WIP'n & Reppin'

About WIP'n & Reppin'

Most of us build a life we thought we wanted — then one day look up and think: hang on, is this actually it? WIP'n & Reppin' is for anyone in that moment. Reframing setbacks, building confidence, asking for what you want, moving your body for your mind — basically everything that helps you build a life that genuinely fits you. Not about perfection but about doing the reps — on your terms! WIP — Work In Progress. Reppin' — showing up for it anyway. No fluff. No lectures. Fortnightly. Hosted by Holly — architect, developer and career pivoter - who learned most of this the hard way.

Publisher

with Holly

Category

education

Language

en

Explicit

No

First episode

14 May 2026

Latest episode

25 Oct 2026

Latest episodes

16 episodes in the feed.

1. 

   25 Oct 2026

   15. Changing Careers and Don’t Know Who You Are? (Spoiler: Still You)

   If your pivot or career change is making you feel like you don't know who you are anymore - this episode might lighten things up for you! Here’s what I’ve come to think: it’s probably not an identity crisis at all. Your identity was never fixed. You’ve been changing your whole life, you just never realised! In this short episode, I pull apart the question that keeps coming up for me and for nearly every woman I talk to who is changing something big: how do I know I can be the new version of me? What feels like one big identity crisis is usually four everyday fears about doing something new, stacked on top of each other. Separate them, and each one gets a lot smaller. In this episode: Why your identity was never as fixed as it feels, and the difference between your personality and the story you tell about it The four fears hiding underneath: not knowing, the pull of old habits, fear it won’t work, and what people will think Why slipping back into old habits is like hunting for lost keys (and why that’s nothing to beat yourself up about) Why you’re judging your new idea with the wrong evidence Three light experiments to help you practise the new you, without the pressure Chapters 00:00 How do I know I can be the new version of me?01:00 Welcome, and is it really an identity crisis?02:00 Your identity was never fixed05:15 The four fears underneath05:30 Fear one: not knowing07:00 Fear two: the pull of old habits (the lost keys)08:30 Fear three: that it won’t work09:45 Fear four: what other people will think11:00 Two things that help14:00 So, is it really an identity crisis?15:30 Three little experiments to try Secret pivot soirées. Small, private, in-person evenings in London for women working out what’s next. What’s said there stays there. Request an invite here (https://tally.so/r/yXPylW) Connect with meInstagram: @wipn_reppin (https://www.instagram.com/wipn_reppin/)Email: wipitandrepit@gmail.com (mailto:wipitandrepit@gmail.com)Substack: wipitandrepit.substack.com (https://wipitandrepit.substack.com/)Want to be a guest? Apply here (https://tally.so/r/7Xlkj0) Listen and follow on Spotify: https://open.spotify.com/show/4tTC90CyLRtmpnDoqgIJzl (https://open.spotify.com/show/4tTC90CyLRtmpnDoqgIJzl) If this episode helped, share it with a friend who’s in the middle of a big change, and leave a rating so more women can find the show. Mentioned in this episode: the Oxford dictionary definition of identity, Tony Robbins, Brené Brown, Lisa Feldman Barrett, Wendy Wood, Herminia Ibarra, Bob Proctor, the “end of history illusion” study, UCL’s 2016 uncertainty study, and habit stacking (Atomic Habits, Tiny Habits, The Power of Habit, Gretchen Rubin’s Better Than Before). The values exercise from Episode 2 is on Substack.

2. 

   8 Oct 2026

   14. How to Plan a Career Pivot (Without Blowing Up Your Life)

   A career change doesn't have to mean quitting on Monday and hoping for the best. Everyone warns you about the big leap. Nobody warns you about walking briskly in the wrong direction, which is what I did first time round... This is the plan I wish I'd had: what to work out first, how much money you need behind you, and when to hand in your notice. I've laid out my notes in six stages, the way a building project runs, whether you're moving into a new role, retraining, going freelance or starting a business. Take what's useful and leave the rest. In this episode: (00:00) Walking briskly in the wrong direction: the pivot mistake nobody warns you about (02:51) Why we either leap with no plan or plan for years and never start (06:08) Stage 0 and the six stages of a career pivot (08:00) Stage 1: what you want from a career change, and getting your partner on board (11:14) Stage 1: what's structural in your life, from bills to the people who rely on you (13:48) Stage 2: testing a new career with the normal Tuesday test (18:54) Four routes: retrain, build alongside your job, save a runway and go, or a mix (20:43) Stage 3: the money, your monthly floor and your financial runway (23:45) The payment maths that caught me out when I started a business (25:31) Stage 4: what pays the bills while you change career (28:52) A state and a date: deciding in advance when to quit your job (30:16) Stage 5: on site, doing the work (32:09) Stage 6: the first months after you leave, and the daily anchors that help (34:40) The blueprint I wish I'd followed Mentioned in this episode: - Episode 2: the values exercise - Episodes 4 and 9: "do I actually want this, or do I think I should want it?" - Annie Duke, author of Quit: pairing a state with a date Get the one-page Pivot Blueprint on Substack (https://wipitandrepit.substack.com) A money checklist is coming there too, for moving into a new role and for setting up on your own. Fill yours in alongside mine and reply with your state and your date. I read every one. Let's keep WIP'n & Reppin' together! Connect with me:- Substack: https://wipitandrepit.substack.com (https://wipitandrepit.substack.com/)- Instagram: @hh_squared (https://www.instagram.com/hh_squared/)- Instagram: @wipn_reppin (https://www.instagram.com/wipn_reppin/)- LinkedIn: Holly H (https://www.linkedin.com/in/holly-harrington/)

