How to Develop a Career Competitive Advantage (Episode 4)

In 2012 I read a book that had a profound impact on me and shifted how I think about my career.

That book is The Start-Up of You by Reid Hoffman and Ben Casnocha.  The authors argue that we can develop a competitive advantage by answering questions regarding our assets, our aspirations, and the market realities.

1) Assets: What are you inherently good at? What do you have going for you? These can include soft assets (knowledge, skills, connections) and hard assets (cash, investments).

2) Aspirations: Where do you want to go in the future? What do you want to do? Who do you want to become?

3) Market Realities: What will people actually pay you for? Where is there a market demand?

In my latest video, I dive into these three critical questions, sharing how these questions inspired me to make a career pivot and how they can help you build a career competitive advantage.

Fortune Favors the Bold (Episode 3)

Being bold is important in all aspects of our lives, but it’s especially critical in our careers. I learned this lesson firsthand when my friend Ned’s boldness and creativity helped him find his dream job.

In Episode #3 of the Not Your Parents’ Workplace Show, I walk through why fortune favors the bold, share the story of how Ned landed the job, and provide two tips on how YOU can be bolder than ever.

What Pitbull Can Teach You About Building a Powerful Network (Episode 2)

What comes to mind when you hear the word “networking”? If you’re like many, you think of an extreme extrovert at a cocktail party or networking event, glad-handing and dishing out business cards to everyone in sight. Ughh. We know networking is important, but does it have to be so painful?

In my second video, I share tips on how to network in a more focused and authentic way, as well as how to build a personal board of directors.

Going forward, I plan to post one video per week. If you like what you see, subscribe to the channel so you can catch future ones!

5 years ago I published the career strategy book, Not Your Parents’ Workplace. In it, I share the challenges I faced and the lessons I learned during the 2008 financial crisis and beyond. Within a year of graduating college, I worked at three companies, enduring the largest bankruptcy in history at one and getting laid off by another. It was a brutal period I’ll never forget.

We’re now in another period of economic uncertainty. Many have lost jobs and others are worried about what the future holds. In light of this, I’ve decided to try something new. I’ve kicked off a series where I share stories and lessons from Not Your Parents’ Workplace as well as insights I’ve had over the last five years.

Career Q&A with Ryan Seamons, Co-founder and Chief Product Officer at Sprintwell (#8)

Our next Career Q&A is with none other than Ryan Seamons, Co-founder and Partner at Sprintwell. There’s a lot of goodness throughout. I’ve always been impressed by Ryan’s commitment to learning and how intentional he is in living his life. Enjoy!

Ryan Seamons is co-founder and partner at Sprintwell. They help teams build habits of innovation without burning out. Ryan believes that everyone can do meaningful work, and that people growth and product growth go hand-in-hand. 

After a decade working in product management, Ryan loves helping others understand the mechanics and mindset that drive great product teams and save companies time, money, and energy. Ryan created the first internal version of LinkedIn Learning and led product teams as Director of Product at Degreed. 

He is passionate about education and family. He and his wife write about intentional family living from their experiences homeschooling their 5 children. He also created the “What do you really want?” newsletter with weekly conversations about getting what you want at work and in life.

ryan seamons

What’s a book that has influenced your career or life, and why?

First, Break All the Rules. This book got me into organizational behavior. It was eye-opening to realize that many people go into management not because they would be good at it, but because of the additional income and power. 

Gallup calls this the “blind, breathless climb”. This explains a good percentage of incompetence and friction at work. Just because someone was a good individual contributor doesn’t mean they will be good at managing other people doing that thing. We promote people just beyond their capabilities. 

That book was the beginning of my finding the problems I care deeply about — the reality that:

  • Most people don’t like their jobs.
  • Many managers aren’t ever equipped and enabled to guide meaningful work.
  • Often companies have no idea how to build sustainable habits of innovation.

There’s a better way. We should all be able to find meaning in our work. Management can be a noble profession. And innovation is more like math than magic. 

Was there an experience you had before age 21 that shaped who you are? What was it?

I served a 2-year mission for my church in Bangkok, Thailand. While the entire experience was incredibly formative, the most impactful part was 9 of those 24 months spent living with native Thai companions (missionaries pairs are called “companionships”). 

