August 17, 2015 was the start of me getting W2's for computer stuff. And it's been an eventful ride in the 5 years since.

There've been 5 different jobs and probably 3x as many interviews in that time. More if you count non-W2 side gigs, which even I can't fully remember.

For employers, in order of appearance —

  • New York Central Mutual
  • Lockheed Martin
  • Aspect Security
  • EY
  • WarnerMedia (HBO Max)

This post contains only my personal views, and does not reflect any of those organizations' views. There's a half-hearted disclaimer for you.

What lessons can be distilled from all this work?

Settling in might take 10 weeks

This ignores NYCM because I didn't stay there 10 weeks. That place was an aberration in my career path, but it was enlightening.

All these other jobs, looking back, it took me 10 weeks to feel like I had a good handle on everything going on.

For that feeling of being a n00b — who isn't fully contributing — to go away. For any overwhelming sensation to go away. For the "honeymoon phase" to wear off, if it has set in.

Others have said it takes 90 days or 12 weeks, so your mileage may vary. In my opinion it shouldn't take quite that long if you are sharp.

Take it easy on yourself during this time. I should've taken the advice here for my recent-ish start at WarnerMedia. That same feeling of overwhelm set in as at any other place.

It's super unlikely you'll be fired in your first 10 weeks — 90 days?? — as long as you don't set anybody on fire or do some other egregious thing.

You'll also be pretty comfortable with who key players are and how the business works on the other side of this period.

Don't chase prestige

Half of my time at Lockheed Martin, I was miserable there. But they're a well-regarded employer in the area where I lived then.

So the average person would hear that was my employer and go "Wow!"

We all like our egos stroked. At first, the wow's made me feel good, yes. Then once I became jaded on the place, they prompted rolls of my mind's eye.

The biggest personal triumph for me on that job list was going from LM to Aspect Security. It was a fairly different job, brought on by skills and connections I'd personally fostered. That was a very special place with great people, many of whom I still keep in touch with.

You get the picture.

Except, average people no longer said "Wow!" about my employer. They'd say "What's that?"

My own parents were very skeptical until after several months it became clear I was happy and this was stable work.

This is all boiling down to — there are some very special places to work that most people have never heard of. I won't get political, but do regard small businesses as the heart of America.

Don't make career decisions based off some "brand", illusion, or other people's perceptions of where you're associated with.

Ambiguity != negativity

Human beings tend to interpret ambiguity as negativity. This is suggested by numerous studies, and my own experience.

There's a reason I always start emails with "Hi Firstname" or "Hey Firstname", often throw in one emoticon, and end with "Best," or "Thanks!" or "Thanks!!"

It's because, especially early in my career, I would read people's emails that started with Randy-comma-blah-blah-blah as if they were scolding me.

If your emails or Slacks or whatever read as ambiguous, a major portion of people will read them as negative. I swear.

So be liberal with thumbs-ups and smileys in Slack or Teams. Write your emails with care. Actually, when possible, go talk to someone in-person or on video.

Don't let people doubt whether you come in peace. Security engineers especially.

Ignore or subvert 'speed limits' as possible

Some people will read this out there like, "5 years is nothing you twerp — I've been a 'systems administrator' for 25 years!" then stroke their gray beard.

The whole pay-your-dues culture in tech is harmful, in my opinion. This should be a meritocracy. "Years of experience" is a very poor indicator of how good you are at anything.

Same might be said for degrees, certifications, etc. I think less of people that list their technical certifications or degrees in their email signatures.

That is something we've covered more directly here in a previous post when engineers were looking down on my self-taught sister.

I just care about what you can do. Cultures built around that are better.

Smile and talk

This may read as a little contrary to my last point, though not if you're wise or a quick learner.

A lot of tech people hone their engineering skills only. This feeds a stereotype of people working in IT as being socially defective.

Like it or not, humans are social creatures. We aren't robots. It's humans that decide when you get promoted, what tasks you work, whether certain expenses get approved, and more.

Maybe in the future we'll work in DAOs (decentralied autonomous organizations) where Ethereum system or whatever decides on that stuff. But we don't right now.

What's the easiest "hack" for your social skills? Start smiling when you converse with people. And that includes on phone calls — audio-only — as I've written about in my guide to phone calls.

After you've mastered smiling? It's time to master what might labeled "small talk" or "chit chat."

Doesn't matter if you think small talk is pointless, if you have such a large brain that you only talk about existential nihilism and the Western canon. In fact, those people are in dire need of chit chat.

"Ah, Randy, so you mean social engineering."

No, I don't. Small talk and chit chat are pleasurable whereas social engineering is a deliberate effort to manipulate others to do your bidding.

Which brings us to the first step in doing these things — don't be a psychopath. Stop spending so much time on Twitter, Reddit, and/or 4chan.

Step two — find pleasure in small talk and chit chat.

Step three — indulge in them, patting yourself on the back for becoming better at socialization.

And that sets off a cycle. The more you talk with other people, forcing yourself to do it or at least trying, putting in some effort, then the better you get at it.

It's like a "muscle" of your brain. Small talk gets stronger the more you do it. Soon you can talk on and on about nothing, with much joy. Especially with fellow tech people because you can just talk about tech topics.

Reading between the lines, you'll find a great reason for not being a remote worker. Offices can be better "gyms" for your social skills.

But volunteering or encouraging voice calls about appropriate work topics can work too, as part of your remote worker skillset.

Closing thoughts

Fellow tech workers, I wish you the best. Hope these nuggets of knowledge might help you.

There's room for a lot more people to benefit from our industry — abundance mindsets are healthy.

This line of work has been very good to me. Thanks for the good times so far.