Trying Very Hard: The Podcast

Building Your Own Modern Village: On Moving Countries, Burnout, & Belonging (with Alka Gupta)

Why is making friends as an adult so hard — especially when you've just moved somewhere new and don't know a single person? In this episode of Trying Very Hard, we talk to Alka Gupta, founder of Podium, about exactly that. And about the years of burnout, identity loss, and starting over that got her there. Alka shares the story of LinkedIn-messaging strangers for friendship, a Bumble BFF match that became her entire Jakarta circle, and what she calls building a "modern village" when the one you grew up with is gone. We also talk about the decision that changed everything — a 70% pay cut to join a startup she loved — and the founder burnout and layoffs that followed. Alka walks us through her practice of writing emails to her future self before big life decisions, and why "work-life balance" might be the wrong goal entirely — harmony, not balance, is what she's chasing now. If you've ever moved to a new city and had to build your social life from scratch, felt burnt out by something you used to love, or are quietly questioning whether "balance" is even real, come sit with us. Follow Alka: Podium Instagram: https://www.instagram.com/podium.women/ [https://www.instagram.com/podium.women/] https://podiumsociety.com/ [https://podiumsociety.com/] https://www.linkedin.com/in/alka-gupta-ag/ [https://www.linkedin.com/in/alka-gupta-ag/] Follow us: Instagram: https://www.instagram.com/tryingveryhardpod/ [https://www.instagram.com/tryingveryhardpod/] YouTube: https://www.youtube.com/@TryingVeryHardPod [https://www.youtube.com/@TryingVeryHardPod] Spotify: https://open.spotify.com/show/4kQL0nJmPhv38D8io58eMX [https://open.spotify.com/show/4kQL0nJmPhv38D8io58eMX] Apple Podcasts: https://podcasts.apple.com/sg/podcast/trying-very-hard-the-podcast/id1878052269 [https://podcasts.apple.com/sg/podcast/trying-very-hard-the-podcast/id1878052269] Website: https://www.tryingveryhard.com/ [https://www.tryingveryhard.com/]

Stop Diagnosing Your Ex: How Attachment Styles & Love Languages Became a Trap

You've taken the quiz. You know your attachment style. You've told a date your love language. So why does it feel like none of it is actually helping? In this Monanda episode of Trying Very Hard, Amanda and Monica talk honestly about the attachment style and love language frameworks everyone's obsessed with, and why they think both are being used in exactly the wrong way. From diagnosing exes to weaponizing "You're avoidant" in arguments, to the way love language labels quietly let you off the hook for showing up creatively — we go there. We also get personal. Monica on becoming anxious in a relationship where she was otherwise completely secure. Amanda on chasing someone mid-argument despite knowing he'd asked for space. Both of them on what it actually felt like to have these labels used against them. The real conversation: you are not your attachment style. It's situational, it's dynamic, and most importantly, you're not stuck in it. If you've ever felt put in a box mid-argument, or quietly used a label to excuse someone else's behavior, this one will feel very familiar. Come sit with us. Follow us: Instagram: https://www.instagram.com/tryingveryhardpod/ [https://www.instagram.com/tryingveryhardpod/] YouTube: https://www.youtube.com/@TryingVeryHardPod [https://www.youtube.com/@TryingVeryHardPod] Spotify: https://open.spotify.com/show/4kQL0nJmPhv38D8io58eMX [https://open.spotify.com/show/4kQL0nJmPhv38D8io58eMX] Apple Podcasts: https://podcasts.apple.com/sg/podcast/trying-very-hard-the-podcast/id1878052269 [https://podcasts.apple.com/sg/podcast/trying-very-hard-the-podcast/id1878052269] Website: https://www.tryingveryhard.com/ [https://www.tryingveryhard.com/]

Inside the Life of a Football Agent: On Contracts, Resilience and the +1 / -1 Rule (with Matthew Moore)

