How Constraints Unlock Creativity (Interview with Kyle Fackrell, Creator of Space Race)

When COVID hit, Kyle Fackrell, had to hit pause on the musical he was creating. Thankfully, this gave him space to make Space Race, the hit musical series now available on YouTube.

Space Race is literally a one man show where Kyle did all the writing, composing, singing, acting, and editing. If you haven’t seen it yet, you are missing out. In this conversation, Kyle discusses his creative process, reveals how Space Race came about, and shares how constraints unlock creativity.

This interview is available on YouTube and as a podcast.

Watch Space Race

Follow Kyle on Facebook

Kyle’s home page

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.

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

Career Q&A with Luke Mocke, Co-Founder and CEO at Mentorli (#12)

The next Career Q&A is with Luke Mocke. Luke offers great insight into overcoming setbacks, why your job search is NOT a numbers game, the downside of the LinkedIn cafe (!!), and why he decided to start Mentorli.

Luke Mocke is a South African born entrepreneur. After years in the Bay Area at LinkedIn, he cofounded the #GetHired Summit to combat unemployment during the pandemic, and Mentorli to equal the playing field for underrepresented talent. Prior to his career in talent, Luke was a rugby player, winning 3 national championships with BYU and representing the United States as an All-American. He now lives with his family in Lehi and plays an integral part in the Silicon Slopes startup ecosystem. 

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

After growing up in South Africa, I played a season of rugby in the US. I was 19 and up until that point hadn’t thought much about my future – certainly didn’t have big dreams or ambitions. Seeing how people lived here and how people from my community had come over and done incredible things opened my eyes to life’s possibilities and my potential. Also happened to meet my wife on that trip – fortunately punched way above my weight category with a strong foreign accent 😉 

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

I was lucky to play on a fantastic rugby team in college – we won the national championship for my first three seasons only losing one game. We were on track to do the same in my senior season and ended up losing in a gut wrenching final where Berkeley came from behind to snatch it. I was wrecked for weeks. Although I would still choose to win that game, I’m grateful for the humble pie I was dished. It helped me roll with the punches and step into my role at LinkedIn post-graduation with more meekness. I had a growth mindset that I wouldn’t have had otherwise. 

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

David & Goliath by Malcolm Gladwell. I was fascinated by his perspective of weakness and success.

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

Anyone telling you your job search is a numbers game doesn’t know what they’re talking about. Run for the hills when you hear this – then decide what’s most important to you and look at opportunities with that lens. Go deep. 

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? 

Don’t eat so much at the LinkedIn lunch buffet. 

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

It was all about me at the beginning. I’ve realized that I’m most happy serving others so I’ve shifted my efforts to helping as many people as I can. It’s far more fulfilling and I believe this mindset breeds success too. If I’m not financially successful in the end, well hey – I’ve been able to help tons of people and that feels great! 

So what is Mentorli?

If you want to land a job at Google, Facebook, LinkedIn, or at a fast growing startup like Podium, Lucid, or Doordash, you NEED someone on the inside to refer you to open positions and champion you to hiring managers. Mentorli connects top diverse talent to employees that mentor, refer, and champion throughout the process. Backed by RevRoad and BUILD Impact Fund, Mentorli is pioneering the most effective methods to create an equal playing field in recruiting. 

Why did you decide to start a company?

From my great grandfather building a farm literally from nothing, to both my parents owning their own small businesses at various times while I was growing up – creating is just a part of me. It’s in my blood. A better question is why did I start THIS company. I started Mentorli because I care deeply about helping others improve their career. New worlds have been opened to me by way of my mentors so, knowing what I know now, I want to use my experience to level the playing field for folks looking for their next play. 

What habit or practice helps you manage stress? 

Stress never affected me negatively until I started a company. Then it came like a wave could never have expected. Planning nightly for the following day has helped me feel less overwhelmed about the day and being outside every day has been a game-changer. That seems crazy to say but I went through stages where I wouldn’t leave the house because I was working so much. Now, as a rule, I exercise every morning or take a walk outside every day – helps a ton! 

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

How to Neutralize Anger in Others (Episode 13)

Back in Episode 8, I shared a simple tool to control your own anger. But what do you do if others are mad at you? How can you neutralize that anger and get them to a more rational state of mind so that you can solve the problem?

In this episode, I share how you can do just that. 

