CHAPTER 1

Risk–Reward–Refine–Repeat

HAVE YOU EVER SEEN A PHOTO of an accomplished, energized, and vibrant woman in a publication or on social media, or read a ridiculously impressive bio before a conference or on a company website, and asked yourself: “Wow, I wonder how she got there?” The answer consists of one word: risk. Beyond the accolades, accomplishments, and shiny bios of the most inspiring women with whom I’ve worked are stories of triumph, defeat, trade-offs, tough choices, adversities, setbacks, and lessons learned. Despite their diverse backgrounds and stories, these women who have built bold and brilliant careers all share one core commonality: They seek out and optimize intelligent risks from their first role onward.

Unfortunately, for so many reasons, women enter the workforce believing that they must never make a mistake, and as a result, they see any risk as a bad risk—or overlook the opportunity to risk altogether. The vast majority of early career women I’ve studied report that they don’t seek out or embrace risks. Not only does this result in lost career advancement, it makes taking any single risk seem like the “be all, end all.” Risks are not always pivotal, life-altering scenarios; in fact, taking this view of risk makes it even harder to take them. Fabulous careers are built on a comprehensive approach that includes many risks, taken consistently and strategically, that will result in greater advancement overall than a consistent choice to play it safe. Think of your career like an investment portfolio. Yes, taking bigger bets can increase your chance of higher returns. However, you don’t just take one big bet. You manage your portfolio on an ongoing basis and take many bets. Think of this like the conventional approach to a portfolio: diversification. You never know how one risk is going to turn out, so you spread the risk over a variety of investments. You can think of every risk you take as an investment in your future, your diversified career portfolio.

Risk-taking is a skill you can learn, refine, and practice until it becomes a habit. It’s not a one-off bet or chance. It should be a daily and continuous process of taking an action, a risk; assessing outcomes; refining your approach; and repeating. This is the secret to creating a lasting risk-taking habit: knowing in advance that what you’re doing is part of a long-term and ongoing strategy that will yield important rewards, move you forward, and help you grow no matter whether you succeed or fail on each bet.

Learn to See Failure as a Reward

You may be thinking: What if things don’t work out as I had hoped? The answer: Even if a risk doesn’t have the outcome you hoped for, you can gain exponential growth and insights to fuel your career. An outsized fear of failure is one factor that holds women back from taking risks. However, playing it safe won’t expose you to the learning opportunities that come from stretching out of your comfort zone. Taking risks early in your career can help you learn valuable lessons and move ahead more quickly. It can also help you avoid fatal flaws later down the line. Even risks gone wrong can have exponential rewards. You have the opportunity to use the insights and information you gain in a purposeful way to improve and intentionally craft your career path forward. When faced with failure, Kathleen Taylor, chair of the board of the Royal Bank of Canada and former president and CEO of Four Seasons Hotels and Resorts, considers: “What can I learn? What experience can I gain?”⁹

One of the biggest mistakes is thinking that risk-taking has only two outcomes: success or failure, that is, gains or losses. When you take a risk, avoid the faulty assumption that you will either win or lose. This is a forced dichotomy of extremes that holds women back from taking risks. It is true that a failure may lead to some lost ground; a risk is a gamble, and the possibility of a negative outcome is part of the game. But the reward of taking risks is always progress if you optimize risk-taking and have the right mindsets to learn from the outcomes. In all cases, you will either achieve a goal or learn a valuable lesson that will propel you forward and help you refine your approach.

Make It a Habit

Despite struggling to take risks, the majority of women in a recent KPMG study state that people who take more risks progress further in their careers and benefit in other ways too—by developing new skills and earning colleagues’ respect.¹⁰ They’re not alone in correlating risk-taking with career progression, growth, and credibility. My work and research have highlighted that senior-level women leaders view risk-taking as a continuous practice in their lives and careers. They attribute their success to adopting an adventurous approach to challenges, embracing risk and uncertainty, and having faith in their capabilities to progress regardless of any one given outcome.

