Kelsey Cronkhite

Kelsey Cronkhite is the Creative Director of Pinegate Road, a design firm that she established in 2011 to build brand foundations for creative businesses. At Pinegate Road, Kelsey works with clients to find their core values and turn them into inspired designs and lettering. When Kelsey is not designing and managing her team you can find her on The Pinegate Road podcast chatting about the creative journey. And as luck would have it, just last week she interviewed Jess Levitz, Freelance Wisdom's founder!

Thank you Kelsey, for sharing your insight, positive vibes, and valuable resources with us today!

Kelsey Cronkhite | Freelance Wisdom

Tell me about your path to becoming a freelance designer.

I became an accidental freelance designer in grad school at SCAD in Savannah, GA. I was thrown into this world of design theory, and wasn’t doing much actual design practice. While I was spending most of my time reading and writing, as a designer, I was missing that tangible creative work. Because of this, I started my now business, Pinegate Road. It started as a personal blog where everything was a huge mess. It was just my fun place for creativity and exploration. This was back in 2011 where blogs were just becoming a bigger part of design culture, and there wasn’t much pressure to create wonderful content. Having a post with a picture of a fun dress and saying “I like this dress” was really enough to get by as good content back then. Hah! Anyways, as I started this blog, I was putting myself and my name out there more and more. Eventually, I got a few inquiries about blog design. I started doing blog design for other bloggers for about $300 a site. These were my first clients, and while I was drastically undercharging, I had so much fun building out blogs that matched these client’s personalities. Over the next two years, I honed in on my offerings, raised my prices, and by the time I graduated in 2013, I essentially had a full-blown design studio that I was running in my spare time. After graduating, I took a job in Cleveland, OH at American Greetings where I worked as a stationery designer for three years. It was an amazing job, and one that I didn’t think I would leave for quite a while. All along, I was running Pinegate Road, and I had a steady flow of clients coming in. Sometimes I would tell myself that it was too much, and that I needed to give up something, but then another fun client would come in and I would keep on going! It was pretty much insanity, but an insanity I am so thankful I kept up with. This past year, I was diagnosed with endometriosis. When this happened, it put me into a pretty devastating place, and I knew that my body couldn’t keep up with the pace I was working at. I decided to leave my job, and focus on Pinegate Road full-time. Because I had been saving and making money on the side all-along, I knew I would be OK taking the leap. It was coming face-to-face with this disease that forced me to take the step back and make the choice for my future health and the life I wanted to live. If you’re struggling with health issues, or wanting to know step by step how I made this decision, I go over this in-depth in the third episode of my podcast, The Pinegate Road Podcast.
Kelsey Cronkhite | Freelance Wisdom

In the beginning, how did you attract your first good clients?

Not having my freelance business be my sole financial backbone certainly made this easier! Freelance money was my side money, so I was able to only take on clients that I felt aligned with my values. While not everyone was the most perfect fit, I think this is really something that you figure out the more you try. Now, I’m thankful to have built my portfolio with clients that were dream clients while working on the side. This is helping me continue to get those dreamy clients while Pinegate Road is my sole income. I also think that going to conferences and collaborating with people in your industry (or slightly outside your industry) is key! When you meet people in person, they are much more likely to want to connect with and hire you before they go to someone they don’t know. While I’ve always genuinely gone to conferences to learn and meet new people and to be inspired, this weird side thing happens where you get to know people who have all these amazing skills. It’s only natural to collaborate and hire from these new found friends. I’ve been both on the receiving end of being hired from people I’ve met at live events, and also have hired people I’ve met. You get to that next level of trust when you can talk and meet someone in real life. Can you tell I’m a huge proponent of going to conferences? :)

 "Going to conferences and collaborating with people in your industry (or slightly outside your industry) is key! When you meet people in person, they are much more likely to want to connect with and hire you before they go to someone they don’t know."


Kelsey Cronkhite | Freelance Wisdom

Do you have any tips for being your most productive?

