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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 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 breaking down why asking for help can feel so uncomfortable, especially in your twenties. We talk about the pressure to appear competent, self-sufficient, and like you have your shit together, even when you're navigating something you've never experienced before. I also talk about vulnerability, the fear of being a burden, pride, and why asking for help doesn't mean you're weak or incapable.
And because knowing you should ask for help and actually doing it are two very different things, I walk you through how to ask for help without immediately talking yourself out of it. From figuring out what kind of help you actually need, identifying the right person to ask, starting with smaller asks, getting specific about what you're struggling with, and learning how to handle a "no," there are practical ways to make asking for help a little less uncomfortable.
Because you can white-knuckle your way through everything yourself, or you can find the people who are a few steps ahead of you and let them help you get there faster.
Who This Episode Is ForWhy is it so hard to ask for help?
Asking for help can feel uncomfortable because we've been taught to associate self-sufficiency with competence. You may worry that needing help means you're weak, incapable, annoying, or a burden, even though you wouldn't think those things about someone else who came to you for support.
How do I ask for help without feeling like a burden?
Start by remembering that the other person gets to decide whether they have the capacity to help you. Instead of deciding for them that you're asking too much, simply ask if they have the capacity to help and give them the opportunity to say yes or no.
What if someone says no when I ask for help?
A no doesn't mean you're unworthy of help or that you shouldn't have asked. People have their own lives, responsibilities, and limitations. If someone can't help you right now, reset and find someone else who can.
How can I get better at asking for help?
Start small. Ask a friend for a recommendation, ask a coworker to review something, or ask someone in your network for a small favor. Vulnerability is a muscle, so the more you practice asking for help, the easier bigger asks can become.
How do I know who to ask for help?
Think about what you're actually struggling with and find someone who has experience in that area. Your boss may be the right person for a work question, while a friend might be better suited for emotional support. The more specific you are, the easier it becomes to find the right person.
What if I don't know what kind of help I need?
That's often part of why asking feels so difficult. Before reaching out, get as specific as you can about whether you're looking for advice, emotional support, a favor, accountability, or simply someone to listen.
Can a coach help me if I don't know how to ask for help?
Absolutely. Coaching can provide a space where you don't have to pretend you have everything figured out. A coach can help you identify what you're struggling with, determine what kind of support you need, and create a plan to move forward.
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
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
Episode 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 about what it actually looks like to take career risks before you feel completely ready. We talk about Austin leaving a stable job for a startup just months before getting married and buying a house, why your twenties can be the best time to take calculated risks, and how to know the difference between a bad idea and an idea that just needs to be reframed.
We also get into the reality of being a multi-passionate person, balancing a full-time job with side projects and family, and why you probably have more time than you think you do. Austin shares how building businesses outside of his full-time career has actually made him better at his day job, while I break down the skills your full-time job can help you develop for the career or business you want to build later.
And perhaps most importantly, we talk about why you shouldn't wait for a promotion, title, degree, or someone else's approval to start doing the work you want to be known for. Your career doesn't have to follow one perfectly planned path—and you don't have to have everything figured out before you start creating opportunities for yourself.
Key TakeawaysHow do I know if I'm ready to take a career risk?
You probably won't ever feel completely ready. The goal isn't to eliminate the risk or fear, but to understand the potential outcomes, think through your options, and decide whether the risk is worth taking.
Should I quit my job to start a business?
Not necessarily. The episode emphasizes that there are multiple ways to build toward something new. You can keep your full-time job while developing skills, networking, testing an idea, and building something on the side before making a bigger transition.
What if my idea isn't working?
Don't immediately assume the entire idea is bad. Look at what isn't working, talk to people outside your immediate circle, gather feedback, and consider whether you need to change the audience, messaging, product, or approach. But also be willing to admit when something genuinely isn't working and move on.
How can I make time for a side project?
You can't manufacture more hours in the day. Instead, you have to decide which projects deserve your limited time and temporarily table things that aren't a priority. Being intentional about your calendar can create more space than you realize.
Why is networking so important in your twenties?
The people you meet can expose you to opportunities, perspectives, and knowledge you wouldn't have access to otherwise. Finding mentors and intentionally building relationships can help you grow faster and connect you to opportunities later in your career.
Do I need to be qualified before I start doing the job I want?
Not always. The episode explores the idea of starting to do the work you want before someone officially gives you permission. You can build skills, take on responsibilities, create projects, and demonstrate your ability before you have the title that says you can.
What if I don't have the right degree or credentials?
Credentials can be valuable, but they aren't the only indicators of whether you're capable of doing something. Skills, curiosity, willingness to learn, follow-through, and the ability to solve problems can matter just as much in many careers.
How do I deal with imposter syndrome?
Recognize that feeling unqualified doesn't necessarily mean you are unqualified. Sometimes you're simply doing something you've never done before. Taking action, building experience, and allowing yourself to learn along the way can help you develop confidence.
