Podcast: Michela Abrams — Planning for the Unexpected

Michela AbramsEpisode 23 of the NewRetirement podcast is an interview with Michela Abrams, the former CEO of Dwell Magazine. They discuss dealing with sudden life changes, planning for the unexpected, design and re-invention. Michela lives here in Mill Valley California and joined us live in studio. We cover her evolution as a silicon valley executive to CEO of Dwell to Founder of her own design consultancy, and how her work & personal life evolved as she faced the unexpected. Michela brings a great perspective on the topics of design, community, re-invention and personal growth.

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Full Transcript of Steve Chen’s Interview with Michela Abrams

Steve: Welcome to New retirement podcast. Today we’re going to be talking with Michela Abrams, who was the former CEO of Dwell magazine about dealing with sudden life changes, planning for the unexpected, design, and reinvention. I consider this the second of our “real life stories”, the first being with Bruce Goldberg, the former DEA agent. Michela lives here in Mill Valley, California and is joining us live in-studio. Part of what we’re trying to do is help people learn other people’s experience. Michela has dealt with some massive loss and disruption in her life for the last two years, which has led her to reassess her life and make some different choices. I imagine we are going to cover some difficult topics today, but also hopefully come away with some great insights and lessons. So with that Michela, welcome to our show. It’s great to have you join us.

Michela: Thank you. I’m thrilled to be here.

Steve: Yeah. I appreciate your time. So I just want to dive in and usually, we like to open up a little bit with people’s story and a little bit where you grew up and add maybe about your family and background.

Michela: Great. All right. So the product of very young parents at University of Oregon and who then were ordered back to the bay area by my mother’s parents and told, “You, both, will go to work and we’ll help you with Michela and then we’ll tell you if you should have any more children.” And they didn’t. So fast forward to upbringing really then went to Los Angeles when my dad was transferred. And kind of growing up as an only child with such young parents, you’re really like growing up together. And so I kind of felt like an adult when I was four, I think, and that might be seen as a blessing and a curse. But it was really wonderful because I was always part of all these fascinating conversations and other kids my age kind of bored me because I was used to all the adult orientation.
And my father was president of a cosmetic company. My mother was a professor of speech and language pathology. So put those two things together and you get a journalism major. I went to UCLA and then to Cal Poly, San Luis Obispo for a much more practical version of journalism rather than CALM theory. And came out and used my writing skills for sales and marketing because honestly, I was thought I was going to go to the LA Times right away. And they said, “No, no, no, you start in Bakersfield or Poway or Fresno.” I’m like, “Okay, no, I’m not going there.” So I immediately went into advertising and marketing and built my career around that.

Steve: Yeah, I was looking at you on LinkedIn and it looks like you had your early career … started really in Silicon Valley and with computer world and Macworld and things like that.

Michela: Yes. When all my friends were saying, “Why did you choose such a narrow field? I mean really computers?” And about seven or eight years they were going, ‘How do I get into that business?”

Steve: And I think that trend’s been continuing for-

Michela: A long time.

Steve: For a while now. And when we chatted earlier, I think you mentioned you had met Steve Jobs. Is that true?

Michela: I did. He would come to our Macworld sales meetings and tell us what he thought about the advertising. Usually it was choosing five or six advertisers that he didn’t really like the creative and asked if we’d please go tell them to change their creative or we do it ourselves and design it because he didn’t really like it mucking up the magazine that he had to approve at the beginning, pretty much every issue.

Steve: Well, any big impressions that you had from meeting him.

Michela: Well, very much in retrospect, right? Not Understanding the context of his fastidious attention to detail in every way: The fonts of the magazine, the white space, the cadence of the articles, how many of them, the photos that were used, every aspect that you can imagine he scrutinized really. And then we certainly came to know him in the later years when he went back to Apple doing very much the same thing, but with an entire global brand. And I always say, the technology that makes up … or what it is? No. Is it the beautiful boxes and the fonts? No. Is it the glass building that you walk in and speak to a genius? No, it’s everything, right? It’s that attention that every single touch point of a brand is your chance to make that impression and build that relationship and nobody does it better than Apple did. And he really is responsible for that entire focus and direction.

Steve: Yeah. I think what’s interesting about him and a lot of people don’t know is, he’s actually not a super hardcore tech person or he wasn’t, he was much more of a kind of overall product, brand or experience person like you say. I know that early on he did invest in … you’re talking about fonts, he brought fonts to computing. They didn’t really exist before. He kind of invented them and said delivered them through the Apple platform, which has continued up to this day.

Michela: Yeah. I mean this is kind of the way back machine, but when I became the western vice president of computer world, they didn’t give you a computer. So I brought my Mac everywhere I went, right? And I got a letter from the publisher. A letter, not an email. A letter from the publisher. It said, “Michela, I don’t know if it’s a good idea to have your letters going out from a Mac with that font because it really looks far too humorous and light rather than the integrity of fonts coming out of IBM machines.” And I look back on that and it feels like the stone age now that I just think, “Look at how far we’ve come.” And that’s only 20 years ago.

Steve: Right. That’s amazing to hear that story. Well, at least he appreciated the impression that the using fonts and the design kind of had. So that’s cool. Any other kind of Silicon Valley kind of luminaries that you’ve bumped into that come to mind?

Michela: Well, I used to meet with Marc Benioff when he was at Oracle and also there was another CEO, a Larry Ellison, who would sit in on agency meetings and the annual RFP session to really decide what Oracle should be doing. And it was my largest account at computer world, so it was a big deal. And he used to try and say, “Well, if I could give you a few more pages, if the editors would just be a little nicer sometimes.” I said, “I’m not going to be able to take those pages because there’s that thing called Church and state, that little thing, that is the foundation of journalism and we really adhere to that.” There is Michael Dell and easy, easy person to get to know, and so self-effacing, so humble, clearly focused on what he believed was going to be in his brand, the complete democratization of the desktop, right? And affordable ways so everybody could have them. And Carly Fiorina.
When I think about who the players were at that time and they were not so far up on multi-billion-dollar giants with the exception of HP, that they were really accessible and they really got involved in things that you couldn’t even imagine them doing today and they wouldn’t be involved today. So it was a special time. I wouldn’t trade it for the world. And again, hindsight being kind of a great context of history when you think of your own. And I think, look at what tables we were setting up and having dinner with all these people and then, of course, realizing all those questions you should have asked.

