01 / Article

Graduating from small brands to large

Chris Calo
Chris Calo
13 min read

Growing as a creative professional is a daunting task. You need to learn everything under the sun. Keep up with trends to stay relevant. Decipher a smattering of best practices. Be a master of a variety of expensive software suites. And, do it all without creatively shooting yourself in the foot. Factor in business upkeep, financial burdens (such as rent, taxes, or utilities), alongside client outreach, and … pssh, who am I kidding, you're screwed.

Well… no. Hard as it may be to believe, anyone who's successfully freelanced, or started an agency, has been there. You pile on the grunt work. You write small bits of copy, designing logos and fliers on minuscule budgets. You hammer out user-interfaces that will almost never see the light of day. But, how does one work through this mess to be able to do business with the likes of big brands? Are your skills lacking? Do you need years of dedicated service as an underling, before you can take the leap?

Please, plop yourself down for a minute. Let me tell you the story of Vulcan's journey (and by relation, my own) down this path.


Starting out as a freelancer - wow, well-over a decade ago now - was a slow crawl. Growing up in rural New Hampshire, opportunities were slim as it was. Old convenience stores, gas stations, and failing mom and pops were plentiful. Your only hope was to get your parents' employer to hire you for creative work. Otherwise, you had to learn a more in-demand skill.

Stubbornly, I chose both.

The real journey began more than 20 years ago. My dad had owned a printshop growing up, and I, fortunately, picked up a thing or two being there. By chance, I learned some basic software engineering skills from my mother's books. Enough to cobble together PageMaker plugins and command line programs in C on my dad's early-90s Mac. Paired with this, I installed all the floppies (about twenty-two-thousand-one-hundred-six to give a shallow estimate), to get Illustrator and Photoshop running on these 32-bit mammoths. I learned all I could about design, printing, and the inner-workings of these programs.

Illustration of Adobe floppy discs housing saved files

With these skills at my disposal, when my dad sold his shop, I began working at small, local print companies. I also piled on as many courses in art and math that I could . (Despite ignoring it all to work on my own, unrelated projects.) Nevertheless, this gave me solid roots in the business. Instilling a professional understanding of the costs of production, workflows, and communication. Then, almost as soon as I entered college I started trying to find freelance projects. This was a lot harder. My parents, both successful business owners, encouraged this to its fullest. But, at the same time, they emphasised how important it was to figure it out on my own.

After peddling my skills across my small town in New Hampshire, I landed my first opportunity. A pawn shop! And, man, was I underprepared. Thrilled out of my mind! But, underprepared.

This client needed a new everything: a brand, a website, print materials, and so on. I was able to talk to the elderly woman who owned the shop - for what was certainly faaar too long - about all the ins-and-outs of how I would approach this. Gabbing on about granular fixes, campaigns, how it could grow as a business, and so on. Looking back on it, I wish someone filmed it, cause I may piss myself laughing if I could view it today! I was so over the moon about the opportunity, I took into no account the shoestring budget there was to work with. Nor, how much time was needed for this overhaul, or what the client's needs were, in the least. When I finally shut-up, I was able to figure out that all they wanted was a new business card - nothing more.

I was an amateur.

amateur | ˈameder, ˈameˌter, ˈameCHer |


The first stage of growth for a freelance designer, developer, copywriter, et al.

Common traits include (but are not limited to) :

  • the inability to articulate one's skillset, in a succinct, targeted manner
  • a desire to execute, above-and-beyond (or completely void of) the desire to listen
  • a lack of desire or ability to determine profit, in relation to a required time-investment
  • unfamiliarity with being desired in the market; the first opportunity is the "BIGGEST" (or "ONLY") opportunity out there

Starving Artist

This pattern kept up for awhile. I worked with pizza places, community churches, local bands, and bars. The quality of the work I was putting out into the world ever-improving. The pay, less than mediocre, and the hours gruelling. But, I knew this is what I had to do with my life. It only made sense to marry the skills I taught myself as a kid, and grew into in young-adulthood, to form a living. I grew in my ability with each passing day, and the workload was always there. Yet, the pay-off seemed so underwhelming. It's easy to see how most sane people would throw in the towel right here.

I absolutely yearned for what any musician would call a "break." That point where you land one job and it snowballs from there. It came to a point where I would collect (read: steal) menus from any restaurant with a half-reputable brand, at dinner. I would build a collection, emailing the corporate offices of these businesses, one-by-one. My hope was being able to make a personal connection and contribute to what I thought was phenomenal. A brand, in the wild, being so prominently - and in some cases literally - consumed by the masses. Restaurants of clout were my Holy Grail, but… I didn't hear back from anyone. Cold emailing is hard!

Eventually, I found an in. I was desperate to build a better portfolio that I could present to larger businesses. So, a photographer friend and I hit the streets. Now, I don't recommend this, but what we did just-so-happened to work. We went door-to-door, visiting the more-highly rated restaurants in the area. We asked if we could update the photos of their food at no cost to them. (When I was the one doing the talking, I labelled it "culinary photography." Thinking if I made it sound classier our free service would be that much more attractive!) The plan was, he would do the shooting, I would do the retouching.

Illustration: Old hardware, using old app design

As luck may have it, after several afternoons of doing this - we hit it big! Well, kind of. Big for us. The town we were in had a bakery turning 100 years-old that month. And, they were terribly disappointed with the flip-phone quality images on their website. Leaping at the opportunity, I also explained website updates. A bit of planning and portfolio-gazing later, and they were sold. This was my first real client, and I had been freelancing for about 2 years at this point.

