Do you ever feel like you’re stuck in a dead end job but you’re not sure how to move on?

Have you ever set a big goal that always seems to linger just out of your reach?

Has the fear of the unknown ever stopped you from going after what you really want?

This episode features our special guest Caroline Garry. She’s talking to us today about the big risks she took that led to a better life for her and her family. Caroline will walk us through the puzzle of assessing risk and how to make calculated and strategic risks to achieve more than we thought possible.

Take a listen to get some inspiration for taking that next big step! 


Audrea Fink: [00:00:00] Are you stuck in a job you don’t like? Are you passing up business opportunities because they aren’t a guarantee? Do you want to make a big change but are fearful of stepping out of your comfort zone? Today on Think Tank of Three, we have a special guest to help us get over being afraid of taking risks but making sure we’re being smart about it.

[00:00:17] [INTRO]

Audrea Fink: [00:00:50] Welcome to the Think Tank of Three. I’m Audrea Fink, here with Julie Holton and our special guest Caroline Garry.

Caroline owns a brand strategy, visual design, and customer experience consultancy. She approaches brand with a business mindset to drive initiatives that increase profits, improve perception and awareness, and promote the brand’s culture and values. She has significant experience in the health care industry, and when she’s not chipping away at those messy systems, she’s helping startups to secure funding by perfecting the art of the investor pitch and helping nonprofits to build a community by building better brands. She’s worked with clients including Virginia Mason, HCA, Anthem, Populous Global Architectural Design Firm, and National Co-op Grocers. Caroline thank you for joining us.

Caroline Garry: [00:01:38] Thank you so much for having me.

Audrea Fink: [00:01:39] Caroline and I met through the Leadership Tomorrow program in Seattle and bonded pretty quickly. So we were at a happy hour, and Carolyn started talking about some of her history and her skill sets with calculated risk, and as it turns out, she is a master at taking risks. And I thought this was such an empowering topic. I really wanted to bring it to the Think Tank.

Julie Holton: [00:01:59] So let’s dive right in Caroline and talk about what is calculated risk. Can you break that down a bit for us and give us an example?

Caroline Garry: [00:02:07] Sure. Well when I was thinking about talking with you all today I thought about how I advise clients in business risk, which is so different [than] when I was reflecting on personal risk. But a lot of times what I do is weigh trade offs.

Every choice that you make you’re making a trade off decision of this as opposed to that. And it really helps to consider all possible outcomes and not to be tied to any outcomes. So I just want to emphasize the words Possible Outcomes. So it could be things like, who are my competitors? Who’s already in this space, and how are they owning that space, and how could I be different? What are the risks of an already crowded market? What are the financial risks?

I think a lot about things; a really specific example would be somebody who’s really wanting to open a small business but maybe there’s a large overhead investment–a cost that they can’t get around. For example, I’ve got one client to starting a coffee roasting company and had to invest in a roaster and it’s an expensive, hard cost, that he really can’t get around. But in order to pursue his dream, he has to.

There’s operational risks and reputational risks. If you think about having a strong point of view, right, as a business and maybe you come out and say you’ve got a political view or a values-driven view, and you risk the possibility of alienating a customer base. So those are–there’s a lot of things; there’s probably about, I don’t know, 50 more that we could list, probably actually closer to 100. But, it’s really taking an analytical view at all of those things because a lot of times our emotions play a much larger factor in the way that we make decisions than we really think that they do.

Julie Holton: [00:03:52] It’s really interesting the concept of reputational risks that you just touched on because you work with a lot of your clients on strategy and on building your brand strategy, and something that we’re noticing a lot right now, with the movement right now online, especially with social media, is seeing brands–big brands–start to stake their reputation behind causes. And we see a lot of CEOs and business leaders that are speaking out on causes and we find that the consumers really want this. They really want to know that the company they’re supporting with their dollars is taking action. And I would consider that to be a really big risk. So talk about that a little bit. How do you advise your clients when it’s kind of blurring the lines between personal and professional?

Caroline Garry: [00:04:43] This is such a great question. This actually goes to a lot of what we’re talking about in our Leadership Tomorrow class, too, about how do my personal leadership values come in conflict with my professional leadership values? And my answer is gonna be; it’s gonna be really straightforward, because I have a small business and so it’s my choice. I’ve taken the reins on that and said, “I’m going to stand behind things that I believe in and say, ‘No thank you’ to those that I don’t,” even if it means losing a job or scope that I could win. We talk a lot about authenticity and brand building and it’s become such a buzz word and so has storytelling and so has all of these many things that we’re really using in this very bizarre way to manipulate people’s emotions and feelings. That’s what brand does and I’ve struggled over the years with my feelings on that. I think it can be used for great things though, too.

