Spring forward: creative strategies to help freelancers blossom

Interview

November 15, 2025

Spring forward: creative strategies to help freelancers blossom

Interview

November 15, 2025

Spring forward: creative strategies to help freelancers blossom

Interview

November 15, 2025

In our series of interviews, we explore the demanding realm of independent work, touching on the ups, downs, and everyday necessities of freelance work within various design studios and brands for a career path. We had a conversation with Lee Chao. She generously shared insights into her journey to freelance work including the experiences that have significantly moulded her viewpoint and methodology until now.

The Independent Professionals: Lee Chao articulates the triggers and understandings indebted to her imaginative process. At the point of writing, she was collaborating with Penta, a designer based in New York.

Where the most time is spent

MF Greetings Lee! Is everything well?

LC Hello! I'm delighted to take part in this sequence. I have been somewhat swamped recently, but I'm gradually adjusting to a better rhythm in my professional commitments. It's beyond my wildest dreams to be able to maintain independent work, but I find myself so grateful for the opportunity.

MF Who are you presently undertaking freelance work with?

LC At the moment, I am freelancing with Natasha Jen at Pentagram, though my journey here has been quite intriguing. I initially joined Pentagram last year to work alongside Emily Oberman, but recently made a switch to contribute to a different project. Any freelancer can attest that flexibility is part and parcel of the game, and I'm thrilled to navigate this transition whilst remaining in surroundings that have become so endearing to me.

MF Could you describe your usual day?

LC My schedule tends to be quite flexible because it often depends on the people I'm collaborating with. As a contract worker at Pentagram, I usually keep standard office hours, effectively operating as a full-time employee. When I'm not at Pentagram, I juggle various other projects, which means no two days look the same. Meeting schedules can also fluctuate based on time zones and project deadlines.

In my leisure time, I enjoy activities that don't involve staring at a screen, such as cooking, exercising, or even refurbishing items I've found on Craigslist, reading for my book club, or watching films.

MF What initiated your freelancing career?

LC It wasn't necessarily planned this way (a little pun there), but I believe things panned out the way they were supposed to. The pressure to secure a full-time position after graduating was immense. Being accepted into the World’s Greatest Internship marked a significant pivot in my life - I quit my existing job, packed my belongings and used the ensuing six months to recalibrate my ambitions and objectives. I was exposed to a wide variety of professionals doing interesting work, which sparked a desire for more such experiences.

I returned to New York and began working as a freelancer at MoMA. Until then, I hadn't considered working for an institution, but I found the experience truly enlightening. Although I subsequently collaborated with different studios of varying sizes, I always recall that initial experience. It's key for me to work with people who are generous, who genuinely want the best for those they work with, and who enrich others with their knowledge.

MF Could you reflect on your time with the World's Greatest Internship? How would you describe the whole journey?

LC To be honest, when I realized I was chosen, it was quite shocking. I had no idea what lay ahead, but I attempted to use each phase as a stepping stone for learning. Each city brought a fresh vibe that influenced the atmosphere within each studio. I started to be more observant of my environment, noticing how a location can affect individuals, their perspective on life and, ultimately, how they tackle design. I'm deeply grateful to everyone who embraced us and allowed us to engage in their workflow. This exposure proves to be truly priceless.

MF What tips would you offer to design graduates who might struggle to afford travel for professional exposure?

LC During the World's Greatest Internship, I didn't incur any costs for travelling or accommodation, nor would I have been able to. Those were handled in large part by sponsors and partners. Travel isn't a requirement to gain experience! The pandemic, if anything, should have instilled that lesson. In my opinion, it's feasible to establish a design community right where you are. Look for mentors, ask them for guidance, exchange ideas and resources. Most people are genuinely willing to share their expertise if you are genuine and eager in your approach.

MF Can you describe your work environment?

