Courage & Clarity

Have you ever set big goals in January and found yourself off track by February?

This episode kicks off Steph’s month-long planning series. She shares how Year on the Wall started in 2018 as a homemade fix for a toddler mom and new business owner who was overwhelmed, and how it grew into a planning movement that thousands of entrepreneurs now use.

You’ll hear:

• Why a goal list is not the same thing as a plan
• The real reason most plans are dead by February
• How to plan around your life instead of against it, including the sick seasons, travel schedules and busy months you can see coming
• Steph’s “life buckets” approach to defining success in every area of your life
• What to do when the road closes: how to adapt your plan instead of shredding it
• Why “winging it” costs you more than a plan that needs adjusting

✨ YEAR ON THE WALL WEEK | TICKETS ARE ON SALE NOW

For the first time, Steph’s annual planning event is a live three-day series: December 1, 2 and 3 at 12pm ET, one 90-minute session each day. Bring your calendar pages and sticky notes, and you’ll leave with your 2027 mapped out before the holidays.

Just $47.

👉 Get your ticket at https://yearonthewall.com

✨ Sold Out Group Programs

Join the waitlist: https://stephcrowder.com/mastermind

Connect with Steph
Instagram: @heystephcrowder

What happens when 13 women who’ve only ever met on Zoom finally get in the same room?

In this episode, I’m sharing the details on my first-ever two-day live event for my Sold Out Group Programs mastermind clients.

You’ll hear:

• Why my clients said they got two weeks of coaching in two days
• How I paid for a $10K event out of cash flow, and why I see it as an investment
• The first step I took when I had no idea how to plan an event
• How a live event turned into a deadline for new curriculum, branded photo shoots, video footage, and testimonials
• Why I think in-person gatherings will be worth even more in the age of AI

✨ Year on the Wall 2027 | $47

December 1–4, 2026: now a 3-day virtual event (plus a bonus day).

Link coming soon, mark your calendar now.

✨ Sold Out Group Programs

Join the waitlist: https://stephcrowder.com/mastermind

Connect with Steph
Instagram: @heystephcrowder

What if the most committed thing you could do for your business is not quitting your job?

In this episode, Steph shares a side of her story she rarely talks about: two failed businesses, a part-time customer service job she took after leaving a director-level role, and a full year of contract work that kept the lights on while she built her business to nearly six figures.

If you’re in the early innings of your business, this one’s for you. Steph gets honest about the financial pressure many entrepreneurs put on their businesses way too early, and what it does to your confidence, your sales, and your staying power.

This conversation is a must-listen if you’ve ever thought:

“If I get a side job, it means I’m giving up.”
“This launch has to work. I need it to pay the bills.”
“I made this my full-time job, so it has to work.”

You’ll hear:

• The two strategies Steph says she wouldn’t be here without: apprenticeship and the bridge job
• Why you need to be able to afford a bad launch (and why that’s not negative thinking)
• How financial stress shows up as desperation in your sales, and why calm sells
• How to treat your paycheck as a “silent investor” in your business
• Proof that success takes time
• The question to ask yourself: What if it takes me five years? Am I still in?

Whether you’ve already jumped or you’re still deciding when to leap, this episode will help you take the pressure off and set your business up for the long game.

✨ Year on the Wall 2027 | $47

December 1–4, 2026: now a 3-day virtual event (plus a bonus day).

Link coming soon, mark your calendar now.

✨ Sold Out Group Programs

Join the waitlist: https://stephcrowder.com/mastermind

Connect with Steph
Instagram: @heystephcrowder

What happens when you set a “delusional” goal and then commit to the most boring plan possible?

In January, Steph said out loud that she was going for a million dollars in a single year. In this episode she gives an honest, no-filter update.

Steph shares the real numbers and the real strategy behind them, plus the mindset that keeps her going without spiraling about the million.

