Three Timeless Truths Needed to Build a Great Career

Years ago I wrote a career development book. I’ve often told my kids I’d pay them $10 if they read it. My 9 year old recently decided to take me up on the offer. 

After reading it, he had a book report and needed to write 20 facts from the book. This picture is the list. He put it together 100% on his own and it cracked me up. 😂 

Some of them are funny. Yes, I did get called stupid. Yes, I had a blackberry (remember how cool those were?). Yes, Mike Robertson and I did carry a mattress on our head down Broadway for 20 blocks during our NYC internship. No comment on #13. 🤷

Others facts are timeless truths and I hope they stick with him:
1) Learning doesn’t stop when school ends
2) Networking is an important skill
3) Mentors can help you find a job and grow your career

What key lessons have you learned in your career? How are you sharing those with others?

Icarus and the Dangers of Playing It Safe

You’ve heard the Greek myth of Icarus. But there’s an essential lesson you’ve likely missed.  

Icarus’ father fashioned wings made of wax and feathers and told him not to fly too close to the sun. But he ignored that warning. The heat from the sun melted the wax, the wings fell apart, and Icarus plunged to his doom. We’ve retold this myth, and many others like it, for generations. 

All these stories have the same lesson: Play it safe. Obey your parents. Listen to the experts. Don’t fly too high.  

But there’s another part of the myth that gets glossed over. Icarus was also warned by his father not to fly too low. If he did, the ocean water would ruin the lift in his wings.  

That second lesson gets skipped but it’s even more relevant than the first. Flying too low is actually more dangerous than flying too high. Flying low feels safe. Deceptively safe. 

We hear the story of a reckless entrepreneur who flew close to the sun, plunging his company into the ground. Those who flew too high become easy targets. It’s fun to call them out. But we don’t hear about the thousands of people who flew too low. Those who played it safe. Those who never swung for the fences. Those stories happen every day but rarely get told. 

Yes, there’s danger in flying too high. But there’s more danger in flying too low. 

Don’t shortchange yourself. Don’t play it safe.

Fly high.

Career Q&A with Nolan Church, CEO of Continuum (#15)

The next Career Q&A is with Nolan Church, who is the CEO of Continuum, an executive talent marketplace. Nolan and I were peers at DoorDash and he’s one of the most talented people I’ve worked with. He’s the real deal and someone I regularly go to as a sounding board. In this Q&A, Nolan offers great advice on taking calculated risks, surrounding yourself with people better than you, and the need to constantly push yourself. I hope you enjoy Nolan’s insights as much as I did.

Nolan Church is the Cofounder and CEO of Continuum, a marketplace for executive talent. Prior to Continuum, Nolan was the Chief People Officer at Carta and the Head of Talent at DoorDash.

Nolan graduated from the University of New Orleans and was voted captain of the baseball team. He has two kids, and a wife that is better than him at everything.

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

Obstacle is the Way by Ryan Holiday. I love this book because it perfectly describes the human journey. I’ve had so many moments in the last 10 years where I’ve felt overwhelmed, overworked, and scared of the unknown. But those moments are how we grow and build character. 

I’ve read the book 5 or 6 times. Strongly recommend!

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

I received a scholarship to play baseball at Kansas State during my sophomore year of junior college. They rescinded the scholarship two weeks before my JUCO season ended.

All of my plans vanished and my world was turned upside-down in an instant. Most D1 schools had allocated all of their scholarship money (I was broke and needed financial aid to continue playing). My JUCO coach connected me w/the coach at University of New Orleans. They offered me a 50% scholarship, but I had to make a decision within 24 hours. I had never made a decision that big, that quick, with such little information. It felt like a huge risk.

I took it, and New Orleans ended up being one of the best experiences of my life. It’s not what happens, it’s how you respond.

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

I’ve failed so many times it’s hard to pick a favorite 🙂 

My college baseball team set the D1 record for losses my senior year (we went 4-50). At one point during the season, I went in a 0-27 slump. It was painful.

I realized my lifelong dream of playing professional baseball was over, and I needed to figure out a new direction. 

I re-focused on school and I got good grades. Those decisions ultimately allowed me an opportunity to crack into tech post-graduation. 

