When you’re under 40, buying a life insurance policy may seem about as practical as buying a Humvee. That makes insurance a tough sell for a 165-year-old company like MassMutual. To find a way to become relevant to this generation, MassMutual partnered with IDEO with a mission to get young people interested in their own spending habits.

Over the course of two years, the teams set out to learn about how people across the US spend and save their money, and they uncovered a simple theory: you either have a smart money mindset or you don’t. When it comes to being mature about financial issues—chipping away debt, saving to buy a car—it doesn’t always come naturally. If anything, many feel disconnected from money-related matters, even if it’s in their best interest to know more.

"I hate going to a bank and not really knowing what I am doing when it comes to money," said Simon Bowers, a 31-year-old who works in public relations, featured in an article in Fast Company about the MassMutual-IDEO collaboration. "They don’t seem to take into account that this might be scary for us."

So how to invite this wary demographic to the table? Design an accessible way to meet them wherever they are: online and on their phones. IDEO helped build the new venture from the ground up—designing a brand identity and experience focused on transparency, meeting users where they are, and helping people navigate complicated financial situations so they can live life on their own terms. It’s called Society of Grownups, and you can think of it as a sort of master’s program for adulthood. Each piece of the program builds on a common vision that continues to iterate every day.

After building and testing full-scale, live prototypes, the brick-and-mortar Boston location opened in 2014 and operated much like a supper club—a warm, inviting space where young people could hang out, feast on delicious meals, attend talks, and learn about things like 401Ks, living on a budget, and how to pick good, cheap wine. After two years of continued prototyping, MassMutual recognized that the digital channel has the most potential to grow and closed the brick-and-mortar location to focus their investment in building out the bespoke online financial tools to reach more people across the nation.

From leeches to gene therapy, how we treat sickness has changed beyond recognition over the centuries. But one question asked by ancient healers and modern doctors alike remains the same: “How are you feeling?”

“We’ve had the ‘quantified self’ for a number of years—sensors that measure steps, weight, blood pressure,” said Bruce Hellman, cofounder of UK-based digital health startup uMotif. “But by only focusing on the quantitative, we miss the whole picture of a person.”

Hellman cofounded uMotif in 2012, inspired by the self-awareness he gained when tracking his sleep after his baby was born. uMotif gives people the tools to record and track their mood, sleep, and clinically relevant symptoms like dizziness or breathlessness on their mobile phone app, and share the resulting data with their doctor and care team to better inform appointments, and treatment plans.

Named as one of 50 UK "scale-ups" that could grow to over £100m in revenue by not-for-profit organization Silicon Valley Comes to the UK, uMotif’s software and apps have been deployed in dozens of hospitals, and profiled in The Guardian, The Daily Telegraph, and The London Times. With a view to scaling strategically, Hellman applied to IDEO Europe’s first Startup in Residence, a three-month-long program to accelerate companies through design thinking. “We brought the whole of uMotif to IDEO: product, organization, branding, approach, and business model,” said Hellman. “We were keen to re-consider just about everything.”

During the residency, the uMotif team embedded with IDEO’s London studio to work closely with an eclectic team of interaction, business, and communication designers, and design researchers, to explore every aspect of the business.

The team found that although uMotif’s organic growth had reflected the rapidly expanding digital health market, the offer was somewhat fragmented as a result. In response, uMotif decided to tighten its sales focus from 14 branches of medicine to just two: oncology and cardiology (with mental health as an R&D area).

In-depth interviews with patients, nurses, doctors, and executives revealed a clear opportunity: “simple symptom tracking for people going through an acute or serious period in their health, to activate and extend the patient-care team relationship,” Hellman says. The focus switched from the Quantified Self to the Qualified Self, coined by the team to reference uMotif’s unique approach to measuring how people feel.

Designers set about reconfiguring and prototyping aspects of the brand, product, business, and organizational model for delivery. Whereas the original uMotif product had been designed with a single clinician in mind, the team designed a new dashboard catering for the reality of modern healthcare—multiple caregivers.

Ultimately, uMotif’s offer is not just about helping patients understand their own health; it’s about providing meaningful insights that enable them to have richer conversations with their care teams—allowing them to work together to improve care plans and outcomes.

