Last week, I was on the phone with a founder-to-be. He was flirting with the the idea of starting his own company after leaving his last place of work unexpectedly. We had done three calls, and he had all the signs of a client ready to hire me: he was engaged, motivated, and texting me excellent follow up questions.
He told me he was ready to invest in himself and in this pivot. We mapped out a plan. I sent him the contract...and then...pin drop silence.
When I followed up, he said he was “still not sure he’s ready.” For coaching? For entrepreneurship? I wondered. Maybe a combo?
I get it. I’ve been that person. It's really hard to fork over a bunch of money to someone as an investment in yourself. It's even harder to spend that money on something non-material. There are people who spend $5k on a bag who would never spend that on a professional development course. There's something about a tangible "thing" that feels more "worth it."
I've been this person too. I've stayed in roles that are bad for me for too long because I didn't want to find the support for the pivot. I've delayed launches because I didn't want to hire the expert I needed to execute my vision. I've waited to raise my rates until I feel "qualified enough." Even in my personal life, I waited to get the unlimited gym membership until I was "kind of in shape."
But when I look back at all these moments, I've rarely been ready for the thing that comes my way. Well not at the beginning anyway...so let's get into it.
🧠 Inside This Issue
For those of you new here (👋🏽 welcome!) — this newsletter weaves through the blurry lines of politics, storytelling, leadership, and entrepreneurship — with a human lens and a critical edge. I write about what people are often scared to say out loud. I talk about a lot of hard truths: failures, impossible situations to navigate, and the intersectionality of being a complex human being who also needs to make a living.
This week: → How to overcome "not feeling ready"
👀 When Do We Actually Become Ready?
Ok. I low-key hate when people rely on a dictionary definition to make a point...but I genuinely started to wonder: what does “ready” even mean — and why do we think we need to BE ready before we try something new or terrifying? Can we ever be fully ready for the unknown?
I flashed back to the first time I tried a trapeze class. The instructor clipped me into the harness and jokingly asked, “Are you ready?” Everything in my body screamed NOPE. But I said “Yes!", and then I leapt through the air.
So, what does it actually mean to be “ready”? A quick google search tells me
“In a suitable state for an activity, action, or situation; fully prepared.” Similar: prepared, all set, equipped, primed, obtainable or within reach.
Maybe this is why. Because when we say "ready," there is an unseen and unsaid pressure of being...perfect? Maybe?
Trapezing...starting a business...hiring a coach...hiring my first employee...starting a new job...a new company! All of these things, I'm not sure if I was ready for. But I did them. And after a few reps, I was ready. To do them again. To do them better.
If you’re feeling not ready — that might actually be a sign you’re right on time. Ready to be a manager. Ready to start a business. Ready to give a TedTalk. Ready to hire a coach! These things are scary. They require commitment. But, if they feel too easy...maybe you're too ready. Maybe you're not stretching far enough? And maybe, just MAYBE, once you take the leap, you'll be more ready than you thought.
🧠 Mini Framework: Signs You’re More Ready Than You Think
You’ve helped someone get results, even informally.
You’ve been told “you should charge for this.”
You’ve thought, “Who am I to…?” (That’s a sign you’re stretching.)
You care about doing a good job and are willing to invest in the support you need to do so (which is a better predictor than any degree or logo).
💬 Question of the Week:
What are you procrastinating because you don’t feel “ready” yet?
📣 Things I’m Offering:
→ Power Sessions: A 90-min deep dive to clarify your story, offer, or strategy — especially if you’re making a leap. → Team Workshops: Fall bookings are open. Topics: narrative clarity, leadership visibility, and emotional resilience. → $10K Coaching Package: For creative leaders, founders, or execs navigating high-stakes pivots. (2 spots left for August start.)
A mid-point client survey came in last week — and it lit me up. K.M. is the kind of client I dream of working with: deeply committed to growth, taking the tools we explore and running with them. She’s showing up, leaning in, and investing in her transformation.
This kind of engagement reminds me why this work matters — and why the right client fit changes everything.
If you are looking for a transformation, let's chat.
