how to twenty-something

No one warns you about the different types of loss that comes with growing up. It’s not all bad, but it is bittersweet. You lose old versions of yourself, friendships that don’t fit anymore, jobs that once felt stable, and even the direction you thought your life was headed in. This episode is to help you identify where you’re experiencing loss in your life and why you’re going to be confused around your feelings. Your grief also represents your growth and both can be true at the same time!

Key Takeaways:

• You grieve two things at once: who you used to be and the people who were beside you during that version of your life
• Losing your job, your sense of direction, or friendships doesn’t mean you’re doing something wrong
• It’s okay to miss what’s gone and still be proud of where you’re headed
• You can outgrow timelines, expectations, and versions of yourself you once thought were permanent

Helpful Resources: 

Let’s chat: https://calendly.com/coach_jessdiamond/success 

Email me: [email protected]

3 Ways to walk in a room with confidence: jessdiamondcoaching.com/confidence

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.com

Creative Commons/Attribution 3.0 Unported License (CC BY 3.0) https://creativecommons.org/licenses/by/3.0/deed.en_US 

Your twenties are basically one big pivot, so let’s talk about how to handle them without losing your mind.

From careers to relationships to moving cities to changing habits, pivots never feel easy in the moment. In this episode I share some of my own pivots, stories from my clients, and why your brain freaks out every time you’re about to make a change. Most importantly, I’ll walk you through how to take small steps forward so the unknown doesn’t feel so overwhelming and you can start building a life that actually fits you.

Key Takeaways:

• Why pivots feel so uncomfortable and why your brain resists them
• Examples of common pivots in your twenties (career, relationships, moving, habits)
• How avoiding a pivot keeps you stuck in a life that doesn’t fit you
• Small steps you can take to make a pivot feel less overwhelming
• The importance of letting go of the “perfect plan” and embracing the unknown

Helpful Resources: 

Let’s chat: https://calendly.com/coach_jessdiamond/success 

Email me: [email protected]

3 Ways to walk in a room with confidence: jessdiamondcoaching.com/confidence

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.com

Creative Commons/Attribution 3.0 Unported License (CC BY 3.0) https://creativecommons.org/licenses/by/3.0/deed.en_US 

In this episode, I’m breaking down one of the biggest living decisions you face in your twenties: should you live with roommates or live alone? I share stories from my own experience,  the real pros and cons of both options, and what it takes to be a good roommate versus a bad one. Whether you’re craving independence, trying to stretch your budget, or figuring out how to not lose a friendship over dirty dishes, this episode will help you think about what living situation makes sense for you in this season of life.

Key Takeaways:

• Living with roommates can save money and provide built-in companionship
• Living alone gives you total freedom, peace, and control over your environment, but comes at a price
• A good roommate communicates, respects boundaries, and follows through on shared responsibilities; a bad roommate does the opposite.
• Safety and lifestyle matter as much as finances – know whether you thrive in companionship or solitude
• You can change your mind multiple times over between living alone or with other people

Helpful Resources: 

Let’s chat: https://calendly.com/coach_jessdiamond/success 

Email me: [email protected]

3 Ways to walk in a room with confidence: jessdiamondcoaching.com/confidence

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.com

Creative Commons/Attribution 3.0 Unported License (CC BY 3.0) https://creativecommons.org/licenses/by/3.0/deed.en_US 

In this episode, I’m diving into the big question we all ask at some point: what’s the point? Whether it’s about college, your 9–5 job, dating, or just life in general, it’s normal to hit those crossroads where you wonder why you’re even doing what you’re doing. I talk about why this question shows up most when we’re burnt out, bored, or in a season of transition, and how you can start to uncover your own reasons for showing up. By the end of this episode, you’ll have tools to figure out your “why,” decide who you’re really showing up for, and remember that your point is going to continue to change.

