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Success is a choice (and everything else I’ve learned so far)

The 6 key elements in a successful creative career

As I’ve been searching for the next chapter in my career over the past few weeks I’ve found myself reflecting on the course my career has taken and thought a lot about what I did right and what I did wrong. It has been an amazing journey that has let me work on things I never dreamed would be possible, and I want to share some of the things that I’ve learned and been successful at in the hopes that they might help other people. I think that I’ve been building towards writing this article since I started this blog 12+ years ago as this piece weaves together a lot of the best articles I have written over that time into one cohesive narrative. My blog has been a critical part of my process in forcing me to constantly evolve as a designer, thinker, and leader since I was sharing the insights I’ve learned along the way it kept me from resting on past successes. I have broken the article down into the 6 areas that I think are critical for a successful creative career, and each of those then have specifics on how to do them well.

Over the years, the number one question I get from pretty much everyone is ‘Whats the secret to your success?”. My answer is short, sweet and always the same – “Have great ideas and work your ass off”. I then watch the hopeful, bright-eyed enthusiasm melt off their face as they realize that the secret they are seeking seems to be the two things they apparently want to avoid – time and hard work. The reality is that to be successful takes a lot of time, a lot of hard work and there is just no getting around it. You are going to have to evolve from a Designer or Copywriter to an Associate Creative Director to a Creative Director and on and on. Each of those stages will require you to learn new skills and continually evolve. Here are the two key insights I have learned that have helped me turn all that hard work in success.

One of the most common career mistakes I see are creatives who think that by pouring all their efforts into learning how to use applications will make them successful. Don’t misunderstand me, knowing applications are critical parts of any career but those applications are nothing more than an electronic pencil. Just like a pencil if you don’t have any ideas to draw, write or communicate then even the best tool is useless. You need to learn applications to the point where you no longer have to think about how to create your ideas and are just able to let your creativity flow. But it’s that focus on learning applications so they are tools to express your ideas that are critical because if you only focus on your ability to use the tools, then you will hit a ceiling as agencies and businesses value the ability to create ideas over the ability to just create executions.

It is true that college is not for everyone, although there will obviously be some careers that will require a long stint in college – you won’t be able to get any vet jobs without a long stint in college, as an example. Regardless of what you want to do in the world, if you have the capacity to further your studies then it is important that you go out and learn new skills. For example, if you are interested in becoming a counsellor or scientist of the mind then you would aim to look for the best psychology colleges in PA, CA, or, any other region so that could develop skills as well as improving your qualifications. Although this is a lot of hard work it will be worth it in the long run.

As I put together this article I wanted to pass on tangible advice but I will admit that there is also an element of luck in being successful. It happens when you get one of those rare and magical moments where everything you need lines up and the universe gives you an amazing opportunity. The problem is that most people are completely unprepared to act on those opportunities and they either don’t have the skills, knowledge or insight they need to take advantage of them. I have found that to be successful you have to be willing to work constantly and prepare for these future opportunities even when you don’t know when or if they are going to arrive. It is a hard thing to do because it requires a lot of discipline,self-motivation and belief that the work will pay off at some unknown point in the future. I have always tried to approach my career as it is a blue-collar profession working to evolve the skills I think are strong and working to learn and improve the skills I think are weak. For me, it has paid off because when those rare moments came around, I have been ready to take advantage of them which has made all the difference.

I’ve always focused on making the foundation of my career the ability to deliver great ideas over the ability to just hit a deadline, know a new technology or use an application. I think this has worked because those applications, technologies, design aesthetics and even the needs of society have changed but the need for great ideas will never change. Here are the three key insights I have learned that have helped those ideas get stronger and work better within a team.

In my article ‘Jiro dreams of sushi. You need to dream of design‘ I wrote about master sushi chef Jiro Ono who teaches his chefs that to be a great chef you need to have tasted great food so you can develop your palette to know when you cook great food. It’s a critical concept as a creative as well because to be successful you have to be in a constant two-part cycle of experiencing the best of your chosen creative profession and then using that knowledge as a measuring stick to judge your work. This means that to be a great designer you have to constantly experience great design or to be a great writer you have to constantly read great copy and then you use that taste level and insights to drive your work forward. You also have to understand that this cycle consumption to developing your palette never stops no matter how long you have been in the industry. It has to constantly evolve to keep up with changes in society, psychology, technology, creativity and design. I have seen many great creatives who think that they know it all or that they don’t need to keep up this constant evolution, and they are the ones who quickly find their work becoming increasingly less effective until their career fades away.