“We are a much more focused, confident, and clear organization, truly prepared to scale sales, delivery and clinical impact,” says Hellman, referring to the impact of their participation in the Startup in Residence program. Now back in its own headquarters, the team takes with it a toolkit of IDEO systems and processes with which to run their business and to apply to new projects, products, and services.

“Health systems around the world are quickly adopting digital channels,” he said. “We aim to be at the forefront of this inevitable shift, using design thinking to put people at the centre of their care, improving quality of life, treatment outcomes, and healthcare experience.”

WATCH: uMotif: Sam's Story.

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IDEO designers wanted to take on a challenge: How might we help kids make better decisions around food and being active?

Designers moved forward with three concepts that addressed this challenge from three completely different directions:

• Top Chops, a hands-on cooking adventure that builds kids’ confidence in the kitchen by working toward becoming a Top Chop “master chef.”
• Daredevils, a wearable device that measures the intensity of energy exerted, but doesn’t prescribe the activity, which kids can use to dare each other to reach activity goals.
• Presso, a set of child-size kitchen tools that slice and dice fresh food in imaginative ways, making cooking fun and helping kids feel they have a role in making their own healthy food.

The design team behind this work was featured on 60 Minutes, and some of the resulting concepts were featured on CBS This Morning.

In updating the popular and industry-defining PalmPilot, Palm Computing wanted to reposition the next-generation Palm V as a high-design accessory to set it apart from its many imitators.

Together with IDEO, it crafted a sleek, elegant device, half the thickness of the original in an anodized aluminum housing. Incorporating an internal lithium-ion battery that recharges in the dock, the side rails act as an open architecture to provide attachment for a variety of styluses, cases, and other add-ons.

“What's going on there?” asked my colleague Ed, in his usual bouncing demeanor, pointing at my phone propped in its handy, commonly-found, IKEA glassware receptacle.

I was in the last weeks of a project, building out a mobile-first website to showcase our final deliverables. I was going about my usual process, with a minimal set up: designing the UI in Sketch, mirroring the artboards on my phone.

“What? This?” I replied, adjusting the angle of my glass full of iPhone.

“Yeah. I've never seen anyone do that before,” he chimed back.

It dawned on me that this behavior in my design quiver—something I'd been doing since my very first mobile design moment—may not be that common.

Instead of having to stop and pick up my phone every time I need to check my work, I just plop it in a glass, adjust the angle, and check my design’s mobile readiness with a glance.

The adjustability and the “there's probably one lying around” factor of a drinking glass elevates it to a handy design tool that I’ve used throughout my career.

And once you’ve shipped the design, it also makes for a great vessel for a celebratory swally.

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Human-centered design requires us to observe human behavior with beginner's eyes, so that we can spot the innate ways people interact with the world around them. We call these intuitive and unconscious reactions Thoughtless Acts, and IDEO designers collect photos of them to inspire their work.

Creativity Challenge #3: Jumpstart an ideation session

Here’s one quick, simple exercise to get creative muscles warmed up. We learned it from David’s mentor, Bob McKim, back when David was a product design student. It’s called Thirty Circles, and you can do it on your own or in a group. The goal is to push people to test their creativity by turning circles into recognizable objects in a very short period of time.

Tool: Thirty Circles Exercise
Participants: Solo or groups of any size
Time: 3 minutes, plus discussion
Supplies: Pen and a piece of paper (per person) with 30 blank circles on it of approximately the same size. (We recommend printing it on an oversized sheet of paper. You can also just ask everyone to draw their own 30 circles on a blank piece of paper.)

Instructions

Step 1: Give each participant one 30 Circles sheet of paper and something to draw with.

Step 2: Turn as many of the blank circles as possible into recognizable objects in three minutes (think clock faces, billiard balls, etc.)

Step 3: Compare results. Look for the quantity or fluency of ideas. How many people filled in ten, fifteen, twenty or more circles? (Typically most people don’t finish.) Next, look for diversity or flexibility in ideas. See if the ideas are derivative (a basketball, a baseball, a volleyball) or distinct (a planet, a cookie, a happy face). Did anyone “break the rules” and combine circles (a snowman or a traffic light)? Were the rules explicit, or just assumed?

