On January 20th, 2025 I found out that I had been laid off. I have spent 10 years as a software developer / software engineer, and the last 3 at a "big tech" company. I truly have no hard feelings for the company, or anyone involved in the decision. I have a lot of respect for the founders, and will likely use their product if I ever have a use case for it.

I say none of this to disparage anyone at my previous employer, but simply to share my journey as I determine what's next for me, work to provide for my family, and hopefully inspire others who have gone through, or are going through, something similar.

Career History

I spent the first 4.5 years of my career at a small company of 20-30 employees that provided churches with videos and graphics. I worked as a full-stack developer, helping build the online marketplace where this media could be purchased; either individually, or through an annual membership. I am very grateful for this period. I learned a lot from my manager & coworker. Over time though, my manager moved into a leadership position, and my co-worker moved to a new company. This left me without peers, and with what felt like little room for growth. While working there, we had our first 3 kids, which led me to think about how we wanted to raise them, and ultimately led me to look for a remote job.

In 2019 I moved to a company that had been fully remote from the beginning. I believe the company size was around 120 when I started, with ~40 of those being engineers. I was with this company for 2 years, and though I do have critiques, in many ways, it was the best 2 years of my career. It was fully remote and had flexible schedules. I had smart peers that I loved working with and we were always sharpening each other. The company was also large enough for growth, yet small enough that it felt like we were all working towards the same goal. Then, in 2021, we were acquired by "big tech."

The acquisition was an exciting time! We looked forward to doing meaningful work, in a company that is considered by customers one of the best in its industry. Our founders also took care of us, ensuring that there was a job at the new company for anyone who wanted it, and ensuring that we all got a payout as part of the acquisition, even if we hadn't exercised our options. The other side wasn't quite as rosy though.

A large portion of our team was laid off within a year of being acquired. It was just after COVID, during a time when all big tech companies were laying off. I escaped that initial round. I've struggled to articulate exactly what went wrong for me after that though. I think it was death by a thousand cuts. There was a lot of moving between teams, projects, and areas of code, making it hard to master any particular area. There were expectations that I'd never experienced before, and little help in learning how to meet those expectations. I assume they were all things that would have been taught naturally when "growing into" my level from a junior level within the company, but that I hadn't learned in previous roles.

So far, I've not had success with interviews for the role of Software Engineer. I get it though. A certain level of experience is expected after 10 years in the field, but the past 3.5 years feel like somewhat of a career black hole to me.

  • While I have mentored junior engineers (mostly in Ruby), I don't have any big projects that I've led, which interviewers like to see. I also don't spend of lot of my "off time" on a computer. I have to look back 3-6 years to find projects that I'm proud of to talk about, and those were in code that I no longer have access to, so I have to go off of vague recollection.
  • While I have worked full-stack in the past, it has been a few years, and I lean more towards the backend. I need to spend some time sharpening my frontend skills.
  • While I have used C# (2-3 year college internship), C++ (college classes), PHP (hobbies), I'm not near the polyglot that most places like to see. Nearly all of my professional experience has been in Ruby.

Entrepreneurship

After applying for the software engineering roles that seemed like a good fit, I've started looking for other things I could do. I've debated about whether I want to sit behind a computer, working a 9-5 for the rest of my life, but I also don't see myself as having a lot of marketable skills away from the computer. I've wanted to own my own family business, and have made a couple of attempts, but have yet to find anything that has stuck. I also have ideas around my interests, but need to figure out how feasible they are in our area, and need to figure out how to fund them.

Real Estate

We've had two rent houses in the past. One made a profit, but the other lost money. In the end the second took too much time & money, and we sold both to break even. I've outlined our experience with each below. I wouldn't rule out doing real estate again, but we'd need to be a lot smarter about it. It's definitely a long play and not quick money, but I do believe it has great potential.

Rental One

  • Built as our primary residence just before the COVID price increases. Converted to a rental after outgrowing in ~2 years.
  • Newer neighborhood, filled with a mix of owner-occupants, as well as renters.
  • Rented to a young couple who, on paper, didn't look like they could make it work, but who I had a good feeling about. They turned out to be excellent renters who paid on time and were great at communicating with us.
  • The neighbors didn't like them and were constantly nitpicking.
    • Since we had lived there, neighbors had our numbers, and passed them out to others on neighboring streets as well.
    • We got lots of reports about things that aren't really a landlord's responsibility. They should have talked to our renters directly, as neighbors, if they had a problem.

