I had a hard time processing the video shared by Brittany Pietsch this week, and it pushed me to think more about my layoff. I had generally reached the “acceptance stage” (Kubler-Ross stages of grief model: Denial, Anger, Bargaining, Depression, Acceptance) for the layoff, but that video pulled me back into the anger range again briefly. Thankfully, I’m now 9+ months removed from the layoff, and those feelings didn’t last too long. Afterward, I had a (somewhat) new revelation: Indeed’s layoff pushed me to do something I would probably have never done on my own, even though I had considered it for a long time. Starting my own company and contracting with several different companies (simultaneously, no less) has been one of the most growth-inducing moves in my career. 

This week and next, I wanted to share about the projects I’ve been working on the last few months. I’ve alluded to them previously, and at least one is still in stealth mode, but the fractional CTO/consulting world is a new one for me so hopefully sharing learnings from this will help others decide when/if to make the jump that I should have more seriously considered years ago. 

The truth is that this work is not that different than my last role at Indeed. There I was leading between seven and 15 teams working on early stage new product innovation. I helped coordinate staffing, budgets, roadmaps, architecture, alignment, and much more. The biggest difference now is that I don’t have a support staff to help me do all of this. I always ran a lean organization, but I also preached as often as I could that “a team of one was no team at all.” But that’s where I am right now. Let’s start back in April of 2023 with the first post-Indeed project I took up.

Commiseration & Encouragement

The day I was laid off, I reached out to two good friends. One invited me out for a beer that afternoon/evening, and the other said “let’s grab coffee in the morning.” Both were exactly what I needed. A chance to vent, commiserate, and complain in a safe space, and then quickly a place to move into brainstorming what’s next and action. In fact, over coffee the friend explained that he had started HeatCheck just a few months before and had been building the MVP with WordPress and ChatGPT. I took a few weeks to think things over and since I had no serious job prospects, figured that sharpening my development skills by rebuilding his application on a more scalable, flexible platform would be a good challenge. Over the course of about a month of work I was able to build the application (including all of the Stripe integration and Progressive Web App hooks.) Not too bad for a rusty old programmer with a fair amount of support from Github’s Copilot. 

I took a break from building this to take the family on vacation, and when I came back finished off the mobile applications (iOS & Android) and started preparing for a more public launch. As we speak we’re preparing the last bits of data for several more sports (Baseball, Softball and more), and working on a Gmail integration for emails & notifications. This project has been a great push to get my hands on code, deployments, monitoring, and all of the nuts and bolts of shipping software that I had gotten so far removed from.

I <3 Coaching

I started my career teaching due to the Dot-Com Crash in the early 2000’s right as I was graduating with a Computer Science degree, specializing in web development. That meant there were little to no web development jobs, and post 9/11 most of the software jobs I was seeing were in Defense related companies that I had no interest in joining. I got the chance to teach Visual Basic and Java over the next year and a half while working on my Masters degree in Information Science & Technology (effectively Applied Computer Science & Management combined). I really enjoyed teaching and always thought that it might be interesting to go back to that space again another time. 

In August I was approached by Emergent Execs (an executive coaching firm here in Austin I had used previously to help train new managers) to help develop a Technical Executive Accellerator curriculum. Over the next few months I wrote a synopsis of the course, dug through existing executive coaching materials, and consulted friends to see what topics I had to include in this training. We’re now thick into the sales and marketing phase of the program launch. Meeting with prospective attendees to see if they are a good fit, would be interested, and have budget for such a program.

I’m excited to share my experiences and materials with managers, directors, VPs, and CTOs in product, engineering, and UX over the next six months. I really want the course to be an accellerant for people’s careers and a meaningful improvement to the teams’ they lead. More than anything, I’m excited to be coaching individuals one-on-one again, as that’s one of the things I miss most post-Indeed.

Fun

Happy New Year! Welcome to 2024. It’s time to start a new journal. I’ve kept journals for over 10 years and have notes from my time at Bazaarvoice in 2010, maybe even earlier if I look hard enough. They’re helpful for reflection, and occasionally, there’s something I did previously that I cannot find in my brain but still exists on paper in a journal somewhere. Thanks to Bullet journaling, I have an index and page numbers, and the whole journal is more or less chronological, so finding something I’m interested in is generally possible.

