Skip to content
Artwork for how to twenty-something
EducationSelf-ImprovementHow ToHealth & FitnessExplicit

how to twenty-something

Jess Diamond

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.

Play
  • 29 episodes
  • weekly
  • Avg 22 min
  • English
Counted on this page — what you have heard stays on this device, so it is not something the list can be paged by.
  • #177
    Monday · 14 min

    Ep. 177 Getting Over a Slump

    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 goal, or building something of your own, but you feel like you’re completely stuck. I share what my own slump has looked like after my TEDx Talk, when I expected all of my hard work to lead to new clients and speaking opportunities and instead found myself wondering what the hell I was doing wrong. But here’s the thing: not getting the result you want doesn’t automatically mean you’re doing something wrong. Sometimes you need to change your strategy. Sometimes you need to be patient. Sometimes you need to recognize all the progress you’ve made that isn’t showing up in the form of the big outcome you’re waiting for. I also talk about why adulthood can feel so frustrating when you’re used to getting constant feedback, how to give yourself more objective feedback, why your slump can start to become part of your identity, and the questions you can ask yourself when you need to get moving again. Because your slump doesn't define you. And you don’t have to wait until you stop feeling disappointed to start taking action. In This Episode We Discuss What a slump actually looks and feels like Why you can do everything "right" and still not see results How to know when you need to change your strategy Why adulthood comes with significantly less feedback than you're used to Why progress isn't always measured by the big outcome you're waiting for The danger of letting a slump become part of your identity Questions to ask yourself when you're feeling stuck Why you need to keep taking action even when you're disappointed Understanding the lag between taking action and seeing results Key Takeaways Not getting the result you want and doing something wrong are two very different things. If you keep doing the exact same thing and expecting a different result, it's time to change your strategy. Adulthood comes with significantly less feedback than school, sports, and other structured environments you're used to. You have to learn how to give yourself objective feedback instead of relying entirely on external validation. The big outcome you're waiting for isn't the only measure of progress or success. Look at what you've learned, who you've met, what you've improved, and what you've actually done. New strategies need time to work, so give yourself room to see the results. You can be frustrated, disappointed, and upset while still choosing to move forward. Frequently Asked Questions What is a slump? A slump is that frustrating feeling of being stuck in the same place despite putting in consistent effort toward something you want. You aren't necessarily moving backward, but you aren't seeing the progress you expected either. How do I know if I'm doing something wrong or just experiencing a slump? Look at your actions objectively. If you've been doing the same thing repeatedly with no results, it may be time to change your strategy. But if you've been consistently taking action, learning, adapting, and trying new things, the lack of an immediate result doesn't automatically mean something is wrong. How do I stay motivated when I'm not seeing progress? Instead of measuring yourself exclusively by the big outcome you're waiting for, look at what you've actually done. Who have you met? What have you learned? What have you improved? What actions have you taken? Those are forms of progress, too. Why does adulthood feel like it has so little feedback? For most of your childhood and young adulthood, you're constantly given feedback through grades, sports, rankings, teachers, parents, and other structured systems. Once you become an adult, there isn't a report card telling you how you're doing. You have to learn how to create some of that feedback for yourself. How do I stop my slump from becoming my identity? Be careful about turning an experience into a statement about who you are. Not getting a job doesn't mean you're bad at getting jobs. Being single doesn't mean you're unlovable. A business being slow doesn't mean you're a bad entrepreneur. Your current circumstances are not your identity. How long does it take to get out of a slump? There isn't a set timeline. Sometimes changing your strategy creates a faster result, while other times you need to allow more time for your actions to catch up. The important thing is continuing to take intentional action rather than allowing yourself to stay stuck indefinitely. What if I'm still disappointed even after I start taking action? You can be disappointed and still take action. You don't have to wait until you feel positive, motivated, or confident before doing something that could improve your situation. Helpful Resources: Let’s chat: https://calendly.com/coach_jessdiamond/success 3 ways to stop spiraling: https://jessdiamondcoaching.com/spiral/ Email Me: coach.jessdiamond@gmail.com 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

