Season 4

|

Episode 3

How to build an independent design practice

Kevin Twohy

Founder @ Twohy Design Works

Jan 4, 2024

Jan 4, 2024

|

50 mins

50 mins

music by Dennis

About this Episode

This episode looks at Kevin Twohy’s 10+ year journey going from solo freelancer to independent design studio. We cover a LOT including:

  • Strategies for cold outreach and pricing

  • Tips for getting aligned quickly with clients

  • How Kevin gets plugged into a new team

  • Why Kevin has started positioning himself as a studio

  • A better way to take equity in client projects

  • Why you should be wary of starting a productized agency

  • + a lot more

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Insights + resources from top designers πŸ‘‡

Lauren LoPrete

Director of Design Systems @ Cash App

David Hoang

VP of Marketing and Design @ Replit

Adrien Griveau

Founding Designer @ Linear

James McDonald

Designer @ Clerk

Femke

Design Lead @ Gusto

Join 10K+ designers

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Deep Dives

Get our weekly breakdowns

Free lessons from πŸ‘‡

Lauren LoPrete

Lead designer @ Netflix

David Hoang

VP of Marketing and Design @ Replit

Adrien Griveau

Founding Designer @ Linear

Femke

Design Lead @ Gusto

Join 10K+ designers

HC

HC

HC

Deep Dives

Get our weekly breakdowns

Insights + resources from top designers πŸ‘‡

Lauren LoPrete

Director of Design Systems @ Cash App

David Hoang

VP of Marketing and Design @ Replit

Adrien Griveau

Founding Designer @ Linear

James McDonald

Designer @ Clerk

Femke

Design Lead @ Gusto

Join 10K+ designers

HC

HC

HC

HC

Transcript chapters

Getting into freelancing

Kevin: So, you know, the first half of my career has been in house at mostly at consumer facing early stage startups usually is the first designer joining early on before the product has a lot of like definition to it, figuring out what the product is and getting it out into market. And I did a few rounds of that at various companies it's always a gamble when you're joining, especially an early stage startup. I had a lot of great experiences. In this case, I had one, you know, not so great experience and I had sunk a couple years into that.

And so after I sort of felt, one, I needed a break, two, I was ready to sort of explore and actually the freelance, came into my life as I thought a tactic to sort of try before I buy. So I was oriented around finding a new company to join. And I felt like. Ah, if I had just worked with these people for a couple weeks, I think I would have had a really clear idea on where the mismatch was.

And it's nothing, you know, nothing wrong with them. They're, they're very lovely people. It's just we saw the world and the product differently and we had different working styles. So I could have figured that out so much more cheaply if I worked on a freelance project with them. So that was the motivation for starting my first set of, of freelance projects.

Getting into freelancing

Kevin: So, you know, the first half of my career has been in house at mostly at consumer facing early stage startups usually is the first designer joining early on before the product has a lot of like definition to it, figuring out what the product is and getting it out into market. And I did a few rounds of that at various companies it's always a gamble when you're joining, especially an early stage startup. I had a lot of great experiences. In this case, I had one, you know, not so great experience and I had sunk a couple years into that.

And so after I sort of felt, one, I needed a break, two, I was ready to sort of explore and actually the freelance, came into my life as I thought a tactic to sort of try before I buy. So I was oriented around finding a new company to join. And I felt like. Ah, if I had just worked with these people for a couple weeks, I think I would have had a really clear idea on where the mismatch was.

And it's nothing, you know, nothing wrong with them. They're, they're very lovely people. It's just we saw the world and the product differently and we had different working styles. So I could have figured that out so much more cheaply if I worked on a freelance project with them. So that was the motivation for starting my first set of, of freelance projects.

How Kevin landed his first few clients

Ridd: So then can you talk a little bit about how you landed those first clients? Were you totally viewing them through the lens of like, would I want to work here full time or like, how did those opportunities present themselves?

Kevin: Yeah, I was looking for companies like the types of companies I would want to work for, you know, and work with. And so, you know, I'm looking for people sometimes that are hiring for a full time design lead or a full time founding designer. In the early stage, you don't have any other clients, you don't have any other referrals to bank on. So the two places that mine came from were just my network. So they're referrals, but not in the traditional sense. It's just emailing people who you know, who trust you.

And they may be from your, uh, not past freelance clients, but just from your career. Like you had a prior job and you email your boss from the prior job and say, This is what I'm doing now. Here's how I want to be described. Here's what you should keep an ear out for. And you do that a lot. And you need to have a lot of people out there sort of listening for you so that luck can strike.

And then the other is basically cold outreach. Not in a spammy way, but, you know, looking around and finding the people who , either are the people you want to work for or very adjacent to them, and just reaching out, and that can be on Twitter, via email, and this is something that I did a lot in the early stage, and to be honest, I was a little embarrassed about it, to begin with, and now I'm, like, very proud of it, and I do it to this day.

I sent a cold email literally yesterday. and got a response, just someone who I thought, I really would love to connect with this person. Not for a project right now, but just down the road. Maybe it'll be five years later., you may get a reply to 20 percent of them, and you may get a conversation from 10 percent of them, maybe you end up getting a gig from 5 percent of those, 1 in 20, and that's great.

That's all you need to get going and, , the success rate of that does not need to be very high for it to still be a good tactic because it's not what you're going to be doing forever. You're just trying to get the flywheel going, essentially.

Ridd: I think an interesting way to think about this conversation is going to be to zoom into an element of the freelancing process and then kind of talk about how it has evolved for you as you've moved from exploring freelancing to realizing you really like it to now kind of, you know, having a lot of success repositioning yourself and deciding that you kind of want to do this forever.

How Kevin landed his first few clients

Ridd: So then can you talk a little bit about how you landed those first clients? Were you totally viewing them through the lens of like, would I want to work here full time or like, how did those opportunities present themselves?