3. 

   24 Sept 2026

   13. What pivoting & lobsters have in common; growing pains!

   Pivoting is like being a lobster...it grows its new shell under the old one before it breaks out. Your next version works the same way. If you've been wondering why going after the bigger thing feels so uncomfortable, this episode is for you. That could be a career change, starting your own business, or stepping up to the next level where you already are. If you keep reading one more book before you start… if you've outgrown a job title but don't know what to call yourself yet… if you've felt like running back to your comfort zone just as things start to change… you're in the right place. In this solo episode, Holly explains why a show about career pivots keeps coming back to personal growth. The life you're building can't stay bigger than the person holding it. Using a children's book, some surprising lobster biology, and a very unglamorous bad day in her property business, she explains why growing pains are usually a sign it's working, and how to tell them apart from the kind of pain that means you're in the wrong place. In this episode: Why your business or career can grow past you, and what happens when it does What lobsters can teach you about outgrowing an old identity Growing pain vs wrong-fit pain: how to tell the difference Why personal development can become the most sophisticated way of never starting The Stretch Check: three questions for when you're in the middle of it Chapters: 00:00 The Bear Hunt confession 01:30 Welcome to WIP'n & Reppin' 02:15 Why this show keeps making you do the inner work 05:30 The lobster and the old shell 08:30 What going through it looks like on a bad day 12:00 The Stretch Check 13:45 What's on the other side This week's question: What's the thing I keep trying to go round, and who would I have to become to go through it? Resources mentioned: Susan David, Emotional Agility Brené Brown, Dare to Lead Herminia Ibarra, Working Identity Tony Robbins, Awaken the Giant Within Noam Wasserman, "The Founder's Dilemma," Harvard Business Review (2008) Michael Rosen & Helen Oxenbury, We're Going on a Bear Hunt Lobster facts: NOAA Fisheries If this episode landed, listen next: Ep 9, "You know your values — so why aren't you acting on them?" Free values exercise: link (https://wipitandrepit.substack.com/p/do-your-daily-actions-match-your?r=8mparf&utm_campaign=post-expanded-share&utm_medium=web) Read more on Substack: https://wipitandrepit.substack.com/ Instagram: @wipn_reppin LinkedIn: https://www.linkedin.com/in/holly-harrington/ WIP'n & Reppin' is a podcast for women navigating career pivots, personal growth, and building a life that's theirs. New episodes every other Thursday. This podcast is not therapy or medical advice.

4. 

   10 Sept 2026

   12. Can you actually pivot your life with a family?

   She moved her whole family to Finland 1 month after launching her new business in London. Life just wasn't working. That's how Faith describes London in 2023 — two kids under five, a husband who was never home, a startup she was building from scratch, and a growing sense that something had to change. So she got out a whiteboard. Mapped family values on one side, real life on the other. Looked at what they'd written and thought: none of this matches. Fourteen months later, the whole family moved to Finland. This is a conversation about what deliberate pivots actually look like from the inside — not the polished version, the real one. In this episode: What Faith did before the move that most couples never do — and why she says it made everything else possible The moment she realised "not being on the property ladder" was actually the thing that bought her freedom Why building something meaningful rarely looks like a hockey stick — and what keeps you going on the days it feels like nothing is working How to build a team around you when you have no money, no co-founder, and no idea what you're doing yet What it actually feels like to arrive in a new country and realise you don't fully know who you are there yet The one question that cuts through every big life decision faster than any framework What we discuss: 00:00 — "Life just wasn't working" 02:30 — From disaster zones to diapers: Faith's journey before Nugget 08:00 — Building a startup in the middle of COVID, two kids, and an identity shift 16:00 — Why talking about your idea is the actual work (and the story behind the name Nugget) 18:57 — "It's almost every day where you're like — what am I doing?" 27:00 — How to build a team when you can't pay anyone 33:00 — The whiteboard that changed everything 41:00 — Testing Finland in the dead of winter before committing 46:00 — The regret question that made the house decision easy 50:00 — Building a home in a language you're still learning 1:09:56 — Faith's three F's: family, Finland, founder life "We have to be comfortable with the pace that's right for us. And I can't compare myself to others." 🎙️ Find the Nugget: https://www.thenugget.app/ Get in touch with Faith: https://www.linkedin.com/in/falyons/ Substack — deeper dives between episodes: substack.com/@wipitandrepit Instagram: @hh_squared