Steve: Yeah, I bet that people will look back at … because Silicon Valley in California, there are these waves and bubbles that come and each one is different, so hardware, software, and then the web, and mobile, and blockchain, and everything else. And I bet if, for each one of those, the people in those phases will look back and be like, “Oh yeah, I was sitting around with Larry Ellison or the Google guys or whatnot.” And say, “Hey, look what we’re doing it that at that point in time with Mark Zuckerberg or whoever.” So, okay, interesting. Well, I appreciate you sharing that context. So for our users, one of the big things that we want to help people with is kind of learning for other folks and taking lessons. And so I know that you’ve kind of gone through this really huge transition in your life in the past two years and I would love to kind of hear your story and some of the big lessons that you’ve taken from that.

Michela: So you already have heard that I’m the only child of really young parents. But unfortunately lost both of them in the last three years. So on top of then losing my husband two years ago this week, I’m creating a chapter that in a million years I didn’t think I’d be doing. I just was so certain and I had so many images in my mind and stories about how we’d be all growing old together. My husband was an only child. My mother was an only child. My dad, thankfully, was one of eight, so there is some family there. But we were very close. They moved to Mill Valley from LA in 2003, thank heavens, so they could be close to their only grandchild. And so I just thought, we’re going to be kind of 80s and 90s.
My husband was only eight years younger than my mother. My mother only being 19 years older than I. And all that disappeared in the last three years, including my best friend, which was the reason we moved to Mill Valley because she and her husband said, “You just have to be here and so we can do more together and we’ll raise our kids together.” So there are no absolutes, right? But if I were just to use some two opposite ends of a spectrum, you have a choice to curl up under a tree, and wonder why all these has happened to you, and the why me or you can take your time to grieve and realize it’s a long process. It really doesn’t end and that you’ll never be the same and you don’t want to be, you wouldn’t choose to be.
But it does mean that you have an opportunity to continue to live and make a very full life. And so what I do is I imagine my husband, and my parents, and my best friend Alicia standing in front of me saying, “Look, we’d love to be there with you, but we can’t and it sucks, but we’re not there. So you better just grab the reins and have a rocking fabulous life in every way that means. And you and Taylor hold each other up and build a really rich, full professional and personal life and whatever that means to you.” So anytime I start to kind of get weak knees about it being daunting or why am I doing this? Am I alone? I think I’m not alone. I have an amazing network of friends and extended or chosen family, as I like to call them, and that really has, for sure, propelled Taylor and me to feel really good about being happy, number one, and about making some choices.

Steve: Has your network gotten stronger, do you think here since this happened?

Michela: Yeah.

Steve: Okay, that’s good.

Michela: Part of it is because it’s kind of just the truth when a friend and a network has a lot of loss, everybody is kind of on heightened alert and people who thought of you and would call you are like, “Wait a minute, we want to be there for you.” And it’s really amazing to see a network of people that I’ve always adored, but they’ve all shown up in such an important way in terms of always having reassurance that I’ve got a huge foundation of people who care and love Taylor and me and are supportive.

Steve: That’s great. It’s great that the people are coming together around those and providing that support. I was actually listening another podcast on the other end of this about how the suicide rate for males is middle … sorry, kind of middle-aged males has been rising. And first, they thought it was due to kind of the weaker economy for a while around the last downturn in 2008, 2010. But now some folks are saying it’s kind of more cultural. That really, it’s due to social isolation that the kind of fraying of the social network and it is leading people to feel much more isolated, especially men. So it’s nice to hear that your friends are coming together in support. Super important. So was any of this expected or did this kind of happen out of the blue?

Michela: They were in each case. It was exactly a year to the day they were diagnosed-

Steve: With cancer.

Michela: Yes. In all four instances. Yeah. And really, really healthy people. So it kind of defies the, “Oh well, it was that.” Or, “Gee, they never exercise or they didn’t do this.” No, we’re talking about really in great shape people. So it kind of not only rock your world because you’ve lost them, but your whole idea of, “Well, what does it mean to continue to build a healthy, vibrant life so that …” And ostensibly we all do that, right? So that we can live longer as long as it’s a quality life. So it shakes you up there too. And even though a year sounds like a reasonably long time. When you’re going through it, it is warp speed.

Steve: Yeah. You’ve got your daughters in college. I have a son who’s a senior and I’m like, “Okay, he’s out of here in less than a year.” Now he’s out of here to nine months, now he’s out of here and say, “Hey, that’s …” You can see just how fast it goes. Wow. So I remember you sharing a story just about Alan being super prepared and he kind of was totally organized financially and stuff like that. Did he have everything kind of put together for you?

Michela: I mean, no exaggeration, a keystroke away. And he would always say that to me. Well, once a couple times a year, he’d say, “Now I just want to make sure you know where everything is.” Because the truth of matter is, I’d go off to work the last 15 years being the CEO of Dwell and Allen ran the house. He was the homework go-to guy. He was the financial mind. He did the investment. He did it all. And he’d just say, “Now, here is this key and if you open this, it’s an actual tree down to this and to these and here’s you find this. If you’re looking for that key, you’ll find it here. The passwords are here.”
I mean, it was absolutely all there in a way that I can’t imagine what people do who don’t have that. And yet I know the reality is most people don’t have that. And he had a complete presence of mind up until the last breath. And so he was saying everything each day. “Now what about this? Do you know that? Shall we do this?” He was resigning from boards and I was helping him write his letters. I mean, yeah, it was really something.

