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how to twenty-something

how to twenty-something

Jess Diamond 165 Episodes Oct 12, 2026

How To Twenty Something is a career and life advice podcast for young professionals. It covers topics like career development, relationships, and health and wellness. The show aims to help listeners gain confidence, take risks, and reach their full potential.

Episodes

Ep. 174 Why is it so hard to ask for help
Ep. 174 Why is it so hard to ask for help Oct 12, 2026 16:20 Show NotesNEW 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 SummaryWe 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 br
Ep. 173 Stop waiting for permission in your career with Austin Lutz
Ep. 173 Stop waiting for permission in your career with Austin Lutz Oct 5, 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_7I6vDKrIEpisode SummaryWhat 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 abo
Ep. 172 Nothing Changes If Nothing Changes
Ep. 172 Nothing Changes If Nothing Changes Sep 28, 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_7I6vDKrIEpisode SummaryIf 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 knowin
Ep. 171 Why Relatability Matters More Than Advice in Your Twenties
Ep. 171 Why Relatability Matters More Than Advice in Your Twenties Sep 21, 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 SummaryYou 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 people
Ep. 170 What it really means to Own Your Life
Ep. 170 What it really means to Own Your Life Sep 14, 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 SummaryWhat 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 responsibility
Ep. 169 What No One Tells You About Getting Pregnant
Ep. 169 What No One Tells You About Getting Pregnant Sep 7, 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_7I6vDKrISummaryWe 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 you’r
Ep. 168 The Truth About Life After Graduation with Christiane Palpant
Ep. 168 The Truth About Life After Graduation with Christiane Palpant Aug 31, 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 SummaryWhat 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 twe
Ep. 167 The connections you're missing out on by staying comfortable
Ep. 167 The connections you're missing out on by staying comfortable Aug 24, 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_7I6vDKrINetworking 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 fro
Ep. 166 Are you the partner you want to date?
Ep. 166 Are you the partner you want to date? Aug 17, 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_7I6vDKrIWe 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 stand
Ep. 165 Get Unplugged: How to Break Your Phone Addiction
Ep. 165 Get Unplugged: How to Break Your Phone Addiction Aug 10, 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_7I6vDKrIYour 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 fo
Ep. 164 When is it time to work with a coach?
Ep. 164 When is it time to work with a coach? Aug 3, 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 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 t
Ep. 163 This is not your forever, but it is your for now
Ep. 163 This is not your forever, but it is your for now Jul 27, 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 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 lif

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