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

Two tactical pieces of advice: 1) Become a concise written communicator and 2) cold email relentlessly. These skills aren’t taught in school, but they’re essential post-graduation.

Advice to ignore: Fake it until you make it. Have confidence and be authentic, but never pretend to be something you’re not. 

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

Bad recommendations usually come from people that don’t know something firsthand, but act like they do. My rule of thumb is to only trust the people closest to the ground doing the 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?

Make your manager’s, director’s, and VP’s problems disappear. Someone gave me this advice when I first started my career, and it’s helped more than anything. 

What’s one of your proudest professional accomplishments? (while this can include an obvious accomplishment, feel free to include a more personal one)

Starting Continuum. There are very few VC-backed founders with a People Ops background, and I’m proud to be one.

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

In 4 years, I went from Recruiter, to Head of Recruiting, to Chief People Officer, to Founder. The amount of growth I went through — and continue to experience — in order to keep up the demands of my role(s) was/is insane. 

Early in my career I was constantly stressed. With time I came to appreciate that growth is supposed to feel uncomfortable. Now, I’m trying to enjoy the ride and have more fun.

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

As a kid, my parents always hated their jobs. They thought work was a necessary evil. It took me a few years post-college to realize that work could be fulfilling, fun, and a healthy part of my life. 

I learned that work becomes magical when you fall in love with what you’re building and who you’re building with. Life is short. Only work on things you’re passionate about.

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

I hit a learning plateau after my first 2 years at Google. Nobody around me was pushing to get better, grow, or do big things. It was a very complacent culture.

I realized that I was playing it too safe. I needed to take a risk and push myself outside of my comfort zone. I left to join an early-stage startup (DoorDash), and I haven’t stopped growing since. 

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

Teddy Roosevelt. I have the ‘Man in the Arena’ speech on my office wall.

Roosevelt experienced significant adversity. His wife and mother died on the same day. His son died in WW1. He became the youngest president after McKinley was assassinated. 

Yet he kept pushing forward. He’s remembered as a trust-buster and conservationist. He’s a model of perseverance. 

What habit or practice helps you manage stress? (the more specific you can be, the better)

Working out every day. Usually running (HIIT sprints on the Peloton Tread) 2-3x/week, strength training/climbing 3x/week, and yoga 1-2x/week. It’s the only way I stay sane.

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

Career Q&A with Whitney Johnson, CEO of Disruption Advisors (#14)

The next Career Q&A is with Whitney Johnson, who is a CEO, author, investor, and executive coach. I’ve known Whitney for many years and she is one of the most gracious, intelligent people I’ve met. Whitney offers exceptional advice on the power of taking initiative, why everyone should get a coach, and how you can disrupt yourself to find career success. I hope you enjoy this Q&A as much as I did!

Whitney Johnson is the CEO of human capital consultancy Disruption Advisors, an Inc. 5000 2020 fastest-growing private company in America. Having worked at FORTUNE 100 companies, been an award-winning equity analyst on Wall Street, invested with Harvard’s Clayton Christensen, and coached alongside the renowned Marshall Goldsmith, Whitney understands how companies work, how investors think, and how the best coaches coach.

Whitney is an award-winning author, world-class keynote speaker, and frequent lecturer for Harvard Business School. She is a frequent contributor to Harvard Business Review and the author of bestselling books Build an A Team and Disrupt Yourself. She also hosts the weekly Disrupt Yourself podcast whose guests have included John Mackey, Brené Brown, Stephen M.R. Covey, and Zaza Pachulia. Whitney is married, has two children, and lives in Lexington, VA. (See full bio here.)

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

The Innovator’s Dilemma by Clayton Christensen. His theory of disruptive innovation––a Goliath-like legacy business could be overtaken by a silly little David––changed my thinking as a Wall Street equity analyst. It also revolutionized my thinking about growth. In 2004, I had been an award-winning equity analyst for nearly eight years. I loved it, but I felt like there was something more.