Steve: Right. Well, that’s great that he did. I don’t mean to imply that you weren’t. You had told me before that in your household he was kind of the primary day-to-day finance person. Usually there’s one person that’s doing it, it’s not always the man. But it is great. And actually there’s … I’ll point to this in the transcript, but there was an article that I was reading from another blogger I follow, it’s called DoughRoller. Anyway, he talks about having this blue binder that is what Alan did for you, which is, where is everything, what are all the passwords, where are all the insurance, Will documents, investments, and kind of guidelines for, “Hey, here’s how we’ve gotten where we are today and here’s how to maintain it or who to turn to for help.” So it’s cool.

Michela: Absolutely. And I have binders. They’re blue, and black, and red, and green. And each of those have their own legend because one is dedicated to all the appliances, one’s dedicated to all the building products. I mean it’s amazing. There really isn’t anything in there; in the house or in our financial portfolio that isn’t chronicled right down to the gnat’s eyebrow.

Steve: Well, that’s awesome.

Michela: It is. It takes them way a lot of the stress that others have when this happens.

Steve: Nice. Well that’s good. I mean so much easier to have that ready and not have to be stressed when you’ve got so many other things … are stressed about that … when you’ve got so many other things happening in your life. So would love to kind of talk a little bit more about kind of how your perspective has changed. I know that, so this happened, you decided, you’re the CEO of Dwell, right? So big, influential design magazine, and organization, and kind of media company, but then you decided to leave. And you’re kind of really looking at your life. I’d love to kind of get your take on how what has happened has changed your outlook on life.

Michela: Well, I can tell you that I just kept putting one foot in front of the other during the time when Alan and my dad specifically who were sick at the same time and passed within 14 days of each other. And really always taking my role as a CEO of Dwell very seriously. And there were always moving parts, right? We had seven different platforms, but the most significant of which was building the digital platform and fundraising in order to grow the company. And so I didn’t take any time off really during that time. I would work from home in the morning and then I would go in for team meetings and then go back. But I didn’t stop and really think about what I should be doing at that whole time. I just kept moving because that seemed to be the way to keep my sanity and to fulfill my responsibilities. And that’s truly how I looked at it.
But I had planned a vacation for Taylor and me to Hawaii for the first two weeks of January and it was about five days into that trip when I thought I need to change the rest. I really need to change the rest. And the truth of matter was I had never planned to stay 15 years. And the owner and founder, who is now the owner, founder, and CEO, and completely capable of running the company, this was her idea in the first place, was really ready and wanted to grab the reigns and it could not have gone better. It really couldn’t have gone better because yeah, I think everybody in those scenarios wants to do the best thing for the other person and for the business involved and also do the right thing at that moment. And that most definitely was the right thing for me. And thankfully it was also the right thing for her.
And it was Martin Luther King weekend and I could have skipped around the kitchen. I just felt like, “Wow, okay, now I’ve really erased the chalkboard and I am truly creating a brand-new life.” And started to think about, “So what do I want that to be, as it regards retirement.” Which Alan and I filled out a Merrill Lynch questionnaire with a financial counselor in 1989 when we got married and they bound it, this beautiful blue leather book with the embossed Gold Alan and Michela Abrams, and it had me retiring at 52 and Alan retiring at 64, and I just look back on it, I still have that book and think about what were we thinking really. We were thinking about that we wanted to buy more property and more … Anyway, so the whole idea of retirement just is really an evolving notion. I would posit in everyone’s life. What you think it is 30 years ago is different than 10 years ago, is different than today, and I know it’s going to be different than three years from now.

Steve: Yeah. I mean, this company started because I was trying to help my mom figure out kind of the financial side of retirement in her early 60s. And I remember talking to her when she would turn 70 and she was like, “Okay, I’m really thinking hard about the next 10 years of my life. What am I going to do? How I’m going to spend my time?” And today people have these long and hopefully extending lifespans, if they can avoid getting sick, and they’re very capable and have lots of human capital. So it’s like, “What are you gonna do with your time? How are you going to apply yourself? What will you find most rewarding?” And for many folks, they do have some space to think about it, which is interesting. You’ve been so heads down for 20, 30 years, right? 40 years. And you’re like, “I got to make money, pay for my kid’s college education, buy a house.” Right?

Michela: Right and be fulfilled and continue to learn and grow my breadth and depth of knowledge. And so all that goes on, so you don’t think about, “Well, does retirement means stopping that? Does retirement mean putting pause or narrowing it?” One of the most important influences in my life was a gentleman by the name of Frank Stanton, who with William Paley, built CBS and I was beyond fortunate to have been introduced to him in the early 90s when I was at McGraw Hill. And a very important woman to have the McGraw Hill Company, Liz, said to me, “Listen, I don’t think you pick your rabbi’s very well.” I’m like, “Okay.” She tells me, “Let me introduce you to somebody. Meet me at the Harvard Club tomorrow at 5 O’clock.” And I said, “All right.” And I truly would do whatever she said because her name’s, Elizabeth Allison, just one of the brightest women I had ever met. Her husband Graham Allison ran the Kennedy School for Government at Harvard and an incredible couple, also a complete modern design fanatic.
Now that’s … think about it, 15 years before I would go to Dwell. And so I go to the Harvard Club. And she said, “Michela, I’d like you to meet Dr Frank Stanton.” Now I’m sure I should have known exactly who it was, but she hadn’t given me any preamble. And so here we were and we’re having this amazing dinner. And so I go back to the hotel in New York and I called my parents and they happen to be having dinner with a couple who retired from CBS. I said, “Yeah, I just had this amazing dinner with Dr Frank Stanton.” While the screams on the other end of the phone, like, “You had dinner with Dr Stanton. I mean, Michela, do you really understand that he commissioned the CBS Eye. He commissioned the architecture of black rock in New York.”
I thought, “Wow. No, I didn’t know all that and I can’t believe it.” Anyway, he went on to be a really critical part of my career in what he would say about the way I should view things and look at things by asking me a lot of questions. He was a modern architecture fanatic. Old enough, of course, to have lived through the bow house, had one of the largest serenade collections of furniture.
And so his most important advice right before he passed was he said, “Do me a favor, don’t ever retire.” I said, “But what do you mean by that, Frank?” And he said, “I mean, I’m the one who instituted mandatory retirement at CBS to be 65, so I had to do it. But I made damn sure that I was on the museum board and I helped other people because you need to keep your brain active, and alive, and always continue to learn. Push yourself, stretch yourself, continue to take risks. Don’t think of this … whatever the golden years are to you. That’s not the time to start being really safe.” Even though financial advisors say, “Well, we’re moving you from the high risk to the lower risk part of your portfolio.” He said, “They can do that, but don’t do that with your choices in life.”

