18 Comments

First and foremost, Congratulations, Nick!

Second, I think there's another consideration in your list, which is being a party to someone else's success and being satisfied with that. You may not even realize that you were a party to it, but through positive "butterfly effect"-like interactions with those in a fairly small community (In SF tech circles, everyone knows everyone.), you may have indirectly, if not directly, influenced someone else's success. You were a great mentor at Tradecraft and have no doubt had a profound impact on others.

Third, as a parent of three - a boy, 4, another boy, 3, and now a daughter, 3 months - still working in technology, my definition of "success" has changed, though I've maintained my perspective that success is measured in decades (#4), rather than months or years. I've always been a tortoise, never a hare. Thus, I don't bother wishing I were a hare, just a better tortoise.

At 35, you have a lot of life left to live.

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Couldn't agree more. All my favorite people measure their success in terms of the value they've created for others.

Congrats on #3! I'll definitely need to get some tips from you as I navigate our second :)

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"my definition of "success" has changed"

I see you've taken #4 to heart! ;-)

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Hi! New here, and glad I found this space :) Genuine q: are you being ironic with this post and these 8 ’strategies’?

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It's definitely meant to be satirical. But like all good satire there are some kernels of truth from elements of my personality I'm not particularly proud of.

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We all have them ;) :)

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9) Imagine all the possible reasons they might envy you.

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Love this!

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Congrats, Nick!

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Thanks, Lyle!

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Congrats on the daughter to be! I don’t know if this your experience, but when my wife was pregnant with our second (a daughter) I couldn’t imagine loving a child as much as I did our first (also a son). More than anything else - scheduling, finances, etc. - I was worried I couldn’t give more love than I had for my oldest. And I was ashamed to admit this concern. I asked my older sister, who had three kids of her own, and she reminded me that love is like fire, not water. There’s no finite amount. And sure enough, she was very right! Not sure if it’s relevant for you, but that advice always stood out to me about the transition from 1->2 kids.

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I love this metaphor 🔥

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Hey Nick - I'm new to Substack and write about work-life topics. So happy I found your newsletter!

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Glad to hear it!

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Congrats on baby #2!!! I just went to Belize and had a lot of thoughts on how we (Americans) define success. It feels like the more opportunity we have access to can paralyze us into thinking we’re not good enough. If we didn’t have endless possibility would we be more content? Also - I love my coach!!

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New here and really enjoyed this one. I’ve started searching for a new job and could use all the help I could get. How can I learn more about the coach you recommend?

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Hey Jonathan, sorry just seeing this. Drop me an email (nick.dewilde@gmail.com) and we'll set you up with someone great.

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Somehow I completely missed the shoutout here, thanks Nick!

As someone who is also a guy-writing-onsubstack-with-a-boy-toddler-and-baby-girl-trying-to-help-the-tech-community I appreciate the overlap here! And I like your focus on guides and helping people. Realistically, some significant percentage of the workforce (myself included being a 2012 college grade) are moving into a job market they've never experienced before so just being helpful through these times I think is a great strategy.

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