    • Transcript
  • #176
    October 26 · 15 min

    Ep. 176 Deciding to be child free

    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 actually get to make. I share my own experience of growing up assuming I'd become a mom, realizing in college for the first time that motherhood was a choice, and eventually landing somewhere in the middle where having kids isn't a requirement for me to have a fulfilling life. I break down some of the reasons people choose to have kids, including wanting to build a family, create a legacy, contribute to the next generation, avoid missing out, or simply because they want to. I also talk about why more people are questioning parenthood, including the financial cost, career sacrifices, and desire to maintain the freedom and lifestyle they currently have. But deciding whether or not to have kids isn't as simple as a yes or no. I also break down some of the traps to watch out for and why this is not a decision that has to be made right now. The important reminder here is: you get to choose the life you actually want. Who This Episode Is For This episode is for you if... You're not sure whether you want children. You're firmly in the child-free camp and feel like you constantly have to explain yourself. You're dating someone who has a different opinion about having kids. You're worried you'll regret whatever decision you make. You're in your twenties and feel like you need to make a permanent decision right now. Key Takeaways Having children is a choice, not an automatic box to check off in adulthood. You can create a fulfilling life with or without children. People choose to have children for many different reasons, and those reasons are worth examining for yourself. Having kids shouldn't be your only source of purpose or identity. You don't need a complicated justification for choosing not to have children. "I don't want kids" is a complete answer. Fear of parenthood and genuinely not wanting children are two different things. If your stance on kids only exists because of who you're dating, you may be holding a borrowed opinion. You are allowed to change your mind as you grow and your circumstances change. You don't have to figure out your entire future in your twenties. Frequently Asked Questions Do I have to decide if I want kids in my twenties? No. The episode emphasizes that you don't have to treat your current opinion as a permanent decision. You can feel differently at 24 than you do at 32, and you're allowed to change your mind as you grow. Is it okay to not want children? Absolutely. You don't need to justify your decision to other people. Not wanting children is a valid choice and doesn't require a more complicated explanation. What if my partner wants kids and I don't? This is a conversation that needs to happen early and be revisited throughout the relationship. You shouldn't stay with someone hoping they'll eventually change their mind, and you shouldn't expect yourself to change either. How do I know if I actually don't want kids? Consider whether your decision comes from genuine desire or from fear, your current relationship, financial concerns, societal expectations, or assumptions about what adulthood is supposed to look like. Giving yourself space to separate your own opinion from everyone else's can help. What if I'm afraid I'll regret not having kids? That fear is worth exploring rather than automatically treating it as proof that you want children. The episode encourages you to distinguish between genuinely desiring parenthood and being afraid of making the wrong choice. Helpful Resources: Let's chat: https://calendly.com/coach_jessdiamond/success 3 ways to stop spiraling: https://jessdiamondcoaching.com/spiral/ Email Me: coach.jessdiamond@gmail.com 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_]()