Rental Two

  • Very old, and we purchased for too much right after the COVID price jump.
    • Couldn’t rent for the amount we needed to. We pretty much just covered the mortgage, with no room for maintenance expenses.
  • Couldn’t find good renters.
    • Only people interested trashed the place. The lease specified no smoking or pets. The renters smoked constantly, and raised two pit bulls and a litter of puppies inside.
    • Rarely paid on time. Had to give multiple reminders and charge late fees.
  • Had been renovated on the inside, but it was just "lipstick on a pig."
  • Previous contract had been withdrawn after receiving inspection report.
    • We bought the inspection off of the previous owner, and should have backed out, but our agent told us that that particular inspector was a "deal killer," and was too critical.
    • We should have trusted the report.
    • Had many issues with plumbing and electrical in the one year we owned it, and I was there all the time dealing with it.

Food Establishments

I have absolutely no experience in the food industry. I think there are things I'd like about it, but I'm sure there are other parts that are less than stellar. Some ideas I've had are:

  • Coffee Shop would be my top pick for this category. I enjoy working from coffee shops, and enjoy specialty coffee. I also enjoy conversations that can happen serendipitously as people drop in throughout the day. One of my favorite coffeeshops in a city about an hour away also has a co-working/event space on the side. Unfortunately, our town has too many coffeeshops as it is, and this requires experience that I don't have.
  • Local Hamburger Joint would be a close second. One of the things I miss most about city life is a good hamburger. My favorite hamburger place is a small local chain about an hour-and-a-half away. I think it would be cool to own a franchise, just to get a location closer to me. I don't think they franchise though, and again, I don't have the experience.
  • Natural Ice Cream & Soda Parlor - My wife and I try to avoid commercial soft drinks because of how bad they are for you, however, after visiting an old-fashioned ice cream parlor & soda fountain in Colorado, we thought it might be cool to have one with natural, made-in-house colors/flavors. This would require less experience, but still a lot of capital.
  • Catering parties with cooked to order hamburgers. I saw this done in the city, but as a friend pointed out, in rural areas like where we live now, the men take pride in grilling themselves when throwing a party.
  • Ice Cream Stand / Snow Cone Stand / Lemonade Stand / Cocoa Stand - Now we're getting somewhere. We could have a primary location to park the trailer, but also take it to big events like the seasonal festivals that every town has. This actually seems feasible, but we're still trying to determine what kind of earning potential it would have having looked at the numbers for one that has ran in our area, it won't make enough.

Home-based Food Business

  • I know many people that bake bread and sell cookies. My daughter has been trying to master banana bread & pumpkin bread. I think this has potential as a side hustle to bring in extra income, but don't see it providing for our family.

Niche Business Directory

  • I initially wanted to build a directory of Christian-owned businesses, for people that wanted to keep their dollars within the Church.
  • I've considered that this could be expanded to other niches as well (veteran-owned businesses for instance).
  • I'm not sure how marketable this is though.

Digital Coupon Card

  • In college, high school fundraising clubs would come by selling discount cards for local businesses. I've considered digitizing this with a website/app, and getting those same clubs to do the selling for me, and we'd split the profits.

Maker Space

  • I seem to always be finding a new interest, but many of them revolve around making things. It turns out that this is a key attribute of ISTPs. I know maker spaces are popular in cities, but I'm doubtful whether our small college town could support one.

Etsy Shop / Local Shop

  • Sell custom mugs, t-shirts, laser-engraved signs & gifts, etc on Etsy - This goes along with those varied interests that make me want to have a Maker Space.
  • Two-for-one business if I had the equipment & space, but still I'm still not sure how to make it profitable.
  • I'm trying to test the profit potential with 3rd-party printed items that I've designed.