However, in the last few years, I have moved away from pen and paper for my daily journals. I still love the tactile feel of a good journal and a great pen, but the simplicity of the Remarkable for me to be able to have all of my journals (personal, work, 1:1s, church, and more) at my fingertips at any time is too much to ignore. I switched to the Remarkable when I got mine back in late 2021 and never looked back (except for travel journaling, but that’s different.) 

Anyway, I digress. I wanted to tell the story of how vital writing has been to processing all of the changes that 2023 brought. This weekly journal has been an outlet for how things are going, a way to keep up with those going through it alongside me, and simultaneously a way to connect with others beyond my immediate network. Journaling has been incredibly important as 2024 came around, and every contact I have went into hyperdrive (recharged after the holidays, or ambitious to get stuff done early in 2024…who can say.) So, today’s focus is handling the full steam ahead of the New Year charge.

Acknowledgment

Like clockwork, every year in January, the gyms are packed. Recruiting (usually) kicks into high gear as new annual budgets open up and everyone returns from the holiday break. And those returning to the office have a renewed vigor to dive back into work. It all culminates in a lot of action, but what progress? 

Some people set annual goals before the New Year celebration, while others wait until after, but no matter when you set the goal, the question is how you will track and obtain those goals. Many frameworks exist – OKRs, KPIs, MBOs, BHAGs, etc. Ultimately, they are all just tools. The question is how to communicate those goals so that they’re understood clearly and how will you track the progress to know if things are working.

I know this will ruffle some feathers, but I believe OKRs are the worst form of goal tracking – except for all the others I’ve tried. I appreciate OKRs for their inclusiveness when you take the time to communicate high-level objectives and listen as the objectives and key results (the O & KRs) trickle back up. It takes time to get them right, which takes planning and preparation. But, if you 1) avoid setting overly aggressive Key Results (realistic goals work fine, and you can even recognize overachieving), 2) allow your team to adjust OKRs (within reason) when appropriate, and 3) don’t abuse OKRs by driving them to the individual level or use them for individual performance management, I believe you’ll get a lot of mileage out of OKRs. Here’s a good tip (5m read) for teams trying to improve their OKR game.

Mistakes were made

Mistake #41 is missing week 41. Due to the aforementioned busyness of the New Year, the week just flew by, and I didn’t get a newsletter published. 

More mistakes were made

For week #42, I wanted to discuss something personal. My wife and I have been married for over 20 years, but only in the last year (since the layoff, really), have we taken the time to collaborate deliberately. In the hecticness of raising four kids (yes, really) between the ages of 8 and 16, we had gotten into a routine of drive-by co-parenting. What I mean by that is that we were just rapidly throwing out items for discussion/planning/execution as we thought of them, rather than being intentional about how we planned our lives. Starting last year we moved to a model where we have a weekly meeting to discuss how things are going, and I borrowed heavily from a structure we refined for team meetings. It looks a bit like this:

Agenda

Agenda items that we have not yet scheduled, discussed or returned to. Copied to the Notes section each meeting as the start of the agenda for that meeting. This can be sorted, or sorted at the start of each meeting.

• Item A
• Item B
• Etc.

Action Items

Updated each week with the set of action items that are still remaining, due dates, assignees, etc.

Mine

• Item 1 (Jan 15)
• Item 2 (Jan 31)

Hers

• Item 3 (Jan 16)
• Item 4 (Feb 1)

Notes

Running history of meeting notes. Dated. Completed action items since last meeting are copied here.

Jan 10, 2024

• Item A
  • Notes from our discussion of Item A
• Item B
  • Notes from our discussion of Item B
  • Decisions are noted. Action items are too, and then put in the lists above.
• Completed action items (items completed since the last meeting, or in this meeting.)
  • Item 5 (Jan 1)

This structure was excellent for team leadership meetings, 1:1s, and other meetings. The only thing not covered here is “quick discussions” and “longer topics.” Pulling quick discussion to the top, and more extended topics get a scheduled date for discussion (along with assigning pre-work if needed to attendees,) makes sure that there is dedicated time for discussions that might otherwise always get pushed out.

Fun

This week’s post will be extra short. It’s late, and we’ve been busy celebrating Christmas and trekking all over the United States to see family. I just didn’t want the streak to be broken, and we’re at 40 weeks now, which is no small thing. I hope everyone who had a joyful Christmas (if you celebrate.) And for those celebrating other holidays this time of year (Kwanzaa, Hanukkah, or something I’ve missed,) I hope you enjoy a wonderful time of food, friends, family, and fun. As we wind down 2023 and look forward to 2024, I hope you look on with excitement for good things to come.

