214: Crossing $500k By Being Boring

YEAR ON THE WALL 2027 --> GET YOUR TICKETDo you have a real revenue game plan for next year, or do you have a random number you picked as a goal because it sounded right?In this episode, Steph continues the annual planning series with the money side of your 2027 plan. She explains why one revenue number is never enough, and why you need three money goals that are tied to the life and business you actually want. She shares the most common mistakes she sees when business owners set a revenue goal: having no goal at all, picking a number at random, copying someone else’s, and tracking income without thinking about what your real life costs.Steph also tells the story of the day she transferred $14,000 from her business account to her family checking account in her laundry room. It was the best launch she’d had at the time, and she couldn’t celebrate it for more than five seconds. She calls the feeling “the financial treadmill of doom,” and she explains what it taught her about knowing your numbers.What You’ll Hear In This EpisodeWhy “I’ll just try my hardest and see how much I can make” is not a revenue planThe four most common problems Steph sees when people set revenue goalsWhat the “financial treadmill of doom” is, and how fast your brain gets used to bigger numbersWhy knowing what enough looks like makes it easier to go after big, scary goalsHow to get honest about the money you need to fund the life and business you want, even if numbers are not your thingWhy good, better and best numbers work better than one, and how they turn into a real plan for your offersSteph’s own math for a million-dollar year, and why seeing the plan on paper changes what you believe is possibleWhy selling from a place of “I’m good” is more magnetic than selling from desperation, and how money clarity makes you a better salespersonWhat it means to keep your feet on the ground and your head in the cloudsPlan your 2027 with me: Year on the Wall, December 1, 2 and 3This episode is part two of the Courage & Clarity planning series. If you missed part one, go back and listen to episode 217.Year on the Wall is Steph’s planning system built on giant calendar pages and colored sticky notes, so you can see your whole life and your whole business on one wall. This year she’s teaching it as a live 3-day series.Day 1, Tuesday, December 1: your biggest year yetDay 2, Wednesday, December 2: your money plan, where you find your three money targets and put the plan on your wall (this is the workbook day for everything in this episode)Day 3, Thursday, December 3: your content planEach day starts at 12 pm ET. You get a workbook for every day, and replays are included. One $47 ticket covers the whole week. If you apply to work with Steph, you can also join the bonus VIP day on Friday.Get your ticket at yearonthewall.com.✨ YEAR ON THE WALL WEEK | TICKETS ARE ON SALE NOWFor 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 ProgramsJoin the waitlist: https://stephcrowder.com/mastermindConnect with StephInstagram: @heystephcrowder

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 planThe real reason most plans are dead by FebruaryHow to plan around your life instead of against it, including the sick seasons, travel schedules and busy months you can see comingSteph’s “life buckets” approach to defining success in every area of your lifeWhat to do when the road closes: how to adapt your plan instead of shredding itWhy “winging it” costs you more than a plan that needs adjusting✨ YEAR ON THE WALL WEEK | TICKETS ARE ON SALE NOWFor 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 ProgramsJoin the waitlist: https://stephcrowder.com/mastermindConnect with StephInstagram: @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 daysHow I paid for a $10K event out of cash flow, and why I see it as an investmentThe first step I took when I had no idea how to plan an eventHow a live event turned into a deadline for new curriculum, branded photo shoots, video footage, and testimonialsWhy I think in-person gatherings will be worth even more in the age of AI✨ YEAR ON THE WALL WEEK | TICKETS ARE ON SALE NOWFor 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 ProgramsJoin the waitlist: https://stephcrowder.com/mastermindConnect with StephInstagram: @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 jobWhy 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 sellsHow to treat your paycheck as a “silent investor” in your businessProof that success takes timeThe 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 WEEK | TICKETS ARE ON SALE NOWFor 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 ProgramsJoin the waitlist: https://stephcrowder.com/mastermindConnect with StephInstagram: @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 everythingThe simple math that made a million feel inevitable instead of impossibleHow going from 2 enrollment periods to 5 created far more offer exposureHow the First Clients Fast Track turned an “iceberg idea” into an on-ramp that converts 10%+ of participants into her mastermindWhy aiming for a million put her on track to nearly double last year’s $350KThe sufficiency goal: the counterintuitive mindset shift that lets you go big without desperationWhy your business can only grow as much as you do, and why you shouldn’t wait to love your life✨ YEAR ON THE WALL WEEK | TICKETS ARE ON SALE NOWFor 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 ProgramsJoin the waitlist: https://stephcrowder.com/mastermindConnect with StephInstagram: @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 underneathThe "scales of justice" framework for tipping the balance so clients aren't only able to pay, they're happy toWhy you need a yes to the plan and the transformation before money enters the conversationHow to make money "just a logistic," using a car dealership as the exampleWhy your clients' finances are none of your business, and how staying out of their wallet works both waysThe 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 differentIf 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 WEEK | TICKETS ARE ON SALE NOWFor 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 ProgramsJoin the waitlist: https://stephcrowder.com/mastermindConnect with StephInstagram: @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 EpisodeA 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 integrityThe concept of "desperation breath" she learned from her Groupon sales training days, and why both sides of a desperate conversation can feel it radiatingThe 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 clientThe "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 WEEK | TICKETS ARE ON SALE NOWFor 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 ProgramsJoin the waitlist: https://stephcrowder.com/mastermindConnect with StephInstagram: @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 EpisodeThe 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 offerThe 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 pointHow inviting mastermind clients into the fast track turned six people into a party of 21 before she even opened the webinarThe 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 anywayThe Post-it note exercise she used to get into gratitude for her first six clients instead of chasing moreWhy 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 scaredHer "court case" framework for managing a brain that's only showing you the bad evidenceThe quarterback analogy for knowing when to swap out the driver in your own launch✨ YEAR ON THE WALL WEEK | TICKETS ARE ON SALE NOWFor 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 ProgramsJoin the waitlist: https://stephcrowder.com/mastermindConnect with StephInstagram: @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 EpisodeWhy this moment in 2026 feels like an echo of 2020 -- the same rush-to-strategy pattern, just with AI instead of a pandemicThe 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 itWhat led her to shut down her business, lose 200 podcast episodes, and step away entirelyWhy 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 thoughtWhy she believes "when something is clearly AI, it does break the connection to the person" including her Pinterest ad and Instagram caption examplesHer 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 hardQuotable 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 EpisodeAre 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 WEEK | TICKETS ARE ON SALE NOWFor 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 ProgramsJoin the waitlist: https://stephcrowder.com/mastermindConnect with StephInstagram: @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 everythingThe 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 experienceBonding through simplicity: what happens when cooking, cleaning, and decision fatigue disappear for three daysWhat three days with no phone service taught her about her own brainThe idea of "growing capacity," and why the conditions being hard didn't cancel out the goodCuriosity over judgment, and how pre-deciding you already know the ending (in a launch, a sales call, a project) quietly kills opportunityThe story behind the episode title: a camp program director, a locked box of marksmanship equipment, and the mantra she uses to stay calm under pressureThe Improvise, Adapt, Overcome framework, and how Steph is already using it with her own mastermind clients✨ YEAR ON THE WALL WEEK | TICKETS ARE ON SALE NOWFor 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 ProgramsJoin the waitlist: https://stephcrowder.com/mastermindConnect with StephInstagram: @heystephcrowder