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.
Be sure to visit the podcast's website and support the creator: how-to-twenty-something.captivate.fm
Author
Jess Diamond
Category
Podcast website
Latest episode
Nov 2, 2026
Where to listen?
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Episodes
Ep. 177 Getting Over a Slump 02.11.2026 14:28
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 Summary What do you do when you’re putting in the work, but nothing seems to be happening? In this episode, I’m talking about getting through a slump, that frustrating period where you’re applying for jobs, going on dates, working toward a g...
Ep. 176 Deciding to be child free 26.10.2026 15:24
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 Summary Do you actually want kids, or have you just always assumed that having kids is what you're supposed to do? In this episode, I'm talking about the decision to have children versus remaining child-free, and why this is a decision you a...
Ep. 175 Quality Over Quantity 19.10.2026 13:13
Episode Summary You've probably been told that everything is a numbers game: apply to more jobs, go on more dates, attend more networking events, meet more people. But what if doing more isn't actually getting you anywhere? In this episode, I'm talking about why quality matters more than quantity when it comes to dating, making friends, and building your career. I share how I'm changing my own app...
Ep. 174 Why is it so hard to ask for help 12.10.2026 16:20
Show Notes 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 Summary We are usually more than happy to help someone else when they need us, yet the second we're the ones who need support, we suddenly convince ourselves that we should be able to figure it out on our own. In this episode, I'm...
Ep. 173 Stop waiting for permission in your career with Austin Lutz 05.10.2026 57:35
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 Summary What if you stopped waiting for someone to give you permission to build the career you actually want? In this episode, I’m joined by Austin Lutz, a technology consultant, entrepreneur, product builder, and host of Lut's Talk, to talk...
Ep. 172 Nothing Changes If Nothing Changes 28.09.2026 15:10
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 Summary If you're unhappy with where you are but keep doing the exact same things, I have some tough love for you: nothing changes if nothing changes. In this episode, I'm talking about why we stay stuck even when we're miserable, and why kn...
Ep. 171 Why Relatability Matters More Than Advice in Your Twenties 21.09.2026 17:40
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 Summary You don't always need more advice. Sometimes you need someone who actually gets it. In this episode, I'm talking about why relatability matters more than advice , especially when you're navigating your twenties. Because while the peo...
Ep. 170 What it really means to Own Your Life 14.09.2026 15:31
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 Summary What does it actually mean to own your life ? It's a phrase I talk about constantly, but owning your life doesn't mean having everything figured out or knowing exactly where you'll be five years from now. It means taking responsibili...
Ep. 169 What No One Tells You About Getting Pregnant 07.09.2026 17:13
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 Summary We spend so much of our lives being taught how not to get pregnant that we rarely talk about what happens when you actually want to. In this episode, I’m breaking down the realities of trying to conceive that you might not hear about until y...
Ep. 168 The Truth About Life After Graduation with Christiane Palpant 31.08.2026 57:04
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 Summary What if the biggest thing no one tells you about life after graduation is that it's not supposed to be linear ? In this episode, I sit down with professor, author, and speaker Christiane "Professor CP" Palpant to talk about why your...
Ep. 167 The connections you're missing out on by staying comfortable 24.08.2026 20:13
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 Networking doesn't have to mean awkward conversations, business cards, or pretending to be someone you're not. In this episode, I'm breaking down why staying in your comfort zone is costing you more than you realize, the biggest fears that keep us f...
Ep. 166 Are you the partner you want to date? 17.08.2026 16:27
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 sta...
Ep. 165 Get Unplugged: How to Break Your Phone Addiction 10.08.2026 21:51
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...
Ep. 164 When is it time to work with a coach? 03.08.2026 16:50
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 Summary How 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...
Ep. 163 This is not your forever, but it is your for now 27.07.2026 18:47
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 Summary Have 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 l...
Ep. 162 This is why you operate the way you do with Adrienne Craighead 20.07.2026 1:00:27
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 y...
Ep. 161 How to talk to your parents so they actually hear you 13.07.2026 18:17
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 unknowin...
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...
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