And to your point: when a company says this is what we believe, this is who we are, this is what we do, and this is what we believe; this is why it matters, I think it really builds trust. And my opinion is when it comes to things like building loyalty or share of wallet would be the more business-y way to say that with customers you’re really looking to build their trust. And when you have that it’s the same way that we make decisions about our friends and our families and all of the other things that we hold dear.

Customers are so much smarter now than they used to be. They’re not a captive audience in front of a TV at 5:00p.m. watching the news anymore. And so there’s not this top down funnel of the way that we consume media. And so there’s just–it’s so pervasive all of way that we–the inputs that we have and companies that are smart are picking up on that and they’re realizing that it’s very off putting actually to kind of have the company-man-brand point of view which is very perfect and people know that that’s not the truth.

Like the truth is, I used this reference this week actually: health care companies really want to build the app, right? An insurance company for example let’s go like an app and we want to empower patients and there’s gonna be a lot of wellness tools on there and cost in transparency. And that’s great. I think a lot of times the health care companies really do want to do that because they feel like they’re behind, right, they’re behind even though financial industry has been so much faster to move with predictive analytics and all these different technologies we have available. But the truth is that the healthcare companies just don’t want to maybe invest the money into staffing a call center with full time employees because that’s more expensive.

And I guess the theme here is pitching something or standing behind something for reasons that are not actually the real ones. And when companies come out and say, hey actually operationally, we’re really struggling with this. There is a demand that we are not able to fill. And it’s about our margin and just this honesty is something that I’m trying to bring back this radical sense of honesty with my clients. It’s my job it’s what they pay me for and that is not the way most of corporate America conducts business. And so some of the smarter companies are beginning to do that more.

I think even a really great example is the way that Lyft and Uber have drawn this very direct parallel. I think they offer in many ways the same thing but their point of view is so different. So things like that I think are really starting to illustrate in a very tangible way. Wow Lyft, when I think of Lyft, I think much more values driven I think that there’s still some challenges there. But I think that if you’re contrasting against Uber who’s playing sort of that–you know they’re a rebel in a very different way by not considering the implications that they might bring twisted either to saying we’ll see us and we’ll figure it out later. That’s a good example I think of standing behind values. With just saying, no we want to work together, we want to figure out how this can work for the long term.

Audrea Fink: [00:08:40] That parallel between those two is really fascinating too because they are. They are taking their own risks in that right. Lyft is risking the clients or contacts who don’t align with their value system, and Uber is risking theirs. So it’s an interesting balance.

I read this article in Inc.: What Successful People Know About Taking Calculated Risks. And in the article the author talks about balancing that feeling of fear versus the actual weight of risk. So sometimes like with public speaking, we fear it more than the risk warrants. But then we tend to fear some things like driving your car with less fear than statistically speaking that should warrant. Right? It’s more dangerous to drive a car than to speak publicly. Can you tell us about how you balance that fear versus risk equation and then share some tactics we can take when looking to judge that ratio fairly?

Caroline Garry: [00:09:40] Again these are such great questions. I mentioned this earlier so I’d like to touch on it and dive a little bit deeper. It really does start with trust. You know I think at the end of the day you can really know about yourself when you’re doing something that is negligent or if you’re–you know I call it betting against myself. And I think the bigger thing is to start small. You don’t have to make a really giant choice about a risk quickly. You know you can workshop it with friends and colleagues and a lot of self reflection.

But even before that, I do want to mention something that I thought was really brilliant that Audrea mentioned the other day as we were meeting for our leadership group: which is that I was able to take a really calculated risk in starting my own business which I’d like to share a personal story about that. Because I knew that if I failed I had a safety net to fall on. Which was that at that time I was married and I did not have I have a son, he’s two and a half, I did not have a child yet. And so when I was weighing these different possible outcomes not being tied to any of them I knew that the worst case was that I was a hot mess and I failed and that I would need to know when to tell myself this isn’t working and that I could just find another full time job.

If I had been single I’m not sure that I would have done this. I think I could have. Which is the interesting thing but I don’t know that in making this calculation that it would have felt safe enough because the other part of my mind really likes the idea of safety and security. As we all do. We’ve got to pay for food, we’ve got to pay for rent, we’ve got to pay for all the many things just to exist, and health insurance is a big one and so, I want to acknowledge that because I feel like it was it was definitely from a place of privilege that I was able to do this at all. So I think it would be wrong not to acknowledge that because that was honestly the very first of a decision tree was that I could. And so that’s something that I think can be really challenging when you’re thinking about, oh chase your dreams and sometimes in–that would be a really–it’s a lovely thing to say that, but it’s not always possible.