Risk-taking is not an isolated action, but rather an ongoing approach to all areas of life, a core aspect of identity. How we think about ourselves has a direct impact on our actions. Flip your script from “I take risks” to “I am a risk-taker.” Risk-taking is not a one-off event but a way of living, leading, learning, and infusing energy, optimism, and growth into your career.

This may seem daunting at first. I want to assure you that I am not by any means advocating for a Russian roulette–style approach to your career. However, taking intentional and strategic risks and continuously refining your approach will reap both shorter-term and longer-term career rewards.

The Risk-Taking Ritual

Building any habit is a challenge. Building a risk-taking habit is even more so, since it doesn’t come instinctively. It takes practice and repetition, and the best way to do this is with a simple, repeatable framework:

Risk – Reward – Refine – Repeat

The framework is intentionally simple so that you can keep it fresh in your mind; write it down and post it somewhere you can see it. In chapter 2, I introduce you to a more comprehensive model for assessing and preparing for bigger, more involved risks, but as a start, think of Risk-Reward-Refine-Repeat as a mental default setting, a life and career mantra. If you keep coming back to this simple guiding ritual, you will establish a robust risk-taking habit that will help you explore bold possibilities today and for the rest of your career.

By leveraging this approach, you’ll be equipped to translate risk-taking aspirations into risk-taking actions, and risk-taking actions into lasting risk-taking rituals that permeate all aspects of your career and life. You’ll learn how to identify Risks, assess Rewards, Refine your approaches, and Repeat the cycle with new insights and information. It’s a process of continuous improvement that will lead to an enduring and rewarding risk-taking habit.

Numerous career decisions and actions throughout your journey may entail risk:

•   Jumping at a challenging assignment or stretch role

•   Saying yes to an overseas secondment or temporary assignment

•   Seeking a new role or a new organization

•   Deciding to go back to school

•   Pivoting into a new industry

•   Taking a sabbatical

•   Putting yourself up for a promotion

•   Negotiating your compensation package

•   Actively seeking out connections with leaders, mentors, and sponsors

•   Raising your hand for high-value and high-visibility projects

•   Chairing meetings and making presentations to key leaders

•   Taking on new and expanded responsibilities outside your areas of expertise

•   Starting an internal initiative or program

•   Seeking new learning opportunities outside your comfort zone

•   Advocating for yourself and others

•   Proposing new ideas, approaches, and uncommon or alternative options

•   Applying for a job when you think you don’t have all the qualifications

In all cases, you can use the Risk-Reward-Refine-Repeat ritual to view risk-taking as a repeatable process of improvement and growth. To kick-start your risk habit, chapters 3 through 12 each include a Risk-Reward-Refine-Repeat exercise, walking you through the approach so that you’ll be well-equipped to use it in your own life.

Risk

The first step is identification: Identify a career risk that you have the choice to take. In this initial step, you find and define a chance in your career that could result in loss or failure. Similar to goal setting, taking a risk begins with clearly identifying an action as your starting point. This should be concisely stated in the present tense and framed as an opportunity or choice you can make.

Ask yourself: “What is the career risk I have the opportunity to take?” And define it.

Complete the sentence: I have the opportunity to . . .

 . . . transition to an expanded career role.
. . . move to another country with my company.
. . . put my name in the ring for a newly created position within my organization.

It may sound obvious, but if you can’t identify a risk, you won’t be able to successfully take one, and it can be surprisingly hard to do at first. I call the ability to identify risks “honing your risk radar.” A poster that reads “Risk is where you least expect it” hangs in Professor Linda Hill’s office at Harvard Business School (HBS).¹¹ Hill currently serves as faculty chair of the Leadership Initiative at HBS. The poster in her room speaks to the fact that risk exists in places you may not have anticipated. This expanded view of risk involves looking for risks that may not immediately be evident.

