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?

How to Set Expectations for Your Job Search After Getting Laid Off

I recently saw a post from someone in my network that shocked me.

He’d been impacted by a recent layoff and despite trying everything possible to find a new job (applying, interviewing, networking, etc.) he’d been unable to land something new.

Frustrated by his lack of success, he was ready to give up.

The shocking part was that it had been 17 days since he’d started his search. 🤯

He’d expected that after 2.5 weeks he’d have landed the job of his dreams. I wanted to give this person a dose of reality. And a hug.

Years ago when I was laid off, I was similarly optimistic. I genuinely thought I’d be out of work for a few weeks and would quickly land something better. Weeks turned into months and I wondered what was wrong with me.

I took every rejection personally. My optimism had been completely disconnected from reality. I had no idea the average job search took five months. Resetting expectations was painful.

Optimism is good. But the reality is that finding a job will take longer than you expect. And it’s going to be an emotional journey. You’ll face uncertainty and self doubt. Your confidence may be shaken at times.

But your mindset will make all the difference. Mentally prepare yourself. Put in the work. Build relationships. Show up. Control what you can control. Hustle until you’ve achieved your goal. 👊👊

Here’s an article I wrote for Fast Company about how to manage getting laid off.

I’d love to hear your thoughts. What have you done to successfully navigate a job search?

Don’t Focus on How to Play the Game, Focus on Which Game You’re Going to Play

A few years back I learned a lesson that hit me like a ton of bricks. And changed how I think about life.
 
I started my career in investment banking. It paid well and I enjoyed working on high profile stuff. It was fun being surrounded by talented people. But I really didn’t like the work. 
 
I was competent, but I wasn’t awesome. I wasn’t playing to my inherent strengths. I worked hard but wasn’t motivated to go above and beyond. I was in the wrong game. 

Years later I stumbled on this quote from Kwame Anthony Appiah that hit me hard: “In life, the challenge is not so much to figure out how best to play the game; the challenge is to figure out what game you’re playing.”
 
While in finance, most of my effort was spent on HOW I was playing the game (e.g. improving my financial modeling). But that wasn’t my problem. My real problem was that I was in the wrong game. And until I found the right game, my upside was limited. 
 
It took years, but ultimately I changed games. I made a career pivot that drastically altered the trajectory of my career. It was really hard at first and I had to take a few steps back.

But in this new game I was playing to my strengths and I was energized to go to work each day. That combo brought increased satisfaction and rapid growth. 

So how do you figure out the right game? First, you need to discover your inherent strengths. This can be hard to do early in career, but with with more experience you can look back over the types of work you’ve done and find the activities that come naturally to you and that energize you.
 
Don’t worry about how well you’re playing the game. That will come with time. Focus on playing the right game. Play YOUR game. Because that will make all the difference in the end.

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 Make Room for Inspiration in Your Career

Listen to the podcast version on AppleGoogle, and Spotify podcasts

I recently finished rereading the book, How Will You Measure Your Life? by the late Clayton Christensen. It’s a fantastic book. In it, Christensen discusses the differences between deliberate and emergent strategies.

In your career, a deliberate strategy is the specific plan you craft for your future, while an emergent strategy is a realized pattern that wasn’t expressly intended. In other words, an emergent strategy is the path you take after your circumstances have changed. It’s wise to have a plan, but Christensen believed (and I would echo) that too many people stress about their future and think they’re supposed to “have their careers planned out, step-by-step, for the next five years. High-achievers, and aspiring high-achievers, too often put pressure on themselves to do exactly this. . .”

Having a focused plan may make sense, but all too often things change. We need to make space for an emergent strategy. We need to leave room for inspiration. I am a man of faith. I believe there is a God and that he has a plan for each of us. I realize not everyone listening may share that faith, but it’s hard to argue with the times when we’ve felt guided to do something we didn’t intend to. Or times when a door opened that we didn’t think existed. This is inspiration.

If you’re anything like me, you want to have everything planned out. You’ve got a 1-year plan, a 5-year plan, a 10-year plan, etc. That’s what we’re taught to do, right? But some of the best things that have happened in my career were NOT planned for. Some of the best things have happened when my plans came crashing to the ground erupting in flames.

I’d like to tell a story of someone who had a difficult, unexpected experience in their career.

Hugh B. Brown, a former leader in my church, told the story of the time he purchased a rundown farm in Canada many decades ago. As he went about cleaning up and repairing his property, he came across a currant bush (on them grow tiny berries, kinda like a small grape) that had grown over six feet high and was yielding no berries, so he pruned it back drastically, leaving only small stumps. Then he saw a drop like a tear on the top of each of these little stumps, as if the currant bush were crying, and thought he heard it say:

“How could you do this to me? I was making such wonderful growth. … And now you have cut me down. Every plant in the garden will look down on me. … How could you do this to me? I thought you were the gardener here.”