Ever romanticized a career that looks glamorous from the outside? In this episode of Trying Very Hard, Monanda sit down with Matthew Moore — football agent, South African globetrotter, and Monica's one true college friend — to find out what the job actually looks like behind the scenes. Matthew has spent his career negotiating contracts, managing young players' mental states, designing Puma boot collections in Milan, and racking up enough Marriott nights to never pay full price again. We talk about how he got in (hint: fake Twitter accounts and a 16-year-old with hustle), what it takes to stay in (contacts, grit, and face-to-face everything), and the one framework he gives every player he signs: stay between +1 and -1. We also go somewhere more honest: what it means to grow a thicker skin without losing yourself, whether numbness is a coping mechanism or a cost, and the blurred line between a career you love and a life you're neglecting. Plus: why AI won't replace the football agent, what growing up across South Africa, Spain, and Boston teaches you about resilience, and the Japanese language goal he's blaming on business expansion (we believe him, mostly). If you've ever built — or wanted to build — something unconventional, or just wondered what it looks like to succeed in an industry nobody explains, come sit with us. Follow us: Instagram: https://www.instagram.com/tryingveryhardpod/ [https://www.instagram.com/tryingveryhardpod/] YouTube: https://www.youtube.com/@TryingVeryHardPod [https://www.youtube.com/@TryingVeryHardPod] Spotify: https://open.spotify.com/show/4kQL0nJmPhv38D8io58eMX [https://open.spotify.com/show/4kQL0nJmPhv38D8io58eMX] Apple Podcasts: https://podcasts.apple.com/sg/podcast/trying-very-hard-the-podcast/id1878052269 [https://podcasts.apple.com/sg/podcast/trying-very-hard-the-podcast/id1878052269] Website: https://www.tryingveryhard.com/ [https://www.tryingveryhard.com/]

Do You Want Kids? On Choosing Parenthood, Social Pressure, and Inherited Expectations

Did you decide to have children — or did you just assume you would? In this episode of Trying Very Hard podcast, Amanda and Monica get honest about having kids, not having kids, maternal ambivalence, and the default most of us never question. Amanda is visibly pregnant. Monica has always assumed she'd want kids but has had her doubts. Together they unpack the default assumption that most of us inherited, the quiet fear of saying out loud that you're uncertain, and why the people who've decided not to have kids have usually thought about it harder than anyone. They get into maternal ambivalence, the career disruption nobody prepares you for, the resentment that's too hard to admit, the biological clock and egg freezing, and the big question underneath it all: can you ever really be ready? No judgment. No right answer. Just two friends trying to figure out whether the lives they're building are actually theirs. Follow us: Instagram: https://www.instagram.com/tryingveryhardpod/ YouTube: https://www.youtube.com/@TryingVeryHardPod Spotify: https://open.spotify.com/show/4kQL0nJmPhv38D8io58eMX Apple Podcasts: https://podcasts.apple.com/sg/podcast/trying-very-hard-the-podcast/id1878052269 Website: https://www.tryingveryhard.com/

Who Are You Without Your Job? On Burnout, Career Identity, and Starting Over (with Sandra Wang)

Who are you without your job title? It's a question most high achievers never stop long enough to ask. Sandra Wang did — not by choice, but because burnout and a pandemic layoff left her with nothing else to sit with. In this episode of Trying Very Hard, the life and career coach and founder of The Kind Mind (@thekindmindcoaching [https://www.instagram.com/thekindmindcoaching]) joins us to talk about career burnout, identity collapse, people pleasing, and what the slow, uncomfortable work of rebuilding actually looks like. We cover the hustle years — the startup grind, the validation loop, the moment her friends thought she owned her boss's company because she was so attached to it. We cover the crash — the weight fluctuations, the sleepless nights, the "who am I without a role" spiral that therapy and coaching helped her name. And we cover what came after — the ICF certification, the quiet pivot, the practice she built rooted in self-compassion, and the therapist who recently told her she has a healthy nervous system. She asked her to say it again. If you've ever tied your self-worth to your output, struggled to switch off, or realised the inner voice you've been living with is meaner than anything you'd say to a friend — this one will hit. Follow Sandra: Instagram: https://www.instagram.com/thekindmindcoaching [https://www.instagram.com/thekindmindcoaching] Follow us: Instagram: ⁠⁠⁠https://www.instagram.com/tryingveryhardpod/⁠⁠⁠ [https://www.instagram.com/tryingveryhardpod/⁠⁠⁠] YouTube: ⁠⁠⁠https://www.youtube.com/@TryingVeryHardPod⁠⁠⁠ [https://www.youtube.com/@TryingVeryHardPod⁠⁠⁠] Spotify: ⁠⁠⁠https://open.spotify.com/show/4kQL0nJmPhv38D8io58eMX?si=fb23804978884406⁠⁠⁠ [https://open.spotify.com/show/4kQL0nJmPhv38D8io58eMX?si=fb23804978884406⁠⁠⁠] Apple Podcasts: ⁠⁠⁠https://podcasts.apple.com/sg/podcast/trying-very-hard-the-podcast/id1878052269⁠⁠⁠ [https://podcasts.apple.com/sg/podcast/trying-very-hard-the-podcast/id1878052269⁠⁠⁠] Website: ⁠⁠⁠https://www.tryingveryhard.com/ [https://www.tryingveryhard.com/]