If you start your career at a corporate bank, the path to success is usually presented as a clear progression of incremental promotions, straightforward skill requirements, and predictable time lines.

For those of us hell-bent on pursuing a creative career, there is no luxury of a well-trodden path.

Achieving big league success in a creative field can seem like an elusive confluence of meeting the right people, pushing your work into the right hands, and stumbling into the right room at just the right time. It’s grueling, inexact, and more than a little dependent on luck. 

While there’s never going to be a simple, tried-and-true road map to creative success, there is value in speaking to people who have forged their own path in a creative industry, and learning from their experiences. 

To start demystifying the path to creative success, we turned to Vanessa Holden, the newly-appointed executive design director of Sub Rosa, a strategy and design practice based in Manhattan.

If anyone’s “made it” in a creative field, it’s Holden. Her expansive career includes creative leadership roles at some the world’s most highly-regarded lifestyle publications and brands, including West Elm, Williams-Sonoma, Martha Stewart Living and Weddings, Vogue Living, Real Simple, and Marie Claire.

In her new role at Sub Rosa, she’ll be leading the agency’s design team, guiding the direction of multi-media projects for clients like Adobe, Comedy Central, and GE. 

Below, Holden discusses her unique path from freelancer to agency leader, how she evaluates creative risk, and the absolute best career advice she’s ever received. 

Vanessa Holden Talks Creative Success

What advice would you give to someone at the beginning of their creative career?

Holden: I started out freelancing because I wanted to try a lot of different things. I have always throughout my career toggled between full-time and freelance or consulting roles. I think there’s no better way to start your career than to freelance and ask questions. Be a person who’s really looking to learn, and you’ll gain a lot over just a few short projects or only a handful of clients.

One thing I would caution people about is that although the fluidity of freelancing is really appealing and there’s plenty of that work, committing to a full-time position and building something over a two or three-year period offers its own unique opportunities for growth.

Don’t take on freelance projects passively. Do it actively. Then, when you really want to learn more about yourself, commit to something for a longer chunk of time. Because there is a big difference between designing things or producing things on a project by project basis, and building a career. Creative people build careers over decades and every project you take on should be actively shaping your career in some way.

Do you still use any of the connections you built as a freelancer today?

Holden: Absolutely. No question. There are people that I call on now 25 years later who I can work with as easily today as the day that we first worked together. My network at this point is truly global.

Certainly the other thing about freelancing is that you get a marketing mindset, because you’re always reconfiguring your narrative. Who are you as a designer? How are you positioning yourself and your network and your contacts? There’s tremendous cumulative value to maintaining those relationships over time, not least because they’re super energizing and it’s exciting, and it’s fun being creative and working with people for 20 plus years and growing together.

Wherever you end up — for me starting in Sydney and having friends now literally everywhere across the world, or even just knowing a bunch of people in agencies or different kinds of creative roles across the city — there’s nothing more valuable than building your network. I’m actually right in the thick of having these conversations with my daughter. It all happens right there in the beginning. It does.

How do you decide it’s time to take on a new career challenge?

Holden: I moved to America to work in publishing. I had always worked in publishing and always imagined that would be my entire career. I was a print brand girl, always multichannel, but print was really at the center of any brand I was developing or working on.

In 2008, there was a radical acceleration in digital. The explosion of mobile apps created this really intense, almost immediate shift within the industry, and made me really reconsider what my skill set was and how it was applicable to things beyond print.

I was at a point where I could have gone in lots of different directions. I was then at Martha Stewart Living. I had a fantastic opportunity over three years there to flex into the multichannel space as digital was evolving.

By the time I started having a conversation with West Elm and thinking about what my next growth opportunity might be, I was keenly aware that publishing was just one facet of a more rounded toolkit I had. It became more about brand building — regardless of the actual output.

When I started that conversation with West Elm it became a story about being a proficient visual storyteller, which is really what I had been throughout my entire career. I started out as a graphic designer and an art director. Visual storytelling had always been central to what it was that I was doing anyway, and then the question was, “Oh, but am I ready for retail?”

Moving into editorializing a brand felt really like new territory. To me it was a very natural kind of extension of what I was doing in my day-to-day anyway, and for me was the best kind of risk because I had the toolkit that I needed to apply to it. I just needed to learn about a completely new context.

I think it’s risky to stay still. I think it’s risky to stay with what you know — which isn’t to say you should constantly be moving. With the freelance economy right now, it is possible to move too much, where you don’t learn enough about yourself and your skills because there’s so much movement.

But I do think it’s risky for anybody to say, “Oh, this is what I do, and I’m going to keep doing it for the next 10 years.” That’s just, I think, completely unrealistic.

When I think about risk or stability and what that ideal balance is, I think I have a pretty fluid approach to growing a career. I’m just always looking to expand my toolkit.

How do you decide which projects to pursue, and which to pass on?

Holden: I think I’m actually leaning how to do that now. I think I’m a person who says yes to everything. I also have a family, and that’s definitely always been the thing that comes first for me.

When I look at which ideas to scrap or which to move forward with, it’s like what’s my maximum capacity and what can I fit in there? I am learning to be more selective about my time, I guess, right now.

Seeking out spare time that’s truly just down time is also really important. I like to be really busy, but you need open time. How do you not just chase the ideas, but also prioritize unstructured growth time? It’s everybody’s challenge right now. I wouldn’t say that I had that figured out. I don’t know that I’m ever going to have that figured out!

What’s the best career advice you’ve ever received?

Holden: My three-part thing is: Get in front of it, ask for what you need, and own it.

Jim [Brett] at West Elm told me, “Imagine what it is that you want. Do a vision exercise for yourself, whether or not that’s a facet of a job or a bigger vision for where you want to be over time. What are you looking for? Get in front of it.”

Ask for what you need is the second part. People don’t know how to help you until you can ask them for something, until you actually verbalize that. I think people don’t ask for help with as much frequency as they probably should. Then once you have those two things — you have your vision and you have what you need — own your responsibility in delivering on that.

That to me creates extraordinarily rich creative space, because you have everything you need to execute what your vision — whether it’s for yourself or for a client on a project.

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