Coaches,
September always gets me. Even years past my last first day of school, something in me still perks up at the sight of a fresh notebook, new pencils. That feeling of “okay, this is the year.”
I think that feeling is worth borrowing right now, wherever you are in your business. September gives us permission to sit back down at the desk, open to a clean page, and get honest about what’s actually in our way.
So that’s what we’re doing this month. I’ve been collecting the obstacles I hear most from coaches, and three keep coming up louder than the rest. If any of these sound like you, you’re in very good company, and you’re about to get some homework you’ll actually want to do.
Obstacle #1: “I love coaching. I don’t love finding clients.”
This is the most common thing I hear, and I want to name what’s really happening underneath it. Most coaches don’t dislike finding clients. They dislike the version of “finding clients” they’ve made up in their head, the cold, transactional, please-like-me version. That version is exhausting because it isn’t you.
Here’s the reframe: outreach isn’t selling. It’s serving out loud.
When you reach out to someone, you’re not asking them to like you. You’re offering to be a problem solver for something they’re already struggling with. That shift, from “do they like me” to “how can I serve,” changes the entire energy of the conversation. You stop performing and start connecting.
Your homework this month: Pick three people who’ve crossed your mind lately, a past client, an old colleague, someone you admire from a distance. Send one message to each, not asking for anything, just offering your attention. “I’ve been thinking about you. I have 60 minutes on my calendar I’d love to gift you, no strings, just space to think out loud about whatever’s on your mind.” That’s it. That’s outreach done right.
Obstacle #2: “I don’t want to talk about money, and I don’t know what to charge.”
Let’s start here: your discomfort around money is a sign you’re doing something that matters. Money conversations feel high-stakes because they are, you’re asking someone to invest in themselves, and most people have complicated feelings about that.
Two things will change this conversation for you immediately.
First, language. Stop saying “cost” or “price.” Use “tuition” and “investment.” Those words tell the brain this is growth, not a transaction, and your potential client will feel the difference before they can articulate why.
Second, silence. State your number, then stop talking. Let it sit. The urge to fill that silence with justification or a discount is enormous. Resist it. Their pause isn’t rejection, it’s them doing the work of deciding if they’re ready. Interrupting that pause takes the decision away from them.
Your homework this month: Practice saying your number out loud, alone, until it stops catching in your throat. Then practice sitting in silence for five full seconds after you say it, time yourself if you have to. The number doesn’t need defending. It needs to be said and left alone.
Obstacle #3: “There are so many coaches out there. How do I compete?”
You don’t. That’s the whole answer, but let me unpack it.
Competing means trying to be the best version of what everyone else is already doing. It’s exhausting and it’s also the wrong game. Nobody else has your specific way of listening, your specific stories, your specific lens on transformation. That isn’t a marketing angle, it’s the actual thing people are paying for. Coaching is an experience, not a set of features. Nobody hires you for your session count. They hire you for what it feels like to be coached by you.
Scarcity, the sense that there’s only one of you, doing it exactly this way, creates value. Abundance of coaches in the market doesn’t threaten that. It just means you get to stop trying to look like everyone else and start sounding more like yourself.
Your homework this month: Write down the three things about your coaching style that feel most like you, not what you think sounds impressive, what actually feels true. Put those three things in your next outreach message, your bio, your next connection call. Let your specific way of doing this be the thing that draws people in.
Watch This
I recorded a short video walking through how I coach potential clients through money hesitation in real time, using the exact language from my own connection calls.
How to Overcome Money Objections
A Light Ask
Pick one of these three homework assignments and actually do it this week. Just one. If you want more structure and support putting all three into practice, this is exactly the work we do together inside Stairway to Six.
Learn more about Stairway to Six
Here’s to a fresh page,
Gretchen
