In my time as a software engineer I have learned a lot from each job that I’ve taken. In this article I’d like to share with you some experiences throughout my career and what they have taught me, both the good things about each job and the challenges that I experienced, or as I like to call it, the lessons I learned along the way. Specifically… 15 lessons. Counting backward for dramatic purposes.

Lesson 15 – Don’t kill yourself, work hard enough to grow & not resent.

The first job that I had out of college was at an advertising agency. The good thing about this job is that while I was there, I saw some of the most captivating presenters in the world. It was as if everyone at that job was Don from Mad Men. But the challenging thing about this job was that it was basically a sweatshop. I once got a nosebleed from working over 70 hours, and some of my coworkers were putting in over 100 hours a week. Eff that.

So, one of the first lessons I learned was that overworking myself like that wasn’t good for me, and I needed a job that wouldn’t put me through that.

After that job, I was inspired by a friend of mine to go into technology, so I enrolled in a master’s program at DePaul University. In order to pay for the program, I got a part-time job at the help desk at that same university as a client support specialist. The good thing about this job is that I learned how much fun and challenging (in a good way) a job can really be. I did a lot but wasn’t working until midnight constantly. Felt good leaving work with daylight remaining and wasn’t resenting the work. Then again it was part time but still, fulltimers there left early too.

Lesson 14 – Always be friendly.

I had a good relationship with my boss at DePaul, but there was a coworker who was friendlier with him and ultimately, when one full-time position opened up there, we both applied but he got it. He was good at his job too, but his extra friendliness with the boss gave him the edge he needed. I know it did. I’m not saying to kiss up but I could’ve been more present socially (like at events) and been more in his circle. 

Lesson 13 – Don’t let being passed over hold you back from making the moves you need to make. 

There was another opportunity for a full time position that opened up months later and I wanted that too, but this time no one in-house got it but some outside contractor. To make it worse, this contractor was always asking me to help him fix stuff he couldn’t solve on his own, and yet he was getting paid three or four times what I was. So I thought to myself that I should try to become a contractor, and I put my resume out there, and it worked like a charm. Within days I had recruiters all over me. So it actually worked out pretty well for me to make my next move. I didn’t just huff and puff about not being promoted to the role that an inexperienced contractor got.  I made my moves.

Lesson 12 – Lack of challenge can lead to boredom, but don’t let that slow you down.

My next job was a job as a help desk technician at Andersen Consulting, which is actually where my friend worked whose job had really impressed me. The good thing about this job was that my boss was awesome. And in fact she did her job so well that the computers didn’t really have a lot of issues for me to solve, so it wasn’t very challenging as a help desk technician, but because of that I was able to move into programming which I loved. Which is what motivated my move from help desk to programming. I didn’t just stay doing boring work. Again, I made moves.

Lesson 11 – There will be haters. Get used to it.

Another lesson that I learned is that there will sometimes be employees who do not like you and do not want to help you succeed. It hasn’t happened to me too often, it was really just this one person at this job, and although she did not actively try to sabotage me, she was unwilling to help me out with questions I had or anything like that, and she only acted like that behind the boss’s back so no one else would know. So, what I took from that is that you can’t always depend on the people who are supposed to train you and help you out. I learned not to take it personally but it took a while. It took practice not to care about those that hate you. I still work on not caring even today. But it helps that most of my projects were great at Andersen. I only left there years later because I had to start traveling as a programmer which I didn’t want. But I left on good terms with some great memories. And tougher skin.

Lesson 10 – Save. Save some more.

The next company that I worked for was Inforte. The good thing about this company is that it was a very familiar culture. And it should have been, because the people who started the company actually worked at Andersen Consulting too before they spun off their own consulting agency. Their business model was pretty much the same. They damn near copied and pasted Andersen’s biz model but they didn’t last.

As such, what I learned from them is that you need to save money, whether you’re an individual or a company. I started working at Inforte during the dot-com bomb when the economy was taking a turn for the worse and there were a lot of layoffs in the technology field all over the country. The Inforte company had saved up enough money to hang around for a long while, but eventually they ran out and little by little every department was hit with layoffs. And about six months after I left, I found out the company had shut down.

Lesson 9 –  It’s not me, it’s you. If everyone’s always working long hours, it’s usually due to poor management.

The next company that I worked for was Risetime Consulting. The good thing about this job was that it was the first time that I was working in a really small team and building applications from scratch. I was there for the design phase up until deployment, and I was able to become really close with the guys I worked with there, and we stayed in touch for a while even after I left.

It was a sweatshop too though. Then one day we came into work and our manager wasn’t there and the CEO invited us into some dark room to talk. He told us that we’d been missing a lot of deadlines. I thought it was the end for us.  But then said he knew it wasn’t our fault because we’d been putting in the work and working long hours, and so he made our team lead developer our new manager. He said something I’ll never forget. If you’re constantly working a lot of hours, it’s usually due to poor management. This was something I’d never really considered before. And suddenly we weren’t missing deadlines anymore and we weren’t working long hours. So keep that in mind: if you’re in a situation where you’re constantly working crazy hours and are always pressed for time on deadlines, it’s because of bad management, and if no one seems to want to change that, then it’s probably time to move on.

