Ep #139: Running Your Business Your Way with Caryn Gillen

Running Your Business Your Way with Caryn Gillen

Happy Thanksgiving to my US listeners, it’s a strange one this year, right?! How many of us have said, “I cannot wait for this year to be over”? Usually, around this time of year, I do some deep reflection about my life and business and begin to plan for the year ahead. Today’s guest is the perfect guest to help us all reflect on our lives, review our businesses, and see whether we’re living a life we truly love.

Caryn Gillen is a life and business coach for entrepreneurs. She helps them build businesses they love, and love running so they can have more fun, help more people – and of course – make more money. She’s here today to show us how to stop living by the rules we impose on ourselves, and get back to living and working in alignment with our values.

Join us on the podcast this week to learn how to become more in-tune with your values and why it takes intention to create the business you really want. We’re discussing why being successful doesn’t always have to feel difficult and why you can make your own rules based on what works for you. Remember, running your own business means that you can do it your way, and it can be fun!

If you want to do some of this work in the way I’m doing it, then check out my year-end review.  It’s an amazing little tool to help you look at what this year has been like for you and where you want to go next.

If you want help in creating financial freedom and building a business that’s fun and thriving, get on over to the Design You Coaching Program! We only enroll a few times a year, so be sure to sign up for the waiting list ASAP to be notified when we next open our doors!

What You'll Learn From This Episode

  • Why you should show up in a way that works naturally for you.
  • How to reflect and review without judgment.
  • Why working harder isn’t always better.
  • How to observe your own false narratives.
  • The importance of having fun in your business.
  • How to feel less exhausted in your business.

Featured On The Show

Full Episode Transcript

You are listening to the Design You podcast with Tobi Fairley, episode number 139.

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, Happy Thanksgiving if you’re in the US. Today is Thanksgiving. It’s an unusual Thanksgiving. Everything about this year is unusual. But I do hope that you are making the most of today and that you can find some silver linings in this day because it is certainly a day for counting our blessings. For anybody not in the US, I hope you’re having a wonderful day too. So let’s see. How do we want to start today?

I think I want to – I have a question for you, kind of related to what we were just talking about. So here’s my question. How many of us ever said, “I cannot wait for this year to be over?” Which is so interesting, and I guess be careful what you wish for. We have no idea what the future holds. But for me when I look back on this year there’s so many amazing things that have happened. And this is the time of year that I always do some deep, deep personal work of deciding what worked, what didn’t work this year, what I want to do differently in my business and in my life.

And I think that is a perfect exercise to be doing while listening to today’s podcast with Caryn Gillen. So, Caryn is a friend of mine. We’ve both been going through Master Life Coach training together. And she is a life and business coach for entrepreneurs. And as she says in the show, she thinks a lot of what matters is the life piece of this. And I completely agree that we can give you all the business tools in the world but if you’re not really managing your mind and really designing a life you want you’re not going to like what you create.

So what Caryn does is she helps people build businesses that they love and love running in the day-to-day. Imagine that, that you actually like your business. And her whole purpose is to help people that – these people, the entrepreneurs have more fun, help more people and make more money. And she has all kinds of coaching certifications. She has a master’s in counseling psychology. She’s a super smart lady. But I also love just how calm and commonsense she is about really creating a business that we really, really want to be a part of every single day.

So I know you’ll love this episode. It spoke to me while we were doing it. It was right while I’m in this very work of deciding what I really want. And I hope that it speaks to you too.

Tobi: Hey, Caryn, welcome to the Design You podcast.

Caryn: Hi. Thanks for having me.

Tobi: We have been trying to get you on here for a while, so this is really exciting.

Caryn: Yeah, we finally made it, I’m happy to be here.

Tobi: We did. Okay, so we are friends from going through Master Coach training together. And we weren’t even in the same training group when we were doing that in Grand Cayman. But we would have meals together periodically you and I, and got to know each other, which was fun.

And I’m so excited to have you here today because I want you to tell everybody about you and what you do. But what you’re talking about today is speaking right to my heart at this very moment and I know I’m not the only one. So tell people a little bit about what you do. And then we’re going to get into a few of these key ideas.

Caryn: Okay. So basically I call myself a life and business coach for entrepreneurs and coaches, because I think life is a really big important part of it and how we do life is oftentimes how we do business. So I help people in business stop living by the rules that they think exists about how to do business. And stop creating the business they think they should have. And get back to the work of creating the business that started you off on this journey in the first place, that idea you had, wherever you were and you knew this is the thing for me.

And then you went and learned a whole bunch of stuff that then just got in the way of you doing what you’re actually here to do.