Key Takeaways:

• Understanding why the question ‘what’s the point?’ comes up so often in your twenties
• “Finding your point” doesn’t have to mean discovering your life’s purpose
• You have control over your point and uncovering what that means to you

Helpful Resources: 

Let’s chat: https://calendly.com/coach_jessdiamond/success 

Email me: [email protected]

3 Ways to walk in a room with confidence: jessdiamondcoaching.com/confidence

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.com

Creative Commons/Attribution 3.0 Unported License (CC BY 3.0) https://creativecommons.org/licenses/by/3.0/deed.en_US 

In this episode, I’m diving into all the things no one really tells you about being an adult. I share the story of my very first “oh crap, I’m an adult” moment and how that experience set the tone for learning that adulthood is full of unexpected challenges. From jobs that don’t feel like your calling, to the struggle of making and keeping friends, to the identity shifts that make you feel out of place, I cover the hidden parts of your twenties that no one prepares you for. Adulthood comes with a lot of responsibility, but also the power to create the life you want for yourself, and this episode breaks down all the secrets and steps that no one tells you about. 

Key Takeaways:

• Your first full-time job is more about learning how to work than finding your life’s calling
• Adulthood is full of unexpected crises, and part of the job is learning what you can and can’t control
• Job loss, quitting, or career pivots are common in your twenties
• Making and keeping friends as an adult takes far more effort than it did in school or college
• Feeling out of place and questioning your path is normal
• You’re responsible for your life and future

Helpful Resources: 

Let’s chat: https://calendly.com/coach_jessdiamond/success 

Email me: [email protected]

3 Ways to walk in a room with confidence: jessdiamondcoaching.com/confidence

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.com

Creative Commons/Attribution 3.0 Unported License (CC BY 3.0) https://creativecommons.org/licenses/by/3.0/deed.en_US 

This episode talks about the gut-punch feeling of “everyone is hanging out without me,” why it hits so hard in your twenties, and how to tell the difference between being excluded and just not being included. I share my own stories (past and very present) of feeling left out, the way our brains love to spiral into the worst-case scenario, and why social media is the absolute worst for feeding that narrative. We’ll dig into how to stick to the facts, communicate what you need without playing the blame game, and create connections for yourself instead of waiting for someone to hand you an invite. So if you’re tired of feeling left out and letting your spiraling thoughts take over, this episode is for you.

Key Takeaways:

• The difference between being excluded and not being included
• Understanding friendship cycles as you move through your twenties
• Why social media isn’t the mind-numbing resource you think it is
• Ways to communicate your feelings without sounding accusatory
• Why it’s usually not about you
• Stop waiting for the invite, create the event

Helpful Resources: 

It's Me, I'm the Problem 9/22: https://jessdiamondcoaching.com/problem/

Let’s chat: https://calendly.com/coach_jessdiamond/success 

Email me: [email protected]

3 Ways to walk in a room with confidence: jessdiamondcoaching.com/confidence

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.com

Creative Commons/Attribution 3.0 Unported License (CC BY 3.0) https://creativecommons.org/licenses/by/3.0/deed.en_US 

In this episode, I’m breaking down what it feels like to be in the in between—that frustrating, uncomfortable space where you're actively working toward your next thing but not there yet. Whether it’s a new job, a relationship, a body goal, or a big life shift, this episode is for anyone stuck in that “not quite yet” phase. I’m sharing five powerful reminders to help you stay grounded, patient, and hopeful as you bridge the gap between where you’ve been and where you’re going. I talk about why it’s so tempting to put your happiness on hold, how to actually measure your progress in the meantime, and what it means to reshape your identity before you arrive at your next milestone.

Key Takeaways:

• You’re going to encounter multiple different in between moments as you grow through your twenties
• Why “it’s not forever, it’s for now” is the most powerful motto to adopt
• Use this time to prepare, plan, and gather the tools you’ll need for your next move
• Have an end date to getting out of the in between
• Claim who you’re becoming, not where you’re currently at

Helpful Resources: 

It's Me, I'm the Problem 9/22: https://jessdiamondcoaching.com/problem/

Let’s chat: https://calendly.com/coach_jessdiamond/success 

Email me: [email protected]

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.com

Creative Commons/Attribution 3.0 Unported License (CC BY 3.0) https://creativecommons.org/licenses/by/3.0/deed.en_US 

No, this is not your typical ‘love yourself’ kind of episode, but rather getting into the real thoughts and real emotions behind being single – the good and the bad. Danielle Facchine, founder of the Single Life Revolution, sheds light on how to keep living your life when you’re single (and why it’s the absolute best time to do so). If you’re deep in the pits of the single life and trying to claw your way out, it’s time for you to learn how to be okay with being single in this current era of your life, why rushing to get into a relationship will not solve all your problems, and how your happiness doesn’t go on pause just because you don’t have that special someone to make memories with. 

