August 23, 2022

A Solopreneur’s First Imperfect Step with Claire Gallagher

by Hacker Valley Studio

Show Notes

Claire Gallagher, Designer and Solopreneur Strategist, comes to Hacker Valley to break down branding, visibility, and choosing solopreneurship over business ownership. Combining the terms solo and entrepreneur, solopreneurs are a different breed of business owner, and Claire has made it her mission to help them not make the same business mistakes she once made. Claire walks through the essentials of how her business caters to individuals looking to go it alone and how to make an impact while staying small. 

Timecoded Guide:

[00:00] Introducing the concept of solopreneurship

[04:32] Shifting to business strategy to better serve a client base

[09:19] Deciding alone as a solo entrepreneur

[16:40] Pricing your work and validating your professional value

[24:46] Making peace with looking silly as a business owner


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Why did you choose to go down a path of catering to solopreneurs, versus working with enterprises or small and medium businesses?

Claire has dabbled in building teams and working in larger businesses in the past, but her calling has always brought her back to a company of one. For solopreneurs, Claire explains, it’s not that they cannot afford hiring employees or scaling their business. Instead, a solopreneur’s focus is on the balance between work and life, along with the power and experience to make their own decisions about their business. 

“I'm a loud introvert. I could talk all day, but essentially, I'm kind of introverted in secret. Generally, I like to work alone, to get into a creative flow, to not have anybody to answer to. This company of one, this solopreneurship, it suits my energy and my temperament.”


What are some of the pros and cons of going it alone as a solopreneur and keeping your business small? 

There are pros and cons in business, no matter the size. Claire’s strongest pro for becoming a solo entrepreneur has been her ability to pivot without impacting anyone but herself. Pivoting towards strategy was a hard decision, but it was so much easier to make on her own. Unfortunately, making decisions on one’s own can also be a con of solopreneurship. Claire has seen clients have a lack of accountability in sticking with their decisions when they don’t have anyone working with them.

“That's a pro, I was able to pivot without having to hire people, sack people, and really invest heavily in changing everything. That's a real plus, I could just pivot like that and it was a decision that I made, and I was responsible for it.” 


At what point would you recommend a solopreneur, or content creator, to reach out to someone like you so they could shine in this digital world?

Although solo entrepreneurs thrive in business on their own, it’s important to never go it alone. Claire advises that early stage solopreneurs consider the community around them and build their business with a healthy curiosity in books, online resources, and virtual communities of fellow entrepreneurs. As they progress through their business, Claire also recommends connecting with a coach or strategist, like herself, to go further faster and avoid careless mistakes.

“Solopreneurs think, ‘I'm smart, I can figure this out.’ Yes, you can, but to go further faster, I think you need to work with a mentor or a coach or strategist. You're always going to get further faster by finding somebody who understands what you're trying to achieve.”


What are some of the tenants that you teach people about coming across as authentically as possible?

Branding is a vital element of content creation and business ownership. However, the current world craves branding that comes across as authentic. Claire explains that authenticity comes from a willingness to make mistakes and put yourself out there, even if it feels or looks silly the first time. If a solopreneur is honestly trying to deliver value, that will show through any first-time awkwardness or silliness and still feel authentic to potential clients.

“Starting before you feel ready is really the only way that you can start because you can't know everything until you've tried some stuff. Showing up and making mistakes and maybe seeming a little bit foolish at the start, take it. That's what's gonna happen.”