Tips from the field

Besides being a great warm-up exercise, Thirty Circles offers a quick lesson about ideation. When you generate ideas, you are balancing two goals: fluency (the speed and quantity of ideas) and flexibility (ideas that are truly different and distinct). We know from experience that it’s easier to have a great idea if you have many to choose from. But if you have a lot of ideas that are just variations on a theme, you might really only have one idea with twenty-nine other versions. When you combine fluency and flexibility, you can generate a rich array of concepts to choose from.

This post was taken from Chapter 7 of Creative Confidence. Purchase the book for more on how to use creativity to solve problems.

Everyone is creative. This belief runs through everything we do at IDEO, and in 2013, it led my brother David and me to write a book that would help others—even those who don’t think of themselves as “creative types”—to unleash their creative potential. Creative Confidence has inspired thousands of people to adopt a creative mindset and apply it to the diverse real-world challenges they face. In this series, we’ll share some exercises from the book that can help you approach your challenges from a new perspective.

How could Fintona make their newbies feel comfortable saying, “I don’t know, but I’ll find out?” They began by experimenting on themselves. Their first idea was a goofy one: arm each newbie with a Bat Signal—a flashing red police light that newbies could trigger any time they were stumped to summon help from across the call center.

The first day of the experiment, it was clear that the lights weren't working. Newbies who were already uncomfortable saying, “I don't know,” were even more uncomfortable turning on a flashing emergency light that screamed to the whole floor, “I DON’T KNOW!” When other service agents saw the signal, they just assumed that someone else would jump in and help. The experiment failed.

The team needed to iterate. They thought that maybe each Bat Signal needed a Batmanager—a dedicated leader who could watch the lights and swoop in to save the day. So, the team moved the lights to the managers' offices and asked them to be on the lookout.

That didn't work either. Newbies still felt singled out, and the Batmanagers weren’t at their desks often enough to act as a reliable safety net. Realizing the team needed a private way to call for help, they created a private chat channel—the Bat Chat—where newbies could connect directly with experts from Fintona’s specialized departments.

But the experts didn’t answer any questions. In fact, the only answers that newbies got on the Bat Chat were from other newbies. That gave the team an idea: They would launch the Bat Chat across the entire call center. They figured that veteran agents must know the answer to 80 percent of newbies’ questions, and they might be a safer resource than some stranger in another department.

Finally, success. The Bat Chat took off like crazy. Surprisingly, it wasn’t newbies who first started using the chat, but veteran service agents asking each other questions. As more veteran voices spoke up (or typed up), the newbies started asking their own questions and getting immediate answers.

The Bat Chat was the perfect solution for this team. But, there was no special analysis that they could have done beforehand to figure that out. No market research or benchmarking data would have suggested it. They had to build, fail, iterate, and repeat to find the answer. And once they found it, it didn’t need careful change management to extend it to the rest of Customer Support. It spread by word of mouth, and became a source of pride because the team found their own solution.

Fintona learned some remarkably similar lessons to what Harvard professor Teresa Amabile found in her two-year study of the culture of helping at IDEO: Newbies don’t need to be singled out. They need to see that everyone—even their most successful colleagues—need help sometimes.

This post is an excerpt of a longer article I wrote for Harvard Business Review. Read the full story here.

This article is excerpted from a longer story in Harvard Business Review.

Fintona Financial (not the company’s real name) was growing fast—so fast that their Customer Support call center had tripled in size. They couldn’t recruit fast enough. Many new service agents were pulled out of their two-month training program in as little as two weeks. Eager to look good in front of their bosses, these newbies struggled to answer tricky questions—all too often, they would give a right-sounding answer instead of saying, “I don’t know,” and asking someone for help. This not only triggered inceased call volumes but also began to erode Fintona’s customer satisfaction scores.

I first began creating cartoons as a way of communicating with Marta, my wife, when we started dating. I hate texts, so instead, I would draw a cartoon, take a picture, and send it to her. We are both New Yorker readers, and at some point she said that mine were better than most of the the magazine’s. She is not biased. Neither is my mom, also a fan of mine, so I thought it was worth the shot.

I submitted for the first time in the summer of 2016. A former coworker is married to David Sipress, a classic New Yorker cartoonist, and one of my favorites. David kindly offered to take a look at my cartoons. He said that they were totally publishable, and encouraged me to submit to the magazine. He also shared a few pro tips, like that The New Yorker very rarely publishes puns, and when it does, it’s almost always ironically (almost a quarter of the cartoons I sent him were puns).

