Ask HN: Starting a Career in Programming at 61?

177 points by wofo ↗ HN
Yesterday I had a conversation with my dad (61), in which he asked me whether it made sense to start programming professionally at his age. It is kind of a crazy idea, but I promised him I would ask my "hacker friends" about it, so here I am ;)

A bit more context, in case you are interested: he has worked as an executive at multiple companies in the past decades (CEO, CCO, CFO). As he grows older, he has noticed it becomes increasingly difficult to find work, even though he would love to continue working for the years to come. I think he feels inspired by seeing me thrive as a contractor, with access to a global marketplace and seemingly endless working opportunities.

He learned to program when he was a student, probably Pascal or Basic, but as far as I know he has never needed to use that skill in his professional life (though I assume his excel-fu is excellent, because that is the preferred "programming language" in a business environment).

I have no idea what to advise him, so I'm curious to hear your thoughts. Maybe I will even send him the link to this page so he can read along!

185 comments

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I had a colleague in a previous job who was actually employed as a trainer but picked up a lot of Excel VBA stuff that was "beneath" the actual development team and got so good at it he landed a pretty decent role at another company just working in Excel.

He was late 60s.

There is being a "professional programmer" who mostly builds large systems that put other people's expertise to work.

Even before the microcomputer revolution, back in the dawn of timesharing, there have also been "non-professional programmers" who write software to put wheels on their scientific, engineering, business, literary, accounting, medical, mathematical, artistic or whatever skills they have.

To be a professional programmer you're really going to have to learn how to whip other people's bad conceptual models into shape, track down difficult bugs, not use an O(N^2) algorithm when an O(N) algorithm is available and N is large, understand the difference between C++ compilers and whatever details turn up to be relevant in a particular case. (e.g. You're never going to know all of these things but you have to find out the ones that are relevant to your project!)

The non-professional programmer is going to be more focused on the problem domain even though they still sometimes might need to figure out something technically hard to make their system work.

Sounds like he could afford to pay for a boot camp for some immersion and doesn’t need to stress as hard about landing a job after.
> he has worked as an executive at multiple companies in the past decades (CEO, CCO, CFO). As he grows older, he has noticed it becomes increasingly difficult to find work, even though he would love to continue working for the years to come.

Finding a business position that's a good fit for him would be a much easier way to stay employed until retirement than switching to programming.

I am almost the age of your dad and I have been a professional software engineer since 1986. In the first years I worked with Pascal (VAX-Pascal and Turbo-Pascal.) From 1990, I mostly used C and C++. The last two years I have been working with C#. Now that I am getting a bit older, I noticed that it takes me more time to get know a developing environment and all the libraries/packages that go with it. It is a big leap from knowing how to develop an excel sheet to, for example, develop a website with a database backend. I am always happy to have younger colleagues who are good at setting-up a development environment. Also being an efficient software developer is much more than knowing how to program.
Taking longer to get up to speed and setting up a development environment: I'm not sure that's a function of age. It's more likely because development environments truly have gotten larger and more complicated over time.

I've been programming for 20 years - the amount of environment / config / tooling stuff to deal with just keeps getting bigger and bigger.

My experience is the same.
Assuming he is currently employed I wonder if taking on some programming work as part of his existing role might be a good way to slide into it. If he knows and uses Excel then writing VBA would be a good first step.
This is really good advice. The amount of business critical processes out there running on excel spreadsheets is enormous. A small amount of automation of these using VBA can be a game changer in a lot of places.
I don't think it's vastly different from someone younger who wanted to shift career into tech without previous experience.

I would recommend him taking one or a few bootcamp classes to bring him up to speed, maybe focus on one area in particular (e.g. web development) then find a smaller dev shop where he could come in and support in a junior support role to start with and then take it from there. Maybe develop a few pet projects to build his portfolio in parallel.

It's not impossible but maybe manage his expectations a little bit that he's going to have to start more or less from scratch.

What is a “dev shop”? How do I go about searching for one?

FYI I’ve been a software engineer for like 5 years, but took the past 1.5 years off.

A small dev shop in my view is a company (1-20 employees) that typically develops bespoke applications as turnkey projects, either from scratch or leveraging some existing stack (e.g. Wordpress applications, Salesforce applications, etc.)