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Hacker Valley Studio 00:07
Who says tech can't be human?
Claire 00:10
Sales strategy saved my business. Like, really knowing how to get people on calls is the first thing and then, on that call, allow your potential client the space to express their need, so that you know what you need to speak to.
Hacker Valley Studio 00:30
Welcome to the Hacker Valley Studio podcast.
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Chris 01:04
What's going on, everybody? You are in the Hacker Valley Studio with your hosts, Ron and Chris.
Ron 01:17
Yes, sir.
Chris 01:21
Welcome back to the show.
Ron 01:24
Glad to be back again. It feels refreshing to always have a new guest, and a guest that we haven't spoken to before. This episode, our guest is Claire Gallagher. Claire is a designer, strategist, mom of two, and someone that's dedicated to helping solopreneurs, like Chris and myself with design and strategy and so much more. I'm excited to jump into this conversation. Claire, welcome to the podcast.
Claire 01:51
Hi, guys. I absolutely love your intro. It just so hypnotic, you just kind of get into the groove, get into the mood, and ready to podcast.
Chris 02:00
Yeah, you know, we debated on whether to cut the intro for many, many years at this point, but we just kept it because it gets us ready, it gets the guest jazzed up. We are beyond excited to have you on because there's a lot we want to ask you about when it comes to solopreneurs, and even just branding and visibility out there in the world, because there's a lot going on. But for the folks out there that don't know who you are just yet, we'd love to hear a little bit about your background and what you're doing today.
Claire 02:25
Oh, well, that's a really, really, really, I mean, how long do you have? So, I basically started out as a graphic designer, I grew up looking at, you know the Sergeant Pepper's album cover, that famous one with all the people lined up from the Beatles? I lived with that, and it was basically a member of our family. I thought, I want to do that. So, I wanted to be a graphic designer, and that's what I became. As graphic design is one of these great international skills, I traveled the world with it, I lived in Dublin, London, Paris, Melbourne, all over the place with it, finally settling in Paris. That's where I started my family. And once one has a family, that design agency lifestyle is a bit of a stretch when you have to get home and leave at a certain time. So, that's kind of the moment when I took it on my own back and made a business out of it for myself. So, previously, I was always in agencies and really loved that design and communications agency buzz, but you know, sometimes deadlines are real tight and you have to stay there till midnight, and maybe come in on the weekend. I figured, when we started our
family, that wasn't really going to fly. I always kind of wanted the kind of energy of having my own business, and that's what I did. I started back in 2012, officially, and made all those mistakes, all of the mistakes that are to be made when you have your own business, I made them. And now, I help people to avoid those mistakes.
Chris 04:00
The thing that stood out to me going through the content that you create, and the things you've done for other folks, is this term visibility. Because when you talk about visibility, obviously initially you think graphic design, you think about what things look like, you think about awareness. Where did that transition really come in? You go from being the person that's really focused on the graphics and the look at things, but then this broader concept of visibility and standing out amongst the sea of others? Where did that transition really come in for you and how has it been since?
Claire 04:32
That's such a great question, because creating designs for people, it's flat. There's no life in it. The whole reason to have these assets, these visuals, these designs is to communicate with somebody else that's hoping to find a service or a product like yours. So, the design part of it was always something that I was really excited about. When you're working in a big agency, you've got somebody to do the marketing strategy, somebody to do the copy, somebody to plan how this is going to be distributed, but when I was working for small businesses, they liked a website, and they wanted me to copy it, or they liked the logo and they wanted me to do something like it. Or, they'd have their own idea, and they'd want me to create it. I was always taking those orders and doing a good job and making everybody happy, but then I'd keep in touch with my clients and say, "How's it going? How did that go with that logo and everything?" And they'd say, "Oh, we really still haven't used it. We got a bit nervous about putting it online," which is understandable. Showing up can feel a little bit scary for people, especially in the very early stages of business. So, I thought, hmm, there's something missing
