The Hilary Silver Podcast - How to Start Over and Succeed: 6 Powerful Lessons

Episode Date: March 21, 2025

Starting over? Again?! If the thought of making a major life change sends you spiraling, it’s time for a reality check—starting fresh isn’t scary, staying stuck is. Hilary shares the six biggest lessons she’s learned from reinventing herself—multiple times. She’s built and walked away from thriving businesses, started fresh, failed fast, and bet on herself—again and again. And now? She’s giving you the real talk on what it actually takes to start over (and make sure it pays off).   Episode Highlights: Get clear on what you actually want (spoiler: most people aren’t). Why being half in, half out is a guaranteed way to stay stuck Failure isn’t a thing. Not trying? That’s the real failure. Why betting on yourself is the safest investment you’ll ever make   Episode Breakdown: [00:00] Why Starting Over Feels So Hard [03:52] The #1 Mistake People Make When Reinventing Themselves [05:06] How to Fully Commit to Your Next Move [07:04] The Power of Mindset [09:55] Burnout, Fear & the Power of Letting Go [12:13] Redefining Failure: What You’ve Been Getting Wrong [14:08] Betting on Yourself is the Secret to Lasting Success [16:14] Starting Over (Again) & Why It’s Worth It [19:25] You Have Nothing to Lose 💥 Ready to bet on yourself? Hit play.   💫 Subscribe to Hilary's YouTube Channel: https://www.youtube.com/@HilarySilver?sub_confirmation=1 🔥 Grab Hilary’s FREE training, This Changes Everything (and other free resources!): https://hilarysilver.com/guides/ 👉 Follow Hilary on Instagram: @hilarysilver   🚀 What’s your biggest reinvention lesson? Drop it in the comments!

What if I told you that starting over, changing careers, walking away from something, successful or not, or being a beginner again in midlife doesn't have to be terrifying? And that you don't have to be in a bad place to want more. I've started over not once, but three times in the last eight years. And each time that I did, I walked away from something very successful and lucrative simply because I wanted something new. I just wanted to. So whether you're thinking about making a change or not, this episode is still for you because the six lessons that I've learned from all of these restarts are important life lessons that we all need to hear. And if you are considering taking a leap,

by the time that we're done, you're going to understand the secret to making sure that your big bold move is the right move and how to make sure that it pays off. And stick around till the very end because I'm saving my juiciest one for the last. Hi, it's Hillary. Welcome to the Hillary Silver podcast. Thanks for tuning into the conversation today. If you haven't already, it would mean so much to me if you take a minute to just click that five star rating on your podcast app, leave a review and subscribe so you never miss one of my episodes. And if you're enjoying this podcast, please consider sharing it with a friend because if you like it, they will probably like it too. The first time that I started over was in 2017

when I walked away from my thriving therapy practice, one that I had built over 14 years. It had a two month wait list and it was mostly referral based and I had therapists working for me. And I loved what I was doing. So it was really just pretty successful by every measure. But as time went on, I began to crave more.

I saw that my methods were getting amazing results for my clients, and I just felt confined. I felt constricted, and I wanted to help more people and make a bigger impact. And just that little nugget of an initial desire eventually grew into a deep yearning for me. Like a deep yearning. And the best way that I can describe it is to use the words of Anne Lamott, the writer, the way she put it. She says, I don't write so that I can publish. I write so that I can

breathe. And that is exactly how it felt to me. I thought about it day and night. I was obsessed. And that's really when I started my habit of waking up at 4am because I had to find the time to work on it because my kids were still little and I was still running my therapy practice. I jumped right in. I bought courses, I created courses, I hired coaches, I started putting out content. I even got featured as an expert on the Steve Harvey show. All in all, I spent four years for long years, and $100,000 in all of my trial and

error trying this and trying that. But I was doing both. I was running my practice while building what would eventually become Ready for Love. And it was honestly excruciating because I felt stuck in this transition. We often don't recognize how difficult transitions are. It's that limbo of still being where you were and where you have been and not yet quite where you want to be. And so it was really tough doing like that four years.

