Four times a year I stop, pick up my head and get honest about how life’s really going, and I’m now do it out loud so you can too. One hour to get your head out of autopilot, name what you want out of this one wild life, and pick one small thing to move toward it.

Quick question, and answer it fast, before the polished version kicks in. When someone asks how you are, how often is the answer some version of “so busy”? And when you say it, is there a tiny part of you that says it like a flex? Or is it just autopilot?

For most of my life, I wore busy like a badge of honor. Head down, collecting gold stars, doing every single thing I thought you were supposed to do to be “successful.” And to me, busy meant I was a hard worker. Busy meant I had my shit together. If I was not slammed, I was not on track to be the successful person i wanted to be.

Busy was the badge I wore to prove I mattered. You might be wearing one too?

We are taught that hard work and discipline and doing it all are what get you there. And maybe they get you somewhere (they did for me). But is it the life you want (or still want) if the cost is the well being of your mind, body, family…

A year ago I flipped it. I left a fifteen-year corporate career with no real plan, well, a solid savings, my intuition, and an understanding of my risk and runway. And named the thing I was building Life at Play, which terrified my mom. She called, worried that if people thought I was just playing around, no one would ever take me seriously and hire me.

That is kind of the point, I told her… I have a lot to unlearn and learn about myself. And I think playing around is the best way to do it.

These days I’ve been experimenting with building the life I want first, and the work that funds it second. (I also quit saying “I’m so busy,” and you would be amazed how hard that is.)

So here is the thing I do every quarter. I stop. I pick my head up. I get honest about where I am and where I am going, and I pick a small experiment to get a little closer to who I am becoming. Not from a mountaintop with the answers. From the middle of it, still figuring it out. Chaos and all!!

This last quarter I skipped it, and I felt it. The whole summer had a low, itchy, off-kilter feel, and it took me until now, kids back in school, to clock that I never picked my head up. I just kept going. And let me be real, I need this every season as much as anyone.

So I’m doing it here, out loud, every season, because you deserve a place to actually stop and look too.

Every season I sit down, do my own Pick Your Head Up, and share it so you can do yours. A lot of it is the best of what we do at the in-person Life at Play Days in Serenbe, plus the check-in’s I send everyone who has worked with me one-on-one.

I fill in every answer, real numbers and mess and all, so you are never the only person in the room being honest. I go first, all the way, so you don’t have to.

Come along.

Before you start, a few ground rules

Pick a date and protect it. Put it on the calendar like a meeting you cannot move. 60 to 90 minutes, phone down, nobody needs you. This does not work squeezed between drop-off and a call.

Make it a treat, not a task. I’m talking the coziest corner you have, or outside under the trees. A candle, a coffee, a glass of wine if it is that kind of afternoon. Take a few breaths and ground yourself first, one minute works just fine. Then begin. It is meant to feel good. That is the whole point!

Rather be walking? Or talk it out? I have run this with an AI transcriber (like Wispr Flow, Granola or Otter) in my ear on a walk, and had it transcribe what I said while I walk around talking out loud to myself like a crazy person :).

This is for your eyes only. My first time truly looking under the hood, I kept it locked in a drawer, it felt so raw. Years in, I am a lot more open. Write it for you first,then decide about sharing after.

Write fast and sloppy. First thing that pops in, no judging. That first instinct you almost skip is usually the one that needs to come out. This is not hours of homework. Move quick, stay honest, see what surfaces.

Okay, here we go.

1. The Life Check-In (5 min)

A gut-check on your whole life in about five minutes. Grab the full free Life Check-In here. You score each slice of life, nutrition, sleep, money, sex (yep, that one too), all of it, from 0 to 100, and mark whether it is climbing, holding, or sliding. I do this one any time I feel off and cannot name why, and with Greg when we need to zoom out on us. Do not try to get everything to 100. Nobody’s board is all green, and chasing that is its own kind of crazy. You are just hunting for where you are quietly out of whack. That is it.

