Obsessed: Building a Brand People Love from Day One

Welcome to 99U’s monthly Book Club, where we look at book releases that challenge us to think deeper, explore new perspectives, and spark a better understanding of the nuances of a creative career, from leadership and community building to productivity and everything in between.

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Red Antler, the Brooklyn-based agency founded in 2007, is behind some of the most memorable campaigns of recent years and is responsible for the branding of some now-household names. Casper, Allbirds, Snowe, Hinge—the company has a knack for developing the stories of start-ups and new ventures, with a fine-tuned radar for what draws us to a brand. 

Co-founder Emily Heyward works with brands from their inception, during those heady first days of launching a product, so she has deep insight into what makes some brands stick. With an eye to the psychology behind consumer decisions, and a keen knowledge of cultural shifts that shape our choices, Heyward’s book Obsessed: Building a Brand People Love from Day One, is a blueprint for anyone thinking about branding and how to create a sustainable connection around a product or service. 

We drew out some key lessons from Heyward’s book, and what her branding strategies can illuminate about integrity, community, and storytelling. 

Start before step one

Red Antler starts working with their clients long before the product launch date. As Heyward says, “Half of our clients are ‘pre-launch,’ which means that we meet founding teams before they’ve launched their businesses, and help them to create the entire consumer-facing experience through the lens of brand.” 

It’s here that the work of brand building begins, and where the big questions need to be addressed and answered. With any venture, whether it’s launching your own studio or embarking on a freelance career, it is crucial to examine your intentions and take a step back to look at the big picture view. Long-term success is impossible without a deep understanding of your purpose and answers to the inevitable questions of who you are and what you stand for. 

“With any venture, whether it’s launching your own studio or embarking on a freelance career, it is crucial to examine your intentions and take a step back to look at the big picture view.”

Heyward says, “Founders need to be thinking about brand from before day one; it needs to be embedded in their culture from the very start.” By weaving it into the DNA of everything you do, your brand will always reflect a fundamental purpose, and help act as a North Star with any tough decisions. Think of branding as woven into your entire being, not a surface-level afterthought. “Leading brands are able to form deep emotional connections because they stand for something that people care about. When I talk about brand, what I’m actually talking about is what a business stands for, at its very core.”

Follow the “Why?” questions 

Obsession arises from the personal connection that consumers when brands speak to them on a deeper level—or when they encourage alignment of their lives and the product. Asking “Why should people care?” prompts a host of philosophical questions, and in Heyward’s experience, many of these eventually circle back to the big one—fear of death. This isn’t necessarily the grim concept that it sounds like! “To successfully launch something new and have people fall in love with it, you need to tap into a need that’s deep and true, and that has existed for a long time before you came on the scene, perhaps as primal as fear of death itself.”

At its core, it is about digging into what is behind all of our decisions, and following the trail of “Why?” questions to come to a common ground. Once you think you’ve reached the deepest level of understanding someone’s needs, go a step further. Does it connect to a universal, primal notion that we all share? That’s where you’ll find the answer to the real problem you’re trying to solve. 

Create community at every stage

Connecting the product to the personal story arc behind it is the strongest bond you need to create. The emotional idea needs to be backed up by practical function. If these don’t line up, your project will always be shrouded in inauthenticity. Start by forging connections between people, which will, in turn, create deep bonds to the brand. Even if you don’t have a brand that naturally lends itself to creating a robust community (Heyward cites Spotify’s playlist ads as a hugely successful illustration of the strong community the brand created), examine where there is potential to nurture community, create a shared vocabulary, and a sense of kinship among those who are users of the product. Heyward notes, “Brands build successful communities when they create a powerful feeling of inclusion. This does not require purposely leaving people out, but it does require a willingness to put a stake in the ground about who you’re for and what you stand for.”

“Brands build successful communities when they create a powerful feeling of inclusion.”

Part of inspiring genuine passion for your product means recognizing that you must make some savvy decisions—about who you’re brand is for and who is not part of your target demographic. Attempting to be all things to all people is a telltale sign of insecurity and lack of understanding of your purpose. Nobody wants to be talked down to, but at the same time, you don’t want to shut an audience out with impenetrable terminology or arcane references. Walking that fine line creates a community of insiders, with a shared passion, and as Heyward notes, “Passion is powerful within an individual, and unstoppable when it’s shared. When a brand creates a movement, it’s because of shared passion.”

