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On Career Change

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Hi Everyone, I’m Leo Notenboom for I got a very interesting question this week, and I want to read it to you. It’s actually a flavor of a question that I get periodically and have gotten periodically literally for years. It goes like this:

“Hi Leo, I’m considering a career change and leaving the world of business for technology. The past 15 years of my life, computers have been an ongoing hobby and interest. In my circle of friends, I’ve become the “go to” guy for computer help.

I’ve installed new hardware and software and have become proficient at troubleshooting Windows and Linux plus minor experience in HTML and graphic design. My next area of curiosity is programming. I guess you could say, I’m well rounded. If you were to start your career over today, in technology, what area of interest would you specialize in? I guess what I’m asking is what baby steps I should take? Friends have recommended that I must select a specialty.

In my business life, I sold radio advertising, so I lean towards being creative but also analytical. I’m 55. Does my age work against me? I appreciate any advice or insights you can offer. Thanks, Scott.”

I get this question, as I said, in various forms from a wide variety of people over the years wondering what to do and where to go and how to start and just what technology to choose and so forth. Scott, I absolutely love your version of this question because you’re bringing two things that a lot of people don’t bring to the question. Your version includes both experience and experience, and I’ll explain what I mean by both of those in a minute.

Now, I’m a huge believer in doing what you love. Now, the old adage, “Do you what you love and the money will follow” – now I’m not so sure about that. I can certainly envision loving things, loving doing things that don’t really pay so well, but what I do know is that if you’re doing what you love, three things start to happen.

One, work doesn’t seem so much like work anymore. It almost becomes play. I know that’s true for me. You naturally continue to get better at your work, because you enjoy doing it and end up doing it more. And the opportunities that are presented to you in ways to utilize your work naturally increase.

Now, I got lucky. It’s a longer story, and I won’t get into great detail here, but it all started basically when I was a teenager or almost a pre-teen where I was essentially treated as an adult by a friend of the family who showed me some of his work in electronics. He was a TV repairman. That got me interested so that a few years later, when I applied to college, I expressed an interest in electronics.

The college then placed me in the College of Electrical Engineering out at the University of Washington where in my second year in school there, I was required to take a class in computer programming. The rest, as they say, is history, because that one class within a just of couple of weeks of starting that class, I realized not only did I love doing that, but people would pay me to do it. It was like the perfect storm for me.

Now, I’m a generalist. I love doing all sorts of different things related to technology. In many ways, I consider myself a jack-of-all-trades and master of maybe one or two. I’m really not sure that I could pick a specific technology to specialize in. I have written before that one of things that I would do over if I had the opportunity to do it over would be to spend more time in English class.

That actually has little to do with the technology and is more of a reflection of my understanding of how the world works and how important communication is. It’s not really about having become essentially a writer as part of Ask Leo! but an understanding of just how important written and verbal communication skills are in the workplace, no matter what it is you do.

But I don’t think that’s really getting to the meat of your question. I hear from a lot of younger folks who are interested in a very specific answer to this question. What they’re looking for is: learn this technology, go to this school, learn this programming language, get this certification or degree, apply to this company and you’re set.

It just doesn’t work that way. Life is too complicated, and individuals are too different from one another for that formula to make any kind of sense in a broad, broad way. Personally, I think that choosing a technology or a programming language. as it’s often phrased, when I hear from others isn’t nearly as important as simply being comfortable with technology.

Having a fundamental understanding of how things work, how technology works, how computers work, what they do, how they “think” (if you want to put it that way). The technologies that got me into Microsoft over 30 years ago, are not technologies that I use ever day today. They just aren’t. They don’t apply anymore. The world has changed. Things have moved on.

That being said, though, the fundamentals, the way of thinking, the way of understanding, the nature of technology and computers and programming languages in general, absolutely, these are the things that I continue to use everyday – not just as I support a system or write some software, but even as I answer questions, it gives me that insight that says, “You know, the way the computer is ‘thinking’ it’s kind of expecting this, or that means this error message probably means that.”

Those fundamentals – that’s what’s important, because those then let you build on a career that will change as technology changes. And I’ll be clear, I’m still learning – every single day I learn something new about technology or about computers or about something relating to my career. Heck, that’s one of the reasons that I love what I do. I enjoy learning new things everyday.