5. 

   28 Aug 2026

   11. Wanting change and being ready for it are not the same thing (annoyingly)

   Are you lying to yourself about being ready? You say you want a different life. You might even be working hard toward it. So why isn't it happening? This episode gives you a seven-question diagnostic framework to find out exactly which type of stuck you're in — and what to actually do about it. In this episode, you'll learn: Why hard work can keep you exactly where you are (and how to tell if that's what's happening) The question to ask before spending another year on a goal that might not actually be yours Why not knowing your direction yet is a completely different problem — and needs a completely different response How to identify the gap between who you are now and who you need to become Why a desire that disappears when you look at what it costs is not failure — it's the most useful information you have The reason your social circle might be the thing quietly keeping you in place What we discuss: 00:00 — The self-slap moment that started this episode 02:00 — What growth actually feels like from the inside (it's not what you think) 05:30 — What not-ready looks like in real life — and how to spot it in yourself 09:00 — The seven-question framework: find out exactly which type of stuck you're in 19:00 — Why change is possible for everyone — and what it actually requires "Yeah, maybe I wasn't quite ready yet. But I'm getting there." 📚 Episode 2 — The Values Exercise (do this first): https://open.spotify.com/episode/6alL0tupBTRWyi6JYsTNKn (https://open.spotify.com/episode/6alL0tupBTRWyi6JYsTNKn) 📚 Episode 9 — You're not lazy. You're blocked: https://open.spotify.com/episode/0zZ5Bhm9KQgAIKKMLIEJgd?si=j3BL0QODQnWSq7HGGY6zIA (https://open.spotify.com/episode/3Bmh3zMtRuXCQl1vXXDAec?si=a2fe18ebbc144a32) 📚 Episode 8 — I thought I didn't like people: https://open.spotify.com/episode/3Bmh3zMtRuXCQl1vXXDAec?si=a2fe18ebbc144a32 (https://open.spotify.com/episode/3Bmh3zMtRuXCQl1vXXDAec?si=a2fe18ebbc144a32) Substack: substack.com/@wipitandrepit Instagram: @hh_squared

6. 

   30 Jul 2026

   10. Three Months In - What's Actually Happened?

   Recording this from the kitchen table of our unsold flat at 11pm. That pretty much sums up where we are. This is our first check-in — what's working, what isn't, and why the messy middle is not a sign you're failing. In this episode, you'll learn: Why adding a hard deadline into semi-chaos can actually be the thing that grounds you What's genuinely shifted in three months (beach trips, camper vans, and an unexpected love of spreadsheets) Why the posting and marketing still feels uncomfortable — and why that's not a reason to stop How to remind yourself you are the type of person who works things out Why calling yourself a late bloomer might be quietly working against you What's coming next — and why the dream doesn't have to wait until you're ready What we discuss: 00:00 — Recording from the kitchen table of the unsold flat 01:00 — Three months in: the honest headlines 02:01 — What I thought would be done by now (and isn't) 04:28 — The podcast as a structural anchor 07:35 — The nomadic life actually starting 08:35 — What building things has taught me about reading people 10:30 — The spreadsheet revelation 10:57 — The thing I still find hardest: posting and showing up online 14:20 — Helsinki, Barcelona, and the dream starting now 15:21 — Two quick confidence boosts if you need them today 18:44 — Getting together in person — would you come? 19:43 — Where are you at ten episodes in? Tell me. "The comfort zone does not expand before you leave it. It expands because you did." Substack — deeper dives between episodes: substack.com/@wipitandrepit Instagram: @hh_squared

7. 

