Starting a job hunt now, some of my friends ask me how it’s going. Needless to say this is a rather stress-inducing question – one that for the most part, I prefer not to talk about. Unless the other person has some actionable help they can provide, or I value their emotional support. For the most part this is not the case; people ask about the job search flippantly, as if they’re just “checking in”. Of course, some people can provide resources or connections. Some people have great advice for mental fortitude – so it’s not all bad.

One reason that “how’s it going” is a hard question to answer is because progress is a multi-faceted thing to measure.

Tangible progress. This is what people typically expect when they ask me about the job search. In their head, the process goes like this:

• Decide what you want to do -> Apply like crazy -> Land interviews with whoever gets back -> Choose the least bad of those options

I’m not gonna make some bold claims about how that’s the wrong way to think about things, and I’m not going to suggest some competing framework that is miles better.

But do want to share about the intangible progress. I’ve made some of this, here’s what it looks like:

• Survey knowledge. Learning about an industry, the different companies around, the types of roles available. It’s hard to “measure” how much knowledge you’ve gained in a certain area, and harder still to distill it to a friend or stranger at a moment’s notice.
• Self-understanding. After learning about what is out there, there’s the question of, “what do I want to do?” This question does not have a simple solution, like the equation x + 5 = 7. If it did, then I would’ve solved this years ago in Algebra 1 (believe me). Self-understanding comes over time, over many conversations, slowly. And the process is never quite complete. I may get a job and find it doesn’t quite fit me. The process of self-understanding continues throughout your life. My parents, who worked for decades and are now retired, face the challenge of self-understanding. There’s a number of ways you can fill your time when retired – it is genuinely hard to contemplate what you really want to do.
• Conviction. Garnering conviction is the process of developing motivation to proceed along a certain path. If on Day 1 you are very unsure what to do, but you have an inkling that Option A is the one you want to proceed with; then on Day 30, you may have found more and more things about Option A that excite you. You may also speak the lingo of Option A, and know how it compares to Option B and C. Again, it’s hard to quantify how much conviction you have for a certain direction. And it’s something that comes in waves.

Writing this out like I just did, it occurs to me that this progress is real stuff. There is real research and decision-making that has to be done to pursue an intentional career change. It takes contemplation and reflection. But I fear when people ask about my job search, they’re not quite ready for a spiritual journey. Or maybe they are! And I should just prep them better. To steel-man my case for intangible progress, here are some other ways it counts:

• Startups. Startups spend plenty of time assembling a time, picking a direction and assessing the market before they start earning revenue. That period of building, testing, and experimenting is key. An example is Meta: when they were just Facebook, they went many years before they had any idea of how to monetize their platform. Focusing on results too early can harm the business in the long-term.
• Book writers. Consider the task of writing a fantasy novel like Harry Potter. The premise and world-building is essential to that story’s success (my thinking for this is that JK Rowling books following Harry Potter pale in comparison). Arguably, most of the important work for Harry Potter happened before she even wrote the first page.
• AI compute overhangs. ChatGPT was released in 2022, but the technology actually been possible for maybe 8-10 years before that. In 2016, tons of intangible progress had been made on artificial intelligence. It was illegible to the general public how amazing these capabilities were, which is why ChatGPT came to be seen as such a breakthrough.

Steve Dalton describes this phenomenon in the 2-hour job search. He says that while we know 85% of jobs are gotten through networking, people feel pressured to look like they’re working hard on the job search. And that means essentially wasting time sending apps through job board portals. Building a network and having conversations with people doesn’t necessarily make quantifiable, linear progress towards your goal, but it is the research-supported method for finding a job.

(If you’re then going to ask me “how many conversations have you had this week?” please just don’t. It’s annoying and unhelpful. Most people don’t want to be asked about work, because they think about it already so much. So don’t ask unless they bring it up.)

Now, I’m not saying tangible progress doesn’t matter. I’d certainly love to have a slew of interviews and job offers my way. But realistically, that won’t happen unless I’m committed to a career goal and ready to make it happen. Like many things, you can go too far the other way – and I also don’t want to be lounging around “contemplating” for months on end. But frankly, my personality is too stressy to ever do that.