Good Work—Edition Nº 4

A hand-curated newsletter devoted to exploring how we choose to spend the 90,000 hours that will make up our careers.
Andy Sparks
▪︎ 6 minutes read time

🎶 Everything is Free by Gillian Welch

True self-awareness remains in short supply. When I mentor on career, the first question I ask is what are you optimizing for? Ends up being a difficult question to answer, with folks looking to me for what they should be optimizing for. But only looking within can answer that.Sachin Rekhi*

Answers to what we’re optimizing for can be troublesome. They’re often not even the real answers. “I want to move to New York City” can really mean, “I want to work with people who challenge me to think in new ways.” “I want to start a company” can really mean, “I don’t want to work for my boss anymore.”

In their book, Designing Your Life, Bill Burnett and Dave Evans talk about the importance of finding your “north star.” The phrase is a bit too Disney for me, but I like the distinction that a north star is something you optimize for over decades whereas goals are stepping stones towards your north star. We’re never optimizing for one thing, and these layers of wants, goals, and north stars interact with each other. Knowing what we’re optimizing for can be the real challenge, and the most rewarding one to figure out.

It might feel like a lot of work to look within, to ask uncomfortable questions, to find habits that keep you tuned in to what’s important to you, but if we don’t look within, we’re likely to find ourselves bouncing around the world like a pinball hoping not to fall into the gutter. Whether you’re starting a team, joining a team, or hiring onto a team, knowing what you’re optimizing for will help you determine whether an opportunity is a fit or not, possibly saving you months or even years of time spent working on the wrong thing.

So how do you figure any of this out? In the next two editions of Good Work, we’ll share thoughts, ideas, and frameworks. Stay tuned.

This Week


Continuing on one of last week’s themes, I came across a tweet by @MicahPpls this week. He asked how many followers one needs to be able to effectively use Twitter as a learning and career building tool. I believe it’s less about follower count and more about a person’s willingness to engage with people they find interesting.



  • [8m] In “The End of Employees,” Lauren Weber of The Wall Street Journal shows the dramatic increase in companies use of contract labor over full-time employment. Short on time? Check out the chart.
  • video [11m] In his TED talk “What is the meaning of work?Roy Bahat of Bloomberg Beta shares his story of how, as a venture capitalist, he set out to understand the impact of automation and economic growth on the future of work. After examining hundreds of studies and traveling all over the United States, Roy’s findings are worth the eleven minutes.
  • video[19m] For a great primer on how to make sure you’re getting a fair shake with your boss, watch “7 Annoying Boss Behaviors That Are Actually Illegal,” by Chelsea Fagan of The Financial Diet.

That’s Good Work for this week. Looking forward to what’s next. See you next week.

Andy and the Holloway Team

Good Work is written and curated by Andy Sparks, Courtney Nash, Dmitriy Kharchenko, Hope Hackett, Joshua Levy, and Rachel Jepsen.

If you found this post worthwhile, please share!