Tobi: So good, okay, so getting in the way could be anything from tools, or techniques, or thought processes, or seeing bright shiny object syndrome of what other people are doing. All of that potentially muddies up sort of our vision for where we’re going.

Caryn: Yeah. And it’s confusing because all that stuff is good stuff. So it’s like is it good for me? Is it good for me right now? Did it work for me then? Do I have to keep doing it? We get to change and grow. We do not have to do everything we’ve always done just because it worked once, just because it worked for so and so, just because the guru said it. We get to do it our way.

Tobi: Yeah, I love that, okay. So let’s start with this idea of these rules and really what really struck me is when you said, “The business you think you should have.” Because I’m in this process right now, and I do some deep work, well, all the time. And this time of the year every year I’m kind of starting to assess and look at what’s working and what’s not working. But what I’m really digging into right now is the fact that I kind of had this revelation, cleaning out my closet week before last, which I was the only person.

I’m such an organizer, and I’m the only person who didn’t organize this entire last eight months that everybody else was organizing. But I started doing this work and I saw that I had these clothes in my closet that were, for whatever reason I hadn’t gotten rid of, that don’t fit me. And then the whatever reason was that they were super expensive and I was telling myself some story that if I’m super successful I will get back into those.

And I’ve had this huge aha moment that not only was I kind of holding on to some past version of something I thought I should be. But not letting go of that was keeping me from becoming what I could be. And kind of even another level this kind of meta, thinking about your thinking quantum level. I had this other realization of – and the thing that I’m trying to get to maybe unconsciously or whatever, I don’t even want. It’s some story that Tobi, you’re so powerful and you can be anything, so you should want these big grandiose things in every single part of your life.

And you should strive for this perfect powerful version of you. And I had this huge aha moment and I was sitting there and it was this weird combination of grief and relief. Kind of grieving of the letting go of the story that maybe somewhere for a long time I’ve been thinking I should become. And then this whole relief of I get to become anything. And then the terror of what the heck is that going to look like.

And so I think people find themselves stuck all the time. It’s really this place of stuck between afraid of failure and afraid of success if we want to boil it down to the just like two little kind of tiny labels. So does that apply to what you’re talking about? Because that’s what came up for me when you said, “The business you think you should have.”

Caryn: Yeah, 100%. It’s like living all the versions of our lives at the same time, or trying to and then we’re just stuck right here.

Tobi: Yeah. So what do we do about that? How do we start to let go? Well, first, how do we start to become aware of these rules, these arbitrary rules that we kind of don’t even know we’re running in the background of our mind maybe, or that we’re trying to meet? And then how do we start to let go of those?

Caryn: I think the easiest way to do it is if you can tune into what’s the energy in my body. Sounds a little woo, right?

Tobi: No, I like it.

Caryn: It’s like when I look at that item in the closet and I slide past it again because I know it doesn’t fit me, what does that actually feel like in my body? Does it feel like dread? Is it heavy? Or is it like I’m excited to get where that outfit is going?

Tobi: That’s so good.

Caryn: You can have an aspirational pantsuit in there for the TED stage or you can have the pantsuit you wore to that wedding that makes you feel crap.

Tobi: A loser, yeah, a failure, yes.

Caryn: Yeah. So I just like to tune in, does this feel – and I use the words fun and ease a lot. So does this feel like fun? And what would be easy? So can I let it go? Am I going to have fun with this? Does this energy feel light, uplifting, effervescent? Do I actually expand in my body? I’m kind of puffing my chest out when I think about it. Or is it a contraction? Does it bring in that like a little bit of shame, a little bit of regret, a little bit like oh? Am I using the word ‘should’? If you’re finding a should anywhere, that’s when you need to check-in, that’s the check engine light is that word for sure.

Tobi: That’s so good. And I want to dig a little deeper into these two emotions or two kind of states of being you talked about which were fun and easy. Because when I think about the two of those, I don’t even think I have access to either of those. I don’t practice those. I have this almost accidental belief, and I think a lot of people do that if things are worth doing they should be hard. And we should grind and it should feel gritty and it should feel like we’re proving, or striving, or forcing, which we know doesn’t make any sense logically. But I think that’s where a lot of us go.

So I think we discount ease a lot, we don’t know what to do, or I don’t know what to do with it. And then fun is a whole other ball game. I’m just one of those people that are like we’re responsible. What do you mean, fun? I’m not an Enneagram seven, that’s just for those spontaneous people. But the rest of us actually have to come to work every day, right?

