Weekly Mistake #52 - #57 - Catching Up

I’m several weeks behind in writing and wanted to jump back into it, so today’s newsletter is a collection of four short notes rather than the previous format (not that I was ever super strict about the structure of this newsletter.) I hope you enjoy it.

Week 52 was an emotional one for me. Seeing the calendar roll past March 22nd (the one-year anniversary of Indeed’s layoff) meant recognizing that it’s been a year since I felt stable in my income, work, and career. There were a lot of emotions wrapped up in that week, and I wasn’t ready to write about them. 

Photo by Andrew Krueger on Unsplash

Now that I have the distance of a few more weeks, it’s easier to see that I had put a lot of my self-worth into what role I was playing and the company I was working for. Much like COVID taught me about the value of connection and networking (a story I can share or re-share in the future,) the layoff gave me more clarity about what matters in my work. Ultimately, it’s about working with people I like, on a mission I value, and making tangible progress. Those things were less and less the case for the last year or more of my time at Indeed.

While I’m not 100% back to where I was at Indeed, my new roles have given me a chance to work with some great leaders on missions I am excited about and to see businesses formed from nothing. I’m learning (a lot). I’m enjoying the work (a lot). And I love the teams I’m working with. There is not much more I could ask for.

Living Life at 100 MPH

The last two to three months have been extra chaotic. With the fractional CTO work kicking into the highest gear in February and our kids’ Spring sports kicking off (often before Winter sports had fully wrapped up), we went from standard four-kid-family busy to ultra-busy. But this isn’t me #hustle bragging. This is me being honest.

I’m exhausted and behind. I wanted to launch HeatCheck and acquire users. I wanted a second startup to move away from Excel sheets and to a custom product to run its business. I expected to be running a cohort of executive coaching sessions. And I wanted Thurgood ready to launch by this month. None of those things have happened on my schedule. They’re all significantly moving along and approaching our goals, but each still has its hurdles.

On top of that, one of the first engineers I hired at Indeed passed away suddenly at the beginning of March. It was a real shock and a reminder that it was time for simplification. While the contracting life has paid the bills, and I’ve learned a lot about it, I don’t think it’s my long-term play. I’m starting to trim back the contracts and not actively seek others. I want to see each of these things across their respective finish lines. I want to reconnect with friends. I need to get back to working out regularly. I have to have some margin in my life. So that’s my next challenge, trimming and replacing with life-giving activities (friends and exercise in particular.)

Launching Early

Two startups I’m working with will launch very soon but look different. The bootstrapped HeatCheck is approaching a marketing launch that will hopefully begin to bring in users and revenue. Thurgood is about to kick off its pilot and see the first users on the platform as well (although revenue will likely lag a bit behind that pilot).

Reid Hoffman is often quoted as saying, “If you’re not embarrassed by your MVP, you’ve launched too late.” In the case of HeatCheck, I’ve been partnered with that team for over a year now, but the nature of a bootstrapped product is that every penny spent comes from someone’s pocket, so you’re constantly wondering when the right time to get real users into the product would be. Thurgood is VC-backed, which has allowed the team to run faster (hiring a few contractors to start and soon a founding engineer) and the marketing budget to do a pilot kickoff next month.

Both will still have a handful of rough edges and feature “cul-de-sacs” at launch. We’ll keep working those out based on user data and feedback. That will be a fun and exciting new phase for both projects. I can’t wait to get there!

Recovery Weekend

No baseball last weekend meant a recovery weekend. Usually, it’s two baseball games on Saturday and one or more on Sunday (play until you lose). We still had a handful of activities in the week leading up to the weekend off, and of course, there were still a few things to do on the weekend. Still, on the whole, it was things we wanted to do that allowed us to catch up on housework, see Dune Part Two in the theater, and plan a few upcoming family activities. Now that the weekend is nearly done, I’m looking to the next few weeks and realizing that it will be a full schedule between now and the end of June. 

We’re somewhat at the mercy of the kids’ schedules, but I think I need to schedule a “do-nothing” weekend every three months or so. Maybe the kids are still coming and going, but we arrange for carpools or plan for them to miss their activities that weekend as well so that, as a family, we can collectively catch our breath. I know Summer will naturally give us a few of these as there are fewer outdoor sports thanks to the Texas heat, and in fact, after some of the kids are dropped off for their various camps, we’ll get some quality 1:1 time with the remaining kids. So, even as busy as the summer looks, I’m looking forward to the recharge that comes with it as well.