How Do You Know If You’re Ready to Go All In on Coaching?

Last week, on a sales call, a really experienced leader + trained coach asked me a question I hear all the time:

“How will I know when I’m ready to go all in on Coaching?”

And I’ve been thinking about it ever since!

Because here’s the truth — you might not ever feel ready. At least, not in the clean, certain, fear-free way you might be hoping for.

In this episode, I’m sharing a personal story about my own “all in” moment, the psychology of regret (and why it keeps us stuck), and the subtle self-doubt patterns that make thoughtful coaches hover just on the edge of beginning.

If you’ve ever felt almost ready… come and listen!

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Website: www.saspetherick.com | Instagram:  @saspetherick

Transcript

SPEAKER_00 0:04

Hello and welcome to Courage and Spice for Coaches, where you build your self-belief and your business in under 30 minutes a week. I'm Sass Petherick, your host. I'm a coach, supervisor, and unapologetic self-belief nerd. My mission is simple. I want your coaching practice to feel like a right fucking bitch. Let's go. So how do you know if you're ready to go all in on coaching? I had a lovely sales call last week with an amazing woman who has heaps of experience in her existing role, really senior person in corporate. She's also trained as a coach. She's had loads of experience in pro bono work and doing some mentoring in her current role, but she hasn't quite made the leap into building a practice. And so her big question was, how will I know I'm ready? And I've been thinking about this so much. Because so many of us will wait until we feel ready, right? We wait for a sign, we wait for that sense of yes, today this is it, I'm doing it. Then we wait for a signer sign, right? Am I ready to start the business, to go all in on coaching, to take a risk, to really devote myself to this dream that kind of has me. Well, I wanted to spend a little bit of time today just talking about like how do you know if you're ready to go all in on coaching? And I guess I want to start by saying, honestly, I don't think this is a really helpful question. Because when you ask, how will I know I'm ready? What you're really asking about is an emotional state. How do I know I feel ready to go all in on coaching? And that means your answer, your response to that is always going to be a reflection of your emotional state. So it's going to be fleeting, it's going to be very, very changeable. One day you might feel quite brave, and an hour later you're a bit worried. Or the next day it could be, I'm quite hopeful. Yeah, I can see the possibility. By the following Tuesday, you've resigned yourself to just showing up at your day job with all your coach vibes on. Because who can have dreams of running a business in this economy? Right? I know for me, depending on the time of my cycle, I can feel anything from deep excitement to pre-grief over the course of an hour. So because our emotions are all so temporary, I don't think this question is helpful because you're never going to get a clean answer. And the truth is, there is unlikely to be a time when you feel only certainty and ripeness and courage and alignment, all those good things that we wait for. Like I don't think that really ever happens. Certainly not in a sustained way. But the good news is, I don't even think you really need to feel like that. I don't think this is worth waiting for. I think there's a much more grounded and supportive way of approaching this kind of big decision. So I want to go off on a slight tangent that I promise, sort of picky promise, is relevant. So if you've been listening in for a while, you may be aware that just over a year ago, I made a decision to figure out how to live in my body. Like I wanted to create a real sense of healing and home around my relationship with my body. And just to give you some context, like I first went to Weight Watches when I was 11. I've had more than four decades of feeling like my body wasn't to be trusted. I never felt like I could completely relax around food because every time I did, I just went into a kind of full permissive mode and I put on a lot of weight. I never really enjoyed exercise. It always felt like punishment for overeating. So I was just stuck for more than four decades in a pretty unsatisfying, shitty cycle. Couple this with all of the rubbish from the food industry and diet culture, the misogyny that surrounds our bodies, right? Like I think every single woman I know, we've experienced a kind of I don't know, it's like our bodies feel like a foreign country, and I never felt like I learned how to speak the language of it. Added to this, I also have a chronic heart condition. I live with what's called active heart failure. Fun title. And so there is a real and quite present sense that my body is fragile in some ways. And on top of that, heart condition that I've had my whole life, I've got a lot of medicalized trauma from having to consent to strangers touching my body since I was a kid. I only learned in the last couple of years that this was a thing. So no wonder my body feels like the sight of so many uncomfortable emotions, so many difficult memories, all of that. So I made the decision just over a year ago to figure out how I can have a healed and safe relationship with my body. And just to put this in the context of going all in on coaching, like I went all in on figuring this out. Living with peace in a body that felt strong and well fed seemed to me a both a profound and deeply longed for, and at the same time, impossible dream. Like so many of us, when we see posts about coaches with booked-up practices and they're working with clients they adore and a business