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2014 in Hightail illustrations

It is December, a time to look back on the year that was. Everywhere you look will be lists of the 50 favorite songs, top 10 movies and 47 best Buzzfeed listicles. So we decided to do our own review and revisit our fab Hightail illustrations.

Every week, we email our regular users and the message often features a custom-created image illustrating the feature we’re explaining or offer we’re promoting. Thanks to the creativity of our 2014 illustrators, Austin Petito and Dominic Flask, we can look back at vintage year of funny, stylish and smart images. Enjoy.

2014 Hightail email illustration: tracking

Explaining file tracking

2014 Hightail email illustration: Chinese New Year of the horse

This stylishly geometric horse helped us celebrate Chinese New Year.

2014 Hightail email illustration: return to sender

Explaining return receipts (but what’s the relevance of that West Hollywood address?)

2014 Hightail email illustration: Valentine's Day

On Valentine’s Day, love has no limits (and nor should storage).

2014 Hightail email illustration Death Star

We announced that Professional plan users can share files up to 10GB, which equates to 140 3D architectural models of the Death Star.

2014 Hightail email illustration: animated password

Our first ever animated gif helps explain password protection. Click the image to see the animation.

2014 Hightail email illustration: St Patrick's Day

Celebrating St. Patrick’s Day as if Hightail was an Irish bar.

2014 Hightail email illustration: Guess Who

Use Verify Recipient Identity and don’t just Guess Who has access to your important files.

2014 Hightail email illustration: summer

In summer, use Hightail to work more effectively and get more beach time.

2014 Hightail email illustration: World Cup

During the World Cup our discount offer helped you SAVE.

2014 Hightail email illustration: Final word cloud

Our word cloud highlighted the most-used word used in filenames shared on Hightail.

2014 Hightail email illustration: return receipts

Here are all the things you used to need in order to get a return receipt.

2014 Hightail email illustration: back to school

It’s back to school time with an apple for the teacher and a Hightail discount offer.

2014 Hightail email illustration: Shinkansen express

Promoting Hightail Express: our bullet-train fast app, aka Shinkansen-d.

2014 Hightail email illustration: password cryptex

Know the code with our cryptic password protection illustration.

2014 Hightail email illustration: Swap Ideas Day

Celebrating Swap Ideas Day 2014.

2014 Hightail email illustration: fall leaves

An autumnal scene to celebrate the arrival of fall.

Hightail Halloween illustration

Did you spot the references to classic horror stories in our Halloween image?

2014 Hightail email illustration: passport

Verify Recipient Identity is your passport to control.

2014 Hightail email illustration: Movember

Soup strainer savings with our special Movember discount offer.

2014 Hightail email illustration: Thanksgiving dinner

Celebrating Thanksgiving with all our favorite foods.

2014 Hightail email illustration: Black Friday shopping cart

You’ve finished Black Friday shopping but your cart is still missing Hightail.

That’s it so far in 2014. We have a lot of fun creating these images and hope you enjoy receiving them every week.  Keep an eye on your inbox, or our Facebook and Twitter pages for more great illustrations to come.

Check out our recent interview with one of our illustrators: Meet DangerDom.

Make reporting the news easier

A recent fire at UK power station gave us a great example of the benefit of Uplink. If you don’t know what Uplink is, it’s a great way to help others share large files using the power of your Hightail account. Send your personalized link for a unique Hightail page to anyone and they can easily share files as large as 10GB with you.

Our story took place on Twitter, when a woman filmed a raging blaze near her home contacted local TV station BBC Oxford to see if they wanted to use the footage for their news coverage:

Hightail Uplink Twitter case study 1

The network replied, asking asked her to email the video:

Hightail Uplink Twitter case study 2

The news spread on Twitter like — ahem — wildfire and soon other media organizations were getting in touch:

Hightail Uplink Twitter case study 3 Hightail Uplink Twitter case study 4











But each group expected the woman to email them her video, which proved problematic because it was a large file:

Hightail Uplink Twitter case study 5 Hightail Uplink Twitter case study 6













Only one organization had a simple solution at hand:

Hightail Uplink Twitter case study 8







Rather than expect the woman — who was doing them a big favor by providing free footage — to do all the hard work to get the file to them, news agency Reuters sent her a link to its Hightail Uplink page:

Hightail Uplink Twitter case study 10

Now all the woman had to do was simply upload the file to this web page without worrying about file size limits, storage space on Google Drive or clogging up her inbox.

It’s a great example of how Uplink can help you solve a problem for other people, from clients and colleagues to content providers and competition entrants. If you’re interested in using Uplink to receive files as large as 10GB, check out our Hightail Professional plans.

How has Uplink helped you solve a problem for someone else? We’d love to hear your story in the comments below.

Meet DangerDom

image1-cropIf you’ve received an email from Hightail in 2014 then Dominic Flask’s brilliant illustrations may have caught your eye. The Wichita-based designer and illustrator finishes his stint as Hightail’s unofficial artist-in-residence shortly, so we thought it was time to learn more about the fantastic world of DangerDom.

I enjoy designing for the screen
My work lies somewhere between the worlds of design and illustration and I do a little bit of both. That means I do illustrative work for things like websites and marketing materials but also some design work for things like logos and icons. I work with a range of clients from large to small, local to international and a lot of times my work is around the tech industry.