I would look for companies that describe themselves as:

- Website design agencies

- Creative agencies (look at their webpage if they also have development and not purely design)

- Design & Development agencies

You should be able to find a handful just through a Google Maps search.

Reach out to them and ask if they could use some junior development support, and if there's a particular area they need support in.

My advice would be for him to identify specific applications of programming that interest him and then focus on identifying the skills he'd need to develop expertise.

One approach would be product or industry specific. Maybe he'e really intrigued by applications of GIS and that could lead to exploring specific companies in that space and the talent they need.

Another would be open source. Maybe he's really interested in databases and could dive deep into that part of open source and find out what things he wants to do.

No guarantees with either route, but the older you get, the worse the odds are if you are just a person with programming ability like many others.

I am almost his age and despite decades of professional experience I am unable to get a job.

Of course, its likely that I'm doing something else wrong as well.

Where are you looking? I ask because ageism is definitely real in the industry, but it's not nearly as bad once you get away from SV and the the startup world. You may have better luck looking at traditional industries like banking/finance, manufacturing, and healthcare. These fields employ a surprising number of programmers.
I'm pretty close to that age, too, and getting work as a developer is certainly far from easy at our age... companies want young blood that's willing to work stupid hours.Fortunately for us, they write shit code, so...

The thing to sell is your experience. i.e. "consulting". The market is smaller, but the rates are higher, and the value you can deliver is orders of magnitude greater. That's a good thing (and a good feeling!) Nice to say, "I cost my client x, but I delivered 10x to them in cost-savings/profit."

I'm in my mid-50s and while I'm definitely not a high-flyer, I've found work for the last 15 years as an FTE of state gov't in the U.S. I've had friends who've been let go in the private sector as they passed 50, but government employers don't typically do such purges. It may not be easy to get into gov't service at your age, but it's worth a shot.

Also, I wonder you should create your own 'Ask HN' to uncover whether your approach to job finding may have flaws, since there are many older IT workers out there who are finding work.

Do Gov firms hire people without degrees?
As long as the experience of the candidate lines up with the position, I don't think not having a degree will be a deal-breaker.
I have a friend in his late 20s and he had trouble getting a job - took him about a year. He also has lots of experience at "good" companies such as Google.

Of course it could be your age/something you're doing - I don't want to deny your experience with the situation - but also sometimes things just don't work out.

I vouch what another comment said, take the consulting route. I've said this before, but in 2019 I've switched to consulting because I've wasted close to 6 months of that year applying to jobs. The hiring processes were that bad for me at the time. And I'm only in my 30s and didn't even have to consider any age bias.

Another practice is applying en masse, if you're not already doing that. I used to apply sequentially to jobs, picking only the best fit and going through the interview process one by one. A waste of time, bulk apply to dozen of job listing (and directly to companies) and pick the first company that throws in an offer (and which also seems decent during the interview).

I think the only way in that he's got a shot at is if he can leverage some piece of huge domain knowledge that he can bring to the table. At 61, i'm sure he can, but it's selling that that'll be the challenge.

Elevator pitch: "i've spent X years doing <highly specific business thing Y that everyone does in excel>, but i have a better way because it <1, 2,3>"

It's not impossible, but I wouldn't say it's worth it. From my experience, there is more ageism in programming than there is in management so it would be even more difficult to find work, especially without prior experience.
If he's serious about starting a new career he needs to be willing to swallow a bit of his pride, but starting as a test engineer is a great way to get a foot in the industry from what I've seen and from who I've mentored.

Show him Cypress or your preferred choice for integration testing and see if writing simple integration tests piques his interest. It's close enough to engineering that he should get a feel for what the job is like while being "relatively" easy to learn in a few weeks.

It's great that he is still up for working!

At risk of getting flamed...

It's tricky I think because even if he can learn to program to a suitable standard, I think the reality will be that people will see him as a "junior" but you will have a different working dynamic since it is easier for an e.g. 30 year old to coach someone who is younger if they are doing it wrong but could be tricky trying to coach an older person unless they have genuine humility, otherwise your dad might feel patronised or be offended by some youngster without the experience to coach well.