Kevin: Yeah, I was looking for companies like the types of companies I would want to work for, you know, and work with. And so, you know, I'm looking for people sometimes that are hiring for a full time design lead or a full time founding designer. In the early stage, you don't have any other clients, you don't have any other referrals to bank on. So the two places that mine came from were just my network. So they're referrals, but not in the traditional sense. It's just emailing people who you know, who trust you.

And they may be from your, uh, not past freelance clients, but just from your career. Like you had a prior job and you email your boss from the prior job and say, This is what I'm doing now. Here's how I want to be described. Here's what you should keep an ear out for. And you do that a lot. And you need to have a lot of people out there sort of listening for you so that luck can strike.

And then the other is basically cold outreach. Not in a spammy way, but, you know, looking around and finding the people who , either are the people you want to work for or very adjacent to them, and just reaching out, and that can be on Twitter, via email, and this is something that I did a lot in the early stage, and to be honest, I was a little embarrassed about it, to begin with, and now I'm, like, very proud of it, and I do it to this day.

I sent a cold email literally yesterday. and got a response, just someone who I thought, I really would love to connect with this person. Not for a project right now, but just down the road. Maybe it'll be five years later., you may get a reply to 20 percent of them, and you may get a conversation from 10 percent of them, maybe you end up getting a gig from 5 percent of those, 1 in 20, and that's great.

That's all you need to get going and, , the success rate of that does not need to be very high for it to still be a good tactic because it's not what you're going to be doing forever. You're just trying to get the flywheel going, essentially.

Ridd: I think an interesting way to think about this conversation is going to be to zoom into an element of the freelancing process and then kind of talk about how it has evolved for you as you've moved from exploring freelancing to realizing you really like it to now kind of, you know, having a lot of success repositioning yourself and deciding that you kind of want to do this forever.

Strategies for cold outreach

Ridd: So maybe the first one that we can zoom into is this. Cold outreach, how often are you doing that? But even more interestingly, I'd love to hear how that process has evolved over those phases. Like, are there things you've learned about how you pitch yourself to companies in a cold setting or ways that you've improved that part of your practice,

Kevin: Yeah, definitely. And I do think that is sort of a common theme of all, All freelance questions have sort of this arc of in the beginning and in the middle and then later and cold outreach falls into the category of how do I get clients? That's probably the number one question that I get from aspiring freelance folks.

And so within that cold outreach You know in the beginning, I think it was very tactical and mapped to a service, right? I can do digital product design for you on an hourly rate. And here's the company and maybe I have an idea of what type of design or what projects they might need and suggesting, hey, do you need this type of help now or in the next few months?

Let's have a conversation and here are my rates. And so that's like very transactional and very practical and you're just hoping that they might have that need now or soon. And I think that's also in the early , stage, you're not really, , trading necessarily on your reputation because you might not have one or your public persona because you might not have one.

Really it's relying like very heavily on the portfolio, right? That someone's going to click through and see what is this person about? What are they capable of? Is it a fit for what I'm looking for? So very kind of transactional portfolio driven. Maybe you're emailing a lot more people because you're not actually sure yet.

That's another angle to this is, you know, I think. Early on in a freelance journey, I think it makes sense to be oriented towards exploration and figuring out, you may not know exactly the right way that you want to work. You may not know the exact right client for you, and it may not be obvious. So, it's good to cast a wide net in that stage.

In kind of the middle tier of my career, the frequency decreased and the format changed a little bit, but also started serving a bit of a different function, which was sort of there's this like feast or famine cycle of freelancing.

You have a bunch of business at one point and then six months later you have nothing and that's a common thing that I hear. So how do you modulate that and make sure you have what you. need or want, when you need or want it. So you rely on inbounds to the degree that you can, but you don't control how many you're getting and when.

cold outreach though you do control. So that, in kind of the middle part of my career, kind of served a different function of like modulating supply and demand. Where I would look, let's say towards the end, let's say it's summer, towards the end of the year, it's looking like I might need to roll off of some projects onto new clients.

And I don't really want to be at the mercy of what's in my inbox at that time. So why don't I send some, outreach or get in touch with some folks now, a few months in advance. So that I know basically what I'm trying to tee up is some set of leads that I'm interested in for about three months from now.

So that's kind of in the middle stage. And I would say, Fast forward to today. I'm usually doing this just to be in touch with interesting people that I want to connect with that maybe I like respect what they're doing or their point of view on the world or maybe they're in a completely different industry.

Like this cold email I sent yesterday, I have zero expectation that this is going to be a client for me in the next couple of years. It's just someone that I think will be good for myself and my business to be in touch with and I might learn something from them, might learn something about a new industry. It speaks to the importance of investing in your reputation and having a good reputation because most of the people you're cold emailing, they're going to find someone who knows you on Twitter or LinkedIn. it really, really pays to have high confidence that in 99 percent of cases, they're going to get a really good positive answer from that reference check.

Ridd: you mentioned in the early days, kind of being exploratory and not even really being sure about how you want to work and what you want this to look like. So. What were some of the things in those first few months or maybe even the first year that you were learning about yourself that shaped the way that you even approached your work as a freelancer?

Strategies for cold outreach

Ridd: So maybe the first one that we can zoom into is this. Cold outreach, how often are you doing that? But even more interestingly, I'd love to hear how that process has evolved over those phases. Like, are there things you've learned about how you pitch yourself to companies in a cold setting or ways that you've improved that part of your practice,

Kevin: Yeah, definitely. And I do think that is sort of a common theme of all, All freelance questions have sort of this arc of in the beginning and in the middle and then later and cold outreach falls into the category of how do I get clients? That's probably the number one question that I get from aspiring freelance folks.

And so within that cold outreach You know in the beginning, I think it was very tactical and mapped to a service, right? I can do digital product design for you on an hourly rate. And here's the company and maybe I have an idea of what type of design or what projects they might need and suggesting, hey, do you need this type of help now or in the next few months?