   16 Jul 2026

   09. You're not lazy, just blocked - Why knowing your values is only the first step

   One Sunday afternoon, a romcom I accidentally put on cracked open something I'd been sitting on for years. This episode is about what it showed me — and the four things standing between your values and your actual life. In this episode, you'll learn: Why knowing your values is just the beginning, not the destination The belief running underneath your actions that's quietly blocking you (and how to find it) Why your values are not all equal — and what happens when you treat them like they are How to chart a realistic route toward the life you want without blowing up the one you have Why self-sabotage is almost never self-destruction — it's self-protection The one question to sit with this week that your mind will start working on by itself What we discuss: 00:01 — The romcom that clicked something into place 05:30 — After the values exercise — what actually comes next 09:00 — The belief thing: Tony Robbins, Freud, and why you keep getting in your own way 21:00 — The hierarchy thing: your values are not all equal 28:00 — The planning thing: you don't have to jump out of the airplane 33:00 — The action thing: you already have more than you think 38:00 — Why money isn't shallow — and what it was actually pointing to 44:00 — The question to sit with this week "That gap between your values and your life is almost always smaller than it looks from where you're standing." 📚 Go back to Episode 2 first (https://open.spotify.com/episode/6alL0tupBTRWyi6JYsTNKn?si=8836450648f143f4)— this episode builds directly on it & The Values Exercise PDF (https://drive.google.com/drive/folders/1yyOn4UiSQwqaXOJ4lgk4hmNzitj-iDAr?usp=sharing)📚 Awaken the Giant Within — Tony Robbins (https://open.spotify.com/show/3PHLGDZB9NJMcLAil8PSG2?si=9b9a7f757beb49d8)📖 The Chimp Paradox — Professor Steve Peters (mentioned in Episode 8) (https://open.spotify.com/show/6i4AsSPljy06b5WIwMqE12?si=3590f56e30154635) Substack — deeper dives between episodes: substack.com/@wipitandrepit (https://substack.com/@wipitandrepit) Instagram: @hh_squared ( https://www.instagram.com/hh_squared)

8. 

   2 Jul 2026

   08. I thought I didn't like people...turns out I was afraid of them instead!

   A panic attack in a car park before a cycling training ride cracked open something I'd been carrying for years. I thought I just wasn't a people person. Turns out I was afraid of them — and those two things look identical from the outside but have completely different solutions. In this episode, you'll learn: Why seeing the real fear (not the surface one) removes half the problem immediately The Chimp Paradox model and how your pre-loaded outlook shapes a room before you've spoken to a single person How a self-fulfilling prophecy keeps you stuck in a story that was never actually true The one question to ask before you react to any uncomfortable interaction Why "I don't fit with people" might be an environment problem, not a you problem How to find the rooms where you walk in and feel your energy go up instead of down What we discuss: 00:00 — The car park02:42 — Fear vs dislike: why the distinction changes everything09:27 — The Chimp Paradox — Professor Steve Peters14:11 — The self-fulfilling prophecy16:37 — The tool applied in real life21:05 — The environment question25:35 — Three things to sit with before you go "It wasn't just me, and it wasn't just my fear. It was also the rooms I was putting myself in." 📚 The Chimp Paradox — Professor Steve Peters: https://www.amazon.co.uk/Chimp-Paradox-Management-Programme-Confidence/dp/009193558X (https://www.amazon.co.uk/Chimp-Paradox-Management-Programme-Confidence/dp/009193558X) I'm Holly. Let's keep WIP'n and Reppin' together. Newsletter: wip-n-reppin.kit.com (wip-n-reppin.kit.com)Instagram: @hh_squared (https://www.instagram.com/hh_squared/)

9. 

