Worst Job & Best Job

I’ve worked at several jobs in a few different industries. I started working in 1994 (if you don’t count the three summers that I worked at a Scout Camp, mostly on the kitchen staff). It wasn’t until 2011 that I started working in my current career field of Information Technology, which I’ve found suits me very well.

Regardless, I feel that you can learn something from any job you work, no matter how good it bad.

I worked for a year at one job that I will never do again (a job I took just to provide for my family, not because I was interested in that line of work). I was a correctional guard working the night shift at a privately run prison.

  • To start with, I was uneasy about the work. I’d previously worked in retail sales and as an educational assistant (computer lab monitor, tutor/TA)…all jobs that matched my core values of being warm, helpful and friendly with people. As a correctional guard, I had to basically put my true self aside and put on a persona (though still my normal fair-minded, even-tempered self, I couldn’t be warm, friendly or helpful).
  • It took me six weeks to adjust to being nocturnal, and almost as long to adjust to work which was, on its surface, entirely dull and unengaging.
  • I had to follow (understandably) rigid protocols and schedule, with little or no room for variation.

To keep my mind engaged, even in the fullest hours, I had to be creative, such as making minor variations in the security checks.
For example, while conducting an inspection of the perimeter fences (done at least once per shift): ‘I haven’t looked from this angle before’, ‘Let’s walk a serpentine path today’, or ‘If I were a member of the A-Team, what security points would I see as the weakest?’).

I didn’t feel like that employer was invested in me as an employee. They were supposed to enroll me in State-mandated training by my 60th day of employment… But they didn’t enroll me to start the training until a year after I started working there.
By that time, I was certain that Corrections was not the right career field for me, and I was already planning to move to be closer to family. That move would eventually lead to my best job (at least, the best so far).

My favorite job to-date was working on tech support at a university computer help desk.

  • I got to use all my best self: being warm, friendly, helpful, and a technology nerd!
  • The work was mentally-engaging, and personally rewarding from the satisfaction of knowing that is helped people solve their tech problems.
  • I was involved with hiring and training new tech support representatives (TSRs). I got a lot of fulfillment watching them learn and grow in their customer service and technology skills, and I felt pride whenever any of these “baby birds left the next” (most were college students, who would leave when they graduated; some would move up to other Information Technology specializations even before they earned their degree).
  • With any slow periods, I could focus on developing my tech knowledge, mentoring the TSRs, and writing technology help articles (or rewriting existing ones to be more customer-friendly).

Sometimes, the work could be so fast-placed that it could be a bit overwhelming. Sometimes it would make me mentally-exhausted in as little as half-an-hour:

  • I was part of a great team of people (the Help Desk and the next tier support team just down the hall), and this team-atmosphere bolstered me.
  • My manager there was the best work mentor I’ve every had, and he was great at recognizing and addressing his employees’ needs. It’s so refreshing when management recognizes that in order to “put customers first”, that their employees are THEIR customers.


  1. A person should do work which:
  • Interests them
  • Makes good use of their skills, talents, and education
  • Gives them a path to grow and advance
  • Let’s them be their best self
  1. For people to want to work for an organization, the employees should be:
  • Treated well, valued by their leadership
  • Properly trained and equipped
  • Given authority, autonomy & accountability for their area of work

Very interesting. Many years ago I interviewed for a job as a social worker in a prison setting. As an MSW in 1973, I was in a small minority of men in the field of social work. So when I went for the interview I was offered the job almost immediately. Of course the inmates were men. I told the Director of Social Services that before I made a decision I wanted an opportunity to see what it was like “on the inside”. She asked me to come back in a week as she did not have time to give me a tour on that day. Long story short, I came back and walked into the prison. As soon as the steel bars slammed shut behind me, I knew instantly that I just could not work in that setting. We got back to her office and then she asked, “when can you start?”. When I told her that I decided against taking the job she became rather angry. Aside from the physical setting, I just knew that I would be so easily conned by the inmates and also that I probably would be anxious most of the time. That would have been the worst possible job for me.