Let's have a conversation and here are my rates. And so that's like very transactional and very practical and you're just hoping that they might have that need now or soon. And I think that's also in the early , stage, you're not really, , trading necessarily on your reputation because you might not have one or your public persona because you might not have one.

Really it's relying like very heavily on the portfolio, right? That someone's going to click through and see what is this person about? What are they capable of? Is it a fit for what I'm looking for? So very kind of transactional portfolio driven. Maybe you're emailing a lot more people because you're not actually sure yet.

That's another angle to this is, you know, I think. Early on in a freelance journey, I think it makes sense to be oriented towards exploration and figuring out, you may not know exactly the right way that you want to work. You may not know the exact right client for you, and it may not be obvious. So, it's good to cast a wide net in that stage.

In kind of the middle tier of my career, the frequency decreased and the format changed a little bit, but also started serving a bit of a different function, which was sort of there's this like feast or famine cycle of freelancing.

You have a bunch of business at one point and then six months later you have nothing and that's a common thing that I hear. So how do you modulate that and make sure you have what you. need or want, when you need or want it. So you rely on inbounds to the degree that you can, but you don't control how many you're getting and when.

cold outreach though you do control. So that, in kind of the middle part of my career, kind of served a different function of like modulating supply and demand. Where I would look, let's say towards the end, let's say it's summer, towards the end of the year, it's looking like I might need to roll off of some projects onto new clients.

And I don't really want to be at the mercy of what's in my inbox at that time. So why don't I send some, outreach or get in touch with some folks now, a few months in advance. So that I know basically what I'm trying to tee up is some set of leads that I'm interested in for about three months from now.

So that's kind of in the middle stage. And I would say, Fast forward to today. I'm usually doing this just to be in touch with interesting people that I want to connect with that maybe I like respect what they're doing or their point of view on the world or maybe they're in a completely different industry.

Like this cold email I sent yesterday, I have zero expectation that this is going to be a client for me in the next couple of years. It's just someone that I think will be good for myself and my business to be in touch with and I might learn something from them, might learn something about a new industry. It speaks to the importance of investing in your reputation and having a good reputation because most of the people you're cold emailing, they're going to find someone who knows you on Twitter or LinkedIn. it really, really pays to have high confidence that in 99 percent of cases, they're going to get a really good positive answer from that reference check.

Ridd: you mentioned in the early days, kind of being exploratory and not even really being sure about how you want to work and what you want this to look like. So. What were some of the things in those first few months or maybe even the first year that you were learning about yourself that shaped the way that you even approached your work as a freelancer?

Key takeaways from year 1

Kevin: I Guess the theme of the early first stage of freelancing for me was just figuring out how to do it and feeling very awkward at it. Every aspect of it, you know, there's the work itself, but then there's meeting the client, there's pitching, there's negotiation, there's billing, invoicing, and every single aspect of that, you kind of feel like you're doing wrong.

And there's not a lot of confidence built up in it yet, so that, I would characterize that as just sort of uncertainty and trying to figure out how to do it, or if I'm even going to be any good at it. I think I had a high degree of competence in the core work product, but there's so much more, especially when you're working one on one with clients, you don't have an agency in between, so you're not just like producing the work, you're actually running the client engagement yourself.

So, that was just very exploratory. You learn by doing. And , you sort of learn as you go. And I think the biggest thing from that, there's the practical learnings.

You may learn an industry or a tactic or a way to run meetings. Or a way to showcase work or negotiate that works for you. But the biggest thing I think that comes out of that, at least for me, is just a, a core confidence that, , Okay, I'm actually pretty decent at this. I know how to do it. I've learned a few things.

And that confidence that you bring to early negotiations and meetings with clients, they can really sense it from the very beginning. And it's not a confidence born of ego, like I have all the answers. It's just , I'm not nervous about this. You can trust me. We'll figure it out together and I'll have your back.

And a lot of times when clients are asking, it feels like they're putting you through the ringer, asking a lot of questions. Really, in a lot of cases, what they're looking for is that sense, and you can give that through answers, but a lot of it is just an intangible sense of, I've done this a lot, and I've figured a lot of things out.

Key takeaways from year 1

Kevin: I Guess the theme of the early first stage of freelancing for me was just figuring out how to do it and feeling very awkward at it. Every aspect of it, you know, there's the work itself, but then there's meeting the client, there's pitching, there's negotiation, there's billing, invoicing, and every single aspect of that, you kind of feel like you're doing wrong.

And there's not a lot of confidence built up in it yet, so that, I would characterize that as just sort of uncertainty and trying to figure out how to do it, or if I'm even going to be any good at it. I think I had a high degree of competence in the core work product, but there's so much more, especially when you're working one on one with clients, you don't have an agency in between, so you're not just like producing the work, you're actually running the client engagement yourself.

So, that was just very exploratory. You learn by doing. And , you sort of learn as you go. And I think the biggest thing from that, there's the practical learnings.

You may learn an industry or a tactic or a way to run meetings. Or a way to showcase work or negotiate that works for you. But the biggest thing I think that comes out of that, at least for me, is just a, a core confidence that, , Okay, I'm actually pretty decent at this. I know how to do it. I've learned a few things.

And that confidence that you bring to early negotiations and meetings with clients, they can really sense it from the very beginning. And it's not a confidence born of ego, like I have all the answers. It's just , I'm not nervous about this. You can trust me. We'll figure it out together and I'll have your back.

And a lot of times when clients are asking, it feels like they're putting you through the ringer, asking a lot of questions. Really, in a lot of cases, what they're looking for is that sense, and you can give that through answers, but a lot of it is just an intangible sense of, I've done this a lot, and I've figured a lot of things out.

Handling the early stages of a client engagement

Ridd: Can we talk a little bit about like the very beginning part of a client engagement where you're actually having some kind of a negotiation or a back and forth or some questions happening, because I've done this a few times and I've always felt like it was very sloppy and elongated, but I'm not even really sure like what I'm doing wrong.