HIT_WorldCupMost of my inspiration comes from mid-century pop culture
Though I draw a ton of inspiration from mid-century modern design, I love things like cookbooks, brochures, advertisements and other printed materials from the 1950s and 60s. I also have a nice collection of vintage children’s literature that I dive into when I’m feeling stuck on something.

Clean, flat shapes with a colorful palette are all I need
In my early days as an illustrator, I usually ended up applying a lot of textural work, color overlays and other things. I began to feel like I was suffocating the work. As I’ve spent more and more time illustrating, my style has become something that is a lot more thought out and planned using a simple and clear aesthetic.

KeenConBadgesI ask a lot of questions up front
It’s the best way to really understand the problems of the client, the goal of the project and who the customers, consumers or users are. Though each project is different, I generally produce sketches early on in the process before doing anything polished. The majority of my work is with people from other parts of the world so there are more phone calls and emails than face-to-face meetings.

People assume Kansas doesn’t have a creative scene
I’m currently based in Wichita, which has a small town vibe and everyone knows everyone else. There is a nice little community here with a ton of talented people living and working in the area, including my illustrator friend Luke Bott.

A lot of my favorite contemporary illustrators are friends
Besides Luke, there’s Ben Schlitter, Ty Wilkins and Dan and Nathan from DKNG. Besides people I know, I admire mid-century illustrators like Mary Blair, the Provensens and Charley Harper, as well as lesser-known artists like Robert Barry, Jan Harber and Cliff Roberts.

I sit at a vintage drafting table all day

My setup is pretty simple: a scanner, a Cintiq 13″ tablet, my 27″ iMac and a wireless mouse are the tools I use every day. My wife and I have a child, so I try to keep a regular schedule. I usually start with emails first thing in the morning and then kick into any projects that are in the development stages (sketches, research, exploration, etc.) while my brain is still fresh. Afternoons are usually for the button pushing type of work: drawing shapes and applying texture in Illustrator and Photoshop.

You can see more of Dom’s work at his website, his Dribbble page and on most of our weekly Hightail emails. (Or just spend the next hour taking in all the detail on his wonderful map of the world.)


Nine reasons why your designs should start with a sketch

An amended version of this post was originally published on the ocreations blog.

Founder and president of Pittsburgh-based design firm ocreations and Hightail user, Shawn O’Mara tells us why the pencil thumbnail sketch still has a place in the fast-paced world of digital design.

ocreations-thumbnailsI have been in the field of graphic design for what seems like ages. Since 1990, I have been a design student then a graphic design instructor at the Art Institute of Pittsburgh and now I’m a designer, art director and senior partner of ocreations design studio in the south side of Pittsburgh.

I have always been a firm believer that designers need to be able to draw or bring their concepts to life on paper in order to sell their ideas to clients, art directors, designers, photographers and other people in the industry. In the field of graphic design, the most important thing we are paid for are our original concepts. I feel that pencil thumbnails are the best and fastest way to take these concepts from inside your head to a format that others can view.

I wish I had $1 for every quick sketch on napkins, post-it notes, notebooks, notepads and desk calendars I did throughout the years. All of these super rough sketches are unleashed ideas. I honestly believe that if I waited until I developed them on a computer, they would either have been forgotten or become watered down.

If you are considered an artist or painter you are expected to be able to draw. If you are a graphic artist you are also expected to be able to draw. When you are labeled a Graphic Designer does that title make you exempt from the drawing portion of it? In my mind it does not. I understand that the level of illustration and hand skills varies and that is ok. I personally do not believe that I am a fantastic illustrator but I know that I can still get my ideas across to people through my sketches.

The Art Institute of Pittsburgh’s graphic design department hosts a meeting with industry professionals to hear what they would like to see more of in our graduate portfolios. The answer now, more than ever, from these professionals is: “We need to see more pencil thumbnails and original concepts.” I personally was thrilled to hear this because it gave me support for my beliefs.

So for the non-believers who think the idea of pencil sketches is a thing of the past, here are nine reasons why I feel they are a big help:

1. Getting the idea out fast.
2. For a designer to sell his ideas to an art director or team member.
3. For an art director to give fast direction to a designer or copywriter.
4. For a designer or art director to provide direction to a photographer or illustrator.
5. For a designer to get on the same page fast with a client.
6. To get the real idea on paper without the computer dictating your direction.
7. To illustrate different concepts prior to computer variations on an approved concept.
8. To keep the ART in Graphic Artist (sorry had to do it).
9. To keep the client focused on the general concept and not allow them to get hung up on exact fonts, colors or images in the early stages.


If you are going to start doing pencil sketches or if you are already using them, here are eight simple things to consider:

1. Keep your thumbnails in proportion to the actual size of the job.
2. Use good contrast to allow things to “pop”.
3. Do a good indication of type (serif vs. sans-serif, leading, justification etc.).
4. If you do not provide a contact sheet for images, then do a tighter indication of the images on your thumbnails.
5. Try different concepts to reach the client’s objectives and target market, not just variations of the same idea.
6. Use a grid. This really helps on multiple page publications.
7. For thumbnails of multi-page publications, show a cover and two spreads for each thumbnail set.
8. Be original, be creative and have fun.

As the Senior Partner for ocreations I always practice what I preach and provide my designers, photographers and clients pencil sketches when needed. I hope that this post helps get the pencils back out in the field and keeps the ideas flowing.