here. I'm not serving people in as valuable way as I probably could. So, I really started to get myself interested in strategy, and that is: What is the role of design in the bigger ecosystem of their marketing thing? So, having things look right, it's all well and good, but if nobody gets to see it, it's kind of pointless. I got really into it, I did B school, I've done a number of the future courses with Chris Doe, and I've always just been reading, reading, reading and consuming as much as I could about how to show up, and when somebody finds out about you. What else can you offer them? How can you build trust? How can you get somebody on a call? When you're on that call, what needs to happen? And then, there's a whole part of serving your clients, so this is kind of getting a bit meta now, but I was learning it for myself as a business owner, and then I created a number of different services, to help people to do that for their business. So, having something look nice is one thing, but having it on rails, so it can go and meet the people, and go and actually serve your business as a really vital thing to bring in clients
Ron 06:52
I love that. I mean, that's so important, especially for someone that is this concept of solopreneur. And for anyone that doesn't know, a solopreneur in my mind, and I would love to hear your explanation of it also, Claire, a solopreneur is someone that is a founder, but they're also an employee of their company. A lot of times, when you hear about an entrepreneur, they're not necessarily the ones that are in the weeds, maybe doing the marketing, doing the design, and also doing the customer engagement and outreach, and maintaining a great relationship. It sounds like you've really honed in on your company of catering to solopreneurs. I would love to hear why you chose to go down that path, versus working with enterprises or small and medium businesses.
Claire 07:37
Well, solopreneur, really, it's a solo entrepreneur, I guess. It's squishing those two words together. Solo is not to say they're just starting out, and it's just them. Some people, like me, they're solopreneurs by choice, they're not looking to scale to a team. They're not looking to build an empire. There's a great book by Paul Jarvis called Company of One, and he says that staying small is the next big thing. I mean, I have dabbled with building a team in the past. I have dabbled with having an associate model with freelancers and everything. I do sometimes recruit freelancers, but I never wanted to be responsible for somebody else's salary. I wanted to be able to just go, "Okay, I'm taking the entire summer off," and be able to do that. Now, if you were doing that with a big agency and a big team, you have to really make sure that your cash flow and your business has enough money coming in to pay all of your staff. I never wanted that pressure on my back. I'm a loud introvert. I could talk all day, but essentially, I'm kind of introverted in secret. Generally I like to work alone, to get into a creative flow, to
not have anybody to answer to in terms of, I need to give them work or delegate. This company of one, this solopreneurship, it suits my energy and my temperament. It's not that I'm not getting big enough and I can't afford to have a team, it's that I know what enough is and I know that the balance between work and life is more important to me than anything else really.
Chris 09:19
I love that you're talking about the freedom to do what is in your mind or in your vision, because you're ight, when you deal with larger companies, it's very difficult to change course or try something new. I bet there's a bunch of pros and cons of going it alone or keeping it small, versus trying to scale and make it large. What are some of the pros and cons from a standing out perspective that you have found in your work?
Claire 09:44
That's an interesting question, because I mean, it's like if you're a more established brand or a more established entrepreneur, with teams, with people working for you, and I didn't want to kind of undermine that in any way. I think if that's your thing, absolutely go for it and good luck. But one of the pros for sure is, for example, I pivoted away from brand and web design into mostly strategy. I help people with their whole plan around how they show up online. That's a pro, I was able to pivot without having to hire people, sack people, and really invest heavily in changing everything. I just decided, when I turned 40 last summer, that I didn't want to be doing only that, I wanted to really do the strategy, because that was my most valuable contribution to people. That's a real plus, I could just pivot like that and it was a decision that I made, I was responsible for it. The cons, I mean, there are many, many cons popping up in my mind, but the whole thing of making decisions alone, that is tough. Making decisions, sticking to it, not really having people keeping you accountable, so maybe you pivot and then pivot again, or rebrand, or rewrite and change things, or, "Oh, I'm actually changing all of my offers
now." There's nobody holding you to what you say, unless you have a coach or a mentor or a
mastermind. I think that is the key to working alone, it's being part of a community, not being afraid to ask for help, to have a coach and a mentor really kind of all the time. And of course, to work with a strategist like me.
Ron 11:28
That's so important. Chris and me, we both work with a executive coach, almost like a strategist, they help us with strategy and operations, and it has helped us tremendously. We've worked with other coaches too, from vocal to movement to yoga, and it's all connected and so important, but what it makes me think about is the future of work. We're approaching this disconnected, but connected world, where everything is decentralized in some way. It reminds me of a gig economy, where people can exchange goods, services, and help for others, without actually being a full-time employee. Through all of this greatness that has come into our world, I feel like there's one critical element that we miss a lot of times, and that's selling. How do you get to the point to where you can be the solopreneur, or work