At first, when you’re working all alone and trying to make this big dreamy business come to life, your schedule is going to be your best friend. Here is the crazy schedule that I put myself through for a couple of years while I was running Pinegate Road and working full-time. I think finding the time that you do have in your schedule to be productive and work on your business, and really getting to work when you have that time, was key when I was trying to build my business. Now, one of my favorite productivity hacks is working in pomodoros. I’m still in the early stages of working for myself (three months in), so I’m in that stage where working from my couch in my pajamas is my everyday reality. Some days it makes me feel super productive, and other days I feel the laziest. As long as I’m not getting behind on deadlines, and I’m keeping my future goals rolling, I don’t feel bad about not being the most productive every day at this point. I’m giving myself some grace as I transition. I know that I have the tendency to over-work, and that only leads to burnout. I don’t want to go through that or deal with the kind of health issues I experienced before.

What has been your greatest struggle as a freelancer so far?

Getting dressed. Hah! But seriously. That’s been a hard one for me ;) Guys, I’m honestly still in the honeymoon stage with this all. Every day I’m grateful that I am able to make my own schedule, and that I am able to live life on my own terms for the first time. It’s seriously incredible. I have a feeling that I will eventually have struggles with budgeting, and if everything goes as planned in my personal life, juggling a kiddo in the next year or so. Oh, and I hate forms and technical things. That is probably terrible to say as a person making their living on the internet, but it’s the truth. Thank goodness for amazing team members who help me out!
Kelsey Cronkhite | Freelance Wisdom
Kelsey Cronkhite | Freelance Wisdom

Pinegate Road is a team and you are the Creative Director, can you tell us about your decision to bring on employees/collaborators?

YES! At first I started bringing on contract designers while I was working my full-time job. I wasn’t able to keep up with the demand of work that Pinegate Road had, and I wasn’t wanting to turn work down. I knew the only way to keep growing while running my business was to hire out the design work, and act as the creative director for projects. This was so hard, but a huge leap for my business. I was able to contract out work to two designers, and they helped with projects throughout the last couple years. At the same time, I started changing directions from pure logo design to more holistic branding solutions — going into the brand strategy, business planning, identity design, and web design for creative businesses ready to take that next big leap in their businesses. With this, I was now bringing in experts in web development, copywriting, and photography to make sure that Pinegate Road clients were getting the best experience and brands built for them. Since my leap to full-time freelance, I have been handling all the design work for the past couple months, and I have hired a virtual assistant who now runs my podcast. We started off with 20 hours per month, and are now expanding to 50 hours per month with new duties. She’s amazing! I’m launching a new site for Pinegate, as well as a new business plan and strategy that she is helping me implement. There are a lot of changes happening now that I’m able to devote myself to my business 100%, and having her has been helping me not get so stuck in the details and the busy work. She also has amazing insights into growing a business, and knows more technical aspects than I do. She helps me through so much, and is a huge asset to our team. Hi Sarah!! :)

Do you have any advice for handling communication as a Creative Director?

If you have a regular assistant like I do, scheduling a weekly meeting to go over all tasks is very helpful. We meet every Thursday morning via skype, and go over all of our to-do’s for the week and brainstorm new ways to better our systems. If you’re working with contractors like I do often for other projects, making sure that you have a clear procedure set up before you start is key. Having this is essential to know what each of you should expect from the other. I also use asana to keep all tasks for both my VA and my contractors up to date with deadlines, expectations, files, and general conversation. I work a little differently with each of my contractors. Some I’m on texting relationships with, and that works best, and others email back and forth. I’m sure as things grow further, these communication efforts will need to be systematized, but for now it’s working a little differently for each person. Google drive is great for documents and folders of any work that needs to be transferred from person to person. We can even link those folders up in asana, which keeps everything in one place for people to access as needed.
Kelsey Cronkhite | Freelance Wisdom

What is your favorite thing about working as a team?

I love being able to have a second opinion, and to know that someone has my back if I’m doing something crazy. Especially with my VA, and the next new steps for Pinegate, we’ve been brainstorming different ways to make certain things happen. She’ll often have great ideas that I would never have thought of on how to go about a certain process, or knows a cool way to make something look even better or work better than I could ever dream up. Knowing that you don’t have to do it all yourself is a huge relief. I also love hiring contractors that have exceptional skills — they bring the best to the table, and I love that they can focus on their expertise without having to deal with the project management side of things. I secretly love being a little bossy too, so when I work as a project manager, I feel like I’m working in my element as well ;) I’ll always be doing some design, because that’s my true passion, but knowing that my business can keep growing and moving along even when I’m sick or want to take a vacation is priceless.