You can learn more about ocreations at their website or read our recent interview with the firm’s illustrator, Nina Zivkovic.

Customer spotlight: ocreations

ocreations brand logoNina Zivkovic is a graphic designer and illustrator at Pittsburgh design studio, ocreations. With a range of capabilities from branding and advertising to print and web design, ocreations provides local startups and multinational corporations with a fresh and creative look. She talked to us about Process Orange, pool table meetings and the power of Post-its.

We have a unique team of creative experts
Everyone at ocreations brings an individual style and creative edge. It has helped us expand our client base to nearly every market and not just business brands—we’ve worked for special events, festivals and musicians as well. I am lucky to work with such a great group of creative individuals. We constantly bounce ideas off of one another.

Packaging for Pittsburgh Coffee Company

We have our own special creative process
It’s called “Process Orange”:
Open up our eyes and ears to get to know our clients
Research, Plan and Brainstorm
Abstract Thinking, Come up with original concepts
Next Level Design Solutions
Generate production and programming solutions
Evaluate the project’s success.

We have a giant drawer full of conceptual sketches
Logo design for pet charity, Wear WoofWe can adapt Process Orange to meet the needs of each client. Some come to us with a specific vision that we bring to life, while others use our process to create the perfect solution for them. But no matter how big or small the company, we always start out with a creative meeting and sketches. Even in this heavily digital age, conceptual sketches are one of the most important things we do.

We have a pool table that doubles as a conference room
Whenever possible our first meeting with a new client is face-to-face in the ocreations office, which is a truly creative environment. When you first walk in, you see our vibrant orange walls, nearly floor-to-ceiling-high windows, our artwork proudly displayed along with our awards and a couple of puppies sprawled out on the sun-soaked floor. We like to discuss project ideas over our pool table, with music playing the background.

ocreations-pool-table-doorway-between-both-roomsYou can’t always meet face-to-face
We have clients based around the country, while some of our Pittsburgh-based clients prefer to communicate over the phone or by email. Hightail allows us to send over the high-resolution proofs and designs that help us guarantee the quality of the final design. It also lets us keep track of sending and delivery to make sure deadlines are met.

We couldn’t do large publication work without Uplink
Brochure design for AethonSome of my favorite work is annual promotional catalogs, which call for hundreds of high-resolution images to be sent to us. Hightail’s Uplink feature allows our clients to send these files straight to me using ocreations’ Hightail account and cuts out couriering jump drives or CDs and DVDs. It’s an extremely valuable asset and, along with the new Download All button, helps speed up the design process.

I use Post-it notes to stay organized
Every morning I arrive at the office and get greeted by our two incredibly adorable office dogs, Ozzi and Ellie. After I grab a cup of coffee, I start organizing my day to ensure I’m meeting all deadlines. You’ll find Post-it notes strategically covering my desk and I take down notes as I complete a project and put up more as new projects come in.

I love to create a hidden story with my illustrations
When I first started illustrating, I was obsessed with creating realistically shaded portraits. But I wanted to expand my illustrations with a particular style and had always found doodling with a pen to be relaxing and inspiring. So I combined my love for realistic portraits with the simplicity, yet tediousness, of ink. About halfway through, I began experimenting with color palettes and I have not looked back since. My illustrations are much more conceptual based now and I enjoy testing how far creativity and simplicity can go together.

Poster illustration for Art Institute of Pittsburgh Alumni ShowThere’s always something creative going on in Pittsburgh
Transit shelter poster for Word Play! campaignI moved to Pittsburgh from Cleveland five years ago. Both cities have great creative environments but the best part of Pittsburgh is how unique each of its neighborhoods are. You walk one block and it feels like you’re in a brand new place. Southside and Downtown Pittsburgh both have tons of creativity about them. There are so many unique individuals that I’ve had the pleasure of meeting and working with. I’ve illustrated concert posters for the entertainment venue Stage AE and had the honor of working with Fred Rogers Company to design the mainframe and posters for a transit shelter project called Word Play!. It was a fantastic experience and project!

Learn more about Nina at and follow her on Twitter and Instagram. Learn more about ocreations at or follow them on Twitter.

Go guerrilla! Five unorthodox ways to market your brand

An amended version of this post was originally published by Entrepreneur.

Before a million pails of cold water brought the disease to global attention, many people had never heard of amyotrophic lateral sclerosis, or ALS. But after a summer of ice bucket challenges, the devastating motor neuron disorder now has an astonishing level of awareness. Though the campaign didn’t originate as a deliberate marketing strategy, it’s a great case study of the power of guerrilla marketing in the social media age.

Inexpensive, small scale and non-traditional marketing tactics can be extremely effective ways of promoting your brand if the idea catches the public imagination and goes viral. But so-called “guerrilla marketing” covers a huge variety of activities, from PR stunts to viral videos. To determine if there’s a tactic that will work for your business, consider these five tips for crafting an effective guerrilla marketing campaign that will resonate with your target audience.
1. Have a hook
If your product or service is something people don’t ordinarily care about, you need to give it an attention-grabbing hook, like the ALS ice bucket challenge.

Dollar Shave Club made the hardly earth-shattering idea of mail-order razor blades really engaging with a hilariously offbeat and low-budget YouTube video. Within two days of launch the commercial went viral, generating 12,000 new orders.