You’ll hear:

• Why “boring” is Steph’s word of the year, and how focusing on one hero offer changed everything
• The simple math that made a million feel inevitable instead of impossible
• How going from 2 enrollment periods to 5 created far more offer exposure
• How the First Clients Fast Track turned an “iceberg idea” into an on-ramp that converts 10%+ of participants into her mastermind
• Why aiming for a million put her on track to nearly double last year’s $350K
• The sufficiency goal: the counterintuitive mindset shift that lets you go big without desperation
• Why your business can only grow as much as you do, and why you shouldn’t wait to love your life

✨ Year on the Wall 2027 | $47

December 1–4, 2026: now a 3-day virtual event (plus a bonus day).

Link coming soon, mark your calendar now.

✨ Sold Out Group Programs

Join the waitlist: https://stephcrowder.com/mastermind

Connect with Steph
Instagram: @heystephcrowder

"I just don't think I can afford it."

Does your stomach drop when a prospect says that? Do you back off, thinking it would be rude or pushy to keep the conversation going? Then this episode is for you.

In this episode, Steph takes on the most common objection in any industry, the money objection. She shares the same insights she's been coaching her Sold Out Group Programs clients on, straight from the sales calls they've sent in for review.

Sometimes "I can't afford it" is real, and Steph is the first to say we should respect that. But often it's covering something deeper: fear, self-doubt, bad timing, or a past experience that didn't work. When you learn to look underneath it, everything about how you sell changes.

You'll hear:

• Why "I can't afford it" is often a cover for something else, and how to find out what's underneath
• The "scales of justice" framework for tipping the balance so clients aren't only able to pay, they're happy to
• Why you need a yes to the plan and the transformation before money enters the conversation
• How to make money "just a logistic," using a car dealership as the example
• Why your clients' finances are none of your business, and how staying out of their wallet works both ways
• The creative ways Steph's clients have funded their investments, from Poshmark sales to professional cuddling sessions (yes, really)
• How to have an ROI conversation that makes a $10K investment feel completely different

If you've ever walked away from a sales call thinking you lost the lead to money, this episode will help you see what was really going on and what to do next time.

✨ Year on the Wall 2027 | $47

December 1–4, 2026: now a 3-day virtual event (plus a bonus day).

Link coming soon, mark your calendar now.

✨ Sold Out Group Programs

Join the waitlist: https://stephcrowder.com/mastermind

Connect with Steph
Instagram: @heystephcrowder

In this episode, Steph unpacks the "ick": that visceral, gross, out-of-alignment feeling that creeps in when you're selling, and walks through the single shift that turns it around. She breaks down the three specific moments where the ick shows up most (reaching out to your warm network, crafting your "what do you do?" one-liner, and sitting on a sales call wanting the client so bad), the one thing that's always happening when the ick hits, and how moving the spotlight off yourself and onto the person you're serving can completely change the energy of every sales conversation you have.

What You'll Hear In This Episode

• A Q4 update: wrapping up the First Clients Fast Track with 41 new clients (plus mastermind clients), the upcoming first-ever mastermind client event, and what's changing about Year on the Wall 2027 (now a 3-day virtual event, Dec 1-4)
• The difference between healthy discomfort (the nerves of clicking send on a scary email or pitching yourself for a podcast you'd die to be on) and the ick, which feels grabby, desperate, and out of your integrity
• The concept of "desperation breath" she learned from her Groupon sales training days, and why both sides of a desperate conversation can feel it radiating
• The client who ping-ponged between forcing herself to reach out to friends and avoiding it entirely with busy work, and how she admitted, "I can only do that so many times before I just feel like I have to take a shower"
• Why every time the ick shows up, the same thing has happened: "You've made it about yourself. That's it."
• The friend who kept trying to come up with a clean, tight one-liner for conferences, only to realize, "The one-liner I'd been craving was never for them. It was for me."
• The sales call where Steph wanted a dream client so badly she slipped into grabby energy, was the only prospect she didn't close that round, and how reaching out from a place of total service months later landed the client
• The "medicine in your pocket" analogy: "You're walking around with the medicine in your pocket, and there's people dying in the street, and you're like, 'Well, I don't wanna swoop in and make it about me.' Give them the medicine."
• The dating analogy: sitting at the bar batting your eyelashes hoping they'll come over versus having the courage to make the first move with curiosity and saying, "Hey. I think we should talk."
• The Ick Test as a gut-check for every sales moment: are you giving cool, service-minded, helper energy, or desperation, "this has to work," me-me-me energy?
• Why service-based selling will change your life, and the moment clients light up and say, "Oh my God. Yeah, that's right. That's all that's happening is I'm thinking about myself."

