With two startups trying to launch and one trying to raise a round of funding, things are hectic right now for a team of one. In a typical year, I’d be volunteering as an election clerk, happy to take calls with new startups that are looking for a user experience interview, and volunteering with my kids’ various activities. When I was a Senior Director running an 80-person engineering organization, my calendar was often booked completely solid from the start of business to the end of the workday, and at least one day a week booked again from the kids’ bedtime to my bedtime with Tokyo meetings. It was standing room only in my calendar.

One of the biggest realizations I had over the last few years is that managers and executives need maker time, too. Scheduling my time to work on proposals, budgets, performance reviews, and more was a requirement. I had to actively manage my calendar, not allow it to manage me. I’d take a stab at how long a particular task would take, block out time on my calendar to accomplish it, and invariably move that around as meetings came onto my calendar. The great thing about seeing it visibly on the calendar as I rearranged things to accommodate people was that I could visually (and viscerally) know I was delaying my deliverables and work. 

Now that I’m solo and working with several startups, having ChatGPT and CoPilot has made me much more productive, but I still have to pay attention to my daily, weekly, monthly, and quarterly goals. I’d be lost entirely without those goal trackers and a to-do list. Occasionally, I’ll get away from tracking and prioritizing things and find myself just flailing from one urgent item to the next with loads of anxiety. Sitting down, writing everything down, prioritizing, delegating, dropping, and executing on items always gives me more peace, and things get back on track quickly.

Slipping Into a Traumaversary

As we approach the one-year mark since the Indeed layoff, I want to warn about the concept of the “traumaversary.” It’s a well-documented (even if not wholly provable) phenomenon in raising adopted children and others who experience significant traumas. Many situations can trigger feelings of loss, anger, sadness, and more throughout the year. I’ve seen birthdays, anniversaries, vacations, and so much more trigger those feelings. So, as the first anniversary approaches, plan to do something for yourself. 

Slip or Slide?

One of the startups I’m working with has offered me the full-time CTO role starting at the end of my current contract. Having contracted for almost six months, I’m debating whether to remain a fractional CTO or dive head-first into a dedicated role. I love the team. I’m enjoying the product. We have funding and will be on track to secure more this summer. All signs point to joining. I could just slide right into that team quite easily.

But being a fractional CTO has a few perks. The cash compensation is better (if I can continue to secure enough contracts). I have more control over when and how much I work. I also get to work with several teams at the same time. 

I’m torn between the two opportunities. So, it’s time to consult my “personal board of directors.” I have a few close friends I regularly meet with when I have big decisions. We catch up other times to hang out and chat about other stuff, too, but occasionally, I will ask them for lunch, beer, or coffee with a clear agenda. My board of directors comprises several people from different perspectives, and each plays a slightly different mix of roles in my decision-making process.

A few are close friends with a similar spiritual background, and they help me consider how my relationship with Christ may guide my decision. A few others know the business and technology scene inside and out and can help me guess the challenges I’m likely to face and my chances of success. Last, but certainly not least, a few others give me guidance on choosing well with regard to my family and obligations to my children. 

I’ve had this kitchen cabinet for years now, and they’ve helped me through a lot of hard decisions. I highly recommend the process, and if I can be this sort of mirror for any of you please reach out.

Fun