The power of the personal 

Today, it might feel as though the world is saturated with new brands, spin-offs, and product launches. It can be easy to feel overwhelmed, cynical, or even wish to opt out altogether. Even for dedicated minimalists, though, consumer decisions come into play every day. So how does a brand appeal to those who are wary of the whole prospect, and what makes the brand-consumer relationship go beyond a merely transactional one? Heyward makes note of the glut of similar ideas that are cropping up in the marketplace, and how branding is ultimately what sets them apart from the rest. “Now, within a month, we’ll sometimes meet with three different teams launching nearly identical ideas. Because it’s so much easier to get things off the ground, and because technology has lowered the barriers to entry for everyone, the difference in success largely boils down to brand.” 

“What makes the brand-consumer relationship go beyond a merely transactional one?”

The success of a brand rests on making it personal and bringing customers into your world. Those who understand how to align their values with their venture are much better placed to succeed. Think about why you have embarked on starting a brand, project, or collaboration. What is driving you to work on it every day and to dedicate your time and energy? Where does your inspiration and motivation come from? Heyward mentions engaging with several clients whose personal stories behind their decision to start a brand set the tone for their story arc and subsequent messaging. This idea of personal alignment can always be traced to the founding team and staff. “Even if you don’t exactly mirror your target audience, you need to embody the values and spirit of the brand you seek to create.”

Start a conversation  

We know that the days of relying on television commercials and newspaper ads are long gone. To succeed in the now, a brand must be nimble and ready to adapt to ever-shifting arenas. Heyward is all too aware of how a brand needs to navigate this changed landscape, “With all the places a brand needs to appear today, you have to bend and flex to keep things interesting.” What’s more, the idea of a static, perfectly polished brand no longer rings true for most of us. We know all too well what goes on behind the scenes, and perhaps even have a healthy skepticism for advertising and targeted marketing. 

Honesty, transparency, and humility are the cornerstones of creating a foundation of trust and making the consumer part of the story. So how do you draw someone in and make them stick around? In Heyward’s experience, the key is to start a conversation. Sparking dialogue between the customer and brand is a way to invite them on the journey, with all the pitfalls and successes. This might mean relinquishing control, which is understandably a daunting risk with any new venture. But that can pay off with remarkable results. “Letting go of control is what allows consumers to become part of the story. Their content gets featured, they see themselves in the brand’s narratives, and they feel more invested. Instead of a top-down approach, it’s a conversation, and conversations are by their very nature unpredictable—at least the good ones are.”

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Stumbling Blocks and Obstacles: How to Overcome Creative Ruts

How do you overcome creative block? It’s a simple question, but one that we wrestle with as creatives over and over again. Just when we think we’ve found the answer to move past a current rut, a new challenge arises. Feeling stuck happens to all of us—newly minted graduates, creatives early in their practice, mid-career practitioners, and seasoned pros. 

Although I help creative professionals get unstuck frequently through my work as a career coach, I decided to turn to the internet for help answering this question: How do you overcome creative block? More specifically, I asked my Instagram followers, who generously shared practical tips, what helps them move forward, how to preemptively tackle getting stuck, and questions for further exploration when creative block strikes.

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Preemptively write out your creative tasks. 

Benjamin Welch (@benjaminwelch) shared a new approach he’s been trying, which he’s found helpful so far. “I write out my creative tasks, but do this the night before rather than the day of or right before I start. Then my only decision required is to check the list and start doing something on it. This way I’m not relying on my mood or inspiration to give me ideas and I don’t have to feel pressure to come up with something on the spot.” Instead, he looks at his list, picks something, and starts.

The idea that you shouldn’t wait for inspiration to arrive was echoed by Kara Gordon (@kayessgordon), who said, “I try to remember to not wait for inspiration to strike to make art. Not every mark or work needs to be precious. It’s about the process.”

Shake up your routine.