A few years back I had a meeting with an employee that I was dreading. I’ll spare the details, but he was frustrated about his compensation and felt like he had been wronged. He had spoken about this with his manager and HR business partner on multiple occasions. Still not satisfied, he reached out to me over Slack. 

I walked him through the situation, the various factors at play, and why we made the decision we did. And I told him that we would not be revisiting that decision. I thought that would be sufficient, but, undeterred, he asked if we could meet in person.

Given that I had little to lose in this meeting (he was likely going to be angry at me regardless of what I said), I tried an approach I learned while reading Chris Voss’ book, Never Split the Difference. Voss taught that you can neutralize angry people by identifying the worst things the other party could say about you and say those things before the other person can. These accusations often sound exaggerated when said aloud, so speaking them will encourage the other person to claim that quite the opposite is true.

So, back to this employee meeting… I walk into the conference room and he’s already there, waiting for me. I can tell that he’s heated. Before he could say anything I blurted out, “Listen, I know you’re pissed off about this situation and how you’ve been treated. You must think I’m a total jerk.” His whole demeanor shifted. He responded by saying Oh no, I’m not mad, I just want to understand why you made the compensation decision. His anger was diffused and we were both now ready to discuss the problem. I walked through the rationale for the decision and after a few minutes the conversation came to an amicable close. 

I think one of the reasons this approach is effective is that it shows the other person that you know what they’re experiencing. Acknowledging how they may be feeling shows empathy. It makes them feel listened to. It makes them feel heard. 

But be careful. I’ve seen this approach used ineffectively. I’ve seen it blow up. It’s critical that you do this authentically and that you actually show empathy. If this approach is done flippantly or used excessively, it will lack authenticity and may make the other person even angrier.

Thank you so much for listening! If you like this episode, please subscribe to “The Not Your Parents’ Workplace Show” and rate and review wherever you get your podcasts.

Career Q&A with Tami Forman, Chief Executive at Path Forward (#11)

The next Career Q&A is with Tami Forman. Tami offers great insight into the power of setting low expectations (yes, you read that right), how our obsession with “passion” can lead us astray, and how having a child helped give her confidence in her career.

Tami M. Forman is the chief executive of Path Forward, a nonprofit organization that creates mid-career internship programs to ease the transition back to work for women (and men) after taking a break for raising children or other caregiving responsibilities. Before founding Path Forward, Tami spent a decade as a tech marketing executive with data solutions provider, Return Path. Before that she worked in book publishing at Simon & Schuster and Houghton Mifflin and held senior-level web editorial positions at iVillage and News Corporation. She is a frequent speaker on issues related to women’s participation in the workforce, writes a career column for Forbes, and was named by Flexjobs as one of the top 20 career experts for working moms. Tami lives in New York City with her husband and two kids, aged 10 and 12. 

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

I am a big fan of Laura Vanderkam, especially her book on working women titled I Know How She Does It. She offers different ways to think about our relationship to time which, especially in a knowledge job, is really helpful for breaking out of old habits around work and life. I don’t believe women or men should have to choose between a fulfilling career and a life. Vanderkam’s work offers frameworks that help you figure out how to make that idea a reality. 

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

My parents are not college graduates so, for me, college was a very disorienting experience. It was very apparent to me that many of the kids around me had access to a set of unwritten rules and practices that I had to figure out. And that carried over when I entered the corporate world. Because my parents didn’t have professional jobs I am not a native to the folkways of corporate culture. Much like an immigrant to a new land I’ve had to learn the customs and language without the benefit of having grown up in it. I think it’s made me resilient and given me the confidence to take a leap into the unknown—I know I can figure things out.

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

I started out my career in media—book publishing and then digital media—and I didn’t do great in that field. Part of it was loving books and writing is not enough to carry you through a career. But also, it was a world I just didn’t fit into. Part of it was being a corporate “immigrant”—I didn’t understand how the white-collar world worked in general. But media, specifically, is an industry where a lot of emphasis is placed on where you went to school, what neighborhood you live in, and what connections you have. Some people are able to overcome that and find a way to fit in—or find a way to stand out!—but I couldn’t really do either of those. Took me awhile to figure out that it just wasn’t the right fit. 

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, “Just start somewhere.” So many of us starting out want to pick the “right” job to lead to the “right” career but there’s no way to really know if you are good at something or will like it unless you start doing it. Take a job that seems aligned with your interests and then go from there. I generally tell people to ignore the advice to “Find your passion.” If you really have a passion you will know it and you really won’t even have a choice but to follow it. But most of us have a lot of different interests and could fit well in any number of careers. Our obsession with “passion” can lead people down dead end roads. 