After an especially discouraging conversation with my manager, who wanted me to stay right where I was, I had a flash of insight. My current equity analyst self was the incumbent––Goliath. My future self was the upstart––David. To take up the giant, I had to disrupt myself. It was revelatory. Disruption wasn’t just about products, it was about people. As I write in the dedication to my latest book, Smart Growth: How to Grow Your People to Grow Your Company, “To Clayton Christensen, who made this S Curve possible.”

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

When I was three years old, after seeing The Sound of Music, I picked out Do-Re-Mi on the piano. I studied music throughout my childhood, and eventually majored in music. Piano practice brought discipline, accompanying vocalists and/or instrumentalists taught me to be attuned to others which informs my coaching, and the general sense of musicality informs my writing and speaking. Once, after a speech, I had an audience member say, “I felt like I was listening to you play an instrument.” Best compliment ever.

How has a failure, or apparent failure, set you up for later success?

A few years ago, I delivered a keynote. The audience didn’t like it, they hated it––I have the comment cards to prove it. Because of nerves, I was focused on myself, not attuned to the audience. I had become the hero (like the accompanist who thinks they are the star). And if I was the hero, then who was the audience? It was my job to be the guide so the audience could be the hero.  This was the wake-up call that made the ‘musical moment’ experience possible, the failure that led to a success. For more on failure, listen to our Disrupt Yourself podcast, Episode 200.

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

Take initiative. Take initiative. Take initiative. Look for what you think needs to be done. Tell your boss what you plan to do and ask for input. Ask Does that work for you? If you are competent, and take initiative, you will quickly be labeled a superstar.

Also, take advantage of the fact that you are straight out of college. When a twenty-something asks me a thoughtful question––I will try to say ‘yes’ simply to reward you for taking the initiative. In general, those over 40 feel the responsibility to feed our young. Being in your 20s has its privileges. Use them before they expire. 

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?

Get a coach. Straight out of college I was getting the training that I needed to do the functional job, but I had no idea how to navigate the emotional job that I was being hired to do. I read a lot of books, but a coach could have helped me move up my S Curve of Learning faster. 

What’s one of your proudest professional accomplishments? 

I am proud of the fact that I disrupted my mindset about what was possible for me. When I graduated from college, I had a music degree, no idea what I wanted to be or do, except some vague notion that I would have children (was already married), and not a lot of confidence. That I was able to change how I was thinking about myself and move from being an EA to an investment banker, which rarely happens in financial services (still!). I am proud of that. (And grateful that I had a boss who believed in me and made it possible.)

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

I didn’t expect that one of my superpowers would be to apply business theories or concepts to the individual, like I have with both disruption innovation and the diffusion curve. Nor did I expect that the S Curve of Learning would be such a useful model for helping people think about what growth looks like. My response––instead of this being in the background like it was in Disrupt Yourself and Build an A Team, it is the hero of the story in Smart Growth.

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

According to Jungian psychology, we have both masculine and feminine characteristics. The ability to get things done, to wield power is considered masculine, while to love and be connected are considered feminine traits.. To truly grow up, both men and women need to develop both. While home and family has been the vehicle for me to develop feminine characteristics, work has helped me develop masculine traits. It has been an important vehicle for helping me grow up.  Note: I write about this in detail in my first book Dare, Dream, Do: Remarkable Things Happen When You Dare to Dream.

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

When I was pregnant with my first child, my boss was fired. They probably would have given me the boot too, except that I had good performance reviews, and I was pregnant. I interviewed for a number of roles in investment banking, but there wasn’t a fit. Desperate, they pretty much shoved me into equity research. Once I got to research, there was a merger, and with it came a highly-rated analyst who covered the sector (cement and construction) that I was supposed to cover. I had now been disrupted twice. 

My only way out was a third round of disruption, but this time disrupting myself. There were a number of media companies going public and no one to cover them. So, rather than trying to knock on a cement door that was closed, I built my own door. I became a media analyst. By building a door for myself, I built a door for my company. My way through was personal disruption. 

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

Joan of Arc––I’ve been reading Mark Twain’s autobiography of her––she was so clear on her purpose and so courageous.

Diana Krall––I admire her musicianship and her voice––and how she didn’t start singing until she was in her late 20s because she thought she didn’t have a good voice.

