The Coffee Chat (#45)
My conversation with Nick DeWilde - Co-Founder & Chief Customer Officer at Exec (exec.com), Writer at The Jungle Gym and dad to 2!
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Hi there 👋🏽
About a decade back I saw a Bollywood movie called The Lunchbox, which has a line that I have increasingly grown to love - “Sometimes, the wrong train will get you to the right station.”
I've come to recognize the beauty of embracing the unexpected. In a world where we're often conditioned to tread the well-trodden path, to optimize every decision, and to move ever-forward on linear trajectories, diversions can be delightful!
Yet, I too have succumbed to the allure of the straight and narrow. I've sprinted down those well-paved avenues, chasing dreams and ambitions with a determined heart. But life, in its infinite wisdom, has time and again nudged me toward detours I hadn't planned for – some welcomed with open arms, and others met with a measure of reluctance. Yet, it's from these bends in the road that I've discovered some of the most exhilarating moments of my existence.
New horizons have opened up with every twist. Fresh passions, uncharted industries, unexpected roles, and even foreign lands have unveiled themselves to me, all because I dared to hop onto those so-called "wrong trains." It's on these seemingly misguided paths that I found the very stations tailor-made for my personal and professional growth.
Have you granted yourself the freedom to wander? To stumble upon hidden gems you never knew existed? To embrace the unscripted and be utterly, blissfully surprised? In our perpetual pursuit of optimizing our lives for a predefined vision of success, we often overlook the splendor of life's unplanned rendezvous.
Remember, ceaselessly optimizing for a singular goal can lead us to overlook the intricate tapestry of experiences that shape our truest selves. Sometimes, it's the unplanned, the unforeseen, and yes, even the "wrong," that gifts us the insights, the thrills, and the growth we truly need.
I do hope that you all too can trust yourself to find the right stations on the most unexpected tracks because constantly optimizing for a certain life you desire sometimes makes you miss out on the life you need!
☕ Now, on to today’s coffee chat…
Meet Nick DeWilde
If you are a person who lives on X (formerly known as Twitter), Threads or is a newsletter nut then you have probably heard of Nick, he is the brains behind the very popular newsletter The Jungle Gym.
And if this is the first time you are hearing of The Jungle Gym, then please do yourself a favor and check it out. When I first discovered it I binge read the newsletter. Like literally binge read it. Was lost in it for hours.
Nick is one of my favorite writers in the talent development space. Recently he also became a dad for the 2nd time!
Below is my conversation with Nick…
Please tell us a little bit about yourself and your family
I’m Nick, Co-founder of and Chief Customer Officer of a company called Exec. We are a tech-enabled talent development agency that helps companies design, manage and launch customized coaching and training programs. I also write a newsletter called The Jungle Gym which covers learning, future work, career strategy, and that goes out to about 12,000 people.
My wife, Ashley, is the Chief of Staff to the president of a company called New Front Insurance. She's been with that company for quite a while, so she's seen a pretty crazy growth trajectory over there. Together, we have 2 kids - a two-year-old son and a 2-month-old daughter. They're amazing and we're definitely in the thick of it from a parenting standpoint.My career has mostly been in the talent development space. I graduated from Stanford business school in 2015. And then helped run a career accelerator program that trained designers and marketers. I did that for about four and a half years and then joined a startup in the corporate upskilling space called Guild, where I was leading product marketing. In June 2022 I partnered with my Co-founder Sean Linehan to launch Exec.
So you are now an entrepreneur, you write a very popular newsletter and your partner too seems like she has her hands pretty full. So how have you both figured out being a dual career couple with young kids? What do you both do to make it all work?
I won't say that we have everything figured out, but I think both of us get a lot of energy from our work. I'm a strong believer in the idea of cultivating a portfolio of meaning. That means there are several areas of life that give you fulfillment. It's not just work, or family, of friends, or hobbies, it's all those things together. They feed off each other. If one thing stumbles, the whole thing doesn't fall apart. We give priority to family, but it's a balance. We make sure our situation is set up right - living near my parents, and having childcare, affords us time to pursue what we care about.
One of the differences between being a working dad and a working mom is societal expectations. Dads basically get applause whenever they do anything parent-related whereas society puts a lot more pressure on Moms to be perfect parents. I try to make a conscious effort to not just be there for my children but actually do the hands-on work of raising children. I've needed to really work hard to be much more thoughtful about playing that role in a smart way.
What are some things that men can do to support their partners at a very tactical level?
That’s a good question. I recommend being really explicit about the responsibilities you own. Decide who does the dishes or who picks the kids up from school. It’s much better to make these responsibilities explicit vs. hoping you’ll be thoughtful enough to take them on. For Dads especially, I recommend trying to give your partner the freedom to leave the kids at home with you and go out to dinner with friends.
I have a question about this concept of a portfolio of meaning. So many people struggle with it, was that hard for you? How did you develop this way of looking at life more like a jungle gym than a straight ladder?