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

Along the same lines as “find your passion,” I really hate when people say “Do what you love and the money will follow” and “Love what you do and you will never work a day in your life.” First, there are lots of things people love doing that simply do not pay well. Second, I love my job and there are days that are hard and awful. Work is still … work. Expecting to love every minute, and get paid handsomely for loving that super gratifying, totally fulfilling work, is just setting people up for massive disappointment.

I believe in keeping relatively low expectations. You can have big goals and still not have such ridiculous expectations that you are almost guaranteed to be disappointed. By the way, this is also where I think my upbringing helps me out. I have already far exceeded all expectations I could have imagined for my life—at this point everything is really gravy. 

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? 

“Your first job won’t be your last job.” I knew that, of course. In 1993 there was no longer an expectation that you’d spend your whole career at one company. But I still think I was too worried about making a bad choice. I wish I’d embraced the idea of exploring different jobs earlier in my career. The idea of design thinking—trying something, figuring out what is working and what is not and then tweaking—is something I came to later. But if I’m being kind to my younger self I have to admit that it’s easier to feel comfortable with the idea of experimenting when you have had some success and seen things work out!

What’s one of your proudest professional accomplishments? 

I’m really proud of starting Path Forward from scratch. We’ve now worked with 70 companies, including large employers like Walmart, SAP and HPE, we’ve seen more than 400 people employed through our returnship program and we’ve truly established ourselves as experts in our part of the workforce development space. And everything I’ve done in the last 4.5 years is something I had never done before which makes these accomplishments feel even more incredible.

I think part of the courage to do that came from having to figure out a lot in college and my early career. But the final push that convinced me that I could really do anything I wanted to do was having children. Babies are the ultimate start-up experience. The hospital sends you home with one and says “Good luck!” And as soon as you start to get good at your job, it changes. More moms should start businesses. We are experts at figuring things out and learning on the job.  

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

I never expected to start and run a nonprofit! I was working in corporate communications at a private software company when the HR department decided to start a returnship program to bring former stay-at-home mothers back into the workforce. I thought it was a great idea and as the head of PR I also felt it was a great story! We got an article in the San Francisco Chronicle. That led to other companies becoming interested in what we were doing and looking for support and consulting.

Eventually our CEO, Matt Blumberg, felt like the program could have a big impact as a nonprofit to work with employers to create more of these programs. When he told me his idea it was as if a light bulb went off over my head—I thought “I have to be a part of this.” I’d never thought about becoming an entrepreneur. But the cause felt so important to me. And I like the challenge of doing things I’ve never done before. 

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

There is a scene in the third season of The Crown where the Queen is lamenting the new image of her as an older woman and someone refers to her as “the settled sovereign.” I found that to be such a compelling phrase, noting the complete lack of humility I may be showing by comparing myself to the Queen of England! But that phrase is a good way to explain how I feel now—I feel settled. I know what I know, I know what I don’t know and can figure out how to learn it. I also know what I’m good at and feel far more comfortable not trying to be “perfect.” I don’t feel the need to “appear” confident—I am confident. I feel like I have a firm foundation on which to build the next phase of my career—which feels very exciting. I know I can make mistakes and recover from them. I don’t feel as focused on what I might lose so I can stay more focused on what my team and I can win. 

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

I definitely felt stuck when I was in media. I’d love to tell some great story about having a grand epiphany, quitting media in a dramatic fashion after having landed a great new job and riding off into the sunset. In fact, I got laid off. It was the beginning of 2003, the economy was still rocky after the dot-com bust and I lost my job at News Corporation. I spent six months looking for a job—any job—in media. But it was a rough time and I actually ended up losing out on three jobs to people I knew! It felt like the walls were closing in. I then landed at Return Path—a small software company where I ultimately became the VP of Corporate Communications. The rest is history! Sometimes the universe really does need to give you a shove. 

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

Julia Child. I’ve read her biography and also the autobiography that she started and was finished by her nephew. Interestingly the biography is much more hagiographic. But I have a few reasons I love her. First, she is a late bloomer. She didn’t even take her first cooking class until she was 38 years old! She was in her 50s when she became the star we all came to know and love. When I was struggling in my early career I kept reminding myself that not everyone is a wunderkind. Second, she was an unapologetically ambitious woman. That really comes through in her autobiography—she was very driven and she wasn’t always nice about it! I admire that—we don’t expect men to be “nice” on the road to success. In the waning days of my media career I was working as a food editor and I got to talk to her on the phone. It was late in her life and she wasn’t well but it was such a thrill to talk to her! And she was quite humble. She said she “got lucky,” in her career, which, while true, is clearly not the whole story. 

