For most people, work feels like a treadmill where we have to sacrifice our personal lives and even our soul. Diana Wu David, author of Future Proof, believes that having the career that we want shouldn’t require us to lose ourselves. We all deserve a sustainable work environment, and now, we can have it. Diana’s book is about reinventing work in the age of acceleration.

Before she wrote the book, Diana was a strategist and an innovator and an entrepreneur. She was the founder of Sirona Capital and Sirona Labs. Her work was focused on transforming how executives work and she helped them prepare their companies to be more entrepreneurial and resilient and successful in this era of constant change.

In this episode, Diana’s going to share real life stories that will help you become more innovative in your career and your life so you can stay resilient and relevant and enjoy your life in an ever-changing global landscape.

Diana Wu David: I got a call when I was at the Financial Times, sitting at my desk. Really, I know that she had been going through some hard times, but she was always the one that had a lot of hutzpah and really was like, “Come on Diana. Get off your ass and do something, don’t wallow in it.”

Her husband called me and said that she had put a bag over her head and actually killed herself. It was so shocking and so devastating.

Really, it was something I had never spoken about it until I did the TED X talk. It happened a couple of years before, it’s not like that wakeup call that transforms your life. I love to be that proactive or even emotional but truly, it was like that what-matters-moment where I had spent the day before thinking, “My god, my kids have to be in music lessons. I mean, seems like everybody’s – instrument and they are not playing an instrument and maybe I should get on that and I don’t have time for that…” What everybody goes through.

If you don’t have kids then it’s like your own aspirations that are left unfulfilled.

I just thought, “Wow, this really doesn’t matter.” What if I’m pushing these kids to be the best that they can be for all the external markers…They’re not resilient enough to cope. You start to see that a lot around the world, where people are just supper ambitious and in pursuit of these external successes without the ability to bounce back. That was fundamentally the sort of a touchstone for me when things get crazy and was also a time when I was working eighty hours a week.

I was really obsessed about the security of my corporate job and security financially. I was prestigious and was traveling the world. I spent so much time in that, I was never investing time in making myself more resilient.

If I lost my job, I would have been a totally at a loss.

I spent a lot of time thinking about both my kids and local school kids and stuff, but I was never making myself Future Proof.

“I wasn’t investing time in being more adaptable or having a broader skillset or even just being more resilient.”

That’s my very personal story. Then I worked with incredible senior leaders, I set up this independent board training, and these guys were CEOs in major corporations and had started their own companies.

We were teaching them some fundamentals of how to be more effective in their boards or how to transition to those experiences or those obligations or those opportunities.

They would always say, “Diana, can I have a coffee with you? Can we talk about like some next steps?” and I thought, “My god, these people are like 10 times smarter than me, what on earth can I tell them?”

It made me realize that a lot of them were going through a version of this. These guys were looking out at a longer life. They had been incredibly successful.

They were sitting there looking at the next 30 years going, “How could I possibly do anything that will top what I have right now?”

How can I be in the world in a time when longevity means I’m going to have a hundred year life, but I’m not really sure what to do? And organizations haven’t kept up, the world hasn’t kept up with this experience this sort of collision of disruption and longevity that we see in the world.

Future Unfocused

Charlie Hoehn: Can you kind of paint the picture a little bit for why it is such a challenging problem for people?

Diana Wu David: Yeah, I can totally relate to that feedback because I spent a lot of time in the equivalent of the inner city working with secondary school students. These are people who, in a big city of seven million people, will have come into my office and have never been on to the central business district. They’ve never been in a city full of skyscrapers, they have never been up the elevator to the 40th floor and sat in a boardroom talking to somebody who is really different than them.

I spent a lot of time on the future of work with people who I feel really don’t have access. Here we’re talking about people who, frankly, do. One of the things I feel is that it’s so important to capture this group of people and have them still engaged to contribute.

We have so many problems in our society that it would be a shame that people at age 60 were like okay, well, I don’t have a job so I’m going to just binge on Netflix.

Charlie Hoehn: Haven’t a lot of them been sold on that as the dream? Instead of Netflix, maybe some of them think golf or hang out on the beach like retirement. The cease of work.

Diana Wu David: Yeah, I think that that’s the dream, and it’s kind of like a bait and switch from what I’ve seen. First of all, people are not taking time to slow down or enjoy their hobbies.