Julie Holton: [00:12:02] That is such a great point and I can relate personally to that Caroline because I also have my own business. You know it’s interesting though because I think sometimes we put our own limitations on ourselves, and whether that’s right or wrong it’s part of our risk assessment of our own personal lives.

And so when I started my business; I’m single [not married] and so I don’t have a partner, but I looked at it like I don’t have someone else who’s counting on me. I don’t have any dependents, I don’t have anyone who–you know of course I need my salary, I need to pay my own bills, but I felt a little more secure in saying, okay I’m taking this risk for myself, I’m not making this choice for other people. But I think one thing that really struck me–and I bring this up for anyone out there who might be considering starting their own business or someone who might be just starting down that path: We often think of our jobs as being secure when they’re not. And we also–we often forget that we’re relying on that boss or relying on the financial well-being of that company, the stability for us to keep those positions, those jobs, things that we have absolutely no control over and often no insight into depending on what our positions are. And so I think sometimes people often create their own false sense of security. So it’s just something that as we’re weighing these risks and if you’re going to start your own business, or if you’re going to make a career change, or any kind of move in life, to just really think about the facts like that big picture.

Audrea Fink: [00:13:35] That’s a really great point. I love the idea of maybe where you’re at, you know, at a big company is not really safe and secure. And maybe there is some security in running your own business and so that’s a brilliant way to look at the calculated risks involved in that.

Caroline can you just talk to us a little bit about the shift that you made, where you were working before what you were doing and then the shift to building your own business and talk to us a little bit about what you left behind and what you gained?

Caroline Garry: [00:14:06] Yeah, I had the great honor, is really the right word, of working for a couple of incredible really strong female entrepreneurs that were models for me. My dad was an entrepreneur too, but it was different seeing a woman doing it. It was just different because my mom was a stay at home mom. I had never seen women be like this. It dramatically impacted the way that I show up at meetings and the way I feel like I have contributions to make and modeling myself after them was one of the best things that I think that I ever did because I started working for these women when I was in my mid 20s.

One of them, her name is Kat Jones. She is a dear friend and mentor and I had never seen anyone work like her before and I wanted to be just like her. She gave direct access to her employees for the risks that she took. Every year we had this really great company meeting called the Summit, and she would show us financials; she would show us the bizdev opportunities on the horizon and what it takes to land things like this; how we qualify clients, what this means operationally for our team, and for resourcing and really, really open about these things, and I don’t think I would have had any idea what it would take to run a business had it not been for her ability to bring everyone in behind the curtain. A lot of leaders don’t do that.

It’s maybe a select group of three, five, 10 depending on how large the company is–at this time, her business, we had about 30 employees so it wasn’t tiny. And she really wanted everyone to understand that their jobs all contributed to the success of the business. So she inspired a shared vision which was one of our Leaders of Tomorrow principles so I think about that and she really did well on that.

I had a second boss; many years later I ended up moving from Austin which is where I worked for Kat Jones at Milkshake. I moved to Houston and I moved there because my husband had been asked to move there for his work and it was a lot, it brought a lot of change with it. I’d been on this career path–it was before a lot of people began to work remotely and so my opportunities were a little different. I needed to switch jobs. I actually ended up working for Milkshake remotely for a while because I realized that I could ask–and after that though, there became a time where I was ready for something new and I worked for another company called Langrand and–the owner, her name is Shannon Langrand–similarly really shows what it means to bring it.Like in business as a female, and I wanted to do that too.

At some point I thought like I love these women and I love everything that I’ve learned and I think part of what they’re teaching me is that I can do this, right? Like part of the reason that they’re showing me these things and part of the reason that they’re talking with me about financials and especially transparency around cost is a huge thing I think for leadership to show because of a lot of the reasons that you mentioned earlier. A lot of times employees are really separated from the numbers and on purpose. And I think in many ways they were mentoring myself and several others to prepare us for something that they saw on us that was reminiscent of what they used to be like before they started on their own journeys. And we never had an explicit conversation about this though, it just sort of started boiling in my body.

And the reason that I started my own business is because I was working a more agency style job, and the hours are pretty intense. It’s long days and everybody who’s in it is expecting that. We know what we’ve signed up for, it’s part of the job. But I wanted to volunteer a lot more in my community and specifically I wanted to go to to Houston City Council meetings and show up for that and those were at 2 o’clock in the afternoon. I couldn’t do that from a regular job.