It’s exciting; it’s awesome; it keeps me interested; it keeps me out of trouble. You get the idea. For me, the lure, the allure of learning something new everyday about this technological world, about technology in general is part of what makes it exciting and refreshing and new every day, and ultimately, it’s one helluva a lot of fun!

If I had to do it all over again, you know, to be honest, it would really look an awful lot like it does today. The path that got me here may have some changes and you know, minor course corrections, but ultimately, what I did, how I got there, the things I learned, the way that I learned them, which is mostly learning by doing, I wouldn’t change, because I ended up in a really, really good place and am enjoying my career.

I think that you can too, so my advice to you – experiment. You might have that light bulb moment that says, ah, this is it, this is the thing, this is where I want to invest my time. This is what I really love doing. It may be a specialty. I know of many people who have spent decades working on the exact same technology as that technology has grown.

I couldn’t do that. Right? Like I said, I’m a generalist. I’m much more interested in trying and playing with different things as the technology changes, as new things become available. I don’t know where you are on that spectrum and I think that’s something that only real experimentation and dipping your toes in various places will help you understand.

Either way – enjoy the journey, learn from the journey, and leave yourself open to opportunity. Now, the reason I said that you have both experience and experience is this: Unlike a lot of people, you’ve already started what I’ve just been describing. You are already playing with technology.

Heck, it’s what’s causing you to consider a career change from wherever it is you are into a technology-related field. That’s fantastic! You’re already on this path getting an idea of the kinds of things that are going to interest you and maybe be the thing that becomes your passion, your love, your whatever it is you’ll enjoy doing everyday.

That’s great; that’s an experience that a lot of people simply don’t have and don’t bring to the table. The other experience is yes, the experience of age. Now, I’m going to turn 58 in a little over a month so we’re of some of the same demographic, you and I, and to be pragmatic, whether it’s right or wrong is a different discussion, but to be pragmatic about it, yeah, our age does affect our opportunities.

I wouldn’t expect Microsoft, for example, to hire me, in part of because of my age. It’s a company full of young people, by and large, and it’s human nature, again, politically correct, or not, it’s human nature to feel more affinity for people that are like us, as a result, younger people probably hire younger people. They’re looking for somebody like them; they’re looking for that younger energy and so forth.

Now, what you and I of course bring to the table is this maturity of age. We’ve been through the wars, we’ve done business, we know how things work over the long haul. We end up finding companies that appreciate that, that’s fantastic, but my point here is that there are simply going to be places where, again from a purely pragmatic standpoint (I don’t want to say whether it’s right or wrong, it’s just pragmatic) that yeah, we’re not necessarily going to be at the top of the hire list.

So with all that being said, yeah, we do bring that maturity that a lot of these companies need, or we bring the maturity that allows us to set out on our own. Now, I have no idea if you’re of an entrepreneurial mindset, but the internet in particular has created this world where the opportunities to just set up shop on your own and do business, you know, make a living on your own from home or wherever is enormous; it’s incredible.

Take a look at just what I’m doing. I’m standing here in an office in my home recording a video. I’m developing websites; I’m doing this all out of my home, by myself. I’m self-employed. There are so many different kinds of opportunities along those lines, that it’s staggering. It requires maturity; it requires a certain mindset; it requires a certain ability to self-motivate, but if that’s you, if you’re of an entrepreneurial mindset, that could be an option or a very lucrative option if you’re that kind of person. If you’ve got that entrepreneurial mindset.

As you can tell, that’s where I’m at. If Microsoft even did want to hire me, I’m not I would take it. I’m not sure that having done this on my own for the past 14 years now, I’m not sure I could work for someone else again. I enjoy what I do and controlling my own destiny too much. It doesn’t work for everybody, but for a class of individual and especially if you’re of an age where some of the age itself might be working against you in some ways, entrepreneurism and setting up your own shop can be a very lucrative approach.

So my bottom line recommendation here isn’t nearly as specific as most people want to hear. Do. Start playing with the technologies that you are considering. Take classes, build computers, whatever it helps you to learn the various types of technology, the various types of opportunities that are out there but also that exposes to the different aspects of technology so that you can maybe feel that calling to one particular type or another.

