I recently stumbled onto the work of Eli Dourado (@elidourado). The thread produced by a simple tweet (see my response) coupled with a recent article he wrote has fueled a lot of inspiration for me this week. Combine that with Elon Musk’s new XPRIZE for carbon capture, exploring discussions on Clubhouse surrounding innovation, and reading that NASA’s willing to buy regolith from a private company, and you’ve got the perfect storm for me—a scanner—to reevaluate everything…again.

In a moment of weakness and overwhelm, I emailed Eli laying out my dilemma about pursuing higher education and asked for some wisdom. I’ve been thinking since hitting send, and I stumbled onto a few key concepts that will help me. It was definitely one of those situations where once I laid it all out, the solution was easier to see—even if I couldn’t retract that email 😬

Paradox of Choice

I think about situations where I wish I had less freedom to choose. If only I didn’t have so many options, it would be easy for me to choose which option is best for me. That sounds nice at first, but is that what I actually want? Of course not.

Maybe even worse, I find myself wondering about the “what ifs” that can’t happen. What if we didn’t have kids, and I could spend today alone with my wife, I think to myself after a particularly difficult morning wrangling kids. What if I had moved to Seattle instead of Denver? The list goes on. It’s counter-productive exercises, though. I just have to remind myself that instead of dwelling on what could have been, how can I make my current (or future) situation better given my current constraints (kids, location, etc.). In fact, engineers love constraints. As one of my professors regularly said, on an unlimited budget, anyone can build a bridge, but an engineer does with the least amount of material possible.

So, in an era of FOMO, the real question becomes, “How does one stop keeping their options open?”

College

I’ve been through this situation (i.e. decision paralysis) a number of times. I remember flip-flopping almost daily for weeks on deciding between attending Boise State University (BSU) and the Virginia Military Institute. I chose BSU and thrived, but that only lasted for a year. I married a girl who taught middle school on the opposite side of Idaho.

I transferred to Idaho State University (ISU), and I resented it for my first year, because I had been comfortable. Ultimately, though, while I preferred the modern feel of BSU and being situated in a downtown area, ISU’s smaller-feeling campus consistently provided opportunities I never would have gotten at BSU. Examples include:

• Leading our ROTC program as the Detachment Commander
• Discovering and falling in love with economics because my double-major had to change when I transferred universities
• Serving as a student government senator for my college
• Winning money for two business ideas (SpaceSpace, Toast Dance) at Shark Tank-style pitching competitions

Career

My last year at uni, my wife and I narrowed down where we saw ourselves ending up. Picture a Venn diagram of where we’d like to live and where there is a high concentration of aerospace jobs. Seattle, Denver, and Boston were our finalists, and I started looking for jobs. I interviewed with those three states’ National Guard units, too. I continued to apply to jobs (totaling over 300; I kept track) but had no luck. Ironically, it wasn’t until I misunderstood part of the process and locked in my commitment to the Colorado National Guard that I could focus on a much smaller market of opportunities and land a job. In that case, “keeping my options open” hurt me, preventing me from leveraging my job search.

FOBO

Ironically, I relistened to a podcast (Spotify) on accident just yesterday, and it brought up FOBO: fear of better options. I usually don’t have an issue with FOMO—fear of missing out—unless I think about what rad companies like SpaceX or Relativity Space are up to. Lately, though, FOBO is what has kept me from committing.

General Patton’s quote comes to mind: “A good plan violently executed now is better than a perfect plan executed at some indefinite time in the future.” Everyone out there has a different path, and the devil’s in the details…of execution. At Lockheed, there are vice presidents with just a bachelor’s degree. Has that hurt them? Apparently not too badly. So in reality, the “worst” that can happen is that I get an irrelevant degree but have fun along the way.

There’s also a great parallel in marriage. In a world of 7.8 billion people, there is certainly a better match for you out there, but it’s more about what you invest in a marriage than the person you marry.

Segments of My Career

I’ve recognized a better framework for how to perceive my career. I’ve essentially split it up into 20-year segments, and while it will absolutely fluctuate, this exercise was helpful to take some of the mental load off of me in terms of constantly thinking about my career. I’ll also note that flexibility is key, as opportunities I never imagined will present themselves.

Building Technical Skills (26-46)

I graduated from college at the age of 26. If I stick with my civilian and military jobs for 20 years, I can retire from both at 46, locking in a dual-retirement and removing some of the risks of starting a business on my own. These years are also critical as I build technical expertise—particularly because I want to work on hard tech, not software.

I look up to young entrepreneurs, and I wish I could jump in and join them right now. Caleb Carr comes to mind. We’re the same age, and he’s the President and CEO of Vita Inclinata, a technology company innovating on stability for helicopters and cranes. I could be really jealous, but I recently listened to a podcast with Michael Dell saying he was motivated by Bill Gates and Steve Jobs, because they were 10 years older than him and not married, and he wanted a family.

Harvard Business Review also published an article in 2018 sharing that the average age of a startup founder is 45. That fits with my plan!

Leveraging Technical Skills (46-66)

While I would love to be a Forbes 30 Under 30 wunderkind, I have many competing priorities that I’m not willing to let go of. For example, Elon has been divorced several times. I’m not willing to let my marriage fail.

Once I’ve banked that double-retirement nest egg, I can break out and start a company to change the world. I’m following tech and startup news in the meantime, constantly jotting down ideas for addressing problems. In fact, I’m working on a few side-projects that could go toward saving for that future business.

Sharing Technical Skills (66-86)

After a lengthy technical career, I’d love to give back. I’m not the guy who loves differential equations or some of those knee-deep-in-theory courses. I’d love to teach at a university, though, exploring new ideas and getting others excited about their careers. I’m not even sure it’s possible, but it’d be so fun to teach a mixture of German, entrepreneurship, economics, ROTC, and engineering. I can dabble in all of my interests at the end of my life having “proved” and accomplished what I want to.

I’d also love to angel invest along the way, and maybe being at a university is the way to get the next generation involved in tech.

Acknowledgments

Thanks to Shalene Henderson, Abel Birk, and Matt Schock for proofreading and providing feedback.

Appendix: Vetting Ideas

• Tim Ferriss: Is this a full-body yes? Is this a no-brainer (don’t just ask if it’s a good idea)? (Podcast)
• Derek Sivers: If you’re not saying “HELL YEAH!” about something, say “no”. (Post)
• Jonny Henderson: What role is ego playing?
  • Example: If I could learn all of the content involved with a degree without receiving the credibility that comes with the degree (i.e. not actually graduate), would it be worth it?
  • My Northstar → “Because: Astronaut” → Is this getting me closer to astronaut or is it shutting doors? (Example: MBA vs. MS in AeroE)

• Misc

• • Have I considered: Good, better, best
  • Have I considered: energy management not just time management