2. Your core values (15 min)

Businesses get core values. So do you, and yours are more useful. If you have never named yours and feel stuck, here is how. I know, “values” can sound like a laminated poster in a boring break room nobody cares about. Personal ones hit different. Mine are basically a cheat code for saying no: is this a yes to how I want to live, or another “should” I picked up somewhere along the way? If it doesnt align with my values, easy pass. (If you are a chronic yes-person, this one is about to change your life, and I am only slightly kidding.) Already have yours? Check in, still true?

Since mine are locked, I did a spin this season and wrote our family rules instead. More on that, and Greg’s genius childhood ones, in my answers section.

3. What does a good, successful life mean to you right now? (10 min)

The big one, and the one that surprises people most. Two ways in, do one or both. Big picture: what does a good, successful life mean to you right now, not the ones from five years ago? Then get granular and walk one perfect ordinary day. What are you eating? Where are you? Who is there? What are you doing at 10am, at 3pm? How do you feel in your body?

ok now notice… your ideal day is secretly telling you your definition of success, just wearing a disguise. Do yours match?

4. Your girl crushes (or guy crushes) (10 min)

The fun one. Write down the people you are low-key obsessed with. Not the ick jealous, why-her kind of noticing, the good kind, the ones who lift you up, inspire you. Or you are infatuated with but never stopped to think… why? Get curious.

Then get specific: is it how they move through the world, what they have built, their whole aesthetic, the way they treat the barista? Then look for the patterns. Mine told on me before I had any idea: every woman I was crushing on had built something of her own. I wanted in those rooms. So I went.

Your crushes might just be a map to what you really want. Read the map.

5. If you were 90, looking back (5 min)

Fast forward. You are 90, tea in hand, comfy shoes on, looking back on this exact season of your life. What do you hope you did with it? And what are you so glad you finally stopped putting off?

6. Your unhinged dream (5 min)

My favorite, and the one you might want to skip. DON’T! Your most ridiculous, unrealistic, slightly unhinged dream, the one that makes you go “lol, no.” Write it anyway.

Yes, especially that one. Nobody is reading this but you.

7. Your one experiment for the season (10 min)

And the whole point. Pick ONE small thing to play around with this season that nudges you toward the person you just described. One. Not a list, not a five-year plan, not a whole new you by Monday. And when I say play, I do not mean frolicking through a meadow with bunnies (though if that is the dream, go be free). I mean a tiny, low-stakes experiment pointed at the life on your mind: a coffee with someone already doing the thing, offering to help a friend with it for free, one class, one small test. The smallest real step that counts.

Here is why it works: every little step shows you something you could never see from the couch, and it builds momentum, so you are not frozen at the bottom of some terrifying leap. You are moving. You get to feel what that life is like on a regular Tuesday before you bet the house on it. Clarity comes from the doing, not the thinking.

So, what is your one experiment this season? Tell me in the comments. And tell me what you’re wrestling with this season. I read every one, and it’s how I know what to help with next.

Leave a comment

A quick note: Normally the second half, where I fill in every answer from my own real life, numbers and mess and all, willjust be for paid members. This first one, I am handing you the whole thing, free, as a taste of what these are.

How I answered these this quarter

1. My Life Check-In

Fast and honest, no rounding up to look good.

• Nutrition, 70% ↑. I’ve been a “healthy eater” for most of my life, but I did indulge this summer, and I will be real, the vape pen or glass of wine has been getting more play than usual, which has sent my late-night snacking up with it.

• Body and movement, 60% ↑. Lower this season err years with kids. I am active with my family but I am lacking a consistent workoutt (even my normal consistent walks have died with the summer heat). The goal now that the kids are back in school is one class a week, and two walks every week. Hit that and I am a solid 80 which feels great.

• Sleep, 100% →, baby. I am extremely skilled at this one and it’s a huge priority for me. I’ve always felt like I should have it listed on my resume. I know big brag 😉

• Stress and nervous system, 70% →. Kids, at the early stages of starting Business and trying to figure out how much money to invest into it vs pay myself are my main stressors today. + Greg has been stressed at work lately and that ripples through all of us, but I fell okay about where it’s at. 4 years ago this was around a 15%, so I’ll take 70% any day.

• Relationships, 90% →. Rock solid. Amazing friends, great family, good people. couples therapy paid off in big ways, and I’ve been very focused on a small number of close relationships lately and just feel very held by them all.