It might end up being that everything appeals to you, which is great. That’s kind of where I’m at, or you might find that one thing that really, really rocks your boat. That too would be fantastic. Then do more. My recommendation to people has always been the best way to get a job with a company is to have experience, which of course which is that old chicken and egg. If I don’t have experience I can’t get a job but if I don’t have a job, I can’t get experience.

That last piece is simply wrong. You can just start doing. You can volunteer your time, volunteer the skills that you do have. Teach a class. There’s nothing like teaching technology to force you to learn technology. Trust me. I teach, essentially, every day as I answer people’s questions. That’s one way how I learn so much is by being to be forced to go a little deeper every day by the questions that I’m being asked.

Then, yeah, get paid. Once you understand what it is you love doing, and by that I mean, the stuff you would do even if you weren’t getting paid for it, get paid for it. I can’t tell you how, because it depends way too much on way too many things, not just the opportunities in your area or the opportunities in your field, but the opportunities in your locality. If you’re talking about setting up shop, would your community support it? I don’t know. Are you the kind of a person who could be an entrepreneur? I don’t know.

These are the kind of things, though, that I want you to think about: is once you understand is you love what you would do no matter what, that’s what you want to get paid for; that’s what you want to understand how you would then go and set up and actually turn into a living in addition to a love. Most importantly, just make sure that this is stuff you love, that you enjoy doing. I mean, for me, I enjoy what I do so much that sometimes I have to get out bed early because I’m just waiting to do whatever it is that day’s tasks might be. That’s how much I enjoy it.

If it really is the kind of stuff that gets you out of bed in the morning, gets you excited to “go to work” that’s a sign, that’s a sign that not only are you going to enjoy what it is you’ve chosen but it’s something that in all likelihood is going to reward you for doing that and doing it well. Kinda like me, you’ll get to play and get paid for it. And that’s pretty awesome. Now, I know mine is only one path, one example, and I’ve been incredibly lucky. If you love what you do, particularly if it’s related to technology in some way, how did you get there?

What is it that led you to doing what you’re doing today? What led you to technology? What was your path like, and perhaps most importantly, what advise would you have for others that are contemplating this same path be it an initial path or a career change that somehow involves technology?

As always, if you are watching this somewhere other than on Ask Leo! here’s a URL, go visit that page, that’s where you’ll find this video along with moderated comments. I would love to hear your stories, and I think your stories would really, really benefit many others whom I hear from frequently on this topic. I’d love to hear what kinds of things drove you to the career you have today particularly if it’s a great one. And of course, if it’s not, are there mistakes that you’ve made that we can all learn from that would help people down a career path that they would love, that they would end up enjoying?

So, let me know what you think. Let me everyone know what you think. Share your story, leave a comment and I look forward to talking to you again next week. Take care everyone.

Posted: July 25, 2015 in: Video Commentary
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I'm Leo Notenboom and I've been playing with computers since I took a required programming class in 1976. I spent over 18 years as a software engineer at Microsoft, and after "retiring" in 2001 I started Ask Leo! in 2003 as a place to help you find answers and become more confident using this amazing technology at our fingertips. More about Leo.

7 comments on “On Career Change”

  1. Hi leo,

    great video. Yes i totally agree with loving what you do will be a great benefit.
    I have to be honoust, i recently started my blog and then i’ve found you. And it will be basically the same kind of blog as you’re having.
    Although i’m just starting out.

    But i don’t really believe in competition, because we are all unique and bring other points of view to the table.
    As of now, i’m having a fulltiime job in the production/warehousing section, but i love technology so much.
    I’ve been playing and learning about computers since the last 20 years and i used to fix computers in my area for people and through advertising.
    i wanted to take it to the next level, so that’s why i started my blog.
    I’m married to my wife from thailand and my plan is to build an online income and move to thailand. i don’t need to get rich or something,
    but a steady income would be great. So i can provide for us.

    Keep up the great work and i will keep following you.


  2. I got started working from home back in 2003. I wanted to continue to be a stay-at-home-mom but at that same time, I wanted to contribute to the family income and be challenging at the same time. I felt confident that my Bachelor of Science in Business Administration would enable me to find something flexible. When I say it took me years, I’m not exaggerating. It was four years before I really got lined up with steady work. And I learned some hard lessons along the way. There is still about $1400 floating around out there with my name on it that I was never paid. I have learned so many new skills and discovered that I love HTML code and working with websites in addition to the customer service work that I truly love. I would encourage anyone who has marketable skills and who wants to get their feet wet working from home to create their profiles on any one of these sites (or all of them if they wish):,,,, These are good reputable sites that greatly reduce your risk of not getting paid for your work. And whenever you have the chance to pick up a new skill, jump at it! The more technologies you are familiar with makes you that much more marketable. But make no mistake, if your goal is to work from home, you have to take it seriously. Yes, you have freedom and flexibility but you have to be disciplined and professional about your work.

