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Recently my life of skirting the law caught up to me…..twice. My attempt to thumb my nose at the Deep State was met with the power of law enforcement when I was pulled over at two different times for the transgression of an expired inspection sticker for my car. It is now the month of June and my sticker expired in May…..of 2024. So that means for you keeping score at home that the last time my car was inspected was May 2023.

Both times that I was pulled over in the span of one week, I was asked the same question: why did you let your sticker expire for so long?

Fair question. But to provide an honest answer I would have to dig into why I have any of the unhelpful patterns in my life. At first I just forgot to get it done. Then I got ashamed I didn’t get it done. Then that shame just became a larger pattern of my life which came to define me. Then to get it fixed would be to wonder who would I be without that expired sticker?

After the second time getting pulled over, I promised the officers that I would right away get it fixed. And true to my word, I did. $35 and 15 minutes later, I now have a 2026 expiration sticker. I have to say that I feel oddly relieved.

I also have to say that in both cases the officers were extraordinarily nice, and included one trainee who did a fine job with approaching my car.

I think the moral of the story here is that we sometimes need help from others to get over the old patterns of our lives and to create new patterns that allow us to move on in healthier and better directions.

My guest today on Experience by Design also has built a business to help people create a new version of themselves. Anya Cheng is the Founder and CEO of Taelor, a leading men’s clothing subscription service that provides personal styling and curated rentals for their customers. But that’s not all. They help their customers through a combination of expert stylists and AI. So when we are looking for example of AI being used for good, here you go. When you look amazing in your new outfit and people ask, Where did you get that? You can say, AI.

It’s not surprising that AI can help in this way because any time I’ve seen an AI character in a movie, they’ve dressed well and looked cool.

Beyond Taelor, Anya is a Girls in Tech 40 Under 40 honoree, having led eCommerce and digital innovation teams at Meta, eBay, Target, and McDonald’s.

We talk about a range of topics, such as helping customers make changes in their lives, trends in fashion across different cultures, quiet luxury versus conspicuous consumption, long-term launches versus short-term disruption.

We also talk about her career in journalism, and how telling the stories of others and knowing how to stand around both served her well in her career.

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One of the things that I am starting to notice more and more is the difference between “getting older” and “feeling older.” Getting older is something that is unavoidable as long as we’re alive. But I find feeling older comes in waves. I am finding that seeing another child graduate high school is another moment in which I am impacted by feeling older. My daughter Hailey has reached the end of her high school years, which is more bittersweet than my first daughter. This is because Hailey was born with particular challenges that made every year uncertain. The NICU doctor told us “to enjoy the time you have with her.” Turns out that we are 18 years and counting.

With her challenges, college is not an option. But given that we live in a state with good services, she moves onto something called Transitions, which is a program from 18-22 to help develop life skills, job skills, and job placement. As with any graduate, it is an exciting time and a scary time not knowing how her story will unfold. Then again, Hailey’s story has always been filled with a lot of uncertainties, also like any of ours. Every step along the way, she has authored a version of herself that is authentically and uniquely her. As much as we would all like to say the same, I really don’t know how many of us can. The freedom of self expression through which one can shine their own light can be a proposition much scarier than what might happen after graduation.

The story of your life that you are going to write and tell is in large part up to you. Ideally, I think, we would like our story to be written in our voice because it is one that we are writing for ourselves. This isn’t always possible given that our stories are invariably impacted by any number of factors beyond our control. To be able to tell our stories on our terms is a gift.

My guest on Experience by Design knows all about telling stories, and also about the importance of marking time. Michael Drew has spent a career helping people get their stories to a wider audience. A key point that he shares is that we need to find ways of connecting our authentic voice and passion to a broader audience. Michael sees his work as part of a larger purpose, which is being here in service to other people. This process involves building relationships, translating brilliance into actionable insights, and framing ideas in ways that speak to the needs of your audience.

Michael has represented many many best selling authors, so he definitely knows about which he speaks.