How do you continue to attract your ideal clients?

I think this goes back to making connections with people you LOVE being around. This means going to conferences, sharing your passions, sharing your voice, so people can hear you and say ‘ME TOO’ to what you’re putting out there. I’ve met future clients on Instagram, through Pinterest, in person, and through referrals. It’s all about consistently putting your best work out there, and giving more than you’re taking. I’ve always been a cheerleader of people following their passions, and now I get to do that through my business. The more I cheer, help, and empower, the more clients I seem to get that are aligned with that vision as well. I get so awkwardly attached to my clients and their vision. I think putting that heart and soul into the work and process shows, and that propels more of the same to keep coming at you.
Kelsey Cronkhite | Freelance Wisdom

"The more I cheer, help, and empower, the more clients I seem to get that are aligned with that vision as well."


Do you have any tips for dealing with the nitty-gritty business details? 

Freshbooks! That seriously changed my money game! I send that to my accountant each year, and they are able to do my taxes from that. Also, seeing my money come and go, and being able to invoice so easily keeps me on track. At first, I was hand-designing all my invoices (I know guys!!!). That was frustrating, took way too much time, and I probably forgot to invoice half of my clients because I wasn’t keeping track of all that was going on. Freshbooks made it 100% easier to keep on top of everything, and it makes you look really professional as a business owner. I also have hired an accountant for the past couple years. I don’t get taxes and all things that have to do with forms (gah, I’m the worst!). So giving this all to someone who knows what they are doing saves me so much head space come March and April. As for contracts, I’m still doing these all by hand in illustrator. I love making them look pretty, and due to the custom nature of our work, this is best done that way for now. Other systems I love using are Evernote for personal note taking and for those moments when I have all those business ideas or thoughts about something and I want to get it all out of my head. I use Google Drive for collaborating with clients and with contractors. Asana is my go-to project management tool for collaborating with my VA, and for writing out tasks for myself. Also, I have recently begun bullet journaling, and I’ve been loving that for keeping track of my daily to-do’s

Since you are your own boss, do you have any advice for maintaining a work-life balance?

Finding my personal and business values was a HUGE first step in making that balance somewhat a reality. I don’t believe in a true balance, but I believe in a more balanced ebb and flow. When I realized that one of my core values was friends and family, that let me know that I absolutely needed to keep room in my schedule for making that a priority. Even when I was working full-time and running Pinegate Road, I still kept the majority of my weekends free to spend time with friends and family. Things were crazy, but I was able to make it happen even during the most stressful times. Now that I’m working for myself, I still keep my core values at the top of my mind, and make sure that I’m filling each of those buckets up in little ways throughout the week. There will certainly be days or weeks where things aren’t ideal — that’s life — but if you find your core values and make them a priority, you’ll find more and more of that balance as you go through running your own business. This is totally a shout out — hah! — but if anyone is interested in finding their own core values, I’m going to have a free course on Pinegate Road that goes over what they are, how you can find them for your life and business, and how you can start using them in your life and business to get to reach your dream future. Going through these exercises has been the biggest thing in me reaching my happy life right now, and so many people ask me about finding them and keeping them a priority in their life and business. I wanted to put this out there so I could stop talking about it all the time like a weirdo, and actually help people work through the process! If you sign up for my newsletter now, I’ll send you more info when that launches. If you’re reading this after December 2016, just head to Pinegate Road, and sign up on the homepage! If you’re not into taking a course, I would suggest doing a lot of free-writing and figuring out what themes come up that make you feel joy. When you do that and notice it, you’re heading in the right direction :)

"If you find your core values and make them a priority, you’ll find more and more of that balance as you go through running your own business."


TOE-site.jpg

The 3 greatest attributes you need to be a freelance creative are:

curiosity, persistence, optimism

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Megan Gilger

This week we have the sincere pleasure of speaking with Megan Gilger of The Fresh Exchange, a blog, studio, and shop, that Megan runs with her husband Mike Gilger. The Fresh Exchange is their thoughts, dreams, reality, and musings. It is the peaceful reserve they go to, the place they dream of when they wake up every morning, it is their life of intentionally simple and beautiful moments.

We are honored that Megan took time out of her busy entrepreneurial and new momma schedule to share such wonderful wisdom. This interview is chock-full of insight; you'll want to read it over and over again!