Or try connecting with people in unexpected ways, like this fitness company ad that appeared on German subway trains:handle03







2. Be provocative

Controversy sells so if you’re willing to break taboos and speak truths that people usually prefer to ignore, you can turn heads. This is a common tactic for charities and non-profits, like these visually arresting ketchup packs created by Campaign Against Landmines:


Hightail-cronut-resizeHightail has indulged in the occasional provocative, but fun stunt. We once handed out free cronuts to attendees at a competitor’s annual conference. The pastry packaging came with step-by-step instructions, including “Discard Box”. It was a playful and controversial (we were kicked out of the venue) way of targeting a very specific audience.

3. Sell an idea, not a product
As a start-up, your passion for what you do and vision for changing the world is incredibly powerful. Stating that vision boldly and selling your product based on emotional appeal, not rational argument can give you an advantage.

Salesforce did this brilliantly with its “No Software” logo that evangelized the company’s underlying vision of simple, inexpensive, cloud-based services rather than focusing on what its product actually does. I still remember Marc Benioff’s ad in which a fighter jet shoots down a biplane. Though it was a little cheesy, the image represented a powerful idea that ultimately lived up to the analogy.

You don’t have to be starting out to harness the power of ideas. IKEA celebrated the 30th anniversary of its popular Billy bookcase by filling 30 of them with books and placing them on Bondi Beach in Australia. Beachgoers could swap a book for one of their own or donate to a literacy charity. By focusing on the popular beach pastime of reading, the furniture company got people’s attention while still promoting its product.


4. Make it tangible
Physical manifestations make for great guerrilla marketing. Translating your idea into an object or event can help explain a product, especially digital services.

A Westfield shopping mall in California installed a real-life Pinterest board to act as an interactive store directory. Though Pinterest didn’t initiate the idea, by approving the use of its logo, the company got a great real-life demonstration of its online service.


Even better, if you capture your physical-world tactic and share it online, you can get a viral multiplier. Adobe cleverly achieved this with a bus stop prank in which they Photoshopped waiting passengers into an adjacent digital billboard in real-time. The “Candid Camera” appeal of this stunt has garnered it 22 million views on YouTube.

5. Take a risk
Some of the best ideas sound unbelievably dumb on paper (and may still, in fact, be dumb when you actually do them). They may flop but you won’t know until you try. Many guerrilla campaigns get attention precisely because they are unusual, outrageous or unconventional. So don’t worry about people laughing at you.

Ride sharing service Uber has promoted its service by delivering ice cream to customers. In December 2013, Canadian airline WestJet asked passengers boarding a flight to Calgary what they wanted for Christmas then delivered these gifts when they landed.


Whichever style of guerrilla marketing campaign you devise, remember to document and publish everything. Most guerrilla marketing is by its nature small in scale but it’s the shared links, laughs and likes that will make your campaign a big success.

Which is the best guerrilla marketing campaign? Share your favorites or ideas your company has tried in the comments and let’s inspire others to go guerrilla!

Privacy policy update

We recently updated our Privacy Policy and want to ensure you are aware of what’s changed. You can find the full policy here, while this post highlights what’s new and different.


  • Hightail is now certified by Asia Pacific Economic Cooperation Cross Border Privacy Rules System, but now that we’re buddies we can call them APEC CBPR.
  • Our global privacy certifications now cover all our apps as well as our website.

Info collected by Hightail 

  • Our apps may send you push notifications on occasion, which involves collecting information about your operating system and other details. You can turn off these notifications if you wish (though we’ll ensure that they’re always useful so hopefully you won’t want to.)
  • If you log in to Hightail or import contacts using OpenID providers like Facebook Connect or Gmail, a new subsection Social connectors outlines our policy on this.
  • Previously, our policies around Information collected by third parties were scattered across various sections. They’re now gathered in one appropriately titled subsection with some minor tweaks for extra clarity.

How we use and share information

  • Here we just added “email delivery” to the types of service providers we use and made a minor language edit about Retention and deletion of your information. Both of these changes are intended to give you extra clarity.

That’s it. Legal talk over. We can all relax now.

Happy Halloween

Hightail Halloween illustration








We’re celebrating Halloween with this spooky illustration, created for us by the talented Danger Dom.

Some of you have already spotted the references to classic horror stories in the image. If you want to test your gothic knowledge, send us a tweet with your guesses. Otherwise…SPOILER ALERT…the answers are below.

Hightail’s Halloween illustration references

  • Silver bullets – The Howling (werewolf story)
  • Chains – A Christmas Carol (not strictly a horror story, but it does feature a lot of ghosts)
  • Feather – The Raven
  • Screw – The Turn of the Screw (yes, it’s a cheesy reference)
  • Ring – The Jewel of the Seven Stars (Egyptian mummy story)
  • Bolts – Frankenstein
  • Locust – The Abomonible Dr Phibes (a lot of people thought it was the moth from The Silence of the Lamb which was a good guess)
  • Test tube – Dr Jekyll and Mr Hyde
  • Stake – Dracula

Happy Halloween from everyone at Hightail.

#HightailTherapy: day two deliveries

Our campaign celebrating the ad, marketing and creative professionals working to keep their clients happy continues. Below are some #HightailTherapy deliveries that we made on day two.

