.png)
Peer Effect
Best way to scale? Your peers have the answers.
This is the podcast for scaleup founders looking for insightful, actionable wisdom from some of the best operators around. Each week we’ll explore one secret that other founders and experts are using right now and how to implement it.
It’s practical wisdom to build the company AND life you want. Hosted by renowned founder coach and advisor James Johnson.
You’ve survived to £1m, now let’s scale to £10m+.
Peer Effect
Redefining Success & Integrating Work and Life, with Kelly Ryan Bailey
What if work-life balance isn’t the answer?
As founders, the pressure to keep moving forward can feel relentless. But what if the secret to success isn’t sprinting harder, but intentionally slowing down?
In this episode, I sit down with Kelly Ryan Bailey, a serial entrepreneur who’s launched 15 startups, one of which sold for $300m, to explore the power of pausing. Kelly has mastered the art of aligning personal and professional success, turning moments of reflection into a framework for sustainable growth.
Together, we dive into:
- Why aligning personal and business goals is critical for long-term success.
- The role of intentional pauses in preventing burnout and fueling creativity.
- Kelly’s “growing forward” method for reflecting and resetting goals.
- How redefining success can lead to a more authentic, fulfilling life—without sacrificing financial growth.
More from James:
Connect with James on LinkedIn or at peer-effect.com
my brain works in visual, so I tend to think of this like a big puzzle. You know, in front of me and there's a few different pieces. I, you know, mentor other entrepreneurs. I advise everything from early startups to larger businesses. I do consulting work, so there's like all these little pieces to the puzzle. I love the speaking engagements, I love the podcasting, right, like, how do they all fit together? And that's kind of that strange moment that I find myself in right now.
Speaker 2:It feels like if there's this moment of the 15th and there's crossroads, it's probably a good idea to ask the key question, which is like what is one thing that you have seen that you would share with other founders after your journey that they should think about?
Speaker 1:So the one thing well and I think I've learned this the hard way over multiple times Remember, I'm on business 15. And, by the way, just to mention to everyone that it's like, all of my businesses have been very different, everything from like large tech organizations that sold for $300 million to like small food and beverage businesses. So there's a lot in between there, and the one thing that I've seen time and time again is that it actually is really helpful at times to pause or slow down, take a moment to recharge, think through what is the next step. Quite often in startup world we just keep running. You know you're like no, no, no, there's I got to get to that thing, and it is shocking to me how amazing a pause can be for your forward progression.
Speaker 2:When you say pause, what do you mean by that?
Speaker 1:So you know, and I'm so curious to hear from you because you work with a lot of founders as well, so I think it depends. For me it's always been life moments, so something sort of like smacks you a big change and you're you know, a lot of times I've tried to push through that change, as many of us do, and recognize that what came, you know, what came through that change, if I had just taken a moment to reflect on the fact that life is moving in a slightly different direction now, how does what I'm doing fit into that.
Speaker 1:You know, not that I don't think it's good to push through things and learn what's on the other side. I still believe that. But it's just taking that moment to really sit down and think like is, is this exactly what I want to be doing right now? Is the four, the goal that I have in mind at the moment, the right goal for what's going on in life right now? So I say pause because a lot of times we just don't give ourselves that time to reflect when we're running at such a rapid pace. Um, pause can look very different depending on what type of founder you are and what type of scenario you're in. So not all of us are blessed with the opportunity to just like shut down for months at a time, right Like that's just not always an option. So that's why I always say pause. But it's whatever really works well for to have that moment of reflection to think through. You know, am I still headed on the path that I want to be headed on?
Speaker 2:But it was really nice about this. So you're saying it's about sort of taking that moment when life changes to pause and go. Are my business objectives and my personal objectives still aligned? So it's very much about this alignment between business and personal objectives.
Speaker 1:It is for me. I mean, and this is why I was saying I was curious, because you've worked with other founders. You know, being a mother, I find that mothers typically tend to think of others in their life their family, their friends, sometimes before themselves and even as a founder in their life, their family, their friends sometimes before themselves and even as a founder. And so a lot of times you'll get caught up in, you know, something again. That happens in the family context.