And I will say it was worth it, of course, because I built what became one of the most successful women's love and relationship programs in the world. It's a multiple eight figure company, and we have helped thousands of women completely transform. I wouldn't be where I am today if I were to change any of that, but I learned some seriously hard earned lessons in that time, and that's what I'm gonna share with you now

So the first big lesson from this reinvention is this be clear? What you want and what you are creating and while that might seem obvious we often aren't very clear What our vision is we just want something we want to feel something or we want this big Grandiose idea of something but we're not really clear what it actually looks like in every way. There's a lot of variables and a lot of things that can be up in the air. So for me, for example, my entire education and background and expertise is psychology, not business. And while I had built a very successful therapy practice, and that is a business model, I

hadn't really thought about it that way. And I don't think I was very intentional about what I built. It just came easy to me. So had I been crystal clear about what exactly I was building and creating, what I was offering, how I was going to deliver it and get my word out and get the message out, it all would have happened so much quicker and it would have saved me a lot of time and money and heartache. And because of this lack of clarity, I doubted myself a lot and what I was trying to create

so much so that when something wasn't working fast enough or what I was trying at the moment didn't work out right away, I just jumped to another thing. I would just create another course because teaching is easy for me. And I would try a new way to get it out there to people so that they could find me. So I became this jumper and I just chased my tail in a frenzy of activity to get there. That's what I used to call it. I

want to just get there. That was my clarity, get there. And so while I couldn't see it at the time, I had become my own biggest obstacle despite all my exhaustive efforts. But when I finally figured out my plan and it was crystal clear, within one single month I closed my practice for good. So for you, whether you're thinking about starting a business or leaving a relationship, being clear about this new thing that you are creating is important. And so that leads me to lesson two. After you are crystal clear and you have your plan, be all in. So maybe you've heard this phrase before, burn the boats, which is exactly what I did. Once I knew exactly what I was building

and I had the blueprint for it, I closed the therapy doors for good. There was no going back, no more straddling, no more safety net, no more, if it doesn't work, I'll go back. I was all in on my goal, on my vision and on my dream. So here's the thing, people stay in relationships for years being half in and half out.

That limbo is excruciating. It's kind of like, should I stay or should I go? One day it's good, so you're in, and the next day it's bad, so you're out. People think about moving or starting businesses for years stuck in the learning phase, the information gathering phase, never going all in on it. And you just can't half-ass anything and expect full-ass results. You have to go all in and not look back. My biggest lesson of all in this very first restart is this. Do not underestimate the power of your mindset. Of all the challenges that I faced in that time, I was the biggest one of all and I didn't even know it. I had all the coaches and all of the programs and all the people that I had hired to help

me along the way and they were all focused on tactics and strategies. But none of that was ever going to matter so long as I was standing in the way. I was my own biggest obstacle, deep down believing that I didn't have what it takes, doubting myself, and that success is like that kind of success is for everyone else, but not for me. Even though intellectually I knew that what I had to share was amazing, and I had all this evidence to prove it with my clients telling me how much they love their work with me and how much better their lives are. So I got it intellectually, but there was still

this stubborn, deep down, limiting belief that I couldn't do it, that I didn't have what it takes. And I began to identify with the struggle, telling the struggle story over and over of how I'm stuck and why I'm stuck and how all the things that I had tried hadn't worked. So don't neglect to focus on your own growth in the restart process because your identity is everything. And it is the critical key to whether whatever it is that you're about to start works out for you or not