✨ Year on the Wall 2027 | $47

December 1–4, 2026: now a 3-day virtual event (plus a bonus day).

Link coming soon, mark your calendar now.

✨ Sold Out Group Programs

Join the waitlist: https://stephcrowder.com/mastermind

Connect with Steph
Instagram: @heystephcrowder

In this Walk & Talk style episode, Steph breaks down the real numbers and the real mindset shift behind a launch that started with just six sales and ended with 41 paying clients for her 30-Day First Clients Fast Track. She walks through the exact moment she almost canceled the whole offer, the "driver swap" that changed everything, and the specific strategic moves (the webinar, inviting mastermind clients in, the email rallying cry) that carried it the rest of the way.

What You'll Hear In This Episode

• The backstory on the First Clients Fast Track: how it started as an internal 30-day on-ramp for her mastermind clients before becoming a public $197 offer
• The moment six sales came in against a list of over 4,000 people, and her first instinct: "I'm so embarrassed. I wanna cancel this."
• The mindset shift that changed the whole launch, swapping the thought "nobody wants this" for "they don't get it"
• Why she believes "money is money" and people don't buy what they don't understand, no matter the price point
• How inviting mastermind clients into the fast track turned six people into a party of 21 before she even opened the webinar
• The live webinar where 15 people bought on the spot, including someone who logged on with 3 minutes left, said "I still don't get it," got the full pitch again, and bought anyway
• The Post-it note exercise she used to get into gratitude for her first six clients instead of chasing more
• Why she believes launches should be run from the energy of your most excited, most ready client, not from fear of the ones who might be scared
• Her "court case" framework for managing a brain that's only showing you the bad evidence
• The quarterback analogy for knowing when to swap out the driver in your own launch

✨ Year on the Wall 2027 | $47

December 1–4, 2026: now a 3-day virtual event (plus a bonus day).

Link coming soon, mark your calendar now.

✨ Sold Out Group Programs

Join the waitlist: https://stephcrowder.com/mastermind

Connect with Steph
Instagram: @heystephcrowder

Steph unpacks a pattern she's watching play out in real time: the online business world skipping mindset work in favor of pure strategy, and why that's setting people up for the same crash she lived through after her own rapid success in 2020-2021. She makes her case using a driver/car analogy, digs into her complicated feelings about AI from both sides of the fence, and lays out the punchline: for every strategy or AI skill you build, you need a corresponding mindset skill to counterbalance it.

What You'll Hear In This Episode

• Why this moment in 2026 feels like an echo of 2020 -- the same rush-to-strategy pattern, just with AI instead of a pandemic
• The story of Steph's first rapid success with her mastermind (then called The Messy Middle) -- going from $997 courses to $3,900 clients almost overnight, and why she wasn't ready to hold it
• What led her to shut down her business, lose 200 podcast episodes, and step away entirely
• Why unchecked mindset is "literally like your tween daughter is hijacking the car"
• Her honest take on AI from both sides, for people scared of being left behind, and for people who've become so reliant on AI they can't think an original thought
• Why she believes "when something is clearly AI, it does break the connection to the person" including her Pinterest ad and Instagram caption examples
• Her prediction: "the very next wave is going to be connection"
• The punchline: "For every strategy or every AI skill that you build... you need a corresponding mindset skill to counterbalance it"
• Why she believes burnout comes from poor mindset, not from working too hard

Quotable Moments

"Rapid success will make you run away."