During the process of producing this book, my editor, Anna Leinberger, shared that in her early career years, she didn’t even identify certain critical and career-defining acts as risks that she had the opportunity to take. She thought she had to keep her head down, get the work done, and “not step on people’s feet.” In hindsight, she reflected that part of the issue was that as woman, we “don’t accurately define things as risks.” Without this ability to discern what constitutes a risk, important bets, chances, and opportunities are either overlooked or not taken strategically. A Harvard Business Review article on gender and risk highlights that we often think about risk in more straightforward, male-dominated ways, such as in physical or financial terms and overlook other types of risk.¹² When discussing risks, many women with whom I’ve worked also fall victim to these limited definitions and think about risk as it relates to handling finances, starting a business, or becoming an entrepreneur. The author of the article states: “The trouble is that historically risk-taking has been framed so narrowly that it skews our perceptions,” which I’ve found in turn influences women’s actions and outcomes.

When women I meet define themselves as “risk-averse,” they’re often thinking about risk within these narrowly defined terms. Risks aren’t reserved for entrepreneurs alone. Risks include speaking up in a toxic culture, advocating for oneself and others, seeking new opportunities, voicing opinions, standing up for what’s right despite opposition, and putting your credibility on the line to support others, among other things. With this in mind, you should build your risk radar by thinking about risk in broader terms, and as Linda Hill encourages, look for risk in areas you may least expect it. The most fulfilled women I have met have viewed risk-taking as a daily activity: “It is not just about taking a few big risks but about pushing yourself each day to get outside of your comfort zone.”¹³ Where fear and discomfort exist, there is likely a risk, a choice to be made. When you feel these emotions, identify the risk you may be overlooking, a career choice that involves a chance of failure or loss, and empower yourself to make a conscious choice about whether to pursue it by using the readiness method described in chapter 2. If you don’t take the risk, the process stops here. However, if you take the risk, the next step is to reflect on the rewards.

Reward

Ask yourself: What are the rewards I’ve experienced as a result of taking this risk? Risking always comes with some sort of reward— whether it be a desired outcome or a lesson learned that will propel your progress. Once you take a risk, the next step is to assess the outcomes and identify the rewards. And remember, “rewards” include both the outcomes of risks that worked out well and outcomes of those that did not. We just need to look at the latter with a new perspective.

Take the example of asking for a critical role on a team project. If you take the risk and are successful, you reap rewards such as achieving your desired outcome—securing the role—and the benefits that come along with that role, such as expanded responsibilities, more exciting tasks, a chance to showcase and further develop your leadership skills, exposure to key executives or clients, or perhaps a chance of earlier promotion.

If you take the risk and are unsuccessful in getting the role, you will still experience rewards. You just need to look at undesired outcomes in a new way. For instance, maybe your manager gave you feedback on why you weren’t selected for the role, and this feedback can fuel your learning and growth. Perhaps you differentiated yourself as someone who is ready and willing to take on challenging assignments, and this has resulted in other opportunities coming your way. Perhaps you gained new insights on what matters to your manager and how you can better align your time and energy to those items. Perhaps you gained clarity on what steps you want to take next in your career. All of these rewards will help you progress further in your career than if you hadn’t risked at all. This step flips the script from viewing negative repercussions and undesired consequences of risks as failures, instead seeing them as opportunities for growth, continuous improvement, and exponential progress.