Speaker 1:To me, personal and professional, we're always woven together, because that's how I ended up on this professional path. I wanted to find that balance and sometimes what I want right, the goal in my mind, the major goal at the end of the day, was to find the balance. Sometimes that balance was so disrupted that I couldn't see and I, you know, I had to take that moment and say, like gosh, I love what I'm doing, this is fantastic, but it's not allowing me to lead the life that I want to lead. So now, what Do I want to continue with that? Is it that important to me, or do I want to adjust and change that? I mean? I totally agree.
Speaker 2:I think, I think we're taught as founders that it's kind of like it's all about work, personal. You worry about personal when you, when you've exited, and I've really come to believe that actually your work life engine is when it works really well and you integrate it, rather than it's this balance. I think this idea of work life balance, balance, creates this sort of construct of it's really one or the other and it only really works over a long term if you can find a way to integrate it.
Speaker 1:Mm-hmm, and so that's why it's like the founders that you've worked with, just like I described that I kind of once I went into startup world staying, even if it's not their first startup, but staying in that environment.
Speaker 2:Yeah, because I mean, I think for a lot of founders you can look at sort of in two stages kind of got the survival phase, which kind of that zero to one million kind of phase, and I think there are certain behaviors that, while not survivable long term, are necessary in the short term. It's kind of the three rules I talk about, like do more, go faster, self-sacrificeifice. They're almost necessary in that first stage, but then you kick into the scaling phase and those three rules will switch from being kind of the survival engine to work or the burnout engine. It's just gonna you end up being sort of successful, but maybe successful, maybe failing, but if you are successful you're probably broken and if you're broken.
Speaker 2:Potentially your family is outside that because it's general toxicity. So I do think what I found was like how to change those rules and behaviors to kind of shift a bit more into long-term success rather than survival.
Speaker 1:Yep, no, I totally agree with that. I think of those beginning stages almost like technical build, like they're sprints, but in between those sprints right you still have to have moments where you rest, because you can't keep sprinting the entire time or you just won't be able to go.
Speaker 2:Yeah, you can. So acceleration, crash, acceleration, crash, and that crash can be like physical, it can be mental, it can be business, but there is this kind of surge, momentum and stop and actually, if you think about for a long time, you get further just by being a bit steadier. But it's kind of seductive, that kind of like sort of oh my gosh, it's totally seductive.
Speaker 1:It gives you that same adrenaline feeling, right, I, I see it all the time and I just I think that's why and I've done it myself so multiple times and I find myself, you know, skirting that more often.
Speaker 1:You know it's just, it's a hard behavior to to get yourself out of, but it's just those. That's why I kind of bake in these moments where you know you, just you rest, or you know and and I'm, I build out, you know I the sort of it's like an overarching practice, but again, I, I always preface that I'm at a different place, right, some people come into being a founder without having thought through from the beginning, like, oh gosh, I really want to be a founder and I want to work myself to this way. I think you know, for those who might be thinking I would really love to start my own business, those are the kinds of people that I'm like hey, just take a minute to just like vision board or whatever you want to do, out what you want your life to look like, because sometimes you write, you have that, um, you see these, what you see online, which is like this is amazing, you're just going to have this amazing, huge exit. It is not like that.
Speaker 2:Yeah, yeah, I think often it's a lot longer, it's a lot harder work than people realize. Yes, and also I think people are such bad bosses to themselves. It's kind of like you wouldn't accept someone else being the boss to you, you wouldn't be the boss to your team that you are to yourself often.
Speaker 1:Right, yes, that internal voice that you are to yourself often, right, yes, that internal voice that you have with yourself, it's just. Oh well, we all, we, I think we all know we're like the harshest on ourselves, so, um, amplify that well, well, how do, how do you create this pause?
Speaker 2:because I think it sounds it's a really nice thing like there's definitely a value to pausing when you're in the business and like taking stock, but it sounds like there's this potential for your business and personal to drift apart when, like when these life moments. How do you go about making that space? I have someone else listening so they might copy this.