Steve: That’s great advice. Yeah. I think more and more, personally about the idea of sabbaticals and mini retirements and this whole idea of like, “Hey, there’s this one linear path through life and hit these milestones and then everything changes.” I don’t think is correct. And it’s going to be forced to changes is largely around kind of longevity, and also just the need for income and money, and there’s this uncertainty in life, and also the need for engagement, and giving back, and doing kind of finding things that you really love to do, if you’re not already doing it. Most people are doing what they love to do, but I don’t know if everybody is. Well, yeah. So really quick before I look forward a little bit more, just as you look back from kind of now till for the first part of your life, would you make any other decisions very differently given what you know now?

Michela: I don’t think so. I don’t think so. Believe it or not … well, part of it is just because my personal philosophy is that life unfolds exactly the way it’s supposed to. And another dear friend of mine who I consider a great friend and advisor always says, “Float down the river, just float down the river. Don’t think you’re controlling it. Don’t try and slow it down. Don’t try and speed it up. Don’t try and predict when the rapids are going to happen, just float down the river and abundance will be all around you.” And I wasn’t advised that long ago and I keep thinking about that whole metaphor of floating down the river and I do. So no, I don’t … yeah, I think it’s all worked out exactly the way it’s supposed to other than what would I change? Yeah, not losing my family. If I could please just pull them back into the picture, it would be just the best.

Steve: Right. Yeah, around your float down the river thought, that was really something about parenting, where essentially with parenting there’s some research shows that it does not matter what you do as a parent, your kids are going to end up how they are going to end up.

Michela: Wow. Okay, well I’ll take some pressure off myself on that one then.

Steve: Seriously. It’s like we’re all beating ourselves up. I got to be a better parent. I got to do all this stuff right. And at the end like that’s just us fooling ourselves that we have a big influence on how our work is going to end up.

Michela: Here’s the influence I do think is very real and new parents ask me this all the time, “So what would you do differently?” And I can honestly tell you with regard to parenting, I would have made it harder on Taylor, but I think many parents, a sweeping generalization I suppose, boomer parents specifically, in general, have made it a lot easier than it was ever on us, right? Because we just want it to be better and more fun and more fulfilling. And in so doing, you kind of start taking resilience out of that person. They’ll learn it. So to your point, they’re going to be who they’re are going to be. But I think if I’d made it a little harder on Taylor, in other words, kind of done it Alan’s way, she’d say, “Michela, you’re making things too easy.” I think the lesson she’s learning now, she might have learned a few years earlier.

Steve: Right. Yeah, in some ways. I think every generation … I mean, we grew up the same way, right? And you would make jokes about, “Oh yeah, when I was a kid I had to walk five miles to school one way and 10 miles back the other way into the wind.” Right? And so every generation always thinks that … I think they had it harder. I think we all had it harder, but in different ways. I look at kids today and, yeah, they have a lot of things going for them. They have a million opportunities, but they also have a lot more pressure. There’s so much that they’re expected to do. Anything about your kids … I always feel like I always have FOMO for my kids. Like are they doing enough stuff? Are they taking full advantage of every opportunity that’s available to them? Right? Which is crazy because when I grew up I would spend so much time and I would watch soap operas sometimes.
I always liked doing all this stuff. That was insane. For my kids today, I hope they don’t listen to this. I would be so [censored] if they were doing it. But it created a different environment for me. Anyway, so the children today, they’re comparing themselves to everyone around the world. They’re like, “Oh, why am I not this Instagram superstar? I don’t have these great shoes or this or that.” Right? Or, “Why can’t I run the 100 dash or whatever?” So it’s a kind of a pressure that they face, but, yeah, parenting … actually, let me retract my earlier statement a little bit. I do think that as parents you can create an environment for your kids. It’s like you can create the aquarium that they live in and then they are going to do what they’re going to do inside of that.

Michela: Right, right. Absolutely. Absolutely.

Steve: Okay, cool. All right, so here you are outside of what happened to your family, which is huge, but have had a pretty amazing life, right? You’re are living in northern California, you’ve got a certain amount of financial independence, you’re well organized and not freaking out about that and have now the perspective to look forward. And now that you’re here and you are thinking … how do you approach thinking about how to spend your time now?

