Ep #157: Curing the CEO Bottleneck with Karen Sergeant

The Design You Podcast with Tobi Fairley | Curing the CEO Bottleneck with Karen Sergeant

Bottleneck behaviors were once habits of success, but they can be problematic for you as the CEO of your business. It is no longer doing more that will get you to where you want to go, and by acknowledging your habits, you can cure the bottleneck you’re creating. Today’s guest joins me to explore this further.

Karen Sergeant is my COO, and the creator of BottleneckRx, a six-week program that helps CEOs remove themselves as the bottleneck in their growing business. She helps digital CEOs with operational planning to support six and seven-figure launches and businesses, and joins me today to discuss the importance of embracing uncertainty, how to get out of your own way in life, and to share what she’s learned from the first and second half of life.

Join us this week as we discuss how to work through the bottleneck issue in your business and why bottlenecks, boundaries, and ultimately happiness, are an inside job. Karen shares some second half of life wisdom and why it’s important to start listening to your intuition because it’s turning inwards that’s the answer. If you’re looking for more meaning in your life, friends, this episode could create some opportunity for you to explore that further!

If you want help creating a business with thriving revenue streams so that you can design the life you really want this year, now is your chance! We’re going to be opening the doors to the Design You Coaching Program really soon, get on our waitlist now!

What You'll Learn From This Episode

  • How bottlenecks form in business.
  • What it means to have a first and second half of life.
  • How to develop best practices to help you and your team.
  • The importance of embracing uncertainty.
  • Why as small business owners, we can create the world we want to see.
  • The issue with hustle culture.

Full Episode Transcript

You are listening to the Design You podcast with Tobi Fairley, episode number 157.

Welcome to the Design You podcast. A show where interior designers and creatives learn to say no to busy and say yes to more health, wealth and joy. Here’s your host, Tobi Fairley.

Hey friends, I have a really interesting conversation for you today. I didn’t even say hello first, did I? Hello. But I am so into this conversation, really this – I don’t know – way of living that I’m going to talk about today on this podcast with my COO or integrator as we sometimes call her, Karen Sergeant. So Karen, you’ll hear about her story.

She’s done amazing things, everything from being in the CIA and working in counterterrorism, to working in Silicon Valley, to now helping small entrepreneurs, small businesses. And helping people really do the operations piece and get rid of bottlenecks and issues in their business.

But so much of what we talk about in today’s conversation is a much bigger story. It’s what she refers to and I completely know what she means by this term, the second half of life. It comes from her learning and studying under Richard Rohr, a teacher that we both follow and really connect with and relate to. And it’s this whole conversation about sort of what happens when you stop the hustle, and the drive, and the pushing, and the forcing in life that so often happens mostly in sort of that first half of life.

And so we get into this conversation today. And it is honestly something that I think about more often than not. It’s a practice that I’m creating in my life that is anti hustle, anti productivity, do less, do nothing, learn how to be contemplative, learn how to surrender. It’s a lot of really hard things that come with I think hitting that point in your life where the hustle, and the certainty, and the drive, and the masculine energy, and all the things that so many of us have experienced in work and in culture, just aren’t doing it for us anymore.

And we’re learning as Karen says in this interview that efforting is not the solution to burnout, it’s not just doing more that’s going to get us to where we want to go. So that’s so much of what we talk about today. And ironically or not, it may seem ironic but I think these two things are so related. The work she does with entrepreneurs and helping them really understand their businesses, and how they want to show up, and our mindset, and how to get out of the way.

And really this work we’re talking about doing on ourselves, this deep level of surrender that so many of us are moving into possibly because of what we’ve experienced in the last 12 months or so of living in the pandemic and everything else that’s been happening in the world. So I hope you like this episode as much as I do.

At the very least I hope it piques your interest to turn inward, to ask yourself some serious questions, to see if you’re still on that hustle energy kind of treadmill of the first half of life. And if you’re ready to exit, to get off, if that is true for you I think you may find some information in this episode that can really help you move into this next phase of your life. Whether it’s truly the second half or you’re an overachiever and you’re starting sooner than maybe Karen and I did, or it’s later for you. There is no right time for this work to happen.

But if you’re experiencing a desire for that softer kind of existence and maybe more meaning in your life, I think that this episode could create some – I don’t know – opportunity for you to explore that more. Okay, so here’s my episode with Karen Sergeant.

Tobi: Hey Karen, welcome to the Design You podcast. I’m super excited about our conversation today.

Karen: Thank you for having me.

Tobi: Yeah. So people might have heard me mention you before that you work with me in the capacity of a fractional COO or integrator. You’ve been helping me design our ops of our business now for what, 15 or 16 months? So you’re like the go to person to architect anything we want to happen in our business. But you don’t just work for me, and that’s not the only story of your life. There is so much that happened prior to this what you now call your dream job.

So why don’t you tell everybody in your words, who you are, kind of what led you to here. And then we’re going to get into some really probably deep conversation that I’m looking forward to.

Karen: So I help online businesses with operational planning that supports their – it’s usually six or seven figure businesses. Sometimes I’m embedded on their teams as a COO like I do for you. And sometimes I sit outside their team and I’m just an advisor. And I’m really in the third chapter of my career arc.