Key Takeaways:

• Why it’s so important to spend time being single in your twenties
• How to get over the feeling of being behind
• Wanting a relationship vs no longer wanting to be single
• Being in a relationship will not magically solve all your problems
• Go to things by yourself, even if it’s uncomfortable 
• Your happiness is your responsibility 
• Find reasons to celebrate yourself 
• The level of abundance that comes with singleness

Helpful Resources: 

It's Me, I'm the Problem 9/22: https://jessdiamondcoaching.com/problem/

Let’s chat: https://calendly.com/coach_jessdiamond/success 

Email Me: [email protected]

Contribute to an episode: https://forms.gle/QwvBrZFbZXRdCjQv9 

Be a Guest: https://forms.gle/oiLVCbrydjzaK5pq5 

Connect with Danielle Facchine:

Website: www.daniellefacchine.com 

Instagram: https://www.instagram.com/danielle_facchine/ 

Email: [email protected] 

Music: Hide and Seek by Free Music https://soundcloud.com/fm_freemusic 

Music Promoted by https://www.free-stock-music.com

Creative Commons/Attribution 3.0 Unported License (CC BY 3.0) https://creativecommons.org/licenses/by/3.0/deed.en_US 

If I had to land a full-time job in today’s market, here are the exact five steps I’d take. In this episode, I’m sharing the strategies I wish I knew back when I was mass applying on job boards and wondering why nothing was working. I walk you through how to narrow in on the right industry for you, how to update your resume strategically, and how to actually use LinkedIn the right way. I also talk about building real relationships, both online and in person, and why following up might be the one thing you’re not doing that’s holding you back. Whether you're a fresh grad, switching industries, or just feeling stuck, I break it all down in a way that’s actionable, honest, and rooted in what’s actually working right now. 

Key Takeaways:

• Submitting mass applications online is often a waste of time
• Identify your strengths and interests, not just your degree
• Building connections and relationships everywhere will serve you in the long run
• Networking doesn’t only happen at “networking events”
• Follow up, Follow up, Follow up

Helpful Resources: 

Let’s chat: https://calendly.com/coach_jessdiamond/success 

Email me: [email protected]

3 Ways to walk in a room with confidence: jessdiamondcoaching.com/confidence

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.com

Creative Commons/Attribution 3.0 Unported License (CC BY 3.0) https://creativecommons.org/licenses/by/3.0/deed.en_US 

Moving in together is a big next step for a relationship and there are so many conversations that need to be shared prior to making this decision and progressing your relationship. Which is why I brought on Mylira Green, Relationship Coach and Therapist, to highlight common pitfalls, perspectives, and insight into being confident about deciding to move in together. From finances, to chores, to expectations, and keeping the spark alive in your relationship, there are so many important conversations you need to have, and factors to consider, that will keep peace in the household and your relationship healthy - whether this is the person you end up marrying or not.

Key Takeaways:

• Are you moving in together out of convenience or because it’s the next right step?
• The difference between a roommate and a romantic partner
• How and why to have the money talk… repeatedly 
• Common conversations that MUST be had when you move in together
• It’s healthy and highly recommended to have regular check ins
• Setting shared expectations across an array of subjects
• How to use your love language to pour into one another
• What being intentional looks like now that you’ve moved in together
• Signs you have a strong foundation in your relationship

Helpful Resources: 

Let’s chat: https://calendly.com/coach_jessdiamond/success 

Walk into any room with confidence: https://jessdiamondcoaching.com/confidence/ 

Email Me: [email protected]

Contribute to an episode: https://forms.gle/QwvBrZFbZXRdCjQv9 

Be a Guest: https://forms.gle/oiLVCbrydjzaK5pq5 

Connect with Mylira Green:

Website: www.myliratransforms.com 

Music: Hide and Seek by Free Music https://soundcloud.com/fm_freemusic 

Music Promoted by https://www.free-stock-music.com

Creative Commons/Attribution 3.0 Unported License (CC BY 3.0) https://creativecommons.org/licenses/by/3.0/deed.en_US