how to twenty-something

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

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 this episode, I explain the difference between coaching and therapy, the five biggest signs that coaching could help you move forward, and why having someone in your corner can help you overcome the blind spots, fears, and resistance that keep you from making lasting change.

I also walk you through the different types of coaches that exist—from career and business coaches to relationship, nutrition, and life coaches—so you can better understand what kind of support fits your current season of life. Finally, I take you behind the scenes of my Own Your Life System, the six-pillar coaching framework I've developed to help twenty-somethings build confidence, create meaningful goals, establish healthy routines, improve communication, and take ownership of their lives.

Whether you're considering coaching with me or simply wondering if coaching is the right next step for you, this episode will help you recognize when it's time to stop trying to figure everything out alone.

• The difference between coaching and therapy
• Five signs it's time to work with a coach
• Why knowing what to do isn't the same as doing it
• How fear and resistance keep you stuck
• Why life transitions are easier with support
• The different types of coaches available
• What to look for when choosing a coach
• The six pillars of my Own Your Life System

This episode is for you if...

• You keep setting the same goals but never follow through.
• You know exactly what you should be doing but can't seem to do it.
• You feel stuck and can't explain why.
• You're navigating a major life transition.
• You're wondering if coaching is worth the investment.

• Coaching focuses on helping you move from where you are to where you want to be.
• Repeating the same goals without changing your approach usually points to missing systems, not lack of motivation.
• Fear of the unknown often creates resistance, even when you know the next step.
• Feeling stuck doesn't always mean something is wrong—it may mean you've outgrown your current season.
• Major life transitions are easier to navigate with guidance and accountability.
• Your friends can support you emotionally, but they aren't responsible for helping you create lasting change.
• There is a coach for almost every niche, life stage, and challenge.
• Choosing a coach is about both expertise and finding someone you genuinely connect with.
• Building confidence comes from consistently showing up for yourself.
• You don't have to figure out adulthood on your own.

What's the difference between coaching and therapy?

Therapy focuses on healing and processing your past, while coaching helps you create a plan for the future and take action toward your goals.

How do I know if I need a coach?

If you feel stuck, keep repeating the same patterns, struggle to follow through, or want accountability while working toward a goal, coaching may be a great fit.

Is coaching only for people who are struggling?

Not at all. Coaching is for anyone who wants to grow, create change, or reach goals more effectively.

How do I choose the right coach?

Start by identifying the area of your life you want help with, then find someone whose experience, personality, and coaching style align with what you're looking for.

What is the Own Your Life System?

The Own Your Life System is my six-pillar coaching framework focused on Create, Consistency, Control, Connect, Communicate, and Confidence to help twenty-somethings build a life that's truly their own.

Helpful Resources:

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

How to stop spiraling: https://jessdiamondcoaching.com/spiral/

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

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

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 life isn't moving as quickly as you hoped, it's easy to believe you've somehow fallen behind.

In this episode, I share a coaching conversation with one of my clients that completely changed how she viewed her career—and how it applies to every twenty-something navigating adulthood. We unpack the three biggest reasons we resist taking the stepping stones in front of us: ego, expectations, and comparison. I explain why your ego is often disappointment in disguise, how unrealistic expectations trap you into believing there's only one "right" timeline, and why comparing your behind-the-scenes to someone else's highlight reel will always leave you feeling like you're losing.

Most importantly, I want to remind you that where you are today doesn't have to be where you stay. Your current season isn't your forever—it's simply your for now. Every stepping stone, even the frustrating ones, is preparing you for opportunities you can't yet see.

• Why your current season doesn't define your future
• The hidden cost of letting your ego make career decisions
• How expectations create unnecessary disappointment
• Why comparison keeps you feeling behind
• The importance of taking stepping stones instead of waiting for the "perfect" opportunity
• How to recognize the value in jobs or experiences that don't feel exciting
• Why your twenties are about adapting, not following a perfect plan
• A practical exercise to help you appreciate where you are today

This episode is for you if...