Multiple people embrace the philosophy that changing things up, literally, can be effective by giving you a break and allowing you to still engage your creativity, but perhaps in another way. Kara Gordon shared that letting go of her routine can also help her move forward, whether that means taking a different route to work, going to a museum, or meeting a friend she hasn’t seen in a while. “Seeing and experiencing something new can allow you to shake up the patterns in your brain.”

Michaela Fiasova (@michaelafiosova) often works on more than one project at a time so she can switch in between them, and when she’s at a standstill, she’ll sometimes watch YouTube videos about something completely unrelated to her project. Indhira Rojas (@redindhi) also takes this approach, switching to a completely different task or activity to clear the mind, even if it’s recreational, “in the hopes that a new insight arises that sparks a new wave of creativity.” For Danielle Evans (@marmaladebleue), the ultimate goal is having some kind of output to build momentum: “I swap disciplines. Sometimes output is output and that’s all that matters.” 

Reconnect with your physical self. 

One of the most suggested tactics for overcoming creative block was to do something physical, whether it’s as simple as a brisk walk outside as suggested by Nicole Jacek (@nicolejacek), or as involved as taking a long swim as Anne Ditmeyer Stark (@pretavoyager) does, “The swimming pool is one of the places where my best ideas come. They flow. It feels counterproductive to getting work done, but the key is unplugging from my computer and screens.” 

Karoleen Decastro (@karoleend) likes to take her physical activity a step further and said that, “Mindful walks work wonders.” She might challenge herself to count ten blue things, nine red things, eight green things, and so on, until she feels grounded and open to her inner world. [Ed. Note: This approach sounds familiar.]

Regardless of how you get out of your head and into your body, making a physical change can help shift your perspective as Lys Hunter (@lyshunter) noted, “Sometimes you have to leave—leave the office, leave your house. Take a walk and try to think about a big world problem. Get out of your small problem.”

Stop resenting the ruts.

Wix VP of Design Hagit Kaufman (@hagitkaufman) has chosen to change her perspective on being in a rut. Instead, she sees it as an opportunity, “I used to hate it. These days I resent it less, because I now know that it always brings me to something or somewhere new.  A new idea, a new way of thinking or something simpler, like putting two old things together in a new way.”  

Payal Vaidya (@payalcv) also sees creative block as an opportunity rather than resenting it. She asks how she can look at it from a different perspective, or even try on different personas who might solve the problem from a new angle, “How might Paula Scher approach this or what would Debbie Millman ask?”

Commit to working through the block. 

While the instinct might be to take a break and do something else, some individuals said they can find it helpful to stay put and work through their block. Kate Aldridge (@k8.aldridge) dives into the part of the project that she enjoys least, or that is the least creative, so it becomes more about production versus pressure to connect with her creativity. “I do the part I enjoy least, like editing, so that I can still have my hands on it to craft it without the pressure of wanting to be creative.” 

For Kriz Bell (@krizbell), it’s about getting the not-so-exciting first draft of a project out of the way. “I start digging in and get the stick-flavored draft out of the way. And if I’m really blank I’ll go basic and dig into who, what, where, when, how. If you keep going, you’ll end up somewhere else.” 

Identify the source of your block.

Sometimes when we experience creative block, it truly is about the project. As Karoleen Decastro noted, it can sometimes stem from fear or boredom about the work. If she can identify the source, she can be more specific about how to address it. Devin Kate Pope’s (@devinkatepope) advice builds on this approach and asks us to consider that what’s stumping us might not be about the work at all. She suggested using the HALT Method. “Am I Hungry, Angry, Lonely, Tired?” If yes, address it and then make another attempt to progress. 

Ultimately, we will have many opportunities to come face to face with creative block over the course of our careers. Expecting it to be par for the course will help us accept that there’s nothing inherently wrong with us—we’re not broken or insufficient. We’re simply having a normal experience. Adjusting our expectations can be key as Indhira Rojas pointed out, especially when our creative block doesn’t dissipate overnight, “If the creative block is a long one, I let go of expectations for the project, give myself a break, relax, and try to gain perspective.” 

