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Demystifying Creative Success: How to Build a Creative Career from Scratch

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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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Age Is Just a Number: How to Be a Leader at Any Stage of Your Career


I have a confession to make: I used to be embarrassed by my age.

And I don’t mean I was a little bit embarrassed. I’m talking a gut-wrenching level of embarrassment to the point where I would either lie about my age or deny the person a response.

After years of doing everything possible to avoid those four little words, I have managed to overcome my embarrassment — partly because I’m a little older, but mainly because I’ve come to terms with what I have accomplished and the hard work it took to get there.

History is laden with young leaders — trailblazers who envisioned goals that those above them seemed unable to see — and I believe there are more now than ever before. The pace of business is accelerating and I believe it is due to the unbridled energy and enthusiasm of young people who aren’t afraid to say, “I can do this, and I can do it really well.”

Take Mark Zuckerberg, Marissa Mayer, and Amy Schumer for instance. They’re all incredibly intelligent and successful young people who took advantage of a unique opportunity that seemingly no one else could see. They were also dedicated, methodical, strategic, and they understood what it would take to succeed.

I wouldn’t want anyone to suffer the embarrassment and insecurities I’ve felt by being young, hungry, and capable. As a young leader in the making, it’s important you know how to free yourself of this curiously common case of professional ageism. Below are my tips for doing just that.

1) Understand the business.

The most important thing that’s happening in your workplace is the overall health and prosperity of the business. It is vital that you not only work hard in your position, but also that you understand how your role fits in with the rest of the business to drive real results. 

And don’t ever be afraid to demonstrate this intelligence. For instance, if you happen to step into the elevator with the CFO, ask a question that represents your awareness of what matters to them, instead of a casual “So, how’s business?”

2) Be an active listener.

Even if you are a young leader in the making, you are still very much a student of leadership. Listen, ask questions, and soak up as much as possible. Your more experienced colleagues may or may not be leaders, but they’ve no doubt seen many more things than you have. Their insight could be invaluable — even if you don’t agree with their point of view.

3) Demonstrate your abilities

You don’t need a promotion to grow at work. If you think you can lead, then all you need to do is prove it.

This means asking for opportunity to shine, and demonstrating that you can step up when duty calls. It might only be a small task, but others will take notice.

4) Challenge the status quo.

Even the most traditional company should be open to new ideas (and if yours is not, maybe a new job is what you need). Even if the answer is ‘no,’ the fact that you aren’t afraid to reimagine ways of doing things will get you noticed.

It’ll be easiest to do this when you first start a job. When I worked at Microsoft, my mentor told me that you only have about six months to question everything before the position starts to change your lens — so don’t be apprehensive about challenging old ideas.

5) Know what you know (and what you don’t).

I worked really hard during school and was really pleased with where my scores landed, but I would never claim to be an expert in all of my subjects. In that same light, there are frequently aspects of your job that sit outside of your specialty. You should be confident in your expertise, but never be embarrassed by what you don’t know — it’s the only way you’ll ever give yourself an opportunity to learn more.

6) Share your unique thoughts.

No one looks at things quite like you do, and your insight could be invaluable at the appropriate time. Your opinions might not shake the earth every time, but there’s no harming in sharing what you think with others. In fact, it takes guts to share your opinions — especially if they are potentially controversial. So while you may not be a thought leader just yet, you can test the waters by writing blog posts, engaging in Twitter conversations, planning coffee catch-ups, and taking advantages of chance elevator encounters. 

7) Take and give feedback without getting defensive.

Many young leaders get defensive far too quickly, and they guard their ideas like they’re children. Push that zeal aside for a moment and take on feedback in any form — good or bad. You should also become able to share feedback with others as they’ll respect your honesty, even if they don’t show it the first time. The more feedback you receive and the more you give, the better you’ll become at yielding positive outcomes. Everyone will improve around you … which is what leadership is all about.

8) Take well-assessed risks.

Being young and bold can have its clear advantages. With less to lose, taking strategic risks will be key to your success. Zuckerberg, Mayer, and Schumer took risks, but they were meticulous in their execution and confident in their abilities. They were lucky in some ways, but they were also prepared and sure of themselves.

9) Remember, not everyone is like you.

If you’re reading this post, you’re likely someone who is interested in growing themselves. Keep in mind that not everyone is interested in moving into a leadership role. Some people prefer being individual contributors who excel in niche opportunities while others maybe just aren’t cut out for leadership in the first place. And that’s okay.

In the past, my inexperience has occasionally lead me to judge my peers harshly because they didn’t have what I call ‘B-HAGs’ (Big, Hairy, Audacious Goals). I’ve learnt that to be a great leader, you need to be aware of everything that’s going on around you — and that includes understanding and accepting how your colleagues differ from you.

I believe my story represents the aspirations of many young professionals who share an eagerness — a compulsion — to further themselves both personally and professionally. I just want to make one thing clear to other young leaders who are working hard to improve themselves: Always be proud of who you are and what you have accomplished because that’s the driving impetus of your future success. twitter-logo.png

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20 Mantras Great Leaders Live By Every Day


This post originally appeared on the Sales section of Inbound Hub. To read more content like this, subscribe to Sales.