with solopreneurs, help them with design and strategy, and also be a great salesperson?
Claire 12:29
Well, this is something that I think any creative service providers out there— I mean, I do work with quite a few designers as my clients, and photographers. I think creatives in general find it pretty hard to actually sell, whether it's because they love their work so much and they feel maybe guilty charging a lot of money for it, or just that their skill set is so focused on delivering the service that the whole marketing sales part feels inauthentic or it feels icky. It just doesn't feel like they're in their comfort zone there. So, in terms of getting clients, marketing yourself and actually getting that sale, it's work and you really have to do the work to get the work as a solopreneur. So, setting up marketing and sales systems and processes. I mean, how exciting is that? I'm talking about systems and processes already, but having a path for people to find out about you as a solopreneur, having consistent visibility, which kind
of speaks to the problem that you solve for people and speaks to it all the time, so that people get it and people know what you do. And then, finding a way to sell that aligns with your temperament. Now, I've done a lot of coaching on this, I've had a lot of sales coach already, and I've done too many books, I can't even start to name them, but sales strategy, it saved my business. Really knowing how to get people on calls is the first thing and then, on that call, allow your potential client the space to express their need, so that you know what you need to speak to. That was a key turning point for me, when I was learning about selling and learning about marketing, that it's absolutely not about me. People don't really care where I went to college, where I worked before, unless they know that I can be of service to them. So, people don't really care about me, until they know that I can help. That was a big mindset shift that all of my marketing and even on sales calls, it's an act of service, so that these people get to
solve that problem, because I know that I'm good at what I do. I know that I'm dedicated and honest, but they need to feel seen and heard in your marketing and in your sales calls, so that they're more likely to say, "Yes, please when can we start?"
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Chris 15:43
Absolutely, and I love that you mentioned Chris Doe, I'm a huge fan of his work. Definitely, from a business standpoint, I listen to all of his stuff and try to incorporate it in some way. You think about the folks in cybersecurity that are solopreneurs, or even on the small scale, folks like V-CISOs. These are virtual chief information security officers, where they come in and they help organizations with big strategy for cybersecurity, and there's a sliding scale, I'm sure, of how much people charge. Some people charge on a very high end, but people that aren't necessarily as confident in what they're producing might charge very, very little. What's interesting is that might even reflect in the way that they show up online, and so people are either trying to find their voice or they're trying to find their confidence. What have you found when it comes to looking at some of your clients and where they star and how they sound online to where they ultimately end up really showing their value?
Claire 16:40
Well, this is it. Again, for creatives, charging and pricing their work is really really difficult. I think women as well, we tend to undercut ourselves a little bit, just to maybe get the sale. We think that being cheaper might be the thing that gets the sale. So, with almost all of my strategy clients, we look at pricing, and we look at it, and this is something that Christo talks about a lot, it's value-based pricing. If their service is anywhere business related, we look at the monetary value of somebody investing in their service. We say, "Okay, well, if they're going to make $100,000, from the work that you do, your solution needs to cost about 10% of that." If your solution is maybe to help somebody with a more caring profession, like again, another coach or some kind of therapeutic or health service, that is an investment in health and well being. The cost of it needs to be reassuring to the person buying it that it's not just some cheap thing. There's a whole mentality in pricing there., and when you can charge premium, it validates the value of your service. If somebody's willing to pay X amount, which is your
perceived 10% of the value, this is getting really technical, sorry, you personally become more
confident because you know that people are willing to invest and they trust you with their time and their money to deliver on that service. So, I do talk about confidence quite a lot in the work that I do, because it's not just strategy and the mechanisms of showing up. It's also the mindset of showing up, and it's the mindset of making a claim that you are a valuable service and that people can actually get something from working with you. When I work with my strategy clients, we look at the positioning of their offer in the minds of their potential and ideal clients. We speak to that, and we speak to that value. It's amazing, by working on a content strategy, the confidence and their point of view comes through and they get to really reawaken the passion for why they started this thing in the first place. This can often happen by creating content, it has multiple benefits, because by creating content, you're really leaning