Is it okay if my career doesn't follow one path?
Absolutely. Your career can change throughout your twenties, thirties, and beyond. You don't have to choose one permanent identity or have your entire career figured out right now.
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 Austin Lutz
Website: lutztalk.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
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 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 knowing you need to make a change doesn't always mean you're willing to make it. I break down the comfort of the familiar, the fear of the unknown, the complaint loop, and the sunk cost trap that convinces you to stay somewhere simply because you've already invested so much. I also walk you through how to figure out what's actually making you unhappy, whether you're the common denominator in your own patterns, and how to focus on what you actually have control over.
Who This Episode Is ForThis episode is for you if...
Why do I stay in situations that make me unhappy?
Your brain tends to prefer what is familiar and predictable, even when that familiar situation is making you miserable. The unknown can feel more threatening than something you already know how to navigate.
What if I know I need to change but I'm scared?
You probably won't ever feel completely ready. The goal isn't to eliminate fear before you act; it's to learn how to distinguish a real risk from fear that is simply trying to keep you comfortable.
How do I know what I actually need to change?
Get specific about what is making you unhappy. Instead of deciding that your entire job or relationship is the problem, identify the specific action, person, circumstance, or pattern that's creating the issue. Once you identify the actual problem, the solution often becomes more manageable.
What is the sunk cost trap?
The sunk cost trap is staying in something because you've already invested significant time, money, energy, or effort into it. But what you've already invested doesn't mean you have to keep investing if the cost of staying is now greater than the cost of leaving.
What if the same problems keep happening everywhere I go?
It may be time to look at your own patterns. If you're unhappy at every job, in every relationship, or in every city, your circumstances may not be the only problem. You may need to examine your mindset, behaviors, or expectations.
What do I actually have control over?
You can control how you respond, what you ask for, the boundaries you set, and what you decide to do next. You don't have to solve everything—you just need to focus on the parts of the situation where you have agency.
How do I start making a change when everything feels overwhelming?
Don't try to figure out your entire future. Focus on one thing that could move you forward by 1%. Your next step doesn't have to solve the entire problem; it just needs to move you out of where you are.
Do I need to feel ready before I make a big change?
No. Readiness is not a feeling that magically appears one day. Sometimes you have to say yes before you know exactly how, or take the next step while you're still scared.
Can a coach help me get unstuck?
A coach can provide accountability, perspective, and support as you identify what needs to change and follow through on the actions you've decided to take. The key is that you still have to be willing to make the changes.
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
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
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 who love you may have the best intentions, they aren't always living the same version of adulthood that you are.
I break down the difference between someone who can sympathize with what you're going through and someone who truly "gets it," and why having people around you who understand your specific context can make you feel less alone. We talk about friendships, relationships, career advice, finding a coach or therapist, and why different people in your life can serve completely different purposes.
In This Episode We DiscussThis episode is for you if...
What does it mean for someone to "get it"?
Someone who "gets it" doesn't just sympathize with what you're experiencing. They have enough shared context or experience to understand what it actually feels like and can often offer guidance based on something they've personally navigated.
Why does relatability matter so much in your twenties?
Your twenties are filled with experiences that can be very different from person to person. Having people around you who understand your specific stage of life can help you feel less alone and make the advice you receive more relevant.
Does this mean I shouldn't listen to older generations?
No. The episode isn't about ignoring older generations. There is plenty to learn from people who have lived longer than you. The point is to recognize when you're looking for advice about navigating the world as it exists today, and seek out people who understand that current context.
How do I find my "Get It" people?
Start by looking for people who are navigating something similar to you or have recently navigated the road you're currently on. This could be a friend, mentor, coach, therapist, colleague, or community.
What if the people I love don't understand what I'm going through?
That doesn't necessarily mean they don't care about you. Someone can love you deeply and still not understand your current experience. Instead of expecting them to fill every role, look for additional people who can relate to the specific part of your life you're navigating.
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 Christiane Palpant:
Website: https://www.cuethelifeboat.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
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 for the direction you're going, making decisions based on what you want, and being willing to take action even when you don't have the entire plan figured out.
In this episode, I share the story behind my Own Your Life System and how leaving the corporate world forced me to stop doing what I thought I was "supposed" to do and start making decisions for myself. I break down what owning your life looks like in your career, relationships, routines, decisions, and the way you respond when things don't go according to plan.
Because your twenties aren't about figuring out your entire life. They're about figuring out what you want your life to look like right now—and then doing something about it.
In This Episode We DiscussThis episode is for you if...
What does it mean to own your life?
Owning your life means taking responsibility for the direction you're going, making decisions based on your own values and desires, and taking action instead of waiting for life to happen to you.
Do I need to know exactly what I want before I can own my twenties?