  3. To the fellow thinking of moving into IT at the age of 55. Here’s my advise: Don’t Bother for your age will surely be used AGAINST You as it has me and I’ve got over 30 years of technology service and support that covers multiple platforms.

    I was laid-off over two years ago and since then have gone on over 50 interviews, in-person/telephone and as soon as the employer realizes they’re dealing with someone my age, all bets are off and they take evasive action the likes of which I’ve never seen. A position advertised/described wherein the new hire could come into the job at either a I or II depending on experience and background I interviewed for wasn’t brought to my attention until the second interview and it was only then that one of the interviewers blurted out to me that they were looking to fill the job at the entry-level. With over 30 years in IT, it was obvious at that moment I wasn’t going to be asked back for a 3rd interview and this was because of my age. In yet another interview, and this with the state of Nevada, I had a deputy director in an e-mail reply say the following: “the candidate we offered the job to had on-going direct experience with our systems because he worked for a contract vendor that has been doing our maintenance. He had the same advantage over every other candidate which is why he got the job offer.” I guess this explains why the woman who sent this is a deputy director. Talk about putting one’s foot in one’s mouth!

    But there’s another issue/reason why it’s going to be difficult for this career changer to break into an IT job at his age: existing employee’s. I’ve lost track of the number of times I found out after I’d applied/interviewed for a position that an existing employee, with less experience then me was offered the job. Employers want them Young, Dumb and Cheap which they won’t get from me. On the other hand, my salary demands don’t have me asking to start at the top of the pay scale but too many employers think that’s what I want. That’s not the case, but I’ve yet to have had the opportunity to prove them wrong, because I get turned down on account of my age. But I’m now seeing plenty of payback in the last 12 to 18 months. Numerous positions I’ve applied to in the past are once again being seen advertised again. Hmm, seems to me as if they can’t keep the job filled. Could it be because younger individuals move around and are not staying with their employers? Sure looks like it to me. But then considering the crap that’s been pulled by employers with me with just trying to get an offer, it really does make sense for employees today not to have ANY loyalty to the employers. Hell, what’s the point?

    Earlier this month I applied to a position which required the old fashioned method: download application, print it out, fill it out by hand and then proceed to Post Office and Mail it. Received a call asking that I come in for an interview. So after having to spend the night in a hotel and traveling over 400 miles roundtrip to do this interview, last week on the 20th I received a call from one of the individuals that was in the interview. He asked could I return next month for another interview. I was not given a specific date/time for this interview, instead I was told I’d be contacted the first week. Sure I said. Well on the same day I agreed to another interview, this employer turned around and advertised the position once more on Craigslist! Three days later, on the 23rd and it posted the job to the website I saw it on originally as well. The new deadline to apply: July 31st. Clearly after seeing me at the interview and the three interviewers (all of whom are in mgmt) realized, “oh gee, Mr. Kirschbaum is old and we want someone much younger!” Considering the location of this employer with reference to larger urban areas, I was likely one of two people who applied and given my background, I knew I’d be contacted for an interview.

    But having a degree in electronics, and holding CompTIA certs that include A+, Network+ and Server+ along with an MCP and additional certifications from the ETA as well as holding not one but 2 certificates as a customer service specialist and being acknowledged as a SME with the ETA, as long as I’ve got some grey in my hair it doesn’t matter what I’ve got on paper or in my past. Like I said, employers want Young, Dumb and Cheap. And as far as being a Veteran goes, it doesn’t mean a hill of beans. Employers can brag and boast about how they go out of their way to hire and employ us Vets but it’s all just a bunch of marketing and advertising malarkey so the employer can cop some “good press”.

    I’m a consultant now but even that has it’s pitfalls. Work I did for a business that’s based out of Ronkonkoma, NY earlier this month does not look like I shall ever get paid for it. Isn’t the first time and probably won’t be the last.