into your point of view and exploring it and going into niching and micro niching. And then, distributing that content means that it's going to help for your visibility, and creating content that is meaningful to your ideal clients, makes them feel seen and heard. That's really the key to any kind of marketing plan, or any kind of strategy to get clients online.
Ron 19:27
I love the fact that you were getting a little technical on us because all of this is really important. It almost takes me back to when Chris and I first got started with the podcast. We were really just wanting to create something fun, valuable for ourselves and also for others. Along the way, we found out that it wasn't just for us and the listener and the guest but it was also for our potential partners or sponsors, and we started to go down that route of making this into a business. It's turned out very successful. I'm very proud of the work that we've done, and I think a lot of our listeners, and people in cybersecurity and technology are on that same path, where they are doing something that is of value to them and others, and they could technically make money off of it. They would be very happy to do so, but it's almost a balancing act of when should you start? When do you typically work with clients, when it
comes to strategy and design? At what point do they reach out to you? At what point would you recommend a solopreneur, or content creator, to reach out to someone like you to get out of their own
way so they could shine in this digital world?
Claire 20:40
It's an interesting question, because strategy is essential at any stage, really, in your business. Starting out, I think people are reluctant. There's a lot of noise online, and there's a lot of people selling services and there's a lot of people who are very honest and dedicated and pure of heart, and they're going to get you to where you need to go, but I do think there are a lot of people out there who are just kind of regurgitating other people's content, and maybe a little bit of snake oil salesmanship going on there as well. I think a lot of people who are new in business, they might get sucked in to the loudest of those salespeople, and maybe have a bad experience. I've met a lot of people who've gotten burned by expensive coaching programs that went nowhere, or really expensive courses that had ultimately very little value to them. At the very, very early stages, I do recommend books, read and join groups, Slack groups and Facebook groups and be in communities, until such time that you have a little bit of money
coming in, or enough to hire a coach with whom you align. This could be in week one, year one, or in the first five minutes of your business, but doing it all alone is always a mistake. I think anybody who gets into business for themselves, or goes out on their own, they do have creative problem-solving brains and that means they think, "I can totally figure this out," especially in cybersecurity, those people are smart. They think, "I'm smart, I can figure this out." And yes, you can, but to go further faster, I think working with a mentor or a coach or strategist, one of the three or all of the three, you're always going to get further faster by finding somebody who vibes well with and understands what you're trying to achieve.
Chris 22:36
I bet you there's a lot of people listening right now like, "Oh, why am I listening to this" I'm not a solopreneur or entrepreneur," but I'd venture to guess that a lot of this applies to anyone trying to build their brand, because branding is really important in industry. It's really important in their community, because people tend to hire people that they know, they respect, and they've seen their work and the things that they care about. One of the things that I really struggled with, in the very beginning of creating content, is I didn't have my voice. I didn't know how to bring myself out in a way that would resonate with people, and so it was a lot of trial and error, but for the folks out there that want to really focus and make sure that they're coming as authentically as possible: What are some of the tenants
that you tend to teach people?
Claire 23:21
Don't be afraid to make mistakes, because it's by making mistakes that you learn. Reed Hoffman, I think his name is, the founder of LinkedIn, he says, if you're not embarrassed by your first launch, you waited too long, right? A red flag for me, in my own head and when I'm working with clients, is when I hear the phrase, "As soon as." As soon as I get my logo, I'll start a website. As soon as I get a website, I'll start doing social media. As soon as I have this, I'll start blogging. Many a business was built on a social media account. Many a business was built by starting out very, very simply and roughly. Starting before you feel ready, is really the only way that you can start because you can't know everything until you've tried some stuff. Showing up and making mistakes and maybe seeming a little bit foolish at the start, take it. That's what's gonna happen. Showing up imperfectly, people don't tend to care that much