The first one was actually in, I was in software product management in Silicon Valley during the 1990s which was sort of pre internet but it was during the dot-com boom. It was when it was just coming, and the talent and the caliber of the people and how quickly we moved, I was just a sponge and I learned so much from some really, really smart people.

And once the boom fizzled out then I returned to what sparked my interest actually in graduate school which was counterterrorism and I worked for eight years in the Counterterrorism Center at the CIA. And I worked the Afghan war, so I was frequently in and out of war zones, leading teams and juggling projects. And that led to a gigantic burnout.

And I left my job, and I sold my house, and I moved to the ocean, and I kept looking at the ceiling going I don’t want to walk into a building at eight and walk out at five. And that was when the gig economy was just starting and I was like, “Well, I’ll do that.” And I just realized that I had some transferable skills mostly around leading teams and leading projects.

And I found that I was kind of the missing puzzle piece to the visionary folks who were very product focused and very sales and marketing focused. But when they achieved that initial success and now they have a team and now they need some processes, and they need to not ad hoc it. That’s when they had a gap on their team and that’s what I stepped in and filled. So I’ve been doing that for seven or eight years now. And it really does fit me well. This is stuff I like to wake-up and do. So in that regard it’s a very, very good fit and I’m very happy.

Tobi: Awesome. So tell me a little bit, I’ve heard you say so many times kind of that description of working for the CIA and being in the war. But wasn’t it kind of like ops for the military and the people that were on the ground? What was that role, what did you do for them?

Karen: It was operations. It was not for the military. My remit was to find Al Qaida senior leadership wherever they would be, which mostly had me in Afghanistan and Pakistan trying to find…

Tobi: Wow, interesting.

Karen: Yeah. So using all sorts of intelligence to literally figure out where they were, like what door to knock on to go find them.

Tobi: Wow. Okay, that’s crazy. So I can see – wow, talk about pressure. I can’t even imagine. Literally, sometimes we feel like we’re in war zones in our own lives, in our own businesses. But literally the difference of burnout from an actual war zone and counterterrorism is unimaginable to me, fascinating. But as you now know with the people you work with, burnout, is burnout, is burnout no matter the source of the burnout.

And a lot of what you help do is create systems and operations that keep people from that burnout, of being on the treadmill all the time and being bottlenecks in their businesses.

Karen: That’s a really good way of putting it, yes. I hadn’t really connected those dots but yes. We all crave the – of staying in whatever our zone of genius is, that’s where we want to be and that’s where our batteries either get drained the least or they get filled up. And so you do need to find a solution because when you’re a small, you know, when you’re the CEO of a growing business as you would know, all sorts of things need to get done. It’s not just your little niche that needs to get done. So you need to find solutions for the whole thing.

Tobi: Yeah, interesting. So you have created a framework, a three part framework that you use. And I mean for me you don’t really tell me you’re putting me through the framework. You just put me through the framework, but for other people, but you’re kind of that advisor or consultant, you actually use this framework. So tell us about that because what I think is interesting is – and you and I have talked about this a lot.

I think people like me who are visionaries and who get really fatigued by being in the weeds of operations, we think that it’s just about the how, just give me the steps and that’ll fix it. And it’s about so much more than that and the bulk of the problem often is the visionary. And when I brought you on I’m like, “I want you to teach me how to be a good visionary. I want you to teach me how to be a good leader.” And there’s so many times that you’re like, “Tobi, you’re doing it again. You’re doing my job again.”

And I’m like, “Right, and why? Because it’s horrible and I hate what I’m doing, and why am I trying to hire people or I try to fix something?” But you’ve organized this in a way that you help people see kind of those different kind of hotspots and how they can stop being the bottleneck. So can you tell us about that framework and tell us about kind of what you’ve learned from working with people like me?

Karen: Sure. Well, let’s start at the beginning, how did we get here in the first place? So how did bottlenecks forms? And sometimes CEOs will think that it’s somehow like it’s a character flaw of them. And it’s not. It’s a phase of business. And here is the thing, that the habits of success in a very early startup, which I call the MacGyver habits. That’s the touch everything, do anything, customize it, jerry rig it, eleventh hour it, get it out the door. That is how you find your initial success. And it’s usually you, or you plus one getting it all done.

So that’s what you’ve learnt. And now all of a sudden you have extra helping hands but you don’t know how to spit out, like how do I get those other people? How do I get it out of my brain and into their brain? So that’s the conundrum so it’s really just – it’s growing pains. And I find that if we attack it in three ways, this is the full care as I call it. So the first is that mental game, it’s the mindset piece that you almost have to be willing to not be the bottleneck I guess. You have to fall out of love with your fire drills.

I’ll tell you what; I pry fire drills from cold dead hands. That is the last thing they want to give up because it’s fun. And it is how you’ve – it feels good, it kind of is like let’s go on the moon.

Tobi: Yes, well, good and bad though. And it’s exhilarating because it makes you feel important, like you’re solving this urgent problem. But the hangover of the fire drill feels horrible.

Karen: Yes. And then also if you see a failed attempt, I say that it’s – this isn’t my quote but it’s not about ideas, it’s about making ideas happen. So an eleventh hour idea that’s poorly executed isn’t any good at all. But an okay idea that’s very well executed, that could be a great customer experience. And so visionaries are all about the ideas and they think the idea is trump, the idea is king. If I have the best idea I win. And I say you have to implement the best idea wins.