Brown replied, “Look, little currant bush, I am the gardener here, and I know what I want you to be. I didn’t intend you to be a fruit tree or a shade tree. I want you to be a currant bush, and someday, little currant bush, when you are laden with fruit, you are going to say, ‘Thank you, Mr. Gardener, for loving me enough to cut me down.’”

Years later, Hugh Brown was a field officer in the Canadian Army serving in England. When a superior officer became a battle casualty, Brown was in line to be promoted to general, and he was summoned to London. But even though he was fully qualified for the promotion, it was denied him because of his faith. The commanding general said in essence, “You deserve the appointment, but I cannot give it to you.” What Brown had spent 10 years hoping and preparing for slipped through his fingers in that moment because of what he felt was blatant discrimination. Continuing his story, Brown remembered:

“I got on the train and started back … with a broken heart, with bitterness in my soul. … When I got to my tent, … I threw my cap on the cot. I clenched my fists, and I shook them at heaven. I said, ‘How could you do this to me, God? I have done everything I could do to measure up. There is nothing that I could have done—that I should have done—that I haven’t done. How could you do this to me?’ I was as bitter as gall.

“And then I heard a voice, and I recognized the tone of this voice. It was my own voice, and the voice said, ‘I am the gardener here. I know what I want you to do.’ The bitterness went out of my soul, and I fell on my knees by the cot to ask forgiveness for my ungratefulness. …

“… And now, almost 50 years later, I look up to [God] and say, ‘Thank you, Mr. Gardener, for cutting me down, for loving me enough to hurt me.’”

Brown never became a general, but he believed that the divine redirected his life to do something even more important, to serve a higher purpose.

Like Brown getting denied his general promotion, there have been a few times in my career where I felt I did everything right, everything within my power, to land a job or put myself in a position to succeed and things didn’t work out. The most obvious was when I was an investment banking analyst at Lehman Brothers. I had hustled like crazy to get that job and everything fell apart only a few months after I joined. I found myself out of work with limited prospects. I finally landed a job but for years I was frustrated. I felt like that experience had set me back. I felt that my plan had been derailed.

But, as time went on, things worked out. In fact, they didn’t just work out, I was better off because of the setback. Had I not gone through the painful experiences early in my career I wouldn’t have built empathy for job seekers, I wouldn’t have written a book, I likely wouldn’t have pivoted my career from Finance to HR. I wouldn’t be able to coach and influence executives. I am confident that these experiences—that were really challenging at the time—led me to a path that I may not have discovered otherwise. This was inspiration.

So, what do we do with all this? What do we do when our perfect plan gets derailed?

First off, we try to withhold immediate judgment. When unplanned things happen, we try not to assess whether they are good or bad. They just are.

Second, we need to create space for stillness. We need to create space for perspective. This rarely comes immediately and may take more time than we’d like.

Having a plan is good. But as Mike Tyson said, everyone has a plan until they get punched in the mouth. Some of the best things in our career happen when that plan isn’t realized. When that plan gets derailed. We need to create room for inspiration. We need to create room for an emergent strategy. Sometimes, like Hugh Brown’s currant bush, we need to be cut down before we can become the person we were meant to become.

4 Lessons From 4 Years at DoorDash

Listen to the podcast version on Apple, Google, and Spotify podcasts

Four years ago I left a comfortable job at an excellent company to join DoorDash, a Series C startup that had ~250 people. At the time, DoorDash was far from a sure thing. Several competitors had gone under and many were prophecying we were next. It’s been an incredible ride so far and while we’re just getting started, I want to reflect on lessons learned during this period. Here are four that stand out. 

1) Optimize for learning and impact 

Hours after coming to DoorDash’s San Francisco headquarters to interview, I got a call from the recruiter. Tony, the CEO, was about to leave town and wanted me to come in early next morning for a final interview. I had enjoyed meeting the team but this was a quick turnaround for a meeting of this magnitude. I had to work late that night and would have little time to prepare. 

The first part of the interview seemed to go well as I answered questions about my experiences in both HR and finance. But things went south when he asked me to share two new things I had learned over the past month. My mind went blank. I totally froze. 

After several seconds of silence, I answered his question but the examples I gave weren’t concrete. Trying to save the interview, I told him I knew my answer wasn’t impressive but that the primary reason I wanted to work at DoorDash was so I could accelerate my learning. And it was true! In my prior role, I was feeling comfortable but somewhat stagnant. I wanted a job where I could constantly learn. I wanted to have real impact. 

When the job offer came I was ecstatic. While the compensation package was less than what I was making, I knew I had to accept. I told myself that even if DoorDash wasn’t successful I’d still learn a ton. I’m grateful I accepted and my hypothesis held true. I’ve learned more over the last four years than I could have imagined. I’ve found that when we optimize for learning and impact, especially as we grow our career, the rest will take care of itself. 