LC I've turned an additional room in my Brooklyn apartment into an office setup. It's always been a dream of mine to have a large workspace, thus I purchased a butcher block counter and customized it with legs. Having various books and reference materials at disposal for when I require scanning is something I enjoy. Additionally, I maintain a cabinet teeming with art crafting supplies and paper specimens for trying out different ideas.

MF Why did you choose New York for your practice?

LC I shifted from a quaint liberal arts college in Michigan to conclude a degree in Communication Design at Parsons here, and have been here since then. I have weighed up other cities previously, but New York seems to be fitting for me currently. My circle is here, and there’s an essence in turning a location into a home.

Freelancing has bestowed upon me two gifts: Autonomy and assurance

MF What makes freelancing suitable for your work approach?

LC It significantly depends on your employer and their requirements, and self-employment provides more control over both aspects. Collaborating with people thrills me, but having the convenience to operate remotely when necessary is crucial to me. As for the design method, it varies from one studio to another. Working on your own lets you decide your style of work and client interaction. Some studios fervently encourage designers to take the initiative. Some are just looking for labor. Both approaches have their merits and drawbacks. You simply have to choose the arrangement that fits you best and pursue opportunities accordingly.

MF What aspects of being a freelancer do you find most satisfying and why?

LC Freelancing has granted me two essential things: self-reliance and self-assurance. I can function remotely as and when needed, and fight for my interests to deliver the finest work possible. As a freelancer, you become your own executor, supervisor, and time manager. I relish this responsibility as it lets me be in charge of my work.

In my leisure, I enjoy tackling tasks that don’t demand a computer

MF Is there a person or thing you draw creatively from more than others?

LC Items that have been discarded and cinema deeply inspire me! I get a thrill out of digging around the web for unusual books and artifacts to employ in my studies. My movie viewing frequency is probably the highest it's ever been. Important for me are elements such as shape, color, and arrangement in various films, not simply for their aesthetic appeal but also for their emotional resonance. Seconds, a recent film I saw, was profoundly impactful. The credit sequence, designed by the unparalleled Saul Bass, showed the protagonist's face seemingly through water droplets.

MF Which aspects of design captivate you the most?

LC I’m particularly captivated by elements related to culture and amusements. I’m driven when the work feels immediate. I adore projects that feel like a dialog, participatory, and that reflect something larger than themselves. That could very likely be shown through a brand's persona, or perhaps via a series of posters for a building symposium, title slides for a brief movie, a pop-up event in town, or a museum display.

MF Are you considering a steady position in the future?

LC Absolutely! The dilemma of being a contract freelancer is the sensation of being a full-time staff member without the perks. At the end of the day, there's no significant distinction because although full-time positions offer a sense of security, freelancing has shown to be surprisingly reliable. It ultimately depends on how you want to allocate your time and how you want others to invest in you. I value the guidance a mentor provides, leading me to believe that a full-time role may aid in achieving that.

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In our series of interviews, we explore the demanding realm of independent work, touching on the ups, downs, and everyday necessities of freelance work within various design studios and brands for a career path. We had a conversation with Lee Chao. She generously shared insights into her journey to freelance work including the experiences that have significantly moulded her viewpoint and methodology until now.

The Independent Professionals: Lee Chao articulates the triggers and understandings indebted to her imaginative process. At the point of writing, she was collaborating with Penta, a designer based in New York.

Where the most time is spent

MF Greetings Lee! Is everything well?

LC Hello! I'm delighted to take part in this sequence. I have been somewhat swamped recently, but I'm gradually adjusting to a better rhythm in my professional commitments. It's beyond my wildest dreams to be able to maintain independent work, but I find myself so grateful for the opportunity.

MF Who are you presently undertaking freelance work with?

LC At the moment, I am freelancing with Natasha Jen at Pentagram, though my journey here has been quite intriguing. I initially joined Pentagram last year to work alongside Emily Oberman, but recently made a switch to contribute to a different project. Any freelancer can attest that flexibility is part and parcel of the game, and I'm thrilled to navigate this transition whilst remaining in surroundings that have become so endearing to me.