When considering potential rewards, think about an extended time frame and take a long-term view: The sooner you start reaping the benefits, the longer the tail of returns that you will receive. Remember the snowball effect discussed in the preface. The longer the snowball is rolling down the hill, the bigger it will become. A simple and tangible example is deciding whether to take a lower-paying offer for a “safe” role or taking the risk of a more expansive and challenging entry-level role with a slight edge on pay. When run through conservative predictive models, a seemingly small difference of $5,000 in starting salary can result in a difference in lifetime earnings of over $1 million. The Federal Reserve Bank of New York’s study reinforced this finding, noting that your lifetime earning potential is determined in your twenties.¹⁴ This is one of countless examples that highlight the explicit rewards of risking early. If the risk you have identified is “I have the opportunity to take on a challenging entry-level role with higher pay,” the reward might be “I will make more money and move my career forward.” The long-term expansion would be, “If I make this leap now, I will get to the next level of my career faster; I might make $10K more this year, but if my next promotion comes more quickly as a result, I could be making $20K more within three years instead of only $10K more.” When you add in a compound interest calculation to how much more you could contribute to your retirement savings, you could quantify this one risk into hundreds of thousands of dollars (if not more!) over the course of your career. Each time you take a risk you should complete this sentence: “The rewards I’ve reaped from taking this risk are . . .” Insert any new insights: what you’ve learned, how you’ve grown, what progress you’ve made, what positive outcomes you’ve experienced, how the experience influenced or affected your thinking and your career.

Remember that some rewards are experienced immediately, others within short time frames, and some come later and are experienced long after one takes the risk. Take an initial assessment of the rewards immediately after risking, but don’t forget to revisit this step later on for a second round of reflection, as you may have realized some rewards that were not initially evident or came at a later date.

Refine

Will you let the outcomes of risk-taking define you or refine you? You have the power to ensure that the outcomes of risks, whether desired or undesired, contribute to your continuous evolution and improvement. In the Refine phase, you tweak and enhance your approaches to risk-taking and your career based on what you learned from taking a risk.

Ask yourself: What have I learned from taking this risk that will help me refine my approach to similar situations and other risks in the future?

Think about the example of the risk of putting yourself up for a critical team role. If you weren’t successful, perhaps the next time you take a risk you will refine your approach by ensuring that you have an advocate, such as a colleague or former manager, who can speak to your capabilities and skills, or perhaps you could bolster your case by including more talking points on your track record of demonstrated results and impact (more on this to come in the courageous advocacy chapters). If you were successful in getting the role, perhaps you would refine your risk-taking approach in the future by further honing and enhancing some of the tactics you used that worked well so that you can move from strength to strength.

The foundational work on mindsets by the world-renowned Stanford University psychologist Carol S. Dweck highlighted that girls are more likely to see failure or negative outcomes as part of their fixed identity, rather than something to build on or an opportunity to grow.¹⁵ From a young age, girls are more likely to believe that if they take a risk and fail, they are a failure. Why is this so problematic? Because women equate failure, an isolated outcome, with their identity. The internal dialogue is “I failed, therefore I am a failure.” For boys, the internal dialogue is more likely to be “I failed. Failure is data. What can I do to improve?” What my work and research has shown is that this trend for girls continues into adulthood and hinders a woman’s ability to take the risks she needs to build a brilliant career. In my study of over 120 women, including women from countries such as the US, UK, Australia, Georgia, Italy, India, Jamaica, Bermuda, Malaysia, Norway, Spain, Switzerland, and Zimbabwe, the most pervasive reason that women did not take risks was fear of failure (77 percent). The key to overcoming this outcome and identity conflation is to understand that failure is not fatal and does not define us. Instead, any outcome of risk—positive or negative—should be used to refine our skills and our approaches to risk-taking in the future. Use the outcomes of risk-taking to refine you—not to define you.

Repeat

The final step in this process: Take more risks. Remember that risk-taking is a skill, and like any skill, it can be honed with practice. Here’s the secret about risk-taking: you get better at it only if you do it! While risk-taking is scary and takes courage, taking the risk and managing the outcome builds resilience and skill. The more you do it, the easier it will become. Without a lot of experience taking career gambles, it can be scary to put your cards on the table; however, you can equip yourself to play a strategic game rather than Russian roulette, and then get better with practice. I always tell my clients that “great risk-takers are not born, they are made.”