Another avenue, if it is just the industry he likes rather than programming specifically, he could probably get more distance by utilising his exec skills to do a technical management role like Product Manager, Product Owner or Project Manager. He could then get as much exposure to the programming as he wants without needing to produce as much of it as would be expected of a dev.

Don't know, just thinking out loud.

Was going to recommend a technical management role. This is a good call, imo. You only need to know how website/apps work, not the code itself.
Also thinking out loud...

I started teaching my self to code w/ the intent of getting a coding job at age 38, and I got my first coding job at 40. Breaking into coding was brutal for me. I couldn't get taken seriously as a junior. I just had to keep grinding until I was good enough that someone would take me seriously as a mid-level.

The way I did that was go super deep on learning Ruby super well. Then I found a company that needed someone who was really good w/ Ruby. They were willing to overlook my lack of depth in other areas because I had a skill that was critical to them. After starting the job, I had to work super hard to brush up on junior & mid level skills just to do my job at a good enough or better level.

After less than two years, people started thinking I was actually better & more experienced than I was. I could talk a really good game because I had spent so much time learning while I was getting experience, and then I started getting taken seriously for senior level roles. People saw my physical age & just assumed I was more senior & experienced than I was, so being older was actually an advantage to being taken seriously.

After about 5 years of coding, I finally felt like my work life balance was somewhat normal. I could start having a life again, stop learning quite so hard, etc. Now I'm just a normal, boring senior software engineer making a median-ish USA salary.

So I guess I'd say if OP's dad's path would be similar to mine, I'd ask him if he really likes software enough to spend a couple years learning to code & finding a job, then grinding for a few years to get to normal, and then enjoy 5 years of being a competent team member. It's certainly doable, but I think it's worth how bad one really wants this path. I think getting into software just for the money is not how I'd want to spend my 60s, but I'd absolutely do it if I found the coding enjoyable enough to self-teach & grind on learning for as long as it took.

It's also possible that other opportunities would open up just because of dad's knowledge of software. Just saying he likes to program, even if that's not his profession, could open up opportunities at a tech company doing other things, such as QA, support, scrum master, etc.

I'm curious at which point you were considered valuable ? what did you have to show ? some theoretical knowledge ? actually used products ?
I can say w/ certainty the second half of my coding career has been more productive than the first half :)
It would take him 5-10 years to become a competent programmer. Does he want to finally achieve stability in his career at age 70?

I would suggest that he become a business advisor to small companies. His expertise is invaluable and he could be useful immediately.

I disagree that it would necessarily take that long. Per the OP, his father is not starting from scratch, and has some programming in his background. Being a CEO, CCO, etc... We can assume his father is an intelligent and successful person.

Possibly, if his father applied himself, he could find himself a niche in which he would be adequately competent within 2 years. To include being a freelancer or independent developer.

As you alluded to, because of his father's business background, he might do really well in sales for a software related company or starting his own business.

I know the OP said it was "maybe Pascal or Basic", but having done this ~40 years ago, I'd argue that it is basically starting from scratch, unless he was actually writing Javascript the whole time for google sheets integrations

> Being a CEO, CCO, etc... We can assume his father is an intelligent and successful person.

Being unable to continue working as a CEO/CCO suggests he's not currently very successful, and to put it lightly, CEO "intelligence" (whatever that means) doesn't necessarily translate to the kind of intelligence necessary for software engineering

Ya for sure, that's what people don't understand. It takes years to really be up to speed and really useful (maybe you can shortcut it with bootcamps, idk, I suspect not though but maybe you would know enough to be good for some tasks).

I had a friend ask me same thing as OP. He was 50, out of work at the time (had been in a trade before) and wondered if he could get into programming. I don't want to discourage anyone from learning to program because you can do a lot of cool stuff, but to be seriously industry useful isn't a matter of months and a few online classes but rather some dedicated years.

And (this might be an unpopular opinion) it's much harder if you don't natively think a certain way. Some otherwise smart people find programming pure torture and the chance of them going through the years needed is pretty low.

I about to turn 37 and just got my first full-time job as a junior. I actually think my age has given me an edge, but one thing I do have going for me is that I look much younger than I am.
I also forgot to mention that I largely needed a mid level salary, too. Had a lot of debt to pay off.
Are you going to go into management? I’m going to enter professional coding work force in mid 30s too. Assume I’ll feel the same way the first couple years
> could be tricky trying to coach an older person unless they have genuine humility

Bingo. This goes for young people too, but is more important as we age or rise through the ranks. Accepting advice from an "inferior" with grace, humility, and thankfulness is key to gaining respect and learning at the rate necessary to stay on top of a field.