Want more on overcoming creative block? Read “How to Overcome Creative Obstacles” by Mia Pinjuh.

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How to Think Smart About Your Downtime

We all know constant connection makes it harder than ever to switch off when we finish work for the day. It’s vital to set aside time to properly recharge. But let’s say you already heeded that advice—does it matter what you actually do in your downtime? Moreover, is there a way you can use your hobbies to not only have fun and unwind, but also to boost confidence in your work life?

Related findings crop up repeatedly in research literature. For instance, sports-based hobbies are particularly beneficial for recharging. Fred Zijlstra, a professor of work psychology at Maastricht University, says this is because they are fun and require you to concentrate on what you’re doing. “Physical activities work well, in particular when people have a rather desk-bound job, because they require active engagement and they distract the mind from work-related issues.”

However, psychology has also thrown up some contradictory research, especially in terms of whether you should pick hobbies that resemble your work or are completely different. Here’s our look at how to evaluate for yourself based on your current priorities—even if your only requirement is to avoid Zoom outside of work hours.

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Balance out your working life 

One approach is based around achieving balance and recovery. This suggests you use your downtime to do something completely different from your job. That way you’ll feel happier and more refreshed, which will have trickle down benefits in your workday. 

Dr. Jessica de Bloom, who splits her time between Tampere University in Finland and University of Groningen in the Netherlands, says to think about this is in terms of the satisfaction of your various “psychological needs,” specifically detachment, relaxation, autonomy, mastery, meaning, and affiliation. 

“It might be helpful to first understand which of your needs are least satisfied [by work] and choose hobbies which support these needs,” she says. “For instance, if you have a work situation which offers very little possibilities for social interaction and fulfillment of the need for affiliation, it might be beneficial to choose a social hobby. If I have a job which is not very challenging, I may want to choose a hobby where I can learn new skills and experience mastery and competence.”

Nurture work skills in your downtime

Yet there’s another perspective from work psychology called Enrichment Theory, pointing out that the skills and experiences we build up in our free time can flow through and complement our work performance, which suggests you’re better off looking for a hobby that resembles your job in some way. If you were looking to harness your leadership skills, for example, then facilitating a book group or playing the role of team captain for your local weekend soccer team could be the perfect training ground. 

“Enrichment Theory is about the positive interactions between different roles, it outlines different resources you might generate within one role—material resources, psychological resources, social contacts—and you apply them in another and it boosts your performance in that other domain,” explains Dr. Ciara Kelly, a psychologist at Sheffield University Management School in the UK.

Reflect on whether a hobby is a passion or just a bit of fun

Dr. Kelly led a recent study (free to read online) that aimed to reconcile the two apparently contradictory perspectives emerging from work psychology: one based on balance and recovery, the other on enrichment. In effect, both perspectives are correct, depending on the attitude you have to a particular hobby. 

Kelly and her colleagues surveyed over a hundred volunteers repeatedly over a seven-month period, asking them whether they’d spent more time than usual on their hobby and how confident they were feeling in their ability to perform well at work. Crucially, they also asked the volunteers to rate how seriously they took their hobby and how similar it was to their work.

The results paint a more nuanced picture of how we should think about our leisure time. It’s not that some hobbies are better than others, nor that you should always aim for hobbies that are either similar or different from your job. Rather, it all depends on the kind of attitude and approach you have toward a particular hobby—specifically whether you take it seriously or not. 

“A serious approach would be one where you strongly identify with the particular activity, where you could describe yourself as ‘a climber’ rather than climbing just being something that you do,” explains Kelly. “It could be something where you’re quite invested, you intend to get better at it, and intend to keep doing it into the future.” 

Beware burnout from serious hobbies that are similar to work

For serious hobbies that were also similar to a person’s job, Kelly’s team found that spending too much time on them actually dented confidence at work. “If you get the situation where you’re highly committed to the hobby and it’s just like work, and you’re invested in both sides [play and work], and you spend more time on it, then you get a bit of an adverse impact,” says Kelly. 

In a sense, if you’re driving yourself hard at work and in your hobby and they’re both pretty similar, you’re effectively spreading yourself too thin. However, this wasn’t an issue for the research volunteers who took a casual approach to a hobby that was similar to their job—they benefited from the overlap, like the manager who gains leadership skills from time as captain on the soccer pitch. 