    • Transcript
  • #175
    October 19 · 13 min

    Ep. 175 Quality Over Quantity

    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 approach to networking, and how you can apply that same mentality to your dating life, friendships, and job search. We'll talk about how to be more intentional with the people you meet, why dating apps can trick you into thinking there's always someone better around the corner, and how spending five hours on one well-researched job application might get you further than sending out 100 applications. Because putting yourself out there is important, but you can't keep looking for more opportunities when you haven't done anything with the ones you already have. Who This Episode Is For This episode is for you if... You're constantly applying to jobs but aren't seeing results. You're on dating apps, going on dates, and still feel like you're getting nowhere. You attend networking events but struggle to turn acquaintances into meaningful connections. You know a lot of people but don't feel like you have many close friendships. You feel pressure to do more because everyone keeps telling you it's a numbers game. You spend more time meeting new people than following up with the people you've already met. You want to build better relationships but aren't sure how to move beyond small talk. You're measuring your progress by how many applications you send, events you attend, or dates you go on. You're ready to stop checking boxes and start being more intentional with your time and effort. Key Takeaways Quantity can get you opportunities, but quality is what helps you make something meaningful out of them. You don't always need to meet more people. Sometimes you need to get to know the people you've already met. In networking, a meaningful conversation and a follow-up coffee can be more valuable than collecting 30 business cards. Focusing on fewer matches and asking better questions can lead to more meaningful dating experiences. Building friendships requires more than attending events and making small talk Stop measuring progress exclusively by numbers. Consider the time, effort, and thought you're putting into the process. Before attending another networking event, reaching out to more people, or applying to more jobs, ask yourself whether you've followed up on the opportunities you already have. Being genuinely interested in someone makes a difference in the relationship you're building. You can have a packed calendar, tons of acquaintances, and hundreds of LinkedIn connections without having meaningful relationships or getting closer to your goals. The goal isn't to stop putting yourself out there. It's to be more intentional when you do. Frequently Asked Questions Is job searching really a numbers game? There is a quantity component to job searching, but sending more applications isn't always the best use of your time. Researching companies, tailoring your resume, connecting with people in your industry, and following up can make your applications more intentional and help you build valuable relationships. How can I make networking events more productive? Instead of trying to meet everyone in the room, focus on having meaningful conversations with one or two people. Ask thoughtful questions, remember details about their lives, and follow up afterward. The goal is to build a relationship, not collect business cards. How can I stop treating dating like a numbers game? Try investing more time in fewer matches instead of having the same surface-level conversation with 15 people at once. Ask better questions, genuinely try to get to know someone, and give the connection an opportunity to develop before immediately moving on to the next option. Should I focus on quality instead of quantity when applying for jobs? Rather than sending as many applications as possible, spend time researching companies you're genuinely interested in, tailoring your resume, finding relevant connections, and following up. A smaller number of thoughtful applications can be a better use of your time than sending out applications without much consideration. How do I know when I need to do more versus do better? Before adding another task, event, application, or date to your calendar, look at what you've already done. Have you followed up with the people you met? Have you strengthened existing connections? Have you improved your approach? Sometimes the next step isn't doing more. It's getting more intentional about what you're already doing. Helpful Resources: 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 3 Ways to Walk Into Any Room With Confidence: https://jessdiamondcoaching.com/confidence Let's chat: https://calendly.com/coach_jessdiamond/success Email Me: coach.jessdiamond@gmail.com 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

    • Transcript
  • #174
    October 12 · 16 min

    Ep. 174 Why is it so hard to ask for help

    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 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 For You hate asking people for help, even when you know you need it. You feel like you're supposed to have everything figured out because you're an adult. You'd rather struggle on your own than admit you don't know what you're doing. You're afraid of being a burden to your friends, family, coworkers, or boss. You're the "strong friend" who is always helping everyone else. You're navigating something for the first time and don't know where to start. You struggle with vulnerability or opening up about what's actually going on. You need help but keep convincing yourself you should be able to figure it out alone. Key Takeaways We all need help with something; it's just a matter of how willing we are to ask for it. Asking for help doesn't mean you're weak, incapable, or don't have your shit together. When you're experiencing something for the first time, there's no reason you should already know how to navigate it. Asking someone who is a few steps ahead of you can help you get where you're going faster and easier. Vulnerability is a muscle, and you build it through practice. Get clear on the kind of help you need before asking someone for it. Make sure you're asking the person who is actually equipped to help you. Don't assume someone doesn't have the capacity to help you. Let them decide that for themselves. You don't have to navigate your twenties alone. Frequently Asked Questions Why 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: coach.jessdiamond@gmail.com 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