Don’t forget to share your agency’s story to be in with a chance of winning one of today’s deliveries.

Reliabubble new car 

Creative agency ATTIK got very excited when one of its auto clients, the Toyota Scion xB, was named Consumer Report’s most reliable new car…

Screen Shot 2014-10-30 at 2.25.55 PM





We figured a celebration was in order and wondered how many bottles of champagne would fit in a Scion…

Screen Shot 2014-10-30 at 2.28.00 PM

And the ATTIK team will no doubt have celebrated even harder after the Giants claimed another World Series…

Screen Shot 2014-10-30 at 2.28.13 PM

Blah and order

The creative minds behind Virgin America’s inspired Blah Airlines campaign deserve a little something to fire more great ideas…

Screen Shot 2014-10-30 at 2.29.31 PM

Eleven Inc.’s reply was typically inventive…

Screen Shot 2014-10-30 at 2.29.54 PM

High res hijinks

Sometimes people want something a little more practical than scotch and bubbles, so we’ve also been giving away free Hightail Professional plans for funny client stories like these from Canadian marketing agency founder Darrell

Screen Shot 2014-10-30 at 2.30.42 PM Screen Shot 2014-10-30 at 2.30.58 PM

And New Jersey-based designer and doodler, Lily Ann

Screen Shot 2014-10-30 at 2.31.14 PMScreen Shot 2014-10-30 at 2.31.35 PMScreen Shot 2014-10-30 at 2.31.23 PM

What’s your story? Tweet us and you could win a fun delivery to your office today.

See all the action from day one.

#HightailTherapy: day one deliveries

All this week, we’re running #HightailTherapy, a campaign that celebrates the advertising, marketing and creative professionals working hard to keep their clients happy. We want to hear your agency’s stories about all-night brainstorms, ridiculous client requests and those moments when you got to _FINAL. The best stories will win a delivery of food, drinks or other sweet treats.

Here are some of highlights of the fun deliveries we’ve made so far:

Together we are giants

When the team at ad agency BBDO SF tweeted their support for the San Francisco Giants after game five of the World Series…

Screen Shot 2014-10-29 at 11.49.17 AM

We decided to help them enjoy game six…

Screen Shot 2014-10-29 at 11.52.14 AM

They seemed pretty happy with the keg of Anchor Steam we delivered…

Screen Shot 2014-10-29 at 11.40.19 AM

Just a shame the Giants didn’t win. Still, there’s always game seven…Go Giants.

Stuck on hold

We noticed that Sarah Mitus, social media account exec at Edelman Digital was looking for help from another file sharing service…

Screen Shot 2014-10-29 at 11.59.37 AM

We thought we’d make her wait for their response more pleasant by delivering cupcakes and flowers from “her not-so-secret admirers at Hightail”…

Screen Shot 2014-10-29 at 11.59.44 AM

Looks like she enjoyed our gifts, though unfortunately hadn’t heard back from that other company…

Screen Shot 2014-10-29 at 11.59.53 AM

Feline good right meow

Evolution Bureau announced that it had been nominated as Best Agency for Social Media at this year’s iMedia Agency Awards…

Screen Shot 2014-10-29 at 12.06.24 PM

Which we thought was worth celebrating…

Screen Shot 2014-10-29 at 12.07.57 PM

With a custom-made cake featuring the star of their recent campaign for a cat food brand…

Screen Shot 2014-10-29 at 12.09.33 PM 2014102895155706-crop


Burning the midnight oil

We saw the lights were on late at creativity agency Mekanism’s office one night…

Screen Shot 2014-10-29 at 12.16.27 PM


Screen Shot 2014-10-29 at 12.16.42 PM

If your agency is in need of some #HightailTherapy, tweet your best story and you could win a delivery to your office today.

See all the action from day two.

How to have a happy client: eight secrets from an agency insider

Having happy clients is the raison d’etre of a creative agency. Quality of work is the ultimate determiner of satisfaction, but along the way the creative process will place obstacles in the path of good relationships.

Managing these is a murky mix of art and science, especially when dealing with demanding or difficult clients, but our source at a well-regarded creative agency (who wishes to remain anonymous) revealed their eight insider tips for keeping clients happy.

Table Stakes1. Make them listen to themselves
“The golden rule of any client interaction is: listen. But I add a twist to this. Once I’m done listening, I repeat what I’ve heard. Making a client hear what they’ve just said is invaluable. Not only does it ensure I haven’t misinterpreted anything, hearing their brief explained by someone else often highlights potential issues. I prefer my clients to recognize problems themselves, instead of me having to point them out.”

2. Never reject their bad ideas
“When a client says ‘my idea is to …’, my instinct is to point out why their hysterically awful suggestion won’t work. Instead, I take notes and say something like ‘we’ll add it to the list’. When I return with our (hopefully) much better ideas, they probably won’t mention it again. If they do, I say it didn’t quite work. They’re usually happy that I considered it and I get bonus point for being receptive to their ideas.”

3. Don’t make delivery promises straight away
“Clients want immediate delivery date commitments. As much as I’d like to conclude meetings with a firm, ‘yes we can’, I always check with my team first. Not only does this show that we take deadlines seriously, the next time the same client rings with an urgent request, I can buy time before committing. It’s amazing how many must-have-it-tomorrow emergencies dissipate within hours of the initial request.”