We also talk about his other work on the forty-year cycle of history, which is a fascinating topic to explore. It turns out that everything old is in fact new again. These cycles move from “Me” to “We” extremes, which reflects the larger social zeitgeist. Understanding this cycle can explain much of the moments we find ourselves in, and what it means for us individually and as a society.

Was a fascinating chat that ranged across many different areas, but all tied together by a focus on telling our story, understanding the broader moment we are in, living to our purpose through service, and crafting a brand that you can believe in.

And congrats again to Hailey who lives the most authentically of any one I know, and continues to write her own story.

Michael Drew LinkedIn https://www.linkedin.com/in/michaelrdrew

Book Retreat Publishing Services https://bookretreat.com/

“Pendulum: How Past Generations Shape Our Present and Predict Our Future” https://www.goodreads.com/book/show/15842812-pendulum

Parenting children is definitely one of the hardest challenges that we can face in life. But as challenging as that is, it is nothing compared to reparenting your inner child. Some of you might be familiar with that turn of phrase. It refers to the process of dealing with childhood trauma, and “short-falls” in the manner in which you were parented in the first place, especially in relation to nurturing, support, care, and emotional safety that may have been missing.

While re-parenting refers to a particular therapeutic approach, dealing with the effects of trauma is something that many, if not most, people share. And the impact that this can have on our lives can be multifaceted and complex. If you have ever gone to any recovery programs, you will know that the behavior being dealt with is only the symptom of the problem, and not the source of it. There are deeper challenges people are facing. After all, what sank the Titanic was not the ice that was visible, but the ice that was beneath the surface.

Perhaps it is not surprising that we’ve had a number of guests that are working with people in varying capacities to improve themselves, their lives, and their relationships with others. I do think that it is in some ways a Gen X thing. There is a desire to do better and be better, feel better, without the tools with which to carry that out. Thus, we have an idea of where we want to go but no clear idea of how to get there. It is hard to build a birdhouse without any tools or knowledge how to use them. You can give it a go, but the outcome is likely to be frustrating and not great quality.

On today’s show, we welcome Tammy Cho to the studio. Tammy had over 20 years of experience as a nurse, but in line with the common expression, she was having a hard time healing herself. A visit to the emergency room to deal with chest pains and heart palpitations led her to re-evaluate her life and how she was dealing with her trauma.

Out of this process, Tammy developed what she calls Energy Leadership and Self-Love mentoring. Part of this involves slowing down and reconnecting with ourselves. This can be a scary proposition when we are not sure what we might find, or if we will like what we discover when we do. When we stop pushing ourselves away, we can rediscover who we are and accept the gifts that we possess. In her definition, human design is about self-intimacy, self-empowerment, and self-acceptance. By doing so, not only do we change our relationship with ourselves, but also with those around us whether they be friends, family members, co-workers, or those we are managing professionally.

LinkedIn: https://www.linkedin.com/in/tammycho-pathtotheheart/

Website: https://pathtotheheart.com/

I’m lucky enough to live in a spot where there are a lot of trails that I can enjoy whether running, walking, biking, and even snowshoeing if we get enough snow. No matter what I am doing, I have one simple rule: if there is a friendly dog on the trail, I must stop to pet it. The opportunity to pet and engage with random dogs is one of the things that just brings me a lot of happiness. It is hard for me to understand those who are not “dog people”, especially since I mostly prefer dogs to people. I’m a sucker for dogs.

It turns out that those cute faces that dogs make and the way they endear themselves to us is not by accident, but by evolution. Being cute helps them to worm their way into our worlds. In that way, dogs are a bit of a salesperson, selling us on giving out treats, walks, toys, outfits, food, cuddles, and all kinds of pampering. I mean, sales is just about convincing someone of a course of action. Dogs are great at this, or at least they are to me because I am such an easy mark for dogs because they play on my emotions.

In preparing this, I hesitated at connecting dogs with sales because dogs are revered people and sales people less so. In fact, you could say that sales has a bad rap. Rather than seeing sales as a way of getting people what they need, sales is often viewed as a way of convincing people to get things that they don’t need and will not be helpful. But our guest today is here to talk about how when sales is done well, it is a win-win-win situation.