    • Transcript
  • #173
    October 5 · 57 min

    Ep. 173 Stop waiting for permission in your career with Austin Lutz

    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 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 Takeaways You don't have to wait for someone else to give you permission to pursue the career you want. A calculated risk isn't about throwing your life into chaos—it's about understanding the potential risks, rewards, and outcomes before making a decision. Being busy doesn't necessarily mean you don't have time. You have to intentionally decide where your time goes. You don't have to abandon an idea just because the first version isn't working. Sometimes you need to reframe it. Your friends and family can be your cheerleaders, but you also need people who are willing to challenge your ideas and tell you the truth. The people you meet throughout your career can become future mentors, collaborators, employers, or opportunities. What you do outside of your full-time job can teach you skills that make you better at your full-time job. Your full-time job can also help you develop the skills you need to eventually pursue entrepreneurship or another career path. You don't need to work more hours to prove yourself. Focus on improving the quality of your work and building skills. Don't tie your self-worth to your job title, salary, or promotion. Doing nothing is still a decision, and it won't move you any closer to the career or life you want. Frequently Asked Questions How 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: coach.jessdiamond@gmail.com 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

  • #172
    September 28 · 15 min

    Ep. 172 Nothing Changes If Nothing Changes

    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 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 For This episode is for you if... You're unhappy with your job, relationship, city, or current situation but haven't done anything to change it. You keep complaining about the same problem over and over again. You know what you should do but keep finding reasons not to do it. You're afraid that making a change will make things worse. You feel trapped because you've already invested so much time, money, or energy into something. You keep waiting for someone else to change. You're wondering whether the problem is actually your circumstances or your mindset. You need a little tough love to finally take your next step. Key Takeaways Being unable to change your circumstances is different from being unwilling to change them. Your brain often prefers familiar misery over unfamiliar possibility. Complaining can become a substitute for actually taking action. Waiting for someone else to change is not a strategy. Staying somewhere simply because you've already invested in it can keep you stuck. Getting specific about what's making you unhappy makes the problem more solvable. If the same problems follow you everywhere, you may need to look at your own patterns. You can't control everything about your situation, but you can control your response, boundaries, requests, and next steps. You don't have to know exactly how everything will work out before you make a change. Readiness isn't something that magically arrives—you often have to do it scared. You don't need to change your entire life today. Focus on the next 1%. Accountability can help you stop negotiating with your own excuses and actually follow through. Frequently Asked Questions 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: coach.jessdiamond@gmail.com 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

    • Transcript
  • #171
    September 21 · 17 min

    Ep. 171 Why Relatability Matters More Than Advice in Your Twenties

    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 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 Discuss Why relatability can matter more than generic advice The difference between someone who sympathizes and someone who "gets it" How your life experiences shape the advice that's actually relevant to you How to find people who relate to your current season of life Why you shouldn't expect one person to understand every part of your life Who This Episode Is For This episode is for you if... You feel like the people around you don't fully understand what you're going through. You keep getting advice that doesn't actually resonate with your situation. You've grown apart from friends because you're on completely different life paths. You're struggling to explain why something feels so difficult when everyone else seems to think it's simple. You find yourself comparing your experience to people who are in a completely different season of life. You're looking for a coach, therapist, mentor, or community that actually understands your perspective. You want to build a stronger support system in your twenties. You're tired of trying to figure everything out by listening to people who haven't experienced what you're experiencing. Key Takeaways You don't always need more advice; you need someone who understands your experience. Relatability isn't necessarily about age; it's about shared context and experience. The world changes, which means advice that worked decades ago may not work in the same way today. You shouldn't expect one friend, partner, parent, therapist, or coach to understand every part of your life. Ask people for advice when they're actually on the same road you're traveling. Having people who "get it" can make you feel less alone in experiences that otherwise feel isolating. As you move through different phases of life, the people who understand your current season may change. Find your people—the ones you don't have to constantly explain yourself to. Frequently Asked Questions 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: coach.jessdiamond@gmail.com 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