Michela: So I talked about kind of key to vibrancy meets Frank Stanton’s advice is continuing to learn and I thought, “Well, there’s no better way to do that than start my own company and to take everything I’ve learned and apply it with clear focus.” I just didn’t want to be a consultant to consultant and there was that opportunity. I thought, “Well, I can just do that and dabble and stay in touch with my network and when they need me, they’ll call me and I can do it that way, or I can really organize around principles that I learned and fine-tuned and believed in.” So I decided that I still really wanted to spend a lot of my time on my professional craft, if you will, and so I started Moca Plus, which is not the Museum of Contemporary Art, it’s Michela O’Connor Abrams plus, a sign was indicative that I will build the team as required for the client.
And so I’ve built an entire framework for this company around culture by design. In other words, understanding that when you want to achieve something as a company, if you don’t have a culture to support those goals, it doesn’t happen. You won’t be successful. And so I have been able, thankfully, to parlay many of the clients and companies with whom I had been doing business for the last many years to being my clients now at Moca Plus and helping advise them on those cultural issues that are really all part and parcel of growing a stronger customer focus brand, kind of putting design thinking at the core of what they do and learning a great deal at the same time; spending more time with massive change institute and all the principles of Bruce Mau and continuing to stretch my brain and learn.
So I’m spending probably a lot more time than I thought I would doing this. But it’s okay because I’m having an enormous amount of fun and because it’s my own business. If I will need to spend a day working on client work and in my sweats that I went on my hike with then I do that. If I want to do the business from Hawaii, and so I have a client on the south shore of Hawaiian, that helps, then I do it there or if I want us to go to New York for a month and work out of there. I love the flexibility, I adore traveling and I’ve been able to thread all those together really elegantly and have a great time doing it.

Steve: That’s pretty cool that you’re taking advantage of the opportunities to live in different places. That’s something we’ve talked about doing here and I think a lot of people fantasize about is having the flexibility to say, “Yeah, let’s go to New York and work out of New York.” Or, “Let’s go to Hawaii.” Or, “Let’s go to Europe and I’ll just work there because we can.” And for certain kinds of work you can work anywhere. You can work on your laptop, and so you can be engaged with work, make money, but also kind of having a completely different experience.

Michela: Exactly. Well, I mean right now I have a client in Boston, New York, Chicago, Seattle, and Los Angeles. None right here.

Steve: Plus Hawaiian, Right?

Michela: Exactly. So I’m a on a plane, or on the phone, or doing zoom conferences the whole time, but that means that by and large I can do that from wherever I am, unless it’s an in-person board meeting or something like that. But that too, you really intentionally weave into what you need to accomplish. So it feels so freeing to do what you love the way you want it, how you want it, and with whom you’d like to do it. So that’s been probably my favorite part.

Steve: It’s awesome to hear that you’re doing that. I saw my cousin who’s 30 now. He’s sort of a digital nomad. He’s been working in Germany, he’s been working in Israel, now he’s working in New York City and he’s able to do those because he hasn’t gotten married and doesn’t have kids yet, but it’s cool. And you did you hear about kind of younger people doing this right? Working on wherever. And so I bet we’ll see more and more people after post child or empty nesters taking advantage of this, right? Do you use Airbnb and stuff like that?

Michela: Oh yeah. Airbnb, VRBO. Love that absolutely. I’ve come to know a couple of the hosts and that’s been a lot of fun. I really enjoy that more than hotels. Yeah, it’s been great. I thought of something I wanted to bring up because you really triggered this when we’re talking about people who were taking sabbaticals, and taking breaks, and thinking about the New retirement, and the whole premise of your business, I think I wonder if we’re going to get to a place where retirement’s actually just about these breaks in chapters, right? That when you’re 25, you’re taking retirement and that’s some specified break, different than a sabbatical because a sabbatical is like just taking a break from what you’re already doing. But a retirement chapter might be really-

Steve: Something else.

Michela: Something else. Breaking it to completely change direction by some degree of what you want to do and how you want to do it. And I think also what is so true about millennials is that they wouldn’t dream of waiting until some period of time at which they had spent enough time at the company in order to leave and retire. It’d be like, “Why wouldn’t you just do what you love now?” Right. So that whole notion with seniors, right? About the gold watch, which certainly wasn’t true for boomers and now for sure isn’t true for Gen X and millennials, I think is about seizing the opportunity when you have it. If you’re going to the Galapagos, you probably don’t want to be 80.

Steve: Right. Yeah. I think that it is a generational thing, right? The millennials and probably Gen Z see this. They’re learning and they’re like, “Well, I don’t want to sit here and work straight through for 30, 40 years. That sounds ridiculous. I want to do what I want to do, where I want to do it, what I want to do it.” And I think giving kind of Gen X and the boomers permission to say, “Hey, you know what? It’s doable. Just do it.” Right? You told me about this when to jump guy. I’d love to kind of … did that and inspire your thinking about-

Michela: Very much.

Steve: .. what you did?

Michela: Meeting Mike while I was at Dwell and he just came to me because he was referred by a friend and said, “Hey, I’m … what I’m doing and I got this deal with Huffington post and I’d love your help negotiating the contract. And here’s what I want to build.” I’m like, “Oh my God, that is like too good for words. Who doesn’t need that?” That’s not a bad generation. That’s totally about a mindset, about just understanding that you just gotta listen to the cues, however old you are about when to jump, which is so fun because he’s so smart.
And so I don’t know … just has great vision. And I connected with him yesterday and he said, “You are not going to believe this. I decided just to enroll in Stanford MBA course. So now I’m back in school and I said, “Well, you knew when to jump back into that.” So it was incredibly freeing to think that if this is a whole company in a movement then I’ve really got to really open the gates to what it means to … even in creating my own company, it doesn’t have to be in any structure that I knew of before.

Steve: Right. And just so our listeners understand, I’ve looked at his site a little bit. It’s whentojump.com. I mean, he’s a person who said, “Okay, I want to take a nontraditional …” He had a kind of a traditional job, right? He was a banker or something or consultant and then he said, “Forget it, I want to be a professional squash player. I want to go do this.” And how he thought about doing that and also working up the courage to just take a totally different path.

