Some of My Stupid Career Mistakes

The best programmers are the ones who’ve made all the mistakes.

Rob Hamilton

The articles I’ve read about career mistakes typically feature generic-sounding items such as “not asking for what you want” and “choosing money over happiness”. In this post, I’ll be focusing on very specific stupid things I did and their consequences. I’m writing this article so that you can see the folly in my decisions and actions and hopefully avoid these types of mistakes yourself.

Not Taking the Job in Italy

In the late 1990s I was in my mid-20s and had passed the CPA exam and finished studying marketing in grad school. I was working as a consultant doing entry-level database analyst work. I’d studied Italian as an elective in grad school and had spent a few months in Italy, so my Italian language skills were somewhat decent. While working on a client site I received an email from a recruiter about a possible job in Italy. I called him on the phone and he told me there was an American company helping a firm in Rome perform some renovations to some ancient Italian sculptures, statues, and buildings. They needed someone who could speak Italian who also had knowledge of US accounting principles to help record and quantify the renovation efforts.

I’m sure a few years previously I would have been very interested. But I’d recently started studying and working with databases and I was excited about becoming a better programmer. I told the recruiter I didn’t want to “go back to accounting” and that I was “doing computers now” and therefore wasn’t interested. It wasn’t until years later when I reflected on the incident that I realized how short-sighted my decision was. “Computers” weren’t going anywhere and would be just where I left them when I returned. Can you imagine what fascinating adventures in Italy I might have had if I had said yes? I sure can, and it makes me sad to think about it.

Believing that 401(k) was a Scam

In the early 2000s I was working for an internet startup company in the San Francisco Bay Area. That company, as part of its benefits, offered a 401(k) plan where they matched employee contributions. At the time, I’d heard a few unconfirmed stories which cast some 401(k) plans in a negative light. Without doing any further research, I decided that 401k plans were a “scam perpetrated by the US government” for some reasons I didn’t understand. As a result, I didn’t contribute any money to that plan and forfeited any company match I would have received. Hmmm. I wonder how much money that 401(k) plan would be worth today?

Acting Argumentatively During “Creating an Inclusive Environment” Training Class

In the mid-2000s I was working for a company that offered world-class employee training. I was taking a class called “Creating an Inclusive Environment”. The truth is, I can’t remember exactly what I said but I do vaguely remember feeling annoyed and somewhat argumentative. I think I raised my hand a few times and said something obnoxious to the well-meaning presenters. A director took me aside and said that my remarks were unhelpful. I have to admit she was right. I came home from work that evening and explained the situation to my wife. She said as a general rule I should feel free to say what I like in situations like that, but that I should “check in with my feelings” beforehand to make sure I’m not speaking from anger. If I am feeling angry, I should understand why before opening my mouth. The company forced me to repeat the class, which I didn’t mind because I enjoy training classes and I needed to practice the lesson my wife taught me. I’ve used that advice she gave me several times since then.

Yelling At One of My Employees

In the late 2000s, I was working for a firm where I had several direct reports, some of whom were in another state. Occasionally, I would check in with their internal customers to make sure they were satisfied with the work product. For the most part, everything was going smoothly with these employees. One day, I began hearing negative reports about one employee saying he was taking too long on a project. Some members of leadership told me they thought he was being overpaid for his job. I called him up and inquired about the situation. There was some sort of database program he’d been requested to create to provide data to one of his customers. He said it was too difficult for him and that there were things he didn’t understand about how to complete the project.

Rather than being sympathetic and trying to help him through some difficult concepts, I yelled at him and told him to try harder and to get better quickly to justify his high salary. I know I made him feel bad that day and I’ll always regret it. I’m pretty sure I apologized to him later but I wish I were able to somehow magically erase that memory from his mind, but not from mine. I deserve to feel the shame of my mistreatment of him. I hope it motivates me to treat other people better.