   22 Jun 2026

   07. Why I built this & the beer mat story

   WIP'n & Reppin' — Episode 7: Why I Built This (And the Beer Mat That Started It All) Sometimes you have to be a little bit strange in public to get free of what's actually keeping you stuck. This is the origin story. In this episode, Holly tells the story of the away days in Brighton that broke everything open — and the moment she tore up every limitation she'd ever been carrying and threw them over her shoulder in the middle of a bar. Three weeks later, this podcast existed. If you've ever felt like the success stories everywhere are technically inspiring but somehow leave you feeling further behind instead of closer to anything — this episode is for you. What We Cover in This Episode [00:00] Why this episode is a few days late — [01:27] The away days: three days in Brighton to work on business strategy that turned into something else entirely [03:55] The beer mat exercise — what it is, why it works, and how to do it yourself right now with whatever square thing is near you [06:23] Three weeks later: how Episode 1 of this podcast came to exist [07:17] The fear list Holly carried into publishing — and still hasn't fully shaken [09:15] The bigger, scarier vision: what this podcast is actually trying to grow into [12:33] Why "middlescence" needed its own space — and why the standard success podcast format wasn't it [16:24] The problem with nine-figure exit guys interviewing other nine-figure exit guys [20:46] Why grabbing a plan too early might just be a faster route back to the same place in five years [23:34] Starting before you feel ready — and why the fear doesn't resolve first [24:33] The one question worth asking yourself this week The Beer Mat Exercise You can do this at home. Pick up anything square. Imagine everything you've ever been told is possible. Every ceiling. Every limitation. Every way you think things work. Every thing you believe you can and can't do. Put it all in the square thing. See it all in there. Now tear it up into tiny pieces and throw it away. Try This This Week Think of something you've lost track of time doing. Something that didn't feel like work even though it clearly was. What's the smallest real version of that you could start this week — while you're still scared? Don't wait until it feels easy. It probably won't feel easy until after you've done it. If This Episode Resonated Send it to the woman in your life who's stopped letting herself dream. The one so busy keeping everyone else okay that she's forgotten to ask what she actually wants. This might help her today. Links & Resources 🎙️ Join the WIP'n & Reppin' community — free resources, updates & the Values Exercise: wip-n-reppin.kit.com 📲 Follow Holly on Instagram:@hh_squared About WIP'n & Reppin' WIP as in work in progress — because that's exactly what we all are. Hosted by Holly, WIP'n & Reppin' is for women who've done everything right and still feel like something's missing. We talk career pivots, knowing yourself well enough to build a life that fits, what moving your body does for your mind, and saying what you actually think without apologising for it. No fluff. No lectures. Just honest conversations, real tools, and the occasional truth you didn't know you needed to hear. Keywords: women's podcast, career pivot, personal development for women, midlife reinvention, finding your purpose, women's ambition, starting over at 35, starting over at 40, building confidence, middlescence, work in progress, Holly WIP'n Reppin'

10. 

    4 Jun 2026

    05. Health as a Form of Self Respect

    What if not looking after yourself was the highest form of disrespect to yourself? Your body isn't the reward you get once everything else is sorted. It's the infrastructure everything else is built on. Most of us put ourselves last on a list that never ends. Once the project's done, once things calm down, then I'll sleep properly, eat properly, move properly. Except everything else is never under control. That mythical quiet season never comes. Episode 5 is about flipping that entirely — and why treating your body like the foundation it actually is isn't selfish. It's the most practical decision you can make.

11. 

    4 Jun 2026

    06. Impatience as a Superpower!

    Is patience always a virtue!? Fed up of slow and steady wins the race? Good! Maybe that advice has quietly held you back for years. What if we could just throw that shizz out the window!? What if impatience, that restless energy, that fire — is actually drive, vision, and an instinct for spotting a faster, better route that other people simply cannot see yet? In this episode, you'll learn: - How one mentor flipped impatience from a flaw into a superpower (and why that moment changed everything)- Three things impatience actually does when you point it in the right direction - The one skill that stops impatience turning into self-criticism and a weapon against yourself - Four tools to use when you're spiralling about not being far enough along - Why the world needs more impatient people — especially now in the age of AI What we discuss: 00:00 Everyone tells you patience is a virtue 02:45 The mentor moment that reframed everything 05:15 Thing one: finding faster routes (the teaching story) 08:45 Thing two: setting bigger goals (the London move) 11:00 Thing three: reframing what's possible (the business turnaround) 15:30 Four tools for when impatience turns to self-criticism 21:00 Aim for the stars, land on a cloud 23:00 Point your impatience in the right direction Don't apologize for the fire. Just learn to aim it! --- I'm Holly. Let's keep WIP'n' and Reppin'! Newsletter: wipit.beehiiv.com/subscribe Instagram: @hh_squared

12. 