• Purpose and direction, 95%→ on a good day, 30%→ on a bad one. I think that is just building your own thing from scratch. Some days I feel unstoppable, some days I am crumbling and doubting it all. The funny part is I keep circling back to what I set out to do at the very beginning. I just apparently have to take a few wrong turns to find my way back to myself.

• Work and career, 50%→. Big dreams, barely started. I like to act like I am not in a rush to grow, and arrive. That is a lie. I am. My ambition runs hot and I am practicing being okay right where I am, because this scrappy part is probably the best part. but it would also be very nice to have consistent, repeatable income coming in… but we are just not there yet.

• Money, 20%↑ (up I hope). The lowest number on my whole board. I have always been a consistent, steady high earner, and this is the first year I am not. Which, said out loud, makes total sense, but also fucks with my mind the most. You do not build something from zero and fall into money right away. A lucky few do, and if I am being fully honest, I quietly hoped I would be one of them, the strange anomaly who cracks it fast… But I did not even have a paid offer or way to work deeper with me out in the world until five months ago. So a six-figure first year was never realistic.

  Knowing that does not stop it from getting to me. About once a month I have to sit with the discomfort and stare it dead in the face, because money has started to feel like a little ticking time bomb, my quiet worst fear being that the income does not follow and I do not get to keep doing this thing I love. Then I remember why I started, put my head down, take the next step, and trust the money will follow.

  Here is something I didn’t realize until today. A few years ago I had the exact opposite problem: plenty of money, and a daily “can I really do this same soul sucking song and dance again?”, the sunday night scaries were STRONG. I flipped the whole thing on its head. Now I love my days and I am sweating the money. But freedom is one of my core values, and freedom needs both, work I love AND money coming from it. So I keep returning to the grounding truth: I worked hard for a safety net exactly so I could afford building years like this one, right at the start of building something, and trust it will come together when it is supposed to.

• Joy, fun, play, 90% →. I have been protecting this hard, and even buried in kid and a house renovation chaos I amlaser-focusedd on making sure it all stays fun.

• Sex and intimacy, 70% →. Earlier this year when I first did this activity I was shocked to find this was at an all-time low and I had zero awareness around it. We have been putting real attention on it. I will not lie, a few of my fairy smut books have been putting me in the mood and giving me some new ideas (wink).

• Spirituality, 65% →. Strong last year, still present, but I have let the daily practice slide. I have aspirations of getting it back, even just a daily 5 min meditation goes a long way for me.

2. My core values

Freedom, joy, kindness, growth. Locked, and they have been for a while. like 5 years

• Freedom sits at the top, and it is the one that pulled me out of my old career. It is four things for me: money (enough to do and afford what I want), time (deciding how and when I spend my days), community (who i surround myself with) and place (where I get to be while I do it). Here is what I did not see for years: I had the kind of freedom money can buy, but almost none over my time (9-5, 5 days a week) or location (strictreturn-to-officee rules). That gap is what finally got me to leave. What I want now is to work and live when I want, how I want, where I want, andhave enough in the bank to spend it on the people and experiences that make a life. Turns out there is a lot that goes into freedom…

• Joy is the one I refuse to treat as optional. Even in a life full of kid logistics and to-do lists, I am protecting the fun, because a life that is not fun is not a life I want.

• Kindness, if you spend five minutes with me, I want you to walk away lifted, like you could take on the world. period. That is the person I want to be for my kids, for Greg, for my close circle, and for you. (I know I inherited this one from my incredible mother, I’m not sure what her values are but I know kindness is at the top). Also if you are not a kind person… I ain’t got time for that.

• Growth is simple. I always want to be learning. I do not do stagnant. If I am not growing and learning, I get itchy.

Since my values haven’t moved in the last 5 years, I decided to take a different angle with this question and apply them to our family and house rules. One night Greg wrote out the ones he grew up with, from memory, and they were so good we printed them and hung them on the wall where everyone can see. His are the practical, slightly bossy kind: if you open it, close it, if you make a mess clean it up.

