WIP'n & Reppin'

with Holly
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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.

  1. 2h ago

    16. Career Crossroads? How to Choose a Path When Life Isn’t a Disney Movie

    Are you at a fork in your career/life path, just like a Disney princess in the woods?If so, this episode breaks down how to take the next steps when you don't know which way to turnIn the cartoons, the princess gets one dark path and one sunny one, and the choice makes itself. In real life, both paths usually look like the dark one, or the sunny one is simply the route everyone else told you to take. In this solo episode, Holly shares what her failed startup taught her about certainty, the architect's trick for finding a direction before the design exists, and three questions to run any career change, business idea or pivot against.In this episode you'll learn:• Why clarity comes from moving, not from thinking harder• What to do if you don't have a direction yet• Three questions to test any path before you commit to it• How to take the first step without quitting your job or risking the mortgage• Why not knowing how it all turns out is the good newsCHAPTERS00:00 Two paths in the woods: when a pivot feels like a Disney cartoon02:19 Welcome to WIP'n & Reppin'02:35 Clarity comes from moving (the perfectionist's ladder)03:24 What my failed startup taught me about certainty05:49 How to choose: think like an architect's brief07:12 No direction yet? Test a few options at once08:09 Question 1: Does it point at the top of your brief?09:38 Question 2: Can you take the next step without knocking the house down?11:52 Question 3: What do you walk away with, even if it never gets there?13:35 Stuck between several paths? Start with the smallest step15:28 Nobody knows how it turns out (and why that's good)17:43 Your experiment for the next fortnightLISTEN NEXTEp 2: Netflix or Your Life? (the values exercise)Ep 9: You're not lazy, just blocked (putting your values in order)Ep 14: How to Plan a Career Pivot (Without Blowing Up Your Life)STAY IN TOUCHSubstack: Deeper Dives, Reads & Worksheets Instagram: @wipn_reppinWant to be a guest? Apply hereEmail: wipitandrepit@gmail.comJoin a Secret Pivot Soiree here with other women like you WIP: Work In Progress. Reppin': showing up for it anyway.

  2. Oct 25

    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 itThe four fears hiding underneath: not knowing, the pull of old habits, fear it won’t work, and what people will thinkWhy 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 evidenceThree light experiments to help you practise the new you, without the pressureChapters00:00 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 Connect with meInstagram: @wipn_reppinEmail: wipitandrepit@gmail.comSubstack: wipitandrepit.substack.comWant to be a guest? Apply hereListen and follow on Spotify: 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.

  3. Oct 8

    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 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- Instagram: @hh_squared- Instagram: @wipn_reppin- LinkedIn: Holly H

  4. Sep 24

    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 doesWhat lobsters can teach you about outgrowing an old identityGrowing pain vs wrong-fit pain: how to tell the differenceWhy personal development can become the most sophisticated way of never startingThe Stretch Check: three questions for when you're in the middle of itChapters:00:00 The Bear Hunt confession01:30 Welcome to WIP'n & Reppin'02:15 Why this show keeps making you do the inner work05:30 The lobster and the old shell08:30 What going through it looks like on a bad day12:00 The Stretch Check13:45 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 AgilityBrené Brown, Dare to LeadHerminia Ibarra, Working IdentityTony Robbins, Awaken the Giant WithinNoam Wasserman, "The Founder's Dilemma," Harvard Business Review (2008)Michael Rosen & Helen Oxenbury, We're Going on a Bear HuntLobster facts: NOAA FisheriesIf this episode landed, listen next: Ep 9, "You know your values — so why aren't you acting on them?" Free values exercise: linkRead more on Substack: https://wipitandrepit.substack.com/Instagram: @wipn_reppinLinkedIn: 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.

  5. Sep 10

    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 possibleThe moment she realised "not being on the property ladder" was actually the thing that bought her freedomWhy building something meaningful rarely looks like a hockey stick — and what keeps you going on the days it feels like nothing is workingHow to build a team around you when you have no money, no co-founder, and no idea what you're doing yetWhat it actually feels like to arrive in a new country and realise you don't fully know who you are there yetThe one question that cuts through every big life decision faster than any frameworkWhat we discuss: 00:00 — "Life just wasn't working"02:30 — From disaster zones to diapers: Faith's journey before Nugget08:00 — Building a startup in the middle of COVID, two kids, and an identity shift16:00 — 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 anyone33:00 — The whiteboard that changed everything41:00 — Testing Finland in the dead of winter before committing46:00 — The regret question that made the house decision easy50:00 — Building a home in a language you're still learning1:09:56 — 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/@wipitandrepitInstagram: @hh_squared

  6. Aug 28

    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 yoursWhy not knowing your direction yet is a completely different problem — and needs a completely different responseHow to identify the gap between who you are now and who you need to becomeWhy a desire that disappears when you look at what it costs is not failure — it's the most useful information you haveThe reason your social circle might be the thing quietly keeping you in placeWhat we discuss: 00:00 — The self-slap moment that started this episode02:00 — 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 yourself09:00 — The seven-question framework: find out exactly which type of stuck you're in19:00 — 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📚 Episode 9 — You're not lazy. You're blocked: https://open.spotify.com/episode/0zZ5Bhm9KQgAIKKMLIEJgd?si=j3BL0QODQnWSq7HGGY6zIA 📚 Episode 8 — I thought I didn't like people: https://open.spotify.com/episode/3Bmh3zMtRuXCQl1vXXDAec?si=a2fe18ebbc144a32 Substack: substack.com/@wipitandrepitInstagram: @hh_squared

  7. Jul 30

    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

  8. Jul 16

    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 destinationThe 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 areHow to chart a realistic route toward the life you want without blowing up the one you haveWhy self-sabotage is almost never self-destruction — it's self-protectionThe one question to sit with this week that your mind will start working on by itselfWhat we discuss: 00:01 — The romcom that clicked something into place05:30 — After the values exercise — what actually comes next09:00 — The belief thing: Tony Robbins, Freud, and why you keep getting in your own way21:00 — The hierarchy thing: your values are not all equal28:00 — The planning thing: you don't have to jump out of the airplane33:00 — The action thing: you already have more than you think38:00 — Why money isn't shallow — and what it was actually pointing to44:00 — 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 — this episode builds directly on it & The Values Exercise PDF📚 Awaken the Giant Within — Tony Robbins📖 The Chimp Paradox — Professor Steve Peters (mentioned in Episode 8) Substack — deeper dives between episodes: substack.com/@wipitandrepitInstagram: @hh_squared

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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.

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  • Creator
    with Holly
  • Years Active
    2026
  • Episodes
    17
  • Rating
    Clean
  • Copyright
    © with Holly
  • Show Website
    WIP'n & Reppin'