
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
Show overview
how to twenty-something has been publishing since 2023, and across the 3 years since has built a catalogue of 159 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 19 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 1 weeks ago, with 25 episodes already out so far this year. Published by Jess Diamond.
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 159 episodesEp. 158 This is your sign to lift weights
Ep. 157 How to Stop Letting Your Mistakes Live Rent Free in Your Head
Ep. 156 Are you quitting or just running away?
Ep. 155 When everything falls apart at the same time
Ep. 154 You did it! Now What?
Ep. 153 The problem with always accomplishing things
Ep. 152 Why skinny doesn't mean healthy
Ep. 151 The biggest conversations you're not having with Brittany Scantland-Lall
Ep. 150 Everything I got wrong in my twenties
Ep. 149 What is your paycheck costing you?
Ep. 148 The reality of being self-employed in your twenties
Ep. 147 Why you feel out of place in your twenties

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

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

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

Ep 143Ep. 143 Life really does get easier
EIn 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

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

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

Ep 140Ep. 140 Building a routine from scratch
EYou 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

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