And so maybe you could even talk about what that was like for you in the early stages. And what were some of the things that you identified where you could kind of button up that process a little bit or present yourself more effectively?

Kevin: Like you in my early stages of freelancing, I didn't know what to ask. I didn't know the right questions. I was definitely looking for the client to basically tell me exactly what to do. And I do think that's a common , trajectory of sort of like, you tell me what to do, then let's figure it out together, and then I'm not going to tell the client what to do, but you know, in many cases for an experienced freelancer, they're coming to you for expertise, not just in how to do the design, but is this even the right project?

Can you tell us what you've seen from other projects like this that you've run? Am I asking for the right thing? So in the beginning, yeah, not really sure what questions to ask. Also, you don't know any of the ways things can go wrong that you might want to hunt out beforehand. So that just comes from experience.

Ridd: Can you talk a little bit about like, what are the ways that things can go wrong? Like, what are the pitfalls that you're actively trying to avoid?

Kevin: One of the biggest things is just a lack of alignment, a misalignment. You think you're on the same page about some detail, and you're not. I'll give you an example. So, and, and I'll segue into kind of like the middle phase of how I tried to solve this that I think was the wrong way, but I ended up developing this little intake survey that I asked clients to do.

I thought, okay, well, I have all these questions that are really important. I really want the answer to them. So I'll put them in this intake survey and ask the client to fill it out before an engagement. That turned out, in my opinion, to be a horrible idea, but, and I'll tell you why. But one of the questions I put in there was basically, , who's responsible for the ultimate success of this project? Is it me, Kevin, is it you, the client, or is it us together? Most people tend to say it's us together, but the answer to that question being misaligned is very telling, right? And if the client says, hey, it's you, what they're saying is, I'm counting on you to get the whole thing right. So if something seems off. They're asking for you to correct it. Whereas if they say, it's me, the client, they're kind of communicating, I, rightly or wrongly, I want to run the show and I want you to essentially do what, what I'm telling you to do.

So having a misalignment on those types of topics is at the root of a lot of things going wrong. But another thing that I would ask up front is just very explicitly, if this project, what does it look like if it's successful? But if this project goes wrong, if it goes off the rails and it's a failure, why do you think that might have happened?

And the answers to that are very, very telling. It might surface things that you weren't even thinking about. Not even concerned about. And you learn that's the client's number one fear. And a lot of times it's something that, Oh, that's not an issue at all. And as I take this project on, I'm always going to have that at the back of my mind.

Client X is really worried about this failure mode. Like it may be that they're worried that as an external vendor, you won't be integrated enough with their team. So I'm going to make sure to be talking to their team all the time. , so yeah, But I'll speak about the, , the survey. So I thought that was a really clever way to do it.

And I think I also was looking around a lot of people automating systems and making things hyper efficient and putting that in a survey, , and skipping the conversation misses out on one of the best opportunities to. run the process, this process that you're talking about, which might be called sort of like alignment or discovery or scoping.

Because usually the answer that they can give either in a survey or the very first answer that the client gives to a question like that is missing a lot of context, a lot of business context, emotional context. And really I think a lot of what I'm working with and going on in the The course of an engagement comes out of those early conversations and digging three or four or five levels deeper So the why are we doing this?

Oh, we have this business need and just showing a curiosity Well, can you tell me about that? Tell me tell me about it from the beginning How did we get into this situation or if there's a concern? Well, what's really behind that concern? Can you tell me about it? I find that when the client senses that that's what's going on, oftentimes maybe 30 minutes in that conversation, there's this very perceptible shift. And , they kind of go like, you know, Kevin, and they take a deep breath and they say, let me tell you really what's going on.

And that's where you learn everything. I guess themes there are take the time to show. A true and genuine curiosity about what is going on in the moment that you meet that client, both the person and the business. And, yeah, just listen very, very carefully to what's being said and what's not being said, because a lot of that, it'll never show up when they email you saying I need some design done, and it'll never show up in a survey.

You have to find that stuff.

Handling the early stages of a client engagement

Ridd: Can we talk a little bit about like the very beginning part of a client engagement where you're actually having some kind of a negotiation or a back and forth or some questions happening, because I've done this a few times and I've always felt like it was very sloppy and elongated, but I'm not even really sure like what I'm doing wrong.

And so maybe you could even talk about what that was like for you in the early stages. And what were some of the things that you identified where you could kind of button up that process a little bit or present yourself more effectively?

Kevin: Like you in my early stages of freelancing, I didn't know what to ask. I didn't know the right questions. I was definitely looking for the client to basically tell me exactly what to do. And I do think that's a common , trajectory of sort of like, you tell me what to do, then let's figure it out together, and then I'm not going to tell the client what to do, but you know, in many cases for an experienced freelancer, they're coming to you for expertise, not just in how to do the design, but is this even the right project?

Can you tell us what you've seen from other projects like this that you've run? Am I asking for the right thing? So in the beginning, yeah, not really sure what questions to ask. Also, you don't know any of the ways things can go wrong that you might want to hunt out beforehand. So that just comes from experience.

Ridd: Can you talk a little bit about like, what are the ways that things can go wrong? Like, what are the pitfalls that you're actively trying to avoid?

Kevin: One of the biggest things is just a lack of alignment, a misalignment. You think you're on the same page about some detail, and you're not. I'll give you an example. So, and, and I'll segue into kind of like the middle phase of how I tried to solve this that I think was the wrong way, but I ended up developing this little intake survey that I asked clients to do.

I thought, okay, well, I have all these questions that are really important. I really want the answer to them. So I'll put them in this intake survey and ask the client to fill it out before an engagement. That turned out, in my opinion, to be a horrible idea, but, and I'll tell you why. But one of the questions I put in there was basically, , who's responsible for the ultimate success of this project? Is it me, Kevin, is it you, the client, or is it us together? Most people tend to say it's us together, but the answer to that question being misaligned is very telling, right? And if the client says, hey, it's you, what they're saying is, I'm counting on you to get the whole thing right. So if something seems off. They're asking for you to correct it. Whereas if they say, it's me, the client, they're kind of communicating, I, rightly or wrongly, I want to run the show and I want you to essentially do what, what I'm telling you to do.