Megan Gilger | Freelance Wisdom

Can you tell me a bit about your path to becoming a freelance designer?

I began doing design while still in college. I was getting my degree in Media Communications with a focus on Multimedia Design and Studio Management. My goal was from the start to own my own studio. I wanted to do things my way. I was more fearful of working for someone else and being tied down than I was to strike out on my own. From there I made a lot of contacts in the media industry on various internships I did. I took anything and everything from a movie poster for an indie film to a wedding invite to labels for a food company. Anything I could get my hands on. After college, all of the contacts I made payed off. I was able to create a strong base for freelance work. The work wasn’t glamorous though so to fill in the gaps and be even more creative I started a blog and I did some wedding invites for a local wedding planner. I was never someone who was that into weddings, but what it allowed me to do was make a lot of big mistakes. I learned how to value myself and how to manage contractors working with me (aka printers), how to mark-up product, and most importantly build my own contracts and brand.
After about 2 years or so, the blog started taking off. The work was pouring in as people saw my lettering and design style. This resulted in my ultimately bringing my husband into the company. Now, we work together. We do less design work these days and more creative consulting, but that creative space was what launched us into growing a business that inspired us more than just made us hustle.
Fresh Exchange | Freelance Wisdom

"I was never someone who was that into weddings, but what it allowed me to do was make a lot of big mistakes. I learned how to value myself and how to manage contractors working with me (aka printers), how to mark-up product, and most importantly build my own contracts and brand."


Megan Gilger, Lettering, Freelance Wisdom

In the beginning, how did you attract your first good clients?

The blog was the key. Starting that and getting myself out there and using twitter made a huge difference for me. I started landing very open design projects with amazing companies. Doing branding for an iPhone app, labels for a cocktail mixer, and lettering for a food truck. Having my husband as my partner made all the difference in how we continued to do this work.

As Fresh Exchange, you are one half of a design team with your husband. Can you tell us a bit about what it is like to work with your partner?

You know, it is hard sometimes, but I wouldn’t have it any other way. We never wanted to work together. We actually purposely tried not to, but after a while we realized that our skills weren’t so similar and we actually complimented each other similarly. It makes sense knowing we are married, but to us we weren’t sure it was something we wanted to do at all. Now, it has offered us so much freedom. There is a lot of pressure that all of our income is from one entity, but we like having the pressure on us. Some people don’t like that and need more security, but we love the hustle that comes with working for yourself and even more so as a couple. It pushes us to always do more, not just work, but things that inspire us creatively.
Fresh Exchange | Freelance Wisdom

What advice would you give someone who is considering joining forces with a spouse, friend, or colleague to design as a team?

Well there is a ton of advice on our Working Together Youtube series, but I highly suggest beginning by making sure you have the same vision for the company. Spend time making sure you align with where things are headed and be open about your dreams. Talk about what qualifies success for you. I also suggest learning how you each work. Mike and I work very differently in some ways and very similarly in others. We have learned it the hard way, but now that we know, we know how to respect those parts of ourselves.
Fresh Exchange | Freelance Wisdom

"I highly suggest beginning by making sure you have the same vision for the company. Spend time making sure you align with where things are headed and be open about your dreams. Talk about what qualifies success for you."


Freelance Wisdom

You are a relatively new mom, congratulations! How has becoming a mom changed how you work and/or the types of projects you take on?

Oh man, being a mom and running a business makes running a business with your husband look easy and in all actuality it has made running a business with Mike easier in many ways. I never expected that. But it has changed every ounce of who I am both creatively as a human and as a business owner. For a while it was hard to separate myself from mom and my work mentally. I felt in many ways I didn’t want to release the weight of what it is to have a child to anyone else. I felt I was burdening everyone else with him in some way. It was a very weird feeling I never expected. I felt I needed to somehow perfectly find the balance between doing it all. It has been hard on me to realize it isn’t about being it all, but being able to know when to delegate and when to release what you cannot do because it is not allowing you to do other things well, that goes for too much work and too much mom. The balance is hard and I do not believe it will ever be perfect for me. I love my work and I love my son, but I know that my son will benefit by seeing his mother work hard and pursue her dreams as much if not more so than me being there for every step along the way. I thought I would have an easier time with that idea, but it has been hard to release for me. That said, I am still working on this part of my life as a creative. Still working hard on this one every day.