Encouragement

I have no idea what 2024 holds. I’m not one for resolutions or predictions. Here’s what I am hoping for, though:

1. A return to a more normal tech industry (reasonable hiring and growth.)
2. A gentle recession (if any) that doesn’t cut too deeply, given how many are already hurting.
3. Incredible new opportunities for everyone who was laid off that perfectly utilize their skills.

Mistakes were made

People keep asking whether I’m enjoying the contracting work, but one area I’ll need to better plan for if I’m gong to do this long term (e.g. beyond 2024,) is planning for holidays. I’m unsure whether I should plan my holidays and announce them to my clients ahead of time (with a commensurate rate cut that period,) or just get extra work done ahead of time and/or afterward to address the downtime, or something else. Whatever it is, I know that I need that downtime and I have to plan for it. This week has been a much lighter week on the whole—lots of family meals, gift exchanges, and travel, which ate into the time for work. I am looking forward to getting back into the deep work the New Year inevitably brings.

Fun

Happy New Year everyone!

It’s one week until Christmas (Merry Christmas!), and the last week of Advent is focused on love. The thing that comes to mind is how much I had a job I loved for nearly seven years at Indeed. It was one of the most significant losses I experienced when Indeed did its layoff. I wasn’t sure that I’d be able to find another role like it. I interviewed for some good companies and exciting roles, but ultimately none of them panned out, and none had the breadth of innovation I was hoping for. I’m sure I could have fallen in love with them had I gotten the offer and taken up the opportunity, but they didn’t look exactly right (at least from the outside). 

Contracting as a fractional CTO has been a steep learning curve, which I enjoy immensely. It has also come with challenges. Most notably, I miss working with my fantastic team from Indeed. We hired incredible people and gave them a lot of opportunities to lead how they saw fit, and it (generally) worked out well. Having the support of people who challenged, complemented, and questioned you makes for better products and a great workplace. I have good partners for my current contracts, but there’s something about it being temporary that has me wondering if they’re holding back.

Love Encouragement

I’ll start with a caveat. What little I know about dating is so outdated as to be useless. My wife and I met in High School, where we started dating, and we’ve been married for 22 years. So, this will not (intentionally) be dating advice, YMMV. That said, after countless books on love, marriage, raising kids, and more, the clear and consistent theme is that you don’t “find love” or “fall in love.” Even if you did, it’d be just as easy to “lose it” or “fall out of love.” You see, in the long term, love isn’t a feeling or a thing that happens; it’s a commitment, a decision.

This post in PyschCentral (6m read)talks about the four essential components of enduring relationships, which every job seeker (and many dating relationships) is looking for—attraction, connection, trust, and respect. I can see how, in my history of falling in love with companies and roles, I moved through each of those stages, and I can also see, in most cases, where those relationships eventually broke down.

I hope you find (or have already found) a company and role you love.

Loving too much

Sometimes, you drink too much of the Kool-Aid. I’ve been guilty of this. Having so much loyalty to the company and mission that you turn a blind eye to the changing culture and team around you. Every company evolves as it grows from zero to one, one to a million, a million to a billion. Any company that fails to evolve during that time would fail to succeed at the next level. Unfortunately, it’s like the adage about a frog in a pot of water. You either slowly boil, or you must stay awake to the temperature changes and decide when to get out.

The market is abnormal right now, so leaving is incredibly challenging for many people because it’s taking far longer to find their next role, but being ready to leave and leaving are two different things. Being ready to leave means you know it’s time, you’re extracting the last bits of learning, network, and expertise you can from that role before moving on. It’s all about making a plan, not just for where you’re going next, but for what you want to (legally) take with you.

A few quick tips on measuring the temperature of an organization and knowing when it’s time to leave. Ultimately, these are a gauge of the autonomy, mastery, and purpose that Daniel Pink points to in Drive:

1. If you find yourself less effective – you push for change but are nearly always met by more pushback than you can overcome.
2. You’re burning out – you put in more and more hours, but for little to no additional marginal gain.
3. You’re not gaining new skills – you’re always doing the same things and never learning new skills.
4. You’re no longer aligned with or believe in the purpose – you’ve lost your passion for your work.