It’s incredible to spend 24/7 living with someone from a different cultural upbringing. To speak their language and learn about their country and culture by observing them. I made too many mistakes to count. My world view was challenged over and over again. But not a day goes by that I don’t use the skills of empathy, observation, patience, and compassion that I learned from my time with them. 

How has a failure, or apparent failure, set you up for later success? Do you have a “favorite failure” of yours?

Lots of failures to choose from. 😂

My favorite failure ended up being the best thing that happened to me. I dated this girl in high school that broke my heart, per my mother’s encouragement (my mother didn’t want me dating seriously so young). I was hurt and discouraged but moved on. 

A few years later that girl and I reconnected, had a quick engagement and got married. We were both a little older and wiser and the time allowed us to both grow up. A decade of travel, entrepreneurship, and 5 kids later I realize the best thing in my life probably wouldn’t have happened had it not ‘failed’ first. 

Thanks, mom. 

What advice would you give to a smart, driven college student about to enter the “real world”? What advice should they ignore?

1) Never stop learning. Most people get stuck because they stop learning. 

2) Spend time early and often deciding what you really want. Too often we choose a path for the wrong reasons. It’s easy to accept the script of others but it ends up being the #1 regret at the end of people’s lives

3) Be Bold. I got my first internship by first being told that a recruiter “wasn’t looking for interns, only full-time”. I was about to leave, but then turned back around and asked, “well, if your company were to recruit an intern, who would I talk to about that?” He sized me up for a few seconds, then handed me his business card with the email of a colleague written on it. That one moment of boldness turned into an incredible experience where I first got exposed to applied bioinformatics, web development, design, consulting, database, etc. Many skills I have used in my career came from that moment of boldness. 

What are the bad recommendations you hear in your profession or area of expertise?

“The Product Manager is the CEO of the product.” It’s a horrible mindset that leads to a lot of stress and poor expectations. Too many people go into product management because they think they will be in charge or be able to call the shots. That’s rarely the case. 

A product manager is a lot more like an American football quarterback or a pirate captain. You have to be a master of influence without authority. Your job is a lot more about alignment, inspiration, and communication than many expect. The hard skills of market research, analytics, prototyping, etc are important, but if you don’t build trust with your stakeholders and team, you’ll never deliver value to customers in the way you hope.

So many teams grind to a halt because product managers don’t prioritize the people side of product management. 

If you could go back in time to when you were entering the workforce and give yourself one piece of advice, what would it be?

Optimize for learning. Learning compounds just like money. Given the choice, choose the opportunity where you’ll learn most.

This has driven my choices in schooling, switching teams/companies, and how I spend a good deal of my free time. More than ever you will stand out by intentionally learning (vs binging on Netflix or social media). There is so much knowledge out there. Spend a few minutes each day consuming in a high-quality way and you’ll stand out with your ability to help others and lead change.

Who is one person, dead or alive, who you admire? Why do you admire them? 

Stephen Covey. I love the stories about how he prioritized his children, even while working hard. I hope to influence just a few people the same way he influenced millions.

What habit or practice helps you manage stress? 

Whenever my wife and I are stressed out or overwhelmed, we have a “whiteboarding session”. 

This is a technique we use in our consulting at Sprintwell to help teams get clarity and alignment. But it works incredibly well for individuals or couples as well. 

We pull up a whiteboard (or document) and go through the following steps:

  1. Write down what’s going well. 
  2. Write down what’s not going well, stressful, or needs to get done
  3. Organize the list, putting like items together and then sorting by priority. 
  4. Make some quick decisions about next steps. 

This always gets us unstuck and facilitates positive conversation and action.

When have you felt stuck in your career? How did you break out of it or push forward?

I had a boss who once told me that I didn’t have what it took in the career path I was hoping for. I remember being devastated. I was pretty mad walking out of that 1:1. I distinctly remember realizing that I could decide how I responded. I decided to ask myself, “what can I learn from this?”

Suddenly I realized how much I could learn. I did have a long way to go. So, I got to work learning. Now, years later, I’m sharing the knowledge I learned with product managers and leaders at some of the world’s most successful companies. I might not have built that expertise if I hadn’t been “challenged” by that boss. 

For more Career Q&As, click here, or you can check out my monthly newsletter.

 

Comparison is the Thief of Joy. Here’s the Antidote. (Episode 1)

5 years ago I published the career strategy book, Not Your Parents’ Workplace. In it, I share the challenges I faced and the lessons I learned during the 2008 financial crisis and beyond. Within a year of graduating college, I worked at three companies, enduring the largest bankruptcy in history at one and getting laid off by another. It was a brutal period I’ll never forget.