What habit or practice helps you manage stress?

Exercise, running specifically, helps release the cortisol that builds up due to stress (whether good or bad stress).

Gratitude. Stress often comes because of a perceived danger––specifically that I won’t be able to get done what I need to do in the time that I have to do it. And ‘the wild bear will catch me and I will die.’ If, in that moment, I become hyper focused on what I am grateful for, my ‘upstairs’ thinking brain can signal to my ‘downstairs run away NOW brain’ that I’m not actually in danger. Which relieves the stress. And allows me to get done what I need to do in the time I have to do it.

Do the thing that I am avoiding which can lead to anxiety which leads to a stress response. If I am anxious about something (back to the wild bear), I might procrastinate, or avoid it, and then my brain will feel relief. Something I’ve learned from psychologist Emma McAdam is that in the moment my brain will reward me. Good job, you escaped the bear. But then when there’s another bear of a deadline, then my brain tells me to avoid it again. This creates an anxiety loop. So do the thing I think I can’t do––that’s making me anxious, that’s causing a stress response––now.

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

How to Create a Life Worth Living: Interview with Kevin Delaney, VP of L&D at LinkedIn (Episode 18)

In this episode, I interview Kevin Delaney and dive into his book, A Life Worth Living: Finding Your Purpose and Daring to Live the Life You’ve Imagined. Kevin is a VP at LinkedIn where he leads Learning and Development. Prior to that, he was an HR exec at VMware and several other companies. He’s a former colleague of mine, and someone I consider to be a mentor and friend. 

In our conversation, we discuss his lessons from a serious health challenge, his approach to balancing annual planning with daily rituals, his unique perspective on dealing with setbacks, and, of course, how to create a life worth living. Kevin is one of my all-time favorite people and someone who truly walks the talk. I hope you enjoy our conversation.

You can read Kevin’s book here

The Most Important Story You Will Ever Tell (Episode 14)

Click here to listen to the podcast version

The most important story you will ever tell is the story you tell yourself.

I’ll say that again, the most important story you will ever tell is the story you tell yourself. 

One of my professors, Curtis Lebaron, shared this with our class many years ago. I didn’t fully know what he meant at the time, and I’d like to explore it further today. 

The stories we tell ourselves start at a young age. We love labels. Our society loves labels. In high school we label people as jocks, or we label people as nerds. When I was in high school there was a group that dressed in all black. We called them goths. Not sure if that’s still a thing. 

Why do we label? Labels make it very easy to categorize things. Labels make a complex world appear simple. Labels allow us to tell easy stories. But labels can be very dangerous. We know the danger of applying inappropriate labels to groups of individuals–we call these stereotypes–but have you stopped to think about the danger of the labels you apply to yourself? Have you thought about the story you tell yourself about who you are? 

I’ll share a personal example. Throughout most of my life, I have told myself the story that I am not creative. I was never fond of drawing or painting. Art class never was fun. Part of the reason is that I’m color blind. In 2nd grade I had a very traumatic experience where I was made fun of by my teacher and classmates for being color blind. In front of my class I shared a picture of my “green frog” but I had colored it brown. Everyone laughed at me.

I told myself: I am color blind. I don’t like art or drawing . Therefore, I am not creative. That story, which was repeated regularly, turned into a fixed mindset towards all things creative. Whenever an assignment in school came up that required creativity, I shied away from it. I told myself, I’m just not a creative person. That’s not me. 

This story stayed with me until I joined LinkedIn on the compensation team. I had a few projects I was leading and my manager pushed me hard to be creative. I still remember when he used that word. It was like fingernails running down a chalkboard. I didn’t tell him, but in that moment I thought, oh no, that’s not me. 

My manager and I had several conversations on the topic of creativity. I decided to give it a try, so I read a lot of articles and a couple books on the topic. My favorite book was Steal Like an Artist from Austin Kleon. I highly recommend this book and it helped shift my perspective on what creativity is and super practical ways we can be more creative. 

As time went on, I changed that story. By trying to act in a way that was creative, and by telling myself that I can be creative, a virtuous cycle was forming. I was becoming more creative. The change didn’t happen overnight but I made consistent progress. 