4. Explain the two out of three rule
“Clients will always want you to produce award-winning work in less than a week for next-to-no money. The most demanding won’t even understand why it’s not possible. I usually find that explaining the ‘two out of three’ rule helps:

You can have it fast and great, but not cheap.
You can have it fast and cheap, but not great.
You can have it great and cheap, but not fast.
You can never have all three.”

5. Never present ideas you don’t love
“It’s tempting when preparing a campaign ideas presentation to add one more to mix. I sometimes think that including a not-so-great idea highlights the effort we put in or will make our other suggestions look stronger. But what if the client picks the wrong concept? We’re stuck producing our own dumb idea. If our main ideas are good enough, that’s all we should need. If they hate them, we can still fall back on the reject.”

6. Don’t assume you’ll find ‘it’
“‘I’ll know it when I see it’: seven words that strike terror in the hearts of creative professionals. If a client doesn’t like our idea but can’t explain why, I never assume that we’ll just hit the mark next time. Them not knowing what they want is my problem so I’ll spend more time with them exploring other work they like. This helps me get inside their heads and closer to finding ‘it’.”

HappyClient-GuessWho7. Know who actually has final approval
“The final seal of approval may not come from the person you deal with every day. Marketing managers have CMOs, CMOs have CEOs, so I always establish exactly who is the ultimate authority before proceeding with an idea. People usually hate showing rough sketches to their boss, meaning we may need to flesh out one or two elements in advance. But ensuring your campaign avoids a last minute thumbs-down is worth our time.”

8. If all else fails, raise your rates
“Most clients are a joy to work with. Hopefully these tricks will help you deal with the most challenging parts of the creative process and leave you with a happy client. But sometimes, you just know that someone is going to be impossible to work with. If simply turning down the work is not an option, raise your rates by 20%. At least then, you can console yourself with cash during another long weekend of last minute revisions.”

Those are our agency insider’s eight secrets for keeping their clients happy. What are your tips for ensuring your clients always come back to you with more business? Let us know in the comments below.

Customer spotlight: Tim Williams Illustration

Tim Williams - a self-portrait

Tim Williams – a self-portrait

Tim Williams is an Atlanta-based illustrator whose work for ad agencies, magazines and children’s books have won him seven Addy Awards and a National Award for Magazine Cover illustration design. Hightail spoke to him recently about developing a smooth creative process with clients and why he feels like he’s being paid to eat ice cream.

I’ve been freelancing for over 30 years
I started out as an illustrator/designer for Ted Turner’s billboard company in downtown Atlanta. When I went freelance, I did a ton of marker comps for Atlanta ad agencies and magazine editorial illustrations. As the magazine industry started to die off over the last few years, I’ve moved into illustrating children’s books for several different publishers…over 30 by now. Plus, I’ve done illustration work for all three of Atlanta’s pro sports teams.


Others can tell when an illustration is mine but I can’t see it
I don’t think I have a recognizable style. One day I’m doing cartoons or caricatures, the next might be tight realism and the following day a loose, sketchy illustration. It’s difficult for me to pinpoint how my style has evolved. When illustration went digital, I had to teach myself how to work on my Mac. The challenge was for me to make it look like the illustrations were still handcrafted.

  Illustration of 1940's style detective for a paperback book cover.

Illustration of 1940’s style detective for a paperback book cover.

Being paid to draw is like being paid to eat ice cream
I can’t count the number of times a new client has come to me with a story of having just dealt with a difficult illustrator. I’ve never understood that. You’re getting paid to draw so be professional, do what you say you’re going to do and meet your deadlines. Part of my success as a freelance illustrator comes from simply being friendly and confident when dealing with clients.

Listening to your client is key
If you are a working illustrator and aren’t paying attention to what your client is telling you, you’re making extra work for yourself. In the long run, you won’t have any clients at all. When I first started freelancing, it was almost all face-to-face conversations with a few phone calls. That rarely happens now. New clients often find me through my website and contact is usually through email.

The files I create can be up to 100MB
This size file is too large and takes too much time to send via regular email. Hightail allows me to quickly and efficiently send illustrations to all of my clients with no headaches. One of my goals when I started freelancing was to make the creative process as smooth, client-friendly and productive as possible. Hightail helps me achieve this goal on a daily basis.

Tim's wet and dry rooms in his home studio

Tim’s wet and dry rooms in his home studio

I have a dry room and a wet room
The dry room is where my iMac, Wacom tablet, reference books and awards are. My wet room is for my drawing board, paints, projector and reference books. I’m usually at my computer by 8AM to check my emails for any overnight communication from clients that need a response. After that I get right to work. Most of the time I have multiple projects going on, which means allocating a set amount of hours to each one. Because of the volume of work I have in my studio, I frequently work into the evening.

Running is great for inspiration
On most days about an hour before lunch I go for a run. It clears my head and quite often gives me ideas for illustrations. I also listen to music. Amy Winehouse is a new discovery for me, so I put her on and that gets me inspired.

The life of a freelance illustrator is somewhat solitary
My studio is in my home, which is about 50 miles north of Atlanta, but pretty frequent trips to the city’s High Museum of Art and other galleries and art fairs keep me inspired and connected. I also just attended my first Society of Children’s Book Writers and Illustrators meeting and enjoyed that interaction.