• You feel like you're behind everyone else your age.
• You're frustrated by a job that feels beneath your qualifications.
• You're living with your parents longer than expected.
• You're rebuilding after a setback, injury, or difficult season.
• You're wondering if taking a "small" opportunity means settling.

• Every stepping stone serves a purpose, even if you can't see it yet.
• Ego often disguises itself as disappointment.
• Expectations should evolve as life gives you new information.
• Your first opportunity doesn't have to be your forever career.
• Comparison steals your ability to appreciate your own progress.
• Social media rarely shows the difficult parts of someone's journey.
• Small opportunities often create bigger ones later.
• Looking back at your own story helps you recognize how far you've come.
• Give yourself timelines for temporary seasons so they feel intentional.
• Your "for now" can become the foundation for everything you want next.

Why do I feel behind in my twenties?

Because you're comparing your real life to other people's visible milestones while holding yourself to expectations that may no longer fit your life.

How do I stop comparing myself to everyone else?

Shift comparison from evidence that you're failing to proof that what you want is possible.

Should I take a job I'm overqualified for?

Sometimes the right opportunity isn't your destination—it's the stepping stone that gets you there.

What if my life doesn't look like I expected?

That's normal. The most important skill you can develop is adapting your plan as life unfolds.

How do I stay motivated during a frustrating season?

Remember that your current circumstances are temporary. Give yourself a clear goal and timeline so your "for now" feels purposeful instead of permanent.

• Why You Feel Behind in Your Twenties (This Is Not Your Forever)
• The Psychology Behind Your Quarter-Life Crisis
• This Is NOT Your Life: Stop Living Everyone Else's Plan
• How to Make Your Next Move When You Feel Stuck

Helpful Resources:

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

How to stop spiraling: https://jessdiamondcoaching.com/spiral/

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

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 your core based on your birth place, birth date, and birth time.

Key Takeaways:

1. How to use human design as a another tool in your tool box
2. What your chart says about you
3. Everything on your chart could be a blessing or a burden based on how you make it mean

Helpful Resources:

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

3 ways to stop spiraling: https://jessdiamondcoaching.com/spiral/

Email Me: [email protected]

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

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

Connect with Adrienne Craighead:

Free Human Design Reading: https://bit.ly/HD101-AC

Other links to connect: https://linktr.ee/adriennec2

USE JESS20 AT CHECKOUT

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

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 unknowingly stuck in, and once you understand it, everything changes. I am walking you through the most common mistakes people make when bringing news or updates to their parents, why having a plan completely changes the outcome of those conversations, and how the relationship you build with your parents day to day matters just as much as how you deliver the news in the moment. I also get into what to do when the conversation starts to go sideways despite your best efforts, because their reaction is one thing you cannot control but how you show up is entirely up to you. If you have been putting off a hard conversation with your parents or keep finding that things go left no matter how hard you try, this one is for you.

Key Takeaways:

• Are you acting immature or are your parents treating you like a child?
• A plan turns a confession into a conversation
• Decide before the conversation whether you are asking for help, advice, or just want to be heard
• Always lead with context and follow with what you are doing about it
• The relationship you build with your parents day to day directly impacts how conversations go when things get hard
• Treat your parents like people, not an ATM, not a therapist, not a personal assistant

Helpful Resources:

How to stop spiraling: https://jessdiamondcoaching.com/spiral/

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

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.

I'm sharing what I'm seeing with my own clients, the mindset shifts that separate the people landing jobs from the ones still waiting for an email back, and why the way your parents found their jobs has absolutely nothing to do with what works today. If you're currently in the thick of a job search that feels like it's going nowhere, this episode will give you some honest perspective and a better direction to move in. Because the people landing jobs right now aren't doing anything magical, they're just doing things differently.