Caryn: That’s so awesome you said that. For a while I thought I was a seven because I do really value fun, but I’m not, I’m a nine. Yeah, I think it’s not accidental that we think we need to work hard. We have all been brought up by people who grew up where working hard is actually what created and saves our lives. So let’s just say that’s perfect and it is our job to get out of it because it’s not necessarily the thing that’s going to get us where we’re going anymore. That’s [crosstalk] thinking, we don’t have pensions anymore.

Tobi: Exactly. That’s a great way to describe that because I remember sitting at a Mastermind for Life Coach School about a year ago. And having this revelation, this literally kind of took my breath away of the whole reason I haven’t already met my goals is because I’m working too hard. I mean it was like this crazy, like it stopped me. It was within the first five minutes, something was said. I don’t even know who it was by for sure that said it. And I was like holy crap.

My to do list is killing my business. My striving is killing my business. My attachment to overachieving or goal slaying or all this stuff is what’s keeping what I really want at arm’s length from me.

Caryn: I just think I like to visualize nose to the grindstone, what is your body doing when you’re doing that? You’re hunched over, you’re not looking up. You’re not really paying attention to what’s going on. It’s all this focus in this one tiny space in front and eases, like periscope up, what else is out there, what are the other options? It’s curiosity I think is in fun.

Tobi: I love that so much. And what I love about it is I don’t know about you. But I often catch myself and have some little micro regrets through a day when I find that I have been so into my computer or so into my phone, which is that exact same posture, that I missed out on somebody that mattered to me. So a lot of times if I’m working and my mom lives about 45 minutes away and we’re real close and I see her quite a bit. But if she drops by my house for something and then I notice she left.

And she’s like, “I left that on your counter.” And I have a moment of I did not walk down there and get a hug. It almost makes me emotional to think about it. I did not look her in the eyes. I have no idea what color she’s wearing today. That’s like a little mini heartbreak for me. And that comes, and it happens with my daughter, it happens with other people in my life. And that kind of not being in the present moment for me is the epitome of that nose to the grindstone that you’re talking about, and that posture, and that missing out on.

And it’s funny because the reason I think we’re doing those behaviors a lot of times is some level of FOMO. And we think and like need to achieve, yet we’re missing out on all the good stuff when we’re in that kind of a hyper focus a lot of times. Not that we can’t have moments of that. But I think when we get in the habit, don’t you, of this grinding away at some business we think we should have, as you say, that’s kind of the result we create.

Caryn: Yeah. And if you just think back to why did you start this in the first place.

Tobi: Yeah, to have more of those moments where you could look at your mom’s face and see what she was wearing, and take off in the middle of the day and sit outside with your kiddo or whatever. All those little things are the things, yeah.

Caryn: I think every once in a while we’ve got to feel like we’re getting away with something.

Tobi: Talk about that a little bit.

Caryn: Tuesday at 11:00am when you’re supposed to be having your focus time or whatever, and work on something. Would it be more fun to actually – this is what I used to do, go to that coffee shop that I really love and be in all the energy and the bustle of it instead of being right here nose to the grindstone. Have fun.

Tobi: Yeah. So how do we start to build a business that feels expansive like that? Because that sounds incredible to me, and I know one of the first answers for me would be to constrain other things. Is that part of it? Is that like, because that’s where that grief thing came in for me of bidding farewell to these things that kind of I don’t even want or that aren’t even for me, but at some level I feel obligated to them. But how do you build that expansive feeling business?

Caryn: Yeah, for one that’s a really good idea, because anything that is holding us back energetically we’re also just holding space for it in our lives all the time. So anything you can identify to get it out and away, even clearing out your online files could be like that, of all your old business ideas that you know you’re never going to do anything with. Just trash them, you’re the person who’s going to create more and better later, it’s perfect.

Tobi: I love that so much. I love that you’re saying, so that’s a term that we didn’t understand for sure in coaching of holding space, which when you’re holding a space for a person you’re just there open and listening. But what you don’t realize, this is so fascinating. It’s kind of like that meme that says do you ever feel like you have 72 tabs open on your laptop or whatever. And so that’s kind of what you’re saying is if you’re holding space for all of these versions of you and all of these things you could be or you might do, it’s all kind of running all the time in the background.

And that is an eye-opener for me. Wow. And I feel that, I feel that kind of fatigue at the end of days a lot of times and I’m like how could I be this tired? I haven’t even done that much today. I haven’t – I’ve kind of, you know, I’m fatigued from my thinking of course, because our thoughts create our feelings. But this particular type of scenario, I could see that would really play a role in that kind of fatigue.