I have always coached my teams on the importance of being able to externalize and share your creative process with the rest of the team which is a concept that runs counter to what is often encouraged by a lot of companies where individual achievement and ownership is valued over the work of the team. I think it’s important to not only share your process and ideas with the team but to develop a culture where the team will constantly try to pressure test and find weak spots in those ideas to make them stronger. It’s something that requires strong leadership to work so that everyone doesn’t feel like that is being attacked or their ideas are being put down but instead allows everyone to contribute and take ownership in creating the best ideas. I have seen this concept work as the core of a lot of groups at companies like Apple and Google where they are relentless in seeking out the best ideas by sharing their work, knowing it can always be better and using that process to continue to refine it until it is something great.

Also in my article ‘Jiro dreams of sushi. You need to dream of design‘ is another theme where Jiro talks is his lifelong dedication to sushi and his constant work to improve all aspects of his craft. This is a trait that I’ve come to embrace over the course of my career and it’s a trait that I see shared by every great creative mind I’ve ever known. I think it’s a byproduct of the fact that they constantly work to develop their palette and they constantly want to make everything they do better. I’ve come to embrace the fact that there is no time when the design is completely out of my mind because I am constantly looking for new inspiration, tormented by the flaws in my old work and looking for that next great idea. When a project is finished I allow myself 15 minutes to enjoy the work that was done and then I am on to next project. I have little use for nostalgia because when I look back I see only see the mistakes and things that could have been done better. Nostalgia is for people who’s best days are behind them and for people who look to the past for answers. That eternal dissatisfaction can be a strong motivating force to keep your work moving forward but it is also something that needs to be kept in perspective because if it gets out of balance you can become a naysayer who lets that dissatisfaction take over their process and let it blind them to new ideas.

I have found my biggest career challenge has been getting a clear understanding of who I am as a designer, understanding my unique creative process and then learning to summon my creativity on demand. I took years to write my “design ethos” which define my guiding design and leadership principles I wanted my group and myself to always aspire to. They are meant to be simple statements but I wanted that simplicity to be deceiving as each is purposely challenging and aspirational. Coming to understand those things is an incredibly personal process so there is no book, conference or class that is going to be able to teach you more than some common themes and starting points you can build on. Here are the three key insights I have found as I have worked through the process of getting to know who I am and how I have great ideas.

The process of having a great idea is different for everyone because we all approach problems differently. I have found success by centering my creative process around divergent and convergent thinking. Divergent thinking happens when you can work quickly to create a lot of different ideas through writing, sketching or even done in Photoshop (but I don’t recommend it). You then keep building on your ideas, to push yourself into new thinking, to work through a lot of different ideas and to embrace the fact that not all of those ideas are going to be great. Those bad ideas can be just as valuable as the good ones because the failures may uncover new lines of thinking or highlight possible weaknesses in your concept. Once you have generated all those ideas it’s important to use convergent thinking to take them all and curate the best parts into fewer condensed ideas. You can then go through the process of divergent and convergent thinking, again and again, to focus, refine or strengthen your ideas into something great. I have found that the most highly creative people are the ones who really understand their creative process and are really good at getting their brains to flip quickly between divergent and convergent thinking so they can quickly generate strong ideas. But the most critical part of the entire process is that you take the time to be self-aware and understand the process you went through when you had a great idea and what you did when your ideas weren’t so great so you can replicate it or avoid it in the future.

Self-awareness plays a critical role in your success first for your ability to know how to have ideas and second as you become a leader so you can understand how your actions affect your team so you can tailor them to become more effective.

Every person has a completely different way they create ideas because creativity comes out of your personal life experiences, opinions, emotions, strengths, weaknesses and personal emotional baggage that you have accumulated over your lifetime. All of those variables come together to create your point of view and it drives what happens in your brain when you sit down with a blank piece of paper to start to work through a problem. As a creative director I think it is my job to work with my team to get them to start to become aware of all of those variables so they can start to pay attention to exactly what happens when they have a great idea but also what happens when they get to a place where the ideas just aren’t coming. It is this self-awareness that is the mental foundation of every great creative mind I have ever known. It gives you the ability to start to understand how to have ideas, to understand what do you need to do mentally to let those ideas happen and then start to work on how you can make it happen faster and with great regularity. I’ve found books like Making Ideas Happen, The Accidental Creative and Die Empty are great books that can help you with this process.