So having a misalignment on those types of topics is at the root of a lot of things going wrong. But another thing that I would ask up front is just very explicitly, if this project, what does it look like if it's successful? But if this project goes wrong, if it goes off the rails and it's a failure, why do you think that might have happened?

And the answers to that are very, very telling. It might surface things that you weren't even thinking about. Not even concerned about. And you learn that's the client's number one fear. And a lot of times it's something that, Oh, that's not an issue at all. And as I take this project on, I'm always going to have that at the back of my mind.

Client X is really worried about this failure mode. Like it may be that they're worried that as an external vendor, you won't be integrated enough with their team. So I'm going to make sure to be talking to their team all the time. , so yeah, But I'll speak about the, , the survey. So I thought that was a really clever way to do it.

And I think I also was looking around a lot of people automating systems and making things hyper efficient and putting that in a survey, , and skipping the conversation misses out on one of the best opportunities to. run the process, this process that you're talking about, which might be called sort of like alignment or discovery or scoping.

Because usually the answer that they can give either in a survey or the very first answer that the client gives to a question like that is missing a lot of context, a lot of business context, emotional context. And really I think a lot of what I'm working with and going on in the The course of an engagement comes out of those early conversations and digging three or four or five levels deeper So the why are we doing this?

Oh, we have this business need and just showing a curiosity Well, can you tell me about that? Tell me tell me about it from the beginning How did we get into this situation or if there's a concern? Well, what's really behind that concern? Can you tell me about it? I find that when the client senses that that's what's going on, oftentimes maybe 30 minutes in that conversation, there's this very perceptible shift. And , they kind of go like, you know, Kevin, and they take a deep breath and they say, let me tell you really what's going on.

And that's where you learn everything. I guess themes there are take the time to show. A true and genuine curiosity about what is going on in the moment that you meet that client, both the person and the business. And, yeah, just listen very, very carefully to what's being said and what's not being said, because a lot of that, it'll never show up when they email you saying I need some design done, and it'll never show up in a survey.

You have to find that stuff.

Other elements of Kevin's process

Ridd: So you mentioned scrapping the survey and, you know, you're kind of talking about like this discovery call. And I think there's like really interesting questions in there. Can we zoom out just like a little bit to like, what other parts do you just have included as like the standard process for how you work?

Like once a contract is signed, are there other systems or things that you find yourself doing or boxes that you're checking pretty much every time?

Kevin: Yeah, so I'll talk about kind of like before contract or before engagement and then after. in both of those, I'm pretty process light. I am very organized and very like meticulous in my work, but I don't try to do that through a bunch of sort of like templates and decks and things like that

I try to just take on that responsibility in that way of working. As an individual, and so before signing a contract these days, and you know, I should say as context, I work on long term retainer based projects. They can range from, you know, a year to, in one case, , one of my longer projects was four years long.

I would say the median is about 18 months to get a project from the very, very early stage to something that's working in the market. suffice it to say, they're big long term projects and I want to make sure that it's a really, really good fit from the beginning. So that kind of like courtship period tends to be pretty long.

I might talk to a potential client six, seven, eight times before you kick off an engagement and it's months, months in advance usually. So a lot of times. I'm the, the framing for those conversations is, Hey, you know, we think we would like to work together. We're going to, you know, sign a contract eventually, but let's just get into it now.

Let's not wait to sign a contract. I'm not going to actually start hardcore design work, but I want to really dig into not the abstract, but the details of what we're going to be working on and what the challenge is. So those can be sort of working sessions or more like a consultative, more like an interview back and forth.

But basically just talking to the client naturally and showing, again, that, , genuine curiosity in their work and their business. And that also just brings out a lot of the personality. You get to know each other more as a human. So that process might take place over a couple months, getting to know each other.

And at the end of that, I think you have a really good idea of whether it's going to be a fit or not. If I have any uncertainty at the end of that process, it usually means it's not a good fit. And again, that's pretty unique to these long, deep engagements. The process obviously would be different if you're, you know, if you're an illustrator or if, you know, you're building a website over six weeks or something like that.

But that's, that's sort of how I run them.

Other elements of Kevin's process

Ridd: So you mentioned scrapping the survey and, you know, you're kind of talking about like this discovery call. And I think there's like really interesting questions in there. Can we zoom out just like a little bit to like, what other parts do you just have included as like the standard process for how you work?

Like once a contract is signed, are there other systems or things that you find yourself doing or boxes that you're checking pretty much every time?

Kevin: Yeah, so I'll talk about kind of like before contract or before engagement and then after. in both of those, I'm pretty process light. I am very organized and very like meticulous in my work, but I don't try to do that through a bunch of sort of like templates and decks and things like that

I try to just take on that responsibility in that way of working. As an individual, and so before signing a contract these days, and you know, I should say as context, I work on long term retainer based projects. They can range from, you know, a year to, in one case, , one of my longer projects was four years long.

I would say the median is about 18 months to get a project from the very, very early stage to something that's working in the market. suffice it to say, they're big long term projects and I want to make sure that it's a really, really good fit from the beginning. So that kind of like courtship period tends to be pretty long.

I might talk to a potential client six, seven, eight times before you kick off an engagement and it's months, months in advance usually. So a lot of times. I'm the, the framing for those conversations is, Hey, you know, we think we would like to work together. We're going to, you know, sign a contract eventually, but let's just get into it now.

Let's not wait to sign a contract. I'm not going to actually start hardcore design work, but I want to really dig into not the abstract, but the details of what we're going to be working on and what the challenge is. So those can be sort of working sessions or more like a consultative, more like an interview back and forth.