Doug C. Brown has spent a career trying to do sales right, creating positive experiences for customers and sellers alike. Doug talks about how sales is probably the world’s “oldest profession.” He also talks about the challenge of overcoming the bad rap of selling to get to a better outcome for customers. He describes how the metrics being tracked often are not those connected to CX success, which lead to worse outcomes. He finally takes us on the long strange trip of starting out as a vocal major at Berklee College of Music, moving to nuclear medicine, serving in the Army for 12 years, and finally ending up in sales (all of which have more in common than you might think!).

LinkedIn: https://www.linkedin.com/in/dougbrown123/

CEO Sales Strategies: https://ceosalesstrategies.com/

We are rapidly approaching the end of semester, which can only mean one thing: freedom. The end of the semester is always a weird time. It kind of reminds me of the end of a relationship where both parties have just had enough and know that it is time to move on. Let us conclude the business at hand and get on with our lives. Sure we can stay friends, and perhaps even hold out the potential of getting back together at some point in the future in another class. But right now, its best if we go our separate ways.

For those students that are graduating, it means something else entirely: time to put all that book learning to work and try to get a job. Of course calling it book learning makes me show my age, because who reads books anymore! But the point still stands: graduates are on the hunt for a job that will provide the opportunity to start adulting on a larger scale.

To get a job, one of the things that they need to be able to do is stand out from the pack of others who are also trying to get jobs. Here in lies one of the unique ironies that we have in at least American culture. The belief that we are individuals who are unique and can stand out, coupled with a strong anxiety and aversion to being different from other people. For as much as we like to think of ourselves as unique and distinctive, we really have a strong streak of conformity. This makes us no different from other societies in which standing out can be stigmatizing and sanctioned. Being the first in a parade feels a lot safer than standing out.

But standing out is important in terms of showing others who we truly are, and living in a way that feels authentic.

My guest today on Experience by Design knows all about the challenge and importance of standing out. Judy Winslow of Unforgettable Brands is a self-described Brandologist who has spent her life standing out and being around creatives who do the same. Judy moved to Sarasota, Florida because it was a place for unique personalities and creative artists could come together and celebrate standing out. As a person trained in graphic design, she knew the importance of self-expression in her work. Now, she works with leaders to create cultures in which people can celebrate their unique characteristics, have freedom to express it, and transform vision into reality.

We talk about giving permission to be audaciously authentic. She describes how our brand is in action all the time, and that as humans we are here to stand out. She talks about how she was influenced by Marty Selligman, the godfather of positive psychology, focusing on what works well and how to build on those successes. She also reinforces the point that before you have customers, you have employees, and that personal and professional development is not just about improving ourselves, but helping to improve others as well by being able to better show up for them.

Judy Winslow https://unforgettablebrands.com/

LinkedIn: https://www.linkedin.com/in/judywins/

Springtime in New England is the worst. As I sit here on another cold and rainy “spring” day, I’m reminded of what I was told by someone when I first moved to Boston 25 years ago: “Springs in New England are wonderful.” I never trusted another word that person said after I experienced it for myself.

Part of it is the waiting for something better that you hope is right around the corner in terms of sunny skies and warmer weather. And then two weeks later it will be 87 with 1000% humidity. But those two weeks of actual nice weather are pretty wonderful.

But the waiting is rough, as transitions often are. Any kind of transition can be painful and wrought. Think about the transitions that you have gone through in your life, what it felt like, and what it took to get through it.

It turns out that in many ways we are in another transition right now: something called Late-Stage Capitalism. We can look at the technological transitions taking place, the accumulation of wealth and the growing disparities it is bringing, environmental degradation, and the seemingly increasing number of financial crises as indicators of this transition being underway. But what comes next?

To talk about social transformations and transitions, we welcome Jaime Schwartz to the Experience by Design studios. Jaime's expertise crosses a lot of areas, which is a good thing because we talk about the need to have breadth of knowledge and experience as we enter what he calls the Co-Creation Economy.