Lesson 8 – Some companies can absolutely be loyal to you. 

I left Risetime because I was hired during a recession, and took a big pay cut. They knew I had no choice. So when the economy got better and an opportunity came up to get paid at the level I felt was more appropriate, I took it. And this job was with Andersen Consulting again, now called Accenture. Boom! Back home, baby! And that’s why you should always try to leave on the best terms that you can, because sometimes second relationships happen. I loved going back to work here and this time the role they got for me did not involve travelling, which was perfect. I felt there was a sense of mutual loyalty going back.

I remained for several more years but eventually moved to California. They didn’t have any major projects there so we sadly parted ways. Several of my colleagues there are my Facebook friends even today.

Lesson 7 – Don’t get comfortable. Stay hungry.

The next technical job I got in California was with the Tribune company, which owned the LA Times. The good thing about this company was the work environment. I really bonded with my colleagues at this job, we would work out together and everything, and it was so fun going to work that it didn’t even feel like work, which is how it should be. But as a result, the lesson that I learned is that you don’t want to get so comfortable at a certain job that you lose touch with other opportunities that may be out there for you. That’s what happened and I could’ve advanced sooner rather than staying at that job for so long.  

Lesson 6 – Stay skilled, on the edge, where you need to be. 

Also, I was in such a comfort zone at Tribune and I was so focused on just being good at that particular job that I didn’t pay attention to skill sets that were evolving outside of the company. And then when it was time to move on, I struggled to play catch up.  So, another lesson is keep your skills sharp. 

Lesson 5 – Some companies WILL NOT be loyal to you. UH DUH.

At one point I came up with a business idea that would bring in more revenue for one of this company’s departments, and I brought it up to management and wrote up a business proposal and execs really liked it. I was putting a lot of energy into it and brought on a consultant (pro bono) to help push the idea forward. This guy was so good and in the past had actually created an online apartment rental company and sold it to Tribune. But then one day this one top exec who had initially supported the effort suddenly lost interest and had some secretary come tell us to drop everything. That was a lack of loyalty and respect because he didn’t even bother to have a conversation about it or address us face to face.

Lesson 4 – Winter can come anytime. Don’t be left out in the cold. Be prepared.

The economy turned bad again and we knew winter was coming because all a sudden, top executive after top executive was turning their resignation in to “spend more time with their family”. That’s how top dogs go. Via announcements. And then, winter was here. We experienced a corporate Red Wedding. No one was safe. Tribune laid off over 200 people and even though our team only had three or four developers, we still got hit, and I got laid off. Always be prepared for this. I fortunately had started training on my own on a new project.

That project was my next job.  It was a company that I started up, and I called it Prestige Artists. I applied new coding skills I was learning after Tribune layoffs to create the site. And this was a great endeavor and it’s something that I recommend to anyone who’s in between jobs. Take the opportunity to create your own company/side hustle because that way it doesn’t look like you have a huge gap on your resume where you’re not doing anything. So the lesson I took from this experience is just how valuable it can be to make your own company while you’re otherwise unemployed. I was able to learn a lot of skills that I then applied in building out my website which was a site for booking artists for corporate engagement. And having that on my resume made it much easier to get my next job. No one held it against me that it was a company I started. But they do when it’s just an empty gap for a long time.

Lesson 3 – Stay focused. There will be brownnosers that succeed.

My next job was at Logix credit union. The good thing at this job was that I learned how great a company can truly be at creating a positive company culture. They went above and beyond to ensure that people were happy and had a good work-life balance. No one I knew of there was ever working overtime or anything. The lesson that I learned from this company is that in your life you will encounter people who are brownnosers. There was one person at this company who did such intense brownnosing that it hurt my stomach just to watch it, that’s how embarrassing it was. And the sad thing was, it was working! The boss, she loved it. And that was really annoying to see, but what I learned is that you can’t let it get to you. 

Lesson 2 – Stay current. Stay fresh. Be in the know.
The next lesson that I learned from this job is that it’s not so good to be around legacy technologies that you don’t learn from. Remember when I said that when I was at Tribune, I was in a bubble and didn’t keep my skills sharp? Well, this time, I had learned from that experience, and so even though this job mainly had me working with legacy technologies, I kept my skills sharp learning new technologies on the side and even got into teaching tech.

Lesson 1 – Never assume they’re happy if nothing is said. Confirm it.

And that brings us to the present, where I’m now an independent contractor writing and teaching courses for various companies. The first site I started doing that for was Lynda.com/LinkedIn Learning. And the good thing about this job is that I’ve learned how awesome it is to have a lot of students and a public audience that truly enjoys and appreciates your work. The lesson I’ve learned from this job is that no matter how good your work is, if you’re producing content for different people, you always want to make sure that what they got is what they were expecting. And you shouldn’t make assumptions just because they didn’t complain. So, even if you’ve made a bunch of former managers really happy with your work, you still want to make sure to ask questions whenever you get a new contract to make sure you’re giving them what they want.

So that’s what I’ve learned throughout my career as a software engineer. These lessons I learned are the things you’re going to want to know how to deal with. And the truth is that it’s not always easy when you come across it, it takes practice, and sometimes it can even take years to implement some of them. But hopefully this article has helped to prepare you for it.