No. You don't need your entire life figured out. You need enough clarity to identify what you want to work toward right now and be willing to take the next step.
How do I know if I'm living someone else's life?
Ask yourself whether your current choices are based on what you genuinely want or what your parents, friends, society, or your younger self told you success was supposed to look like.
Is owning your life something you eventually achieve?
No. It's an ongoing process. There isn't a single milestone that means you've officially "made it." It's choosing to show up for the life you want again and again.
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 Christiane Palpant:
Website: https://www.cuethelifeboat.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
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
SummaryWe 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’re already in the middle of it. I talk about why pregnancy can’t be planned as perfectly as the rest of your life, how long it can actually take to conceive, what happens when you come off birth control, and why a negative pregnancy test doesn't automatically mean something is wrong.
I also dive into pregnancy loss and why miscarriage is far more common than many people realize, the impact of age on fertility, why male fertility needs to be part of the conversation, and the many factors that can affect someone’s ability to conceive. And because we live in a world where pregnancy announcements, bumpdates, and newborn photos are constantly appearing on our feeds, I talk about how social media can make an already emotional experience feel even more isolating.
Whether you're nowhere near ready to have kids, starting to think about family planning, or already trying to conceive, this episode is a reminder that there is no universal timeline for pregnancy—and your journey doesn't have to look like anyone else's.
In This Episode We DiscussThis episode is for you if...
How long does it usually take to get pregnant?
The episode discusses how conception can take several months, even for couples in their twenties with no known fertility issues. A first-month pregnancy is not the only normal outcome.
Is pregnancy something you can plan?
You can plan when you'd ideally like to start trying, but you can't guarantee when conception, pregnancy, or motherhood will happen. Your body may not follow the timeline you've created.
Is miscarriage common?
Yes. The episode discusses how pregnancy loss is more common than many people realize and why it deserves more open conversation and support.
Does age affect fertility?
Age can affect fertility, particularly as egg quantity and quality naturally decline over time. That doesn't mean pregnancy isn't possible later in life, but it is something to consider when thinking about family planning.
Does fertility only depend on the woman?
No. The episode emphasizes that male fertility is an important part of conception and infertility, too.
Why does social media make trying to conceive harder?
Social media tends to show pregnancy announcements, bump updates, births, and happy moments without showing the struggles that may have happened behind the scenes. This can make you compare your entire journey to someone else's highlight reel.
What should I do if I'm struggling to get pregnant?
The episode encourages you to talk with appropriate professionals, including your OBGYN or a reproductive endocrinology and infertility specialist, as well as trusted people in your life. Your individual situation deserves individualized guidance.
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 Christiane Palpant:
Website: https://www.cuethelifeboat.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
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 twenties can feel so confusing after college—and why that uncertainty is actually a normal part of adulthood. We dive into the pressure to have everything figured out, how social media makes us feel like we're falling behind, and why comparing your timeline to someone else's only adds to the confusion.
We also explore one of the biggest questions every twenty-something faces: How do you know when it's time to keep going versus change directions? Professor CP shares practical questions you can ask yourself when you're feeling stuck, while I share how I've navigated career pivots, entrepreneurship, and the unexpected twists that ultimately led me to coaching.
Whether you're a recent graduate, questioning your career path, or simply wondering if you're doing adulthood "right," this conversation is a reminder that there is no perfect timeline—and that's exactly what makes your journey your own.
In This Episode We DiscussThis episode is for you if...
Why does life after graduation feel so hard?
Because the structure you've followed for years suddenly disappears, leaving you to make decisions without a clear roadmap.
How do I know if I should change careers?
Look beyond temporary frustration and ask whether your current path aligns with your values, supports your growth, and protects your well-being.
Is it normal to feel behind in your twenties?
Absolutely. Everyone's timeline looks different once college ends, even if social media makes it seem otherwise.
Does my college degree determine my career?
Not at all. Many people build careers outside of their major while still using the skills they developed in college.
Should I follow my passion?
Passion is important, but it doesn't always have to be the thing that pays your bills. Sometimes your job funds the life you're trying to build.
Related EpisodesHelpful 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 Christiane Palpant:
Website: https://www.cuethelifeboat.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
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 from reaching out, why those thoughts feel so convincing, and how to start building genuine relationships without feeling salesy or transactional. Because the people who can change the direction of your career and life are often the ones you haven't met yet.
Key Takeaways:
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
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 standards you're bringing into your relationships. We'll talk about the difference between having high standards and having double standards, uncover some common relationship blind spots, and explore what it really means to show up for someone you love. This isn't about settling or lowering your expectations—it's about pairing those expectations with self-accountability.
Key Takeaways:
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
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 focus, your productivity, and your relationships. This episode talks about the hidden damage your phone is creating in your life, tactics to separate yourself from your handheld device, and reminders that the virtual world is not nearly as important as the real world. Because yes, they are different.
Key Takeaways:
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
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