    • Transcript
  • #170
    September 14 · 15 min

    Ep. 170 What it really means to Own Your Life

    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 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 Discuss What it actually means to own your life Where the Own Your Life System came from Breaking out of the "good girl" mentality Why following the path you're "supposed" to take can leave you feeling stuck Taking action before you have everything figured out Making decisions based on your own values instead of other people's expectations Taking responsibility for your life without blaming yourself for everything Why consistency matters more than motivation How to respond when things go wrong What it feels like when your life actually starts to feel like yours Who This Episode Is For This episode is for you if... You're questioning whether the life you're living is actually the one you want. You feel like you're following a path because it's what you're "supposed" to do. You're constantly looking to other people for permission or validation. You know you want something different but don't know exactly what that looks like yet. You're ready to take more responsibility for the direction of your life. You want to stop waiting for motivation, certainty, or the perfect time to make a change. Key Takeaways Owning your life doesn't mean having a five-year plan or knowing exactly where you're headed. Your decisions should be based on what you want, not what you're told to want. You can question the status quo without having the entire alternative figured out. Taking action creates options and can help you discover what you actually want. Owning your life means taking responsibility for what you can control. Consistency and systems will carry you further than waiting for motivation. When things go wrong, curiosity is more productive than blame. Your definition of success doesn't have to look like anyone else's. Your life can be messy and still be completely yours. Owning your life isn't a destination—it's a decision you make over and over again. Frequently Asked Questions 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: coach.jessdiamond@gmail.com 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

    • Transcript
  • #169
    September 7 · 17 min

    Ep. 169 What No One Tells You About Getting Pregnant

    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 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 Discuss Why you can't perfectly plan pregnancy or motherhood How long it can actually take to conceive What to expect when coming off birth control The reality of miscarriage and pregnancy loss How age can impact fertility Why male fertility matters, too The different factors that can affect conception How social media creates unrealistic expectations around pregnancy Why comparing your fertility journey to someone else's isn't helpful The importance of talking openly about fertility and pregnancy loss Who This Episode Is For This episode is for you if... You're thinking about having kids someday and want to understand what the journey can actually look like. You're starting to think about family planning in your twenties or thirties. You're currently trying to conceive and need a reminder that everyone's timeline is different. You've experienced pregnancy loss and have felt alone in that experience. You find yourself comparing your fertility journey to what you see online. You want to have more informed conversations about fertility before you're ready to have kids. Key Takeaways Pregnancy isn't something you can plan as precisely as the other milestones in your life. Getting pregnant can take longer than you expect, even when there are no known fertility issues. Coming off birth control doesn't necessarily mean you'll immediately conceive. Pregnancy loss is common, but many people experience it privately and don't talk about it. Fertility is influenced by many factors, and your journey may look completely different from someone else's. Age can affect fertility, which is worth considering when you're thinking about family planning. Male fertility is an important part of the conversation and contributes to a significant portion of infertility cases. Social media only shows you one side of someone's pregnancy journey. Comparing your behind-the-scenes to someone else's highlight reel can make an already difficult experience feel even more isolating. Talking to medical professionals and people you trust can help you feel less alone and better understand your individual situation. Frequently Asked Questions 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: coach.jessdiamond@gmail.com 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

    • Transcript
  • #168
    August 31 · 57 min

    Ep. 168 The Truth About Life After Graduation with Christiane Palpant

    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 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 Discuss Why life after graduation feels so overwhelming The myth that adulthood follows a linear path How to know when it's time to pivot versus push through Why so many twenty-somethings feel behind The value of mentors and "hidden allies" Why your college degree doesn't have to determine your career The difference between following your passion and funding your passion Letting go of the "shoulds" that keep you stuck Who This Episode Is For This episode is for you if... You're about to graduate college or recently graduated. You're wondering if you're on the right career path. You feel behind compared to your friends. You're debating whether to quit your job or stick it out. You're navigating a quarter-life crisis and don't know what's next. Key Takeaways Life after graduation is rarely as straightforward as we expect. Feeling uncertain doesn't mean you're doing anything wrong. Use your values—not fear—to decide when it's time to pivot. Every career experience teaches transferable skills. Your degree doesn't have to define your future. Social media is not an accurate measure of success. Seeking advice is different from copying someone else's path. Growth often comes from the challenges you'd never choose for yourself. Your passion doesn't always have to be your paycheck. Let go of the timeline you think you're supposed to follow. Frequently Asked Questions 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 Episodes 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 3 ways to stop spiraling: https://jessdiamondcoaching.com/spiral/ Email Me: coach.jessdiamond@gmail.com 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