Tobi: I agree, yeah.

Karen: So at some point you have to stop ideating, you have to stop. And you have to sort of decide that this is what I’m going to go put in the world right now and I can iterate later. But we have to, you know, you sort of have to call it. You have to put a lid on it and you have to go implement at some point. Those are not visionary. Visionaries and creatives don’t tend to want to do that because that’s just not how they are in the world.

Tobi: It doesn’t feel fun. You’re like wait, the thing I love the most you’re going to tell me I can’t do right now. Yeah, it creates that kind of a tantrum. It creates resistance. It feels almost like a negative energy sometimes until you learn the why behind this. And what it looks like to – I call it putting a governor on me or you’re like, you know, we have to handle Tobi. Tobi’s being handled and she doesn’t like it. But that’s kind of a necessary evil of getting this thing to market before we can let her run wild again with her ideas, right?

Karen: Yeah, it tends to be a bit of a bummer for folks to be like, “Well, I guess I’ll take this okay idea and run with it.” But that’s just – I mean if you think about the full organization has to get behind you and implement and get something out. So there does need to be, at some point you do have to call it, you have to call the game and you’re like that’s where the goalposts are, let’s all run towards it. But I promise I won’t move it anymore.

Tobi: Yeah, that is the definition of bottleneck is the visionary who keeps moving the goalpost, right before you kick the ball, your foot flies out from under you and the goalpost is back 10 yards. You’re like, “What happened?”

Karen: That’s exactly it.

Tobi: That’s so funny. That’s a good visual.

Karen: So that’s the first piece is handling the mental game and handling your mental approach to this. And then the second is behavioral triggers. And this is also something that’s – I’m not sure if there’s anyone out there sort of trying to tackle this problem this way. But I think this is akin to stopping smoking or going to the gym three times a week. That’s not a knowledge problem. I’m not going to ship you more knowledge and suddenly you’re like, “You’re right, I will stop smoking.”

What we have to do is figure out why do you light up? What gets that cigarette in your mouth and you’re flicking the lighter? So I look at it from – I call it the swooper tracker actually sometimes with clients. And we try to analyze why are you swooping right now? And swooping has a number of definitions, and it’s not always swooping. Sometimes it’s changing the goalpost. But what is it about right now, what is happening with you that makes you want to go tinker?

Because we do have to identify those patterns and we have to sidestep them because I can ship you every template in the book. I can give you new best practices. But if you’re not willing, if we can’t sidestep your tendencies they will actually win in the moment. Because you’ll go, “Just this once, I know that I’m not supposed to tinker but I’m going to tinker this once.”

Tobi: Yes. And just for anybody who’s listening who’s not really knowing exactly what you mean. What I call it is wonder woman syndrome or superwoman syndrome where I’m like, “Okay, I’m going to get all these people, I’m going to get them out of the way.” And then I see somebody doing something slightly different than I would want to or it feels uncomfortable to let people run with things. And my brain starts being like, “But it’d just be better if I do it or it’d just be faster if I do it.”

And the next thing you know I’ve swooped in and taken the job that I had already given to someone away, or I start messing with it. Or if I’m fiddling with it in the background and then they bring me the work they’ve done. And I’m like, “Yeah, I forgot to tell you, I’ve already changed, we’re not doing that anymore”, or whatever that looks like. Some version of that kind of visionary getting in the way and mucking stuff up and as you call it, tinkering with things is what we’re talking about, yeah.

Karen: A 100%. And sometimes we can get at those. So one of the ways is you just keep a log. Another way is you can sort of look at the Myers Briggs or the Kolbes or whatever you think defines you. And you can find where do you feel safe and where do you start to feel vulnerable. So if you were a high fact finder let’s say in Kolbe, it feels safer when you’re digging in to all the details. It feels risky to delegate that to me and to think that I am going to do as good a job.

Tobi: I think that is what my – I think I am fairly high on that. I resonate with what you just said for sure.

Karen: So right there but what we want to say is, instead of putting yourself in high fact finder jail which means every detail has to run through you. We’ll move at the speed of you. Sometimes even just articulating that way, it feels risky to delegate this to somebody else. But suddenly there is daylight that kind of opens up and then you can almost work with that tendency. So there is ways of, if you’re aware that this is just sort of like thin ice for you and we’re aware, there’s ways that we can kind of come together and still manage that, that sort of near occasion of swoop.

But we can get past it because it’s a habit, it’s a muscle that you can just exercise and you can get past it.

Tobi: Yeah, so interesting.

Karen: So that’s the behavioral triggers. And then all of that effort sort of leads into the best practices. The industry best practices are out there. We all probably know them. You can Google them. They’re really not that secret. But the point is the effort that we just did in the mental game and the behavioral we tweak. So we need to sidestep your tendencies. We need a best practice that’s actually going to help you out, not me out, not a different CEO out, we need to help you out.

And so taking those best practices and just sort of tinkering and making sure that they fit really good for you and the people that you have on your team and then you’re off and running. So now you have a new op, instead of MacGyvering, you have a new, I guess, operating system. And you get to go off and conquer the world and do all the things that you had wanted to do because now you have a sled team. Instead of the dog walker with the 15 dogs all going in different directions, you’re a sled team and you’re just off and running.