Over the next year, I wrote a book–something I had never done before– learned to edit video, learned how to market a book, and developed several other skills. 

Back to LinkedIn–I later left the compensation team to join another group that was highly analytical. We were working on a large data integrity initiative and my team was tasked with coming up with a creative way of making it stick. One person in the group said–I’m not creative. You’re the creative one. What should we do? I was tempted to say that I’m not that creative either but I owned it. I had been labeled as someone who was creative, which was in line with the person I was trying to become, and I wasn’t about to ruin that.

The lesson for me was that if you don’t like the story you’re telling yourself, you can change it. As I wrap up that example, I’m tempted to add that I still don’t feel like I’m very creative but I’m not going to say that. I can be creative and the more I work at it, the more creative I will be.  

This example focuses solely on creativity, but the stories we tell ourselves can cover anything. You might be upset with your spouse because he was rude to you or didn’t clean up his messes for the last few days. Another person might have the same experience but tell themselves a story about how her spouse has been working hard at his job, has gone out of his way to cook a nice meal for you, and is tired and needs some comforting.

Here’s the challenge for this episode — start to notice the story you’re telling yourself about everything. Your boss was late again to your 1:1. Does that really mean she doesn’t care about you? Your colleague has been dragging their feet on a project. Does that really mean they are incompetent 

When you catch yourself in this way of thinking, pause —- then say, the story I’m telling myself is ______. What’s a different story I could tell? 

Stories are incredibly powerful. They shape how we view the world and how we view ourselves. Always remember that we have the power to rewrite our stories. We have the power to change.

Career Q&A with Heather Hatlo Porter, Chief Communications Officer at Chegg (#13)

The next Career Q&A is with Heather Hatlo Porter. Heather offers exceptional advice on how mentors can help us get unstuck, how failure can be a career accelerator, and how to find the courage to seize opportunities that may initially intimidate us.

Heather is Chegg’s Chief Communications Officer, leading all internal and external communications efforts for the company. Previously, as VP of Marketing, she was responsible for building Chegg’s brand narrative, creating innovative campaigns with major influencers, and spearheading cause-marketing efforts. Her passion for the mission inspired her to help launch the Chegg Foundation in 2013, later transitioning it in 2019 to Chegg.org, the new social impact, grant-giving and advocacy arm of the company that elevates the student voice through policy efforts such as the “Unlocking The American Dream” student debt policy report.

When she is not focused on putting students first at Chegg, Heather is focused on her own students, her two sons, and can be found cheering at the ice rink for her kids as a devoted hockey mom or volunteering with local organizations as a passionate community member.

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

My very first job, in high school, was a courtesy clerk for Nob Hill Foods. And, it wasn’t so much the work or the role that had a profound impact on me, but it was the lessons I learned from the leadership team there.

Back then, I was going through some challenging times in my personal life, and I will never forget how caring and supportive the management team was. On the days when I couldn’t make it to work, because of one reason or another, or on the days I showed up late, they met me with such compassion and understanding.

When so many employers would have seen a flighty 17-year-old girl who wasn’t fulfilling her obligations to the job – which certainly should have led to getting fired – they took the time to ask what was going on and inquire as to why my schedule seemed so unpredictable. They got to know me and, through that, were able to show a level of compassion I never expected from “the big bosses”. In fact, during a particularly rough spot in my life, one of them even offered to let me stay with their family temporarily. Thankfully, that wasn’t necessary but just the thought that someone who I worked for would do that for me had a deep impact on how I think about my own employees today.

I have learned to really prioritize getting to know what is going on in people’s lives outside of the four (virtual) walls at Chegg. By understanding where they are coming from, what they are experiencing, what challenges they might be facing, I can do a better job of supporting them in their work. Quite frankly, I treat them like they are family because I think that’s the best way to bring out the best in people. I always start team meetings by asking how they and their families are doing so I know how to support them in any way they may need.

Giving your employees grace, encouragement, and understanding creates a culture where they know they can trust you to lead them to grow and succeed. When a person feels cared for and supported, they are much more likely to be fully invested in their work and deliver superior work at that.

