This is the Too Many Trees newsletter, where I share what I’ve been writing and reading in the realm of leadership and personal development. My coaching practice is centered around the idea that we are more effective in moving towards our goals when we become more conscious and intentional in focusing our time and attention, and learn how our unconscious patterns are holding us back. If you know somebody that could benefit from my perspective, please forward this to them or let them know they can set up a free intro chat with me.
Hunter Walk is a former Googler/YouTuber and now venture capitalist. I follow his blog, and was really touched by his post from December 2019 on How I Calmed the Failure Tiger Nipping at My Heels where he shared how his success was driven by the fear of failure. As he writes, “It drove and motivated me, but also poisoned the accomplishments; played a role in anxiety, sadness and physical ailments.” I loved how he vulnerably shared this dynamic, as we too often lionize those who work beyond their limits rather than acknowledge the cost of such overwork.
I finally wrote him this week to thank him for writing that post, and shared my own story of the “failure tiger” with him, and wanted to share an edited and expanded version of that story here as well.
I really resonated with the failure tiger post - I spent most of my life being terrified of failure, and thinking I had to succeed at everything I did. And that really limited me, because I wasn't willing to take chances - I only committed to things I was sure I could do.
The funny thing is that it took me into my 30s before I had to confront that as a limitation. I lived on the fast track - went to MIT at 16, then entered the Stanford physics PhD program before dropping out in 1998 to become a programmer like everybody else in the dot-com era. I bounced around five different startups over ten years, ending up at Joel Spolsky's Fog Creek Software to be part of his "Software Management Training Program". And even though I think I did a decent job, I ended up getting fired after two years. Total failure. First time in my life I failed at something that mattered to me.
I picked myself back up, and joined Google on the finance side as a revenue analyst in September 2008. Being a revenue analyst during the Great Recession was “fun” - by April 2009, I was giving monthly presentations on the revenue forecast to the leaders of Google, including the CEO and CFO. After failing at my last job, I was not going to fail again, so I said yes to any task, and took on more work and more work so that I could succeed and prove myself worthy.
Of course, after 3 years of taking on more work, and regularly working 8am to midnight 6 days a week to keep up, my body broke down, and I burned out. And I went into my manager's office and said that I wasn't willing to work like that any more, even if it meant I wouldn't get the promotion I had been so desperate to get. And she said "Are you sure?" and I said "yes". So she gave half my team to another person, and slashed my performance rating to kill any chance of a promotion. And....the world didn't end. I had "failed", but I actually felt good about it - I had chosen my own health and well-being over jumping through the hoops "necessary" to get promoted.
After that "failure", I went looking for a new job, and hooked up with the product VP of Search Ads, who I had worked with as a revenue analyst, to become his Chief of Staff for six years (which also got me the promotion I’d given up on). I chose to leave Google as his scope continued to grow (he now leads all of Ads at Google), because I could see what it would take to support him in that role was more than I was willing to give, especially since I had just become a father.
Learning to acknowledge and embrace all of these aspects of my story through therapy and coaching has helped me understand how those experiences led to me becoming the person I am today. And with that greater understanding that I choose what is success and failure, and that “failure” can lead to learning and growth, I took the “risky” leap into executive coaching, helping leaders become more effective by learning to face their version of the failure tiger. My new career allows me to have meaningful impact while also setting my own schedule and putting my family first. Both and, not either or.
And my coaching clients appreciate that I share the setbacks in my journey; it helps them acknowledge that such setbacks are not necessarily a reflection of their innate deficiencies, but opportunities for growth and integration. Each "failure" is part of the story of how they built their resilience and learned who they want to be as a leader, which helps them find clarity on their next steps. And I support them through that discovery process, and we experiment and iterate our way forward.
Anyway, I wanted to thank you for being open about your journey, as I think most leaders keep that vulnerability inside, and just share how they are "crushing" it. It's valuable for people to see that it's not easy, and that much success and overwork is driven by fear and anxiety, as you shared.
And now for the normal personal development content:
Blog: I wrote the next post in my alignment series talking about aligning with oneself. It’s surprisingly hard to get one’s internal ecosystem of parts aligned, as they often have competing goals that pull us in different directions. And yet, when we can bring them into alignment towards a higher purpose, we can increase our clarity and focus and become more effective.
LinkedIn: These are ideas or questions that help my clients (or myself), and that I share via LinkedIn to help a wider audience.
How do you get others to do something? A standard method is to use power, which turns interactions into a zero-sum power struggle. I’ve been exploring using alignment to bring different stakeholders together into a common vision.
It is challenging to transition from doing the work to defining the work. Delivering success on a clearly defined project is how most of us start our careers. Learning to dive into murky areas with no clear ownership or goals to create clarity for others is a step towards acting as a more senior leader.
Building a stakeholder map is a valuable technique to clear up the murkiness described in the previous bullet. By paying attention to the questions and comments stakeholders ask in meetings, you can learn about their underlying motivations, and use that information to earn their trust and increase your influence.
Articles and resources I’ve liked recently:
This tweet thread from Marco Rogers is worth reading in full as he shares how white (privileged) people avoid real talk so they don't have to acknowledge reality.
While writing my alignment blog post, I discovered a fantastic Jerry Weinberg article from 1996 called Beyond Blaming. He advocates for congruence, which “is a concept that describes the human experience of alignment between the internal and external – what is thought and felt (the internal), and what is said and how it is said (the external).” He describes a strategy for increasing one’s own congruence, which enables greater congruence in the systems in which you participate.
I appreciated reading this John Gardner talk on Personal Renewal: “Life is an endless unfolding, and if we wish it to be, an endless process of self-discovery, an endless and unpredictable dialogue between our own potentialities and the life situations in which we find ourselves.”
Amusingly, the reason I finally wrote to Hunter Walk was because I wanted to thank him for recommending this Dash egg boiler. I bought it, and it makes it foolproof to make perfect boiled eggs without paying attention. Brilliant since I love eggs as a snack, and now it’s easy to make 6 at a time.
Thanks for reading. See you in a couple weeks.