Tobi: Yeah, that’s so good. And I think what’s interesting about that, what you just said about best practices is I think a lot of people want to take things at face value and think well, this person I admire, so is doing exactly this way. And then they think something is wrong with them if they’re not able to do it. And that’s like with any, you know, the diet or anything else. You’re like, “Well, that didn’t work for me, or that failed.” And I think it’s because people aren’t willing to customize it like you’re saying. And I love that you, you’re very clear about that.

Yeah, we can look at best practices but if you’re not going to follow through, if you’re not going to be disciplined, if you’re going to swoop in every time we do, this is clearly not the best practice for your company is what you’re saying.

Karen: Exactly so, exactly. And then it’s not a solution, it’s just a thing, it’s just an SOP that’s out there or a template that’s out there that works for somebody but not for you.

Tobi: Yeah. And how many businesses, which are tons of them that have tons and tons of SOPs that they just aren’t using or that they keep fighting against or keep ignoring. I was just talking to another coach that I just hired, you of course know about Lauren that’s going to be on the podcast somewhere around this episode as well. And we were talking about SOPs this week and how we have an obsession as humans with getting all the ducks in a row and all the SOPs or processes done. And we’re always hearing ourselves say, “Systems, it’s a system, we need a system.”

And she was saying, “But systems can actually become too rigid and they can be counterproductive.” And we were talking about, “What would it look like in the business to have just the least amount of systems you need to operate effectively but no more than that?” And I think that’s interesting because even as a visionary, I can get obsessed with checking all the boxes. And do we have, like once we start systemizing. Let’s get everything systemized.” And so even that idea of only having as many as you need feels kind of vulnerable to me.

How do we know we have the right ones? And I don’t know. It’s just a fascinating concept. Do you encounter that with the people you’re working with too?

Karen: Yes. There seems to be a fetish about SOPs. And actually the more visionary you are the more messy, creative you are, the more you think that SOPs – I just think of it as a well organized closet with all of the labels and everything is perfect. But come back five days later and it’s a mess because you can’t keep it that. It’s just not workable. It’s beautiful and it makes you – it actually…

Tobi: Well accomplished or something.

Karen: Yeah. Aesthetically it’s beautiful to have this filing cabinet full of everything we do in this company is laid out, except that it’s not real life. And it’s not as helpful as you might think it is.

Tobi: Yes, that’s a beautiful description of it. And that’s exactly right. And that’s so true for creatives like me because we do. I mean I consider myself a very organized person but what that looks like is get everything cleaned up, and then have a crazy week and it looks like a train wreck and then I clean it back up again. And so I do love that there’s a place for things to go. But I would be lying if I pretended if you stopped by on any random day there wouldn’t be food on the counter and beds unmade and whatever. I mean that’s happening today in my house.

And so yeah, that’s a great description of understanding yeah we need a basket for everybody’s shoes to throw in when we leave them all over the house. But are we going to still see shoes over the house during the middle of the week? Absolutely. And I think that that’s true for a business too, we’re going to have some systems. But I even heard Amy Porterfield say this on a podcast today. She’s like, “Yeah, for me to pretend my business runs like clockwork and there are not days that we’re a total hot mess would be a complete lie because everybody has that.”

So it’s part of just accepting that that’s kind of what doing business looks like, right?

Karen: I agree. And it’s, you know, was it Eisenhower who said, “It’s planning, not the plan.” The plan isn’t important. It’s the planning process that you just sort of illustrated that with your cleaning up once a week. So there is a place for everything to go and you do know where something belongs and that’s your central reference point. But then you also just get to get messy and you get to just deal with life.

Tobi: Yeah, that’s so good. I love that your job is to get everything organized and working smoothly. And then part of what you’re teaching is but don’t panic because it’s still going to look like you’re doing business. It’s still going to look like a train wreck at times and it’s supposed to.

Karen: Yeah. It’s real life. So I am actually not pro SOP in that way. I am minimal at best. And I also want it to hit the right things and not hit the other things. A great book, I don’t know if you’ve read it, Checklist Manifesto.

Tobi: I haven’t.

Karen: It was actually 10 years or so again, Atul Gawandi. And it’s the perfect middle ground between taking the creative; in this case it was surgeons and surgeries. And how do you checklist a surgery? You can’t. You can’t paint by numbers a surgery. But there are certain things that you stop and you’d make sure that these five things got done and the infection rate, and the death rate, and everything else just sorts itself out. That’s the kind of SOP I want. I want the thing that you pause and you make sure these five things are in order, good, go on. Go run your business.

Tobi: That’s awesome, I love that. Okay, so I think that leads us a little bit into this other what you and I were both like, “Yeah, let’s talk about the business part”, which is a necessary evil or a necessary, maybe not evil. And then let’s talk about what really lights us up these days. But I think they’re very related actually.

Because a lot of what you’re dealing with, I mean the mindset piece, the hustle piece, even the living with the uncertainty and allowing things to be uncertain. They all play into this kind of bigger conversation that you and I have a lot which is what you call, and I know why, because we’re both kind of followers of Richard Rohr and his spiritual teachings. But what he calls and you ultimately call the second half of life stuff.

Let’s talk about that and what that even means, because I think that actually plays a role if you’re at that phase of your life, and how you’re thinking about the very things we’ve been talking about. How you’re thinking about your business, how you’re thinking about how you want to show up in it every day, how you want to feel, what’s important to you anymore, and talk to me about that. Where’s your head when we say, “Let’s talk about second half of life stuff”, what comes to mind?

