Redefining What Success Means For You

Redefining What Success Means For You

The following is an edited excerpt from the book Future Proof: Reinventing Work in the Age of Acceleration by Diana David.

                   Success is liking yourself, liking what you do, and liking how you do it.


The forces of competition and change that threaten business and industry also threaten individuals and their careers. If you don’t stay ahead of the curve, you’ll be blindsided by change. “Inaction is especially risky in a changing world that demands adaptation,” says Reid Hoffman.

If it’s no longer likely or even possible to spend forty years at one company, staying put is also a risk. It’s time to be smarter about risk by diversifying your options and redefining success in the context of life instead of a specific job. Now, “succeeding…doesn’t mean finding a job. It means creating a more aligned, better-balanced life, and finding satisfying work that helps achieve your vision of professional and personal success.”

Don’t settle for the life you’ve been given; prepare for the life you want.

Reconsidering The Idea Of Success

Now that you’ve learned skills to build upon for the future — experiment, reinvent, collaborate, focus — and adapted them to your own journey, it’s time to see how to use them to redefine success on your terms. It’s time to take the learning you have and pioneer new pathways to a life of trust, respect, balance, purpose, and joy. It’s time to shed the external markers of success to make room for internal confidence. You can move to a place where you are perpetually expanding your contribution and progressively realizing the goals that will make up your life’s work.

People have different measures of success, but there is a movement away from the traditional measures of money and power. Emma Sherrard Matthew, the former Global CEO and now Executive Chairman of Quintessentially, a luxury lifestyle membership, has had a ringside seat watching her ultra-wealthy clients navigate their work and lives. She noticed that time was the greatest luxury they were seeking.

“Seeing all these incredible people, I noticed a trend. They have made an absolute fortune and they couldn’t spend it because they have no time.”

This resolution led her to craft her own portfolio career. This doyenne of luxury living now defines success by working with the people she likes, paying it forward by mentoring startups, and having time to spend with her young children. She has redefined success, for now, on her terms and laid the groundwork to be agile as she goes forward and as her priorities change.

Dan Wen Wei, a famous musician in China, was my next-door neighbor at the top of a fifth-floor walk-up back when we were starting our careers in New York City. Dan is now at the top of his game professionally, and likewise has found that time is wealth. After being a concert pianist in New York City, he returned to China where he is currently at a conservatory. There is a long waiting list for his teaching expertise, and he can pick and choose his students. In fact, he has to be choosy due to the high demand. He is often approached by celebrities or billionaires hoping to have him teach lessons to their children. His reply is, “I’ll only work with those who want to do this professionally and full-time.” Success for him is the opportunity to do what he loves, with people who share his passion and commitment.

Role Models For The Next Generation

One reason I felt compelled to write this book is becauseI feel that, although people are raising their kids differently than in the past, we are still in an era of time-worn expectations about success. I told my daughter recently that she didn’t have to get good grades, that it’s more important to learn in a way that fits her best, paying attention to her strengths. The way she makes friends, interacts with her teacher, and understands and manages expectations has equal impact.

She asked me, “What should I do in my life?”

“You’re twelve,” I replied. “It doesn’t matter right now.”

“What if I decide that the one thing I want to do in my life requires really good grades?”

I mumbled an anemic return argument but quickly realized she had the upper hand.

Kids today are very competitive. They’re apprehensive about getting into good schools; they’re in tutorial studies to gain every extra advantage. Ironically, it’s much the same as the external pressure adults put on themselves. If all you’ve ever done is chase whatever seems to be right at the time without understanding your values and your talents, that method may get you a great first job but rarely is it the sole ingredient to a meaningful life.

Feeling like you’re only able to succeed on your current path, unable to do anything beyond your existing industry, company, position, and skills, is a brittle definition of success. You can move away from prizing external validation, such as salary or titles, create new ways to evaluate success, and move toward valuing progress that reflects your unique values and priorities.

