Everything important I’ve learned in my career so far

I’ve had a lot of successes and challenges over the course of my career but all of those challenges taught me some important lessons. In this episode I share the most important lessons I’ve learned in 6 different areas in the hope that they will be able to help you have a more successful and creative career.

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Show Notes:


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. Creativity is a blue-collar profession – no getting around it.


– One of the most common career mistakes I see are creatives who think that by pouring all their efforts into learning design 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.


– As I put together this show I wanted to pass on tangible advice but if I am being honest I will admit that there is an element of luck in being successful. I define luck as 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.


– You absolutely need to have drive and ambition but you also need to have some patience to let opportunities develop and your career to grow.


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.


– 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 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’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. 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.


– 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.


– 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.


– 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.


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.


– 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.
– 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.
– 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.
– 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.
– 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.


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.


– 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.
– 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.


– Leadership takes courage you are going to ask people to do things they are not comfortable with, to do new things and all of that is going to make them uncomfortable.


– 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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