Karen: Yeah. So the second half of life happened to me, this wasn’t anything I wished on myself. But I was a very capable girl. I was doing a lot of really cool stuff. And I’m actually very glad for it. I’m very glad I had the first half of life. But my career, that burnout was real. I had to break up with my dream career because of my health issues and the fact that I wasn’t sleeping at night. And then I had a relationship go sour. And then all of these just my anchors, and if I’m not that what am I? If I’m not the counterterrorism expert what am I?

Tobi: Absolutely, yeah, identity, yes.

Karen: I don’t know how to define myself. I don’t know how to say what I do. I don’t know what to say. I’m adrift and feeling adrift is not what this girl was made for, I’ll tell you that. That is an uncomfortable feeling. And then I just expected the next career to come along and it didn’t. And even though I say that I, you know, I’m a kind of born COO, it really feels natural and good for me to do that. It’s not a replacement. It wasn’t like out with the old, in with the new. There was a decade or so of ambiguity, high ambiguity. And then I just don’t step into that role like I did my earlier role.

Tobi: Yeah. For me I can relate so much in that. I think it can happen with something that feels catastrophic like you’re talking about with burnout. And I definitely hit burnout in my own career. But I think it also can, like the flipside of that coin to me is also that you checked all the boxes of all the things you wanted to accomplish in your life.

I remember hearing one time Tony Robbins say that when he coaches people like Andre Agassi, the reason that he was the best in the world and then went into a five year slump is because he had only envisioned being the best in the world and then what comes after that. And I can relate to that so much and I’m reminded of that by what you’re saying is that maybe it happens to everybody at maybe kind of midlife or it depends on how driven you are and how fast you move and how many checkmarks you collected along the way.

But there is a point I think for a lot of us where we’re right where you were talking about. Who am I now? And what does this mean now? And we’re kind of embarrassed to say, “Maybe I don’t love what I’m doing anymore. And I thought that’s who I was.” And if, like you said, if I’m not that, and sometimes for people it’s like their kids grow up. Sometimes it’s just like your career’s kind of run its course for some reason or another and you just – I remembered thinking the same thing. Who am I if I’m over my career or my business in the iteration I thought was going to take me to end of life?

And now I’m at mid point and I’m like this doesn’t light me up anymore, right?

Karen: A 100%. And it’s tough even to work for folks who are still in the first half of life. So a lot of times the COO is the chief firefighter. And let’s just not set fires. What are we doing, what are you chasing? What are you chasing? Why does it have to be this hard?

Tobi: Yeah, because a lot of those fires are totally ego driven and feast based and completely manufactured based on this, whether it’s patriarchal, or cultural, or you and I also talk a lot about male energy versus female energy. But a lot of that fire is fabricated by our own minds in relation to what we believe to be successful, or worthy, or the in crowd, or good enough, or some marker we’ve been measuring ourself against. And then you get to a point in your life where none of that matters anymore.

And it’s like you put on goggles and you can suddenly see that all of that was optional. It had a purpose and I’m with you, I’m glad I went through all that drive and all the stuff in first half of life, although it was painful at times. But you get to the point where you put the goggles on and you look at it and you’re like, I can literally just opt out of all of that if I want to without any effort. I can just decide to not care about that stuff anymore, which feels so foreign. I’m sure when you’re watching that happen and you’re like, “I wish I could just tell them these fires are truly all optional.”

Karen: Yes. Exactly what you said, you described it so well.

Tobi: Yeah, so interesting. Okay, so where do you find yourself then, what’s coming true for you with this sort of – because you and I have talked about how we both are in a similar place of moving to a softer version of us. And I think, I mean not to be offensive to you, but definitely for myself I can see that both of us could definitely have had a very hard version of us in our first half of life. We’re powerful. We both have plenty of male energy, drive.

We can hold our own with anybody. And obviously you did in the CIA or in a boardroom or anything else. And that feels so foreign to start to get in touch with whether we call it feminine or just softer. We don’t even know how to, neither of us even really know how to put a label on this. We’re both like that, “Well, I don’t know, just this existence we have now.” But can you speak to that a little bit? What’s your experience been of finding yourself in that place?

Karen: Well, I call it surrender school and I don’t go there. But you’ll probably have to go there. But I mean so what you just said, I’m very capable. I am used to putting effort in the world and seeing success reflected back to me. But guess what? You can’t effort your way into a full night’s sleep, you actually can’t. You can’t effort your way into saving a relationship which is not going to be saved. And so here I am and the world is reflecting back to me and I put more and more effort in. And I try all these things and it’s not working.

And that was a bottom that reshaped my life, I’m so glad for it. But bottoms are bottoms and they’re terrible. But what I realized was that efforting was not where it was at. So I kept thinking that I needed to try harder, or be smarter, work smarter and harder or whatever, and stop. Stop efforting, it’s not effort that gets you there is the lesson. I don’t want to say it in the past tense. That’s what second half of life means to me and I’m still at school.