Part of this lies in finding better ways for people to work together, using AI as a tool to help facilitate collaboration and flow. Another part of this is focused on helping corporations align their brands with a higher mission and purpose. Finally, we have co-creationism in art, where new technologies and approaches to expression create new ways of sharing, owning, and co-creating artistic expression.

Overall, our conversation digs into how we successfully transition to embrace the promise that technological innovations have for making our lives better, and hopefully not being run over by it. And how by coming together we can accomplish great things.

Team Flow Institute: https://teamflow.institute

Mrkd Art: https://mrkd.art

Brand Therapy: https://brandtherapy.coach

I always feel a bit bad complaining about getting older, because getting older is not a privilege afforded to everyone. At the same time, getting older does present certain challenges. I was able to get a glimpse into aging the other day when I went to get my eyes examined. Turns out that the middle of the day at the eye doctor is peak time for those who are, shall we say, of a demographic much more advanced than I. It definitely was a glimpse into a future that I am steadily approaching, and makes me reflect on what it will be like to be older then. There are so many things that have increased accessibility for those who are older, designs that make life more manageable and easier to negotiate. At the same time, a lot of challenges remain, especially in a society in which technological change is fast enough to make even the most savvy feel left behind.

So, clearly there is a lot of work to be done. And that is why we welcome our guest today on Experience by Design. Sheng-Hung Lee is a Doctoral student at MIT. There he is involved in the AgeLab, where they have the aim “to improve the quality of life of older people and those who care for them.”

Sheng-Hung has been involved in a wide range of service design initiatives, and has a list of awards and recognitions to prove it. He also has worked at companies like Ideo as well as Continuum, and is part of organizations such as the World Design Organization and the Industrial Designers Society of America.

We talked about a range of topics related to designing, systems, and aging. He talks about what brought him to the field of design out of his background in engineering. Sheng-Hung describes how we have to move from the idea of designer as hero, and work more collaboratively to address complex challenges. Part of that is the need to go beyond siloed thinking and integrate ideas from a variety of backgrounds and experiences. And we talk about the need to move beyond focusing on tangible stuff as a primary motivation, and have the space to explore, learn, and synthesize.

Sheng-Hung Lee Website: https://shenghunglee.com

MIT AgeLab: https://agelab.mit.edu/

As I’ve mentioned before, one of the great things about doing a show like this is the fascinating people I get to talk to who are coming at experience design from many different approaches, perspectives, and backgrounds. One of the groups that I perhaps enjoy talking to the most (no offense to anyone else) is artists. I’ve always admired the ability to turn imagination and passion into something that expresses one’s soul in a way that can move others. Talking to artists about their work kind of creates a sense of purity of work in terms of representing an authentic self. I don’t want to overly dramatize or prematurely canonize them. But artists can do really cool stuff that brings life and light into the world.

And it feels like every day more and more, we need some life and light brought into the world. While art changes, our need for art never changes.

My guest today is artist Will Owen. Looking at Will’s website, it lists his primary mediums as sound, sculpture, and food. That’s right. Food.

Without that is a larger preoccupation of culture and the world in which we live, seeking to represent it in ways that stimulate thought, expose us to its beauty, and contemplate its possibilities.

Growing up in Appalachia provided an opportunity to explore how to have fun and create with whatever was available. Before we had the concept of a ‘maker space,’ his childhood was a maker space in which risks could be take in the pursuit of having fun and filling time. Out of that comes a creative spark and fundamental appreciation for the natural world. He describes himself as being ‘obsessively curious’ and being promiscuous with materials, which he owes to his childhood and the collaborative explorations with his friends.

Today he is part of many different collectives around the world. He is part of the Flux Factory in New York, and has worked with artists in Russia and Taipei,

We talk about making something loud with no budget, the indelible reciprocity of making together, the porousness needed to engage with performative audiences, and his obsession with supertemporary communities. We also talk about the bus experiment, a traveling exhibit from Manhattan to Philly.

Will Owen - https://willowen.net

Flux Factory - https://www.fluxfactory.org/