Self-awareness is also critical as your leadership role grows because I have seen lots of incredibly talented creatives who have great leadership potential who self-sabotage opportunities because of the way they express their views, treat other people, or even handle their ego completely undermine their authority. During an interview process, such personality traits can undermine your chances of selection. For someone who’s in the initial stages of an interview process, demonstrating your leading and onboarding plan that aligns with the vision of the company can impress your recruiters. To be an effective creative director, you must have the self-awareness to understand when you need to drive your vision for a project versus when you need to support and nurture the visions of the rest of the team. The best leaders I have known can keep these things in balance so they are seen by their team and clients as leaders with great ideas but they are also seen as someone who lets their team shine and grow. This process means that you need to develop the confidence and self-awareness to let those other voices be a larger part of the conversation because no one who is creative wants to work for a dictator who just wants you to do nothing more than execute on their ideas with no input from the team.

As you go through your career you will become more accomplished and gain more experience but you will notice a change taking place. Early in your career you will be inspired by other people and use them as a guidepost to push yourself forward but as you gain more experience you will find that the problems become harder, the solutions to ideas and leadership will be more personal and that you will be less motivated by the people that used to inspire you. To continue to evolve as a thinker, designer, writer and leader you have to develop the ability to inspire yourself, stay grounded, motivated and moving forward to be successful at all of those challenges. I inspire myself through talking to some of the world’s greatest chefs like Ferran Adria (Insights on creativity from Ferran Adria, the world’s greatest chef.) and Heston Blumenthal (Why you need to develop short-term memory loss) or doing experiments on my friends to better understand the psychology behind why people use social media (The Inverse Facebook Experiment). You have to stop looking to other for answers and understand that companies want people who can bring value and original thinking to their roles and not just copy what other people are doing. To be able to find real inspiration means that you will have to invest in understanding your creative process as I talked about before because if you don’t understand how to have great ideas, then you will never really understand how to feed your brain with new thinking to inspire new ones.

There are few lines that are more difficult to walk than knowing how, when and where to correctly promote yourself, your abilities and achievements. People who confidently make their achievements known are often seen as more competent, yet we also live in a culture of modesty so if you do it badly you can be seen as an egotistical loner who puts themselves ahead of the team. Here are the three key insights I have learned on how to walk that line, prepare for the future and build your brand.

I have found the biggest reason why people are unable to get their dream job is that they have no idea who they are and what makes them different from everyone else. Their resume and portfolio are filled with generic business-speak and overused cliché phrases that look impressive to fill up a page but ultimately say nothing about them. To solve this problem you have to be able to take a step back, treat yourself as a client and think about yourself as a brand by defining your core values, brand voice, image, differentiators, etc. You have to be able to do this not only for your resume or portfolio but so can you can stand out in an interview or even at your current job by having the ability to articulate and build on your unique strengths and differentiators. My article ‘How to write a resume that will get your noticed‘ goes into a lot more detail about different exercises you can use to define your personal brand to help you stand out from the crowd. This works takes a lot of personal introspection and treating yourself like one of your clients but it leads to a place where you will be able to understand how you are different, what your strengths are, how those lead to your achievements and why they make you a unique talent any company would want to work with.

Once you have defined your brand values then you need to invest in your image, content and messaging through things like your resume, portfolio, social media channels and networking because this is another case where opportunities both good and bad won’t call ahead. Many people are surprised to hear that I have been laid off from 2 of my last 3 jobs and it happened because of sudden changes in leadership or business strategy that I could do nothing about. If you just read that line and thought to yourself that you are good at your job so you are safe then you are nieve. I got laid off from my last job right after I designed an app that was featured in 3 Apple keynotes, 4 Apple TV commercials, and generated tens if not hundreds of millions in free press but that wasn’t enough for me to keep my job. If you are working on your portfolio then you need to read my article ‘A Creative Director’s 5 biggest portfolio warning signs‘ which lays out the five most common mistakes and warning signs I see in creatives portfolios and how to avoid them. I have also found that your professional network is an overlooked necessity because the best jobs will never be listed on LinkedIn since those candidates are found based on referrals, reputation, and notable work. The best way to build that network is to connect with people in real life but LinkedIn can also be an incredible tool. In the end, I have learned to never forget that my career carries on at the whim of businesses where loyalty and hard work can mean far less than they should so you never can never stop working to build your brand through your resume, portfolio, social media and network.

Building your personal brand is important to your success but you have to balance it with the fact that no great idea will ever be possible without the collaboration and support of a team. I have worked with too many creatives who think their brand is the only thing that matters and their ego is so out of control that they are only concerned about themselves and what they can put in their portfolio. Those people weaken the team, the ideas it creates and they never last for very long. To become a leader or even to become a great creative you need to understand how to work with people, how to inspire them, build up their skills and make every project better for your involvement. Your reputation and leadership skills will become more important than your portfolio as you go through your career because the more senior positions you take the more those skills will be what you will be judged on. If you are unwilling to invest in your leadership skills or control your ego to put others needs before your own then even the best portfolio won’t lead to a great career because you will just be a great designer no one respects, wants to work with or work for. My article ‘Creative is all about R-E-S-P-E-C-T‘ goes into more detail about the role of respect in creativity and why it is so important.