Of course, plenty of other reasons go unstated here: you’re grossly underpaid, the work environment is toxic and much more. Depending on the severity, they might be reasons to leave immediately. Taking a regular assessment once or twice a year of how things are going is a simple temperature check. Having outside mentors and advisors you can connect with is another excellent way to look in the mirror and see what is happening.

Fun

Week three of the Advent season is a focus on joy. I know that when you’ve been laid off, that joy can be in particularly short supply. That’s a large part of why I include the “fun” section at the end of each post. I found during COVID that ending each day with a few /aww moments helped me sleep better and feel more content overall. Certainly, it was better than ending the day with more doomscrolling.

The truth is that joy runs much deeper than just a simple cute kitten or funny animal video. Joy is a deeper version of happiness or pleasure. It’s something you can experience even in tough times. Greg Anderson, a cancer survivor and prolific author, sums it up well 

“Focus on the journey, not the destination. Joy is found not in finishing an activity but in doing it.” 

While we focus on getting new jobs, starting new jobs, and running our business successfully, we have the opportunity to manufacture joy. Joy for others and ourselves. Taking time to be thankful for all the things we have can help us enjoy them all that much more. May you have a joyful Christmas and a wonderful holiday season.

Encouragement For the Newly Laid Off

Companies are continuing to layoff workers, even in December, in contrast to last year where layoffs dropped by 80% from November to December. The layoffs are also continuing to affect other areas beyond technology companies. For those who are experiencing this for the first time, or are newly laid off again, you’re not alone. Many people experience a layoff sometime in their career. There is a wealth of writing out there to support you in your personal growth, reflection, job search, and more that comes. Find support in your friends and your community. Start something new right away and stick with it. Hopefully you’ll be re-employed in no time, and you’ll have added a new skill.

There is the old adage that if you just get 1% better each day you’ll be 37X better after 365 days. And while that’s solid math, the truth is that humans don’t grow linearly, let alone exponentially. This article gives some much more practical advice (12m read) on improving yourself: pick something to dramatically improve, something to care less about, and something to improve somewhat. Reinforce your work with tracking, baselines for your efforts, and incremental improvements to your process/goals. It’s almost New Year’s resolution time, there’s a lot of great inspiration in here for 2024. 

All Work And No Joy Makes Jack a Dull Boy

Last week was brutal. We were double or triple booked nearly every night and had three(!) sports tournaments (for two kids no less) on the weekend. But that week is behind us. On to the next. 

Not so fast. I got up Monday morning and hit an absolute brick wall of “nope.” I had no motivation. I had no energy. I had no creativity. No patience. You get it. I needed rest. 

I didn’t take the whole day off, but I did take a much needed coffee break to catch up with my wife. I was in bed on time Sunday and Monday nights to recharge my body. I enjoyed a slow meal at home, as opposed to eating another meal in my car. I sat and enjoyed chatting with my kids and tucking in the little ones. I’m not fully recharged, but my motivation and energy are returning.

I can see in hindsight that I was burning out. I’ve seen this in employees, peers, and myself previously. This time of year can be very stressful: planning 2024 goals, reviewing 2023 performance, juggling time off for yourself and others, not to mention all the family commitments, holiday parties, Christmas concerts, and so many more things. Recovering from burnout can take a while (12m read, but I skimmed TBH), but with active effort and support the timeline for recovery should be manageable.

Fun

We’re now in the Advent season in the run-up to Christmas. Last week’s focus was on hope and this week on peace. For those who are still job searching, those whose company is considering an additional round of layoffs, and those accelerating in new roles, the thought of having hope for the future and peace at the moment is a welcome reminder. 

I know personally this week has been anything but peaceful. We’re wrapping up baseball season, in the thick of basketball season, doing some college research, traveling for a college showcase, and attending many end-of-year school events. We’ve been double and triple-booked every evening after work this week, leaving piles of dishes, a smal mountain of laundry, and scrambling to get lunches together each morning. Thankfully, we are looking at next week being a lot more relaxed. We’re leaning hard into the hope that next week will be much more restful, helping us recharge before the Christmas holidays.

On the work front, I’m now booking contracts for 2024 and completely oversubscribed. There is so much opportunity for additional work beyond what I can do in my limited workdays. For now, I’m turning down work to maintain some balance on the personal front. There are so many great teams and projects, and I’d love to spend more time with all of them.