I think as you have experienced with people—even in my generation, I’m a gen Xer—we learned and went to university and then did our job and then we were promised the nirvana. But the reality is that very few people can do that for 30 years. Most people will spend maybe six months, maybe a year, reconnecting with the things that they like to do when they didn’t have to always be running around.

“Then they get bored.”

The reality is that they probably will live a lot longer. If they retire at 60, 30 years for themselves, they’ll be healthy. So they can work and a lot of them need to either because there’s just this sense of fear of that length of time.

You can say, great, I’m 60, I worked like 40 years, but is that going to pay for the next 30?

I think that’s something that at all levels, there’s a pride from work. There’s a financial necessity, There’s a pride, there’s an intellectual stimulation. I think that people really want to continue working in some capacity—maybe not 80 hours a week and flying all around, but they want to contribute.

We even did a survey when we set up the program for financial times for board directors, and we said, why do you do this? Is it intellectual stimulation, is it the money, what is it?

They said, we just feel like we’ve developed all this knowledge and we really want to give back. We want to have it be useful for the businesses or organizations or causes we care about, as in the next several decades.

What’s Coming?

Charlie Hoehn: Can we get into this bit of the specifics of the future of work? Is this all stuff that we’ve heard of like the robots are coming and AI and whatnot? Is there more to it?

Diana Wu David: I think that what I wanted to do in terms of the first part of the book. You hear a lot of the threats of automation, headlines about how jobs will be lost. I have spent time working at a sort of governmental policy level on those issues, and I think that they’re important at that sort of policy level. An organizational level.

I think actually, a policy level is the most awareness because people are thinking about transition to things like basic income and those kind of things.

I think if you read the press then you’ve seen the headlines before. I wanted to make it salient to people who were kind of at the leadership level.

“I wanted to make it personal.”

Companies are just waking up. We’ve had the millennial conversation, and now, most organizations have not really thought about that. They haven’t thought about on a sort of company level, whether or not they would raise their retirement age.

They might not have thought about, “I can continue to have some of that talent,” you know? They’re really struggling with it, and people who are in senior positions are often thinking about the future of work from how can I protect my team, how can I protect my organization, how can I contribute to the community I’m in. Could I give better access to train or educate kids or how can I educate my own kids? These are the last people to think, “What does the future of work mean to me?”

It does mean that it’s not robots coming to automate the factory. That’s the biggest impact you’ll see and it makes the best headlines, but a lot of people are not thinking about, how will disruption change the way that I’m working or contributing. They’re also not thinking about it from an opportunistic point.

It was a revelation to me that after having like a running original sales team and having to deal with virtual teams, really worked so well for me when I had a portfolio career. Now, everything was on Google docs and Google calendars and we called in. I could be anywhere in the world and it really just worked.

I did set up my own fashion label, which was AI enabled, and I had 15 people working for me and no office.

Opportunities in the Future

Charlie Hoehn: AI enabled fashion label?

Diana Wu David: Well, yes. It would scan you to tell you what your size was and then manufacture clothing specifically based on that. The AI sort of aspect would be learning all the time what it was you liked what it was you didn’t like, what might be better for you, etc.

There was a lot of technology behind it. It was an idea with a huge group of virtual workers coming together. The website done in Ukraine and a freelance PR person to do global PR. Those are the kind of things that I think that entrepreneurs know.

I really work with a lot of entrepreneurs, investment entrepreneurs. They’re like yeah, of course.

“But people who have been in corporate entities have had less exposure.”

There’s less opportunity to realize that if they are going to transition to something which is a little different, there are all these opportunities in the future to not do some of the things that can be automated. To collaborate so that you don’t have to do everything yourself.

I think that regardless of whether you’re going to stay and transition your team or your company to something that’s more Future Proof or you’re going to try and do it yourself, people need to know more about some of the elements that go on. It’s not that robots are coming and we’re all going to be out of work.

It’s much more like, the robots are coming. How can we work with machines to make this better? How can we do more, in addition to just transforming the company at scale or transforming your department.

Investing in You

Charlie Hoehn: Now, people listening to this want to know how to be prepared for the future. How do they invest in themselves?

Diana Wu David: I spend time in the intellectual future of work world, and when I wrote the book, I was hoping to include something that you don’t see in the future of work conversation as much, which was the time that it requires to really think about what will make your life successful.