The Challenge of Finding Purpose

Many people are just hanging on. Others love the excitement of their jobs but know their role may have a limited shelf life, yet they have no conception of the alternative. Finding the next job is fairly straightforward; it’s much harder to ask yourself — and figure out — what kind of life you want to have. As Natasha O’Brien, an HR services executive, laments, “There is so much information out there about success, but people still don’t know who they really are.”

Why is this so difficult? Several factors contribute to this problem, one of which is the challenge of leaving one shore filled with society’s ideas to go to an unknown place you can’t yet see. Stanford’s Bill Burnett calls this “the society factory,” with status, prestige, money, and power. That is the ecosystem in which most of us work; it’s a factory that makes us and subsequently molds us.

To find new shores, you have to turn away from the one you’re on and look to the horizon. Christopher Columbus said, “You can never cross the ocean unless you have the courage to lose sight of the shore.” For most of us, it’s not easy to let go of the shore and that lifeline we’re used to.

One of my favorite philosophers, David Brooks, has a saying for this tendency to stick with what we know: “we’re walking in shoes that are too small for us.”

Tight shoes are the pits! Think about that for a minute. You know you have more potential, more audacity. It’s a vivid image to think of yourself trying to fit yourself into something that just doesn’t quite work, and you owe it to yourself to figure out something that does work.

How Will You Measure Your Life?

At Clayton Christensen’s fiftieth Harvard reunion, he realized that many of his classmates were enormously successful in their careers and proportionately unsuccessful at life. In fact, they were miserable at life because they had invested in their careers at the expense of everything else. His book How Will You Measure Your Life? attempts to put that question to a wider audience. Is our own individual, professional success worth it? What is the cost?

In the beginning of the documentary, The Diplomat, director David Holbrooke makes the startling claim that only after his death did he realize his father, Richard Holbrooke, was a historical figure. The film is a fascinating look at the brilliant but divisive statesmen, ambassador Richard Holbrooke, made more poignant by the fact that his son manages to interweave the professional success Holbrooke had working on highly visible projects like negotiating peace in the Middle East, with the very personal story of a man largely absent from his family. As he goes through the process of making the film, David realizes his father’s sacrifices in pursuit of his passions, but realizes he is successful in his own right on his own terms, which are very different from his father’s.

The late Holbrooke was a known figure around the office at my first job after college, working for Henry Kissinger. Kissinger, who has the noble distinction of having served as Secretary of State under President Nixon, and as my first boss (surely, a unique niche) put extraordinary effort into his work. Many people respect and revere him, others dislike him, but either way, he has made his mark on history.

Perhaps that time was the “great man era” but you wouldn’t have to look far to find modern equivalents, where people sacrifice everything to the altar of performance. In an era before cell phones, the entire staff carried pagers and used phone booths to dial in to the office if anything was needed. However, like Richard’s son, David Holbrooke, while I have an appreciation for the dedication, I am not willing to make certain sacrifices to bathe in the powerful, political, and at times, celebrity limelight.

I didn’t completely learn my lesson from working for Henry Kissinger. My work in consulting, which I spoke about in the introduction, was also 24/7. I spent every waking moment at my job. Even Sunday — my supposed day off — was spent doing laundry and expenses, and repacking for the next day. A car would appear every Monday morning to take me to the airport. I’d fly home Friday night, and if I was lucky and the flight was on time, I could catch dinner with a friend. Half the time, my flight was delayed, and my friends had already eaten and were ready to go home.

One of my friends said, “I just never know when you’re at home, so I don’t know if I should call.” She eventually stopped calling altogether and that made me realize (if the thirty pounds I’d gained eating room service didn’t) that I was living an untenable life. There are people who thrive on that kind of life, but I realized I wasn’t one of them. Taking ownership of that realization helped me move forward toward a life I wanted.

When we talk about our lives now, it’s easy to blame our 24/7 work life on the advent of technology and smartphones (or maybe, in the Kissinger example, the invention of the pager). Who hasn’t waxed nostalgic from time to time about an earlier time when life seemed simpler?