Tobi: Yeah, that’s so interesting. And in relation to the work you do with people which seems like it would just be about efforting like the ops piece of a business. And yet you’re personally experiencing this paradigm shift to no efforting. And then also we were talking previously before we started about how kind of 2020 was the great bottom out for everyone. Like you said you have to hit the bottom when it comes to recovery kind of concepts or whatever. You were in the 12 step program, whatever. But 2020 was kind of the bottom for everybody. And it was the great teacher that effort.

Effort didn’t do anything. We were all on the same page. We were all completely not in control of our destinies, whether it’s the pandemic, or the election, or the social justice and racial issues that were happening. Effort didn’t get you anywhere. And there was so much uncertainty which felt really miserable because we couldn’t. Usually don’t you think we try to meet uncertainty with effort as the solution?

And when we then couldn’t effort and we couldn’t leave our houses, it was this perfect storm of uncertainty and not being able to solve our problems that I think changed all of us at our core.

Karen: It is changing all of us, it’s changing so much. Yeah, it doesn’t feel pleasant to be adrift. And I wonder if that’s one of the reasons that the conspiracy and some of the other stuff, it is a quest for certainty. They’re not trying to be crackpots. They just need to feel certain about something.

Tobi: I think you’re right, yes.

Karen: Because it’s so painful to be uncertain.

Tobi: I haven’t really thought of that but that’s so interesting. You and I both have talked about the fact that I just read Brian McLaren’s latest book called Faith after Doubt. And he specifically in that book talks about in lieu of a religious foundation that you can really feel comfort or certain in and so many people are shifting from certainty in their religion because it was bumping up against things like racial injustice and social justice things.

And so if you can no longer kind of believe in religion anymore, and we’ve seen people moving away from it, he specifically talks about how he thinks that’s going to – has and will continue to increase things like conspiracy theories and Neo-Nazis, I mean all these other identities and groups because people need to feel belonging and they need to feel certain about a list of rules and beliefs like you’re talking about.

But I hadn’t really thought of that in that exact scenario of saying, “Of course in uncertainty if you can believe, well, QAnon says all these things are the truth.” Then you can get behind that. That’s so fascinating. But the brain will look for it anywhere, even in places that to the rest of us seem like crazy and so – we’re like, “How could this person get behind this concept or this belief system?” I could see that that’s the very reason why. That’s so interesting.

Karen: I think so.

Tobi: Yeah, so interesting. So let’s talk a little bit more about this efforting thing because I was sharing with you that even now saying that what I do in helping businesses be more productive feels really out of alignment to me now. Just saying those words doesn’t feel true anymore. I’m like no, I want to help people have impact or create impact in the world. But I no longer believe that that’s how much we do between the time we wake-up in the morning and the time we go to bed at night at all.

And that this whole concept of efforting which goes right along with productivity to me is part of the problem, the hustle culture. That all is first half of life kind of thinking for sure. But when we find ourselves we’re like, “Okay, we agree that it’s not efforting and it’s not productivity, and it’s embracing uncertainty.” Yet how do you move forward? If you’re not supposed to effort and you’re not supposed to do anything, are we all going to just be like in criss-cross applesauce, like meditation for the next 40 years?

What does it look like to have a life that is softer and not about effort? And it’s so I mean inherent in the idea that it’s uncertain but our brain still always searches for some type of way to organize our life, or our days, or our to do’s. So what have you found that helps you move forward in this new kind of way?

Karen: Yeah. So I think it’s a both and because I think that the paradox that you were setting up is indeed a paradox. So one of the things I think about is that I’m so glad that I’m a small business owner and I work with other entrepreneurs, small business owners because I really feel like we have the chance to shape things to our liking. We can create the world we want to see, the inclusivity, the dismantling. We can have things other than the bottom line be what our business and what our daily effort is about. So thank God because that’s wide latitude.

We also have to pay our bills and we have to make, you know, we have to sell things for money that people will give to us. So there’s the machinery of commerce needs to happen as well. And I think you balance them. I mean I don’t think there’s any – I think you lurch too far one way and then you lurch too far the other way and somehow you’re lurching ahead and hopefully you’re calming more crises than you create and creating a better world at the end of it. But I don’t think there’s any magic formula at least I know I haven’t heard one.

But I think there is a tension between the two and you just sort of sit between both of them and you add some.

Tobi: I find myself defining myself more right now by what I’m not than what I am, which is interesting. It’s like antiracist, anti hustle, anti diet culture, anti establishment, business practices, anti hustle as my CMO Wendy calls it, anti Maserati marketing. And it’s like okay I’m not all of these things. I’m not forcing anymore, I’m not driving hard in productivity. And it’s so interesting.

Karen: Yeah, but we don’t have the words because they made up the words. They made up the vocabulary and all we can do is say, “I want to opt out.” So all we have is the anti this and the none that.

Tobi: Yes, it’s so interesting.

Karen: Yeah. I can’t wait till we have our own vocabulary for things.

Tobi: Yes. There’s no vernacular for the opposite of all of the things, the patriarchy, all of it. When we say those words we know exactly what it is and we’re certain that we don’t align with that anymore. But I think that you’re right. It’s like we’re on the cusp of actually writing the story, and the rules, and the language right now, which is both exciting and terrifying that we can play such a role in it, but that we also have – to me it feels like a responsibility to help define what this kind of new paradigm shift could look like.