Audrea Fink: [00:18:06] Yeah.

Caroline Garry: [00:18:07] And so it brought up a lot of conflicting feelings and eventually I just said like I don’t know I feel drawn to support my community I’ve got to do this I can’t do this from a regular job I’m leaving the company. And I can’t believe in some ways that I did that now because I was leaving to follow passions that were around community. But I know now that it’s because community is a really important thing that I use as a metric to qualify my own clients. And so I was actually headed toward not just wanting to volunteer; I was headed toward this entire space that I wanted to commit myself and my business to supporting these values, right? So a lot of my work is around things like access to health care. Things like building community through engagement around issues. And it’s not really a traditional advertising route where you do, you know, product marketing or things like that I’ve got actually the direct opposite from that. So I took this risk because I’d had really great models in other leaders that showed me what it looked like.

Audrea Fink: [00:19:15] Well it sounds like not only did you take a risk in shifting from maybe more stable–although it sounds like we’ve already discussed how it’s more stable is maybe an illusion. So you took this role; you left a role to go to your own business, but then even your own business style was different and so in its own way its own calculated risk to not necessarily just do the normal or the usual or the expected.

Caroline Garry: [00:19:43] That’s right. I have a degree in graphic design. Like that’s what I went to school for and that is a part of what I’m doing now but it’s only a tiny part. So I always joke with people and I have an incredible amount of respect for folks who have real MBA. I don’t have one. Running my business is my MBA and it is gosh it is not wrong but it’s kind of close to that because there are real risks here it’s not even just academic. Like it’s actually happening.

And so what happened was I noticed in, for example, pricing out large scopes of work, that those are huge clients. Right? You have budgets of a million dollars. And on the other hand you’ve got the opportunity as a graphic designer to do gig-based work, freelancing. And that doesn’t feel right to me–freelancers. Now I don’t feel like that’s what I’m doing. And there’s this giant space in-between the idea of these million dollar budgets and freelancing. And to me that’s an opportunity and I think that’s a really large part of calculated risks is by not saying “oh I’ve got to play here where everybody else is” but saying “well where’s the empty space where I can really go in and make a difference?” Like that’s my opportunity. And that’s what I saw.

And so I thought gosh I think there are a lot of really great organizations or maybe I don’t have a million dollars but maybe they’ve got a budget somewhere between ten thousand and seventy five thousand. We can work with that. And so I think that was–I was really proud when that was one of my first light bulb moments was thinking, “Gosh I think there’s actually an incredible amount of business there and it would be truly mutually beneficial.”

It’s my job to every client to say like, truly, what’s your budget. I’m never going to exploit that. And so again we started from a place with trust. They can count on me to tell them, “Look you told me you’ve got fifteen thousand dollars I think we can do it for seventy five. Seventy five hundred dollars, that’s it.” I have a lot of pride in building a reputation that is understanding of the risks on both sides. Because I know that a company who’s got fifteen thousand dollars, for example, if we’ve built trust that’s what they have. And they’re making a bet on me to be able to deliver them what they need. And I want to pay it forward by saying I’m gonna be really honest with you and I’m gonna take a risk of not capturing a greater margin right. I could do the work for 15 grand and knowing that it’s going to cost seventy five hundred and walk away with a margin of seventy five hundred, but I wouldn’t feel right about that. And I think in the end they would know and customer retention and building loyalty and some of the things that we talked about earlier those are real things. Those are not fake things like the buzz words around authenticity, it’s lived. So that’s a big thing for me.

But I never thought that I would find myself doing the purchasing, expenses, invoicing, budgeting, you know profit and loss reports. And I was told actually like you should probably call that like a PNL. And I was like I don’t know like, all I know is that I’m living this every day and that it’s working. And I think I’m trying to do it right. But I’m trying to do it right by taking a lot of calculated risks. Which is sometimes a project might not be fit for me, or maybe operationally I can’t support it in the way that I need to to do it right. And so saying no to those things is really hard because you think oh but I really could do it I want to do this, and you can’t really build the airplane while it’s flying.

Julie Holton: [00:23:10] And let’s be real. The authenticity that you’re talking about, that you’re describing, it’s not to say that it doesn’t exist with the big ad agencies or with the really big competitors that would capture that full budget. I mean of course it exists on that level. But the way you’re describing it, it really sets you apart. And I think it sets people like us apart whether we’re business owners or whoever we are in our position. It really is, it’s something that right now with all of the challenges going on and all of the social responses that we’re seeing online with these various movements–I think that it’s something that people are hungry for.

