WIP'n & Reppin'

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

Connect with meInstagram: @wipn_reppinEmail: [email protected]Substack: wipitandrepit.substack.comWant to be a guest? Apply here
Listen 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.

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

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
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.

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

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
📚 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/@wipitandrepit
Instagram: @hh_squared

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

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 — 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/@wipitandrepit
Instagram: @hh_squared

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

I'm Holly. Let's keep WIP'n and Reppin' together.

Newsletter: wip-n-reppin.kit.comInstagram: @hh_squared

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.