Caryn: Totally, yeah.

Tobi: Yeah, that’s fascinating. Okay, so let’s talk about that letting go of things. How do we let go of things?

Caryn: Easily.

Tobi: You do. You do. How do we – I mean you know what? I keep using this term like grief. And for me it’s some level of – I don’t know, there’s this weird space for me between…

Caryn: You’re like killing your darlings?

Tobi: Yeah, kind of, killing your darlings and like – trying to think, there was a time that my friend Betsy, who’s a coach said to me earlier of – how did she say it? She said, “Knowing you could be something and being okay not becoming it”, or something like that. And that’s a really – for overachievers…

Caryn: And acknowledging it.

Tobi: Yeah, overachievers type A, at some level it can feel like we’re settling. And then you kind of have to step back and be like, “But wait, that kind of wasn’t even really my dream anyway.” And why am I believing, just because I ever wanted something at one point that it still has to be what I want now? And I think, so it’s this part of me, and I know other people probably struggle with this, of quitting something.

Caryn: Right, yeah. And what do you even make quitting mean versus we’re just stopping. We all have multiple potentials to do an incredible number of things really, really well. And we always are at choice to say, “Is this actually the dream I’m on? Or is this the thing that got me to the place where now I’m ready to do the other thing?”

And it’s a big deal, like when I left my corporate job that paid really well, I had great benefits. I got to work with these amazing female scientists. It was like this is awesome. It is crazy that I’m leaving and I’m going to leave anyway. I’m going to leave loving it and being okay with it. And I still love them.

Tobi: Yeah. So can you talk a little bit to that? Because I think that’s a concept people don’t really understand, because most of the time the only time we quit something is when we’re miserable and we hate it. And we’re leaving in some kind of negative emotion, or pain, or suffering, or anger, or blame, or some level of that. And what you’re talking about is something completely different. And I can see how for me personally if I had a thought about anything I’m letting go, the way you’re describing it, it would feel much more like releasing than quitting, or losing, or grieving.

Caryn: Let them go too. Yeah, like the person who has that job now, it’s so amazing for her too. It’s the same with our employees, it’s like if I’m keeping somebody here and this is not the place for them, that’s on me too. I need to let people go find where they need to be. And sometimes I’m helping people go find their dream and sometimes they’re helping me find the dream person for that role by leaving themselves. But who’s to say what’s good or bad about being here now or being not here later?

Tobi: Yeah. So if we start to also kind of apply that to these ideas of tools, tools we’ve seen, ideas we’ve had. Because that’s sort of the same thing because in a sense we idolize certain people, people idolize me or you in the roles we play. We idolize our mentors, or celebrities, or people we’ve seen be successful. And it’s like if somebody said something and we are ignoring it, we must be being irresponsible, or if that was the thing that was going to get us.

And so it’s the same mindset of being willing to sort of take what you need and leave the rest. But also knowing what you need at any given time.

Caryn: Yes, that only you know.

Tobi: Yeah. So how do you know?

Caryn: I think it comes back energetically again. Sometimes it helps for me to look at the person, to look at the mentor and be like, okay, so I’m a really calm person. They’re pretty anxious. I’m going to show up differently. I’m going to have different needs than them. I don’t operate in the same way they do. So what they do, how they structure their life and their self-care, it absolutely needs to look different than how I do that for me. Can I take what they do for them and make meaning that I like for me? Yes.

Can I take what they do for them and make meaning that feels terrible to me? I can also do that. So it’s how am I using everything that I’m learning for me because nobody else cares and nobody else is going to do it for me.

Tobi: Yeah. So if we then start to try something and here’s I think a little nuance that people get confused with because what’s the difference between this is not right for me, at least right now and, I’m just not wanting to do hard things and feel uncomfortable?

Caryn: Yeah. Apparently I’m really in energy today, but I understand that…

Tobi: No, I agree with you, because a lot of us stay in our headspace all the time and we never drop into our body and feel anything, right?

Caryn: Yeah. So I think it’s like if you think about the day that you watched the full season of your favorite whatever on Netflix. And you laid there and you didn’t pick up your phone and you watched the show and you enjoyed it, and it fuelled you and you were like, “This is amazing.”

That’s total love for yourself versus the day that you sat on the couch and you watched the full season of the show you like on Netflix. And you felt like you were hiding and you were scrolling your phone. And you were going back and forth to the fridge because you were just distracted. Those are very different experiences of doing the exact same thing, what’s restorative and what’s actually depleting you. And I think we can use that to find the way.