Michela: Right. And couch surf too. I’ve forgotten it’s in his book, When to Jump. I don’t … how many countries. It was something like 73. I mean, it was amazing and it was really in that journey that he went, wait a minute, I wonder if everybody else knows that they can do this and that kind of what is what gave rise to When to Jump.

Steve: Yeah. I like that chapter analogy that you had. So I think I told you about the whole fire community. This is the financial independence retirement early. So these are folks that are trying to get to be financially independent as early as possible and then do whatever the heck they want, but it’s still kind of that traditional path of like, “Okay, I’m going to work really hard, save a lot of money until I am done and then I’ll do whatever I want.” I like this idea of, “Hey, you know what? I’m going to work, have enough money, enough flexibilities so that I can take time in my life to do other things, recharge and then come back and maybe I’ll end up working a little bit longer. My work will be a different done in a different way. Maybe it’s the same total amount of time, but it’s just spread out over a longer period of time because there’s one year breaks every five years, something like that or whatever the number is, however it looks.” So maybe that’s where we’ll end up.

Michela: Maybe.

Steve: If we can deal with the uncertainty and make sure that we can all finance it.

Michela: Yeah, that’s always the key. Right? And then you just have to make the sacrifices necessary to do what it is you want.

Steve: Yup. Totally. So you’re off doing Moca Plus. Sounds like it’s going great.

Michela: It is.

Steve: Have you run into any ageism or any issues like that? So you’re deeper in your career right now, right?

Michela: Right. Oh absolutely.

Steve: Any of that stuff happen?

Michela: No, and I’m surprised because I was really prepared for it and not in a defensive way where I thought, “Okay, I better guard the loins for the pushback and the, ‘Oh gee, aren’t you finished yet?'” I haven’t gotten any of that. In fact, I think the thing that I realized transcends age is it’s really … I suppose this isn’t some blind … it is a blinding glimpse of the obvious. It’s not some huge pearl of wisdom nobody’s ever heard, but it is all your attitude. It’s all attitude and you’ve heard that and probably know people that are 50 and they act like they’re 80 and people who are 80 act like they’re 40.
And so I think it’s all attitude and I think because I am really gotten to a place where in creating this new phase in my life, it just feels so good that I think that’s what you telegraph; that you’re just so happy, and so energized, and so certain about what it is that you have to offer and what partnerships can be like that the responses has just been, “Well, of course you are.” And, “This is incredible.” And, “Do you wish you’d done this sooner?” That’s the most common question I get is, “This is going so well. Don’t you kind of wish you’d done this sooner? I’m, it’s your own thing.” And it goes back to, if I wished I’d done it sooner, so what? Right. It’s every building block, every year of your life that you are living and experiencing life is leading to what you do now. So I wouldn’t be doing it perhaps this way if I started it four years before I did.

Steve: So you don’t wish you had done it sooner or you’re just like, “It is what it is.”

Michela: It is what it is and it’s going to be even better.

Steve: One thing that we do hear from people who “retire” or leave their main career is they have a lot of anxiety about it. We’ll have enough money and am I ready and worry we’re not leading up to it. And then as soon as they’re there, they’re like, “This is great. I wish I’d done this sooner.” And I think that’s true for any big milestone. For many people, they’re much more … the anxiety about what is going to happen, the anticipation of like, “I’m going to give a big speech.” Or, “I got to do this big performance.” You’re freaking out about it, and then as soon as you do it, it’s fine and hopefully it went well.

Michela: Yeah, absolutely. I think that if you go into whatever it is, the next chapter of phase, taking a break, you can’t go into it wondering if your relevance is going to be tested because if you are not secure about your own relevance, then you need to work on that first and not look to whatever that next chapter is to make who you are and where you are in your life relevant. You’ve got to be really clear on that first, because if you are, then you can pretty much create whatever you want to do. Could I go be a brain surgeon right now? No, of course not, but there are hundreds of other things that I could do if I chose to and put my mind to it.

Steve: Right. Yeah. You have to have that core belief that you can continue to invent the future. That’s what you’ve been doing in your career and as you look forward, it’s how do you continue to contribute at the same rate or in a different way or however it is. So as you do this, are you now dealing with lots of people of all different ages for your clients?

Michela: Absolutely. I have clients who the main point person is 30 and I have clients who the main point person is 70. I have a client who has an all-male board over 60. I have a client who every one minus the CEOs is in their 20s. And the dynamics are different because of perspectives, but the work that you do and the focus that you have on whatever you’ve decided you’re doing together and what the goal is, is still what it is, right? You’re still following a discipline and a path in order to get to the agreed upon goal.

Steve: And you haven’t run into any issues with dealing with all these different kinds of people and different ages and stuff like that.

Michela: I mean, fortunately I haven’t. I think I did have one client who said about my memos back to them, men, suggested memos to the board that they were the CEO and could I be less CEO like. That they didn’t want the board thinking that they shouldn’t be the CEO and I should. I’m like “Whoops, okay. Kind of hard to get smaller than then your sell for, less capable or water something down. But that led to its own discussion and experience of what we should do next together.

Steve: Right. That’s cool. Well, I actually love to dive into this side of it. So you’ve been this kind of leading female CEO, right? So any big takeaways from your career? I mean there aren’t that many female CEOs. It’s a growing number, but any lessons?