They want the authenticity. They want the brand that they can trust. And when you can sit down with and develop that relationship it just shows that you’re someone that they want to work with on every level. But talk to a little bit about the sacrifices that it takes to get to that point because there are things that I’m sure you’re giving up to be the authentic person and just stay true to your personal values in your business. Can you talk about that a little bit?

Caroline Garry: [00:24:21] I can. I’m trying to play the long game is the best way that I could put it. But it’s been really hard especially, I mentioned earlier I’ve got a two and a half year old, and it’s a lot. And I think gosh like this was a pretty wild thing to start with a small child. I do a bit of travel for business and I’ve got to show up one hundred and fifty bajillion percent. I don’t have employees yet. That’s something that I’m thinking about doing potentially next year. I’m at a crossroads right now; I either need to grow and build a support staff to support me because I’ve right now I’ve reached a ceiling in my day which is amazing, and I absolutely try not to be frustrated by that because if I could go back and tell myself three years ago when I started my company that this was my future I would be so proud that this is my problem now it’s not, “Oh my gosh can I find a client?” So that’s–I tried to I think if we could be entrepreneurs and remember our first days, you could keep a little bit of that like zest and zeal because our palate for risk changes dramatically when we have something to lose.

You’re holding on to what you have instead of being willing to try for what you don’t have, and that’s just a mindset that is hard to remember. I think for me the biggest risk has been, and can I be a great mom? Because I’m the daughter of an entrepreneur and my dad was not around much. And you know he wasn’t really like a–he wasn’t like a dad kind of a dad, anyway. But I saw that. I remember that and I really want for my son, for him to think that what I’m doing is awesome and that I’m around.

And the other day I’d like to share a caveat. He said, “Mama you be the baby. I’ll be the mama.” And then he comes to me and he says, “Baby, mama’s go into a meeting but I’ll be back.” And I thought oh my gosh this is amazing, my son sees his mom work and is proud of that. He said Baby–because I was being the baby–He said, “Baby I’m going to a meeting but I’m going to be back.” And I thought Great. Like not only–because he’s two and a half and so the fear of me leaving and not coming back is a really real thing when you’re you know nurturing a young mind and I love that he knew that both I was going to meeting and that I would be back.

So that–the fear there though of negatively impacting my child and having him know that he matters and that I’m working both on my goals and for him; the balance there is something that I’m learning every day: how to do that and what that means for me, and what that means for when I need to say no or what my limits are. It’s been a challenge for sure.

Audrea Fink: [00:27:13] I think that’s a really beautiful story. Thank you so much for sharing it. We actually talked a little bit about this story in our happy hour and I think it’s a common fear women have about not being there for their families but also it’s a way I think it’s the new normal is women are working and it’s important I think for us to see that we can–I don’t want to say I want to say find the balance, because I think that’s bull–no one asks men how they find balance. But I think that is a good example of how you you show up living your values and also working your values. So it’s a good balance you found how to make that work.

So what are some of the questions, as you’re looking at the risks you’re going to be taking, what are some questions you ask yourself to assess risk whether it’s worth it? Can I go to this meeting and still show up for my kid? Can I go to this meeting and still live my values? How do you how do you make those assessments? What are the questions that we can ask ourselves if we’re looking to make those decisions as well?

Caroline Garry: [00:28:19] Gosh. Well I’ll tell you that the things that I ask myself are very different than the advice I give my clients and so I’d like to do some reflecting on that later to think about, gosh, like why do I have different criteria for my clients? They’re probably struggling with the same things I am. For me, it manifests a lot in my ability to say no because I think aside from being a great parent and aside from large financial risk. Right? Like our livelihood. My biggest fear is around again like losing something that I’ve worked so hard to gain and so, a lot of times that would be something like, OK if I say no to this opportunity, if I say no to a client maybe even a client that I’ve had for a really long time–because I love to be the hero for my clients. It’s one of my favorite things. I love to show up as a trusted adviser and I love to help them reach their outcomes. That’s–that is what I do.