We’re now in another period of economic uncertainty. Many have lost jobs and others are worried about what the future holds. In light of this, I’ve decided to try something new. I’m kicking off a series where I share stories and lessons from Not Your Parents’ Workplace as well as insights I’ve had over the last five years.

Here’s the first video. I’d love to hear what you think and if there are specific topics you’d like covered in future ones!

Daily Gratitude: Marco Polo (Day 1,086)

In April 2017 I kicked off a gratitude challenge where I wrote a daily blog post for 30 days (more on my learnings here). When the challenge ended I decided to continue the habit but only occasionally share gratitudes on my blog.  

One of the challenges I’ve faced while physically isolating during COVID-19 is the lack of connection to the outside world. Marco Polo (no, not that one, or that one) is a video chat app that’s been a gamechanger for me.

There are countless ways to stay connected. Phone calls, Facetime, and Zoom/WebEx are great for real-time, synchronous communication. They’re great for talking with friends, family, and colleagues at the same time. Text messages work well for asynchronous communication and I love being able to respond at times that are convenient.

I love Marco Polo because it provides asynchronous video communication. I experience the joy of connecting face-to-face but don’t have to get everyone together at the same time. Through Marco Polo, I can watch video messages at my leisure, then create and send a video when convenient. It’s super easy to use and makes staying in touch fun.

Isolating physically has been a challenge for me and countless others. Meaningful connection is a basic need for everyone and I’m grateful we have technology in Marco Polo that can help fill that need.

Career Q&A with Lisa Lee, VP of Global Culture, Belonging, and People Growth at DoorDash (#7)

Our next Career Q&A is with my friend and colleague Lisa Lee, VP of Global Culture, Belonging, and People Growth at DoorDash. Lisa provides fantastic advice on bouncing back from failure, creating stronger and more inclusive teams, and the need to continually invest in building relationships.

Lisa Lee is the VP of Global Culture, Belonging, and People Growth at DoorDash. She oversees Employee Connections, Diversity & Inclusion, Internal Communications, and Learning & Development, weaving together these four critical areas to create an interconnected strategy so DoorDash’s employees can do the best work of their careers.

Lisa joins DoorDash from Squarespace, where she led the creation of its first diversity and inclusion strategy. Before Squarespace, Lisa served as Pandora Media’s first Director of Diversity and Inclusion Strategies. Prior to joining Pandora, Lisa was at Facebook where she led initiatives in User Operations, Product Operations, and Diversity Programs.

Lisa served as the publisher of Hyphen magazine, an award-winning publication about Asian American arts, culture, and politics, co-founded Thick Dumpling Skin, a positive body image community for the Asian American community. Most recently, she co-launched The Margin, making space for people of color at conferences around the world.

lisa lee

What’s a book that has influenced your career or life, and why?

Bryan Stevenson’s Just Mercy is a book I will forever remember not just for the important message it has for all of us, but also for the way it made me feel. 

Just Mercy documents Bryan Stevenson’s life long quest to free wrongly convicted people from death row. The majority of his clients being poor people of color from the South who were targeted in a justice system that is systematically unjust. 

I remember the day that I finished the book, I went to a meeting for a nonprofit organization that I volunteered with and just cried the whole drive there. In doing diversity and inclusion work, one can easily become so well versed with the data and “the business case for diversity” that it’s easy to forget about the lives of real people who are impacted as a result of racism, sexism, and other forms of bias. Bryan Stevenson’s message reminded me that if we want to solve the problems that we see, we must become intimate with the people impacted and the system that perpetuates those persistent problems.

Was there an experience you had before age 21 that shaped who you are? What was it?

I was born and raised in Taipei, Taiwan. At the age of nine, my family immigrated to South Africa and we immigrated again to Los Angeles, California when I was 15. Throughout, my parents weren’t always with me and my siblings because they worked abroad to provide for us. 

The experiences of assimilating within such vastly different cultures without a traditional family unit had a profound effect on me in my understanding of the world and myself. I learned to be independent and to trust myself (as much as this is a lifelong journey). I learned to be resilient and to acknowledge my differences. I also learned that you can learn from everyone around you, especially those who don’t look like you or reflect your upbringing. 