    21 May 2026

    04. You're good at your job - but is it good for you? The career pivots one

    You've followed the plan. Built the career. Ticked the boxes. And now you're exhausted and you genuinely can't tell if it's the job, the rain, or whether you just need three tequila shots! Before you do anything drastic — let's work out what's actually going on first. Because the career might not be the problem. And knowing the difference saves a lot of expensive mistakes. Episode 4 covers the real reasons career unhappiness shows up — from exhaustion to bad managers to the conditions of the job making your dream life impossible. Holly shares her own messy honest version including a cotton sportswear line, a taco towel revelation, and the subconscious rules that kept stopping her before she even knew what they were. Plus the three types of career alignment, Charles Handy's portfolio career concept, Holly's mum's Tuesday reality check — and three questions worth sitting with this week. SHOW NOTES: You've followed the plan. Built the career. Ticked the boxes. And now you can't tell if it's the job, the rain, or whether you just need three tequila shots and a holiday. 00:01 — No work chat policies at the dinner table, stress-spending on kitchen appliances you'll definitely use this time, and the three tequila shots option. A warm hello to everyone who's here feeling slightly surprised by their own life’s twists & turns — and a special shout out to anyone who never expected to be here considering career pivots. We feel you! 04:31 — The four camps: blow it up, company hop, analysis paralysis, avoid it altogether. None of them are wrong — they're just what happens without the right tools. The mission of this show: you don't have to blow everything up to start building something better. 06:56 — The first tool before anything else: self reflection. Not catastrophising or a therapy spiral — just honest quiet time to work out what patterns you're running and what stories exhaustion has been writing for you. 08:00 — Working out where the meh is actually coming from: exhaustion, one bad situation, money, lack of agency, the environment, or the trickiest one — when the conditions of the job make the life you want damn near impossible. 11:26 — Examples of when conditions clash with values 14:00 — The one question that separates a fixable problem from a career problem 15:45 — Panic mode: why it's the worst place to make big decisions from and the nuances it causes you to miss entirely. 17:45 — Holly's honest version: architecture wasn't always wrong — the conditions changed. The portfolio career concept coined by Irish philosopher Charles Handy in 1989. 21:00 — The side hustle period: the cotton sportswear line, the one metre diameter taco towels (fifty thousand pounds a month, thousands of buyers, nobody needs this), and why neither felt right. 24:30 — Subconscious rules: the rules we have about how we're willing to make money that we never consciously named. 32:21 — The money and mission separation: your passion and how you make money don't have to come from the same place. 36:00 — The three types of alignment: task alignment, mission alignment, and role alignment — the industry is right but the role is wrong. 41:30 — Holly's mum's Tuesday reality check: What are you actually doing day to day? 46:00 — Three questions to leave you with: is it the career or something else? Which type of alignment are you looking for? And what does your perfect Tuesday actually look like? Sources: Charles Handy — The Age of Unreason (1989). Irish philosopher. Coined the portfolio career concept. Passed away 2024. Cillian Murphy — referenced as an example of mission and life values in alignment. Connect: Newsletter: wipit.beehiiv.com/subscribe Instagram: @hh_squared I'm Holly. Let's keep WIP'n & Reppin'.

13. 

    14 May 2026

    Intro to WIP'n & Reppin'

    No one is coming to save you. And honestly? That's the best news you'll hear today. WIP'n & Reppin' is honest conversation, real tools and the occasional truth you didn't know you needed to hear. We talk about career pivots nobody prepares you for, knowing yourself well enough to build a life that actually fits, your body and what moving it does for your mind, and saying what you actually think — without apologising for any of it. If you feel like you want more from life or more of YOU in your life then this might be the place for you! WIP — Work In Progress. Reppin' — showing up for it anyway & getting those repetitions in. New episodes every two weeks. First three drop Thursday. I'll see you there. SHOW NOTES: No knight in shining armour. No one coming to save you. Just you, the tools, and the reminder that you never needed saving in the first place - you are a badass remember! 00:00 — The bad news: no one is coming to save you. The good news: you're a total badass who doesn't need a knight in shining armour anyway. 00:20 — What this show exists to do: remind you of that, give you the tools to prove it to yourself and make sure you never forget it again. 00:35 — WIP as in Work In Progress — because that's exactly what we all are. Reppin' — showing up for it. Putting the reps in. Choosing to grow rather than drift. 00:50 — Nobody is late here. There's no perfect timeline. But there is a difference between a life that happens to you and a life you actually direct. 01:00 — What WIP'n & Reppin' covers: career pivots nobody prepares you for, knowing yourself well enough to build a life that fits, your body and what moving it does for your mind, saying what you actually think and asking for what you actually want — without apologising for both. 01:20 — New episodes every two weeks. First three drop Thursday. Connect:Newsletter: wipit.beehiiv.com/subscribeInstagram: @hh_squared I'm Holly. Let's keep WIP'n & Reppin'.

14. 