Leadership can be a difficult characteristic to understand. Which qualities make someone a good leader? Do those same qualities translate to all aspects of life, or can a person successfully lead a sports team but fail in the boardroom? Are people born leaders, or can anyone inspire others to follow them?

I won’t pretend to know the answers to these questions, and I doubt that many people do.

But when I think about what it takes to be an effective leader, I am invariably reminded of late summer conversations with my grandfather on the deck of his home on the island of Martha’s Vineyard. We talked about anything and everything together — from the current state of Red Sox Nation to the most effective technique for shucking the cherrystone clams we collected earlier that day. But, on occasion, the discussion would drift towards more business-oriented topics and I got a free lesson in leadership studies from one of the very best.

To provide a little background, Don Davis, my grandfather, left a distinguished career in corporate America in 1988 to pursue his “retirement” as a professor at MIT’s Leaders for Global Operations program. During his 22-year tenure at the school, he shared the lessons he learned from his time in business and inspired more than a few of today’s most influential leaders.

As I am sure any of his former students will tell you, it would be nearly impossible to boil down all of his lessons into a single blog post. Fortunately, those same students were kind enough to compile a Memory Book after he passed away in order to share some of his most important teachings, namely the 20 leadership mantras that were core to his curriculum.

Here are those 20 mantras, along with some insight from our Martha’s Vineyard discussions. (For a more personal explanation of how these mantras helped various students succeed in business, you can find the Memory Book in its entirety here.)

1) Leaders don’t choose their followers. Followers choose their leaders.

One cannot simply choose to lead a group of people. You may be a leader in title, but you’re not a legitimate leader if your followers do not believe in you and your vision.

2) Followers choose leaders they trust, respect, and feel comfortable with.

If you don’t have the trust and respect of your followers, how are you supposed to make the connection necessary to inspire them to achieve great things?

3) Be yourself. The number of leadership styles is limitless.

There is no scientific formula for what makes a good leader, only a belief in your own ability as well as the ability of your followers to be successful.

4) Leaders need a base of power and authority — but the more they use it, the less there is left.

Needless to say, effective leadership requires a certain amount of authority. Like most forms of capital, that power is finite. Use it sparingly and only when necessary.

5) The best leadership is based on persuasion.

Anyone can have a vision. Leaders have the ability to persuade others to believe in their vision.

6) Leaders set the ethical standards and tone of their organizations by their behavior.

As a leader, you set the example. Don’t do anything that you wouldn’t want printed on the cover of the New York Times. Your followers are avid readers.

7) Integrity is the bedrock of effective leadership. Only you can lose your integrity.

Unethical behavior is a slippery slope. Avoid the slope at all costs because everyone slips.

8) “Selfship” is the enemy of leadership.

A true leader cares more about the success of his/her followers than their own success.

9) Be quick to praise, but slow to admonish. Praise in public, but admonish in private.

If you’re going to praise someone, do it big. If you’re going to reprimand, make sure it is warranted and do so in a respectful manner.

10) One of a leader’s key responsibilities is stamping out self-serving politics when they emerge.

As a leader, your job is to inspire the entire group. No single person is bigger than the group, not even the leader.

11) Be sure to know as much as possible about the people you are leading.

How can you inspire someone if you don’t know what motivates them?

12) One manages things, but people lead people.

It may be a bit cliché, but at the end of the day, followers are human beings. Don’t lose sight of that reality.

13) Diversity in an organization is not only legally required and socially desired — it’s also effective.

Every problem, obstacle, or issue has a different solution. Different perspectives make it much easier to identify the right solution.

14) Leadership should be viewed as stewardship.

Leader and teacher are synonyms, even if the Thesaurus tool in Microsoft Word doesn’t agree.

15) Don’t make tough decisions until you need to. Most will solve themselves with time.

Procrastination isn’t always a negative tendency. Don’t jump to conclusions. Sometimes you just have to give the problem time to work itself out.

16) When making decisions about people, listen to your gut.

Believe in your ability to identify the right talent. It’s your vision, so you should be able to recognize when a person embodies that vision.

17) People can see through manipulation and game-playing. Everyone can spot a phony.

This goes back to the mutual respect and trust that must exist between a leader and follower. Don’t undermine that mutual respect via manipulation. You’ll lose followers.

18) Learn to say, out loud, “I was wrong” and “I don’t know.”

You may be a leader, but you’re not omniscient. Don’t pretend to be.

19) If you know a plan or decision is wrong, don’t implement it. Instead, keep talking.

Don’t try to jam a square peg in a circular hole. Work with your team to figure out a way to round the edges of the peg so it fits properly.

20) Each of us has potential to lead, follow or be an individual contributor.

Potential is limitless and everyone has the ability to contribute to the success of a particular vision. It all depends on how strongly they believe in that vision.

There is no recipe for what makes a good leader, but these mantras can provide valuable guidelines. I wouldn’t trade those talks on the deck for anything.

Do any of these mantras ring true in your experience? If not, how would you tweak them?

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