Almost every week, the New Yorker cartoon editor meets with artists and reviews their work. This meeting is open to anybody. You just show up, sign up, and present your cartoons. So, one hot day in June, I printed my cartoons and showed up at the offices at One World Trade Center, ready to make an impression (good or bad).

The great thing about the cartoon meeting is that you sit with the editor and he gives you feedback, right there. Back then, Bob Mankoff was still the cartoon editor. The opportunity to have a private critique session with somebody like Bob was fantastic. On our first meeting he said that he liked my cartoons, that the drawings were very good, and the jokes were “not bad,” which is quite a compliment coming from him. He picked four of my cartoons and I was thrilled. I thought that I had it made and I was going to start selling cartoons right away.

Not quite. It turns out, the meeting is just the first filter. The editor has a subsequent meeting with David Remnick, The New Yorker’s editor, where he shows him his selection of cartoons for the week. David decides which to keep, but before the magazine buys anything, they will peruse their archives—and cartoons from other major publications—and check that they have not published anything similar first. It’s quite the process. They didn’t buy a cartoon that time. Nor the following week. Nor the next one.

In my meetings with Bob, he was quite blunt, but always funny, and he often built on my cartoons, coming up with new iterations or different ideas for the same joke. The main criticism I received was that my captions were not sharp or punchy enough. That makes sense because English is my second language. In Spanish, I am hilarious.

After many rejections, you might think I’d have gotten discouraged and stopped trying, but I have fun making cartoons. Rejection is just a part of the process that every cartoonist has to endure. It took David Sipress 25 years of submissions until The New Yorker published his work. Bob Mankoff himself sent more than 2,000 cartoons before he sold his first one. However, there are geniuses like Ed Steed who sell after their first submission. He is my favorite. I hate him with every fiber of my soul.

I’m also a bit of a masochist, perhaps as a side effect from attending a Catholic school for 13 years. I am an atheist now, but I still think that the only way to reach salvation is through suffering. I come up with projects that require a high level of commitment, take a painstaking amount of work, and provide low returns. I am very smart.

You can say that there is some sense of pride in a perfect record of 100% cartoon failure—otherwise I wouldn’t put them up with a big red REJECTED stamp on them. But the thing that I am most proud of is that Bob Mankoff said of one of my cartoons that it was the worst he had seen in his entire life. Hell, that’s something to brag about. I said, “Don’t worry, I can do worse,” and he burst out laughing.

However, I am not going to lie. Sometimes it hurts, especially after a few rounds of rejections. But that’s just my ego itching. Who wants to be published in The New Yorker after all? What a bunch of snobs.

That being said, I plan to go back to The New Yorker very soon to meet the new cartoon editor. I might get luckier with her. Getting into the rhythm of drawing ten cartoons every couple of weeks helped me hone my drawing skills, and I’ve missed it since I stopped. The style of the drawings I make for our projects, which often end up in front of clients, is the direct result of those dozens of hours of making cartoons. It’s like illustration gym.

And it’s interesting, the more cartoons you create, the more ideas you generate. At first I was afraid of running dry, but I was surprised when the opposite happened. I have a little red book where I write down ideas for cartoons, and the list keeps growing.

But, most importantly, I just enjoy making cartoons. Sometimes you can see me sitting by myself in a cafe, laughing out loud at my own drawings, which is quite a pitiful scene if you think about it. We are all going to end up as human compost, so we might as well laugh a little on the way to our graves.

Thanks to Lawrence Abrahamson, Michael Hendrix, and Lindsey Rodabaugh for encouragement and help with the exhibit.

IDEO communication designer Juan Astasio knows a thing or two about rejection. His great ambition is to publish a cartoon in The New Yorker. In the last three years, he’s submitted more than 100 cartoons and met with an editor to discuss his work ten times. Still, nada. But instead of being discouraged, Juan has embraced his failure, sharing his jokes with the New York studio on the walls of one of its phone booths. Here’s what he’s picked up in the process, why it’s worth it for him to keep going, and what, exactly, he’s learned from failure.

I help organizations cut through complexity by shaping how they show up, through brand strategy, identity, and storytelling.

Working at the intersection of brand and business, I bring an editorial eye and a bias toward making—turning ideas into tangible experiences that people can understand, trust, and believe in.