Tobi: And I’ll say that probably if I think about the – and I notice this consciously when it’s happening. The last five years of watching Netflix have almost all been the one where I was also scrolling and also doing something else, which is, kind of goes back to that place of what you said. I’ve got all these tabs open, am I holding space for all these other things? And as long as we’re not willing to kind of bid farewell, or at least for right now, constrain or park these things, then we’re going to be going through life in that way all the time, distracted and all of that.

That’s so interesting, because we want to just blame the phone, we want to blame the phone, or we want to blame the to do list. If I didn’t have all of, you know, we were all watching Social Dilemma. Yeah, they’re brainwashing me. But really what we’re talking about is designing a business that you love and that you love running is really just about you making some conscious choices, right?

Caryn: And being in relationship with yourself. And being honest about what yourself is reporting back to you. So it’s like something feels really restrictive and draining, listen to that. If something feels like it opens you wide up and you have more access to creativity, listen to that, even if nobody else around you is doing that thing and knowing it’s not working for them, it could be working for you and that could be perfect.

Tobi: Yeah. So one of the things that I struggle with and I’m sure that you help people with this a lot as entrepreneurs and CEOs is the getting your finger out of every pie. The level of control, because I think some of what we’re talking about is just deciding not to do something. And other parts are no, the company can still do it and I can not be involved in it. And I think that’s a whole other thing and a whole other set of mindsets we have to think about of letting things…

And here my struggle is sort of how do I release control but not lower my standards for my expectations of how things are done too. So where does that play a role in what we’re talking about? Because I’m making some decisions again of what to let go of, what to keep doing. And there’s always a little part of me that’s like, but maybe we can keep that, it just won’t be me doing it. And sometimes that’s a good idea and other times it’s like that’s just a workaround for you to not have to let go of something that has run its course or whatever.

Caryn: Yeah, I think on that one it’s a values check back, does this actually fit my values? Because any of those things, it becomes really clear if you know what your values are, what’s happening under them and what’s happening in me trying to skirt my way around and not have to deal with something.

Tobi: Okay. So how do people start to really know what their values are, what does that work look like? Because I think you’re right, and we’ve done this work this year for my company that we hadn’t really ever done before. And it does make the litmus test so much easier to just go, “Does it apply? Do these employees fit? Do these contractors fit? Do these tools fit? Do these revenue streams fit?”

But I think one of the things I see is people, they kind of feel like they know what they value but they’re not really clear on it. They don’t have it written down. They couldn’t put it into words. And even when they put it in words it sounds kind of corporate and not really authentic. So what’s the best process for getting to the root of those?

Caryn: Yeah. I think there are a lot of people who will take you through a values process and we want to look good. But our values are very unique to us. They don’t always look like what you would see on the wall of whatever big company. I just did this work for myself again recently. And freedom, and ease, and fun, those are in there and alignment is also in there. And I was a little bit surprised because I was like, but that’s just the stuff I talk about all the time. I’m like, alright, because values work is easy, our values leave clues all around us.

So rather than go do some big process to discover what your values are I would just look back at the last six months and be like, “Well, what have I been talking about? What have I been doing? How have I been showing up for other people? How have I been showing up for the goals we have? How have I been showing up around revenue? How have I been showing up around all of it – family? And what’s really clear?” Because they’re not hiding.

Tobi: And not ignoring those clues I think, I was on a private consult with a client yesterday. And she’s like, “I still just haven’t adopted your time blocking system that you teach.” I’m like, “Well, that’s okay.” And she’s like, “Yeah, but I’m just not good at it.” And I’m like, “Well, tell me more about that.” And she’s like, “Well, what it looked like is I realized I was putting all this extra time in for thinking and basically all this extra space.” And she’s like, “And so I guess it’s just a copout because I’m just not doing what I’m supposed to be doing.”

And she’s like, “I just don’t understand what you mean when you’re like, “Our calendar will show us.” And I’m like, “That’s exactly what I mean. If what you’re saying is, “I need to do all these tiny little tasks”, but what you’re actually doing is thinking, and strategizing, and having a more expansive schedule, then that is your schedule. That’s what it’s supposed to be. You’re not listening.”

And so this is exactly what you’re talking about today of she thinks there’s these rules that she should do all these other things. When in reality as the leader of her company she needs to be doing exactly what that calendar looks like, and she needs to either eliminate or have other people doing a lot of those other things, right?

Caryn: And I think that goes back to the idea of it should feel hard. I just want it to be successful, it shouldn’t be easy. But if you look back at how you operate and you’re non-judgmental about it, you just look at it like a scientist, well, let’s see how does this person show up on a regular basis? Easily, I can easily start my day at 11:00am serving clients and love it. I could start at 9:00am. Then I have to manage my mind around hurrying in the morning.