MF Could you describe your usual day?

LC My schedule tends to be quite flexible because it often depends on the people I'm collaborating with. As a contract worker at Pentagram, I usually keep standard office hours, effectively operating as a full-time employee. When I'm not at Pentagram, I juggle various other projects, which means no two days look the same. Meeting schedules can also fluctuate based on time zones and project deadlines.

In my leisure time, I enjoy activities that don't involve staring at a screen, such as cooking, exercising, or even refurbishing items I've found on Craigslist, reading for my book club, or watching films.

MF What initiated your freelancing career?

LC It wasn't necessarily planned this way (a little pun there), but I believe things panned out the way they were supposed to. The pressure to secure a full-time position after graduating was immense. Being accepted into the World’s Greatest Internship marked a significant pivot in my life - I quit my existing job, packed my belongings and used the ensuing six months to recalibrate my ambitions and objectives. I was exposed to a wide variety of professionals doing interesting work, which sparked a desire for more such experiences.

I returned to New York and began working as a freelancer at MoMA. Until then, I hadn't considered working for an institution, but I found the experience truly enlightening. Although I subsequently collaborated with different studios of varying sizes, I always recall that initial experience. It's key for me to work with people who are generous, who genuinely want the best for those they work with, and who enrich others with their knowledge.

MF Could you reflect on your time with the World's Greatest Internship? How would you describe the whole journey?

LC To be honest, when I realized I was chosen, it was quite shocking. I had no idea what lay ahead, but I attempted to use each phase as a stepping stone for learning. Each city brought a fresh vibe that influenced the atmosphere within each studio. I started to be more observant of my environment, noticing how a location can affect individuals, their perspective on life and, ultimately, how they tackle design. I'm deeply grateful to everyone who embraced us and allowed us to engage in their workflow. This exposure proves to be truly priceless.

MF What tips would you offer to design graduates who might struggle to afford travel for professional exposure?

LC During the World's Greatest Internship, I didn't incur any costs for travelling or accommodation, nor would I have been able to. Those were handled in large part by sponsors and partners. Travel isn't a requirement to gain experience! The pandemic, if anything, should have instilled that lesson. In my opinion, it's feasible to establish a design community right where you are. Look for mentors, ask them for guidance, exchange ideas and resources. Most people are genuinely willing to share their expertise if you are genuine and eager in your approach.

MF Can you describe your work environment?

LC I've turned an additional room in my Brooklyn apartment into an office setup. It's always been a dream of mine to have a large workspace, thus I purchased a butcher block counter and customized it with legs. Having various books and reference materials at disposal for when I require scanning is something I enjoy. Additionally, I maintain a cabinet teeming with art crafting supplies and paper specimens for trying out different ideas.

MF Why did you choose New York for your practice?

LC I shifted from a quaint liberal arts college in Michigan to conclude a degree in Communication Design at Parsons here, and have been here since then. I have weighed up other cities previously, but New York seems to be fitting for me currently. My circle is here, and there’s an essence in turning a location into a home.

Freelancing has bestowed upon me two gifts: Autonomy and assurance

MF What makes freelancing suitable for your work approach?

LC It significantly depends on your employer and their requirements, and self-employment provides more control over both aspects. Collaborating with people thrills me, but having the convenience to operate remotely when necessary is crucial to me. As for the design method, it varies from one studio to another. Working on your own lets you decide your style of work and client interaction. Some studios fervently encourage designers to take the initiative. Some are just looking for labor. Both approaches have their merits and drawbacks. You simply have to choose the arrangement that fits you best and pursue opportunities accordingly.

MF What aspects of being a freelancer do you find most satisfying and why?

LC Freelancing has granted me two essential things: self-reliance and self-assurance. I can function remotely as and when needed, and fight for my interests to deliver the finest work possible. As a freelancer, you become your own executor, supervisor, and time manager. I relish this responsibility as it lets me be in charge of my work.