But basically just talking to the client naturally and showing, again, that, , genuine curiosity in their work and their business. And that also just brings out a lot of the personality. You get to know each other more as a human. So that process might take place over a couple months, getting to know each other.

And at the end of that, I think you have a really good idea of whether it's going to be a fit or not. If I have any uncertainty at the end of that process, it usually means it's not a good fit. And again, that's pretty unique to these long, deep engagements. The process obviously would be different if you're, you know, if you're an illustrator or if, you know, you're building a website over six weeks or something like that.

But that's, that's sort of how I run them.

How Kevin gets plugged into the team

Ridd: because you're working on these super long engagements, I'm curious to learn more about how you assimilate into the team. Something even as simple as like how you share your work and source feedback. Like, do you have your process that you bring with you? Or do you kind of work backwards from the way that the team is already working?

Can you just shed a little bit of light on how you plug into a team and what your schedule ultimately looks like?

Kevin: In terms of vendors for design and engineering, et cetera, you've kind of got So you've got agency, big agency on one end, you've got, , wild west solo freelancer on the other end. And then there's this thing like a design practice or an individual studio of ones.

We can talk about that later, on that range there, the tactics and the way that those companies work with clients and vendors are totally different. And one of the things that I have been trying to do with my business over the past few years is, you know, sometimes you might see in marketing copy for.

Designers like all the benefits of an agency without the overhead. You see that all the time I Started to think and I understand why but I started to think really deeply about really digging into that and thinking about what are the Benefits like why are these clients? What are they looking for when they hire these big expensive agencies?

And what are they actually getting? It's one thing to say Oh agencies are all bloated, but they're hiring them for a reason a good reason why are they hiring freelancers and what are they looking for in that? And why is it the case that most of the people that do the work for them are employees?

They would hire an employee in many cases if they could, but they can't, so they're talking to you. really thinking about how can I actually, not just say it, but bring to the table the benefits of what these companies are going to the biggest and best agencies for in the form factor that usually they really want, which is an employee.

And they want you to feel as much as possible like an employee in terms of how you interact with their culture, how you interact with their other employees, how they don't want another system to deal with you. So that means, , for better or worse being in Slack often. So I, to get back to your question, I really try to, meet the company and the client where they're at and , deliver work in a way that an employee probably couldn't, but do it in the form factor of basically pretending I'm their best super employee.

How Kevin gets plugged into the team

Ridd: because you're working on these super long engagements, I'm curious to learn more about how you assimilate into the team. Something even as simple as like how you share your work and source feedback. Like, do you have your process that you bring with you? Or do you kind of work backwards from the way that the team is already working?

Can you just shed a little bit of light on how you plug into a team and what your schedule ultimately looks like?

Kevin: In terms of vendors for design and engineering, et cetera, you've kind of got So you've got agency, big agency on one end, you've got, , wild west solo freelancer on the other end. And then there's this thing like a design practice or an individual studio of ones.

We can talk about that later, on that range there, the tactics and the way that those companies work with clients and vendors are totally different. And one of the things that I have been trying to do with my business over the past few years is, you know, sometimes you might see in marketing copy for.

Designers like all the benefits of an agency without the overhead. You see that all the time I Started to think and I understand why but I started to think really deeply about really digging into that and thinking about what are the Benefits like why are these clients? What are they looking for when they hire these big expensive agencies?

And what are they actually getting? It's one thing to say Oh agencies are all bloated, but they're hiring them for a reason a good reason why are they hiring freelancers and what are they looking for in that? And why is it the case that most of the people that do the work for them are employees?

They would hire an employee in many cases if they could, but they can't, so they're talking to you. really thinking about how can I actually, not just say it, but bring to the table the benefits of what these companies are going to the biggest and best agencies for in the form factor that usually they really want, which is an employee.

And they want you to feel as much as possible like an employee in terms of how you interact with their culture, how you interact with their other employees, how they don't want another system to deal with you. So that means, , for better or worse being in Slack often. So I, to get back to your question, I really try to, meet the company and the client where they're at and , deliver work in a way that an employee probably couldn't, but do it in the form factor of basically pretending I'm their best super employee.

Going from freelancer to individual studio

Ridd: Something that I've noticed recently is you've made this shift from positioning yourself more as like a, an individual studio with two design works rather than this, freelancing model.

Can you talk a little bit more about what went into that decision

Kevin: I've been freelancing for about ten years, and for that entire ten years, essentially, I was just working under my own name, and part of the reason for that is that I've just always really believed in the power and the benefit of what the individual relationship can do and what it can produce between a client and a vendor and the challenges that come. with working with a team. I've just always enjoyed and believed in the power of that personal approach and relationship. And I never made any attempt during those ten years to sort of like, Puff myself up and call it Acme studios when it was really just me I I felt very strongly that that was sort of like giving away the best thing I have going which is these people They want to work with with an individual.

That's why they're talking to me in the first place They could have hired an agency by now. And in terms of making this shift there's a few main reasons. One is that well, I was on paternity leave because I, I had our son about two years ago and I had realized that I think I'm probably never going back to a full time job. And I think if I can, I want to do this for the rest of my career that being the case.

I need to create or I want to create a framework that will kind of support that longevity. And there's a few key things that are different about, you know, how I'm operating the business now than when I started out as a freelancer. One of them is, it is not just me. I have, , at least one or two associate designers part time, usually floating around,

and, I have other folks that are helping out sort of around the margins that are not part of my organization, but are other, other freelancers. So there is a capability of taking on scope that is far beyond what an individual freelancer typically could do. the other piece of it is, sitting back and reflecting, oh, I might be doing this for 30 more years.

Everyone needs to think about the trajectory of their career and sort of always be learning and inventing themselves and having new challenges to face. And when you run your own business, you need to do that for yourself. for me, a big part of that is, I think my core competency is always going to be around, you know, product design, software, and, you know, some hardware product design.

