Weekly Mistake #61 - Busy and not thinking

I’ve always had a hard time writing while working full-time. I put (nearly) all of my waking energy into the business I’m working for, with the remaining energy going to family. Additionally, sharing the internal details of what I’m working on feels like “trade secrets,” “insider information,” or other content that would be owned (or at least reviewed) by my employer. On top of that, let’s be honest: working in public is scary.

One of the best things about writing a weekly newsletter was how it forced me to slow down and think. Of course, I was busy filling out applications, interviewing, networking, and more, but I still made the time to think holistically about where I was and where I was going. The contracting life from October to May was a unique blend of full-time work with a lot of autonomy, making it a bit harder to find the time to write, but ultimately, I (mostly) kept up the pattern.

Joining?Thurgood?full-time in June, I put writing externally aside as I felt I no longer had a good perspective to help those laid off and needed to focus inward on building a new business. I recently reconnected with former coworkers and realized I hadn’t publicly announced my move from fractional CTO to cofounder & CTO. Much of my writing has turned inward as I’ve worked to help crystalize and document our strategy and experiments. Now that I’m a few months in, I have some time and am ready to surface some of the work I’ve been doing. I doubt this will return to a weekly newsletter, but it should be more regular again.?

Thinking through writing

I’ve read many times that “leaders are readers.” While I agree you need diverse opinions and thoughts to shape your leadership and direction, reading is also helpful as it shapes your writing. Writing is key in capturing, crystalizing, and synthesizing your thoughts. Writing slows you down to evaluate and test what you’re saying. Let’s break this down:

• Capturing - Thoughts can be so fleeting that pausing to write slows you down, and if you give yourself the liberty not to edit as you write, you’ll find several ideas floating around in your brain. Putting them down somewhere frees you to let them go and see if they resurface, refine, or die on the vine.
• Crystalizing - Because writing is slower, you can tighten your thinking, test your opinions, and see the holes in your thought processes. First-draft ideas are still just first drafts but replayed in a second draft, email, or speak to others, are much more refined and ready for debate and consumption.
• Synthesizing - Putting down your ideas allows you to see the patterns between them or to combine two ideas into something that’s even more powerful than the original parts.

Mistake #61 - Thinking inside the box

For years now, I’ve been part of a much larger organization, and I could (generally) trust others to run the finances, sales, and other key parts of the organization. As a founder, those are (partly) my responsibility, too. Once we secured an initial pre-seed round of funding for Thurgood, it was easy for me to go completely heads down on getting the technology in place to support the rest of the company and neglect the broader details.

As an engineering team, we did a good job keeping things lean and shipping early. Unfortunately, I failed to create a concrete enough picture of the engineering budget to forecast our spending through contingency plans. As we launched to public users in June, we quickly began to encounter a variety of significant headwinds. Our user base did not organically grow, our application was not sticky, and our user acquisition channel was slow. Of course, additional experiments would be needed to get these rolling, but the timeline for securing additional funding was slipping beyond our runway.?

While running the Incubator at Indeed, we had a rule of thumb for engineering teams not to build anything that wouldn’t move the needle on their current runway or one runway beyond. That’s a luxury only afforded to corporate startups. As a venture-backed startup, our vision is even more narrowly focused, and unfortunately, the length of the runway is the biggest variable we have control over. We had to lengthen the runway as much as possible to buy time for our experiments on growth to be run and had to close out our contracts and lay off two very qualified full-time engineers.?

So we’re back to a group of founders, each pulling as hard as we can on this rock to get it rolling.

Photo by Aaron Burden on Unsplash