How has a failure, or apparent failure, set you up for later success? Do you have a “favorite failure” of yours?

Earlier on in my career, I prided myself on being principled. I had a strong sense of right and wrong. Frankly, I probably felt like I was right most of the time! While this served as a guiding light for me in my life, it didn’t help me to be a great listener and I didn’t always make room to understand other people’s perspectives. Rather than asking myself, “how can I make sense of this?”, I would double down and become frustrated. 

This lack of curiosity on my part resulted in some major failings with internal partners and stakeholders, where even as I wanted to lead, I was getting further and further away from that goal. 

Looking back, the failures helped me to learn a few things: 

  • Listen, and do not listen to speak or defend. Listen to understand the other person’s perspective and the impact that you had on them through your actions 
  • Hone and master your craft. Deliver excellence always, even when it is hard. If you’re thinking that people have different standards of excellence, sure. Then go back to #1 and also ask yourself “am I putting out work that I am proud of?”
  • It’s ok to feel ashamed, but don’t let it erode your faith in yourself. We all have our good days, bad days, highs and lows. Take the time to acknowledge, “I could’ve handled that better” and even sulk for a few days is absolutely ok! But don’t beat yourself up to the point when you’re so down on yourself that you can’t see clearly. 

What advice would you give to a smart, driven college student about to enter the “real world”? What advice should they ignore?

Graduating from high school, I didn’t get accepted to any of the schools I had my heart set on. Growing up in a community where mostly many people in my circle touted their prestigious school acceptance like a badge was especially tough. It was around that time that my dad told me that life is a marathon, so don’t let one milestone (or the lack thereof) be the determination of where you’re going. This stuck with me. We all have our own timeline, even if you don’t know where that destination is. Focus on being the very best at what you get to do every day. Be prepared, do your homework, and ask questions. Be open to all possibilities, and friendships, because you never know what doors people can open for you. 

This may be an unpopular opinion, but I would ignore the advice around “don’t worry about money,” or “just follow your dreams.” Financial independence for me was incredibly important since my family was far from well off. At a young age, I knew that my parents were under a lot of pressure for taking care of their four children and I knew that I wanted to 1) not be a burden on my parents financially, and to 2) take care of them one day. Depending on your circumstances, money could be a very real reality for you. Find ways to feed yourself and your family (literally), as well as your soul. It may mean putting in more work, after work hours, but know that the two are not mutually exclusive. 

What are the bad recommendations you hear in your profession or area of expertise?

These are more common mistakes that get shared out as good practices rather than bad recommendations.  

  • Start with “gender diversity”: Gender diversity is oftentimes, in action, synonymous with increasing, promoting, and retaining white women. This is dangerous because it implies there’s a pecking order in how a more diverse and inclusive workforce can and should be achieved, and it further ostracizes and excludes women of color (and men of color) by not addressing experiences that they’ve had. 
  • Setting up Employee Resource Groups as (the start to) a company’s diversity and inclusion (D&I) efforts: Employee Resources Groups can only be as successful as the leaders of the company want them to be. They’re oftentimes seen as fun extracurricular activities that only the employees themselves care about, yet companies like to tout them as a badge of honor. It’s important to remember that Employee Resource Groups are oftentimes formed to yes, build community, but also to address gaps that underrepresented employees feel, whether that is a lack of representation in the company’s leadership or practices that could be improved to be more inclusive. Therefore an incentive and reward structure needs to be created to sustain Employee Resource Group participation, and funding, as well as leadership involvement, needs to be built into the structure from the beginning. 
  • Focusing D&I efforts mostly on recruiting, or at the talent attraction level: Many companies think of D&I as a recruiting problem, and think that investing in recruiting is a good start, instead of looking at the employee lifecycle holistically. While it is important to set goals around increasing underrepresented people in the applicant pool, it is just as important to ensure that people can come into your company and grow to have meaningful impact. 
  • Learning and Development efforts being separate from D&I efforts: “Unconscious Bias Trainings” have traditionally been divorced from manager trainings and other curriculum offerings at a company. Amongst training topics, such as coaching and delegation, where unfair treatment often happens, it is important to educate how bias can cause us to give disparate amounts of time to people of different backgrounds and how we may inadvertently delegate more “house” work to women, such as note-taking and planning team offsites. In order to correct unhealthy power dynamics at work, especially if your company has had a more homogenous workforce, it is key to embed D&I training into all L&D efforts because it is incumbent on everyone to create an inclusive culture that will enable diversity to grow. 

