Reminiscing: the retreat to comforting work.

In Work on what matters, I wrote about Hunter Walk’s idea of snacking: doing work that is easy to complete but low impact. The best story of my own snacking behaviors comes from my time at Stripe. I was focused on revamping the engineering organization’s approach to operating reliable software, and decided that it might also make sense to start an internal book club. It was, dear reader, not the right time to start a book club. Once you start looking for this behavior, it is everywhere, including on your weekly calendar. Snacking isn’t necessarily bad, a certain amount gives you energy to redeploy against more impactful tasks, but you do have to be careful to avoid overindulging.

Beyond snacking, which can be valuable when it helps you manage your energy levels, there is a similar pattern that happens when a business or individual goes through a difficult moment: under pressure, most people retreat to their area of highest perceived historical impact, even if it isn’t very relevant to today’s problems. Let’s call this reminiscing. When you see your very capable CEO start to micromanage words in a launch email, or your talented CTO start to give style feedback in code reviews, take it for what it’s worth: they’re reminiscing. If you spend the time to dig deeper, they’re almost certainly panicking about something entirely unrelated.

Some real examples from my experience (don’t try too hard to connect them to individuals, I can quickly think of multiple examples for each of these):

• “The systems I architected never had significant reliability issues.” Senior-most engineering leader drives top-down rearchitecture of the company’s software, often anchored in the design problems from their last in-the-details technical role rather than current needs (e.g. a Grand Migration). They’d be better served by addressing the cultural or skill-gaps culminating in the reliability problems instead of trying to solve it themselves
• “We need to take more risks in our work.” Founders feel trapped by slog of meeting financial projections, and want to reorganize company efforts towards increased innovation without connecting dots to how it will meet the financial projections. Typically this is a throwback to an earlier company phase that is a poor fit for the current phase
• “The team I hired was much stronger than this team.” After years of absence, a founder starts revamping the performance or hiring process to address a perceived gap in hiring but without the context of why the process has evolved the way that it has. They’d be better served by holding their managers accountable or empowering their People team

Each of these examples is tightly ingrained into the person’s identity about why they’re someone successful. You can help them recognize the misalignment with today’s needs, but real progress on this issue depends on their own self-awareness. It usually won’t go quickly, but it always gets resolved faster than you might expect, typically through growing self-awareness but rarely by abrupt departures.

Over the past few years, I’ve gotten much better at being mindful of my own snacking inclination. That urge to reorganize our engineering wiki when work gets difficult? Even without knowing the other work I could be doing, it’s easy to identify: that’s snacking, for sure. Reminiscing is much harder for me to identify in a vacuum, it is valuable work, and it’s sometimes very impactful, difficult work, it simply isn’t particularly valuable for you personally to be doing right now.

To catch my own reminiscing, I find I really need to write out my weekly priorities, and look at the ones that keep slipping. Why am I avoiding that work, and is it more important than what I’m doing instead? If a given task slips more than two weeks, then usually I’m avoiding it, and it’s time to figure out where I’m spending time reminiscing.