Jess Diamond
how to twenty-something
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.
Author
Jess Diamond
Category
Podcast website
Latest episode
Jul 6, 2026
Where to listen?
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Episodes
Ep. 160 Is Gen-Z really screwed in the job market? 06.07.2026 16:35
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...
Ep. 159 The Psychology Behind Your Quarter Life Crisis 29.06.2026 15:56
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 suddenl...
Ep. 158 This is your sign to lift weights 22.06.2026 18:53
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....
Ep. 157 How to Stop Letting Your Mistakes Live Rent Free in Your Head 15.06.2026 13:11
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 reacti...
Ep. 156 Are you quitting or just running away? 08.06.2026 16:54
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....
Ep. 155 When everything falls apart at the same time 01.06.2026 13:14
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 h...
Ep. 154 You did it! Now What? 25.05.2026 12:16
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 comple...
Ep. 153 The problem with always accomplishing things 18.05.2026 13:37
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 day...
Ep. 152 Why skinny doesn't mean healthy 11.05.2026 20:57
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 l...
Ep. 151 The biggest conversations you're not having with Brittany Scantland-Lall 04.05.2026 56:04
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...
Ep. 150 Everything I got wrong in my twenties 27.04.2026 20:21
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 kno...
Ep. 149 What is your paycheck costing you? 20.04.2026 16:53
How to Make Adulting Suck Less: https://jessdiamondcoaching.com/suck-less/ This episode is all about your money story : the beliefs you developed about money growing up… and how those beliefs can shape the jobs you take, the lifestyles you build, and the sacrifices you make. I challenge you to look at what your paycheck might actually be costing you from your health, to your relationships, your ti...
Ep. 148 The reality of being self-employed in your twenties 13.04.2026 19:39
Being self-employed isn’t as glamorous as social media makes it out to be. We’re talking numbers, emotions, expectations, timelines, doubts, and the grit that comes with this kind of decision. I walk you through my real income from my first job out of school through my first four years of being self-employed. I talk about the mental and emotional toll of entrepreneurship… the uncertainty, the self...
Ep. 147 Why you feel out of place in your twenties 06.04.2026 13:33
Feeling out of place is a normal part of your twenties. From identity shifts, to unexpected setbacks, to returning home, and the quiet disorientation that comes with becoming a new version of yourself. This episode highlights the gap between expectations and reality, and what happens when your life doesn’t look how you thought it would. If you’ve been feeling unsettled, disconnected, or like you d...
Ep. 146 For if you overthink what you say with Dayna Gowan 30.03.2026 54:57
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...
Ep. 145 Top 10 Red Flags in Your Relationship 23.03.2026 21:17
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...
Ep. 144 How far should you live from work? 16.03.2026 14:56
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...
Ep. 143 Life really does get easier 09.03.2026 12:29
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, friendshi...
Ep. 142 What your coping mechanism says about you 02.03.2026 18:44
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...
Ep. 141 Why quick fixes aren't quick 23.02.2026 14:56
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 epis...
Ep. 140 Building a routine from scratch 16.02.2026 16:26
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 a...
Ep. 139 When You’ve Already Communicated It (and Nothing Changed) 09.02.2026 15:14
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...
Ep. 138 You need to be more picky 02.02.2026 15:10
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.”...
Ep. 137 The fear of wasting your twenties 26.01.2026 16:39
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 behi...
Ep. 136 Why more money isn't the answer 19.01.2026 14:20
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...
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