In my leisure, I enjoy tackling tasks that don’t demand a computer

MF Is there a person or thing you draw creatively from more than others?

LC Items that have been discarded and cinema deeply inspire me! I get a thrill out of digging around the web for unusual books and artifacts to employ in my studies. My movie viewing frequency is probably the highest it's ever been. Important for me are elements such as shape, color, and arrangement in various films, not simply for their aesthetic appeal but also for their emotional resonance. Seconds, a recent film I saw, was profoundly impactful. The credit sequence, designed by the unparalleled Saul Bass, showed the protagonist's face seemingly through water droplets.

MF Which aspects of design captivate you the most?

LC I’m particularly captivated by elements related to culture and amusements. I’m driven when the work feels immediate. I adore projects that feel like a dialog, participatory, and that reflect something larger than themselves. That could very likely be shown through a brand's persona, or perhaps via a series of posters for a building symposium, title slides for a brief movie, a pop-up event in town, or a museum display.

MF Are you considering a steady position in the future?

LC Absolutely! The dilemma of being a contract freelancer is the sensation of being a full-time staff member without the perks. At the end of the day, there's no significant distinction because although full-time positions offer a sense of security, freelancing has shown to be surprisingly reliable. It ultimately depends on how you want to allocate your time and how you want others to invest in you. I value the guidance a mentor provides, leading me to believe that a full-time role may aid in achieving that.

Share

Twitter

Facebook

Copy link

In our series of interviews, we explore the demanding realm of independent work, touching on the ups, downs, and everyday necessities of freelance work within various design studios and brands for a career path. We had a conversation with Lee Chao. She generously shared insights into her journey to freelance work including the experiences that have significantly moulded her viewpoint and methodology until now.

The Independent Professionals: Lee Chao articulates the triggers and understandings indebted to her imaginative process. At the point of writing, she was collaborating with Penta, a designer based in New York.

Where the most time is spent

MF Greetings Lee! Is everything well?

LC Hello! I'm delighted to take part in this sequence. I have been somewhat swamped recently, but I'm gradually adjusting to a better rhythm in my professional commitments. It's beyond my wildest dreams to be able to maintain independent work, but I find myself so grateful for the opportunity.

MF Who are you presently undertaking freelance work with?

LC At the moment, I am freelancing with Natasha Jen at Pentagram, though my journey here has been quite intriguing. I initially joined Pentagram last year to work alongside Emily Oberman, but recently made a switch to contribute to a different project. Any freelancer can attest that flexibility is part and parcel of the game, and I'm thrilled to navigate this transition whilst remaining in surroundings that have become so endearing to me.

MF Could you describe your usual day?

LC My schedule tends to be quite flexible because it often depends on the people I'm collaborating with. As a contract worker at Pentagram, I usually keep standard office hours, effectively operating as a full-time employee. When I'm not at Pentagram, I juggle various other projects, which means no two days look the same. Meeting schedules can also fluctuate based on time zones and project deadlines.

In my leisure time, I enjoy activities that don't involve staring at a screen, such as cooking, exercising, or even refurbishing items I've found on Craigslist, reading for my book club, or watching films.

MF What initiated your freelancing career?

LC It wasn't necessarily planned this way (a little pun there), but I believe things panned out the way they were supposed to. The pressure to secure a full-time position after graduating was immense. Being accepted into the World’s Greatest Internship marked a significant pivot in my life - I quit my existing job, packed my belongings and used the ensuing six months to recalibrate my ambitions and objectives. I was exposed to a wide variety of professionals doing interesting work, which sparked a desire for more such experiences.

I returned to New York and began working as a freelancer at MoMA. Until then, I hadn't considered working for an institution, but I found the experience truly enlightening. Although I subsequently collaborated with different studios of varying sizes, I always recall that initial experience. It's key for me to work with people who are generous, who genuinely want the best for those they work with, and who enrich others with their knowledge.

MF Could you reflect on your time with the World's Greatest Internship? How would you describe the whole journey?