What habit or practice helps you manage stress? 

I get up early every morning and go on a 3-mile walk. It gets me moving, clears my head and gives me an instant feeling of accomplishment. I also have dinner every night with my family. This is much easier now that we are in quarantine, but even when I commuted I prioritized getting home for dinner. Sitting around the table and reconnecting over a shared meal recharges me. 

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

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.

Career Q&A with John Mayfield, General Partner at Album VC (#10)

The next Career Q&A is with John Mayfield. I’ve had the good fortune of knowing John for more than 10 years and he’s one of the most genuine and kind people that I know. I love his advice on adopting a give first mentality, the power of developing soft skills, and why people shouldn’t over-index on compensation in the first 15 years of a career.

John Mayfield is an early stage investor at Album with investments in Route, Neighbor, Filevine, Podium, Divvy, Weave, Qwick, and Homie, as well as a board member with the Rocky Mountain Venture Capital Association. Prior to Album, John was an early employee at Qualtrics and pre-IPO Instructure where he worked in sales, marketing, and new product launches. Prior to that, he spent several years in Silicon Valley working on M&A valuations for top software companies such as Oracle, HP, Yahoo, Cisco, and Amazon.

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

One book that has had an influence on me that I almost never hear people talk about is The 15 Commitments of Conscious Leadership. The book is a must-read for anyone working with other humans. The concepts in the book have helped me identify in myself some of my unconscious reactions to work and life situations, it’s helped me in my approach to relationships, and overall improved the way I find energy to go after my goals. 

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

Don’t underestimate or forget the power of your relationships. I have loved watching friends and acquaintances from my past reemerge in my life in different contexts and being a resource to open up new opportunities for them and them for me. It’s something you have to live through to fully appreciate and I’ve found it very rewarding. 

Early in a career, it can feel like you don’t have a network but I’d challenge that and advise a college student to look around and develop relationships with those in your classes, clubs, and social groups. There are always people you can build friendships with and help out. Adopt a give first mentality and look for ways to help, it will come back around and it just makes life more enjoyable. The power of compounding is alive and well in the relationships you form early in your life and career. 

Advice to Ignore: I think most colleges have a built-in incentive to minimize risk and find the most expedient way to get people jobs–makes sense right? For some yes, for many or most I’d argue no. My experience is that colleges care very little about how fulfilled or meaningful your work will be and more about graduation and placement statistics. 

I believe that for college students, embracing uncertainty, tolerating more risk, being okay with developing networks and skills over steady pay, and having a more open aperture for opportunities creates more serendipity and many times more meaningful paths for a fresh graduate. 

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?

Salary is the primary focus for many people from the start and can lock you into a path that has limited upside, or worse, into a life you hate. Focus the first 15 years of your career on finding the right mentors, networks, experiences, and skills. After the first 15 years, you can start optimizing more for pay grade. 

What’s one of your proudest professional accomplishments? 

I’m most proud of the partnership we have at Album, the culture and brand we’ve built so far, and the incredible founders we’ve been fortunate to back. 

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

Growing up, school and early jobs teach you that it’s all about memorizing the right answers and doing tasks correctly and fast. I think I entered the workforce having that same mindset. 

Through years of experience and struggles, I’ve learned that it’s much more important to have softer skills like persuasion, critical thinking, and human relationship skills. While hard skills are important and have their place, at some point, you have to learn how to persuade other people to join your point of view after you’ve taken the time to think through something deeply. I now focus much more on how I effectively create accountability both in myself and others and find ways to create leverage in my day and structurally in our business.

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

This is where a good mentor comes in. Find someone who is two steps ahead of you in an area where you’re interested who can help you navigate. I also get a lot of value out of reading books and a number of podcasts. A few podcasts I’d recommend whether you’re in the investment world or not include: Invest Like the Best, The Knowledge Project, and Naval Ravikant. 

What habit or practice helps you manage stress?

I’ve recently picked up a daily breathwork practice. Breathing is something that we rarely think about but can create a massive shift in our state if used deliberately. There are techniques for anxiety, general stress, lethargy, sleep, and more. There are many apps out there but I use Breathwrk and Wim Hoff.

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

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.