"Strategy is driven by mindset. Mindset is the driver of the car."

"You can have the fastest car in the world, but if a hijacker is driving it... it's going off a cliff."

"AI can't prepare you for it. There's no $297 challenge for this."

"It's one thing to get it. It's another thing to hold it."

Reflection Questions From This Episode

• Are you balancing your strategy with mindset, or working almost entirely in one lane?
• If you're afraid of AI, is fear the one actually driving the car?
• If you rely on AI heavily, could you still produce your work without it?
• Are you preparing yourself to hold success, not just to get it?

✨ Year on the Wall 2027 | $47

December 1–4, 2026: now a 3-day virtual event (plus a bonus day).

Link coming soon, mark your calendar now.

✨ Sold Out Group Programs

Join the waitlist: https://stephcrowder.com/mastermind

Connect with Steph
Instagram: @heystephcrowder

This week's episode is a different kind of story. Steph and her family spent Labor Day weekend at a YMCA family camp, something her husband grew up doing every year and always called one of his top childhood memories. Steph never fully understood why until she experienced it herself: no air conditioning in 100-degree heat, a drained pool, cold showers that couldn't touch the heat, and days built entirely around dining hall meals and outdoor activities.

It was not her idea of a dream vacation... and that's exactly the point.

In this episode, Steph shares what she took away from three days of discomfort, disconnection, and unexpected joy, and the framework she's now bringing into her business and her life:

What's covered:

• Why Steph almost went into the weekend "taking one for the team," and the mindset shift that changed everything
• The difference between leaning in and standing on the sidelines with your arms crossed, and why that choice determines whether you actually get anything out of an experience
• Bonding through simplicity: what happens when cooking, cleaning, and decision fatigue disappear for three days
• What three days with no phone service taught her about her own brain
• The idea of "growing capacity," and why the conditions being hard didn't cancel out the good
• Curiosity over judgment, and how pre-deciding you already know the ending (in a launch, a sales call, a project) quietly kills opportunity
• The story behind the episode title: a camp program director, a locked box of marksmanship equipment, and the mantra she uses to stay calm under pressure
• The Improvise, Adapt, Overcome framework, and how Steph is already using it with her own mastermind clients

✨ Year on the Wall 2027 | $47

December 1–4, 2026: now a 3-day virtual event (plus a bonus day).

Link coming soon, mark your calendar now.

✨ Sold Out Group Programs

Join the waitlist: https://stephcrowder.com/mastermind

Connect with Steph
Instagram: @heystephcrowder

Steph just finished 30 straight days of posting on Instagram, and she is the first to tell you it was not her best work. Some posts got four likes. Some went mini viral. And by the end of it, 135 new people had walked through her doors.

In this episode, Steph makes the case for the 30-day challenge: picking one direction, and doing a little bit every single day.

This one is for you if you have ever thought:

"I'll start once I know what I'm doing."
"I don't want to put out anything that isn't my best work."
"I'm too busy to commit to something every day."

Steph shares what she learned from her own imperfect 30 days, why quantity builds the skill that quality depends on, and how 30 days of reps hands you real data instead of the stories you have been making up about what does and doesn't work for you.

✨ Year on the Wall 2027 | $47

December 1–4, 2026: now a 3-day virtual event (plus a bonus day).

Link coming soon, mark your calendar now.

✨ Sold Out Group Programs

Join the waitlist: https://stephcrowder.com/mastermind

Connect with Steph
Instagram: @heystephcrowder

In this episode, Steph breaks down the four offer problems that quietly block client flow, and how to audit yourself against each one. This is the hand to hand combat side of selling, no funnels, no ads, no launch strategy required.