An added bonus: Risk-taking creates a self-perpetuating cycle. You will define yourself as someone willing to go out on a limb, and this identity will increase opportunities that come your way to repeatedly take risks. How we act and behave influences others’ impressions of us. By seeking out strategic risks, you send the message to others that you are up for challenges, believe in your capability and skills, and are hungry for more. What I’ve seen in my work is that even when a risk doesn’t have the desired immediate reward, differentiating yourself as a risk-taker can reap long-term reputational rewards. I had a client who was initially unsuccessful in negotiating for an expanded role and adjusted title. However, the act of initiating negotiation highlighted her value, the key aspects of her role, and her appetite for taking risks. It planted the seed in the mind of leadership that this was someone up for a challenge. In less than six months, she was internally recruited for a critical leadership role in the organization. Since she positioned herself as a risk-taker and a changemaker, those around her began to think of her as a candidate for key roles. Risk begets risk: When you make a bold move, regardless of outcome, you will have differentiated yourself as a risk-taker; people will think of you when risks present themselves; more opportunities to take risks will come your way; you take more risks; and the cycle continues. Define yourself as a courageous adventurer, a seeker of new opportunities, someone who is willing to go out on a limb, and someone who is open to exciting challenges. Then you will reap the rewards of repeated risks. What risk are you going to take next?

Let’s look at a real-life example of what the Risk-Reward-Refine-Repeat approach looks like in practice.

RISK. After displaying a proven track record of results and having discussions with leadership, Robyn took the risk of going for a promotion at a top-tier consulting firm.

REWARD. She was not successful in securing her desired outcome. Despite the disappointment of not getting a promotion, the decision was a catalyst for her to reflect on and go for what she really wanted. She realized that she was undervalued in her current context. She could have continued in maintenance mode, but she felt that accelerating her career was important, as was being valued for her contributions. The seemingly negative outcome of her risk-taking was a catalyst for these new insights: her rewards.

REFINE. This risk-taking experience refined her outlook on the type of companies she wanted to work for and what was worth risking. She also refined her risk-taking approach, ensuring that she went into future discussions with courage, an understanding of her value and a clear narrative.

REPEAT. She went on to take another risk and apply for a stretch role at the world’s leading internet-based companies. She was successful and was hired into a role that was more aligned with her skills and values.

This story wasn’t as simple or short as I described above. It took support from others, including a therapist, journaling, and other reflective techniques to dig deep into what she wanted. She also moved back in with her parents in her early thirties and grappled with self-doubt and fears. However, in the end, taking an initial and repeated risk created progress she would not have made by playing it safe.

Get Equipped and Get Going!

In 2016, I was invited to speak at the Women’s Forum for the Economy and Society in Normandy, France. I shared the stage with a magnetic and energized social impact entrepreneur, Melody Hossaini, of the same age, thirty years old, and still in the earlier stages of her career. Melody was no stranger to risk. She was the founder and CEO of the social enterprise InspirEngage International, and was best known as a contestant on the seventh season of the BBC television series The Apprentice, where she made it to week ten out of twelve. As we stood on the stage in front of an audience, virtual and in-person, of three thousand, she shared that sometimes you may need to go backward to propel yourself forward. Standing on the 360-degree stage, she explained that jumping from her current spot to the other side of the stage was difficult, particularly in heels and a dress, and asked how she could jump farther. Then she backed up and, with a running start, made a longer leap. “If you want to go really far, go back first and then charge forward,” Melody said. “The challenges and failures we face in life are these steps back that allow us to go further than we would have if we just started from here—but only if you allow that to become a part of your journey.”

That journey involves making Risk-Reward-Refine-Repeat a habit, an enduring ritual in your career and life. The practice isn’t just about taking one big leap but rather about taking many leaps over the course of your career. Think back to the example at the beginning of this chapter of developing an investment portfolio. Like a traditional investment portfolio, your career portfolio requires ongoing management, continual investment, and diversified risks. It isn’t a one-and-done scenario; it’s a continuous way of living. We all have the power to take risks and adopt a Risk-Reward-Refine-Repeat ritual of behavior in our careers. We just need the right tools and the right mindsets, as outlined in this book. We just need to get equipped and get going.