    14 May 2026

    03. Stop Waiting for Permission!

    Who and what are you actually waiting for? To change jobs, move countries, start that business, take that class, build that new life — what exactly is holding you back? Do you even know? Spoiler: it's probably not what you think. Most of us are waiting for permission — from a boss, a partner, a friend, a random stranger on the internet — to tell us we're finally ready. And women? We feel this one particularly hard. Not because of imposter syndrome — but because of something much deeper that most people never talk about. Here's the uncomfortable truth: that permission was never coming. Not because you don't deserve it. Because it was never anyone else's to give. Seven minutes. One idea. And a question at the end that might actually change something for you today. You probably already know someone who needs to hear this. SHOW NOTES: Who and what are you actually waiting for? To change jobs, move countries, start that business — what exactly is holding you back? Do you even know? 00:00 — We wait for permission constantly without ever realising we're doing it. Permission to change jobs, leave a relationship, launch a business, become successful. Waiting for a boss, a partner, a friend, a random person online to tell us we're finally allowed. 01:30 — Welcome + show intro. WIP — Work In Progress. Reppin' — showing up for it anyway. Nobody is late here. 02:00 — What waiting for permission actually looks like. Researching for six months when you could have started in week one. Asking five people for opinions on a decision you've already made. Waiting until the kids are older, the mortgage is smaller, you feel more ready. Starting sentences with "I know this is probably a silly idea but..." 02:45 — Shrinking a perfectly good idea into something smaller and safer so nobody can reject it. Knowing exactly what you want — and not doing it anyway. 03:00 — Why this hits women harder. It's not imposter syndrome. It's social conditioning. Girls are raised to be perfect. Boys are raised to be brave. Reshma Saujani — founder of Girls Who Code and author of Brave Not Perfect — has spent years researching exactly this. 04:00 — The permission you've been waiting for was never coming. Not because you don't deserve it. Because it was never anyone else's to give. Nobody was waiting to give it to you — they were all focused on their own lives. 04:30 — Inaction might be subconscious self-protection rather than an actual failure to launch. Worth sitting with if you have lots of ideas but keep not acting on them. 05:00 — "But Holly, I'm not ready. I need one more course, one more year, one more thing before I'm qualified to—" That voice is not protecting you. It's keeping you in place. 05:30 — Carol Dweck's growth mindset research: the people who achieve things are not the ones who felt ready. They're the ones who acted before they felt ready and developed readiness through the doing. 06:00 — Name the thing you've been waiting to start. Right now. In your head. Got it? Now — what's the smallest possible real step you could take today? Not the whole thing. The tiniest but real step. 06:30 — Next episode: the one question that tells you whether you're in the right career — not whether you're good at it, but whether it's good for you. The question from this episode: What is the smallest real step I could take today toward the thing I've been waiting to start? Sources: Reshma Saujani — Brave Not Perfect (2019). Founder of Girls Who Code. Carol Dweck — Mindset: The New Psychology of Success (2006). Stanford University. Connect: Newsletter: wipit.beehiiv.com/subscribe  Instagram: @hh_squared I'm Holly. Let's keep WIP'n & Reppin'.

15. 

    14 May 2026

    02. Netflix or Your Life?

    You know exactly how long you spend on Netflix. When did you last spend that same time on your actual life? Most of us think we know what we value. Turns out most of us are wrong — and that gap between what we say we value and what we actually value is the source of almost everything that feels slightly off. In this episode Holly walks you through the exact exercise that changed everything for her. Twenty minutes. One question. And something she wasn't expecting at the end of it — relief. Download the free values exercise in the show notes and do it alongside the episode. SHOW NOTES: How long do you spend choosing something on Netflix? Now — when did you last spend that same time figuring out what you actually value? Yeah. That's what we thought. 00:00 — The Netflix question. How much time do you spend choosing what to watch vs thinking about what you actually value in your life? No judgment. Just a very good question. 01:30 — Welcome + show intro. WIP — Work In Progress. Reppin' — showing up for it anyway. Nobody is late here. 03:30 — The one thing nobody ever teaches you despite it being one of the single biggest predictors of life fulfillment. Your values. What you actually care about at the core of it all. 04:30 — What Holly said she valued vs what she actually valued — two completely different things. And that gap was the source of almost everything that wasn't working. 05:00 — Brené Brown: "You can't live into what you can't name or describe." Most of us are professing values we've never once tested against a real decision. 06:00 — What today is and what it isn't. One exercise. Twenty minutes. A compass — not a five year strategy. 06:30 — The house metaphor. Exterior — what you show the world. Interior — what you think you want. Foundations — your actual values. Most of us spend our lives renovating the exterior and never check the foundations. 10:00 — Holly's architecture story — gym goals, adventures, courses — adding rooms to a house built on partially the wrong foundations. And why freedom was the value she was trying to satisfy all along without knowing it. 14:00 — Holly's mum did this exercise in her 60s and came back genuinely surprised. If she hadn't been asked in six decades of living — why would any of us have been? 15:00 — The values head-to-head exercise walked through live. Step 1: circle everything that resonates from the list. Step 2: cut to your top 10. Step 3: head-to-head every value against every other value. The ones with the most marks are your actual values. 18:30 — Values change — and that's allowed. What mattered at 25 is different from what matters now. This exercise tells you where you actually are right now. 19:30 — The forced choice methodology — why listing values makes us perform our ideal self, but being forced to choose reveals the truth. 20:30 — What Holly felt when she finished the exercise. Not pride. Not excitement. Relief. Everything made sense. The unhappiness wasn't a personal failure. It was a values mismatch. 21:00 — Next episode: the permission you've been waiting for that was never coming. Eight minutes. Send it to a friend. Download the free values exercise: Here Join the community: wipit.beehiiv.com/subscribe The question from this episode: Am I living according to what I actually value — or according to what I thought I was supposed to want? Sources: Brené Brown — Dare to Lead (2018). Research professor, University of Houston. Shalom Schwartz — Theory of Basic Human Values (1992). Cross-cultural values research across 82 countries. Forced choice methodology — values research since the 1970s. Connect: Newsletter + values exercise: wipit.beehiiv.com/subscribe Instagram: @hh_squared I'm Holly. Let's keep WIP'n & Reppin'.