Reading his made me want a lighter, sillier, more us version to turn into art and hang on a wall for all to see. So I am painting one (inspired by Jordy Rose). Still narrowing to 5 or 6, but the running list:

Be kind.
All are welcome.
Go outside.
Come as you are.
Laugh daily.
Quit on a good day.
Breathing is your superpower.
Be helpful.
Big feelings (and farts) o.k.

3. What a good, successful life means to me right now

Success right now is making money that funds the best most alive version of my life I can imagine while working hard on something that helps people become the greatest version of themselves. It is being someone who does not get lost in the sauce of life, who lives fully and a little wildly, who is playful, and who is rock-solid dependable to her people. It is being a caring mother who helps my kids become their greatest selves too. It is being the partner to Greg who prioritizes art and play and fun and also runs a thriving business that does not consume me but lifts me up and does not need me feeding it every single day.

I know a run on sentence. That’s it in the raw.

What that actually looks like the freedom to work 25-30 hours most weeks and take two full months off a year. Plus a five-hour chunk each week that is not for work but for growing, self-care, and nourishing myself, no guilt, no shame.

My ideal day: half the week I wake up with an hour to myself to move, meditate, make art, or write, plus a guilt-free ten minutes on my phone because I like it and I refuse to be ashamed of it (I just refuse to lose the whole hour to it). The other days I wake up naturally with the kids and flow into a family breakfast, something healthy and nourishing eggs, greens, and coffee with milk (always). Then I make something for the business or just for me. Around 2 or 3 I get up and I move my body, or I see a friend, or I cook, then one more hour or two of work, then I get the kids, and I am theirs for the evening + a monthly girls’ night and date night with my hubby. Ideally, we do a simple family dinner with friends, homemade, from our garden or local farms and bakers, feeding the people and places around us.

4. My girl crushes, and the pattern

Right now I am crushing on the writer , and always on , Glennon Doyle, Dax Shepard, Amy Poehler, and Malcolm Gladwell. On Instagram I love Clara Infante, Sierra Campbell, Alice Grace, , Emily Henderson, and Tim Chiusano, plus a pile of artists.

Here is what surprised me. This list used to be all people from the yoga and wellness world. Now it is writers/podcasters, artists, and creatives. That shift is telling me something, and I am listening.

5. If I were 90, looking back

I want to look back and see how many lives I impacted in big and small ways, and that I did it without burning myself down. That I stayed off the treadmill, stayed calm, stayed close to my family and my art, and focused on simplifying my life (less is more kinda thing). I hope I can say I lived fully and wildly… and of course that I’ve lived a life at play.

6. My unhinged dream

The first thing that popped out, and I do not know what it says about me: getting to choose which brands pay me to share their work, on my terms, in a way that is real, instead of waiting around to be asked. And the properly unhinged one: my newsletter written up as the publication to help and inspire people to build a wild, great life on their own terms.

But I think the real thing is a community of people that value and will pay for things Icreate – whether thats a newsletter, art, a book. wherever creativity and fun takes me. And enough money to be able to invest in others building out their dreams.

I know i said one… but this was my stream of consciousness and Im not over thinking it. just getting it on paper.

7. My one experiment this season

The main one is prioritizing art for no reason at all than enjoyment. But my whole business is one big experiment I am running right now: hosting gatherings, doing one-on-one intensives, writing consistently, showing up on Instagram and substack consistently.

ok and the scary one is I’d like to carve out space to start making big swing asks.

You can do all of this on your own. That is the whole point, and it is plenty. But if you would rather not do it alone, or you are in a properly stuck season and want to go deeper, there are a couple of ways in with me:

Life at Play Days, in person. Every season I host one in Serenbe, a full day doing this exact work in a room with the right people. Walking, journaling, giggling, real talk, good food, nature, the whole thing. They are small on purpose and they fill. People on this list, get first access every time, a full 48 hours before spots open to the public. The next one is October 2nd, and I am opening it next week.

Private Intensives. For a bigger change, or a season you’d rather not white-knuckle alone, I take a few private clients at a time. Different doors, same idea. Come find me.

Now lift your head up, and go do yours. And keep me posted on how it goes!

In your corner,

xx Gina

P.S. Know someone in the middle of a “wait, is this it?” season? Forward this. The best ones find their way through friends.