Over 50 and trying to stay relevant...the struggle continues

Hi Team!!

I was trying to think of the most topical topic for me to discuss and this popped into my head because I don’t see it covered too often. How do you stay relevant? What topics are you studying to keep companies interested in you? Do you struggle with today’s technologies if you trained in the 80s?

Most technology coverage deals with technology and not necessarily people. I’ve entered my 50s and while I’ve done okay in IT to date, I noticed how hard it’s become to stay up-to-date and relevant as I got older. That’s why I’m curious if there are others out there like me.


Same boat here. I have noticed that staying with the same company for a long time has also hurt me. Finally, being with a small company has it’s drawbacks but also it’s pluses. I get to play with any new tech I want to, but at the same time, I don’t get to learn from others while at work since I am the entire IT department. My previous employer was much larger and I could learn from the Security guys, or the Web guys or the Networking guys. Now I pretty much just have to skim over the stuff I need to know, just enough to get it working and outsource what I can’t figure out.


I started my own company at 48 and I highly recommend it. It’s such a joy not to have to look for work any more. But I know I’m incredibly lucky!

As for continued learning, it’s remarkable how well being asked tough tech questions on live radio can sharpen the mind.

I keep waiting for the day when those young whippersnappers say, “what do you know about tech, grandpa?”


Agree that moving out of the Enterprise space and into a smaller company actually seems to open up more opportunities both in learning tech AND in learning about the company and more importantly its people. I also find that you have to continue to invest in yourself with training. Luckily there are solid options there online.

I worked many years in 5000+ employee companies but my “successes” have come in companies of less than 300.

I definitely am inspired by the voices on Twit…and I admire what and how Leo has built it out. My wife has always wanted to start her own company but coming up with “that idea” or “what our passions are” always seems to be the stumbling block.

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I’m getting close to “exiting” my 50s… ;-(


@calgaryguru do you still find excitement in tech? Or do you find the wallet comes out less often?

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I am working for a company now, but I spent 20 years with my own consultancy.

Staying relevant is investing in education in areas you have an interest. My background is programming, so learning new languages was my jam. In the process, I picked up lots of other skills in different OSs.

My current side projects are split between Raspberry PI projects and 3D Printing. Both require a lot of tinkering, and research.

But, I’d say the key to staying relevant is to find a problem that affects you, and go about solving it. Especially in an area stretching your comfort zone. You may or may not be successful solving the problem, but you will learn a lot along the way. Enjoy!


I’m 58. I honestly believe watching most of the TWiT podcasts has really helped. Plus…it’s just plain fun.


I started in telecommunications in 2000 at age 30ish… (Think Blackberry but adjacent) The smart phone basically killed land lines and feature phones and the door was shown in 2014. Despite my focus in system and network security, no one is interested in what they view as a pigeon-holed over the hill software developer who doesn’t have a buzz-word filled resume.

It doesn’t matter how skilled you are if the 25 year old thinks you’re too old to be relevant… and who wants to be interviewed by someone young enough to be your grandkid and told you’re not relevant because you don’t have “gee-whiz-mo 4000” on your resume with 20 years of experience (even though it just came out last year.) :disappointed:

I’ve basically given up sending out my resume any more… I’ve spent a lot of the last years mentoring a couple of new grads… Gives me plenty of time to keep abreast of technology which my TWiT consumption is part of.


Well, I use a 2008 Mac Pro and a mid-2010 MacBook Pro… I guess I don’t upgrade all that often. I might replace the laptop if there’s a 16” with a great keyboard like my current one. We’ll see, I guess. One was capped at El Capitan and the other at High Sierra. Oh, I also still use my original iPad Air 1. It capped out at iOS 12.

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58? Just turned that last month.


I’m 30 and all I want to do is work independently. I work for the DoD and I always get comments about “how lucky I am to be in the system” and comments about job security and good benefits. And yeah, all thats true but the way things work here is something that really bothers me. No autonomy, everything is fragmented and responsibilities are all over the place…and usually really minimal.

I can’t tell you how much I want to be in control of the work I do. My biggest skill is organization and planning and as an office drone in a cubical I get none of that.


I thought the chat room took care of the hard questions :nerd_face:


Everything I know about tech I learned from TWIT :grin:

Now Seriously, I will be 50 next year and although I no longer work in the IT field,
I still try to not fall behind, as much as possible. But I agree with the other comments on here about it not being easy. On top of watching TWIT a lot, I read Mac World, and other tech sites to try and stay current. Or just use the old Google :slight_smile:

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@godfrey I believe that research supports your desire to have control over the work you do. I think that’s one of the keys to work satisfaction. In my experience the more responsibility/ownership that you have tends to bring a higher level of engagement. We all want to be seen as experts in our field (or at least valued) and not being able to contribute in a transparent, direct and honest manner is so much more debilitating than an open environment that fosters communication.


I read somewhere that the highest work satisfaction is among orchestra conductors and traffic cops because they’re in control!

Sounds like a Malcolm Gladwell factoid now that I say it out loud!!


I think that’s why people are happier in start-ups or smaller companies b/c they tend to be the Swiss army knife of workers. Always doing a little bit of everything. Even with the inherent risks associated with start-ups financially, etc. there just appears to be more engagement.

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I agree completely. The best leaders I ever worked for created an effective and efficient working environment from their ability to make us care about the work. Being prideful and having ownership of your work and your team does wonders.

That said I’m still in a state of “how do I do that?”. I’m considering leaving my job after fall semester. I have some passive income so I think financially it’ll be alright (a little tight but nobody will starve). Using the time I’m not working on classes to build my personal portfolio and figure out how to begin generating my own income. It’s a ballsy step but one I think I can make.

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Sorry for taking over the 50+ thread with my 30ish whipper snapper ramblings. Just hoping for some good insight from the older folks in the field.

I am now retired but entered network technology and support 20 yrs ago. Faced a lot of headwinds due to age and lack of direct experience. It turned out to be worth it. Trying to stay knowledgable now just for fun.