Key Takeaways:

• Why entry level jobs are harder to land than ever before
• How AI is changing the hiring process and what that means for you
• Why mass applying online is not an effective job search strategy
• How your mindset directly impacts your ability to land a job
• The truth behind job postings
• Your first job out of school is not going to be what you think it is

Helpful Resources:

How to stop spiraling: https://jessdiamondcoaching.com/spiral/

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

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 suddenly feel the urge to blow up their lives, switch careers, move cities, go back to school, or completely start over.

From social media comparisons and post-grad uncertainty to identity shifts, major life transitions, and the science behind your still-developing brain, this episode unpacks what’s actually happening beneath the surface of all those “what am I doing with my life?” thoughts. I also share pieces of my own journey leaving corporate life, moving to Charlotte, and learning how to separate impulsive reactions from genuine clarity.

Key Takeaways:

1. Why quarter life crises are so common in your twenties
2. The psychological and emotional changes happening between 18–30
3. How social media distorts your perception of success and timing
4. The role your prefrontal cortex plays in decision-making
5. Why feeling lost can actually be a sign of growth
6. How to tell the difference between impulsivity and intuition
7. What to do when you feel the urge to completely change your life
8. Why you don’t need a full life plan — just the next step
9. How external processing and support can help you navigate uncertainty

Helpful Resources:

How to stop spiraling: https://jessdiamondcoaching.com/spiral/

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

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. I am also calling out the fears that keep you stuck on the cardio machines, the not knowing what to do, the fear of being judged, because spoiler, no one in that gym is watching you as closely as you think. And once we get your head in the right place, I am handing you the exact plan I use with my own clients so you can walk in with dumbbells and zero confusion about what to do. This is the why, the mindset, and the plan, all in one episode. Now go lift something.

Key Takeaways:

1. Why your twenties are the best decade to get started in the gym
2. Waiting to lift weights comes at a cost
3. The most common fears talking you out of going to the gym
4. You don’t need to spend hours in the gym to see results
5. The simple framework to help you walk in the gym with a plan
6. Consistency matters more than intensity

Helpful Resources:

How to stop spiraling: https://jessdiamondcoaching.com/spiral/

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

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 reaction is so much more common than you think. The problem isn't the mistake itself, it's that you start tying it to your worth as a person and suddenly you're not someone who made a mistake, you're convinced you are the mistake. It’s time to learn how to not dwell on this mistake for longer than you need to.

Key Takeaways:

1. Making mistakes is the most human thing you could do
2. What are you making this mistake mean about you or your capabilities?
3. How to not let imposter syndrome convince you you’re not good enough
4. Stop over apologizing
5. Fix what you can fix, learn what you can learn, and then let it go
6. The goal is never to never make a mistake again, it’s to react better

Helpful Resources:

How to stop spiraling: https://jessdiamondcoaching.com/spiral/

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

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. If you've ever had the itch to leave a job, a relationship, school, or any kind of commitment the second it gets hard, this one is for you.

Key Takeaways:

1. Quitting and running away look identical on the outside but the difference lies in the why behind the decision
2. Running away doesn't make the problem disappear, it just delays it and guarantees it shows up again
3. There's a big difference between making a decision and having a reaction
4. Staying somewhere longer than you want to can actually set you up for a much smoother transition into what's next

Helpful Resources:

How to stop spiraling: https://jessdiamondcoaching.com/spiral/

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

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 how to shift your priorities, focus on what you can actually control, and stop looking at everything as one giant overwhelming mess. If you're in the thick of it right now, this episode is your reminder that your only job is to show up.

Key Takeaways:

1. Trying to power through when everything falls apart only makes things worse
2. Not everything needs your attention equally
3. Focus on what you can control and let go of what you can't
4. Hard seasons build resilience you'll need for the rest of adulthood
5. This feeling is temporary, even when it doesn't feel that way

Helpful Resources:

How to stop spiraling: https://jessdiamondcoaching.com/spiral/

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