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how to twenty-something

how to twenty-something

A podcast that helps young professionals navigate their twenties, develop new perspectives, process common challenges, and encourages them to get their sh*t together so they can create a life that’s worth living.

Jess Diamond

153 episodesENExplicit

Show overview

how to twenty-something has been publishing since 2023, and across the 3 years since has built a catalogue of 153 episodes, alongside 1 trailer or bonus episode. That works out to roughly 85 hours of audio in total. Releases follow a weekly cadence.

Episodes typically run twenty to thirty-five minutes — most land between 20 min and 53 min — with run-times ranging widely across the catalogue. The publisher flags most episodes as explicit, so expect adult themes or strong language throughout. It is catalogued as a EN-language Education show.

The show is actively publishing — the most recent episode landed 3 days ago, with 19 episodes already out so far this year. Published by Jess Diamond.

Episodes
153
Running
2023–2026 · 3y
Median length
24 min
Cadence
Weekly

From the publisher

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.

Latest Episodes

View all 153 episodes

Ep. 152 Why skinny doesn't mean healthy

May 11, 202620 min

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

May 4, 202656 min

Ep. 150 Everything I got wrong in my twenties

Apr 27, 202620 min

Ep. 149 What is your paycheck costing you?

Apr 20, 202616 min

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

Apr 13, 202619 min

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

Apr 6, 202613 min

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

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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/maximizeEmail Me: [email protected] 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.comCreative Commons/Attribution 3.0 Unported License (CC BY 3.0) https://creativecommons.org/licenses/by/3.0/deed.en_US

Mar 30, 202654 min

Ep 145Ep. 145 Top 10 Red Flags in Your Relationship

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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 leaveHelpful Resources: Let’s chat: https://calendly.com/coach_jessdiamond/success Email me: [email protected] 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.comCreative Commons/Attribution 3.0 Unported License (CC BY 3.0) https://creativecommons.org/licenses/by/3.0/deed.en_US

Mar 23, 202621 min

Ep 144Ep. 144 How far should you live from work?

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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 themHelpful Resources: Let’s chat: https://calendly.com/coach_jessdiamond/success Email me: [email protected] Tickets March 28th: tedxsugarcreekwomen.com Use code: VIP25 at checkout3 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.comCreative Commons/Attribution 3.0 Unported License (CC BY 3.0) https://creativecommons.org/licenses/by/3.0/deed.en_US

Mar 16, 202614 min

Ep 143Ep. 143 Life really does get easier

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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 worthHelpful Resources: Let’s chat: https://calendly.com/coach_jessdiamond/success Email me: [email protected] Tickets March 28th: tedxsugarcreekwomen.com Use code: VIP25 at checkout3 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.comCreative Commons/Attribution 3.0 Unported License (CC BY 3.0) https://creativecommons.org/licenses/by/3.0/deed.en_US

Mar 9, 202612 min

Ep 142Ep. 142 What your coping mechanism says about you

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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 stuckHelpful Resources: Let’s chat: https://calendly.com/coach_jessdiamond/success Email me: [email protected] Tickets March 28th: tedxsugarcreekwomen.com Use code: VIP25 at checkout3 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.comCreative Commons/Attribution 3.0 Unported License (CC BY 3.0) https://creativecommons.org/licenses/by/3.0/deed.en_US

Mar 2, 202618 min

Ep 141Ep. 141 Why quick fixes aren't quick

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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: [email protected] 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.comCreative Commons/Attribution 3.0 Unported License (CC BY 3.0) https://creativecommons.org/licenses/by/3.0/deed.en_US

Feb 23, 202614 min

Ep 140Ep. 140 Building a routine from scratch

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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: [email protected] 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.comCreative Commons/Attribution 3.0 Unported License (CC BY 3.0) https://creativecommons.org/licenses/by/3.0/deed.en_US

Feb 16, 202616 min

Ep 139Ep. 139 When You’ve Already Communicated It (and Nothing Changed)

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If you’ve communicated clearly, calmly, and more than once, and nothing has changed, this episode is for you. It isn’t about learning how to communicate better in the moment; it’s about recognizing when communication stops being the problem and becomes a decision point. We’ll talk about boundaries, changing expectations, and why sometimes leaving is the answer, so you can keep the right people in your inner circle and walk away from the rest. If you’ve ever felt stuck having the same conversation on repeat, this episode is for you, because at some point, it’s time to believe the behavior, not the potential.Key Takeaways:Believe the behavior not the potentialWhat boundaries you can set when you’re constantly repeating yourself and what you needSomeone can hear you, validate you, agree with you, and still choose not to changeApologies over time need actionYou’re not under-communicating, you’re overcommunicatingHelpful Resources: Let’s chat: https://calendly.com/coach_jessdiamond/success Email me: [email protected] 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.comCreative Commons/Attribution 3.0 Unported License (CC BY 3.0) https://creativecommons.org/licenses/by/3.0/deed.en_US

Feb 9, 202615 min

Ep 138Ep. 138 You need to be more picky

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This episode breaks down why being picky is not a bad thing and how this doesn’t only apply to dating. The truth is your friendships, career, and relationship with yourself all deserve the same level of discernment. This episode is about learning to communicate your needs, noticing when something never fully feels right, and giving yourself permission to walk away even when nothing is “that bad.” Because you’re not too picky.. you just have high standards, and honoring them will make your life a whole lot healthier.Key Takeaways:Being “too picky” is usually just another way of saying you finally have standardsIf someone consistently leaves you feeling drained, confused, anxious, or disappointed, it’s time to walk awayHow someone shows up early on is who they areThe wrong someone is not better than no oneHelpful Resources: Let’s chat: https://calendly.com/coach_jessdiamond/success Email me: [email protected] 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.comCreative Commons/Attribution 3.0 Unported License (CC BY 3.0) https://creativecommons.org/licenses/by/3.0/deed.en_US

