Monday, July 15, 2013

How a Skateboard Can Get You a Job [First Job Profile]

Have you ever wondered what it might be like to wear jeans to work, write on the walls, and have your creative ideas influence millions?

Meet Will Gay, Creative Director at Disney’s Yellow Shoes and the man who helped lead campaigns such as and the iconic campaign featuring YouTube videos of real families surprising their kids with a Disney vacation.

I recently sat down with Will; he shared invaluable advice on how to make it in the creative field, what you can do to get the attention of high-level professionals, and how a skateboard can help you get a job. His story is also jam-packed with with vital lessons for your future career success. 

What was your first job out of college and how did you get it?

Before I graduated actually, I called a bunch of agencies, and didn’t ask for a job directly. I just said I was looking to learn more and that I wanted feedback on my portfolio because I respected that particular person and their position. During my senior year of college I landed a salaried job as a Junior Art Director at one of those small agencies I had contacted.

[Lesson 1: Reach out to people at companies you want to work for.]

What was the most important thing you learned from your first job?

When you’re young you often think you know it all. I did, and at my first job I actually got fired after two years. I pushed hard for good creative work and fought my boss and others in all the wrong ways to get it done. When they lost a big client, I was the first to go.

I learned that there is a right way and a wrong way to fight for your ideas. I was humbled early on.

What did you do to leverage your first job to help you get where you are today?

Even though the first job ended badly, I had worked hard to develop a good portfolio and within three days I got a job with another agency where I got along really well with my boss and started to realize there was another way.

After doing some work there I was recruited by an ad agency in Orlando. However, it seemed I hadn’t fully learned my lesson quite yet.

I clashed with my boss again and found myself fighting for my ideas in the wrong way. I thought I was “irreplaceable” and when they lost a big client, again, I was one of the first to go.

[Lesson 2: Learn from your mistakes.]

This time I was out of work for eight months, which was one of the toughest times in my life, wondering how I was going to pay my bills.

I started freelancing for two agencies, one more well-established and another not so well known in the creative world. Both offered me a job, but I decided to go with the lesser known shop. I wanted the challenge, and I loved it.

We won a ton of awards and during one of the annual Orlando award ceremonies Disney was there and recruited me. I loved my job growing the ad agency I was at, but when Disney comes calling it’s hard to say no.

[Lesson 3: Choose opportunity over salary.]

What did you do to make sure you were prepared for each new opportunity?

You realize in hindsight that the journey and the struggle are often part of something bigger. Each thing taught me an important lesson I took with me to the next stage of my journey.

If I had gotten recruited at Disney too early I wouldn’t have been able to survive. I try to tell people to not try to rush it too much. And I’ve learned that if you always strive for great work and focus on that, the money will usually follow you.

What motivated you to work so hard?

I always wanted to try to do better work at each job, and always strive to do something different. You definitely have to be patient though to make break throughs.

You can’t be a rock star straight out of school. Some people can, it happens, but most people have to be patient and go through that slow step-up process and keep trying to do better things to get a better job.

When I went through a tough unemployment time after college I was really inspired by the story of Walt Disney losing everything he’d worked for in his first animation business, and then as he rode on a train, feeling depressed, he drew this little mouse that started everything.

Exactly. Walt drew Mickey during the worst time in his life. It’s so important to embrace those tough times. If you’re open and not afraid to keep trying, a mouse could pop into your head on a train.

What advice do you have for recent graduates who are struggling to find their first job after college?

Don’t get discouraged too easily.

The key is to be persistent and try to get attention in a unique way. Do something that is the opposite of what everyone else is doing – it’s the only way to stand out.

For example, so many students email me their digital portfolios, so what really stands out now are the things I get in the mail.

[At this point Will excitedly goes to his desk and pulls out this small sketchbook.]
The sketchbook cover.
This is a book someone made and mailed to me titled “15 Fool Proof Plans to get my feet in the door and into a brand new pair of Disney’s Yellow Shoes.” 
The inside page.
And at the end of the book (which was filled with off-the-wall cartoons of how she would ‘sneak into’ Disney Yellow Shoes offices, one of which is below) she hand-wrote the link to her portfolio.

It was obvious this took time to make, and it wasn’t something she could send out to everyone. It was creative, fun, personal, and irreverent. It showed she really wanted to work here, but more so, it also demonstrated the kind of skills needed in the creative industry.

She works here now.

[Lesson 4: Really get to know the companies you want to work for and personalize your approach.]

What advice do you have for grads who want to reach out but aren’t sure how to get the attention of someone in a way that would work for their desired industry and skill-set?

Know your audience and do your homework.

[Will gets up excitedly again to show me a skateboard. I’m confused for a second and then he turns it around to showcase a professional and artistic resume.]

I got this from someone who wants to work in our graphic retouching department. He found out through my blog that I skateboard and like to recycle my skateboards by painting over them.

[He then shows me the bottom of the skateboard where it says essentially “please recycle this board and paint over it.”]

Just like the small notebook, it was very personalized.

What should students avoid?

In the creative field, they should avoid having too many things in their portfolio. You have to self-select; otherwise it seems like you don’t have a point of view.

I also hated when people told me my portfolio was ‘great’ but then never called me back for a job. Students should ask for feedback.

After a recent event at a local university I had a student who asked me if he could walk me to my car. “I’m desperate,” he said, “I can’t get an internship and I need one for my major; I don’t know what’s going on.”

I usually try to leave these events right away so I can have dinner with my family, but I saw the fear in his eyes. I asked him to email me his portfolio.

[Lesson 5: When reaching out to people, don't be afraid to be vulnerable. It shows you care and will get their attention.]

The next morning I received an e-mail from him that had been sent 10 minutes after we talked.

[Lesson 6: Follow up with people immediately. It shows you're serious.]

I went through his portfolio and saw quickly it was not at the level where it needed to be. I invited him to come into the office to discuss it.

Remembering the lack of feedback I received and wished I had in my early years, I was very honest with him and told him what he needed to change.

The next day I got an e-mail with his new portfolio. He had taken my advice; I told him it was great and he told me he’d be sending it out that day.

A week later I got an e-mail from him [Will’s eyes start to water as he says this]…this is so recent I haven’t really talked about it. He e-mailed me and told me he had two internship offers with really great ad agencies and thanked me profusely for my help.

[Lesson 7: Act on good advice from professionals you admire immediately and follow up with a big thank you.]

It makes me tear up because I wished someone had helped me like that – it’s so hard. It made me think about the time I was looking for a full time job and some feedback how no one would get back to me. I felt so proud of him and so happy that the help worked.

He accepted one of the internship positions and is there now.

[Lesson 8: When you take someone's advice you make the other person feel that they're making a difference. It's one of the greatest gifts you can give. And your mentors deserve it, because they are giving you one of the other greatest gifts - their time.]


I want to say a huge thank you to Will for inviting me into his office and giving me a tour. As a super-Disney fan, it was such an honor.

I hope you enjoyed his advice as much as I did, and I hope you take action on some of the gems in this story. 

Who has a job that you admire whom you could reach out to and ask for advice right now? 

What creative way can you get the attention of someone at a company you really want to work for?

Go for it!

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