What has been your greatest struggle as a freelancer so far?

My greatest struggle is always wanting to be the best me in every capacity. It used to be that I just wanted to be the best, but I found that was always a let down because being at the top is never a great place to be. Instead, I struggle constantly to find the balance between being my greatest self in every area of my life and giving myself grace when I fail really hard or when I lose touch with reality of what is possible and what isn’t. That may sound vague, but I think as someone who is entrepreneurial there is a natural instinct to achieve and be great at everything. When I had a kid, I realized that thinking great in every capacity of life was possible is just a let down, instead I tell myself daily I have to find a way to just be my best for today. It is hard to remember what that looks like and some days are different than others.
Megan Gilger | Fresh Exchange

"I tell myself daily I have to find a way to just be my best for today."


Megan Gilger | Freelance Wisdom

You do a wonderful job sharing your personal life in a professional space. How does this openness affect your client relationships?

I have found that when you are open, when you are a real human, people find a quick and instant connection to you. I believe the greatest way we can connect with others is by telling our story. We all have one and a story gives us a place to connect with others. Each one of our clients has always found our blog and our story as a point of beginning a relationship with us and not a hinderance. I think it depends on how you want to be with your clients though. Everyone is different, but I like being connected to my clients and feeling like we could potentially be friends especially when we are doing consulting work. I want them to feel open with me and able to ask tough questions. Sharing our tough things, I think, makes the vulnerability happen faster so we can get the core quicker.

As you know well, freelancers are just as much small business owners as we are creatives, what are three tips for managing the nitty-gritty components of your business?

In all honesty, Mike handles so much of this. I tried and I am so so so bad at it. BUT we do hire an accountant, we hire a lawyer, we hire people to step alongside us to make sure we do it all right. We do use a ton of apps and have a Working Together about those tools we use, but setting aside a time each week to do it makes it easier.
Fresh Exchange | Freelance Wisdom

You have built a large and engaged social following, what are your tips for creating a community around your brand?

My theory is you have to live great content to produce great content. People have very high bull shit meters these days, so though creating beautiful things is nice to see, I think people want connection and real stories. I think you can grow a following on making pretty things that are niche, but those are things you will quickly unfollow. To create a following of people who really engage and stick around even through the tough times you have in your life and your business you have to be real and live a life that you truly love alongside it. I think people can read through the lines when you are just phoning it in. That’s my theory. So I try really hard to share things that are both visually beautiful to me and bring me joy, along with real thoughts I am having about life and moments going on.

The 3 greatest attributes you need to be a freelance creative are:

A willingness to learn, A willingness to fail, and A passion for the work you are doing.
Megan Gilger | Freelance Wisdom
Megan Gilger | Freelance Wisdom

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Mandy Lancia

Mandy Lancia is a lifestyle photographer, social media manager, consultant, stylist, and content creator based in Chicago. Although she steps into many different roles, her work remains consistent and her aesthetic calming. With her photographs we are reminded to appreciate movement, stillness, and the beauty of the moment. 

Mandy Lancia | Freelance Wisdom

Tell me about your path to becoming a freelance photographer, stylist, and marketer.

I have always known that I wanted to pursue a career in a creative field. I studied communications and media at Northeastern University, so my courses covered marketing, PR and film production. While in school, I was working for a small plant shop as a social media manager, which allowed me to style, photograph and create content for various media platforms. With a background in event planning and commercial photography, I was able to create a position that allowed for a bit more freedom and creative exploration.
Pretty soon after graduating this past May, I moved to Chicago where I have been pursuing freelance work full time. While my heart still often longs for Boston on occasion, I found more creative realms and markets in Chicago that allow me to find consistent work that I enjoy. I suppose that I never really decided to become a full time freelancer, but the opportunities that I have encountered have put me on this path.

In the beginning, how did you attract your first good clients?

I have always been someone who tries to build relationships with people that I admire. With that being said, I truly admire small business owners with unique and inspiring visions. Many of the clients that I have worked with were not sought out; rather, after visiting shops multiple times and conversing with the owners, I was offered freelance work. Honestly, I couldn’t ask for anything better.
I am a strong believer in small businesses. Growing up with a single mother who owned a shop, I understand the dedication that goes into making a business successful and the steps that need to be taken in order to gain visibility and community. There is beauty in the strength of independent businesses, which is why I tend to work exclusively with small shops and brands that I love.
Mandy Lancia | Freelance Wisdom

What advice would you give to somebody starting out in photography/styling?