When you’re thinking about the future of work and you’re thinking about the perpetual reinvention that might require—experimenting and trying to put really disparate pieces together of your life and your experience over time. The thing that is the big anchor for me and for others that I spoke to was really the values that you would anchor your life and would be a through line in terms of your personal narrative. The sort of collaboration or the support network that you put in place, because I don’t live in the town that I grew up in and I don’t have a neighborhood where I’ve known the people I do now. I’ve moved quite a bit from my career and for the promise of adventure.

“People don’t have those support networks.”

That is an aspect of the future of work where we all have a job every two years and we have different projects and it is sort of the gig economy as well, where people really need to consciously think about where they’re going to have a network of support, a network of collaborators and what kind of things that they can do.

It’s really promised to be really exciting, but it is also volatile and uncertain. So that is the essence of that part of the book, and I feel like I couldn’t do it justice without really anchoring all of the innovation that I bring to people’s careers with some of the more fundamental aspects that in aid of acceleration often drop to the bottom of the list or we don’t even think about it at all because we’re not taught that in school.

Putting It into Practice

Charlie Hoehn: In making this book, did you make changes to your own life? Did you get more clear on your own values perhaps?

Diana Wu David: I think that it was an opportunity. It was an opportunity to be inspired by the stories of other people who are making different choices. I could see in the people that I interviewed that they had decided to often make hard choices to either spend more time with their families or to pursue something that seemed crazy to most people and so in that sense you know I made changes, I think less maybe to the ideas that I had and more to the execution.

We all say that we want to be healthier, we want to spend more time with our family, but very few of us then spend our time that way. So that was a big change that I had to be constantly reminding myself of.

“In some cases my children would say, “You know mom, you said that…””

One time I was booked to speak about the book. I was so excited writing a book and all of these ideas, and I was invited to speak in Singapore. I was on the phone going:

“Yeah, that would be great!” I could totally see these big internet companies were there, and I got a little carried away and I got off the phone and my son said, “Mom are you going to Singapore on my birthday?” and I was like, “Oh damn!”

The publically putting it out there that I am going to change my life and these are my priorities, that did change—and also it was exactly what I described in the book, as experimenting.

During my corporate career, that was going off to try other things, getting involved in other organizations, joining boards. I was joining the board of a robotics education company because I wanted to know more about how people were getting prepared for the future of work. Working with machines I think is incredibly important but those were experiments that I did and then tried to get feedback to then live my life, That is one of the things that really changed.

It is something I did in my corporate job as a corporate entrepreneur and as a non-corporate entrepreneur. The idea of defining a test and doing it and getting feedback and iterating and taking small bets. I did that much more consciously in my own life, and hopefully I can share with others.

Success with Future Proof

Charlie Hoehn: What are some of your favorite stories or case studies from them particularly in part two, in cultivating the virtues for people to stay engaged and relevant. Do any stories come to mind?

Diana Wu David: Yeah, I think that one of my favorite stories in the book is Brian Tang, who I have known for some time. He started out as a lawyer at a white shoe law firm called Sullivan & Cromwell, and then he went to Silicon Valley during the dot com boom.

At the time that I met him, he was at a bank and heading up and trying to develop their Chinese investment banking joint venture. So the kind of person who you’re like, “Ray you’ve done it all, go golf.”

So he left his job at the bank to go set up Asia Capital Markets Institute because he really felt like conduct was one of the issues during the financial crisis and that he was dealing as a lawyer with regulation. He wanted to form a body whereby he can have more impact by as he put it, sort of leaving the aircraft carrier to herd the ships or to herd the aircraft carriers and really make a difference in that way.

He was like, “I have done the majority of the top IPOs in the last couple of years. So do I just want to keep doing this or do I want to try something else?”

He also set up on the side, he said to himself, “What do I want my kids to be looking at when they look at me? What would be a good role model for my children, and how can I spend more time with them?” So he started Technovation, which was cultivating maker mindsets in kids, including his own son.

That was something that I had the privilege of many years, so it wasn’t just writing the book. Even during the book, his involvement’s changed. He went from doing this thing where everybody thought he was crazy to then adding on this maker fair and everybody said, “You’re like a capital market legal guy. What are you doing starting a maker movement for kids?”