Speaker 1:Yeah well, so the first time that I made this space, it was a physically forced space. So I will clarify that. I hit like major burnout to the point where I could not get out of bed and I had never, as someone who is type A go getter, like all the things that we're describing with those types of founders, where I was just like go, go, go, except that go, go, go happened for you know, a good 10 years at that point and three kids later, and my body just one day gave up. And I can't tell you how strange that felt for your brain to say like okay, I'm getting out of bed, and your body to just be like no, no, I told you to slow it down and you didn't. And now this is where we're at slow it down and you didn't, and now this is where we're at um. And so the first time it was super painful, meaning like everything, like I just was like, oh my gosh, I'm gonna lose everything, like this is the most awful and horrible thing, but also, at the same time, what it taught me was, uh, to rely on a team um, to understand that it's not only ever going to be you, because, like, inevitably, things happen Maybe it's not burnout, maybe it's, you know, a health issue, maybe it's something with one of your family members right, there's a thousand things that can possibly happen that land you stopping your tracks where you don't want to be.
Speaker 1:And after experiencing not burnout multiple times, but moments in life that were forced stops, I started to recognize that, gosh, what if I planned out these stops? Like what if I got ahead of it, as opposed to just like let life happen and then just totally flip me out and turn me upside down? And so I kind of just of all of the self-help books that I read throughout all of these like crisis moments, I kind of developed over time my own practice that seemed to work really well for me and what I was doing. I call it growing forward, and it's just sort of like, again, I work a lot in tech and so in tech, when we're innovating, we say we all want to fail fast and fail forward.
Speaker 1:Right, and I was always like gosh, it just sounds like very negative, and most of us, as we described earlier, have the tendency to be really hard on ourselves and quite negative, and so I was like how can I reframe everything in my life right now to be a positive, and this concept of so it's a practice that I do, and I think that's what makes the difference for me on these pauses, because it's now a practice that happens the it happens on a weekly basis, and so on a weekly basis it looks smaller, right, it's not like a life-stopping I'm in bed, can't get out of bed, moment it but it's a baked in rest period, reflection period, um, and it's something that I do every week and there's slightly longer portions of it that I do every quarter and then at the end of every year, I kind of take maybe like a day or two and really try to like get away from myself and like reframe.
Speaker 1:Okay, am I on the right track?
Speaker 1:Because, like I said, it's just it doesn't have to be that it could be a major life moment that happens, but it but it just could be a natural weight, like you know, veering off of the path that sometimes we do, because in startup world, when you're a founder, you know you just things happen and there's things get exciting and all of a sudden you've said yes to these things and you end up going in a different direction, you know in a slightly different direction that you had anticipated, and so you know that's kind of how I now bake in those pauses, because I've I've really made it a point to myself to know that it's my personal health Again to me personal, professional those lines have been blurred my entire life so I never thought of it as anything different.
Speaker 1:It's an interwoven. My health directly affects how I can perform, and so if I can't be on top of that and be in the place where I can like best perform, people describe themselves as like feeling themselves like a Ferrari right. Whatever it is that you want to, what analogy you want to use for yourself? You have to be at top performance to go out there and do amazing things so how would I say that's on a weekly basis?
Speaker 2:how long is that? Is that check-in versus court? It's kind that two days at the end of the year, you know what.
Speaker 1:Every Friday at my end of day, I will leave an hour to do this practice. So the weekly is pretty short. Now there are times where I've just accomplished so much in like a four-day week that you know, in a shorter period of time I might need a little bit more time to spend on this, because it's like and over time you learn right, like I've learned how I navigate when I know that my brain is just like, oh, like I just really need to like sit down and focus on myself for a minute. But it can be pretty quick, and so I typically go through a again, depending on where the week is. Sometimes I started off with like a quick five to 10 minute meditation. If I'm like super amped up, if I'm feeling a little bit more like, I'll like do a little like personal dance party, like throw my favorite song on, just like dance it out. So it just depends on like what vibe I happen to be in at the moment to start this practice. But whatever it is, to get yourself in the mood you need to be in, and then I just sit down and it's again, it's a practice.
Speaker 1:I'll go through that week, just the one week, and write down all of my accomplishments, big and small, because when you I learned this in burnout, you have to there were like the little things that I had to sort of like pat myself on the back were like today you brushed your teeth. So big and small accomplishments, because when you first start this it's actually really difficult to be like, oh, that was an accomplishment. But like doing something new and different is actually an accomplishment, moving through fear, like there's so many different things that you might not recognize as an accomplishment. But again, I think it's really important to start off with all the big and small and then I write down what I learned that week, because, again, growing forward, that's what I call this. So when you're what you've learned that week, again, sometimes you're relearning it.