For most of my 45+ years of work as a social worker I worked with persons in the community having serious and persistent mental illness. It took me a while to appreciate how the “clients“ and I were really not that very different. It was all a matter of degree. So some of those folks had serious depression, anxiety, delusions, hallucinations, etc. Well I had / have depression, anxiety, OCD and ADHD. It took a couple of years for me to realize that “there but for the grace of God walk I”. Once I understood that my work became more rewarding and I was better at it.

Had I done things differently, I would have worked in a university setting, as a research librarian. As I have said here a number of times before, I love doing research . . . It’s fun . . . it’s like a scavenger hunt!

So we have some things in common (aside from being :brain::brain:).

Take care my friend,

PS: Please remind me of your first name . . . (and if I forget it . . . again . . . I will just have to go on another scavenger hunt! :joy:)!


This was something I told myself many times while working at the correctional facility. (It was a prison for people with shorter time left on their terms, getting ready to parole out. While some inmates were repeat offenders, others reminded me of people I knew on the outside.)

Here in the forum, I go by my initials: ‘JD’.

(On public forums, I prefer some anonymity. On social media platforms, I’ll use my full name, but only connect with friends and family. This is because I tend to be a very private person by nature, plus my Information Security training from work makes me even more cautious about my online presence.)

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Well “JD” . . .

I understand perfectly!

And appreciate all that you have shared here . . . as I have since “meeting you” (So to speak).



Life lesson (from my second-worst job experience):

A bad boss can make a job feel like being trapped in a prison. You can be in the right job and the right organization, but working for someone who seems more interested in them looking good to higher-ups than treating their employees with empathy & respect is a bad job to be in. It is very demoralizing to the employees.


I’m not sure I really can just say “best” or “worst” with any of my jobs. I’ve found things I like and don’t like about all of them. Maybe I can focus on some of those…

I did really enjoy my college summer job working at a small family-owned amusement park at the beach. The hours were really long, but you got to deal with so many people who were on vacation and having fun. Even the jerks provided great stories. And the job came with room and board (dorm style), but we could look out the window at the beach and water.

In terms of career-oriented jobs, I’ve worked at a couple small startups and seemed to like those a lot. They were both focused on hiring cooperative people and were small enough that we had to work together to achieve our goals.

When I worked at a NASA contractor, I liked the work and a lot of the people I worked with. But the environment wasn’t the best match for me. There was too much bureaucracy for me.

I spent time at a large company that was well-known for how well they treated their employees. The perks were great. But I encountered far too many people who were trying to make a name for themselves, often at the expense of people around them. As JD said:

I had one director who refused to give me credit for my accomplishments. When the public announcement of their promotion to VP came out, three of the five things listed on it were my projects for which their contribution was minimal. But, in fairness, I will also say that I met tons of really great people there as well.

But I am definitely appreciating the fact that, after about 6 months, I’m really enjoying where I am now.


Good for you . . .


As a side gig during college and for much too long atfer that, I worked night shifts in a residence for formerly homeless people. Not being overly social, it sounded great because I didn’t have to interact much with the residents (mostly asleep at the time, or too drunk to interact) or do anything, really. I could watch TV, draw, write, read - and before long. I was bored right out of my mind. For a week every month, I basically turned into a vegetable. The sleep deprivation didn’t help much either.

My next job was better because I got to do stuff, but I wasn’t allowed to do anything creative. The company had a narrow set of services and profitability meant to never put more work in than absolutely necessary. It was okay for a couple of months, the people were nice and I made enough money to last the rest of that year, but I don’t think I could have done that indefinitely.

Another college job was moving furniture within the college. That was cool. At least the work itself was. The boss was possibly the lousiest excuse for an authority figure I ever met. One morning, she fired a guy just for showing up late (there had been a traffic jam because of fog), and then she fired me for speaking up against that. Well, not exactly “fire”. She just never called me in again for another shift.

What did I learn from those jobs?

  • I can’t deal with small-mindedness. Neither in people nor in how my tasks are set up. I need to either be able to spread my brain or be active some other way (as I said, the moving furniture bit was great).
  • I also can’t deal with hierarchies and people who take them too seriously. If respect doesn’t go both ways, it’s wasted.
  • Third, I learned that it’s not so much about what I do but about how I get to engage.

I now work in a small company with great colleagues and lots of different things to do and some liberty choosing tasks. Also, it’s part-time. So much for the best job.