Hope is contagious

Hope in the workplace is often a foreign concept. Many organizations think about vision, joy, and other attributes. This HBR article (6m read) shows how impactful hope is on organizational morale. The concept of “emotional contagion” – the transfer of moods amongst team members – was a great way of summarizing what I’ve seen and experienced. Teams that focus on the positive impact and future opportunities perform better than those that focus on misses and mistakes. There’s a place for reviewing mistakes and learning from them, but the use of blameless post-mortems and shame-free five whys can be done in a way that extracts learnings without demoralizing the team.

Saying no brings peace

As mentioned above, this week has focused on saying “no” to contracts. It feels strange to leave money on the table and say no to work that I know I can do. But, coming from a larger organization where I could time slice my project load and delegate to my competent team and now operating as a solo operator has been a significant shift.

Additionally, coming out of my first holiday week as a contractor forced me to reevaluate how I communicate timelines around time off. I felt like I didn’t get enough time to get the work I needed done, and simultaneously, I felt that I was working more than I wanted during the holiday week. That’s an entirely normal feeling for contractors, I’m sure, and for startups as well. It’s just an adjustment that I’m in the process of making. Ultimately, saying no to things has brought me more peace as I focus on delivering a great product for the teams I’m already working with.

Fun

I’m flying to Kentucky this week for dedicated work and user research with a fully distributed startup team. It’s my first “work trip” in several years. I’m excited to spend time in person with the team, and I have high hopes for the work we’ll accomplish over the three days together. I’m incredibly excited because the holiday week (and associated sickness the kids picked up) felt so particularly unproductive. I have high hopes for what we’ll accomplish by the end of the year but fully recognize that the time remaining before 2024 is quickly fading.

This week, I wanted to dive into the speed of life right now. I know how busy it can be when you’re fully employed, but strangely, being unemployed often felt even more busy. Having some structure to your days, plans/goals for your time, and metrics/measures that guide you to success will help to make sure the time is used well.

Flying High

This article on slowing down and enjoying life (8m read) more doesn’t have any particularly astute observations, but had several helpful reminders for me: driving the speed limit (I took this more metaphorically than literally, although they clearly meant it literally) and make time to have fun.

Flying requires getting off the ground.

I’m letting a fear of failure hold me back from starting. I have partnered with Emergent Execs (an executive coaching company in Austin) to create a new Tech Exec Accelerator. We’ll be launching the course in February of 2024. I have talked to several other leaders who have shown me that creating video content to promote and draw attention to the course and get it out beyond my network will be critical. 

But…Video is daunting. Social media is a whole landscape to learn. I need to take my own advice and just “get started and get better.” So, I’m putting it out here today. My goal is to get one short video out into the world by this time next week. 

Fun

Shorter than usual as we have a short holiday week here in the US. Happy Thanksgiving, everyone!

Multiple job seekers receive the dreaded “we’re pushing this role to 2024” message this time of year. It’s just that time of year. Between busy holiday schedules, questionable budgets, and changing market conditions, many companies feel it safer to delay hiring for a few months. Other companies are laying off again, many for a second or third time.

As a job seeker or a contractor, it is like pushing rope to drive things forward. We don’t own the timeline, the budget, or the scope of work, so you have to focus on what you can control—putting plenty of new work into the top of the funnel, doing your best, taking care of yourself mentally, and looking at the long term. 

The other perspective is that pushing this boulder up the hill has gotten much more challenging. The exhaustion and weariness of being ghosted, rejected, and spending time on fruitless searches wears on you. The time spent in conversations with companies who aren’t ready to commit to a contract drags at the time you could be spending elsewhere. But we must keep pushing because it’s what we can do. 

Pushing Mistake

As we headed out for the family Thanksgiving road trip, I kept pushing for more details on when we were leaving, who we would see, and when we’d be coming home. I learned long ago that these sorts of trips are more an exercise in flexibility than planning and execution. So, a few quick tips on staying flexible:

1. Remember the goal – quality time with family.
2. Remember the non-goals – equal time with each family.
3. Set some high-level objectives – quality experiences at each stop and reasonable amounts of driving.
4. Let the rest sort itself out – there will be inefficiencies (Mcdonald’s breakfast, extra grocery store trips, etc.)
5. Lean back and enjoy – enjoy the season.