    So to this fella who’s considering moving into the technology profession at the ripe old age of 55, sorry but you’d have much better luck with a job in the medical health field, seriously. Anyone over the age of 45 in my profession is seen as a dinosaur. This is true even if you keep up to date with what’s going on with changes to technology. I don’t have MS-DOS running on any of my computers but I’m still very much familiar with and know how to use it.

  4. Great piece of mentoring, Leo. I always tried to teach my students the same lesson about doing what you love. From personal experience I would add: if you don’t love your work, it won’t be fun. And if it isn’t fun you probably won’t do it very well. Which means your work won’t be fulfilling (which is sort of a highfalutin’ synonym for “fun”) — notice the vicious cycle there. This is not just a self-centered argument; society (the consumer of your products or services) suffers as well when your work is less than the very best you are capable of.

    Here is my story of a mid-life career change, which serves to illustrate this principle. After graduating from medical school in 1957 I chose a career in academic medicine, eventually becoming a full professor and the head of a division of cardiology in a university medical center. During that era what had been called a Three Legged Stool of research, teaching, and patient care (each of which for me was great “fun”) grew a fourth leg, which in my institution came to dominate those traditional duties: generating patient-care income to replace dwindling state and federal sources of funding. Finding myself in conflict with many university policies, and no longer having much fun, at the age of 51 I decided to make a clean break, move to a different city and state, and join one of my former students in setting up a private practice.

    Building a new practice from scratch, working directly with my own patients (I found teaching them nearly as much fun as teaching medical students and house staff, incidentally), developing my own computerized medical record system (an avant-garde idea back in the early 1980’s), helping to pioneer the then-new field of cardiac ultrasound, and gradually becoming recognized as the go-to guy for solving difficult diagnostic problems in my area, proved to be rejuvenating, and every bit as fulfilling (i.e. fun) as had been my earlier days in academia. And thus I highly recommend making a mid-life career change.

    But… Our practice grew rapidly (eventually, after I retired, becoming the largest, 28-physician, cardiology group in the state) and we had to expand. As time went by, young candidates to join our group (often represented by agents, much like professional athletes) seemed to be more-and-more interested primarily in making money, not primarily in “having fun” as I have defined that term here. And, although they were very successful in achieving their goals, they didn’t seem to have much fun. And I think their patients–and, I fear, most consumers in what has become our enormous Health Care Industry–suffer as a result.

  5. Hi Leo,
    I’m a 60-year old male at Chennai, India. I’ve shifted my career at the age of 50 years. At that time, I’d been in business management for nearly 30 years that includes many failed attempts in own businesses & big losses. I studied a course on ‘Technical Communications’ and got into employment after significant trouble thanks to timely help from unknown persons. After initial hiccups in retaining employment, I’m with a company for nearly 5 years now. During this period, I tried to shift from existing company, but as someone pointed out, every employer was looking for younger guys. Yes, my age was working against me.

    In my employment too, as a lone writer in my company, my job seemed to be secure but is a dead-end too. Last year, they gave me a lesser revision for the reason that I’ve reached the market maximum level for my position already. They said that the revision itself is due to my good performance record! This year, they are retiring and re-employing me as a temporary employee with the same pay without any increase! Though I still like my job but aged career shifts entail difficulties in both getting and being treated equally unless probably if one can offer something difficult to get!

    Now, I see I cannot hope to be in employment for long and it might end sooner than I think. Yet, I want money for my living. So, I looked for shifting to another career that can support me as a freelancer. After some searching and dithering, I’ve decided to become an English-Chinese-English Translator. Though learning Chinese from scratch won’t be easy, as I’m not passionate about Chinese, still I believe I can do it good enough. As you say Leo, we aged-shifters have to stop looking for regular employment and develop entrepreneurial mindset. There is no option if we want to shift and restart. Do we have?

  6. Hi Leo,

    Thanks for making a video related to my question. Just awesomeness and I loved it!
    Along with reply’s from “Ask Leo fans,” you’ve firmly planted the seeds of inspiration for my future endeavors.
    And like you I’m a generalist loving everything related to technology and computers..

    After spending over 15 years of my life in business and radio advertising sales, I lean towards being a risk taker and entrepreneurial
    and I am considering starting an online business.

    I’ll keep you posted on my progress.

    Leo keep up the great work!




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