I had a chance to test this question on the elder of a nomadic clan in Mongolia while I was horse trekking in the Altai mountains with the founders of the Nomadic School of Business, who were there studying nomadic mindsets. We were camping on the clan’s land. They have managed the clarity of purpose, agility, and sustainability we now seek for ourselves; moving every season but able to keep their family together throughout generations. I wanted to know how technology was affecting that equation as cell phones, solar panels, and even TVs showed up in families across the area. The elder said, for them, technology was a blessing.

Solar energy, for example, allows them to charge phones and maybe watch a movie at night or use a computer to sell their horses online. They can use cars instead of camels to move camp each season, and motorcycles to travel quickly between different villages, a task that used to take days. They welcome the tools and put them to good use but are not ruled by them. They remain respectful of the land, their rituals, and their purpose. They have a common identity and purpose, and their collective goal is to caretake the earth for generations to come.

Minimum Viable Lifestyle

Having a financially sustainable lifestyle gives you the flexibility to define success in broad terms. We reasonably think about work choices in the context of income. The more neglected side of the equation is cost. The more income we have, the more we invest in a lifestyle that gives us prestige among peers and the creature comforts that motivate us to keep working at maximum capacity. We build up expensive and demanding cost structures leading to an overhead that’s often unsustainable in later life and rarely put into the context of the tradeoffs needed to pursue a broader definition of success. This doesn’t need to hold us back. By planning ahead, we can ensure that we thrive in our lives as a whole, including career. We won’t fall off a financial cliff, surprised by a health issue or redundancy, or caught out by a longer life and shorter terms in a more volatile world of work.

Extremely intelligent people who are totally capable can become completely absorbed in the immediacy of their work. They’re always on and always connected, and their careers are increasingly demanding. Just getting through the day can be exhausting. Instead of worrying about where the next job is coming from, ask yourself, “What kind of life do I want? Maybe what I have works for now, but is this what I want in ten years? What kind of meaning and impact do I want to have? What do I want my legacy to be? What kind of connections do I want to make? What purpose do I want to live by? What values do I want to live by?”

Studio executive Todd Miller is CEO of Celestial Entertainment and a veteran of the entertainment industry. He is a great planner and is perpetually mystified by how people don’t plan well, financially or career-wise. He feels most executives don’t think sufficiently far ahead and are only focused on what’s next, either a promotion or the boss’s job or a great job at another company. Most people don’t take the time to think in terms of five or ten or twenty years, and to prepare for that.

Years ago, faced with career burn-out, Todd took a sabbatical to bicycle across the United States and figure out his focus. He saw that many of his friends hated their jobs but were just hanging on by a thread because they had set themselves up with an expensive lifestyle. This was his wake-up call to rethink his own next steps and reorient from planning for his next job to crafting the rest of his life. He realized that he did love his work and set about creating a plan to invest further in his career in a way that allowed him to do his work on his terms. He reviewed his costs and began to research investments that would allow him to be less reliant on just income, developed a retirement plan far in advance that included a great bungalow by the beach, and started developing the relationships and board seats that will ultimately provide interesting intellectual stimulation and ongoing work as he shifts into more of a portfolio career.

To think about setting up a minimum viable lifestyle or MVL to enable more choices in life, consider non-negotiables. I am lucky to be in a dual-income household, so we have more flexibility but lowering my income to write a book wouldn’t feel right without first making sure my family was taken care of. If one day my children have their own ambitions and they cannot go to university because we can’t afford it, I would feel like a failure as a parent. While, as Americans, we had the opportunity to set up college savings plans; these were accelerated to ensure each child had at least a year’s schooling at a private school (no small feat!), and we will figure it out from there. We focused most of my income on savings and making a certain amount of headway toward retirement.

The second aspect of this is to have a crystal-clear idea of the worst-case scenario and plan of what you will do in that instance. Then you can conjure up some mitigating plans to ensure the worst does not come to pass or that you are prepared when it does. Business strategists incorporate it into scenario planning; author and self-experimenter Tim Ferris calls it “fear-setting” and says it’s one of his most important tricks, while Silicon Valley pundit and founder of LinkedIn, Reid Hoffman, calls it “having a plan Z.”