Speaker 1:It doesn't mean it's necessarily a brand new learning, but something that you learned that week that was like interesting, potentially helpful. It's not a mistake, it's not a fail, it's actually something really important because when you write down what you learn, it helps you then reflect on what the positive portion of that is to move forward. And I physically still write this down because there's something about putting pen to paper, that action that helps your brain do what it needs to do. And then I write down what I'm grateful for. And again, sometimes this list is like an extremely long list and sometimes this list is like coffee like I effing love coffee you know, it doesn't have to be these like amazing things.
Speaker 1:And then I just remind myself what I chose for that quarter goal. So I'll write them down again, because the more you write down what your goals are, I guarantee the more chance you have of attaining them. So every week I write down those goals again and then I look at what are my priorities for the next week. So I only get three priorities for a week because I've learned that any more than that just you're just setting yourself up to not succeed. So I pick three priorities because I have those goals right in front of me and then I have OK, this is what is moving me towards those goals. That's what I'm going to focus on this week and every week do the same thing.
Speaker 2:I really like this focus on goals. I think often people set their goals for the year with a quarter and forget about them. That feels like a really nice, like sort of weekly opportunity.
Speaker 1:Yep.
Speaker 2:How does that look then quarterly?
Speaker 1:Yeah, so if you actually think of this in the reverse, so when I first started this it was like the annual. Um, you start big right and you bring yourself back down so that annual so think of this as the annual was. Uh, I start off with what do I want my life to look like? Like, if I close my eyes and this is what I want my life to look like, because, you know, a lot of times we kind of forget again what we're working towards and so we get pulled in by the potential of money or fame or what are the things right Like. We just get pulled into those things that we forget, like what is the picture that I am trying to create? And from there I say, okay, what are the goals that are going to get me to that life that I want to lead, that I can focus on this year? And then I start continually breaking that down into quarter, into month, into week. Now your weekly priority is, like I said, when you do that quick weekly thing, those adjust and change, but you're always focused on what the major goal is and I have my big goals written up on a whiteboard here to the left that's in front of my face all the time, so they're always there. So that quarterly is just that next step where I'm like remembering hey, these I'm reflecting now on these are the goals I set for my quarter. Did I attain those goals? How do I? Is there anything that I need to adjust because I didn't get to something? You know, what have you? What adjustments do I need to make based on what I had set out myself for that year?
Speaker 1:Again, if you've had a major life shift three years ago my dad suddenly passed away out of nowhere young man in the whole scheme of things, late 70s or late 60s, so still fairly young and it just threw me for a loop and I had to take that quarter to just spend a little bit more time with myself to say like, okay, is this what I'm working towards anymore? Do I need to change anything? So, again, that's why I say I'm like be kind to yourself, know where you're at in that moment. If something major happened, give yourself a second to absorb that. Think that through. How does that necessarily change? But again, for me, I'm it's.
Speaker 1:I've don't get me wrong. I've been the kind of founder that hasn't done this before, that pushed myself to the ultimate limit and crashed right. So I've I've been there and I know that I want to be in here for the long run, and the lifestyle that I'm trying to build is not that that doesn't throwing myself into crash and burnout all the time is not fun. I don't want to do that anymore, and so now it's just the focus on that life, and sometimes that means I might not want to start. This is a great idea, but I don't want to start that business. But I'd love to help someone else start that business. So it helps you just like think these things through a little bit more.
Speaker 2:And it sounds like these goals are a mix of, like professional and personal.
Speaker 1:Yes, completely. So when I like close my eyes and I think of my life, I mean, how often are we actually I, I might be thinking like gosh, I really want to get like a TEDx, I don't know Right Like like there might be a professional mix in there of what that life looks like? Um, but a lot of times when we close our eyes, like we're thinking of things like I want to travel more, I want to you know we're. We're thinking of things like I want to travel more, I want to you know we're. We're thinking of the life things as opposed to the professional things. But then you start to look like when I first did this, when I had that burnout, I was like my professional life is never going to lead me to the life. At that moment in time it was like it's never going to lead me to this. What the what am I doing with myself?