Karen: I think so. I think that’s exactly right. I mean I think that’s what makes the dominant culture dominant is that it made up the words and it made up the concepts. And then I think the first phase is reacting to the dominant culture and say, “I’m not that. That’s what I’m not.” And then we have to, you know, maybe it’s another phase where we have to say, “This is what we are. And this is how we harmonize things.” How we can have commerce, and inclusivity, and impact, and all of those things.

Tobi: Right, yeah. Even that conversation which is one that I’m just digging into right now is how can capitalism coexist with antiracism, anti, all the other things that we’re not believing in. Yet we do believe in business and we do believe in value and making money. And where do those meet? Yeah, there’s so much deep, deep conversation I’m working on. Of course I geek out on it, I know that you do too.

Another thing that’s coming to mind, so I know you’ve been doing some work for probably what you’re at least a year into the actual program of doing some work with Richard Rohr in his Center for Contemplation which I really hope is in my future at some point. But one of the things that’s coming up for me when I think about these paradigm shifts is – and we’ve never discussed this, I’m just throwing out to see what you think is there almost feels like a wild west of things that could go awry, not with Richard, I love his thinking.

But with some of the spiritual teachers and some of the people that make money in spirituality. And we’ve seen some of those people that are on the fringe of some of the conspiracy theory things. And I saw some stuff this week in Clubhouse which is such a new hot platform. But people are like, “These people are charlatans and they’re taking advantage of people, and making all this money, and these online businesses.” Is anything coming up for you in that realm?

Because I even hear people use terms like 5D consciousness or whatever, which is a very woo woo term. And I get what they mean and I even agree with some of those people on some of these paradigm shifts. But I find myself almost being fearful of some of those words or concepts because I don’t necessarily trust that they have everybody’s best interest at heart. So that’s why I do turn to somebody like Richard or someone who’s more rooted in a tradition. He comes from some religious traditions.

But have you experienced any of this what I’m talking about of kind of who do you trust, where do you go next, especially with the realm of spirituality when it comes to these issues?

Karen: I have a beautiful, I guess, set of mentors that came from The Living School of the Center for Action and Contemplation. So I feel like my cutting edge is right there and is being well handled. And I do think that they’re rooted in – well, you know what? Every one of the teachers, Richard Rohr included takes flak from his home ground. So there’s a lot of folks who think he is too far and has gone too far and done too many things. So I guess it’s, everyone can draw the line where it is.

And then I think even he would say, “Stop listening so much to gurus and start listening inside because everything you have is inside. And if you’re plugged in, if you’re doing the contemplative practices you will know.” And what a boring [crosstalk].

Tobi: And no, but it’s such good advice because I think it – well, I mean I love that you just pointed it out because it was showing me that I have a blind spot in a way which would make sense. Because I’ve practiced in that whole first half of life hustle believing the answer was outside of me. And part of moving to the second half of life as you start trusting internally, but kind of old habits die hard. And we all are in a society and a point in time where there is so much to consume, books, media, social media, all of the things.

And I think it’s so easy to not notice and have to re-center and that is the beauty of contemplative practice, whether it’s prayer, or meditation, or whatever you’re flavor of that is, is turning back inward. I love that as a great reminder because it’s so easy to start looking again, especially when what we don’t like is feeling uncertain. And that’s what this looks like and feels like. We want to go, “Well, maybe he has the answer. Maybe this guy has the answer. Maybe this lady has the answer. Maybe this guru has the answer.”

And so that’s such a good reminder that we can hear some things, we can learn some things, we can expose ourselves to some things. But at the end of the day it’s that turning inward that is the answer.

Karen: So I would say a strong contemplative practice, whatever that means to you, and a spiritual director which is simply a coach who will, at the best of them, simply reflect back. They don’t have an axe to grind either. They’re just trying – it’s like a journal that can talk back to you.

Tobi: Yeah, which is kind of the concept of coaching in general, a good coach doesn’t give you advice. They just tell you what you said or what you were thinking, like a mirror, right?

Karen: So I think the two together are what anchor me as I go through some of this, trying on what do I think about this? I know what these five folks think about it but what do I think about it? And then also just not being in a hurry because again that’s a chase of uncertainty, you’re chasing certainty. And what I really want is to be able to hang in the uncertainty.

Tobi: Yes, because again speaking of old habits dying hard the whole idea of being in a hurry to arrive somewhere is the opposite of the softer, allowing, surrendering kind of energy that we’re talking about. And people are like, “What does this have to do with business or any of the things we started with?” To me it has everything to do with it because if you are the leader of your company or your work in the world, to me this personal work has to happen for you to show up in a way that really creates probably the impact you’re looking for.

And the hustle was empty, a lot of us get to the end of the hustle and we’re like, “I thought I’d feel different now.” So I think this work is the work that creates what we were looking for, which just feels horrible when you’re in it.

Karen: It feels horrible. It does have its moments of equanimity, but yes it feels different. The feedback from the world is different. It’s all just sort of – for me it’s calmer. It’s just not as exciting. And yet that is exactly what I guess I’m craving in this part of my life which is like equanimity is a word that sounds like you’re settling for something. And to me it’s if I want to chase anything I’m chasing equanimity.

Tobi: Yeah, so interesting. So if somebody was interested in going this path do you have any resources? I mean obviously the Richard Rohr’s center in Albuquerque and he’s got courses and books and things. But beyond that, are there other books, are there other resources or even resources for a spiritual director if people haven’t heard of that concept before that you would recommend to get on this sort of second half of life train that we’ve been talking about?