that just seems to work, like the longing for that. Well, honestly, the only thing I felt at the time of starting that body journey was deep frustration. I did not feel ready. I was pissed off at the unfairness of my genetic makeup. It seemed to me that I could figure out everything else in my life, but not this. I was really jealous and quite projecty jealous, you know, that real icky feeling of petty judgment of other women who seemed to just have this effortless relationship with their body. And it was this constant low hum of why can't I do this? And I wasn't just pissed off, I was scared because since I've entered my 50s, I've got this louder, much louder than ever before sense of mortality. Like I'm in the second half of my life, it's kind of it's all you know, much most of my life is behind me. And my mum died of the same heart condition 20 years ago. She was only 53, which is the age I will be at my next birthday. So, how will I know I'm ready? Right? Like this question was not helpful because I was never going to feel ready. I just had so many thoughts and feelings about the whole thing, it felt completely jumbled. And I share this because I know from talking to so many coaches that you know, before we start our practices, and I felt a bit of this too, that all of those jumbled thoughts and feelings can coalesce into a sense of, oh, it just doesn't feel right, I don't think I'm ready. And I want to share this because we are now a year down the track and I have never felt this good in my body. Like I'm walking around 5k three miles every day, I work out three times a week, I'm lifting heavy weights, which I love. I look forward to going to the gym. Consistency is no longer an issue for me. Um, I eat out, I know what to choose to eat. I've never felt this well fed. I have three like volumous meals a day. I have snacks if I fancy them. I have a little bit of chocolate every evening. There's no food weirdness, like everything is on the menu. I just know what really works for me. Um, and I'm 20 kgs lighter than I was this time last year. I'm starting to get some definition in my traps and biceps, which is un unbelievable to me. Like I fit into clothes I love, I'm sleeping so well, I have minimal menopausal symptoms. Before I started, I could not have imagined this for myself. I had no idea how to get to here when I was starting out. And I want to share this because there are so many similarities around building a business and building a body, right? And the first thing to say is you're unlikely to feel like starting, like you're unlikely to have this sustained experience of feeling ready, and that's because of the nature of feelings, right? But also because I don't really think we know what we're supposed to be ready for. Like when we're starting out, how could we possibly know? We never we've never done this before, we've not stayed the course, not until we reach a point where we're like, oh no, I know what to do now. I know what to do here, I I'm I'm good. And I feel like I'm just reaching that stage now with my body where I really trust it. I think it took probably three years of building my coaching practice before I felt like I understood how all of the pieces of that fit together. I'm still learning and will continue to learn in both realms. But I thought, what an interesting kind of parallel, and what have I learned about how to feel ready? And that maybe you don't need to know how to feel ready, but what do we do instead? So here are a couple of things that might help you to decide now is the time. And I just want to say, right now, like at the time of recording this, it's the end of March 2026, the entire universe is at your back right now, like astrologically, this is a biggie. We've got this rare Aries kind of cluster where loads of planets are in a conjunction in Aries, which is the very start of the zodiac. So some of these like real era-shaping planets are in the mix, it's a once-in-a-lifetime kind of reset. Aries is the beginning, it's the spark, it has very much like let's go energy. So if you've been waiting for a sign, honestly, that might be it, right? So, how do you know if you're ready to go all in on coaching? I really would start by just gently challenging the premise, right? Because what you might really be asking for or asking yourself is something different. I think when we ask, how do I know if I'm ready? What we're really asking is, how do I know this will work? How do I avoid making a mistake or screwing up or failing outright? How do I do this without feeling exposed or vulnerable or judged? Right? So often I think when we're asking, Am I ready? What we're really asking for is can I guarantee I'm gonna be safe? And I just don't know if you can wait for that kind of certainty. Right, instead, I think it's more interesting and helpful to think about the sort of reasons why you might really need that sense of safety. And I think there are a couple of kind of protective patterns that can show up here, and they often sound really sensible, but they can keep us stuck in this kind of holding pattern. So, one is about overthinking, where we need some certainty, right? And it can sound like I just want to do one more certification so I can feel really solid before I start charging. Or I don't think my messaging is quite right yet. I'm gonna get clearer before I put anything out there. Or maybe I've got the wrong niche, the wrong offer, the wrong price point, and I don't want to get it wrong, so I'm gonna stay overthinking. Right? So it kind of looks like being thoughtful and considered, but it feels like needing certainty. Another pattern I see all the time, it looks like productivity, but it's really about control, and that's overworking, right? When you're rewriting your