Identity is who you are It's who you think you are what you believe about yourself and what's possible for you and how you talk to yourself So keep this phrase in mind Identity work is the bridge between where you've been and everything that you're meant to have Okay, and I'm gonna come back to this at the very end, so make sure you stay with me. So moving on, at this point, it's five years later, 2022, I've done more with Ready for Love than I ever could have possibly imagined. I did it. Ready for Love is this massive success that I didn't even dare to dream about. Thousands of clients, countless success stories, and a team of coaches and enrollment team, all the admin support I

needed. And our revenue just doubled year after year into the many millions. And I have to say, it was life changing in every way. And then I walked away from all of it. I literally shut it down and turned off the lights, literally hit the off switch. And let me tell you, no one understood it. My friends, my family, my team, even my clients were shocked and unhappy about it, but I was burnt out. The burnout was sneaky because it hid beneath

all the adrenaline and the complete joy and thrill of all of our client wins and the lifestyle and the freedom that came from the money. But I was exhausted and I felt trapped and I wanted to continue doing new things, but I just felt like I couldn't. I had no capacity for anything else. And I was just so embedded in the business that I didn't know how to make room for anything else. And so I know it seems crazy to walk away from my $12 million coaching company that I had built.

It was my labor of love. It was four years in the making and then five years of just building it and building it. And it really was the highlight of my life thus far. But I stepped away for nearly a year to catch my breath and get perspective and figure out what I wanted to do next because I just again craved more. I wanted something more. And in that time I experimented a lot. I got involved with a couple of projects that never

got off the ground and I hosted an elite mastermind with women entrepreneurs. It was amazing. And in that time I learned a few more very important lessons that I'm gonna share with you now. First, which is lesson four, I redefined my relationship with the word failure. Failure isn't real. Call me delusional, but I don't believe in failure. You only really ever fail if you never try at all.

You fail before you even start if you never start. So many people are afraid of failure and that prevents them from trying anything or starting anything or putting themselves out there in any way. So this reframe is powerful because when you think about it this way, you have to go for it

or your biggest fear is already realized. You failed just by not trying. It was Alfred Tennyson who said, better to have loved and lost than never to have loved at all. And I believe this is true for trying. And what I say is, better to have tried and missed than never to have tried at all. And notice I didn't say tried and failed because it's just not a thing. A try and a miss is noble. It's commendable.

It's identity expanding. It is not embarrassing or something to be ashamed of. There is no tail between the legs, nothing like that. And never to try because a fear of a failure is just sad. Think about all the missed opportunity and potential. It will be something that you will always wonder about. And not just for you, by the way, but what you don't put out into the world

is a missed opportunity for everyone else. What is out there for everyone else when you hold yourself back? It's like the phrase, the one that got away that we say about potential love. Don't let this big idea or opportunity or restart be the one that gets away. The biggest regrets that we have are not the things that we have done, but rather the things that we haven't done. So if you have a desire for something more and you never even try, you will always wonder what could have been. What could have been? And you won't regret having tried.

You just won't. You will regret not trying. I guarantee it. How many times have you or someone that you know had a great idea and you or they talked about it a lot only to not do something about it and then later finding out that someone else had the same great idea and took action and created something wonderful and successful from it. It could be you. Why not you? And this brings me to my last restart. In 2023, I turned the lights back on with Ready for Love. I just missed it so much for so many reasons. But this time, I'm wiser and I have the perspective that I needed. In that time, I grew myself and I came back ready to work smarter, not harder. And this again, is bringing us back to the concept of identity. How I see myself and think about myself has been expanded.

I am now the founder rather than a love coach. This new expanded version of me thinks differently and it guides my decisions. Because of this, I'm actually helping more women than ever before because I'm not down in the weeds running everything all by myself, but instead getting the right help. So within 12 months, we were already back making multiple seven figures, again, which just reflects how many women we are helping.

And I'm doing it without all the burnout. So here's how this translates to you, my lovely listeners. The big lesson here, number five, if you're not willing to bet on yourself, what can you bet on? In this life, if you are not a guarantee, what is? I learned I can do anything. I built a company to 12 million and then did it all over again from zero. And if I can do it, you can do it or whatever it is that you want, just do it.