if you are honestly trying to bring value. By understanding your ideal client, understanding the work that you're hoping to do with them, it really starts with understanding that and any kind of value you can bring to that conversation. It's good. You will look silly the first time.
Ron 24:46
That is so true, and that's also the devastating part, looking silly the first time or even the second time, it might not stop for quite a bit. We've been dropping a lot of names, a lot of books in this episode, I kind of wanted to continue down that path for a second at least, and ask you about letting go. I'm sure you have some great references for releasing that embarrassing feeling of showing off your first product or showing off your first LinkedIn post, even if that's the case? What is a reference that you always look back on, or book that you go back on, to remind yourself that it's alright to let go?
Claire 25:23
I mean, I'm sure you guys know of Ryan Holiday. Ego is the Enemy changed my life. Ego is the Enemy, it's one of these kinds of books that I think I've read it about five times now and then kind of dip into it from time to time again. Ego is the Enemy. In normal language, we think ego means somebody who's kind of maybe arrogant or full of themselves, but it's a psychological term for kind of that inner voice that wants to keep you safe. Ego is the Enemy was one of these kinds of turning point books for me. The lesson that I learned from that is that one of it's not about you, this whole thing needs to connect with everyone else. You've got to be of service. It's not that you don't matter, but there will be a voice in your head that says, "This is scary, this is dangerous," and that's there to protect you. It can protect you so much that you never advance on things, it can protect you so much that you kind of stay in the same place and stay small, stay quiet. There's another part of it, the flip side of it, is that when you're super confident, it really reminds you to connect with others. It's all about connecting with communities, having a good level of self awareness. So, Ego is the Enemy. It was just a massive influence on my life.
Chris 26:50
Ego is the Enemy, and it makes me think of another Ryan Holiday book. The Obstacle is the Way. I'm sure there's someone that's listening to this podcast right now, whether they're a V-CISO, or they're a consultant, or even just someone looking to build their own personal brand, and they're thinking, "This is great, I see this obstacle on the horizon, I'm going to attack it." What is the first two steps that you would convey to those listeners, as they embark on that journey?
Claire 27:19
On a journey to show up or to build a brand?
Chris 27:22
To build a brand and to basically show up as authentically themselves in marketing and their branding?
Claire 27:29
I do an exercise with my clients when we talk about the brand strategy piece of their general strategy. Who's going to benefit from this work? Why is that important to them? There's also another kind of zoom out that I do with people. Why are you doing this? You know, like the whole Simon Sinek thing, find your why, start with why. It's like, why are you doing this? Why did you start? Is that still why you keep going? Is this the change that you want to see in the world? Is it something that you want to do for yourself or help with others? So, another book reference there, but Simon Sinek Start with Why was a really interesting one for me, as well. Having a kind of emotional connection with the thing that you're doing is going to be what's going to keep you going on the dark days, or when you face some kind of failure, like your campaign didn't work or project fell through, or something just basically screwed up. The why is the thing that's going to keep you going. So, that's one of the foundational pieces that I do
with my clients is like, why? What's the point of all of this? Why are you doing this work and who should care about that? So, that would definitely, definitely be a first step. And then, just taking a first imperfect action, taking a first imperfect step towards what you'd like to achieve in your work and life.
Chris 28:57
I love that, take a first imperfect step. I've never heard it put that way, but I think that is very, very valuable for folks to hear. Thank you so much for taking the time out of your busy schedule to hop on the mics with us, Claire. If anyone out there wants to stay up to date with you and all the great things that you're doing, what are the best ways for people to do that?
Claire 29:15
Well, you can come over, come on over to I have a freebie, a digital strategy template, that's really useful to get clarity on what your first imperfect step might be. If you're on my mailing list, I send out a weekly newsletter with tips and observations and sometimes jokes, you know, that's how I roll. But come on over to and join the list, or I hang out and do silly things on Instagram, @ClaireCreative_Calm.
Ron 29:43
Love it, that was very inviting, so inviting that we've dropped it into the show notes. I would highly recommend everybody to stay up to date and check out Claire and her social media on Instagram. Claire, we wanted to say thank you again, really appreciate the great conversation. With that, we'll see everyone next time
Hacker Valley Studio 30:06
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