What’s one of your proudest professional accomplishments? 

In addition to purchasing my own home before I turned 30, I’ve been able to support my parents and siblings in their home ownership. As an immigrant and a child of immigrants, I’ve spent most of my life being obsessed with the idea of “home” and I love that we’ve been able to find it and create it for our family.  

What habit or practice helps you manage stress?

A few years ago I made physical fitness a priority to help me manage stress and to feel more balanced. I work out with a kettlebell trainer twice a week and go to yoga about twice a week. During the summer I love biking in New York as a form of (fun) commute. 

I also set reading goals every year to get through a number of fiction books. To reach the goal, I go down the rabbit hole of finding my “next book” and it can be fun researching. 

One of the greatest benefits of living in New York is, of course, experiencing great art! I was a theatre and performance studies major in college so I make sure to attend theatre performances, live music, and even comedy. It’s always inspiring to be wow’ed by other people’s creativity, which helped me to think about how I can be even more innovative in my own work. 

If you could go back in time to when you were entering the workforce and give yourself one piece of advice, what would it be?

Invest more time in relationships. Given that I had a lot of interests outside of work, I didn’t spend a lot of time getting to know my coworkers because I always had somewhere to go, whether that was volunteering or my existing friend circle. Many people that I used to work with are doing absolutely incredible things now with their lives and I could be learning more from their journeys.

For more Career Q&As, click here, or you can check out my monthly newsletter.

Career Q&A with Kelly Palmer, Chief Learning Officer at Degreed (#6)

Our next Career Q&A is with Kelly Palmer, the Chief Learning Officer at Degreed. Kelly offers great advice on managing career transitions, developing confidence, and the three “power skills” that will make you successful in the future of work.

Kelly Palmer is on a mission to change the way the world learns. A well-known thought leader on learning, business, and career development, she is currently on the executive team of Degreed and was formerly the chief learning officer of LinkedIn. She is the co-author of the book The Expertise Economy: How the smartest companies use learning to engage, compete, and succeed, which was named one of the best business books of 2019. Kelly speaks regularly at companies and business conferences around the world, has been featured in Harvard Business Review, the Financial Times, Fast Company, Entrepreneur, Inc, and Barron’s among others. Kelly lives in San Francisco.

Kelly book photo high res may 22 2018

What’s a book that has influenced your career or life, and why?

This may sound cliche, but “To Kill a Mockingbird” really influenced my early life as a child and then again when I was older. I remember watching the movie with my mom when I was a child and realizing for the first time that there was injustice in the world and that there were people like Atticus Finch who stood up for what was right even when so many were against him. Later in high school we read and analyzed the book and then again in college as an English major I studied it extensively. It has always held a huge place in my heart and in my thinking about life.

Was there an experience you had before age 21 that shaped who you are? What was it?

My mom was diagnosed with cancer when I was 17 and died when I was 19 and a freshman in college. I was incredibly close with her and losing her at such a young age (she was only 39) and at such a formative time in my life forever shaped my worldview and my perspective on life. For the first few years after her death, I was angry, lost, and confused, but then I was determined to embrace life’s opportunities because, after that experience, it seemed that not much in life could ever be so tragic. There is a certain strength that comes with early loss, and I think that’s influenced so much of my life.

How has a failure, or apparent failure, set you up for later success? Do you have a “favorite failure” of yours?

It’s interesting in retrospect to see what choices or events in life change the path you are on. For example, when I was early in my career, I applied for a job at Microsoft and didn’t get that job. If I had gotten that job, I would have moved to Seattle and been on a different path. Instead, I got a job at Sun Microsystems where I spent 20 years of my career, met my husband, and stayed in the Bay Area.

Later in my career when I was running a large product development organization, I interviewed for a job in a different group in engineering at Sun and didn’t get that job, but ended up going into the learning field instead. At the time, not getting those jobs seemed like huge failures to me, but over time I realized those “failures” just set me up for different opportunities in my life.

What advice would you give to a smart, driven college student about to enter the “real world”? What advice should they ignore?

I actually talk to quite a few recent college grads (my son and his friends are in that category). There is so much pressure to get a great job and be on a career path and to move up quickly, and my advice is to instead look for experiences that will help you build your skills and not focus so much on promotions and the job that pays the most money.