Michela: Well, I haven’t been asked for many years to speak at different events on the glass ceiling and I always decline unless I can talk them into a different take because I personally did not experience that in terms of men dominating something that I wasn’t able to be a part of or be compensated equally for. And I realized I was very fortunate because I am not saying that it doesn’t exist, it’s just that … and I think the best example for me was five years I spent at McGraw Hill. When I went there and I was coming out of IDG and Ziff Davis, very progressive technology media companies that … are you crazy. Not only are they not number one or two, but they’re like number three and it is the oldest old boy network and Michela really, I mean, come on.
And I didn’t experience that at all. Now first, them saying that just made me want to do it even more because that’s my nature. But what I found was an unbelievably supportive organization that certainly had some ossified systems and it had the Mahogany rooms and dining rooms with the waitresses and the pencils, all those things that were part of a different generation, let’s say. But when I worked hard and this is all in my 30s, I knew exactly that I would be rewarded for it and I was rewarded in ways I never imagined and recognized in a company that’s huge. And my business unit was not in the top 10 of the revenue in the $2 billion corporation. And yet they, through my boss and his boss and his boss’s boss, really completely a recognized my work and made sure that I had the opportunity to learn everything that I could learn at that company. And so it was, it was amazing.
I will say that again, this is just personal story, and for me, there were two women in my career who made life much harder than it needed to be. And I, through that experience, vowed that it would only make me want to be a better mentor to other women, however old they were because I don’t think that we have done enough for each other. I don’t think women, yet, lift each other up enough. There are all kinds of theories behind this, like because it’s the scarcity of the boardroom and the scarcity of the corner office.
I don’t happen to believe or subscribe to that. I believe it’s not about scarcity. It’s been about choice. There are more women who then step into CEO roles, especially in the fortune 500 and choose to do other things to exit, to do myriad other things, from raising their families to traveling, they did it. They don’t feel like they need to spend the rest of their lives doing it. But I don’t know that we, as women in general, have done enough for each other. And so I think that’s what I usually say in these speeches. Let’s focus on how we do it rather than to figure out what men have done to hurt the whole cause. Let’s talk about what could we do for each other.

Steve: Right. Are you involved in any groups that help facilitate female founders or female CEOs?

Michela: I am. There are two private groups and then I do mentor one CEO and founder of a company called Next Play, which is a mobile mentoring platform. She’s unbelievably bright and way beyond her years. And so we spent a lot of time talking about this and the whole reason she started the company when she comes out of college and goes to a big Silicon Valley firm and says, “Wow, where are my mentors, and who is going to help me out, and why is it so hard to get another man or woman?” But especially she wanted to find other successful women and nobody had the time. So that’s why she did this and she’s incredibly wise, so I very much enjoy mentoring her.

Steve: No, it’s cool. It’s great to give back. I do want to talk a little bit about kind of other influencers. I know that we both know Chip Conley, right? He just published his book, Wisdom at work, the making of a modern elder, have you read that book?

Michela: I have.

Steve: Good for you.

Michela: I have. It just came out and I’ve read it.

Steve: Nice. What do you think?

Michela: I love it. I mean, when Chip first told me about the book he was writing over a year ago, I thought, “Oh my God, of course he is because he’s always been a pioneer and whatever he’s done.” And I was especially pleased that he would do this because again, it starts framing the discussion differently about what it means to be more experienced, or seasoned, or older and relevant and where all of the different players generationally have to contribute to each other. And so I just, I really love the fact that he’s just dealing with a construct that instead of talking about ages, he’s really talking about mindsets and still understanding that there are mindsets generationally, right? Some people transcend those better than others, but how do we do that at work?
How do we not assume that the person who’s only been out of college three or four years just hasn’t “cut their teeth yet” and they just don’t know and they haven’t gotten far enough on the learning curve? That would be kind of painting everybody with the two young brush just as bad as saying, “Well, gosh, look at their resume, they’ve got 35 years. So are they really gonna have an open mind? Are they really going to be able to be fresh enough? Are they going to have new ideas? I mean, why aren’t they tired?” Yeah. And when you read the book, it just changes the discussion and the vernacular. It’s so, so good.

Steve: All right, well I’m looking forward to reading it and hopefully he’s going to come on the podcast. So we’ll-

Michela: I hope so.

Steve: We’ll talk about it. But he’s a pretty inspirational guy and has always done some innovative stuff. Have you been down to … I think he’s got a retreat, right? In Baja?

Michela: Yes.

Steve: Have you been down there?

Michela: I have not and it’s an invitation only, so I’ve just raised my hand probably along with thousands of other people who love and admire him. I can’t wait to go.

Steve: Yeah, it looks pretty cool. I saw a video that he put together. Yeah, I think one thing that’s interesting is, to me, having talked to more folks that are financially independent or they have the space in their life is that … one thing that drops away is you feel very confident that whatever they’re spending their time on, they’re being completely transparent with you about and kind of how they’re aligning their time and activities is all around what they want to do a for these goals that are clear to them versus when out there in the beginning of your career and you have to make money or you have like, “I want to make money or I want to get to a certain point in the corporation or whatever it is.” That’s all a political stuff that falls away for these other folks. And I do think that’s one thing you get when people get a little bit farther along in their careers, either they’ve got the financial wherewithal to kind of make people independent.
And I think the other dynamic is they realize, “Hey.” And they are much more cognizant that time is their scarce resource and I don’t really want us to go around here, “I had this vision for something I want to get done, this is how to go about it, and if I can find people that are aligned that’ll be great and if they’re not aligned then don’t waste my time.” I see that. And I think that will be a good thing for the economy. People over 50 I think are the biggest startup founders now, are the largest group of startup founders. So they are out there creating companies and very often with these slightly different or are different drivers at the end when they approach it. Are you seeing that with people you know?