offer or your website or kind of flipping your niche again instead of just working with people, or you start filling your week up with kind of low-impact tasks, you know, getting the right Canva graphics or organizing your inbox, consuming more content from other people, maybe creating multiple offers, starting, you know, to sort of spread and dilute your message across multiple offers, and then not following through on any of them in any real way, right? So we're just in that kind of productivity overworking place, and that can feel like you're making progress, but you'll know that you aren't because no one's buying. Another pattern I see, overgiving. This looks like generosity, but it feels a bit like self-sacrifice, right? I know I can only feel safe if I'm needed here. So this can look like offering lots of free sessions and workshops, um, doing a lot of pro bono work, but never quite making it into a paid offer that you can stand behind, or pouring energy into things that never require you to actually create any boundaries, right? So you're maybe commenting in community spaces or putting all your energy into social media rather than actually looking at how do I specifically speak to the clients I want to work with, how do I market, how do I sell? You might be saying yes to a lot of collaborations or helping other people or supporting other coaches and working in that kind of like peer-to-peer coaching rather than prioritizing paid work. And this is not to say that there isn't space for generosity and free offers, but when that's all you're doing, it's usually a sign that you're overgiving. You've got to kind of take care of you first. The other pattern, right? So we've got overthinking, overworking, overgiving. The fourth one is overwhelm, and it looks like being stuck, and it feels like everything is too much, and I don't have enough capacity. So it's where we avoid a whole lot, right? Because posting, emailing, selling feels like too much, and it's never the right time. Um, it's like looking at the bigger picture, like if I want to be working with half a dozen clients while I wind down my day job, um, that just feels too much. So we shut down or procrastinate endlessly rather than looking at okay, what do I actually need to do here? And it also often looks a bit like freezing when it comes to actually being visible. So we never send the email or make the offer or have the conversation, we spend a lot of time sort of faffing around with the possibility of things. The trickiest part of all of these patterns is that they all make total sense, they're very intelligent, often quite sophisticated, protective responses. And they're also the reason that so many thoughtful coaches stay in this place of one day I'm gonna feel ready to go all in on coaching. Today is not that day. And I also don't want to take away from the very real actual constraints about not feeling ready, right? Like financial reality and time and caregiving capacity, your health and life circumstances. Like, oh my goodness, of course, we want to take into account the wider context of your life, and all of those conditions deserve a ton of respect and thoughtful pacing. None of them are reasons to not start, right? And I think part of the work is learning to tell the difference between what's protective and what's just real impractical, right? So, what I I'm hoping you're hearing here is that readiness is not a feeling, right? I think it's a decision. You don't wait to feel ready, you create a sense of readiness by deciding and moving. So it's not something you'll find, it's something you create, you choose it, and you you know do it at a pace and in a way that allows your nervous system to feel safe. So I think there are really good signs that you might actually be ready, right? Um, even if you're waiting for a signing assign, right? So things like you just really care deeply about this work, right? And you'll kind of know that because you're reading about coaching, you love kind of reading self-help books or psychology papers, or you're following a ton of other coaches, you're looking at coaches and going, oh, that's what I want. One day I'm gonna have that. You're listening to podcasts like this one, right? You care deeply about the work and you're kind of in it, you're just not part of it yet. I think as well, you might be also be ready if you're willing to be seen as a coach before you feel like it's fully part of your identity. It's like, yeah, I'm I'm I might think I'm a coach. Like I've been trained, I'm doing this thing, I'm trying it out. Right? And and you you've got some willingness to go, yeah, I'm gonna, I'm gonna put on this brand new pair of pants, my coach pants, and I'm gonna, you know, wear them in. They might not feel like they're fully comfortable on the first couple of wears. And so what that really means is that you're willing to tolerate some uncertainty, some wobbles, right? A sense of like, oh, it might not always feel like a hell yes. Like that just makes you a thoughtful, nuanced, complex person, in my opinion. And so you're open to learning through doing, not just thinking about the thing. Like you're willing to take some steps, not just plan them. So all of that is about recognizing that you know, your your sense of self-belief around this new coach identity is something that will grow over time with experience, right? Confidence is a is a kind of outcome of competence, and that requires a bit of courage. You need that willingness just to take the first step and then the next step, right? And mostly I want to share this because I think that when it comes to our big profound dreams, I don't think the real risk is failure, I think it's regret, and there's a ton of research around this that people