Those things can come over time, but if you get experiences that show that you have and are learning skills that are critical to the future of work, that’s what is going to help people be successful in the long run. For example, if you demonstrate learning agility (the curiosity and motivation to learn new skills over the entirety of your career); if you show that you can communicate and collaborate effectively; and, if you have emotional intelligence and empathy, those things will take you far in your career. Those uniquely human skills are what I call “power skills” that will make you the most successful in the future of work.

What are the bad recommendations you hear in your profession or area of expertise?

I hear executives and leaders at companies try to solve business problems by suggesting we just send everyone to a training class! It really drives me a bit crazy. We write in The Expertise Economy an example of one company wanting to send all managers, at every level, through a training class that will help them make better hiring decisions because a few managers were making bad hiring decisions. This one-size-fits-all approach does not work. Many managers already have that information and know what they should be doing, but are just not applying it; other managers may be really great at this skill already; and others may not be hiring people at all at this time, so the information is not relevant. This is not a good approach, but it’s the first thing people jump to when trying to solve a problem. As people in my profession know, this might not even be the real problem you are trying to solve.

If you could go back in time to when you were entering the workforce and give yourself one piece of advice, what would it be?

Have more confidence. When I was mid-career, I had a leader at Sun Microsystems coach me on going after new opportunities and having more confidence in my abilities and it really made a difference. I’m not sure he even realizes what an impact it made on me and my career, but I’ve tried to pass on that advice and coaching to people I’ve managed and mentored over my career. The research shows that women in the workforce feel they need to have 100% of what is needed when they apply for a job and that men feel they need about 60%. That’s about confidence in your abilities and the mindset that you will be able to do that job.

What’s one of your proudest professional accomplishments? 

For a while, I’ve had a dream of writing a business book to help impact the way people think about learning, and last year that book was published: The Expertise Economy: How the smartest companies use learning to engage, compete, and succeed. The thing I’m most proud of is the feedback I’ve been getting from people in the industry that it’s helping them in their companies move to a new paradigm in learning.

What’s something unexpected that has happened in your career, and how have you responded?

I was asked to move completely out of my comfort zone and area of expertise to integrate one of the companies we were acquiring at Sun. At first, I was thrown off balance wondering if I could actually do it. But, then I gained some confidence and got some coaching and mentoring along the way and I realized I not only could do it, but I could do it quite well. That turned into a career move to corporate strategy at Sun where I ran the acquisition integration function for all the companies we were buying at Sun.

Since entering the workforce, how have you changed or transformed?

That’s a big question since I think throughout my career I’ve been changing and transforming. Probably the biggest area where I’ve changed is that I’m more confident about working on new and interesting challenges that I haven’t tackled before and that learning about new things keeps life interesting.

What habit or practice helps you manage stress? 

I have two golden retrievers and I take them for long walks so we all get some exercise and get the endorphins going. Getting outside and walking (sort of like a walking meditation) always helps me think and reflect on both my personal and professional life and is a great way to manage stress.

Who is one person, dead or alive, who you admire? Why do you admire them? 

I just watched the documentary “Inside Bill’s Brain: Decoding Bill Gates.” What an amazing human being. When I was at Sun Microsystems he was always painted as the bad guy since Microsoft was one of our biggest competitors, but I’ve got a completely different view now. What he’s doing to try to solve some of the world’s biggest problems (climate change, world disease) is so admirable and I also admire his relationship with his wife, Melinda, and how they are working on these challenges together. While some use their fortunes for their own personal gain, he has devoted himself to higher causes and that I greatly admire.

When have you felt stuck in your career? How did you break out of it or push forward?

I felt stuck for a while after I moved into corporate strategy. I was always open to new opportunities but didn’t feel like I was necessarily doing what I was personally and professionally passionate about. That’s when I completely changed my career and went into the learning field. I thought maybe I should quit the tech industry and move into non-profit and focus on education, but realized I had no experience in either non-profit or education! Then I got an opportunity to move into an executive position at Sun to lead part of a large learning organization — the leader then took a chance on me. It was the turning point in my career and I’m forever grateful for it. I ended up going back to school to get my master’s degree while working and studied adult learning theory and education technology. It’s been my passion ever since.

For more Career Q&As, click here. Or you can check out my monthly newsletter.

You Don’t Have to Burn the Boats. Do This Instead.