You can do it. And it is about putting all your faith in you. You are the one and only thing in this life that you have control over. And if you are not a guarantee, what is? That is probably the most powerful lesson that you're gonna get out of this today. But this brings me to my last restart. Once Ready for Love was back up and running and done in the smart way, I did have the capacity for more. And that brings me to this podcast and this YouTube

channel. All the work that I've been doing, first in my therapy practice and then exclusively for my single women clients, those people who can afford me, it is now my mission to share what I know with everyone because I truly believe it is what we all need to live our best life. So exactly one year ago today, when I was 51, I decided to start this show. And I have to be honest, it's been very humbling to say the least. I have all this experience and all these results for my clients

and have had all this success kinda just while flying under the radar. I've been quietly doing this work for so many years. I've done it all without a large audience. I'm kind of an unknown. Nobody really knows who I am. And that's fine with me, except here I am being a beginner

at this point in my career. Starting this show with zero subscribers, zero listeners, zero followers is just hard. I'm not gonna lie. Showing up every week and sharing what I know and just hoping that I get seen, hoping that I get heard, and feeling like no one is listening sometimes,

I'm talking to no one. It's definitely humbling. And sometimes when I publish a video and it doesn't get hardly any views, my initial reaction is, oh, they don't like me. And I can feel that old deep deep, automatic rumbling inside of me that I mentioned earlier. I don't have what it takes.

Or maybe I don't deserve this. Or maybe I'm not good enough. And it's in there for all of us. But these experiences, these new experiences, are triggering that for me again in a different way and in a new way. And sometimes I wonder, why am I doing this and feeling like maybe I should have started this years ago

and who am I to start this now? And all of that stuff kind of just goes in my head. But then I remind myself I'm right where I'm supposed to be. I am not here for acceptance, for recognition, or for any of those things, nor am I here to prove to anybody or myself anything, but to help and share, because that's what my mission was to begin with, to share what I know because I'm blessed and I'm able to do that. And if one person hears me and

it helps one person, then that is it. So be it. It's my mission accomplished. So the final lesson is this. Starting over reveals our edges. Every time I have restarted, I've bumped up against my edges. What does that mean? Your edges are the outermost boundary of your capacity as a human. What you understand, what you know, what

you are aware of, what you are capable of, what you can do, what is healed, what you have worked on. It's the next thing that you need to work on in order to expand yourself, to be all you can be in this life. Your edges are the limits. So inside of the comfort zone bubble, you're confident and sure and certain. But the minute you step beyond them, what happens? That's where you meet resistance and fear and you feel uncomfortable and unsure and insecure. So whenever you embark on a new adventure and every time I have, whether it's restarting a career, starting a business, leaving a long-term relationship after so many years, getting into a relationship after being single for so long, having a baby,

taking a risk of any kind, embrace the experience as an exercise in finding your edges. What still needs your love and attention and healing? What part of you is ready to grow next? What more can you learn about yourself? Push your limits outward to be fully expanded. This is how you become the very best version of yourself. Finding those edges, bumping up against them, being curious about them, examining them, that my friends is growth, personal growth. So those are the six powerful lessons. My favorite one was the last one about finding your edges. But the final takeaway is this. You have nothing to lose. If you're thinking about starting over, if you're feeling the pull, the hunger, the desire, ask yourself this, what do I actually have to lose? Because here's the truth, even it doesn't work out

the way that you want, you still win. Every reinvention I've had, even the ones that didn't go anywhere, taught me something invaluable. They sharpened me, strengthened me. They made me into the person I am today. If it doesn't work, you are not failing. You didn't fail. You're not a failure. You're learning and expanding and growing. And that is never a waste of time.

And it's nothing to be ashamed of or embarrassed about. So if this resonated with you, please drop a comment below. And if you're ready to stop hesitating and start taking action, hit that subscribe button because the secret to success is not in the doing, it's in who you are being while you're doing it. And if you bet on yourself, you win no matter what. See you next time.