Several years later, as if repaying some karmic debt, the exact same situation happened to me in reverse. I had a brilliant boss who was a much better Python programmer than I was. He gave me a project which had me completely stumped. I spent at least three weeks pouring over his code, tearing my hair out, and making no progress. When I went to him for help the first time, he helped a little but was too busy to continue. When I went to him for help the second time, he yelled at me, saying that I was in an advanced position and that there were people in lower positions than mine who were able to figure things out by themselves. He took the project away from me and completed it himself after a few iterations. (Incidentally, a few years later, I successfully completed three very similar projects which made me feel better about this incident.)

What I should have done with my employee was fly to his location and spend a week with him pushing past all the obstacles he had and making the situation better for everyone. That’s what a good manager would have done but it’s not what I did and it wasn’t what my boss did. None of the people in these two stories still work at those companies, but I’m sure the painful memories persist.

Acting Cocky During an Interview

There’s a thoughtful and funny TV show called “Silicon Valley” which parodies a group of young people who create an internet startup company. I had watched a scene in that show where the actor Charlie Saxton’s character explained during an interview how he “crushed it” during certain recent periods at various jobs. It’s a very funny scene available on YouTube.

I must’ve been in a silly mood during the interview for the job with the Python incident above. I told my soon-to-be boss how much I would “crush” the job if I were selected. He actually gave me a coaching during the interview about keeping a more serious attitude and being cognizant that the challenges I could face in the job might be more tricky to solve than I was giving them credit for. He turned out to be right. There was at least one project I certainly wasn’t able to “crush”. Well, don’t I feel silly now.

Ignoring Interview Red Flags

I guess I had to learn the hard way. The purpose of looking for red flags in an interview is to use them to weed out an opportunity that’s not right. Ignoring one red flag is one thing, ignoring multiple is inexcusable, and that’s exactly what I did.

I was working for a company which was about to go out of business when I realized I should start looking for a new job. A work colleague at another company set up an interview for me at that company. I was excited by the prospect of working with my friend again and finding a place to land before I got laid off. I thought I might do well at this new company and decided I wanted the job before I even had the interview. This is equivalent to going to the grocery store when you’re hungry. It’s a bad idea.

Let’s review the interview:

• When I first met the interviewer, who was to become my boss, we immediately didn’t get along and our back-and-forth conversation was awkward and uncomfortable. Red Flag #1.
• When I inquired about the company’s annual revenue, he refused to even give me a ballpark number. Red Flag #2.
• When I asked about the specific duties of the position, he used incorrect language and revealed a complete lack of understanding of the subject matter. Red Flag #3.
• The industry I work in requires significant IT infrastructure. I discovered the company’s infrastructure was practically nonexistent. Red Flag #4

After the interview was over, I emailed the interviewer explaining that I was not interested, and I thought that was it. A few days later, he emailed me back, asking me to reconsider and saying it would be a great opportunity for me. I was both flattered by him asking me to reconsider and excited about getting a significant pay increase from what I was previously making. Both of these were examples of me allowing my ego to be manipulated – big mistake. Nothing at all had changed about the company from a few days earlier but I allowed myself to change my decision. Why would I do that? Was I not of sound mind when I initially turned him down? Did I not mean what I said? Am I some kind of milquetoast pushover?

With no new information, my answer should have remained the same. Guess what happened. Everything I suspected was wrong with the job came to pass as I anticipated. I never got along with my boss. There was never enough technical support. I did some good work for that company and learned some new skills, but I ended up quitting on not very good terms. This all happened because of my poor judgement. I correctly identified a rotten apple as rotten and then I bit right into it! Next time, I’ll take red flags more seriously and make a better decision. I deserved my bad consequences. For someone with my experience, there is no excuse for my poor decision and I deserve all the torment I experienced because I visited it upon myself. What kind of “career coach” doesn’t heed his own advice? Fail. There is no better teacher than consequences.

Where Did I Go Wrong?

In every case above, I went wrong because I acted impulsively in one way or another. Rather than taking extra time to thoroughly contemplate each situation and come to a measured decision, I took the lazy road and trusted my initial emotional reactions. I do trust my own good judgement but not necessarily my first impulses. I need to be honest with myself when distinguishing the two.