So do I want to spend my time managing my mind around hurrying? Or do I just want to show up in the way that works for me naturally and allow that to be the way that it goes?

Tobi: I love that so much. And how many people are sitting there going, “I could never start my day at 11, I’d never get anything done, and I’d feel lazy.” And that’s what you’re talking about, when you start to notice, where do these rules come from? What thoughts are you thinking that are driving you to be on that treadmill all the time, to be in that hurry up kind of state of urgency all the time? Because when I hear people say, and I hear it a lot and I know you do too. “I’m not having any fun anymore, this is just not any fun, there’s no joy in my work.”

It’s something as simple as well, then why are you starting your day at 8 when you could start it at 11? That one shift and honoring what your body and you want, that’s what you’re talking about, right?

Caryn: Yeah. And then some days I get up at 6:00am and I put in an entire workday working on my business before I see a client. And it feels amazing, and I have the time to do that. So I get to answer the flow of what works for my body and then put my clients and put my meetings where I know I will want to show up and not feel rushed to show up.

Tobi: So can you talk a little bit more about that? Let’s talk specifically about time because I think that time is one of the biggest rules people have for their businesses. And that sounds so lovely what you just described, of allowing kind of how you feel to drive how you show up. But then there is that flipside of the coin of like I see so many, especially the creatives I work with saying, “Well, I don’t feel like finishing this client project today.” And then they have no money coming in.

So again, how do you kind of figure that out to make sure that you are hitting the things that are required to really live your dreams also, like some money goals and that kind of thing versus the allowing yourself to do what comes naturally or easy for you?

Caryn: Yeah. So a while back I took the Gretchen Rubin Four Tendencies Quiz. And I’m an upholder, so I know that I will always show up and do what I said I would do. A lot of people are obligers and…

Tobi: That’s me. No, wait. Yeah, I think that’s me. What are the four?

Caryn: It’s rebel, questioner, obliger and upholder.

Tobi: I’m an obliger, yes, 100%.

Caryn: Right. So you know you’ll always get it done for somebody else before you’ll do it for yourself.

Tobi: Yes, absolutely.

Caryn: And questioners are always just going to ask a ton of questions, that’s part of their process. And rebels are going to rebel against it even if it’s the thing that they really want. So I just like to think how can I actually just set it up so that I can be successful and not fight against my tendency?

Tobi: Okay. So for an obliger, if a lot of people are that, what would that look like compared to what you would do as an upholder?

Caryn: For you it would just be I’m going to set myself up and tell so and so I will have it to them by 3:00pm on that day because you know you will, yeah. And if you want to have it done early, you tell them you’ll have it to them earlier than that.

Tobi: Yeah. So the problem with obligers then is just being aware if you’re cramming a whole bunch of stuff in and telling – it’ll almost be like saying, “Okay, I can only tell x number of people a week or a day that I can do something for them.” Because if I obligate myself to 12 people then there goes my self-care, there goes my workout, there goes my rest, there goes my connection time, all of that stuff. That’s really great, I love that. So then for someone like you, how does that look different?

Caryn: It actually looks similar, I just put it in the calendar for myself and I hold the agreement. It’s just like one of my core values is I do what I say I’m going to do.

Tobi: Yeah. So if you say, “I’m working out, I’m working out.” If you say, “I’m not starting my day till 11”, you don’t then suddenly start it at 9?

Caryn: Yeah.

Tobi: Yeah, okay. And then rebels and the others, anything for those other people to be aware of as they’re thinking about that?

Caryn: I think for rebels, you want to not beat yourself up for being rebellious against what you want. This is just a part of your nature and how can you use it for you, if you know you’re going to rebel against it, how can you set something up so you still get what you want? Just play yourself.

Tobi: Yeah. I’m an obliger, but I do have a little bit of that, you can’t tell me what to do in my personality. That might come from my Enneagram 8, if you believe in all those different things. You won’t control me kind of, while at the same time I’m an obliger so I follow through, I’m just mad about it. I’m internally rebelling while I’m not rebelling, which is kind of…

Caryn: Obliger rebellion.

Tobi: Yeah. It’s kind of the worst of both because you’re like, well, I’m mad as hell I’m doing this, but I have to do it because I’m responsible. But, yeah, and all of that goes back to energy I think, which was your original point, because you’re going to know if you pay any attention, if you’re rebelling, it feels a certain way. If you’re feeling obligated, which is that obliger thing, and you don’t want to be.