If you want three clients in the next 30 days, this episode is your starting point.

✨ Year on the Wall 2027 | $47

December 1–4, 2026: now a 3-day virtual event (plus a bonus day).

Link coming soon, mark your calendar now.

✨ Sold Out Group Programs

Join the waitlist: https://stephcrowder.com/mastermind

Connect with Steph
Instagram: @heystephcrowder

Steph breaks down the exact framework she built for clients who wanted to make their entire mastermind investment back in 30 days or less, the same system that helped clients sign three and five new clients in a single month. She walks through what she would have you focus on if you came to her tomorrow and said you just want to end September with a paying client.

✨ Year on the Wall 2027 | $47

December 1–4, 2026: now a 3-day virtual event (plus a bonus day).

Link coming soon, mark your calendar now.

✨ Sold Out Group Programs

Join the waitlist: https://stephcrowder.com/mastermind

Connect with Steph
Instagram: @heystephcrowder

Steph is kicking off the school year with a topic she's been coaching her clients on nonstop this year: time.

In this episode, Steph gets real about the time stories she used to tell herself, the ones that kept her stuck believing more time equaled more success. She breaks down the exact mindset shift that changed everything for her, plus the practical system she now uses to track, plan, and reconcile her time like a budget.

This episode is a must-listen if you've ever thought:

"I don't have enough time to grow my business."
"I'm maxed out and there's nothing left to give."
"I planned my whole week and then everything fell apart."

Steph shares how she runs her business on 20 to 25 hours a week, the exact categories she tracks her time in, and the nightly ritual that keeps her from ever feeling behind again.

✨ Year on the Wall 2027 | $47

December 1–4, 2026: now a 3-day virtual event (plus a bonus day).

Link coming soon, mark your calendar now.

✨ Sold Out Group Programs

Join the waitlist: https://stephcrowder.com/mastermind

Connect with Steph
Instagram: @heystephcrowder

Steph unpacks a concept that came to her mid-launch: the balance between data and delusion. Data keeps us honest and pulls emotion out of our decisions. Ot's critical, and Steph is the first to insist you know your numbers. But there's a sneaky trap where a smart, anxious brain starts weaponizing the data mid-launch, cherry-picking the numbers to build a case for why it's all falling apart.

This episode is about learning which mode to be in, and when. Prepare with data. Review with data.

But once you've jumped out of the plane, you might as well believe the parachute will open.

✨ Year on the Wall 2027 | $47

December 1–4, 2026: now a 3-day virtual event (plus a bonus day).

Link coming soon, mark your calendar now.

✨ Sold Out Group Programs

Join the waitlist: https://stephcrowder.com/mastermind

Connect with Steph
Instagram: @heystephcrowder

In this episode, Steph opens from the side of a lake with her kids in the water, then hands the mic to an episode from the archives that she has been sending clients to on repeat. It was originally episode 15, recorded when she came back to business in 2022, and the idea inside it has not aged a day.

You know that thing that happens when you MISS? It could be a workout, an appointment you had with yourself to record a podcast, a launch you promised you'd get off the ground... you name it, there are moments when our best laid plans go awry. How you respond to those moments is where your story is truly written. Tune into this episode to learn about the power of "where you left off" thinking.

✨ Year on the Wall 2027 | $47

December 1–4, 2026: now a 3-day virtual event (plus a bonus day).

Link coming soon, mark your calendar now.

✨ Sold Out Group Programs

Join the waitlist: https://stephcrowder.com/mastermind

Connect with Steph
Instagram: @heystephcrowder

In this final episode of her Second Half Series, Steph pulls back the curtain on the audience growth myth that keeps talented entrepreneurs stuck. Here's the truth: a viral moment with no plan behind it can still add up to exactly $0. She's coached clients with 150,000 followers who weren't making a dime, and watched others turn a single viral post into a booked-out wait list. The difference was never the size of the audience. It was what happened after the attention arrived.