This is knowing in advance what job you might go for when your startup blows up and you need to get some cash to pay your credit card bills, or the sabbatical you take becomes a lot longer because your company restructures. It’s the best worst option. It means imagining what life you have in that scenario, what apartment you live in, what food you put on the table, and how your life changes. That is the extreme Minimum Viable Lifestyle.

I’ve heard multiple versions of this. When I started a portfolio career I asked a colleague who had gone from being a hedge fund manager to a journalist what she missed the most about her former lifestyle. “Nice shoes,” she said. Lifestyle maven Emma Sherrard Matthew mentioned that one of the hardest things is “giving up a big salary, working out the daily cashflow. I do have income from being a chairman and from some of my advisory but much of it is angel investing, which will take three to five years to materialize. It’s an adjustment.” Coach Danny Khursigara mentioned eliminating financial anxiety in order to be able to focus on the longer-term ability to add value. Todd has his beach house in Thailand to fall back on.

Most of this book is about keeping a job you have and beginning to build the skills necessary to move into a more flexible work that will carry you through the second half of life. However, even if you did stay in a well-paying, prestigious corporate job, you would be at risk of redundancy or mandatory retirement, so it is worth planning ahead.

What Does Future-Proof Success Look Like?

There’s been a lot of discussion lately about what work will look like in an age of globalization and automation. I think we’ll see people coming together, collaborating on joint experiments, and solving important problems. So what does a future-proof life look like?

A future-proof life is one that has considered how to mitigate the risk of accelerating change and disruption by being prepared mentally, professionally, and financially. It is a life with a broad enough definition of success to honor the experiences, relationships, and opportunities you’ve achieved, not just milestones of achievement externally defined. It is always adapting and proactively seeking the next learning opportunity aligned with values and focus. Honoring yourself in more varied and creative ways contributes far more to your ultimate success. Hopefully through the activities, and also the many examples and stories throughout this book, there has been enough for you to imagine what a future-proof life looks like for you.

Reflecting back to my corporate lawyer friend, Jennifer: she didn’t love every aspect of her job but thought a lot about her values and desire to help people. By doing so, she expanded into a role in thought leadership. This helped her win the top employment lawyer award in Asia, which she might not have been able to do without taking a close look at her passions. She followed her curiosity to a natural place where she leveraged her experience into something new, challenging, and exciting. Likewise, Lale Kesebi launched her strategy lab,, to broaden what she did for one organization to other companies trying to build great businesses for humans.

Both redefined success, beyond just clocking in and out every day, to reach further and be more ambitious about living their own visions of success.

An Action Plan For Success

I hope at this point that I’ve given you some ideas about your own future. My goal has been to show how certain minds thrive in uncertain times and give you the tools to do so as well. It’s not easy to break from enduring habits, belief systems, and past prestige to explore and find new ways to grow personally and professionally. The greatest resistance we sometimes meet is ourselves. Yet we owe it to ourselves to create alternate opportunities and plunge in bravely past our own resistance to set a new course to new ideas of success and significance.

Remember that success can be broadly defined. A rigid definition exposes you to the risk of not realizing that the winds are shifting, and you might not be ready. The company you work for may no longer be around in the coming years, or the industry might be dramatically disrupted. With self-awareness and courage to act, you can prepare for those kinds of events and capitalize on the lack of structure to create one that best serves you.

Don’t wait for success to come to you and don’t think that once you have it, it’s there forever. Think about where you are today, where your work is heading, and take calculated risks to get where you want to be. Most people reading a book like this are already in that frame of mind or they’re nervous and not exactly sure how to move forward. Yet they have a lot of career capital and can become leaders in the new economy.

To maximize your potential, it’s vital to think, reflect, and shift your perspective. Many of us are already leaders of some sort, which makes us even more responsible to think and re-imagine the future of work for ourselves and others. Get out there and challenge your ideas. Craft your own life and role model the possibilities of the future. It’s time to act.

To keep reading, pick up your copy of Future Proof: Reinventing Work in the Age of Acceleration by Diana Wu David.