Fun

Regular readers of this journal may notice another rename of this journal. The first was back in week three (from “Ex-Indeedian Journal” to “Layoff Journal”), as I worked to expand the audience beyond those laid off by Indeed. I wanted to make valuable content for ex-Microsoft, ex-LinkedIn, ex-Meta and many others laid off in early 2023. This time, the rename is meant to capture that while I was laid off in March, it’s no longer helpful (or completely accurate) to continue dwelling on the layoff and unemployment. Let me explain.

First, it’s no longer fair to refer to myself as unemployed. I’ve been working on a contract since the first of October, providing them with product leadership, strategy, and even some user experience design for a new product. It’s beginning to set in that this could be a new normal for me, at least for this season.

Second, it’s probably no longer fair to keep myself in the “laid-off” box now that I have gainful employment again. If that ended, I’d have to think of myself as looking for my next contract or winding down my fractional-CTO role, not back to being laid off. While it’s not the plan I had in mind, it’s clear that this is the next step I’ve taken.

So, let me introduce Weekly Mistake – a weekly journal/newsletter capturing my thoughts and learnings each week as I navigate this post-full-time-employment world. I’m sure I’ll eventually end up fully and gainfully employed somewhere again, someday, but for now, let’s jump into the gap and see what we can learn.

All is fair in love and consulting

I’ve talked with a few people considering starting their consulting work (Product, CTO, Design, and others) and thought sharing a few notes from my start might be helpful. 

I stumbled into fractional CTO work in September. I had explored it in April & May but ruled it out for a few different reasons:

1. There were jobs to apply for, and I wanted a paycheck and benefits.
2. The fractional CTO life looked very solitary.
3. The process of finding contracts seemed daunting.

However, in September, nearing the end of my unemployment benefits and with the end of the severance package in sight, I was approached by a venture capitalist I had met previously. He and I had talked through a company he was considering investing in back in May, but it has yet to materialize. He had another idea he wanted to explore, and he wanted a partner to help guide his team on the product discovery side. This was near and dear to me, given my years of experience in the Indeed Incubator, so I agreed to take on the opportunity. I can’t say much about the company or product at this stage, but I can tell you more about my experience as a fractional CTO.

1. Yes, there were (and are) jobs to apply for; however, having been to the final round a few times and getting rejected leaves me with little confidence in landing a role I’m genuinely passionate about. I like to believe I could have found a role, but I wasn’t willing to just take any old role and to be honest, the reality of the job search seems to argue against my belief.
2. The fractional CTO role does have a lot more heads-down time for writing and thinking, but it also comes with a lot of collaboration with various stakeholders and partners. I still very much miss the great team I had at Indeed (and I connect with several of those folks as often as time allows.) However, this new freedom to pick and choose who I work with, on what, and for how long also has its perks. I haven’t felt lonely yet. The job search process felt more lonely than consulting, to be honest.
3. Thus far, the process of finding contracts has been very serendipitous. All of the possible contracts I’ve been exploring and discussing have come through referrals and my network here in Austin. I’m thankful for all of you and the help in finding opportunities.

Ultimately, this was considerably more doable than I imagined. I don’t know how long I’ll keep it up, but for now, it is working. I have health care coverage (thanks, COBRA). I have contracts. And I am learning a lot. For anyone considering consulting, please reach out, I’m happy to share more tips.

The Mistake

While bootstrapping this consulting business, I felt I didn’t have the luxury of saying no to anyone or any project. I kept every possibility open for as long as possible to see if it would materialize and to keep my options open.

Unfortunately, some teams weren’t ready to pay for my support. Some couldn’t afford it as they were still pre-revenue and bootstrapping. Others were looking for a skill that I was not incredibly versed in. Whatever it was, the time spent with them would have been wasted. However, I firmly believe in making mistakes to facilitate learning and growth. 

I’ve refined my intake process to shorten the time from meeting to proposal and pricing. I’m more deliberate about asking where their current funding levels are. And, with some revenue coming in, I can consider more interesting deals involving potential equity in the future.

This read on the sunk cost fallacy (14m read) is a good reminder of the principles behind the fallacy, techniques for avoiding it, and more. In this early stage of a project, sometimes doing things that don’t scale or may not pan out is just as valuable to help learn what areas are working. I’m still finding the “negative edges” of my abilities, the areas that I’m not well equipped to help.

Fun

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