I've taught things to people who were a million times more intelligent than I and 20 years my senior. I gained so respect for them after seeing how quickly they learned, and how appreciative they were of having my time.

One thing I gleaned from the experience of working with these guys was how letting someone teach you something is a great way to impress them.

Yeah this is gonna be a human "problem", an emotional level requirement, if both are chill sharing their viewpoints, being positive then things are possible.
Accepting some advice or input on an individual item vs having someone 'manage' you are different beasts. As I come up to 50, and work with a group of folks ranging from 28-32... the age and experience gaps are highlighted often. I'm happy to contribute, and I do occasionally learn something from someone (often some specific tool I'd not seen before). But there's a resistance to 'learn' from me. We're 'equalized' on a 'team', and "we should all learn from each other!" is a common mantra.

I've done many of these projects before, and will raise issues. "Let's just see how it goes!" and "well... we might make some mistakes, but that's how we learn!" And I'll say "but I thought we were supposed to be learning from each other?" "yes!". "Why does no one ever want to learn from me?" I've done XYZ longer than these colleagues have been adults, but I'm never asked for stuff, people avoid my input, etc.

What's more interesting is that a couple of folks on the client side of the equation (contracting house) have been added who are older, and ... they're quite open to picking my brain. We mesh quite well, and have pairing sessions and learn from each other (but I'm giving more than taking in those cases). With the younger crew... there's just a real standoffishness, and focus on 'team' and 'learning from each other and our mistakes' but... they're willing to make mistakes (repeatedly) vs taking my input to avoid those mistakes in the first place. The client's new person seems to have picked up on this and is raising some issues.

For a while, I really thought it was something wrong with me, but as I jump around between clients/contracts/etc, it seems to be more age related. The larger the age gap, the less impetus there is to work 'together'. And... I'm trying to think back to when I was 25... how open would I have been to 50 year old colleague's input? If they were 'management', I'd have to. Otherwise... possibly not? Hard to remember that far back, other than that I thought I was invincible :)

Hi! Thanks for the honest response. I'm your age, and find the same reluctance from young people to listen to me when I've been down that road before. They really do have to learn from making mistakes, as they keep telling you, and can't learn from your experience. I'm not defending them for not taking advantage of the diamonds right in front of them, but I also understand their need to experience things for themselves. After all, how did you learn?
Rather than “that won’t work because of X”, I may say “here are some potential problems to watch out for”, or just ask a question like “OK, and how will you handle X?”. That message seems to get through better, and at least helps people recognize the mistake earlier.
Partially through trial and error, partially from other people, partially from books, etc.

It's not so much that "these young kids won't listen" that's annoying, but this mantra of "we're all here to learn from each other - that's how we grow!". Except... if it's me. Then you choose not to learn from me. Or older people in general. Just drop the "feel good we're all a team" facade, because it doesn't represent what you're actually doing. The disconnect is the problem, not the actual behaviour.

Youth is dumb.

When I was in my 20's, my mentors were all 50+. And, quite often, I would have to hit the wall before the good advice they gave me made sense. I realized later that I was really irritating to them at many points. It took me, like, 4 times hearing "You might want to think about that" from my main mentor before I started mentally translating that to "Dumbass. You're about to hit the wall. Again."

I am not a smart man.

They stuck with me because the magnitude of my vector was large (ah, the province of youth--boundless energy), so, even if I had a significant amount in a useless direction, I also had a significant chunk in a useful direction. And I would learn--I rarely made the same mistake (but I was quite good at making new mistakes ...)

However, if the people around (not just the kids) really don't understand that you're an expert at what you do, you really should think about getting a different job. If the consultants are willing to pick information from your brain, that's a good sign that you really do know what's going on. In return, you should make use of their people network--poke at the consultants you think are good. And right now is a good time to be making such a job change.

Ageism is a thing. On the flip side, the number of greybeards in this field continues to increase year on year--the people who learned computers as kids in the 1980s are now hitting their 50s.