consistently report that they regret the things they didn't do more than the things they tried and it didn't quite work out. And this is out of some long-term studies on regret by particularly Thomas Gilovich. He's done some really interesting work on this. As humans, we're highly motivated to avoid the feeling of regret. So we don't just make decisions based on what we want, we make them based on what we'll feel safest to live with later. That's often what's underneath that question. Am I ready? It's like, oh, I don't want to avoid making the wrong move. And that instinct can work in two directions, right? We might anticipate the regret of taking action, right? Like, what if I do this and it doesn't work? Which tends to keep a lot of us stuck or overthinking, endlessly preparing. But we can also experience a lot more regret over in. Action. Like, what if I never do this? What if I don't do this? What if I stay at my day job forever, or I stay on this current path where I kind of know how it feels, and I never really do it. Over time, it's often that second kind of regret, the regret of inaction, that's the one that stays with us, not the things we tried, but the things we don't. So I think part of this work isn't really about getting rid of the fear or the risk of failure. It's about noticing what's the future you're orienting towards now and choosing the regret you believe you'd be willing to live with. And I'd also say, like, sometimes just phrasing this a different way can shift it. Like the idea of going all in is often a little bit, ugh, you know, I don't know, quit your job, burn the boats, burn the bridges, whatever you set on fire, and these things. That whole idea of just leap and the parachute will appear. I mean, that kind of sense of all in can for me anyway, makes me panic. It feels urgent and a lot of pressure and a lot of all or nothing thinking goes into that. So much the same way that building a body that you feel really safe in and proud of, the only real way to do that, I think, is to take care of it like you love it. Similarly, the only way to find out if being a self-employed coach really works for you is to create a coaching practice that you really love. Right? So it maybe it's not about going all in, maybe it's about building in a way that feels good in your body. For me, I'm way less interested in whether you go all in, more interested in whether you're building something that you love and that you can actually stay in. So, you know, even just asking yourself, like, what would it look like to just take this really seriously for 90 days? What would that look 90 days look like as a courageous and resourced experiment? Why, like, what if I could get three clients in 90 days? What would I need to do if I was taking myself super seriously? You know, maybe it is about really creating one clear and compelling offer, showing up consistently, being willing to experiment with visibility and seeing if you like it, rather than telling yourself a whole lot of stories about it all. And look, if you find this tricky to do on your own, same. Like I spent 40 years thinking I kind of knew what to do to take care of my body, and then I worked with my coach, Sarah, and in a year I have unlearned so much. I have shortcut so many blocks. I think knowing what to do is only half the picture, and you can't really know if you've never done it before. It makes such a difference to have someone in your corner while you do it. Especially when self-doubt kicks in or when things just don't go to plan. So, look, I've spent 15 years figuring out how to create and build and grow a multi-six-figure coaching practice, working with muggles predominantly. And yep, I've had 100k launches, I've had a waiting list of over 300 people at one time, I've had a come to Jesus moment of realizing I actually don't love running a big hairy business. But these days, partnering with thoughtful coaches who want to build a really beautiful, helpful, right-sized for you practice, who really give a shit about the craft of coaching, these multidimensional, fascinating humans that we get to work with. Like that is my love language. And that's why I've built Ripen. It is a true mentoring partnership. It means you have me in your business cockpit for an entire year. You get holistic, personalized, tailored support for you, for your practice. I've got a loose 5S framework for self-belief, strategy, sales, service, and scale. So we focus our time where it matters most to you. And you know, I think one of the things I really love doing and I'm quite good at is figuring out like how to apply these elements to help you build your practice wherever you are meeting me from, like however much experience you have, or whether you're just starting, and while I can't predict exactly what it's going to look like or how fast it will unfold, what I do know is if you're willing to experiment and learn how to play the business game, which I promise you is not as complicated as a lot of people make out, then there is a recipe for a coaching practice that you really freaking love. So, look, if you know you're kind of ready, but maybe waiting for a sign, like apply for ripen, let's have a chat and see what that 90 days might look like, those first 90 days might look like, and what support I can offer. And if you're not ready, like please know I'm going nowhere. There is no forced urgency here. I trust you to know when the time is right. If you are enjoying the podcast and listening in on a weekly basis, it would make my day. If you wouldn't mind subscribing or leaving a five-star rating and a review, perhaps a note of what you're enjoying about the podcast, that really does help people to find this work. Thank you so much, my love. I will see you next time.