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

I have failed many times; I am not sure where to start! Some of the marketing campaigns that I thought would be phenomenal over the years ended up falling flat. I learned afterwards that these campaigns failed not because the idea and execution were lacking, but because the audience’s appetite for it simply wasn’t there. The biggest takeaway from all these failed campaigns is to always research before executing an idea and to find out what the audience actually wants. Assumptions are great, but data is better.

At Chegg, we have an entire research team dedicated to surveying students’ needs and wants, and we deep dive into the survey results to create products and services that benefit them the most. Along those same lines, I really value our interns’ feedback every summer because they are much closer to our target demographic than I am, and some of my ideas have been shot down by them for being irrelevant or outdated (and let me tell you, sometimes that makes me feel so old!). What this has really ingrained in me as I have progressed throughout my career is to do my homework, identify what it is I am trying to accomplish, understand if it is big enough to matter, and then make sure I know how we would define success for whatever it is we are working on.

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

My advice for students is to go easy on yourself. Like most other college students, I used to experience a lot of self-doubt and anxiety about my future. I felt rushed to land the perfect job and enter a relationship, putting way too much pressure on myself about every decision I made in my early twenties.

Looking back now, I realize that my career path looked nothing like I expected but, each step along the way, I learned invaluable lessons and I honestly wouldn’t change a thing. I know many young people, especially at this time, are feeling very uncertain about their future amid a global pandemic and economic uncertainty. I think now, more than ever, it is particularly important to take time to invest in your mental health and well-being and give yourself permission to not have all the answers, to not know what comes next, and to be okay with that.

So, I guess on that note, the advice I would say to ignore is the old mantra of “fake it till you make it.” Don’t fake anything. Be authentically you, don’t stress too much about the future, and know that life is a journey and some of my best moments came out of the times where I had no idea what was going to happen next. 

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

I have been given several unexpected opportunities throughout my career, opportunities that I did not have the skill set nor the experience for at the time. But I had the courage to seize those opportunities, and ultimately, I used these experiences to build up my confidence.

I knew I was great at being an executive assistant, so I was hesitant at first when the opportunity to join the marketing department came up. I knew I wanted a change, but I didn’t know if I would be successful at it. So much so that I told my boss at the time, “let’s just try this for six months” fully expecting her to fire me at the end of that test. 7 years later, under her mentorship, I was the VP of Marketing. I could never have predicted that but because I took a chance on something that scared me, it opened even more doors which, eventually, put me on the path to becoming Chegg’s first CCO.

I think being able to articulate what it is I want to do and, equally as important, knowing what I don’t want to do, being willing to take risks, and embracing failure has really helped me excel through my very non-traditional career path.

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

Well, I started working full-time at 18 so I have grown tremendously over the course of my career in so many ways. I think one of the more obvious places of growth is that I had to learn how to accept not being good at things, at failing, and being transparent about that. Early on in my career, I thought that failure was not an option and that it would be catastrophic for me professionally. Now, my attitude towards failing is the exact opposite. I learned that failure can be a career accelerator because of the learning opportunities you get every time something doesn’t work.

In fact, Esther Lem, Chegg’s CMO and one of my mentors, really modeled that for me by celebrating failure every month in our marketing team meetings. She gave failure a central point in our team meetings, allowing people the opportunity to talk about the lessons they learned and so that others could see the failures across the team. These meetings taught us to take ownership of our failures and to be empowered, rather than hindered, by them. 

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

I was an executive assistant for ten years. By the age of 30, I had reached the top of the career ladder for that role, having already worked for the CEO and Chairman of the company. I didn’t know what I wanted to do next and felt stuck in terms of professional growth. I actually tried to resign from Chegg because I thought there was nothing more for me.

Fortunately, another one of my amazing mentors, Dan Rosensweig, encouraged me to explore my other interests, such as philanthropy and creative storytelling, and recommended I give marketing a shot because it seemed like a fitting pivot in my career. It was like a lightbulb went off because I had never connected my degree, which was focused much more on creative storytelling for film or theater, to brand storytelling. He was able to offer me a perspective I wouldn’t have even considered on my own.

