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. 5d ago

    Ep. 166 Are you the partner you want to date?

    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 We spend so much time talking about what we want in a partner that we rarely stop to ask ourselves if we're showing up the same way. In this episode, I'm challenging you to hold up the mirror and take an honest look at the qualities, habits, and standards you're bringing into your relationships. We'll talk about the difference between having high standards and having double standards, uncover some common relationship blind spots, and explore what it really means to show up for someone you love. This isn't about settling or lowering your expectations—it's about pairing those expectations with self-accountability. Key Takeaways: Identify what qualities you want in your relationshipWhy high standards should always be paired with high self-accountabilityHow presence is one of the most underrated ways to strengthen a relationshipHow to see your blindspots, when they are blind to youHow to become accountable to the things you say you want in someone else 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. Aug 10

    Ep. 165 Get Unplugged: How to Break Your Phone Addiction

    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 Your relationship to your phone is destroying your relationship to your life. From the moment you wake up to the second you fall asleep, your device has a choke hold on you and I'm getting into exactly what that is doing to your mental health, your focus, your productivity, and your relationships. This episode talks about the hidden damage your phone is creating in your life, tactics to separate yourself from your handheld device, and reminders that the virtual world is not nearly as important as the real world. Because yes, they are different. Key Takeaways: Different ways your phone is messing with your focus, thought patterns, and productivityWhy physical connections is more valuable than digital onesWhat boredom does for you that your phone cannotHow to separate yourself from your phone in little waysWhy your phone is your coping mechanism and is destroying your mental health 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

  3. Aug 3

    Ep. 164 When is it time to work with a coach?

    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 Episode SummaryHow do you know if it's actually time to work with a coach? The truth is, coaching isn't just for people whose lives are falling apart. It's for people who know they're capable of more but feel stuck figuring out how to get there. In this episode, I explain the difference between coaching and therapy, the five biggest signs that coaching could help you move forward, and why having someone in your corner can help you overcome the blind spots, fears, and resistance that keep you from making lasting change. I also walk you through the different types of coaches that exist—from career and business coaches to relationship, nutrition, and life coaches—so you can better understand what kind of support fits your current season of life. Finally, I take you behind the scenes of my Own Your Life System, the six-pillar coaching framework I've developed to help twenty-somethings build confidence, create meaningful goals, establish healthy routines, improve communication, and take ownership of their lives. Whether you're considering coaching with me or simply wondering if coaching is the right next step for you, this episode will help you recognize when it's time to stop trying to figure everything out alone. In This Episode We DiscussThe difference between coaching and therapyFive signs it's time to work with a coachWhy knowing what to do isn't the same as doing itHow fear and resistance keep you stuckWhy life transitions are easier with supportThe different types of coaches availableWhat to look for when choosing a coachThe six pillars of my Own Your Life System Who This Episode Is ForThis episode is for you if... You keep setting the same goals but never follow through.You know exactly what you should be doing but can't seem to do it.You feel stuck and can't explain why.You're navigating a major life transition.You're wondering if coaching is worth the investment. Key TakeawaysCoaching focuses on helping you move from where you are to where you want to be.Repeating the same goals without changing your approach usually points to missing systems, not lack of motivation.Fear of the unknown often creates resistance, even when you know the next step.Feeling stuck doesn't always mean something is wrong—it may mean you've outgrown your current season.Major life transitions are easier to navigate with guidance and accountability.Your friends can support you emotionally, but they aren't responsible for helping you create lasting change.There is a coach for almost every niche, life stage, and challenge.Choosing a coach is about both expertise and finding someone you genuinely connect with.Building confidence comes from consistently showing up for yourself.You don't have to figure out adulthood on your own. Frequently Asked QuestionsWhat's the difference between coaching and therapy? Therapy focuses on healing and processing your past, while coaching helps you create a plan for the future and take action toward your goals. How do I know if I need a coach? If you feel stuck, keep repeating the same patterns, struggle to follow through, or want accountability while working toward a goal, coaching may be a great fit. Is coaching only for people who are struggling? Not at all. Coaching is for anyone who wants to grow, create change, or reach goals more effectively. How do I choose the right coach? Start by identifying the area of your life you want help with, then find someone whose experience, personality, and coaching style align with what you're looking for. What is the Own Your Life System? The Own Your Life System is my six-pillar coaching framework focused on Create, Consistency, Control, Connect, Communicate, and Confidence to help twenty-somethings build a life that's truly their own. 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

  4. Jul 27

    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 Episode SummaryHave you ever looked at your life and thought, "I know I'm capable of more than this." Whether you're living with your parents, working a job that feels beneath your qualifications, recovering from an injury, or simply feeling like life isn't moving as quickly as you hoped, it's easy to believe you've somehow fallen behind. In this episode, I share a coaching conversation with one of my clients that completely changed how she viewed her career—and how it applies to every twenty-something navigating adulthood. We unpack the three biggest reasons we resist taking the stepping stones in front of us: ego, expectations, and comparison. I explain why your ego is often disappointment in disguise, how unrealistic expectations trap you into believing there's only one "right" timeline, and why comparing your behind-the-scenes to someone else's highlight reel will always leave you feeling like you're losing. Most importantly, I want to remind you that where you are today doesn't have to be where you stay. Your current season isn't your forever—it's simply your for now. Every stepping stone, even the frustrating ones, is preparing you for opportunities you can't yet see. In This Episode We DiscussWhy your current season doesn't define your futureThe hidden cost of letting your ego make career decisionsHow expectations create unnecessary disappointmentWhy comparison keeps you feeling behindThe importance of taking stepping stones instead of waiting for the "perfect" opportunityHow to recognize the value in jobs or experiences that don't feel excitingWhy your twenties are about adapting, not following a perfect planA practical exercise to help you appreciate where you are today Who This Episode Is ForThis episode is for you if... You feel like you're behind everyone else your age.You're frustrated by a job that feels beneath your qualifications.You're living with your parents longer than expected.You're rebuilding after a setback, injury, or difficult season.You're wondering if taking a "small" opportunity means settling. Key TakeawaysEvery stepping stone serves a purpose, even if you can't see it yet.Ego often disguises itself as disappointment.Expectations should evolve as life gives you new information.Your first opportunity doesn't have to be your forever career.Comparison steals your ability to appreciate your own progress.Social media rarely shows the difficult parts of someone's journey.Small opportunities often create bigger ones later.Looking back at your own story helps you recognize how far you've come.Give yourself timelines for temporary seasons so they feel intentional.Your "for now" can become the foundation for everything you want next. Frequently Asked QuestionsWhy do I feel behind in my twenties? Because you're comparing your real life to other people's visible milestones while holding yourself to expectations that may no longer fit your life. How do I stop comparing myself to everyone else? Shift comparison from evidence that you're failing to proof that what you want is possible. Should I take a job I'm overqualified for? Sometimes the right opportunity isn't your destination—it's the stepping stone that gets you there. What if my life doesn't look like I expected? That's normal. The most important skill you can develop is adapting your plan as life unfolds. How do I stay motivated during a frustrating season? Remember that your current circumstances are temporary. Give yourself a clear goal and timeline so your "for now" feels purposeful instead of permanent. Related EpisodesWhy You Feel Behind in Your Twenties (This Is Not Your Forever)The Psychology Behind Your Quarter-Life CrisisThis Is NOT Your Life: Stop Living Everyone Else's PlanHow to Make Your Next Move When You Feel Stuck 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

  5. 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

  6. 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

  7. 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

  8. 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

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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
    167
  • Rating
    Explicit
  • Copyright
    © Copyright 2026 Jess Diamond
  • Show Website
    how to twenty-something