I believe it's crucial to align your priorities with what matters to you. Personally, having energy throughout the day and feeling emotionally engaged in my work is really important to me. I can dedicate extended hours to work I care about, whereas it's challenging for me to find motivation for something I'm not invested in. This perspective forms the basis of my approach.
Personally, I tend to thrive on impactful projects within smaller teams, and this preference likely guides my decisions. Reflecting on my career trajectory, I've undergone distinct phases, but I struggle to recall periods lasting over a month or two where I wasn't genuinely excited about my work. As soon as my enthusiasm wanes, I'm inclined to pivot to something new.
This approach necessitates taking calculated risks and embracing uncertainty. That said, looking back, there aren’t many moments where I wasn't genuinely enthusiastic about my work.
So you have made a few career changes and pivots, even today across pretty much all cultures there is the archetype of Mom - caregiver, Dad - provider. Given that did you feel any pressure when you took the decision to go down the entrepreneur route? Tell me more about that thought process?
Having a baby both increased and decreased my level of ambition. The increase came from the feeling that time is now scarce and I should use my hours more effectively. The flip side of that is that my tolerance for performative work really plummeted. That was part of what motivated me to start a company. I like work that touches the metal of reality. Rather than having my work be judged by a manager, I like being in a situation where my work is being judged by the market.
Looks like being a dad has certainly been a transformative experience for you. What has parenting taught you about yourself?
Adults spend a lot of time fixating on abstractions – their bank account balance, social status, LinkedIn profile, etc. That's not the case with babies and young kids. They focus on the present, on what's right in front of them – whether it's getting milk, sleeping, eating, or other immediate needs. I found that to be really grounding.
One practice I've adopted, particularly with our eldest, is taking afternoon walks together. He’s still at an age where he's willing to hold my hand as we walk down the street. I recognize that this period won't last forever, so I make an effort to fully cherish those moments.
Any other new beliefs that you have adopted after becoming a parent?
I think that modern society has instilled in us the notion that careers are the only way to win status and find meaning in life. However, the reality is that most jobs, careers, and companies fall short of providing lasting fulfillment. The people who find career success are often celebrated, perpetuating the idea that this should be the primary source of fulfillment. But, the truth is, most jobs just aren’t that fulfilling.
Society has sometimes suggested that focusing on parenting is of lower status compared to a career. From my viewpoint, this couldn't be further from the truth. All our ancestors made the decision to have kids – a selfless act that led to our existence and our own ability to make these choices. As a male, I recognize that I bear a smaller portion of the parenting load. However, it's important to have deep respect for the challenges and significance of childbirth and child-rearing. While I have strong opinions on this, I also understand and respect other perspectives. Thankfully my partner and I are in alignment on this topic..
Great advice, any other piece of advice that you would like to give to other parents or just people on the cusp of becoming parents? Also, any popular piece of advice that is usually shared and you will tell them to ignore?
As a parent, it’s easy to get into this mindset where you keep waiting for the development milestone - like I can't wait till you he is 6 months old, I can't wait till he is sleeping through the night, I can't wait till he is walking, talking, etc. This is the same mindset we get into at work too - I can't wait till I get a promotion, I can't wait till I hit X $, I can't wait till my company IPOs. What happens with this mindset is that you miss out on all the fun you are supposed to be having the whole time on the journey. If you have one child you only have one year of having a one-year-old. So make sure you savor those moments
The advice that I might ignore is this whole concept around laissez-faire parenting, you know the idea that the kid will turn out how the kid has to turn out. I don't think that is true. Kids absorb a lot.
So good parenting is still really important. You do in a way sort of shape your kid, you can't fully control everything but the way you approach things makes a big difference on how your baby grows, develops and the choices he / she will make. So you need to be that person around them that you want them to be..
P.S: You may also want to check out a recent post Nick wrote on his wonderful newsletter - Practical Productivity Advice for Parents with Small Kids
Quick-fire questions:
What’s the best thing you have watched recently?
What’s the best thing you have read recently?
What’s the best thing you have listened to recently?
Bari Weiss has a podcast called Honestly that I really love listening to
🤓 Open tabs…
(I have modeled this section after those “open tabs” that we all have with a few (okay 30-40) interesting links that we promise we will eventually get to one day. These are the links that I had open for sometime that I finally got to …)
⭐The perfectionism trap
Society bombards us with instructions to be happier, fitter and richer. Why have we become so dissatisfied with being ordinary?
⭐Your Fitbit has stolen your soul
Our quest for self-knowledge has corrupted humanity
⭐The Cost of Greatness
What will be the blood sacrifice on your altar of ambition?
📖 My private thoughts from my very public diary…
(My Twitter use has drastically gone down, I am now more active on Threads)
I would love to hear from you, feedback is always welcome!
And if you happen to know an inspiring working parent who should be featured in a future edition (or if you yourself are one) - please do get in touch
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Disclaimer: All views expressed are my own and do not necessarily reflect the views of my employer