So, when you feel fatigued or lost or just that you have reached a plateau in your career, I think the first step is just being self-aware. I knew when I was at the end of one path. I just needed some guidance about finding my next one.

And, on that note, I think surrounding yourself with great mentors is really important because they can challenge you in ways that might surprise you. And then, when the opportunity to make a change presents itself, you have to be bold enough to take the risk at trying something new. When that door opens, ignore that self-doubt and just go for it.

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

I feel like, on any given week, I would have a different answer to this question because I admire so many people for so many different reasons. I look up to the many amazing female mentors I have in my life, like Esther Lem, Lee Woodruff, Desiree Gruber, and Melanie Whelan. Right now, I am really in awe of Arlan Hamilton, because she is transforming the venture capital world.

I started my professional career in the corporate legal environment and then moved into private equity. But, unlike my peers at the time, I did not have a master’s degree from an Ivy League school. In fact, I attended community college, transferred to a local state school, and did not pursue a higher degree afterwards and, because of that, for a long time I felt like I was always underestimated. It weighed on me a lot but also made me work much harder than everyone else around me. I always felt I had to hustle to prove my worth.

Arlan seems to have a similar mentality. She experienced so many setbacks but has still shown the world that it doesn’t matter where you came from or what your background is. What matters is where you are going and your ambition to get there. I admire how she hasn’t let anything hinder her success and how she stays focused doing what she is passionate about and having such a positive impact on the people and communities around her. She’s a rock star.  

What habit or practice helps you manage stress?

I find I have to invest in both my physical health and my mental health to really find balance in my life – especially these days. I make it a priority to find time to work out, even if that just means a walk with my kids or the dog, or a quick HIIT workout if I am short on time. It’s really evident, to everyone around me, when I don’t have any exercise in a given week. Let’s just say, I don’t even like being around myself then.

I also find connecting with my family and friends to be a great stress-reliever. That’s been particularly challenging during the COVID-19 pandemic, but I have been finding creative ways to spend time with people, such as hosting Sunday family suppers over Zoom and playing online games or doing virtual wine tastings with friends. It is important for me to feel connected with my friends and family, and I’m so grateful for the technology that enables us to do so.

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How Lifelong Learning Will Give You a Competitive Edge (Episode 10)

The days of going to school, getting a degree, and being done with your learning at graduation are long gone. If you’re banking on what you learned in high school or college to carry you throughout your career, you’re in for a rude awakening.

The workplace is more dynamic than ever and new technology is accelerating that change. To thrive in today’s world of work we must constantly learn and constantly grow. 

So, what do we do? In this episode, I share three concrete ways you can make learning a competitive advantage in your career. I also share the future of The Not Your Parents’ Workplace Show including why I’m going to hit pause on YouTube and why I’m doubling down on the podcast. 

Alexander Hamilton and the Art of Discretion (Episode 11)

For the podcast version of this article, visit Apple, Google, or Spotify Podcasts

I first read Ron Chernow’s biography of Alexander Hamilton in 2014, having previously studied the lives of his contemporaries, specifically, George Washington, John Adams, and Thomas Jefferson. I had a glimpse into his life and how many historians remembered him, but Chernow’s account totally opened my eyes.

This man was far more than the first treasury secretary of the United States. His accomplishments include:

  • Supporting Washington as his chief staff aide during the American Revolution and commanding three battalions during the decisive battle of Yorktown
  • Architecting the Federalist Papers which played a pivotal role in defending and ratifying the U.S. Constitution (he wrote 51 of the 85 essays)
  • Founding a national bank and building the financial system that established the country’s credit
  • Creating the U.S. Coast Guard and the New York Post

Born in Nevis, a small island in the Caribbean, Hamilton’s father left him when he was a boy. Not long after, his mother died of yellow fever and his cousin, who was entrusted to watch over him, committed suicide. Without a doubt, of all the founding fathers, Hamilton’s rise to power is by far the most improbable.

Over the years my admiration for him only grew as I watched Lin Manuel Miranda’s musical and studied more of his life. A few months back, I decided to tackle his biography once more. The biggest lesson from reading this book, at least as it came to a close, is that of discretion.