My business model is one that is built around customer intimacy. I am super passionate about that. And I mean it. And in a genuine way, which is that they have access to me, they can call me on the phone, I’m not even going to bill them for it. I really want to show up as a partner, not as a vendor. And so we built a relationship and so, funny enough though after building this relationship some of them, you know, multi-year–I’m always afraid to say no because I’m terrified of letting someone down. Because at this point it’s not transactional to me, they are–I’m in it with them and saying no feels very risky. It feels risky in a couple of ways, one being, are they going to begin thinking of me like I’m not on their team if I say no? And also the possibility that they might take their business elsewhere. That feels like a giant risk too. And so that’s something that I am constantly battling with myself about, OK if I say yes to this what does that mean for maybe my evening, or my family life, or sacrificing or de-prioritizing another job?

You know those are a lot of choices that you have to make. You know what falls below the line? I guess is what I would say versus what falls above the line. Those are challenging choices and a lot of times, it’s hard when you’re a customer intimacy focused business of one to make choices that are putting something above or below a line because they’re all important. And my clients you know they’re not large conglomerates. They’re businesses that are not too dissimilar from mine and each one of them is important, is the truth. But it comes down to what can I reasonably do in a day. So that’s a large question I ask myself is, if I say no what could happen? And if I say yes what could happen? You know good and bad; sometimes saying yes means bad for me or vice versa. You know, it’s a bit messy and one of the big things that I love that I borrowed from one of my mentors I mentioned earlier from Shannon, she says this all the time embracing ambiguity and I think that that’s amazing. And I think when I started to do that, to truly embrace ambiguity it allowed for honestly like having some fun in the hot mess of running a small business. Here it is like I don’t know, but I’m trying my absolute best and I’m not gonna be tied to perfect. So that’s a big one for me too.

I know Audrea knows I have OCD–the real kind. And perfection is really woven into that and so there is a risk of that too and saying gosh like what does it feel like to–is getting my 80 percent actually. You know maybe some other relative you know maybe it’s more like a hundred 20 percent for somebody else. My husband jokes with me about that a lot and I’m learning how to do that. It’s funny though because for other, you know, for businesses, my advisement would be super different. Right? It would be things like: market sizing, and competitive analysis, and did you take a look at forecasting, and trend, and what’s your cash flow situation, like or gosh like how much is it going to cost to build this MVP if it’s like a tech platform or a startup? And those are so different right? They’re so business-y. And a lot of times at the end of the day like somebody is just scared.

Audrea Fink: [00:32:31] I think though that those can go back to your question of what happens if I say yes versus what happens if I say no. I think if you’re looking at you know competitive analysis or areas of opportunity, what happens if you say yes to investing here? What does that mean? Well it could mean you lose that investment. But what happens if you say no? Well it could mean you lose that opportunity. So I don’t think they’re so dissimilar.

My boss on a pretty regular basis says “don’t let perfect be the enemy of good enough or enemy of getting it done.” And so a lot of times I do think, “Well I want this to be perfect.” All right. You know I work with attorneys and that competes on challenge and so I want them to see that this is perfect. And so it will take me a really long time to get something done or I just won’t be able to move the ball forward because it’s not there yet and it defeats the purpose, like it’s not productive. Whereas if I got it good enough, the worst thing that happens is that they correct the mistakes. Which is what it means to work on a team anyway. So that risk is I guess in a lot of ways not real. It’s sort of what’s in your own mind. But I think you could apply it to business as well, right? There’s an opportunity cost for everything. Are you willing to say yes? And if so what does that look like? Are you willing to say no? And if so what does that look like? Right? There’s there’s risks on both sides.

Julie Holton: [00:33:58] And I’m going to sound like a broken record throughout this podcast but I think it all comes back to you staying authentic to your business values. So you’re not saying no to clients because you don’t feel like doing the work or you want to take an extra vacation next month, like you are saying no because you want to preserve that value. And I can understand that so well. My team actually this summer; I took about four to six month four to six week break of taking on new clients because we hit a wall. We were at capacity and I was lying awake at night thinking of how were we going to get everything done? And how was I continuing to build my team and support my team when all I was doing was just giving them more and more work? And I really started to worry about the quality versus the quantity, because for us it’s always been about, it doesn’t matter how many clients we have, we’re doing our very best for you. Like you talked about like one hundred and twenty percent for every single client. Well at some point those numbers add up. Yeah. And so there just–there aren’t enough hours in the day; there aren’t enough people on the team. And so we just I said OK I have to hit pause because I have to protect my team. I have to protect our values and what matters to us. And I have to protect the clients that we already have.

Audrea Fink: [00:35:19] And you have to protect yourself and your own mental health and emotional stability.

Caroline Garry: [00:35:24] And Audrea knows absolutely!

