Courage & Clarity – Episode 153: Fall in Love with Launching: Stop Dreading & Start Selling More, Naturally

Host: Steph Crowder
Release date: October 8, 2025

Episode Overview

In this insightful and energizing solo episode, Steph Crowder explores why so many entrepreneurs dread launching — and how to rekindle (or discover for the first time) a real love for sharing your work with the world. Positioning this as the first of a three-part series, Steph unpacks outdated beliefs about launching, provides a fresh perspective on today’s business environment, and offers practical wisdom for iterating and thriving in a more mature online market. She encourages listeners to challenge their assumptions, choose the right kind of “hard,” and embrace launching as an avenue for both business growth and personal fulfillment.

Key Discussion Points and Insights

Defining “Launching” (06:10–10:45)

• Steph clarifies her definition: Launching isn’t just for online courses; it applies to any concentrated campaign with a focused sales window — a group program, 1-on-1 services, paid workshops, or even a live event.
  • “It’s really any…concentrated sales window, where you are trying to drive sales, increase clients, increase your customer roster in like a focused period of time.” [08:55]
• Launching often gets reduced to "open cart/close cart," but it's truly about creating urgency and excitement, whether for a traditional program or service-based offer.

The Roots of “Launch Hate” (10:46–27:00)

• Why do so many entrepreneurs dislike launching?
  • Launching is commonly described as “exhausting, depleting, energetically draining.” [10:58]
  • The expectation that a sprint (launch) process should feel easy is one major problem.
  • Distinction: “It’s going to feel like work…but there’s a difference between hard work you choose and misery.” [12:45]
• Market Maturation, Not Saturation
  • Steph traces the industry’s shift from “cut and paste” launch successes of 2018–2021 (few emails/posts, big results) to the present, where the same tactics plateau or underperform.
  • “You could kind of put it out there, you might hit your number or even exceed your number. That was very normal for that time period.” [16:36]
  • Now, we’re seeing maturation — not saturation. Markets evolve, audiences become savvier, new competitors emerge, and what worked "yesterday" requires reinvention today.

Market Maturation: The Groupon Analogy (19:35–27:00)

• Groupon origin story parallels online business:
  • Steph, an early Groupon employee, observed a new market explode, then mature as competitors entered and buyer behavior changed.
  • “What happens in all markets…when the demand was so high, the demand was higher than the supply could even meet, things gradually start to flip…Now we actually have more supply than the demand.” [22:45]
  • The panic and “it’s over” narratives were wrong: successful companies iterated and survived, even if the market looked totally different.
  • Entrepreneurs wrongly interpret maturation as death, leading to abandonment (or disdain) for launching rather than necessary iteration.

Reframing Your Relationship with Launching (27:01–42:10)

• If launches aren’t working like they used to, don’t jump to conclusions (e.g., your offer is dead, people don’t buy online, etc.). Instead, recognize the critical shift:
  • "What companies get wrong and what business owners get wrong is they forget how to be exciting and they forget the spark that made the whole thing explode in the first place. It really is like, you gotta fall in love again." [28:56]
• It’s NOT that launches don’t work anymore. It’s that buyers have evolved: they've gotten more discerning, not less interested.
• Steph uses memorable metaphors:
  • Relationship analogy: Expecting a launch to always feel like it did in 2020 is like expecting a marriage to always feel like its first date.
  • “Pee in the pool” analogy [36:25]: In any crowded pool (market), eventually someone “pees" (i.e., bad actors cause bad experiences), making buyers rightfully more cautious. The solution isn’t to drain the pool; it’s to prove your pool is safe and clean.

Why We Actually Hate Launching (42:11–46:30)

• The REAL reason entrepreneurs dread launching:
  • “You don't hate launching. You hate not hitting your numbers. You hate trying and missing. You hate putting all of it out there on the line and then being like, I didn’t hit my goal. That’s what you hate.” [42:30]
• The answer isn’t quitting or pivoting at the first sign of resistance — it’s iterating, experimenting, and upgrading your approach to meet today's market.