Karen: There actually is a – I think if you Google, Spiritual Direction 101, my spiritual director, her name is Teresa, she has that website and she has put out some basic guides about what are we talking about, what does it do. And would you at all find that helpful in your life? So it’s a little bit of a guide. I also think that there’s great, great wisdom in the recovery community and obviously that’s not for everybody. But if there is a sort of – it’s familiar ground, 12 steps, not everyone necessarily knows what the 12 steps are. But it’s been around forever and it’s kind of a bedrock.

There is great wisdom there and there is great healing. And this is exactly – they get the second half of life, that bottom that we’re all talking about, the adrift-ness and everything. If I’m not that, what am I? All that comes with whatever you’re trying to break the addiction with, and so you could be 22 and be hitting this, all of these questions. And there is just a great resource there for that.

Tobi: And so is that literally just Googling 12 step programs or AA or any of that and just literally starting to read the tenets of that type of work?

Karen: Yes, I think that would probably be the best. There’s tons of other resources, I can talk all day. But Richard Rohr has a beautiful 12 step accompaniment book. But it does lean the Christian tradition. So if that wasn’t something that was palatable then that might not be the book for you. But if it did, it’s a tremendous book; Breathing Under Water is the name of the book.

Tobi: So interesting. Okay, well, this was fun. I loved it. It’s so funny to talk about something that you can’t describe, that you don’t have words for and that you say is basically awful feeling in essence but in a sense it’s what we’re looking for or searching for. It’s such a strange conversation yet one that is so – I don’t know – right where I am and I think where you are and I think where so many people are.

And I love that just having this conversation hopefully gives people some sort of relief that their uncertainty is – they’re not in this alone. We’re all feeling this way in response to kind of the world, right?

Karen: And it’s not a problem to be fixed. Uncertainty is not a problem to be fixed. It’s to be – you just sort of sink into it and it’s very – it’s a wise teacher.

Tobi: Absolutely. And I love that you said that because the only way to ‘fix uncertainty’ is to go backwards to the certainty that we came from really. And Brian McLaren talks about that even in his book. He has four stages of kind of evolution for a framework that he created based on his kind of journey with his spirituality and religion.

And he talks about how a lot of times when people get to what he calls phase three, they go back to phase one or two which is like the super rigid very elementary, very in the box certainty even if it is kind of antithetical to a lot of things that you’ve come to believe in because people just can’t bear feeling that way. And so I love that you point that out, that the only way to truly fix something like that would be to go backwards, it’s definitely not moving forward I think. Because once you hit uncertainty it’s not like there’s this point out in the future where you’re going to now arrive.

Like we’re passing through a – it’s not a valley. It’s like kind of the rest of time, right?

Karen: Yeah. I think it’s C. S. Lewis who says, “Ships are safe in the harbor but that’s not what ships in harbors are for.” Ships were meant to go sail on the ocean. And so it does feel like we want to bail back towards the shore and the safe harbor because that open ocean, but that’s where you should head, yeah.

Tobi: Yeah, so interesting. Well, thank you so much for sharing not only what you do but this truly interesting conversation that I know you and I will continue. And maybe we’ll have us back a year from now and see if we feel even more uncertain than ever and what we think about it because yeah, it truly is the journey of life. And I’m excited about it and kind of terrified about it as well. Okay, well, perfect. Well, we’ll be terrified together. Thank you so much for being here and yeah, I will look forward to continuing this conversation soon.

Karen: Thank you Tobi.

Okay. So I know the answer to the question of are you dying to embrace this uncertainty we speak of is probably no. Yet at the same time like me you may very well know that it’s the exact path you’re supposed to be on. So I hope whether it’s the work we talked about in the bottlenecks in your business and how you’re showing up, and how you’re swooping in and starting to get out of the way so you can be supported in business. Or getting out of the way in your own life so that you can really surrender to this next version of you, either way I hope it was helpful.

I look forward to hearing from you. We didn’t tell you where to find Karen but you can find her online. You can find her on Instagram at Karen Sergeant or at karensergeant.com for her website. And you can even get the blueprint, How to Cure your Bottlenecks and Grow your Business on her website. So check her out. She’s on Clubhouse. She’s on all the cool places that the cool kids hang out these days. But check her out, let her know or let me know what you thought of this episode.

And if you have any questions at all, if you’re going to start this journey alongside the two of us we would love to hear from you. Not that we’ll have any great wisdom because it’s inherent in the path that it’s going to feel uncertain just as we talked about. But at least we can sit beside you as we all become more introspective, more contemplative and take the next step on this journey of finding this true meaning that awaits us all.

Okay, I will see you all next week with another maybe not so deep episode. You never know, but I will be back here either way, so I hope to see you soon. Bye for now.

Thank you so much for listening to the Design You podcast, and if you are ready to dig deep and do the important work we talk about here on the podcast of transforming your mindset and creating a scalable online business model, there has never been a more important time than right now. So join me and the incredible creative entrepreneurs in my Design You coaching program today. You can get all the details at TobiFairley.com.

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Hi! I'm Tobi

I help creative women (and a few really progressive dudes) design profit-generating, soul-fulfilling businesses that let them own their schedule, upgrade their life and feel more alive than ever!

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