I like virtually every other illustrator
I can see something in just about everyone’s work that I admire, though my biggest influences are: the great animators from the old Warner Brothers cartoons; N.C. Wyeth; Norman Rockwell; the classic MAD magazine artists, Mort Drucker and Jack Davis; the great caricaturist, Al Hirschfeld.

Check out more of Tim’s work on his website and follow him on Twitter.

Illustration of Audrey Heburn for Turner Classic Movies Hightail7

Seven tips for escaping your creative rut

The lightbulb won't go ping. We’ve all been there. The place where a creative task seems so obstinately unsolvable that staring at your screen or a blank sheet of paper is no longer helping. When you find yourself stuck in that seemingly inescapable rut, try these seven tips for rediscovering your creative spark.

1. Go for a walk
Regular exercise is the surest way to keep your brain at its peak. While aerobic workouts like running and swimming are great for your long-term cognitive power, a recent Stanford study shows that walking boosts creative inspiration.

You don’t even need to ramble across lush green landscapes to feel the full effect. According to the research, people walking indoors on a treadmill showed the same creative problem solving ability as those who were outdoors. So the next time you’re stuck in a rut, get away from your desk and let your feet do the thinking.

2. Get clean
Woody Allen once said, “In the shower, with the hot water coming down, you’ve left the real world behind, and very frequently things open up for you.” Of course, the inspirational power of a shower remains scientifically unproven and 30 Rock boss Jack Donaghy’s explanation involving “the anterior superior temporal gyrus” is, like the character, entirely fictional.

But time spent standing still in flowing water is time without our ubiquitous electronic devices, so, aside from cleanliness, your daily shower also provides rare, distraction-free thinking time.

3. Devour popular culture
Award-winning photographer Chase Jarvis recommends finding inspiration in “the work of other artists, movies, books, magazines”. When faced with a creative block, go to a gallery, see a movie or pick up a book and see how other people have solved different creative problems.

It can also be useful to get away from the kind of work you do, so if you’re writing, check out visual work and if you’re designing, do something more literal. You never know where your next great idea will come from.

4. Start a morning ritual
According to Mason Curry, the majority of history’s greatest creators were morning people. For most of us mere mortals, mornings are a battle against snooze buttons, half-dressed children and grinding traffic, making that brain-fresh feeling decidedly stale. A good way to revive your imagination is to perform a short morning ritual before you start work.

Beethoven used to hand count 60 beans as he prepared his morning coffee. David Lynch does 20 minutes of transcendental meditation. Even just sitting at your desk thinking before you switch on your computer can help clear the detritus of the dawn rush and get your creative mojo flowing again.

5. Impose a restriction
Will Turnage of digital agency R/GA believes you can “enable creative thinking by embracing arbitrary constraints”. If you’re stuck on a problem, try removing a tool from your kit.

If you’re a designer, sketch everything by hand. If you’re a filmmaker, remove all dialogue from your scene. If you’re a writer, impose a word limit, like Dr. Seuss writing Green Eggs and Ham to prove that he could use only 50 different words in a book. Arbitrary restrictions can help you look at a problem differently and find solutions you may not have considered before.

6. Take the process out of creative process
It’s tempting to delay tackling a creative problem by turning to the more mundane, process elements of your job. But actress and writer Felicia Day likes starting her day with creative tasks as it “makes me feel that CREATING is my job, not answering emails”.

When it is time to share ideas, collect feedback and manage clients, ensure the tools you use make things simpler. Don’t deplete your valuable grey matter figuring out software even more complex than the creative problem you’ve just cracked.

7. Get back to work
All these ways of distracting your focus from the creative problem at hand in the hope that inspiration will strike are useful, but as painter Chuck Close once said, “Inspiration is for amateurs, the rest of us just show up and get to work.” Sometimes you simply have to sit at that intimidating blank canvas, sketchbook or laptop screen and do what you do best.

Hopefully these tips will help spark the little bit of inspiration you need to drive the 90% perspiration that all great ideas require.

We’d love to hear some of the ways that you get yourself out of a creative rut — feel free to tell us your story in the comments below.

Seven ways to stay focused and productive

People have many different ways of working. Some thrive in organized chaos, others like clear space and clean lines. Some are old school pen and paper types, others always have the latest productivity app. But however individuals choose to work, having a system in the first place is the key to productivity. To find out more, we asked seven Hightail employees about the systems, structures and idiosyncrasies that help them get their jobs done.

As Executive Assistant to both Hightail’s CEO and VP of Communications, Amanda Roche has to prepare for urgent requests, meeting changes and complex calendar planning every day. To stay organized, she tends to work exclusively in Microsoft Outlook.

“I’m an Outlook power user”, she smiles, “I use all the folders and flagging features to ensure information is categorized and readily accessible. Keeping everything organized allows me to schedule more efficiently and to make changes quickly, if need be.” Amanda also makes sure she gets away from her desk frequently for small breaks. “Even just walking down the hall to go the printer or grab a bottle of water from the kitchen helps me stay focused throughout the day.”

Aaron Martin is Hightail’s Creative Director, a role that involves a significant amount of design and creative work as well as managing a team of other designers. It requires careful time management so Aaron splits his day up into chunks.