My work spans government, healthcare, financial services, media, and consumer goods, from launching Gen Z-focused ventures to building innovation labs and reimagining legacy brands. I relish moments of ambiguity and enjoy translating across teams, perspectives, and priorities to move ideas forward.

I started my career in editorial and digital design, shaping cross-platform experiences and identity systems in publishing and agency environments. That foundation still shapes how I work today: I’m detail-oriented, collaborative, and overreliant on the Oxford comma. I hold a BFA in Visual Communication from the School of the Art Institute of Chicago.

For 25 years, I've asked the same question: Who does this design exclude—and what are we going to do about it?

My work spans human-centered strategy, inclusive design, and qualitative research, with clients ranging from Microsoft, Google, and Verizon to the National Science Foundation, and San Francisco Unified School District.

Before IDEO, I taught elementary school in East Palo Alto and spent a decade doing design work with social service organizations—where I learned firsthand what it costs people when systems are built without them in mind.

I am currently writing User Error, a nonfiction book about digital access and the design decisions behind it. I live in Oakland, California.

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My expertise spans brand, communication, and product design across tech, education, the arts, and social impact.

I believe great work demands both high-level vision and obsessive attention to detail, and only happens through collaboration.

I bring an inclusive, hands-on approach and a deep understanding of business, which enables me to consistently deliver excellence while always asking why.

Before joining IDEO, I worked at the brand firms Pentagram and VSA Partners. I began my career as a designer, leading teams at the School of the Art Institute of Chicago and the Milwaukee Art Museum. I hold an MFA in graphic design from Maryland Institute College of Art and a BFA in communication design from the Milwaukee Institute of Art & Design, and have taught at some of the best design schools in the US.

I am responsible for IDEO’s long-term success in China and working with clients to use design as a tool to enable growth. Specifically, I have helped Chinese companies design holistic brand solutions through the development of their products, communication, services, and innovation teams, and I have helped multinationals expand their presence and influence in China.

I advise global leaders on developing China-led innovation and capabilities.

In over 15 years in IDEO Shanghai, I have worked on projects that use design to elevate the quality of the experience of healthcare products and services, streamline processes that increase productivity, create spaces and programs that promote and enable inclusive communities, and build next generation mobility solutions that are planet-positive.

Before joining IDEO, I worked at Philips Electronics and the Electrolux Group in Italy, the Netherlands, and Singapore on a number of breakthrough commercial products. I am a member of the Young President Organization in Shanghai.

Most AI products today are built for work—a space with clear problems and established systems. One founder noticed a gap: personal life is messier, harder to systematize, and mostly left behind by the AI boom. So she built Cue, a personal AI that lives inside iMessage and group chats, to go where the other tools haven't.

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In this episode, Becca Carroll, IDEO's Chief Strategy Officer, talks with Sida Li, co-founder and CEO of Shared Context Lab, about staying anchored to a human need while the technology around her keeps changing shape, why she treats her business model with the same rigor she'd bring to a product, and what it feels like to build a company at this particular, disorienting moment in AI.

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The conversation also gets into how Sida makes design decisions: the language Cue uses to describe itself, the tradeoffs behind building inside iMessage instead of a new app, and a real story about a business idea that didn’t pan out.

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This is the second in a two-part series profiling founders from IDEO's Startups-in-Residence program. The first conversation is with Johannes Seemann, founder of Sooner, on designing GenAI for the emotional side of money.

Most personal financial tools are built to run the numbers and optimize towards a budget. While that works for some, most people experience money as a lived relationship that does not neatly fit into a spreadsheet. Johannes Seemann and Becca Carroll discuss why money is emotional before it is mathematical, and what a human-centered approach to building a generative AI financial product looks like in practice.

Mina Seetharaman talks with Scott Shigeoka, author of Seek and Head of Curiosity Cultivation at the Eames Institute, about what distinguishes genuinely curious leadership from performative curiosity, how power dynamics shape curiosity, and why practicing curiosity can restore energy rather than drain it.

Mina Seetharaman talks with David Epstein, author of Inside the Box and Range, about why total freedom often produces average work, how leaders can design useful limits on purpose, and what organizations such as General Magic and Pixar reveal about the relationship between boundaries and creativity.