Julie Holton: [00:35:28] Because it comes down to what? Like you said, Caroline, what happens if you say yes versus if you say no? And the other thing I like that you touched on is the transparency: having these conversations where the client needs something or is asking for something and you sit down and you look at OK: What is this timeline? What does that look like? Maybe you’re not actually saying no, which I’m sure comes really easy for your two and a half year old, but really hard for us as adult business owners: the saying No. But what are you really saying no? Or Are you looking further down the timeline? Are you looking at, you know, because I’m sure your problem solving and you’re figuring out other ways to say I need more time or I’m that my capacity.

Caroline Garry: [00:36:12] This, gosh, there’s so much here in all of this. I’d also love to know if there’s a book, “How to Say No,” like I say no to my 2-year old. If there’s not there should be!

Julie Holton: [00:36:23] There is! My boyfriend bought it for me. I will put it in the notes of the podcast because I cannot remember the name of it off the top of my head. Although I swear I read it, right? No actually, he just bought me a book, but it’s all about the art of saying no. And it’s just about this, you’re not actually saying no, but you’re having to work through that transparency and that authenticity and it’s the self preservation.

Caroline Garry: [00:36:46] Absolutely. And oddly enough like saying no can really help with my own brand positioning, which is one of high value, customer intimacy, you know, showing up as an adviser. And when work has to be done so quickly or maybe I’m at a–you know, I’ve reached a ceiling–I don’t want to do work that feels transactional, that is exactly the opposite of what I’m trying to build. I run into a lot of these operational stressors exactly like you’ve described when it comes to being at capacity. So on the one hand saying no is necessary, and limiting to what I can reasonably do and do it right within a certain time. On the other hand that’s fighting against that another risk that I calculate is this [VizDub] and what’s that work funnel. What’s the long term what work to have projected over the next quarter or two? Because I am one hundred percent responsible for that.

That is how my business makes it or breaks it, and I’ll be honest I’ve invested a lot more in retention strategies than I have even finding new biz. I think it’s so much more expensive and so much more time consuming to go out and find new biz. On the other hand, I do spend a bit of time contributing to our piece. And that’s a huge lift! It can be hours and hours and hours of work that may or may not pay off. And those are some of those more calculated risks that are truly coming down to what’s the possible payoff of this? If I think operationally I can support that.

Audrea Fink: [00:38:16] So one of the things that I coach my attorneys on is that 80 percent of your work should be coming from clients you already have.  80 percent of your time should be devoted to getting work from clients you have, 20 percent or less should be devoted to landing new clients because the more you service the clients that you have the better service you’re able to offer, the more likely they’re going to come back, and it is cheaper for you and beneficial for them because then it’s long term.

When you spend your business development efforts chasing the new, you spend a lot of time chasing opportunities that won’t come to fruition simply because they take time and you spend a lot of time that you could be spending reinvesting in people who already believe in you, who already buy into what you’re offering, and who already see value in you. So I think that is a very smart calculated risk. You still need to get new clients especially as a new business. New is required, and you can’t exist forever if you’re not looking out for new. But if you are not spending the majority of your time making sure that the clients that you have that are good quality clients (clients you want to keep) are not bringing in more work, then I think you’re making a poor risk.

Caroline Garry: [00:39:27] I could not agree more I feel the same way and I thought a lot about that this year because I do continue to go after new work and I’m at a transition right now where I’m deciding–I’m weighing the risks of what does it look like for me to bring on, for example a full time employee or two and continue to win more work and to be able to have the support staff to really you know create deliverables that are that full value?

I would never sacrifice a level of work that would go against everything that I’m doing. That’s one route; the other direction that I’m considering going is winning new work and keeping up–absolutely keeping that 80 percent. I could not agree with you more. It’s exactly the way that I like to work. So what I do win new clients, and I support them! And if I can’t, maybe I need to reconsider qualifying clients. Maybe there are some old clients that don’t fit where I’m headed and it’s a growing pains thing.

And again if I could go back and talk to myself a few years ago and say look these are the decisions that you’re going to be weighing in a few years, there is nothing to do but to celebrate that. So while I feel a little bit stressed out about which way am I going to go, it’s really great to be able to ask myself that question.

Julie Holton: [00:40:35] We’re talking to Caroline Garry who owns a brand strategy visual design and customer experience consultancy. Caroline for our listeners today, if we want to flex those calculated risk muscles, what are some everyday ways that our listeners can start right now practicing taking some of these calculated risks?

Caroline Garry: [00:40:54] Well for starters you could speak on a podcast.

Julie Holton: [00:40:58] Like Think Tank of Three!

Audrea Fink: [00:41:00] Thanks for joining us!

