who created your life plan didn't have all the information you have nowHow to stop measuring your behind the scenes with someone else’s highlight reelThe best tactic to understanding how past stepping stones helped you get to where you re today Helpful Resources: Let’s chat: https://calendly.com/coach_jessdiamond/success How 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 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

  2. Jul 20

    Ep. 162 This is why you operate the way you do with Adrienne Craighead

    Claim your free Human Design Chart before you listen: https://bit.ly/HD101-AC WATCH MY TEDX TALK: https://www.youtube.com/watch?v=RE_7I6vDKrI Human design is the ultimate personality test. In this episode, Adrienne Craighead, not only reads my chart, but breaks down how you can read and interpret your own chart. This is super valuable for helping you make decisions that align with who you are to your core based on your birth place, birth date, and birth time. Key Takeaways: How to use human design as a another tool in your tool boxWhat your chart says about youEverything on your chart could be a blessing or a burden based on how you make it mean 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 Adrienne Craighead: Free Human Design Reading: https://bit.ly/HD101-AC Other links to connect: https://linktr.ee/adriennec2 USE JESS20 AT CHECKOUT 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

  3. Jul 13

    Ep. 161 How to talk to your parents so they actually hear you

    WATCH MY TEDX TALK: https://www.youtube.com/watch?v=RE_7I6vDKrI NEW COURSE: How to Make Adulting Suck Less: https://jessdiamondcoaching.com/suck-less/ If you have ever felt like your parents just do not hear you no matter what you say, this episode is going to help you figure out why and what to do about it. A big part of the problem is not what you are saying but the dynamic you are both unknowingly stuck in, and once you understand it, everything changes. I am walking you through the most common mistakes people make when bringing news or updates to their parents, why having a plan completely changes the outcome of those conversations, and how the relationship you build with your parents day to day matters just as much as how you deliver the news in the moment. I also get into what to do when the conversation starts to go sideways despite your best efforts, because their reaction is one thing you cannot control but how you show up is entirely up to you. If you have been putting off a hard conversation with your parents or keep finding that things go left no matter how hard you try, this one is for you. Key Takeaways: Are you acting immature or are your parents treating you like a child?A plan turns a confession into a conversationDecide before the conversation whether you are asking for help, advice, or just want to be heardAlways lead with context and follow with what you are doing about itThe relationship you build with your parents day to day directly impacts how conversations go when things get hardTreat your parents like people, not an ATM, not a therapist, not a personal assistant 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

  4. Jul 6

    Ep. 160 Is Gen-Z really screwed in the job market?

    NEW COURSE: How to Make Adulting Suck Less: https://jessdiamondcoaching.com/suck-less/ The job market is tough right now and I'm not going to sugarcoat it. In this episode I'm breaking down the real statistics behind what's happening with entry level jobs, why AI is a massive driver behind it, and whether Gen Z is actually screwed or just searching the wrong way. Spoiler: it's a little bit of both. I'm sharing what I'm seeing with my own clients, the mindset shifts that separate the people landing jobs from the ones still waiting for an email back, and why the way your parents found their jobs has absolutely nothing to do with what works today. If you're currently in the thick of a job search that feels like it's going nowhere, this episode will give you some honest perspective and a better direction to move in. Because the people landing jobs right now aren't doing anything magical, they're just doing things differently. Key Takeaways: Why entry level jobs are harder to land than ever beforeHow AI is changing the hiring process and what that means for youWhy mass applying online is not an effective job search strategyHow your mindset directly impacts your ability to land a jobThe truth behind job postingsYour first job out of school is not going to be what you think it is 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

  5. Jun 29

    Ep. 159 The Psychology Behind Your Quarter Life Crisis

    WATCH MY TEDX TALK: https://www.youtube.com/watch?v=RE_7I6vDKrI How to Make Adulting Suck Less: https://jessdiamondcoaching.com/suck-less/ If your twenties have felt confusing, disorienting, or like everyone else somehow got the manual you missed… this episode is for you. In today’s conversation, I break down the psychology behind the “quarter life crisis” and why so many twenty-somethings suddenly feel the urge to blow up their lives, switch careers, move cities, go back to school, or completely start over. From social media comparisons and post-grad uncertainty to identity shifts, major life transitions, and the science behind your still-developing brain, this episode unpacks what’s actually happening beneath the surface of all those “what am I doing with my life?” thoughts. I also share pieces of my own journey leaving corporate life, moving to Charlotte, and learning how to separate impulsive reactions from genuine clarity. Key Takeaways: Why quarter life crises are so common in your twentiesThe psychological and emotional changes happening between 18–30How social media distorts your perception of success and timingThe role your prefrontal cortex plays in decision-makingWhy feeling lost can actually be a sign of growthHow to tell the difference between impulsivity and intuitionWhat to do when you feel the urge to completely change your lifeWhy you don’t need a full life plan — just the next stepHow external processing and support can help you navigate uncertainty 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

  6. Jun 22

    Ep. 158 This is your sign to lift weights

    NEW COURSE: How to Make Adulting Suck Less: https://jessdiamondcoaching.com/suck-less/ Watch my TEDx Talk: https://www.youtube.com/watch?v=RE_7I6vDKrI In this episode I am breaking down why your twenties are genuinely the best time to build muscle and strength, what happens to your body if you wait until your thirties to start, and why this matters just as much for your mind as it does your body. I am also calling out the fears that keep you stuck on the cardio machines, the not knowing what to do, the fear of being judged, because spoiler, no one in that gym is watching you as closely as you think. And once we get your head in the right place, I am handing you the exact plan I use with my own clients so you can walk in with dumbbells and zero confusion about what to do. This is the why, the mindset, and the plan, all in one episode. Now go lift something. Key Takeaways: Why your twenties are the best decade to get started in the gymWaiting to lift weights comes at a costThe most common fears talking you out of going to the gymYou don’t need to spend hours in the gym to see resultsThe simple framework to help you walk in the gym with a planConsistency matters more than intensity 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

  7. Jun 15

    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

  8. 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

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4.9
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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
    164
  • Rating
    Explicit
  • Copyright
    © Copyright 2026 Jess Diamond
  • Show Website
    how to twenty-something