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'

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.

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

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'.

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'.

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'.

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'.

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'.