Caroline Garry: [00:41:03] That’s right. Seriously it’s a great way to exercise and flex that muscle. You could begin telling people things about yourself that maybe you’ve been hiding or harboring, for me personally this year I’ve talked a lot about being a business leader and having my own mental health issues like OCD and anxiety. That’s a risk I think more and more people are doing and it would be cool to be part of that movement together.

Honestly stuff like what if you go to a restaurant and let’s say that you don’t have a crazy food allergy and you’re not going end up at the E.R., like–order that wild thing off the menu that you kind of want to do, but, “Oh I always get this–” like, just see how it feels! Try it on and like what was the outcome? What’s the worst that could happen? You know you order something different or you’re a little hungry afterward.

And that sounds really silly, but if you think about it, anytime that you’re doing something slightly outside of your norm I think that’s great. So you know, it could be anything from travel, to reading books about subjects that you really don’t know much about, and you’re slowly becoming a subject matter expert. You know stuff like that, that’s just–nothing dramatic.

You know, again you always can trust yourself not to be negligent, though I do think a lot about high dives, right, like the Olympic high divers. I think, oh my gosh like there had to be a first time that they actually like drove into the pool! How freaky would that be? And it occurred to me that they learned to really trust their body; that they had done a series of repetitive motions; and you know again, trust is probably my biggest thing, that I would offer is that you know yourself and you’re not going to order something off the menu that’s going to make you feel sick. You know, there’s a limit there I think of what we can all shoulder. But yeah I think a lot about things like that. There was a first time that we drove a car and the trust that maybe our parent or teacher had in us to do that is pretty incredible. So again, you know coming back to trust.

Audrea Fink: [00:43:00] This has been so insightful. Thank you so much for joining us today to share your thoughts. Before we go though, we are collecting advice from successful women in our communities and sharing it with our Think Tank forum. So we have three rapid fire questions for you. Are you ready?

Caroline Garry: [00:43:16] Yes.

Audrea Fink: [00:43:17] Is there a lesson that you’ve recently learned that you wish you would have learned earlier in your career?

Caroline Garry: [00:43:22] The power of no! I think about what you know what would a guy do? They would definitely just say no if they needed to and also to like you know go after jobs that are one or two levels of what you think you are. Because it is very likely that you’re already doing those things. Those would be the two things that I would go back and tell myself that I really feel like I’ve only come to understand over the last five years and I’m in my mid to late 30s. So it took a while.

Julie Holton: [00:43:52] So along those lines what advice would you offer to your younger self, maybe, say 10 years ago?

Caroline Garry: [00:43:59] I would say go after your own goals, right? Like that it’s OK to go after my own goals; I don’t have to live out someone else’s dream for me or be exactly what, you know, somebody thinks that I should be, whether it’s an employer, parent, or whomever; just go after your own goals.

Audrea Fink: [00:44:18] All right last one. What do you think the most important skill to hone for a woman is in today’s professional setting?

Caroline Garry: [00:44:24] I think there’s a sense from women that we’re still questioning whether we should be at the table, and what does that look like and what does that mean? And can we show up as a guy would? I have to say like I think the answer should be yes. I think that’s a really important skill to know that you do in fact deserve to be there. And I also think an important skill for women is we feel the need to validate ourselves a lot. And so I always think about it like this especially when I’m discussing budget: write the number on a paper, put it on the table, slide it across and then, zip it. Don’t talk myself down on the behalf of someone else. You know that’s something that I think is really hard to do, because we’re wondering what we’re worth and we shouldn’t. We are worth exactly what we think we are, probably actually more.

Julie Holton: [00:45:13] Thank you so much Caroline, can you share the best way for our audience to connect with you if they have more questions or if they want to talk business with you?

Caroline Garry: [00:45:21] Of course I would love that. They can always find me at it’s c a r o l i n e g a r r y dot com, or you can email me and you can access me directly at by email.

Julie Holton: [00:45:37] Caroline Garry thank you so much for joining us today. That is all for this episode of Think Tank of Three. Connect with us and our guests online. We blog once a week. Subscribe and you’ll get an email when we have a new podcast or a blog. And also make sure to find us on social media: Facebook, Instagram, LinkedIn, Twitter. We also have a private group on Facebook where we can all give and get advice freely. Look for the group on our Facebook page, and if you like what you heard in this podcast, share it. You can find the podcast on iTunes, Spotify, Stitcher, and SoundCloud and of course, if you have questions or topics you’d like to discuss, send us a message at

[00:46:22] [OUTRO]