Hamilton was a genius. Full stop. Yet, despite being a genius, or maybe because of it, he didn’t know when to keep silent. He spoke his mind at all times and this came back to hurt him on countless occasions.

In a letter to his son, sent days before his fatal duel with Aaron Burr, Hamilton wrote that he had “prepared for you a thesis on discretion. You may need it.” Here’s a portion of the letter.

“A prudent silence will frequently be taken for wisdom and a sentence or two cautiously thrown in will sometimes gain the palm of knowledge, while a man well informed but indescreet and unreserved will not uncommonly talk himself out of all consideration and weight.”

To quote Chernow, “This…sounds like the confessions of a man who had never learned to be discreet himself.” It’s been said that all advice is autobiographical, and Hamilton must have been talking to himself in a way, reflecting on times where his indiscretion had harmed him.

The dictionary provides two definitions of discretion:

  • The quality of behaving or speaking in such a way as to avoid causing offense or revealing private information
  • The freedom to decide what should be done in a particular situation

One can argue that had Hamilton shown more discretion throughout his life, had he behaved or spoken in a way that avoided causing offense to others, he wouldn’t have left behind such a long list of impressive accomplishments. Possibly, but a few moments of discretion could have spared him the hatred of many, and likely would have saved his life.

And what of Aaron Burr, the man who shot and killed Hamilton in their infamous duel? Burr was the antithesis of Hamilton. He rarely revealed how he felt on a given topic. He had the well-earned reputation of doing whatever was politically expedient. Burr was hard to read and many struggled to know where he stood.

Yet, as odd as it sounds, Burr ultimately paid a price for having too much discretion. Years of concealing how he felt and striving to be all things to all people took a toll. He finally reached the point where he couldn’t hide his true feelings towards Hamilton anymore and he lashed out. He had let his anger and hatred for Hamilton fester until he reached a boiling point and couldn’t hold back any longer.

Despite being the Vice President of the United States, Burr unleashed his rage and challenged Hamilton to a duel. He felt that Hamilton had defamed his character and had sought to destroy his political career. While he had plenty to lose from going after Hamilton, there was no turning back. Burr’s rage had consumed him.

Ironically, it was Hamilton’s death, rather than Hamilton’s verbal assaults, that led to Burr’s political undoing. After the fatal duel, Burr’s career was never the same. Facing potential murder charges, he fled to the South. He later faced treason charges for conspiring to plan the secession of several western states. So, he moved to Europe and didn’t return to New York until after his acquittal. His professional and personal life remained in tatters until his death in 1836.

It’s easy to point out the foibles of leaders who lived 200+ years ago. It’s harder to take those learnings and apply them to our lives to further our own development.

I invite you to consider the role discretion plays in your life. Are you like Hamilton, committed to speaking your mind at all times regardless of the occasion? Or are you more like Burr, constantly concealing your feelings, unwilling to share what you genuinely think until you reach a breaking point?

Much later in his life, reflecting on the duel, Burr remarked, “I should have known the world was wide enough for Hamilton and me.” Had he been willing to confront Hamilton earlier, had he been a little more indiscreet, they likely could have settled their differences peacefully and without violence. Conversely, had Hamilton been a little more discreet, had he effectively discerned when to maintain silence, his life likely wouldn’t have been taken at age 47.

The world certainly was wide enough for Hamilton and Burr.

As we move forward in our careers, I hope the lesson of these two men stay fresh. Discretion truly is an art.

Difficult Conversations: Why They’re Important and How to Have Them (Episode 9)

Too often we avoid having difficult conversations because we tell ourselves it’s just not worth the effort. Nothing will change.

We tell ourselves that our manager or whoever’s involved doesn’t care about us and that there’s no point in speaking up. Often it’s easier, and quite frankly safer, to believe these things rather than to take action.

While no one likes having difficult conversations, when we avoid them, we trade short term discomfort for long term dysfunction.

In this episode, I share why it’s critical to have hard conversations, a framework for guiding these discussions, and three tips that will ensure you’re successful in having them.

As a reminder, The Not Your Parents’ Workplace Show is now available as a podcast. Please consider subscribing and leaving a review on Apple.