I remember the person that we both learned life coaching from, Brooke. I remember her one time saying that she doesn’t feel obligated without her consent and that really spoke to me. Because I think kind of inherently in obligation is a lot of times it’s not with your consent. And so I think that’s part of this whole rule thing too. Why? Why am I feeling like I have to follow through? And usually a lot of times for a lot of us, it’s some level of people pleasing as well, right?

Caryn: Yeah.

Tobi: Yeah, interesting. Okay, so anything we haven’t really talked about yet that it’s really important for people to know about this, how to grow into a business that they absolutely love running?

Caryn: I think the main thing you want to know is you’re probably not going to see out there what it’s going to look like for you. You’re going to see lots of little pieces of it but there’s only one of you and one of your brain, and one of the way that you’re going to do this, and that doesn’t mean there’s anything wrong.

Tobi: That’s great advice, because we’re usually looking for what’s wrong and we’re usually comparing, which gets us into a lot of trouble. When we’re comparing ourselves to all the businesses we see and the bright shiny object thing, instead of kind of stay in tunnel vision, that’s when we get ourselves in trouble. So when something new does come up that you think might have some validity that you might want to try or test, should you just jump into it?

Does it depend or is there some of level, well, you know what, I’ve already decided what I’m doing for this next six months, but I’m going to put that on this list to come back to when I’m ready to kind of tweak things again? What’s the most healthy version so we’re not kind of always doing the shiny object syndrome, or squirrel kind of thing, which a lot of people try a lot even by accident and they end up all over the place?

Caryn: I think if you’re looking for a shiny object, well, for one, you’re always going to find one.

Tobi: True, yeah, especially if it’s a good way to procrastinate on doing what you actually need to do, right?

Caryn: Yeah, so this in itself is a good place to check-in and be like, what is it? What’s the skill that needs building? Or what is the problem that needs solving? And does this thing do that? So kind of wherever you would spend your money or spend your time, which is your money, it needs to be because you’re developing a skill for you or your team, or you’re solving a problem for the business.

Otherwise you’re being really clear with yourself that this is completely for fun, this is just for my brain to play and I’m not expecting this to move my business forward. And be really clear about that ahead of time.

Tobi: Interesting. Can you give me an example of something that would be just for play?

Caryn: That’s how I did Master Coach training. I was really clear that it was going to take time away from my business, time that I didn’t necessarily want to take away even. But I also knew I wanted to do it, every five years I like to make a big investment in the craft of coaching and it lined up for that. And I was like, “I’m going to do this and I’m going to meet a great community of other coaches. And that’s going to be the thing I’m going to do.” But I knew it wasn’t this direct thing that was going to affect moving my business forward in any other way.

Tobi: Which takes a lot of pressure off of it too, because it’s almost like auditing a course in college instead of getting a grade for it, yeah, like just trying it out and seeing what happens. But I just had this conversation with my coach yesterday for the very same reason, talking about anything, whether it’s a course, Master Coach training, a book I’m reading. Going back to the same issue of not being willing to quit something I’ve started, even if I’m not really enjoying it again.

So I think even at that, when you can play at something, do you feel like that relieves some of the pressure of having to complete it?

Caryn: Yeah.

Tobi: Yeah, that’s interesting.

Caryn: But then I have my upholder self who’s like, but we finish what we start, so we will finish it.

Tobi: Yeah, I obviously have at least some of that too, or the obliger, I committed to this person, not myself, so I’ll finish. Yeah, I agree, that’s really interesting. Okay, this has been so good. I love just how – I mean just the fact that you’re so calm shows the difference. Because you’re, you know, showing my intense energy which is always kind of this just tackle things. And that’s kind of what you’re talking about. When you start to let fun and ease and some of these things come in, maybe you’re not taking things so seriously, or at least it’s not on steroids all the time, right?

Caryn: And I mean most of our businesses, we’re not running hospitals, nobody’s going to die today because of what I do or I don’t do. This is all optional. We’re working in these fun areas, designing beautiful spaces and working on our mindset, this is optional. None of this has to happen.

Tobi: That’s interesting. So how do you stay committed to it if it’s option? Where is the, oh well – to me that’s the thing that always creeps in, which is the other side of the coin because it’s kind of like, I guess I have a fear of if I make it too fun, and too easy, and too optional then I just won’t follow through and do it.

Caryn: That’s the same as people thinking I have to be on a diet my whole life or I’ll weigh 500 pounds. Like that there is not some set limit in myself. I think in business it’s like, no, we’re here because we love it and we chose to do it. And even if you took all the rules away you’d still be here. If you gave me a billion dollars, I would still do what I do right now.