The Stories We Tell Ourselves (46:31–54:22)

• Steph invites listeners to examine the stories in their heads about launching: “It doesn’t work,” “it’s miserable,” “it’s too hard,” etc.
• Caution: Trying to skip discomfort by fleeing to low-price offers, evergreen funnels, or new strategies without processing your beliefs will only bring the same “baggage” to the next idea.
  • “Until you clean up your thoughts about your current strategy, you're going to bring all of the garbage to the next idea.” [49:24]
• "Choose your hard":
  • Is learning to love (and get skilled at) launching harder than not having enough sales? Not having the money you want? Constantly wondering if you’ll make payroll?
  • “What’s really hard is not having enough sales…Launching isn’t hard. Not having enough clients is hard.” [51:10]

Personal Story & Encouragement (54:23–59:30)

• Steph shares her own cycles: excitement, burnout, reinvention, and the professional high of “figuring out launching” again and again over seven years.
• Dopamine from new ideas/pivots is fleeting — you’ll just encounter similar challenges wherever you go if you haven’t done the inner work.
• The value of curiosity over panic:
  • “When I see buyer behavior changing, I don’t get scared anymore. I just get curious. Right? … What am I doing to be interesting? What are you doing to shake things up? That’s how you’re going to fall in love with launching.” [57:08]

Notable Quotes & Memorable Moments

• “The expectation that a sprint should feel easy is probably the first problem.” – Steph Crowder [13:16]

• “It’s not saturated, but it has matured. And if you look at, like any market, this is what happens.” [18:58]

• “People are still spending money. But I'll give you that: they're spending it with more discernment. And it’s actually a good thing… Doubt and skepticism from your prospects in your sales process is actually a good thing.” [37:14]

• “If you’re still launching, hoping it’s going to feel like 2020, you’re going to hate that. Right? It’s kind of like being in a marriage and hoping it’s going to feel like your first date.” [29:45]

• “Choose your hard. If you want to continue to struggle and continue to jump from idea to idea…that is going to be the harder road, in my opinion. The easier road in the long run is to get good at learning new things.” [51:35]

• “I never allow myself to think I know everything about this... There's always more to learn, and the buyer can always educate me. So when I see buyer behavior changing, I don’t get scared anymore. I just get curious.” [57:08]

Important Timestamps for Key Sections

| Timestamp | Segment/Topic Description | |-------------|--------------------------| | 06:10–10:45 | What is “launching”? Steph’s complete, inclusive definition | | 10:46–16:36 | Why launching has a bad rap; energy drain and expectations | | 16:37–27:00 | Historical context: How launches worked pre-2021, market maturation, and Groupon analogy | | 27:01–36:24 | Why launches feel harder now, misinterpretations about the market, and what iteration looks like | | 36:25–42:10 | Buyer discernment, “pee in the pool” analogy, how skepticism creates better clients, spending trends | | 42:11–46:30 | The real pain: missing targets, not the act of launching itself | | 46:31–54:22 | Mindset work: the stories we tell, “choose your hard,” lessons from personal experience | | 54:23–end | Breaking your own cycles, the necessity of reinvention, open curiosity vs. fear, preparing for fresh strategies |

Takeaways & Next Steps

• Challenge your beliefs: If you dread launching, get honest about the stories you tell yourself – and ask if the real pain is from effort, or from unmet expectations.
• Adopt a growth mindset: Markets change, audiences mature, and success requires ongoing curiosity and adaptation, not nostalgia or retreat.
• Iterate, don’t abandon: Reinvention is part of entrepreneurship. Bring energy, experimentation, and “first date” excitement into each new launch chapter.
• Sign up for deeper strategy: Steph’s upcoming “Double Your Launch” class promises hands-on, up-to-date tactics for today’s marketplace (details at stephcrowder.com/workshop).

Next Episode Teaser:
The series continues with the "new rules of launching" — tune in to learn actionable strategies tailor-made for today’s entrepreneurial landscape.

Final Thought:
“The dread that you feel of launching is totally optional. And I want you to know this is something you can learn to love — even if you feel like you don’t have a salesy bone in your body.” – Steph Crowder [59:10]

For more information and links, check the show notes or visit stephcrowder.com.