Feb 2, 202615 min

Ep 137Ep. 137 The fear of wasting your twenties

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This episode breaks down why we all fear wasting our twenties. The pressure to travel, date, go out every weekend, and have life “figured out” can make it feel like one wrong choice will mess everything up. There are two sides I discuss when it comes to this fear: fear of missing the fun parts and fear of falling behind the milestones your peers are hitting. If you’ve ever worried that you’re behind, doing something wrong, or running out of time, this episode is for you. Because changing your mind, starting over, and choosing what feels aligned isn’t wasting your twenties, and this episode breaks down why.Key Takeaways:The fear of wasting your twenties usually shows up in two ways: having fun and hitting milestonesThere is no universal blueprint for how your twenties are supposed to lookComparison will always make it feel like everyone else is aheadThe only real way to waste your twenties is by staying in situations that no longer serve you because you’re afraid to start over.Helpful Resources: Let’s chat: https://calendly.com/coach_jessdiamond/success Email me: [email protected] 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.comCreative Commons/Attribution 3.0 Unported License (CC BY 3.0) https://creativecommons.org/licenses/by/3.0/deed.en_US

Jan 26, 202616 min

Ep 136Ep. 136 Why more money isn't the answer

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In this episode, I’m breaking down one of the biggest money myths twenty-somethings fall for: the idea that more money will magically fix your financial stress. The truth is that most of us go from living within our parents’ means to suddenly trying to replicate that same lifestyle on an entry-level salary. I walk you through why side hustles and second jobs are usually just bandaid solutions, how more income actually magnifies your spending habits, and what it looks like to finally live within your means instead of someone else’s. If you feel like you’re scraping by and don’t want to give up all of your favorite things, then this episode is for you.Key Takeaways:If your spending isn’t intentional now, a bigger paycheck will only magnify what’s already happeningYou need to know your real monthly expenses—rent, utilities, groceries, subscriptions, everythingChoose 3–5 things you’re unwilling to give up, and allocate money toward them intentionally instead of impulsivelyYour early twenties are financially unfair.When you build a realistic foundation that matches your income, that’s when making more money actually starts to help.Helpful Resources: Let’s chat: https://calendly.com/coach_jessdiamond/success Email me: [email protected] 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.comCreative Commons/Attribution 3.0 Unported License (CC BY 3.0) https://creativecommons.org/licenses/by/3.0/deed.en_US

Jan 19, 202614 min

Ep 135Ep. 135 If you're unhappy with where you're at

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This episode is for you if you’re facing a season of discontent. Whether it’s career dissatisfaction, friendship shifts, relationship anxiety, and even how the city you live in can make you feel stuck, it’s important for you to figure out what’s in your control, how to give yourself a deadline, and how to take action without burning your life down. My goal is to help you stop tolerating a life that feels “meh” and start recognizing unhappiness as a sign that it’s time to make changes in your life. Key Takeaways:A deadline can help you stop tolerating situations you’ve been settling forThere are always more options than the extreme ones your brain offersNothing changes until you get honest about what is in your control.The three questions to ask yourself when it comes to becoming happierYou are only in control of yourself: your own actions and reactionsHelpful Resources: Let’s chat: https://calendly.com/coach_jessdiamond/success Email me: [email protected] 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.comCreative Commons/Attribution 3.0 Unported License (CC BY 3.0) https://creativecommons.org/licenses/by/3.0/deed.en_US

Jan 12, 202616 min

Ep 134Ep. 134 Rewind and reflect for what's next!

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This episode guides you through a real rewind and reflection of my 2025 — the wins, the hard stuff, and how I’m using both to set more intentional goals for 2026. I share some of my biggest highlights, most painful losses, and help you pause, reflect on your own, and actually celebrate what you’ve done instead of brushing it off. I also walk you through how I’m setting goals for 2026 and share some pretty exciting announcements about what’s coming next (including my first ever TEDx Talk). My hope is that this episode helps you reflect with honesty, get clear on what you want, and feel excited about the version of you you’re walking into this year.Key Takeaways:Walking away doesn’t mean you failedWhy you need to look back before you can look aheadWhere most people mess up when setting new years resolutionsThe different types of reflectionsHow to set yourself up for the year aheadHelpful Resources: Let’s chat: https://calendly.com/coach_jessdiamond/success Email me: [email protected] 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.comCreative Commons/Attribution 3.0 Unported License (CC BY 3.0) https://creativecommons.org/licenses/by/3.0/deed.en_US

Jan 5, 202617 min

Ep 133Ep. 133 When nothing sounds like a good idea

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What happens when nothing sounds like a good idea and you feel completely stuck in your life? This episode talks about how we usually end up in one of two places: the Land of No or the Land of I Don’t Know, and how both keep us stuck even though they look different. It’s filled with real stories from my life and my clients' lives and how we’ve worked to book our one way ticket out of these lands. If you feel like you’ve been the mayor of either land, this episode will help you start building momentum again and finding your way out.Key Takeaways:The Land of No shows up when you reject every idea immediately because you’re trying to protect yourself from disappointment or failure.The Land of I Don’t Know disguises itself as overthinking, caution, or being “open-minded,” when it’s really fear of choosing wrongHow being in a funk can keep you in your respective landThe tiny actions you can take today to find your way out of your land.Helpful Resources: Let’s chat: https://calendly.com/coach_jessdiamond/success Email me: [email protected] 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.comCreative Commons/Attribution 3.0 Unported License (CC BY 3.0) https://creativecommons.org/licenses/by/3.0/deed.en_US

Dec 29, 202516 min
Copyright 2026 Jess Diamond