2) Your limits are far beyond what you think they are

My first few weeks at DoorDash were a rude awakening. I had gone from an individual contributor on a highly structured HR team with well-built processes to leading a small, understaffed HR team. I was both player and coach, responsible for making key decisions and successfully executing them. While this was the key reason I decided to join DoorDash, it was very much a “be careful what you wish for” moment. 

Each morning I’d wake up filled with anxiety, my stomach in knots. I did my best to show up at work confidently, but I felt like a total phony. I’d experienced imposter syndrome before, but this was so much more. The sheer volume of work was challenging, but it was also the pressure of executing. I felt a tremendous weight on my shoulders. I had been hired to do an important job and I continually questioned whether I was up for it. 

A few weeks after starting, I had a conversation with my dad. Overwhelmed with work, I told him I thought I made a bad decision by joining DoorDash. This startup life just wasn’t for me. I didn’t think I could be successful. He listened for several minutes as I shared the challenges in front of me. He finally jumped in and asked if going back to my old company was an option. I quickly replied that it wasn’t. He then said, “Well, it sounds like the only path is to move forward. Just get up and do your best every single day. I’m sure things will work out all right.”

I sought to follow his advice. The boats had been burned at my last company. There was no turning back. I knew I needed to keep going. The knots in my stomach continued each morning but would subside after I got to the office. I sought to focus on the work and nothing else. I found that I needed to reframe can I do this? to I can do this

I learned that my limits are far beyond what I thought they were. I’m confident this applies to all of us. We can’t truly know our limits until we’ve tested them. 

3) Set boundaries

You don’t join a company like DoorDash if you’re looking for a slow and steady pace. While I had done 100-hour weeks as an investment banker early in career, my life had changed. I had a family with three young kids. I wanted to prove that I could handle the startup life but I didn’t want to abandon the things that were most important to me. 

On my first day in the office, I tried to feel things out. Most employees were younger than me and didn’t have kids. Was there room for someone like me? How could I fit in? Many at DoorDash stayed late and ate dinner together so I decided to join them. After the meal, my manager pulled me aside and asked what I was doing. I explained my desire to build goodwill with the team. He pushed back, saying that he needed me for the long haul and that if I don’t find a way to manage work and family I wouldn’t last long. He knew my priorities and was there to support me. 

This conversation empowered me to set boundaries. I had a long commute so I committed to leaving the office at 5 pm every day so I could be home with my family for dinner. On the flip side, I would wake up early and get to work before everyone else. This schedule wasn’t easy but my wife and I partnered to make it work. We welcomed our fourth child while at DoorDash and I made time to serve in my church and in the community.  

Had I not made the commitment to leave by 5 pm I don’t think I would have lasted more than a year. Setting boundaries was essential. 

4) Pause before placing judgment 

Kevin Delaney tells the story of a farmer who lived in a village on the outskirts of a town. One morning the farmer went out to plow his fields and found that the gate of his stables was open and his only horse missing. The neighbor noticed the empty stable and commented, “What terrible luck that your horse has run away. How will you farm your fields?” The farmer replied, “It could be good, could be bad, who knows. But I’m sure it will all work out.” 

Later that afternoon the farmer was mending his fence, and he noticed a thundering rumble growing louder and louder. He looked up to see his horse charging towards the open pen, followed by a team of wild horses. In a matter of minutes, there were a dozen horses secured inside the yard. The neighbor couldn’t believe his eyes and exclaimed, “How lucky you are! Yesterday you had only one horse and now you have a dozen.” The farmer looked at the horses and replied, “It could be good, could be bad, who knows. But I’m sure it will all work out.”

The story continues with several events that initially appear bad immediately followed by one that appears good. The farmer refuses to pass judgment at the moment they occur. He knows that there’s no value in wasting precious energy in constant judgment. 

I’ve learned the same goes for our careers. During my time at DoorDash, countless things have happened (getting layered, new manager, team reorg, etc.) that on the surface seemed to negatively impact me. In the moment I’d get frustrated and start spiraling. On one occasion, I considered leaving the company. Most of these situations, though difficult in the moment, turned out to be just what I needed. 

Endlessly debating whether things are good or bad is a waste of time and energy. I’ve now sought to live by the motto: Come what may and love it. We can’t always control what happens to us, but we can control our mindset. 

The last four years at DoorDash have been an absolute roller coaster. We’ve come a long way, but we’re just getting started (yes, we’re still hiring!). I’m fortunate I’ve been able to be a part of the journey and grateful for the amazing people I work with. There’s nothing better than doing meaningful work with people you care about. 

Onward and upward.

This article was originally posted on Linkedin.

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.