It is always helpful to have a roadmap for an unfamiliar experience. I did not, as I embarked on an intense job search. But maybe my reflection will be useful to others.

I noticed that the process has followed an arc. Much like chess, it has a distinct opening, middlegame, and endgame. Each of these phases has a very different feel, and has required me to optimize in different ways.

Opening

For the first few weeks of my search, I was intensively prospecting for leads on roles, while iterating on my own marketing. This felt like hours soaking up information, browsing LinkedIn, and interacting with people. I wanted to put the greatest number of folks on notice that I was on the market. People can’t help you unless they know what you need. This time was filled with connection, reflection, writing, and revision.

This being the first open-ended job search of my professional life, I invested a lot of time on my personal brand. I don’t mean being an influencer; I mean being able to concisely communicate what I’m looking for and what I offer, so that people can help me find good opportunities and so that my discussions with companies can efficiently figure out mutual fit.

The most obvious piece is my resume. I’ve iterated through a couple dozen incremental revisions in the past couple months. Each change was pretty small, but the end point is a significant revamp from where I started. Other efforts included work on this website, tuning up my strategies for corresponding with people, and workshopping answers to common questions.

But most of all, I was prospecting. I didn’t want to stop searching for leads until enough made it to the stages of active communication with recruiters and managers that I was fully occupied with managing processes.

Middlegame

At some point, I noticed that I was spending way less time on open-ended activities, and way more time being led by my calendar. Entire days became booked up with interviews, as my top-of-funnel¹ began to hit and I found the best channels for opportunities. Some great opportunities disappeared or turned into rejections, but I had more than enough things coming through to not get discouraged.

I also found that my quality of opportunities started to increase. I think there are several reasons:

• I got better at finding productive sources of good leads.
• My process of networking and corresponding became more efficient.
• I had less need to spend time on “safety opportunities” as better ones got further along.
• My own vision of what I’m looking for became sharper through introspection and countless iterations of articulating myself to other people.

I began struggling with the administrative overhead of scheduling and adopted Calendly. I started blocking off post-interview time so that I didn’t end up in back-to-backs. I created more systems for managing my tasks and staying on top of follow-ups, take-home work, and preparation.

Much like the opening phase, the middlegame involved continuous introspection, processing what was going well (or not) in interviews to make sense of my experience, refine my selection process, and improve my performance.

This period was actually pretty fun, on the whole. I experienced a continuous sense of new possibilities as new leads opened up, as I succeeded in getting productive intros, and as I got to learn about dozens of companies. I experienced a lot of closed doors, but there were always plenty of ongoing and new threads to provide hope.

Endgame

As promising opportunities started entering full interview loops, I began to plan for decision time. The application and interview process started to feel less like a loop and more like a process that needed to be managed to an end point. Rather than looking at dozens of low probability top-of-funnel opportunities, I was looking at roughly 15 things that seemed pretty promising and reasonably likely to produce attractive offers.

I knew that the time for taking introductory calls would end and I would need to prioritize the real prospects. And it’s not just getting to an offer stage, but also making time for due diligence and negotiation. I need to make sure I make a choice that optimizes for all the things I care about. Compensation, obviously, but also work-life balance, team dynamic, mission, project, and so on.

Eventually, it was clear that my first offer was coming through. This presented a challenge in that I was in various points with my other applications processes, with some only just beginning. I began notifying serious leads that I likely going to be on the clock, so that they could prepare to expedite my process, if possible.

I picked a day to shoot for, which seemed like a reasonable balance between not keeping my first offer on the hook for too long, while giving enough courtesy to other companies who had already invested time in my application. But also: my severance pay is limited and I’m ready to resume working. Several roles got dropped from the running, because the timing wasn’t going to work out.

Checkmate?

As I publish this, I haven’t yet made my decision. My brain has become accustomed to treating the job search as my occupation and uncertainty being my reality. Being employed still feels like a mirage.

But the plan is to consider all offers I do get and make my decision by Friday. After that, I’m reserving 1 week to decompress from this process to let my brain reset and to take care of as many loose ends on the homefront as I can.

And then it’s on to the mission, whatever that might be!

1. The concept of funnel analysis describes how there are a lot of processes that begin with a large number of prospects and converge to a small number of successes. Each stage of the funnel invariably has drop-off. In the context of a job search, the top of the funnel are the discovered opportunities that are relevant to me. ↩︎