LC To be honest, when I realized I was chosen, it was quite shocking. I had no idea what lay ahead, but I attempted to use each phase as a stepping stone for learning. Each city brought a fresh vibe that influenced the atmosphere within each studio. I started to be more observant of my environment, noticing how a location can affect individuals, their perspective on life and, ultimately, how they tackle design. I'm deeply grateful to everyone who embraced us and allowed us to engage in their workflow. This exposure proves to be truly priceless.

MF What tips would you offer to design graduates who might struggle to afford travel for professional exposure?

LC During the World's Greatest Internship, I didn't incur any costs for travelling or accommodation, nor would I have been able to. Those were handled in large part by sponsors and partners. Travel isn't a requirement to gain experience! The pandemic, if anything, should have instilled that lesson. In my opinion, it's feasible to establish a design community right where you are. Look for mentors, ask them for guidance, exchange ideas and resources. Most people are genuinely willing to share their expertise if you are genuine and eager in your approach.

MF Can you describe your work environment?

LC I've turned an additional room in my Brooklyn apartment into an office setup. It's always been a dream of mine to have a large workspace, thus I purchased a butcher block counter and customized it with legs. Having various books and reference materials at disposal for when I require scanning is something I enjoy. Additionally, I maintain a cabinet teeming with art crafting supplies and paper specimens for trying out different ideas.

MF Why did you choose New York for your practice?

LC I shifted from a quaint liberal arts college in Michigan to conclude a degree in Communication Design at Parsons here, and have been here since then. I have weighed up other cities previously, but New York seems to be fitting for me currently. My circle is here, and there’s an essence in turning a location into a home.

Freelancing has bestowed upon me two gifts: Autonomy and assurance

MF What makes freelancing suitable for your work approach?

LC It significantly depends on your employer and their requirements, and self-employment provides more control over both aspects. Collaborating with people thrills me, but having the convenience to operate remotely when necessary is crucial to me. As for the design method, it varies from one studio to another. Working on your own lets you decide your style of work and client interaction. Some studios fervently encourage designers to take the initiative. Some are just looking for labor. Both approaches have their merits and drawbacks. You simply have to choose the arrangement that fits you best and pursue opportunities accordingly.

MF What aspects of being a freelancer do you find most satisfying and why?

LC Freelancing has granted me two essential things: self-reliance and self-assurance. I can function remotely as and when needed, and fight for my interests to deliver the finest work possible. As a freelancer, you become your own executor, supervisor, and time manager. I relish this responsibility as it lets me be in charge of my work.

In my leisure, I enjoy tackling tasks that don’t demand a computer

MF Is there a person or thing you draw creatively from more than others?

LC Items that have been discarded and cinema deeply inspire me! I get a thrill out of digging around the web for unusual books and artifacts to employ in my studies. My movie viewing frequency is probably the highest it's ever been. Important for me are elements such as shape, color, and arrangement in various films, not simply for their aesthetic appeal but also for their emotional resonance. Seconds, a recent film I saw, was profoundly impactful. The credit sequence, designed by the unparalleled Saul Bass, showed the protagonist's face seemingly through water droplets.

MF Which aspects of design captivate you the most?

LC I’m particularly captivated by elements related to culture and amusements. I’m driven when the work feels immediate. I adore projects that feel like a dialog, participatory, and that reflect something larger than themselves. That could very likely be shown through a brand's persona, or perhaps via a series of posters for a building symposium, title slides for a brief movie, a pop-up event in town, or a museum display.

MF Are you considering a steady position in the future?

LC Absolutely! The dilemma of being a contract freelancer is the sensation of being a full-time staff member without the perks. At the end of the day, there's no significant distinction because although full-time positions offer a sense of security, freelancing has shown to be surprisingly reliable. It ultimately depends on how you want to allocate your time and how you want others to invest in you. I value the guidance a mentor provides, leading me to believe that a full-time role may aid in achieving that.

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