Technical Focused Startup Incubator

  • I've thought it would be really cool to bring college students together from both a business/entrepreneurial focus & a technical/computer science focus, one supplying the ideas, and the other being able to execute on it.
  • It would likely require mentorship from someone further along in the business/tech space, whether that's professors, or other individuals.
    • In exchange for their mentorship, they would get a percentage of ownership in these new businesses.
    • After writing this down, I found others are already doing this. That doesn't mean that it couldn't be done again though. I think it would be cool to work closely with college degree programs as a pipeline of potential candidates.

Late-night College Hangout

  • I miss the days that our local coffee shop stayed open late. I used to live a few blocks from it, and had young kids who went to bed early, so I was often able to work there until they closed. I loved the buzz of activity around me as college students play board games, etc.
    • That coffee shop now closes at 6, and I'm not aware of any place in town that acts as the social hub in the evenings, as it once did.
  • I don't see how to make this work with older kids now. I need to be home in the evenings for dinner & bedtime.

Classical Education

  • I'm passionate about giving a classical education to my kids, and I want to give one to myself as well. Unfortunately, when I was at a full-time job, I rarely found the time to do the reading that I wanted to. I've considered whether I could monetize this in some way (online or local classes), that would allow me to spend more time on it.
  • Just recently a friend offered me a job as a teacher at a classical Christian school. Unfortunately, it pays slightly less than half of what we need in a year. I'm trying to find ways that I can make the difference during the summer, and on the Fridays I'd have off during the school year.

In the meantime

It takes time to start a business. For now, I'm trying to come up with ways to quickly start making enough money to cover our bills, then I can work on business ideas as time allows.

D2D Solar Sales

I explored door-to-door solar sales. A few years ago, I never would have never thought that I would consider this. A couple things I liked about it was that I was told I could make similar to what I was making as a software engineer, and it would require me to get outside of my comfort zone, and to learn new skills.

After going through training though, and going door-t0-door with the owners, I decided that to get enough interest you truly do have to "sell it." We had one lady who said she had it at her previous house, and it was the best decision she ever made, but for the most of the people we've met, they aren't interested unless you lead them into being interested. We were taught in training how to do this, but it felt very disingenuous, and too much like manipulation to me. I'm not sure that I could make enough sales to provide for my family by speaking plainly to people.

E-Commerce

I'm concerned that this may just be click-bait, but I've listened to multiple entrepreneurship podcasts, and I've found the theme of e-commerce coming up multiple times, and in different ways.

One person said he does "high ticket" e-commerce, selling very expensive items (like saunas), and having them shipped from a manufacturer or distributor, so that he never has to keep inventory in stock.

Another said that he made a good living selling custom dog collars on Etsy. He started making them himself with a cheap sewing machine, and fabric you can find at any store. Now, he prints his own fabric as needed. He also uses a laser engraver to engrave the buckles with the dog's name.

Lastly, I've listened to a guy who buys snacks that can only be found at one (very popular) gas station chain in Texas, and sells them online at a markup so that people can access them nationwide.

For all of these, the key is marketing, and getting the product in front of people.

Hotshot Driving

For a while I've been curious about folks who pull long flatbeds behind a 1-ton pickup. Most of them have a sign on the door that sounds like a small, family owned business. I've wondered where they find the jobs, and how long they're gone.

Just yesterday I was talking with a guy who was also in training for D2D solar sales (and who had many of the same concerns that I had), and he gave me a word for it. He said it's called "hotshot driving", and that he was also looking into it. He also pointed me to an app where you can find jobs.

I don't have a large truck, or trailer, but my father-in-law does have a decent sized truck, and a flatbed. I've considered seeing if I can use it to test the waters and see how profitable it might be, and how much time away from home it would require.

Conclusion

I've got many ideas, but have a hard time figuring out what could make sense. Just last night, I looked over my 16 Personalities assessment that I took a few years ago, and realized that a lot of the things above, that I was already thinking line up with ISTPs. I also realized why I loved working for one company, and felt like I was growing there, and have really struggled at the other.

As I write this, I'm about to go speak with my father-in-law who has been a business owner about the personality assessment, and see if he can offer insight. I will try to update as things progress, but for others in similar situations: Hang in there. Push forward. And consider taking a look at 16 Personalities. You might be surprised, like I was.