“The first part of my day is open,” he explains. “Meetings, design reviews, whatever, I’m available. But the second half is my time. That’s when I’m strictly designing and creating.” Aaron stays on top of who’s working on what using Trello, an online app with a more visual approach to project management service. But he isn’t a stranger to a pen and notepad and finds hand writing notes is more efficient.

For Aaron, staying productive also involves not working. “For every 90 minutes of work I complete, I take a 20 minute break,” he adds, “and maybe a bowl of Captain Crunch cereal.”

It’s all too easy for Matte Scheinker’s day to be a blur of back-to-back meetings. That’s why Hightail’s Chief Product Offer schedules time on his calendar to simply sit in front of his computer and get things done.

“Whether in my personal life or at work, I believe the best way to be productive is to conquer one small task at a time,” he says. “It helps relieve stress because you’re always making some progress. Blocking a meeting-free hour in my day ensures I have the opportunity to get to these tasks. I also create hour-long playlists that I listen to while I’m working, which keeps me focused.” Matte is one of those old school pen and paper types, preferring to jot ideas down quickly and make changes on the fly.

Accounting Manager, Pallavi Gandhi oversees all things financial for Hightail’s customers and employees. She has many small daily tasks that she needs to accomplish and uses Outlook to stay organized.

“I send meeting invites to myself as reminders to do certain tasks,” she says. “When I’m getting through my lists I like to listen to Bollywood music to keep me going. Taking breaks from my computer screen helps me retain focus, so I’ll go for short walks or chat with people throughout the day.” Pallavi is also a committed hard copy adherent and keep folders with the current year’s invoices and bank statements on her desk for quick and easy access should an auditor coming calling.

Surprisingly for a Sales Account Associate, Nick Zambruno is not a fan of Salesforce. “I don’t like that anyone can add tasks or change a customer’s file,” he explains, “I prefer to have total control over my stuff.” Nick’s role involves frequent meetings with customers and prospects so his day revolves around his Outlook calendar. Mornings are critical for Nick as he covers the US east cost.

“First thing each morning,” he says. “I check my schedule to see who I’m meeting with that day and then I’ll search my email for previous conversations with each prospect so I’m completely prepared for these meetings. Finally I review all my post-it notes and to-do lists from the day before to see what calls I need to make in between meetings.”

With all the post-its notes and white board to-dos, others in the sales team like to joke about how disorganized he is, but Nick thinks it’s more organized chaos. “My desk is a mess, but I know where everything is.”

Hightail’s copywriter Colm Larkin works remotely from his home in the UK, which brings its own productivity challenges. “When you’re not leaving your house to go to an office every day, you have to be very disciplined,” he says.

To keep him focused, Colm relies on Microsoft Excel. “I have a spreadsheet with the day split up into 30-minute chunks,” he explains. “Every morning I plan what I will work on and when and this controls my day.”

Being eight time zones away from the rest of his team in California has its advantages. “Though I wake up to a full inbox, I don’t need to respond immediately as my California colleagues are no longer online. This means I can get stuck into my biggest task of the day without getting distracted by email requests and messages.”

You say “toe-may-toe,” Alissa Dos Santos says “pomodoro.” The Hightail Product Marketing Manager uses the Pomodoro Technique to increase her productivity.

“Pomodoro basically involves devoting 25 minutes to focus on a task with zero distractions. Then you take a five minute break,” she explains. “To help with this, I block off time on my calendar so people can’t schedule meetings with me.”

Alissa is always interested in finding other ways to increase her productivity and has recently started meditating every morning before work using an app called Headspace. “I like to experiment,” she says. “So far, meditation has been a huge help in keeping me focused during the day.


These are just a few ways that Hightailers organize their day and stay productive. We’d love to hear how you get things done so feel free to tell us your story in the comments below.

We’re #HighlyInspired by: Eleonore Constant

Hightail is celebrating our favorite photography on our #HighlyInspired Tumblr page. This month’s guest artist is LA-based Eleonore Constant. We chatted to her about taking photos on her phone, always being curious and living in the present moment. 

eleonore contant

How did you first get into photography?

One day when I was about seven years old, my mom asked me to take a picture of her. She thought the picture looked great and that’s how I started taking photos. The more I took, the more addicted I got. I also really enjoy learning and practicing to get better at what I do.

Who is your biggest photography inspiration?

I usually try to find inspiration in whatever surrounds me. So when I go on a walk, I try to be mindful and if I feel inspired by something, I take a photo of it. I also love the work of these LA photographers: Pete Halvorsen and Dylan Schwartz.

Describe your style of photography

I have no idea how to describe my style but all my photos are taken and edited using an iPhone.

Why do you like shooting at the beach?

I like the beach and the ocean. They are powerful and calming. Being there helps me live in the present moment and forget about negative things.

Describe your ideal vacation?

My ideal vacation would be if I could maintain an ideal state of mind. No matter where you are, if you are at peace with yourself, you can enjoy life at its fullest. You could be in the most beautiful place in the world and still have the worst vacation if you are in a bad state of mind.

What else inspires you?

I don’t know where my inspiration comes from. I have always been very creative, whether I’m coming up with new business ideas or creating something with my hands. I am curious, I ask a lot of questions and I try to look at what surrounding me as if I was still a child.

Where can we see your work next?  

You can see my work on Instagram and Tumblr. I’m also on Twitter and I create huge playlists of songs I like on Soundcloud.