Of course, this raises the question of what counts as “similar.” For the research, hobbies were categorized as similar based on the volunteers’ own perceptions. For instance, one of the volunteers was a school teacher who felt that playing the Dungeons and Dragons game was similar to work, perhaps because of the need to improvise and be creative in both roles. Likewise, you’re probably the best judge of whether there’s an overlap in your hobby and work. 

If you sense that there is a degree of similarity and you’re highly committed to the hobby, Kelly’s advice is not to give it up. “That would be really depressing!” she says. Rather, it pays to be more mindful of the rhythms of your work and hobby, to avoid potential clashes when either are going through a particularly demanding phase. And take care not to overload yourself on screen time if your extracurriculars have gone virtual.

Dedication to hobbies that are sufficiently different can pay dividends

It’s worth noting that taking a hobby seriously wasn’t a problem if it was sufficiently different from work, likely because the contrast prevented too much conflict or exhaustion from competing demands. In fact, spending more time on a serious hobby that’s totally different from work was also beneficial, leading to feelings of greater professional confidence. 

That makes sense because whenever we invest in any activity over the longer term, we learn empowering lessons about how dedication leads to gains and improvement, which is bound to spill over and increase self-confidence at work.

I can relate to that myself. I’ve spent the last seven years or so playing in a local table-tennis league, climbing from my club’s E team to the B team and advancing through the league divisions. I’ve experienced first-hand that you get out what you put in, which has translated into greater motivation and confidence to improve in my career. At the same time, of course, the game itself couldn’t be more different from my day job as a writer, so there’s no risk of a clash of demands.

 

To recap, the new research found that taking a hobby seriously was beneficial—if it was sufficiently different from work; at the same time, a hobby similar to work was beneficial if it was just a casual past-time. In other words, they’re probably aren’t good and bad hobbies, it’s more about being smart in your approach.

It’s important not to overthink these things, though. Jessica de Bloom says it can become a real problem if we start feeling the need to be perfect employees in our free time as well as at the office—don’t put pressure on yourself to excel at sports and to be a perfect parent. To return to Professor Zijlstra’s message, remember the best way to recharge (which will benefit you at work) is to use your leisure time to do something you enjoy and that’s sufficiently engaging. Anything from collaging to playing tennis with friends could fit the bill—just find what works for you. 

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Pay Attention: The Art of Noticing

Welcome to 99U’s monthly Book Club, where we look at book releases that challenge us to think deeper, explore new perspectives, and spark a better understanding of the nuances of a creative career from leadership and community building to productivity and everything in between.

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Have you ever been on a Zoom call where someone drinks from a mug? Me too. But it took me a long time to notice something: the underside of mugs is completely underutilized real estate. Talk about a missed opportunity! I also happened to be reading Rob Walker’s book, The Art of Noticing: 131 Ways to Spark Creativity, Find Inspiration, and Discover Joy in the Everyday when I made this observation. It made me ponder what else is staring me in the face that I’ve never noticed before.

Walker, a journalist covering design, technology, business, and the arts, challenges us to see the world around us with fresh eyes through his collection of challenges, prompts, and exercises proving you don’t have to go far to be a powerful observer. Walker culls examples from literature, research, and other writings to make a further case for his suggestions. Here we explore some of our favorites from the book to get you flexing your observation muscles and developing strategies for new ways of paying attention.

By no means feel like you have to attempt them all. Start with one idea and see where it takes you in your practice. Or consider trying one prompt each day for a month and then move on to the next. 

Notice what most people miss

Walker started a project a few years ago while he was in San Francisco without time for sightseeing. He decided to look for security cameras. He opens the book with the prompt to “conduct a scavenger hunt,” making it clear that the exercise does not need to to have an obvious point. Looking for security cameras was more an exercise in novelty than actual research. He approached it like a game, where the goal was entertainment more than anything else.

“See how your understanding of our connection to the objects around us changes, and in turn, how this changes your own process of creating.”