Just create. When I began this venture, I didn’t even really know that I began. I loved capturing images with a thoughtful and minimal aesthetic, which then led to a cohesive set of images that portrayed my style and personality. Always keep your eyes open for inspiration, whether it be a friend, a time of day or the movement of light through the window of the coffee shop you frequent. Just always be looking and learning from your surroundings. I think understanding and appreciating movement is of great help when it comes to styling. Even in a still image, the way that the objects, clothing or setting are placed, create an emotional response with viewers. There is a trend of styling beautiful images, but if you want to work in styling photographs, remember to create a moment, rather than just an image.
Mandy Lancia | Freelance Wisdom

"If you want to work in styling photographs, remember to create a moment, rather than just an image."


Mandy Lancia | Freelance Wisdom

Do you have any tips for being your most productive?

  • Make lists and use a calendar. Freelancers can very easily become overloaded, so make sure to keep schedules and agendas to get the most time out of your day, without becoming overwhelmed.
  • Be open and curious. Productivity doesn’t necessarily apply to a specific project. When you are meeting someone new, talk about your interests and skills; while at a coffee shop, ask the person next to you if they are enjoying the publication they are reading. The act of reaching out and creating a relationship can lead to so much more than an interesting conversation. Many of the jobs I have taken on have come from conversing at an event or telling a friend that I am interested in showcasing female business owners.
  • Believe in yourself. In freelancing, you are your brand, your work, your vision.
Mandy Lancia | Freelance Wisdom

"Believe in yourself. In freelancing, you are your brand, your work, your vision."


Mandy Lancia | Freelance Wisdom

Can you tell us about your styling process?

When creating styled work for a client, I begin by asking them what they want their images to convey and where the images will be used. This gives me a sense of the backstory behind the scene I need to create. From there, I decide what products will be used in the shoot (this is my favorite part!) Through touching, moving and visualizing the products and the setting, I can then narrow down to the essential needs of shoot. Depending on the story being told, I then source additional objects to be used (i.e. florals, linens, plants). In terms of the actual styling, it is a fairly fluid and natural process. With the images that are in my mind, I am able to begin the creation, but the rest flows from there. As I have said before, movement is important in my process, so I tend to style objects of different heights, shapes and sizes in order to create a realistic environment.

What has been your greatest struggle as a freelancer so far?

Having a consistent workflow, I would say, has been the greatest struggle. While I have only been freelancing full time for three months, I have seen weeks that are packed full of projects, while others are lacking. Since I am trying to sustain myself and make a living with this work, not having a set schedule can be a blessing and a curse all in one.
Mandy Lancia | Freelance Wisdom

What is your favorite thing about freelance?

My favorite aspect is the freedom that it gives me. I am able to work at any given time, while still allowing for personal projects or travel. I am extremely lucky to have created a career path that I wholeheartedly love. From styling a thoughtful, simple breakfast, to photographing a fall clothing line, to baking a cake for content creation, rarely does my work ever feel like work; rather, they are simply projects that I can fully delve into passionately, which I think comes across in the finished project.

How do you continue to attract your ideal clients?

I truly think that showcasing my cohesive style attracts new clients. Whether it be through my Instagram feed, my website, or my personal project WITH/ANOTHER, people or businesses who are interested in working with me can understand the aesthetic, consistency and work ethic that links all of my projects.
Mandy Lancia | Freelance Wisdom

Since you are your own boss, do you have any advice for maintaining a work-life balance?

Since I do feel super fortunate to have a career that doesn’t feel like work, I don’t necessarily feel as though my work and personal time are that separate. If I was not styling projects for work, I would be doing it for pleasure on my own time anyway. With that being said, it is difficult to turn my mind off from thinking of new ideas, projects or ways to showcase my work. I try to take some time to myself every morning before I really start my day through either a cup of coffee, yoga or simply listening to an inspiring podcast or album while I am getting ready.

The 3 greatest attributes you need to be a freelance creative are: 

Dedication, passion, and curiosity

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