If you're ready to stop chasing eyeballs and start turning attention into enrollments, this one is for you.

✨ Year on the Wall 2027 | $47

December 1–4, 2026: now a 3-day virtual event (plus a bonus day).

Link coming soon, mark your calendar now.

✨ Sold Out Group Programs

Join the waitlist: https://stephcrowder.com/mastermind

Connect with Steph
Instagram: @heystephcrowder

This is Day 4 of Steph's Second Half Series, where she walks through the five things she'd inspect first if you were her client and told her you wanted to double your results before the year ends. Today she's into the one that quietly makes or breaks your fall: your enrollment system.

Here's what happens every autumn. Everyone's ready to buy, thinking about back to school, the holidays, a fresh start. But everyone's also ready to sell. The people who took the summer off come back, look at the calendar, look at the bank account, and think "I need to launch." The feeds get loud. The offers pile up. And the entrepreneurs who just toss a few things out there and hope get swallowed whole.

Steph walks through the exact mistakes she sees draining launches before they ever get off the ground, and how her Buzz Blitz system turns buying season into your best enrollment yet instead of your most exhausting one.

✨ Year on the Wall 2027 | $47

December 1–4, 2026: now a 3-day virtual event (plus a bonus day).

Link coming soon, mark your calendar now.

✨ Sold Out Group Programs

Join the waitlist: https://stephcrowder.com/mastermind

Connect with Steph
Instagram: @heystephcrowder

This is Day 3 of Steph's five-part daily series on finishing this year stronger than you started, and it also happens to be episode 200, a milestone worth marking. Today Steph gets brass tacks on the sales fundamentals she'd inspect first if she were your coach.

She makes the case that closing is a skill, not a personality trait, shares why the best closers are almost never the Wolf of Wall Street type you're picturing, and reveals how her own sales-call skills have driven back-to-back six-figure launches with an Instagram following that's hovered around 5,000 for years. Then she walks through the five things to inspect in every sales conversation, from who's actually driving the call to why "I'll get back to you" means something broke earlier than you think.

Because you can't scale what you can't close.

✨ Year on the Wall 2027 | $47

December 1–4, 2026: now a 3-day virtual event (plus a bonus day).

Link coming soon, mark your calendar now.

✨ Sold Out Group Programs

Join the waitlist: https://stephcrowder.com/mastermind

Connect with Steph
Instagram: @heystephcrowder

This is Day 2 of Steph's five-part daily series on finishing this year stronger than you started, and today she's making the case for radical simplicity.

Steph breaks down why more offers feel safer but perform worse, the finite-energy math that explains exactly what happens when you split your focus six ways, and why she has committed to selling one single offer this entire year. She also shares what she watches happen when clients finally put the blinders on, including the client who went from making ninety-six dollars to over 15K in six weeks.

✨ Year on the Wall 2027 | $47

December 1–4, 2026: now a 3-day virtual event (plus a bonus day).

Link coming soon, mark your calendar now.

✨ Sold Out Group Programs

Join the waitlist: https://stephcrowder.com/mastermind

Connect with Steph
Instagram: @heystephcrowder

This is Day 1 of a brand new five-part pop-up series, dropping every day this week, built around one idea: what if the back half of your year was stronger than the front half? Not by working harder, but by finally flying with a flight plan.

Today Steph walks you through setting your control panel. She breaks down the two goals every business needs before it can finish strong, the three-number framework she uses with her mastermind clients, and the one type of goal almost nobody sets (even though it's the only one you can actually control).

If you've been giving it everything you've got and quietly hoping you land somewhere you like, this episode is your starting point.

✨ Year on the Wall 2027 | $47

December 1–4, 2026: now a 3-day virtual event (plus a bonus day).

Link coming soon, mark your calendar now.

✨ Sold Out Group Programs

Join the waitlist: https://stephcrowder.com/mastermind

Connect with Steph
Instagram: @heystephcrowder