“The interesting thing, over time, is that he plugged through the uncertainty.”

He was doing things like the first rig tech hackathon in Hong Kong. Recently it’s all come together and he was appointed the founding director of the Universities Interdisciplinary Law Innovation, Technology and Entrepreneurship Program. So that to me is such a great story because it’s not like you go off and experiment and reinvent yourself in one moment. It is really this journey of thinking about the things that you’re already fantastic and all of the experience that you have had and then other things that you think are interesting.

A lot of people look out and go, “And then you are taking all of these small bets—does that add up to anything?”

I think that he is always been engaged and has had this fantastic growth and learning, but he is the only person who in my opinion, who could ever have that job and those are the jobs that I think are the jobs of the future. He’s definitely one that it is exactly that.

He was like, “How can I stay engaged? What is important to me? How can I stay relevant? I could do the same job and be paid well and probably do it incredibly well, but how can I be even more ambitious for myself in crafting my life on my terms?”

Maximizing Impact

Charlie Hoehn: I would love for you to tell one more story from the third part of your book which is maximize the impact of your actions. I know the previous story fell a little bit into that category for sure but could you maybe tell another story from this section of the book?

Diana Wu David: I think that the last part of the book is really coming back to the environment that we live in and the deeper values you hold and where those two can intersect. I talk a lot about rebalancing a portfolio and redefining success in those chapters, because it is something that I think that it is not specific to people who are maybe embarking on an on core career.

It is something that everyone will have to be thinking about, because if what the future of work pundits say is true, we will spend more time having careers and transitions and then going onto a new job or project or career. Maximizing the impact is about also maximizing those moments of transition. To really think about not just what do I want to do, but what do I want? Is all the work that I am putting in here giving me the life that I want to look back on?

So that is really redefining. It is living your work in the context of your broader life as opposed to living the life within the context of your work, which is that there are so many more people who are wiser than me but that was what I had done for most of my life and frankly what I think I was taught to do.

“Rebalance the portfolio is really an approach to get there.”

So thinking about auditing doesn’t usually inspire a lot of people, but I talk a lot about an audit of relationships and time spent really reviewing that to see, “Is this what I said I wanted, and am I doing it?” in a nutshell. Most people find that maybe they aren’t.

Tim Ferriss famously looks back at the time that he spends. He’s really good at this, every year and says, “What did I do? What did I spent my time on? Let us look at the calendar.” Then he rigorously prunes it, much better than I could ever do, the things that are not really serving his definition of success or even his day to day sense of fulfillment.

So that is something that I think is really actionable and has been really successful and defines the people who are running around thinking, “Oh well, maybe I’ll do this, that and the other” versus the people who are really intentional about crafting a life where contribution and work is a part of it but really working on some of the other aspects and soft skills—skills that will allow them to be great people in addition to have a great career.

Connect with Diana Wu David

Charlie Hoehn: I’ve got a few more questions for you Diana. The first question I have is what is the best way for our listeners to connect with you and follow you?

Diana Wu David: I think that they can go to the website at and I have a Future Proof checklist there, which is mercifully short because I have a very short attention span.

I’ve had a lot of people say, “Where do I start?” and I have a couple of questions that just allow you, 11 questions, go through to see where the gaps are. It is a pretty broad outlook and it goes through life, it goes through career, it goes through a lot of things.

And that allows you to think of where can I start, what is it that I want to work on now. Then of course, they can certainly feel free to connect with me on LinkedIn where I spend most of my social media time, or many of the other social medias. That is the one that I pay the most attention to.

Charlie Hoehn: Excellent and the final question is, give our listeners a 15 second challenge basically. What is the one thing they can do from your book this week that will have a positive impact on their life?

Diana Wu David: I think that they can ask themselves, if you lost your job or your industry today, what ideas do you have that could reinvent yourself to take steps and take steps towards making the connections or building the skills and trying things out there? So that is really, what could you do to reinvent yourself if all that what you have right now is no longer available?

For people who find that too daunting, it would really be to write down five things that nurture you. For me, it is going for a walk when things get really bad or going to have coffee with a friend. Very simple and just write them down and put them in your bathroom mirror. In addition to the full bore, ferocious ambition to do new things, you need to have the support that will help you go through a very uncertain process to get fantastic results.