This business is filled with people who say they know how to lead creative teams but the reality is that most are merely managers that do nothing more than hand out deadlines and have no idea how to inspire a team or develop new leaders. Being able to lead a team of creative minds takes a completely different set of skills than those you will need to be a great designer, writer or thinker. Being a leader is about developing skills in psychology, empathy, and confidence that you can use to guide your teams. Just like your creative process, everyone’s leadership style is different and it takes self-reflection to understand how you can be the most effective. Here are the three key insights I have learned that have helped me evolve as a leader who can inspire teams to create great ideas and grow future leaders.

I have found people who are in charge of teams can be grouped into two general types – leaders and managers. Managers do just what the name implies by managing their projects and focusing on individual deliverables. They hold weekly status meetings where the team slowly and painfully goes around the room reporting in on the progress of the workload. This may be great for employees who do repetitive and mindless tasks but anyone creative it is a slow, uninspired death where you increasingly feel like your career is going nowhere. Then there are leaders who are people who are sources of creativity, inspiration, leadership and make everything they are a part of better. What are they doing differently and how did they evolve to from being a manager into being a leader? My article ‘Are you a Leader or Manager?’ takes a look at six comparisons between the traits of leaders and managers to illustrate their difference and help you understand how to gain more traits of a leader. It has been the most popular article I’ve ever written and has been the basis for some of my best-reviewed talks which only proves to me that there is a serious leadership vacuum on creative teams so companies need to take this problem much more seriously if they want to retain their best talent and grow their business.environments.

Throughout my career, I have consistently been given high praise for being really good at selling creative and it didn’t happen by accident. Early on I realized that my design skills were only going to take me so far if I wasn’t able to sell my work. The problem was that I left college terrified to talk in front of even a small group of people and hadn’t developed any tools I needed to sell my ideas. I needed to get over my fear, understand how to sell and the psychology behind all of it all. I started to hanging around with people who sell to high-end clients for a living like venture capitalists, sports agents, and PR agents to study their techniques. From there I’ve spent the past 15 years studying and learning the craft of presenting and selling so that I have been able to get innovative new ideas through the corporate red tape and have been able to give keynotes in front of thousands of people alongside presenters like Apple co-founder Steve Wozniak. It is a critical skill to be able to position your group for success with clients and getting your best work to see the light of day. I put everything I learned into a 3-part series of articles called ‘Presenting Creative 101‘ is one of the most popular articles I have ever written and captured everything I have learned in my career about how to sell you ideas.

As I said before, to become a creative director or a leader means developing a whole new set of skills beyond the ones of just being someone who can create ideas. For me, that has been a 20+ year journey riddled with ups, downs, insights and hard realizations that were all necessary to help me get to where I wanted to go. One of the biggest realizations that came to me out of that process is that not everyone loves a leader. It is a hard thing to accept because so much of what we read and see leads us to believe that if you stand up, try to do something new and try to lead a team that we will be celebrated for your effort. It’s not all gloom and doom by any means as there are times when you will find that happy ending for stepping up into a leadership role but it isn’t always the case for some reasons. I don’t see people talking about this problem or coaching their teams on it and as a result, a lot of great potential leaders get discouraged and shrink back to smaller roles because it wasn’t what they thought it was going to be. My article ‘Not everyone loves a leader‘ talks about some of the challenges I have found and some of the ways I have been able to overcome them trying to take a strong leadership position at both agencies and client-side companies. If you’re dreaming big and hope to be in charge of your own company then you should try to ensure you are respecting your employees and this should ensure that they end up resultantly ‘loving the leader’. A happy workspace is a successful workspace. Looking at this PTO guide may guide you on what benefits you can give your employees in order for them to stay happy and continue to want to work hard for your business.


I firmly believe that being successful is a choice and all of this comes down to one simple question – are willing to put in the seemingly endless time, studying, researching, working and self-reflection needed to become successful? And not just do it for a week or a month or even a year but do it over the course of your entire career. I have worked with TONS of incredibly creative people who have amazing talents, who have brilliant ideas, talk about their huge aspirations and end up with careers that show great promise but ultimately find little success because they aren’t willing to do ALL the things you need to do to be successful. You have to make your future happen by choosing to work hard, knowing who you are, knowing when to take a risk, being eternally dissatisfied and even a little crazy. Because as someone smarter than me once said the people who are crazy enough to think they can change the world (or themselves) are the ones who do.

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