In 1519, the Spanish commander Hernán Cortés arrived in the new world with grand ambitions of conquering Mexico. The story is told that before entering battle he gave instructions to destroy the ships his men had used to sail to the Americas. This audacious act sent a clear message: There is no turning back. We will conquer or we will die.

Image result for hernan cortes
Hernán Cortés, courtesy of Biography.com

This story of Cortés burning his ships has become the stuff of legend. I still remember the first time I heard it. I was in awe at Cortés’ boldness and left with the lesson that if I was to find true success, I need to go all-in and burn the proverbial boats. 

Of course, there’s something to be said of a grand act that signals to both you and others that you mean business. Burning the proverbial boats is inspiring. It’s radical. It’s courageous. But for most, it’s unwise and it’s unnecessary. 

Take Richard Branson, an entrepreneur widely viewed as someone willing to bet the entire farm to win. In the early 80s, Branson was anxious to meet his romantic interest in the Virgin Islands but his flight got canceled. He then marched to the back of the airport, handed over his credit card, and hired a plane.

Borrowing a blackboard, he wrote “Virgin Airlines one-way: $39 to the Virgin Islands” and filled up the flight with all the bumped passengers. The next day he called Boeing, shared that he’s thinking of starting an airline called Virgin and asked if there were secondhand 747s for sale. He struck a deal with Boeing and founded what came to be known as Virgin Atlantic. 

Branson’s actions were bold and audacious. We may think, “Now that’s a man willing to burn the ships and really swing for the fences!” But as it turns out, there’s more to the story. 

Branson was already the successful CEO of Virgin Records and had a lot to lose by entering the capital-intensive airline industry. In an interview with Tim Ferriss, Branson shared that the leadership team at the record company thought his idea to start an airline was crazy. They were worried he’d risk everything. 

“Look,” Branson told them, “I promise that I’ll only go into the airline business on one condition and that is if I can persuade Boeing to let me hand the plane back at the end of the first year to protect the downside. So I knew the worst that could happen would be there would be six months of the profits of Virgin Records we would lose if it didn’t work out. Boeing agreed to it.” 

We tend to think that true success requires a risk-it-all, conquer-or-die mentality. Some may take this approach, but you don’t have to. Instead, you can mitigate the risk from big decisions taking an experimental mindset. 

Let’s say you’re a financial analyst thinking about becoming a software developer. The burn-the-boats approach is to quit your job and get a master’s degree or enroll in a coding boot camp. The experimental approach is to do an informational interview with your engineer sister-in-law, read a book on programming languages, or take a free coding course. 

Or maybe you’re at a Fortune 100 company and the startup world seems to be calling you. The burn-the-boats approach is to quit your job and move to San Francisco. The experimental approach is to attend tech meetups, find part-time work at a startup, or simply take a visit to San Francisco. 

You’ll never fully escape the risk-reward tradeoff, but small tests will help you achieve the greatest reward with the least amount of risk possible. It’s about unlocking the upside while capping the downside. Little experiments give you the data you need to make the big decision. 

Cortés may have achieved success by burning his boats, but you don’t have to.

Career Q&A with Ann Hiatt, Leadership Consultant and Former Executive Business Partner to Jeff Bezos and Eric Schmidt (#5)

I recently kicked off a series of Career Q&As with successful leaders. The goal is to provide practical advice and insightful lessons you can leverage to further your career. Next up is Ann Hiatt, a leadership consultant, and the former Executive Business Partner to Jeff Bezos and Eric Schmidt. Ann offers great advice on taking career risks, trusting your intuition, and effectively managing stress.

Ann Hiatt received her initial business training during 15 years as the Executive Business Partner to Jeff Bezos (CEO of Amazon) and Eric Schmidt (CEO and Executive Chairman at Google/Alphabet). Ann now consults with executives of Fortune 500 companies as well as European and Silicon Valley startups and is on several advisory boards. Ann has recently relocated from Silicon Valley to Europe and brings with her a unique perspective on what it takes to succeed in business today and how to apply that to any organization. She is also a sought-after international speaker having spoken at conferences across five continents.

Ann is a native of Seattle and studied International Studies at the University of Washington before moving to California to begin a Ph.D. at UC Berkeley. She speaks Swedish fluently and Spanish conversationally among other European languages. In her elusive free time, Ann enjoys running, scuba diving and traveling.

ann hiatt

What’s a book that has influenced your career or life, and why?