But, I, over 30 years, I'm going to be wanting, to do more than that. Which means. Maybe branding, maybe industrial design, and expanding the scope of what I'm working on for clients. And that's a little bit hard to do under an individual identity because I think folks have a mental model of kind of like a single discipline.

A product designer, a software engineer, so expanding into more of a studio model, I shouldn't even say a studio model, just a studio framing allows me a container that can hold a lot of that broader set of disciplines and broader ways of working than just the way that a single freelancer does.

And the last thing I'll say on that, since I, , was so kind of like on my own and ruminating in this process, I was really, really worried about losing the framing of the individual in that process and being legible as an agency. So that's why if you go to the TUI DesignWorks website, , it's a little bit deranged and it's just a long, unhinged essay.

And the reason for that is I was just trying to think about what is, the most individual way that I could convey my personality and approach that could only be done by one person. And so that's kind of part of the thinking behind it.

Ridd: I love the intentionality of that because it did stand out to me and it's kind of cool to even think about the underlying reason for why you design the site that way.

Going from freelancer to individual studio

Ridd: Something that I've noticed recently is you've made this shift from positioning yourself more as like a, an individual studio with two design works rather than this, freelancing model.

Can you talk a little bit more about what went into that decision

Kevin: I've been freelancing for about ten years, and for that entire ten years, essentially, I was just working under my own name, and part of the reason for that is that I've just always really believed in the power and the benefit of what the individual relationship can do and what it can produce between a client and a vendor and the challenges that come. with working with a team. I've just always enjoyed and believed in the power of that personal approach and relationship. And I never made any attempt during those ten years to sort of like, Puff myself up and call it Acme studios when it was really just me I I felt very strongly that that was sort of like giving away the best thing I have going which is these people They want to work with with an individual.

That's why they're talking to me in the first place They could have hired an agency by now. And in terms of making this shift there's a few main reasons. One is that well, I was on paternity leave because I, I had our son about two years ago and I had realized that I think I'm probably never going back to a full time job. And I think if I can, I want to do this for the rest of my career that being the case.

I need to create or I want to create a framework that will kind of support that longevity. And there's a few key things that are different about, you know, how I'm operating the business now than when I started out as a freelancer. One of them is, it is not just me. I have, , at least one or two associate designers part time, usually floating around,

and, I have other folks that are helping out sort of around the margins that are not part of my organization, but are other, other freelancers. So there is a capability of taking on scope that is far beyond what an individual freelancer typically could do. the other piece of it is, sitting back and reflecting, oh, I might be doing this for 30 more years.

Everyone needs to think about the trajectory of their career and sort of always be learning and inventing themselves and having new challenges to face. And when you run your own business, you need to do that for yourself. for me, a big part of that is, I think my core competency is always going to be around, you know, product design, software, and, you know, some hardware product design.

But, I, over 30 years, I'm going to be wanting, to do more than that. Which means. Maybe branding, maybe industrial design, and expanding the scope of what I'm working on for clients. And that's a little bit hard to do under an individual identity because I think folks have a mental model of kind of like a single discipline.

A product designer, a software engineer, so expanding into more of a studio model, I shouldn't even say a studio model, just a studio framing allows me a container that can hold a lot of that broader set of disciplines and broader ways of working than just the way that a single freelancer does.

And the last thing I'll say on that, since I, , was so kind of like on my own and ruminating in this process, I was really, really worried about losing the framing of the individual in that process and being legible as an agency. So that's why if you go to the TUI DesignWorks website, , it's a little bit deranged and it's just a long, unhinged essay.

And the reason for that is I was just trying to think about what is, the most individual way that I could convey my personality and approach that could only be done by one person. And so that's kind of part of the thinking behind it.

Ridd: I love the intentionality of that because it did stand out to me and it's kind of cool to even think about the underlying reason for why you design the site that way.

How Kevin works with associate designers

Ridd: Can you talk a little bit more about how you are working with other people and when you loop in and associate and how you even structure that working relationship?

Kevin: , the way that I work, you know, like I said, I typically have one or two associate designers that are part time.

Some of them sort of like float in and out. I use those resources to, for a few things. One is to enable me to move much faster. And sometimes I say to my clients, you know, 80 percent done, 80 percent to go. Meaning we've basically figured this thing out, but there might be 20 hours of work left. And I don't want to tell them, hey, I'll see you in 20 hours.

I want to tell them what's next. And so, having designers that I work with that can help extend that work and extend the bandwidth, it also helps modulate a little bit, like I was saying, they're just, you know, working with multiple clients at a time. There are just weeks where everything hits, it's incredibly busy, and so I need a safety net to help even those out, but the, the specific thing to say about the associate designers, and I will say in case he listens to this, the one designer that I'm working with now, I've worked with on and off for five years and he's actually quite senior.

So I wouldn't, I don't want him to think I'm calling him a junior designer, but, , it really is more of an apprentice and an assistant type of model. And you see this in other industries. So like my wife, , is a stylist, for example, she worked with photographers. You see this with architects, they run a singular creative vision, but they need help to do their job at the highest level.

So they have people on their team that are working as an extra set of hands, and they may be very creatively capable on their own, but the in order for it to run efficiently and at a high level, there is one person in charge. And for me, it's a little difficult to talk about because it's hard to talk about without sounding Egotistical, honestly.

Like, I don't care about being at the center because I think I'm the best. I just know that you can achieve incredible things with one person driving the creative vision and other people helping.

How Kevin works with associate designers

Ridd: Can you talk a little bit more about how you are working with other people and when you loop in and associate and how you even structure that working relationship?

Kevin: , the way that I work, you know, like I said, I typically have one or two associate designers that are part time.

Some of them sort of like float in and out. I use those resources to, for a few things. One is to enable me to move much faster. And sometimes I say to my clients, you know, 80 percent done, 80 percent to go. Meaning we've basically figured this thing out, but there might be 20 hours of work left. And I don't want to tell them, hey, I'll see you in 20 hours.