Tobi: Exactly, which is really that whole idea, if you want to call it that, of coming from a place of abundance instead of scarcity, and scarcity for me feels really icky in my body and my energy. It feels lack, it feels graspy. It feels sometimes like forcing. And then the other, again, like you said earlier, people can’t see you, but it just feels so expansive and like you could take a big deep breath in which feels so good to me always, especially when we spend a lot of our time not even breathing, holding our breath.

Caryn: Yeah. And I find that most of the time in my life right now, I’m sure this wasn’t always true, scarcity is never actually the truth.

Tobi: Interesting, tell me about that just a little bit more before we wrap up, that is so good.

Caryn: Yeah. If you’re in a hurry and you really play it back it’s like what am I hurrying for and what’s the point of that? And if I am worried about money, but if everything ended today, we would be okay, we have this much. Just reminding yourself I actually have everything I need. I am taken care of. I have food. I have a house. I have planned for this. All that stuff.

Tobi: Yeah, so kind of noticing those false narratives or habitual thinking, yeah, that’s so good. I love that. I love asking that question because I do think even – I sometimes hesitate to use words like scarcity. Because I think just like a lot of other words, we start to use them as an excuse or a buffer of, oh, I’m in scarcity. That’s normal, I’m just in scarcity.

And I love that you’re even saying, “Question that”, because is that really true. That might have been a scarcity kind of driven action, but are you actually in scarcity or are we needing to be in fight or flight at this moment? Or is it some story you’re telling yourself? So good.

Caryn: It’s a transient feeling, yeah.

Tobi: Yeah, so good. Well, thank you so much for taking us through this process. I think everybody wants exactly what you’re talking about, which is a business that they really love. And like I said it just – the minute you said, “This is what I want to talk about”, it spoke to me so deeply as I’ve shared, just because it is a process, it’s a process of – I don’t want to put so much pressure on that of like it’s hard, it’s a process. But I think it at least takes intention to become the version of you or create the business that you really do want.

Caryn: And the good news is you’re always with yourself. You’ve always had the one main power player that you need to be with you through the process.

Tobi: So good, yeah, trust yourself. I mean that’s kind of what you’ve been implying the whole podcast is all of this stuff that’s outside of you can give you some clues. But at the end of the day you know what to do and you’re always there making the decisions. So good. Well, thank you so much. This was really great. If anybody wants to hear more from you, find you, connect with you, how do they do that?

Caryn: caryngillen.com and I’m at caryngillen everywhere because I have a weirdly spelled name, so I’m easier to find.

Tobi: Okay. And it’s C.a.r.y.n. G.i.l.l.e.n?

Caryn: Yeah.

Tobi: Caryn Gillen, okay. Perfect. Well, thank you so much. I’ll report back and if you’re even interested and let you know how good I get at quitting some of the things that I don’t even want to be doing in the first place, and if anybody else…

Caryn: I would love to hear.

Tobi: Yeah, fun. And if anybody else wants to share, Caryn and I both would love to hear from you. I know this is sort of something we’re all – and it’s sort of indoctrinated into in this super achiever world we live in. And so this is worthy work. And yeah, we’d love to hear from you. So again, thank you, I’m super grateful for you and it was great seeing you today.

Caryn: Thank you.

Alright, now, Caryn and I want to hear from you if you have any questions, because again, this is deep work and it can kind of feel scary sometimes. Like I said, for me, letting go of some of these ideas of what I might be or could be, or maybe even should be, which she told us, any time we hear should it means that we’re not doing something right. We’re not really picking a business or a choice that we love. And I do feel that way sometimes.

And so it can feel like grief, it can bring up fear and all sorts of things. But it is very, very worthy work of really building the life that you want. So I hope it was helpful.

Now, if you want to do some of this work in the way I’m doing it and have some prompts to help you think about what worked for you this year and maybe where you’re headed next year, then check out my year-end review. You can get that in our show notes. You can get to it by going to tobifairley.com/2020. That’ll get you this amazing little tool to help you look at what this year has been like for you and where do you want to go next. And remember, if what you took from this podcast is that you don’t need any more tools, then listen to your gut, don’t go download it, but it’s there for you if you need it.

Take what you need, leave the rest as we said, but if you want to take a look at it, then you can head over and download your copy. It might really help you get to the root of what has worked for you and where you want to go next. And maybe a few things, or if you’re like me a lot of things, that it’s time to bid farewell. So, I will see you next week. I’m so glad you were here. Talk to 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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