As the clocks rolled back here in the US this past weekend, I wondered where the time went. April and May were spent job searching and building an MVP of HeatCheck. June and July were mainly spent on vacation with some job searching to keep the unemployment flowing. August was interviewing for a CTO position at a startup in Austin and a few other opportunities. September was filled with rejections and refilling the interview pipeline. That’s also when I first started seriously considering contracting. October started with a contract, interviewing for an international CTO position, and I wound down the full-time job search for the time being. Here we are in November. Phew. 

Looking through the end of the year, more contracting seems the likely path for now. Running SimpleAndDone has a lot of similarities to my time leading the Incubator Engineering team. As my contracts pick up, I’m finding the balancing act between discussing new possible contracts and working as a fractional CTO a fun challenge. Next year, I’ll have a few different contracts simultaneously, with a new set of challenges. I’m also exploring launching a new executive coaching accelerator for senior engineering managers looking to move into Director, VP, and CTO roles. I’ll be partnering with a top executive coaching firm here in Austin to market and run a six-month course and coaching program early next year.

As we start toward Thanksgiving, I’m practicing more gratitude, and right now, I’m thankful for the opportunity to work as a contractor or fractional CTO. I recognize that many people don’t have the opportunity, skills, or desire to work as a contractor. I consider myself fortunate in this regard. That said, I do severely miss the stability of a salary, the benefits of a full-time employer (without paying COBRA), and the consistency of a great set of coworkers. 

Numbers

40, 20 – micro-layoffs from Google in News & Voice Assistant teams (more signal of quiet layoffs). Source Source

50% layoff at OpenSea, the NFT marketplace. It’s not exactly a huge surprise given NFT performance of late, but still, another 100+ people are hitting the market. Source 

1.50 jobs per unemployed person (up from the pandemic low of 1.2, but down from what was approximately 2.0 at points in 2022.) source source

ChatGPT/DALL-E 3 Timesaving

I’m not an expert prompt engineer, but I’ve been leveraging ChatGPT, Grammarly, and DALL-E 3 with the job search and other tasks more and more. Tools like RampedCareers and Swooped are great for wrapping the typical job search tasks into helpful prompts – feedback on your resume, custom cover letters, job applications, and more. ChatGPT can be an excellent practice interview tool, a tutor for new skills you’re working to acquire, or an editor for messages you’re sending. DALL-E 3 has been great for mocking up logos for the kids’ baseball team, and I’m curious to see if I can even use it (or something like it) to help me build quick wireframe mock-ups of products I’m consulting on. Let me know in the comments what sorts of ways you’ve been using Large Language Models to help in your job search, household tasks, and other activities.

Time for Goals

As we close out 2023 and start to look forward to 2024, there are a couple of critical corporate functions that always have to be done. Teams will begin to lay out annual plans and goals, and finance wants to see annual budgets. Of course, some companies have a shifted corporate calendar, and their dates may not align with the end of the calendar year. Even then, the end of the year is a time of reflection.

Goal setting is a complex problem of getting enough context on the space to set reasonable goals and having enough of a broad perspective to set significant objectives. Objectives and Key Results (OKRs) are structured to create broad objectives influenced by on-the-ground data. From the time you first set high-level objectives and potential key results to the time the OKRs are finalized, it can easily take weeks or more to get the context shared across all teams. Starting early gives time to explore adjustments and ensure everyone is aligned on the objectives and has the data they need to measure the results.

The budgeting side is another complex piece that has to be done simultaneously. Budgets affect the headcount growth and other investments to make a goal deliverable. So, goals must be formed to shape the budgets, and budgets must be loosely set to create achievable goals. It’s another chicken-and-the-egg problem. 

Ultimately, however, neither of these projects is one-and-done for the year or the quarter. To do this right, you’ve got to check in on how the budget and goals are working. End-of-year planning is an ongoing exercise all year long. 

Fun