Michela: I am. In fact, I’m the acting CEO right now have a fabulous company created by two of the founders, anyway out of Harvard GSD and MIT. They’re masters in MIT and it’s called Ark Bizarre. It’s just it will, I think, completely changed the way that architects, and designers, and consumers work together. And it’s a platform they’ve been building over the last four years and the people that have invested in this company are in every age bracket you can imagine because they admire not only the path that this platform’s taking into AI, but into the excitement about what it does for design globally, what it does for architects in the profession globally, and truly when people on the board who have been in business for 40 years and people on the board who have invested and been out of college for seven years.
So I love it because you can absolutely tell in all the interactions, be they in person or through email, that there’s really no kind of discussion about how much you know, or how long you’ve done this, or you’ve done this too long. I mean, it’s just the galvanizing principle. It’s why we all think that this is a game changer and in such a bigger way. And that’s what I see more often. It’s come up with really good ideas, whether that’s a disrupter in a major way like this is, or just something that, it changes the way we do things and in a, perhaps more fun way in a market, people come to it through their interests. And interests in what I’ll call the psychographic parts of the way we think and work really transcends demographics at the end of the day.
I mean, if you think about it for the first time in the history of the world, we have five consuming generations: seniors, boomers, Gen X, millennials and Gen Z. And so the way that we start attracting people into communities of interest is on attitudes and behaviors. It’s not on age. And I’d think that that is starting to make a much bigger difference in the way that the largest companies market to people.

Steve: Yeah. That makes sense. Have you seen any great tools, or communities, or platforms for folks to kind of research and find other interesting areas they’d like to spend their time on?

Michela: That’s a good question. I’m thinking of … all of a sudden, I can’t think of the name of the site. Oh my gosh. And He’d kill me. I’m Jeff Tidwell just started-

Steve: Next for me.

Michela: Yes. So there are a lot of interesting people who he’s interviewing and are talking about their business and kind of how they’ve joined somewhere in their 50s and reinventing it. And ideas that are about different kinds of ways to travel different. So I like that. I can’t think of any just one that I would look to that has some galvanizing principle about reigniting interesting things that you may not have done before. But I think a lot of that, for me anyway, comes from my social circles and things that other people do and I’ll say, “Oh, I never thought of doing that.” I mean really living in Florence, taking a three-week culinary course as well as at it’s done through the lens of different artists in the … I was like, “Wait a minute. I’ve never heard of that and I want to do it.” So it’s things like that. Hard to corral all of those things.

Steve: Right. Well, we’d talked about this a little bit offline, but the idea of a facilitating communities and potentially live events, getting people together just to kind of talk about opportunities, and ideas, and the whole salon idea, and finding inspiration from other people. And we met originally at this Moran Internet entrepreneurs meet up, which is a bunch of folks that are … people that had worked on the Internet that live up here in Marin, half an hour north from San Francisco and it’s just interesting to get together and see who you meet and what they’re up to do. And it’s amazing the ideas that folks are working on.

Michela: Yeah, I mean, I think that whether it’s a cocktail party, or a salon, or a large gathering, a meetup, a festival, live events are the darling right now of the investment world. They are, prevalent more plentiful than magazines or television shows even at their peak. Because I think we crave, at the end of the day because of all the technology, to really still just get together with each other and it is a different experience, different dynamics, lots of things happen there.
And so sometime … and my neighbor says, “Have you turned your home into an event space because you keep hosting people. I mean I watched the most interesting people, Michela, walk through your door. I mean sometimes it’s just a group of people that all look like they’re right out of college and some people look like they’re all your parents’ friends.” And I do. I love it. I really, really love. And that’s why I offered to have my house be the host for the Marine Internet entrepreneurs and it was really great and I can’t wait to do it again. In fact, Chip and promised that he would do something this fall and do that. So maybe what he does is he has a podcast right here and then we go a mile over to my house and we have another entrepreneur forum.

Steve: Sounds good. We should definitely do that. Yeah, I totally agree with you on a lot of that stuff. So much of our digital experience, it’s curated and filtered by our social networks and the bubbles we live in and whatnot. And there’s actually not that much serendipity that happens, right? Versus when you’re out there in the wild, you’re traveling, or you’re going to some group or you know one person or nobody, and there’s 150 other people in the room, you don’t know who you’re going to bump into. And that’s good because you have to find those new connections and be inspired by other people and engage with that wider community. That’s cool. Well, hopefully we’ll spend some time working on some of the stuff as we look forward. All right. Well, we’ve covered a ton of stuff here. Anything else that you want to cover, or questions back, or topics?

Michela: No, actually I was just going to add to the whole live event piece when we were talking about this and how do you take New retirement to the live experience and really share it in a way that you have these local or regional champions in places. And I talked to you about the model that I don’t … God, it’s got to be 25 years ago, that first company first came on the scene and started having company of friends and Ted has done that with TEDx. And I think it’s such a great discussion and so important that we start to reframe because that’s already happening, but that what you’ve done in really pulling all the different facets of what we thought of his retirement into the future and what that means and kind of to unleash that into the live event arena I think will be really exciting. So I wanted to make sure that everybody would encourage you to do that.

Steve: Yeah. Well, I’m hearing you and we’re starting to do some stuff. We did a virtual one, like an ask me anything and it was kind of interesting to get people there, kind of a webinar experience, from all over the place, hear what they had to say. I want to make a more live version of that, throw a more kind of a full video feed back and forth with the group and see how that goes. But yeah, and then also do like the live event that we talked about and maybe we’ll do it here in Moran and kind of get people together. I’m going to participate in Jeff Tidwell’s Next for me. He has a meetup coming up here in mid-October. So we’ll be there and we’ll see how that goes. That’s going to be in a coworking space that’s kind of focused on boomers. So it’ll be interesting to see how that goes.

Michela: Wonderful.

Steve: All right, so thanks Michela for being on our show. Thanks Davorin Robison for being our sound engineer. Anyone listening, thanks for listening. Hopefully you found this useful. Our goal at New retirement is to help anyone plan and manage their retirement so they can make the most of their money on time. And if you’ve made it this far, I encourage you to check out Moca Plus. If you need help with design or culture and design thinking, talk to Michela. And if you’re in retirement planning and kind of thinking about your future and getting more confident about that, checkout New retirement in our planning tool now. We have tools and personal support available. And you can also find us on Facebook and we have a private Facebook group or on Twitter @newretirement. Okay. Thank you very much.

Michela: Thank you so much.

Steve: Appreciate it.

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