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