When it comes to conscious noticing, Walker points to the power of choosing “something that’s ubiquitous and taken for granted.” He draws from George Nelson, the author of How to See who was a longtime design director of Herman Miller. Nelson was a collector of the world around him, documenting manhole covers, street corners, public clocks, arrows, and even footprints. Try this and see how your understanding of our connection to ordinary objects changes, and in turn, how this changes your own process of creating and designing. 

Draw what you see

Photography can be the default mode now that we all have cameras constantly within arms length on our phones. Instead of taking a picture the next time you see something interesting, why not draw it? No artistic ability is necessary, and you don’t have to show the drawing to anyone else. 

When you’re tempted to reach for your phone out of boredom, go for your notebook instead (you can even find a cheap one that’s sized like your phone). You don’t have to draw everything, just draw one thing. Then repeat every day until you fill your notebook. 

For a quick challenge, draw the last room you were in from memory. Once you’re done you can go see how close you were, and what you missed.

Take a different route

Rather than using Google Maps to keep us from ever getting lost again, make it a point to engage with the world and “get there the hard way.” You can look up the directions and write them down before you go, but the challenge is to make the journey without any real time guidance from a digital device. The simple act of choosing to observe where you are without digital assistance may seem daunting, but can change the way you feel and interact with your surroundings.

“What changes if you switch up your habitual mode of creation?”

Similarly, what happens when we shake up our routines and take a different route to the grocery store or the park? The next time you go to a place you frequent, why not attempt a new route? In the book, Walker notes this tip from Jim Coudal applies to the creative process as well. Try sketching on paper when you’re usually digital, or brainstorming via phone while on a walk instead of via videochat. What changes if you switch up your habitual mode of creation?

Look through someone else’s eyes

When we take on the view of someone else, we start to see the world through fresh eyes. Walker looks to John Berger’s Ways of Seeing, where he points out that the most honest, blunt observers are children who are also insightful and imaginative. Pausing to ask, “What would a child see here?” is one way to shift into that mindset. In addition to child-like eyes, imagine viewing situations from the perspective of a historian, improv performer, a street artists, or even a bad guest.

In another scenario, take a walk with an expert. This may mean taking a tour in the city where you live, or finding an expert in any domain, be it botany, geology, or typography. “Walk together and allow your attention to be directed by others; explore your familiar world through an unfamiliar perspective,” Walker advises. As your interests develop, continue to dive deeper learning the names of plants you see, or whatever it is that you encounter regularly, but don’t know much about.

You can also go for a walk with someone else—silently—while you observe, and later discuss what you each noticed. 

Awaken your senses

Observing can engage your senses—hearing, sight, smell, taste, and touch—by hunting for things that tickle your senses. When it comes to sound, take inventory of the everyday sounds as you move through life. You can even take it a step further and think about reviewing sounds as if you were a critic, or create a map of what you observe. You can repeat or substitute this exercise with any of your senses.

“Feelings are not something we can see, but rather that we can sense.”

Ernest Hemingway said, “You should be able to go into a room and when you come out know everything that you saw there and not only that. If that room gave you any feeling you should know exactly what it was that gave you that feeling. Try that for practice.” Now take that idea, and consider how a place makes you feel. Feelings are not something we can see, but rather that we can sense. Tap into that.

Celebrate the awkward moments

As an observer, you may not always be in your comfort zone. It may even make you feel a bit uncomfortable if you challenge yourself to a meal alone without anything—no phone or reading—to keep you company. We don’t often find ourselves alone in public, but it can be revealing. 

Inspired by the book Taking Things Seriously, where writers and designers share essays about unusual objects, Walker suggests looking for the weirdest thing in the room and asking the question, “So what’s the story with that?” Consider it an ice breaker for any situation you find yourself in. 

Pursue your own ideas for noticing

There’s no one way to explore and notice the world around you. Part of the challenge is noticing what you did observe, but also what you didn’t. “It’s precisely the stuff everyone else has missed that ought to make us think twice,” Walker writes.

Walker fully encourages taking any seeds inspired by ideas in his book and pursuing it further, and even inventing your own exercises to deepen your exploration. “Give it a try,” as he says in the epilogue.

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