My mum would call this condition being a starving artist. Colloquially, it means skilled but impoverished. I would like to also tack the term "delusional" onto the end of that, but with just cause. I firmly believe a little bit of delusion is sometimes required to look past the state you're in. My friend ultimately thanked me for begging he traipse around a boring, tired town with me in the hot sun for several days. As a result, the portfolio pieces were some of our best yet. I believe he still shows them off to this day!

starving artist | ˈstärviNG ˈärdest |


The second, most frustrating, stage of growth for freelance designer, developer, copywriter, et al.

A person in this state is characterised by the following:

  • a desperation to thrive, without a definitive pathway to progress
  • little-to-no working capital, putting all time, energy, and funds into growth
  • a dream, with the skills and work ethic to start realising it
  • more confidence than an amateur, but still more-than-shaky on client relations

Into Proficiency

Ah, how I wish I could say, "…a couple days later, and, ta-da, successful creative agency!" Things gradually picked up from there, but there was still a lot of work and a steep learning curve.

After our photography experiment, my friend took a job elsewhere. We went our separate ways. I spent the next several months creating the bakery's brand. I designed the website. Engineered an API for handling online ordering (entirely new for both of us). Made print material. Created their in-store signage. The list goes on… The end-result was massively successful! Their foot-traffic and the number of daily orders increased by several magnitudes. The client was very happy with the work!

As it turned out, my client's sister bought a candle shop down the street and was busy revitalising it. She was so excited with the way her sister's work turned out, I was asked to do something similar for her business . I designed the brand, created the packaging, designed and implemented a website, and so on. A big referral!

Around the same time as I was beginning this project, I heard from another familiar person. The pawn shop lady's brother! I had spoken with hime before about his business and we lost contact. But, he saw the work I had done recently and was looking to speak with me. Now, in contrast to his sister, this gentleman owned a colossal business. One of the largest woodworking companies in the North-East. When I had met him before, he had explained that he had interest in my work. But, he wasn't quite sure he wanted to move forward with any design or technical changes at that time. This time around, the quality of the work was similar, but he almost immediately signed up for a new web app.

Clients were almost immediately in-reach at this point. So, what changed during these years?

In Retrospect

I often find myself asking that, when I look back on this series of events. My ambition only improved over time. While my skills evolved, and continue to to this day, the leap from landing the bakery to this point wasn't enormous.

The difference was two-fold. I gained confidence in myself, and bolstered the feeling of trustworthiness that I gave off. Mr. Woodworking, in all his experience, could tell I was a little nervous or unsettling in my approach on our first meeting. My portfolio intrigued him, but letting a kid touch his life's work was out of the question. He needed a professional, and I had to fit the bill.


Today, this problem I had getting my foot in the door in a rural area doesn't exist. Quite the opposite. I work day-to-day out of our office in NH. We explicitly set time aside to meet with clients and talk about upcoming projects. We've even extended our repertoire in recent months to bring our offices to Germany and Thailand. This was necessary to better keep up with our clients in Europe and Asia.

At the end of it, a few things we do right that I never would have thought of starting out :

Showcase Results

Yes, maybe your work is already top-notch, but are people buying it? This is likely due to a missing lead between the needed investment, and the return on said investment.

Next time, instead of a "look what I did here, isn't it pretty" try a "look how this performed - do you want to know how I did it?" It doesn't matter if you're an illustrator, copywriter, UI designer, or engineer. If you're successful, you're really an artist selling a service. If you can sell the benefit, you'll have a lot more slack selling the process.


I worked myself to the bone starting out. It strained relationships, affected my health, and it stressed me out more than it should have. The stress of working so hard to get clients compounded the stress I experienced in trying to financially make up for not having said clients. If you're in this position, take a step back and reevaluate your state for a moment.

Prospective clients appreciate a hardworking individual. But, the last thing you need is to seem overworked. Having worked lots of long nights, I can assure you that it is a bit mentally destabilising.

Plan Ahead

What happens when you have 3 large, paying projects and then dead-air for 6 months? Will it shake you to your very core, or do you have a plan and/or supplemental income to stand strong? At first, I didn't realise the need for this. I'd often get a role and tread water while my bank account wasted away. Only to get another client and let the process start again.

For starters, if you want to own a business, this is always a risk. There will be fat months and there will be lean months, but there will always be people to pay - yourself included. If you can strategise well enough to prevent this pattern, you've already been dealt a near-winning hand.

And, yes. Financial planning and upkeep will take time away that could otherwise be spent on client work. Trust me, it's worth it.

Listen More than You Speak

This is something I still remind myself every day. It's not really a "walk a mile in their shoes" kind of thing. It's more of a "you don't know what you're talking about yet" sort of deal. If you're beginning to get confident in your role as a consulting professional - whatever your focus may be - one of the first things that becomes apparent to you is that clients are hiring you for your professional attention to detail. The work they are expecting you to do is work that they cannot do themselves. This, however, does NOT mean you need to be the first person to come up with a bright idea.

I make it a priority to simply sit and listen as much as possible during meetings with clients. Yes, I speak often, but I want to be certain that, when I do, I'm not confusing my thought processes with their needs. It's incredibly easy to walk into a meeting about a prospective client's new application, after coming off a massive project for a large company and think you're immediately ready to contribute something grand to the project. I firmly believe it takes a lot of wisdom and patience to truly hear and dwell-on the ambitions and goals of a client, before imposing your special brand of genius on it.

Having been on both ends of this, it's truly refreshing when a consultant, freelancer, or even a peer or family member is capable of putting themselves in "learning mode" to really understand a problem, before taking action. To a certain extent, it's a matter of compassion. If you care, you put their needs over your desire to do something.

In fact, at Vulcan we believe in this philosophy so much, it's one of our core tenets. Listen more than you speak. And, so far, it seems to speak volumes.