16. 

    14 May 2026

    01. WTF is Middlescence & How Did I Get Here!?

    You probably had a great plan all mapped out, followed it really well, achieved it all — and then one day looked up and thought: hang on, is this it? This isn't quite what I expected! If that sounds familiar you might be going through middlesescence — which you probably aren't familiar with! And no, it's not a crisis (although sometimes it might feel rough!) but rather a time of change and transformation — we gotta look for the silver linings, eh? It is a period of shifting values that causes you to reassess everything, though. Your career. Your relationships. Who you actually are and what you actually want. Think of it as the pupa stage. Uncomfortable, necessary, and no guarantee of what comes out the other side. But nobody who makes it through wishes they hadn't. In this episode Holly unpacks what middlescence could feel like, and why it's far more common than anyone admits, with one reframe that could change how you experience it entirely. New to the show? Episode 2 drops simultaneously — that's where the practical tools begin. SHOW NOTES: Ever feel like you followed the plan perfectly and still ended up somewhere slightly wrong? Yeah. Apparently its a life stage. So no, you're not broken! 00:00 — The quote that started everything: "If you don't build your own life, you spend your life building other people's dreams" — and why Holly still ended up doing exactly that anyway 02:30 — Welcome + what WIP'n & Reppin' is actually about. WIP — Work In Progress. Reppin' — showing up for it anyway. 04:00 — WTF is middlescence? The life stage nobody warned you about — and why it took until 1904 to even name adolescence, so no wonder we're still catching up 05:30 — Elliott Jaques coined the midlife crisis in 1965 and excluded women from his research entirely. His reasoning? Menopause covered it. Thanks Elliott. 06:30 — Gail Sheehy's Passages (1976) — the woman who put us back in the picture and reframed this as a period of questioning, reassessing and becoming. Not a crisis. A transition. 08:00 — What middlescence actually looks like — a career that stopped making sense, relationships that no longer fit, or that quiet persistent feeling that there's more without being able to name what more means yet 09:30 — Men get loud midlife crises. Sports cars, motorbikes they've never ridden, inexplicable craft beer phases. Women carry on, hold everything together and quietly wonder what on earth is happening to them. 10:30 — The reframe that changes everything: the discomfort you're feeling is not a sign something is wrong with you. It's a sign you're outgrowing yourself. One means broken. The other means becoming. 12:00 — Why growth doesn't happen in a nice smooth diagonal line — and the catch-22 of wanting to escape the safe and known whilst being terrified of leaving it 13:00 — How naming it changes everything. Middlesescence is not permanent. It has a beginning, a middle and — yes — an end. 14:00 — Holly's story: architecture, the road trip to the States in a camper van, the anger, the entrepreneur programme and the moment she noticed the discomfort while she was in it 18:00 — The lost period. No map. The caterpillar trying to squeeze through a pupa that's slightly too small. 19:30 — The question worth sitting with this week 20:00 — The close: you are not late, you are not broken, you are in the pupa. And something important is being built in there. The question from this episode: Am I living according to what I actually value — or according to what I thought I was supposed to want? The full tool that helps you answer it is in Episode 2 — dropping today. Sources: Elliott Jaques — coined 'midlife crisis' in 1965. Canadian psychoanalyst. Gail Sheehy — Passages (1976). New York Times bestseller. Connect: Newsletter: wipit.beehiiv.com/subscribe Instagram: @hh_squared I'm Holly. Let's keep WIP'n & Reppin'.