  • #167
    August 24 · 20 min

    Ep. 167 The connections you're missing out on by staying comfortable

    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: Every connection starts with one uncomfortable action, whether that's sending a message or showing up to an event. Make sure you don’t say no for the other person, before they even have a chance to possibly say yes. Understanding the different fears that come with making new connections. Networking doesn’t have to only be at a formal event, it can be at a run club too! Why asking for help isn't a burden at all. Helpful Resources: Let’s chat: https://calendly.com/coach_jessdiamond/success How to stop spiraling: https://jessdiamondcoaching.com/spiral/ Email me: coach.jessdiamond@gmail.com 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

    • Transcript
  • #166
    August 17 · 16 min

    Ep. 166 Are you the partner you want to date?

    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: Identify what qualities you want in your relationship Why high standards should always be paired with high self-accountability How presence is one of the most underrated ways to strengthen a relationship How to see your blindspots, when they are blind to you How to become accountable to the things you say you want in someone else Helpful Resources: Let’s chat: https://calendly.com/coach_jessdiamond/success How to stop spiraling: https://jessdiamondcoaching.com/spiral/ Email me: coach.jessdiamond@gmail.com 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

    • Transcript
  • #165
    August 10 · 21 min

    Ep. 165 Get Unplugged: How to Break Your Phone Addiction

    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: Different ways your phone is messing with your focus, thought patterns, and productivity Why physical connections is more valuable than digital ones What boredom does for you that your phone cannot How to separate yourself from your phone in little ways Why your phone is your coping mechanism and is destroying your mental health Helpful Resources: Let’s chat: https://calendly.com/coach_jessdiamond/success How to stop spiraling: https://jessdiamondcoaching.com/spiral/ Email me: coach.jessdiamond@gmail.com 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

    • Transcript
  • #164
    August 3 · 16 min

    Ep. 164 When is it time to work with a coach?

    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 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. In This Episode We Discuss 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 Who This Episode Is For 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. Key Takeaways 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. Frequently Asked Questions 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: coach.jessdiamond@gmail.com 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

    • Transcript
  • #163
    July 27 · 18 min

    Ep. 163 This is not your forever, but it is your for now

    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 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. In This Episode We Discuss 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 Who This Episode Is For 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. Key Takeaways 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. Frequently Asked Questions 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. Related Episodes 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: coach.jessdiamond@gmail.com 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

    • Transcript
  • #162
    July 20 · 1 hr

    Ep. 162 This is why you operate the way you do with Adrienne Craighead

    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: How to use human design as a another tool in your tool box What your chart says about you 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: coach.jessdiamond@gmail.com 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

  • #161
    July 13 · 18 min

    Ep. 161 How to talk to your parents so they actually hear you

    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: coach.jessdiamond@gmail.com 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

    • Transcript
  • #160
    July 6 · 16 min

    Ep. 160 Is Gen-Z really screwed in the job market?

    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: coach.jessdiamond@gmail.com 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

    • Transcript
  • #159
    June 29 · 15 min

    Ep. 159 The Psychology Behind Your Quarter Life Crisis

    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: Why quarter life crises are so common in your twenties The psychological and emotional changes happening between 18–30 How social media distorts your perception of success and timing The role your prefrontal cortex plays in decision-making Why feeling lost can actually be a sign of growth How to tell the difference between impulsivity and intuition What to do when you feel the urge to completely change your life Why you don’t need a full life plan — just the next step 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: coach.jessdiamond@gmail.com 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

  • #158
    June 22 · 18 min

    Ep. 158 This is your sign to lift weights

    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: Why your twenties are the best decade to get started in the gym Waiting to lift weights comes at a cost The most common fears talking you out of going to the gym You don’t need to spend hours in the gym to see results The simple framework to help you walk in the gym with a plan 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: coach.jessdiamond@gmail.com 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

Showing 1–20 of 29 episodes