Speaker 2:so much what you're talking about resonates, just because what one of the reasons I have like we don't really re-examine what success means to us from a very early age. Some of those are so built in by the time of kind of 18. So it's almost the last time we have to really think about it Once again. The workforce was so busy like charging off targets and actually when you stop and go, what do I actually I actually want? Often it's not what our teenage self thought was impressive. It's very radically changed and that sense of like this is not going to take me to where I want to be is quite a. It's quite powerful and often I think that's the dissonance. Before we look at it, there's this, we feel it inside us going. We know it's not taking us there, but we don't really have the time to explore it and often then we kind of mask it by trying to distract ourselves by working harder, partying harder.
Speaker 1:Do whatever, yeah, all the things that can distract you from the actual thing, which is why that I was doing those things too, and it's like, if you don't, if I didn't make this a part of my everyday, like my every week, my every moment, everything that I live and breathe, then it's so easy to fall back in to everything else, for whatever reason, and that societal idea that we have in our head when we're young man. That is hard to break. I don't know exactly why, but especially for women, because there's this added pressure of who you're supposed to be as a wife, a mother, what your home is supposed to look like. And when I first wrote that list for myself, guess what? I actually don't care.
Speaker 1:If you come over and my house is not clean and why is that my fault, by the way? Like why am I the one who's all of a sudden, you know, in trouble for not keeping their house clean? Like, no, I don't want to subscribe to that thought process anymore. I actually would love one day if I got to the point where I had someone taking care of the house and making it look that way. That'd be fantastic, but nope, I don't want to do it like and so I would spend like hours a day just being ready for Martha Stewart to pop over at any moment. I mean, it was ridiculous. I was sleeping like four hours a night because everyone else would go to bed and I'd be like scrubbing the house and I'm like what am I doing? Why?
Speaker 2:it feels like this this is, this has come out of sort of personal pain, this, this, this revelation. But would you say that, having had this revelation that personal and business are needs to be interlinked, the success needs to be locked? Do you think that's actually led to greater business success?
Speaker 1:Yes, yeah. But it's so much easier when you know your set of values. Your set of values and that's part of the annual practice is like revisiting your values for yourself, what that mission is for you in life. Um, it's so much easier to make a decision, like, again, what every founder will find themselves in, that moment where, all of a sudden, things start to take off right and it's like super exciting. And you you're like yes, yes to everything. Right, you're not sitting there thinking you know, does this fit with what I'm trying to do? Because you're just so excited that you got to that point and you just want to keep going and get the recognition and get all the pats on the back right. But it's so much easier when you have this set of values that you're, and again, thinking of this as a marathon as opposed to a constant sprint. It lets you look at things differently.
Speaker 1:I was traveling at the time of that burnout. I was likely working. I had a baby that my third was under one. I was working probably 80 hours a week, traveling three days a week, and when I was like sitting down to reflect on this, I was like gosh, I was. I love traveling, don't get me wrong, but I definitely was like. That wasn't for me, that was not enjoyable. You know I was like it may have had moments of success, but like it, just I was not enjoyable. You know I was like it. It may have had moments of success, but like it, just I was not the person I wanted to be. And as soon as that year I mean this for me was a year process I had a lot of health issues. It's a bigger thing than just the burnout. But um, when I came back, having that grounded foundation to build upon oof, anything is possible then I think that is we get caught up in these battles.
Speaker 2:If I go faster, I'll get there quicker. It's actually you might just travel a lot further, but you're not necessarily going to go directly point A to B, and I really do feel this. Aligning your personal professional leads to greater success, not less success, which is what's a work-life balance, would sort of tell you as a construct.
Speaker 1:But also success. I should say and you're likely thinking this, but I think we should call this out for our fellow founders Success is you choose. What success is? So, pre-burnout, what I considered success was my title, my status, the amount of money I was making, the cars I was driving, the house I was living in, the clothes I was wearing, right, Like. Those were the things that I subscribed to as my definition of success and in part of this process, and again what I do every year, I am reframing success. So for those of you who are wondering, no, I'm not less financially successful, surprisingly, but I actually care less about it, and I will actually say no to things that may lead to more financial success, because it would skew the comfort and life that I've chosen to lead and my set of values. And having that, your new version of success, again, that for those values, whatever it is that you're moving towards. That is why I say, oh, yes, I'm more successful based on my version of success as opposed to anyone else's.