I love anything written by Adam Grant. His book, Originals, is a favorite of mine since I’ve spent 15 years of my career surrounded by and collaborating with truly original thinkers and am fascinated by them. His insights and research really ring true for me. Also, he’s a spectacular human being. If you’re not already following him, you should!

Was there an experience you had before age 21 that shaped who you are? What was it?

My first job ever was at a startup in Redmond, Washington in 1995 (back before anyone knew what a startup was). I learned from the entrepreneur founders (who were also brothers) what it’s like to start your own company, land your first clients and grow your first team. I had no idea how much that job was preparing me for my future career at Amazon and Google and beyond. 

How has a failure, or apparent failure, set you up for later success? Do you have a “favorite failure” of yours?

I almost killed Jeff Bezos two months after being hired at Amazon in 2002. Seriously. Luckily that isn’t the end of the story or my career.  While it was the worst day of my professional life, it taught me that no matter how spectacularly you fail you always learn something. When the helicopter that I hired for Jeff Bezos crashed with him inside I learned that I am really good under pressure and with crisis management.  I just hope to never need to use that skill in that way again!  

What advice would you give to a smart, driven college student about to enter the “real world”? What advice should they ignore?

I would say to take big risks early on. Don’t be afraid to ask the “dumb” questions or to show lots of ambition.  You will never ever receive anything if you don’t ask, so be bold! I wish I had learned that lesson 10 years earlier than I did.  Oh, and max out your 401k savings contributions every year—especially in those early years. Compound interest is your best friend! 

What are the bad recommendations you hear in your profession or area of expertise?

I have been lucky to work in very innovative companies and teams. With that said, there have been times when even those people told me no when I wanted advancement. I had to trust my gut, rather than listening to advice to be happy with what I had, and push harder to find creative ways to accomplish my growth goals. Eventually, that meant taking the scary step of starting my own venture.

If you could go back in time to when you were entering the workforce and give yourself one piece of advice, what would it be?

Be bold! Aim much, much higher than you can currently imagine. 

What’s one of your proudest professional accomplishments? 

Most of my proudest moments involve creating success within impossible circumstances. At the moment that means building a 6-figure consulting business in less than a year after leaving Google—all while in a new country, language and network.  I love helping global entrepreneurs thrive!

What’s something unexpected that has happened in your career, and how have you responded?

My very first job out of university was working for Jeff Bezos at Amazon. That came very unexpectedly and literally changed the course of my life. I learned not to fear failure, to be bold, and to trust my instincts. 

Since entering the workforce, how have you changed or transformed?

When I started at Amazon in 2002 I was timid and deferential. That didn’t last long!  In order to survive in that environment, you have to be daring and confident. Those lessons served me well when I left Amazon to start a Ph.D. at UC Berkeley and then in my 12-year career at Google as the Chief-of-Staff to the CEO. Now as an independent consultant I use those skills and experiences every day with my CEO clients. I am so blessed to have learned to be proud and confident whether I’m on stage, coaching a CEO or in a one-on-one mentoring session. I still have moments of doubt and imposter syndrome, like most high performing people, but I’ve learned how to combat.

When have you felt stuck in your career? How did you break out of it or push forward?

I loved every minute of working at Google but eventually decided to leave in year 12 because there weren’t opportunities for me to grow there. I had hit a ceiling that felt arbitrary and I wanted a bigger challenge. I realized that that kind of challenge would only come if I took a leap of faith in myself and started my own company. It’s been both terrifying and very satisfying.

Who is one person you admire? Why do you admire them? 

The notorious RBG! Ruth Bader Ginsburg is a pioneer who has broken glass ceilings for so many people. She is brilliant, clever, quirky and unapologetically herself. 

What habit or practice helps you manage stress? 

I had a full-on midlife crisis a few years ago and found that exercise is my very best form of therapy. (Although I did talk therapy as well!) I find now, even when life is happy and calm again, that I need protected time every single day to move my energy out of my head and into my body.  I need the sunshine and fresh air and relentless pace to keep me grounded so that I can then do my best mental work. In true Silicon Valley form, several years ago I signed up to run a half marathon to raise money for charity before I had ever even run a 5K. I am happy to say that I completed that goal (several times over now) and felt very strong and proud at the end—which was exactly what I needed at that moment in my life. I have continued these physical challenges to myself which helps my drive and confidence in all areas of my life.

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