I want to tell them what's next. And so, having designers that I work with that can help extend that work and extend the bandwidth, it also helps modulate a little bit, like I was saying, they're just, you know, working with multiple clients at a time. There are just weeks where everything hits, it's incredibly busy, and so I need a safety net to help even those out, but the, the specific thing to say about the associate designers, and I will say in case he listens to this, the one designer that I'm working with now, I've worked with on and off for five years and he's actually quite senior.

So I wouldn't, I don't want him to think I'm calling him a junior designer, but, , it really is more of an apprentice and an assistant type of model. And you see this in other industries. So like my wife, , is a stylist, for example, she worked with photographers. You see this with architects, they run a singular creative vision, but they need help to do their job at the highest level.

So they have people on their team that are working as an extra set of hands, and they may be very creatively capable on their own, but the in order for it to run efficiently and at a high level, there is one person in charge. And for me, it's a little difficult to talk about because it's hard to talk about without sounding Egotistical, honestly.

Like, I don't care about being at the center because I think I'm the best. I just know that you can achieve incredible things with one person driving the creative vision and other people helping.

What it means to run a "design practice"

Ridd: so you mentioned this point where you realized that you wanted to, and also probably thought you were able to kind of do this freelancing thing forever. So. So at that point, and now with, you know, two design works, are there other ways that your practice has evolved that we're not talking about, or even just ways that how you view your life and work as a freelancer has changed over the years?

Kevin: we're gonna have to talk about the phrase independent studio practice of. And a lot of it revolves around that, which, , you know, when I would see that over the years, you know, it's one person, like the independent studio practice of John Doe or Jane Doe.

And I have to admit, I kind of rolled my eyes, like, what is this all about? This person seems full of themselves. And of course, you know, that's on my website now, too. And I think over the years, I developed a realization of what that's about, or what it's really about to me. And to me, it really wraps around that inflection point of realizing, oh, I'm going to be doing this for a really long time.

And with that in mind, I think you don't want to run a career oriented just around the whims of your clients, , you know, changing every six months. I think ideally, You want to have a sense of who you are and what you're doing and where you're going. And the clients can, can sort of meet you halfway and work with you if that, if that works for them.

So I think the shift from, when you're a freelancer, especially starting out, if you think about it like a, like a space system or a planetary system, you're orbiting around the center of gravity of the client for everything, in terms of how you work, what you're doing, , even your visual language, all of that.

Maybe as you're developing in your freelance career, like your mass is increasing a little bit, you have a little bit more of your own center of gravity. And for me, realizing I'm going to be doing this, you know, for maybe 30 more years and developing sort of a brand and a framework around myself was really about, I think, recognizing that I am going to start to develop my own sense of gravity around what I'm doing, how I work, how I think about design, where I want to be headed in terms of my personal development and self development, and just have that sense of self orientation.

And it doesn't mean that when you meet with clients you say, this is my way, take it or leave it. It's not about that at all. In fact, sort of the opposite. But it's almost like, you know, you're not going to work with the same client for your whole career. So you have to have some sense of continuity.

Around where you're heading and who you are and to me that's what that word practice Really means it's not just a fancy freelancer. On the flip side, like I've found, I think clients really respond very well to that.

And that comes from, you know, it goes back to that theme of confidence, but, , you do want to be flexible and you do want to be able to change your mind, but I think they really want to hear that you have a point of view and a way of working and something to offer and bring to the table. That has been a big shift in how I've thought about my work and my practice from kind of like freelancer to running, you know, my design practice now.

What it means to run a "design practice"

Ridd: so you mentioned this point where you realized that you wanted to, and also probably thought you were able to kind of do this freelancing thing forever. So. So at that point, and now with, you know, two design works, are there other ways that your practice has evolved that we're not talking about, or even just ways that how you view your life and work as a freelancer has changed over the years?

Kevin: we're gonna have to talk about the phrase independent studio practice of. And a lot of it revolves around that, which, , you know, when I would see that over the years, you know, it's one person, like the independent studio practice of John Doe or Jane Doe.

And I have to admit, I kind of rolled my eyes, like, what is this all about? This person seems full of themselves. And of course, you know, that's on my website now, too. And I think over the years, I developed a realization of what that's about, or what it's really about to me. And to me, it really wraps around that inflection point of realizing, oh, I'm going to be doing this for a really long time.

And with that in mind, I think you don't want to run a career oriented just around the whims of your clients, , you know, changing every six months. I think ideally, You want to have a sense of who you are and what you're doing and where you're going. And the clients can, can sort of meet you halfway and work with you if that, if that works for them.

So I think the shift from, when you're a freelancer, especially starting out, if you think about it like a, like a space system or a planetary system, you're orbiting around the center of gravity of the client for everything, in terms of how you work, what you're doing, , even your visual language, all of that.

Maybe as you're developing in your freelance career, like your mass is increasing a little bit, you have a little bit more of your own center of gravity. And for me, realizing I'm going to be doing this, you know, for maybe 30 more years and developing sort of a brand and a framework around myself was really about, I think, recognizing that I am going to start to develop my own sense of gravity around what I'm doing, how I work, how I think about design, where I want to be headed in terms of my personal development and self development, and just have that sense of self orientation.

And it doesn't mean that when you meet with clients you say, this is my way, take it or leave it. It's not about that at all. In fact, sort of the opposite. But it's almost like, you know, you're not going to work with the same client for your whole career. So you have to have some sense of continuity.

Around where you're heading and who you are and to me that's what that word practice Really means it's not just a fancy freelancer. On the flip side, like I've found, I think clients really respond very well to that.

And that comes from, you know, it goes back to that theme of confidence, but, , you do want to be flexible and you do want to be able to change your mind, but I think they really want to hear that you have a point of view and a way of working and something to offer and bring to the table. That has been a big shift in how I've thought about my work and my practice from kind of like freelancer to running, you know, my design practice now.

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