Good luck and hang in there. You're not alone.

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I found myself in an interesting position: on one side I manage a group of people,where most of them are much younger. So it's nice to be able to tell that that you do x and you'll get y. For instance, I made someone a team leader recently and did tell that it is likely that they'll get some resistance from others because of it. Fast forward 3 weeks and now I have to deal with the exact thing I mentioned. On the management side, we do have a wider range of people in terms of age and seniority. It's so refreshing to be in a meeting where someone says: yep, I've done this 20 times previously, these are the common mistakes we are likely to make. I don't want everyone to be my age in the company,a mix of varying experience is great.
> Bingo. This goes for young people too, but is more important as we age or rise through the ranks.

This is more personality in general than age. There's just as many cocksure youngers as there are grumpy olders and neither want to learn from you.

Yeah, it's really difficult because a lot of the drive expressed in OP is for a new source of opportunity... The problem is that ageisms and such definitely take root in our industry, trying to work healthy hours at a startuppy place when you are older seems very precarious. I think you are on point that technical management has more availability, if that's the constraint.

If the constraint is instead that programming looks fun but you want to get exposed to as much of it as possible, I mean, I would suggest that OP’s Dad start building an indie game or so? Doesn't have to be a bestseller to sharpen thinking about design and aesthetic and underlying mechanics and state and data structures... I work in web but the amount of framework churn and such is kind of something I wouldn't force others through.

If you did want something more webby, you would want to practice with something you find interesting... If you wanted, maybe something that touches a lot of other technologies. If you think about writing your own GitHub, you start with git repositories and cloud hosting and deployment, you can move into CI/CD type workflows pretty easily, maybe that is a better way to start off web programming?

The other thing I will say is, Big Tech companies are often places where you can get one role and then ask for their developer education tracks where they teach their accountants etc how to become developers if they want to pivot. Say for example, being a manager at Google but having some 20% project that lets you contribute code and get feedback. Bigger more established companies have fewer problems with ageism, because they are much more sensitive as lawsuit targets for those sorts of things, so they have to get their s** together.

Also worth saying, the prior job history is an asset. A lot of developers do not speak business-ese. If you are a solid programmer who can talk to C-levels, you are a potential CTO at the right sort of place. Because you can translate, and because you feel comfortable walking into a contract negotiation with some client as “okay, how can I not say ‘no’ to everything but push back on the really hard problems while ‘yes, and’-ing all of the tractable stuff to get them on board.” Consultancy is one of the ways to do that, but not the only one. But worth calling out that as an asset if it helps focus the journey more.

The flip side of this is true as well. Ageism is a real problem in our industry. People are just more patient with young college grads and more willing to help them out. As somebody who transitioned to SWE in a big company(FAANG) after a decade of wireless communications research, I found out despite all the processes and supposed practices a big company has in place to onboard people from different backgrounds, you need to rely a lot on your teammates for the tribal knowledge to get anything significant done. And people are far less helpful than they think they are. Often they assume things because in their minds X years of experience means you should already know this stuff. Almost all of it is non technical and specific to the company so you won’t have a way of knowing it beforehand but that consideration is readily given to a fresh grad than an experienced person. Also a lot of the times tenured people will feel insecure/threatened about/by someone else joining at the same level and would constantly point out their shortcomings in order to maintain their place in the hierarchy. Was oblivious to this until I was managing people and saw newer experienced people joining the team face this. Had to coach people to stop them doing this unconsciously.
Well said. Thanks for the honest contribution.
How does working remotely seem to affect ageism in software development?
Honestly, have been long tenured (comfortable) at my current job for the whole of pandemic so only have second hand experiences through my direct reports. But on the whole I think remote work has made this problem kind of worse. When I was new I could walk over to someone, gauge their mood or how busy they are and have a direct conversation. Even if I lacked the ability to communicate my problem clearly it was definitely easier to get help. They could just see where i was stuck and get full context. Here for every simple thing people have to ping one on one on DMs or in group channels. There are few problems with this. One in large channels a person who asks a lot of questions is looked down upon. (Shouldn't be in an ideal world and we keep emphasizing this with processes and what not but it's human nature). Plus unlike an in person conversation every question you ask becomes a part of permanent/semi permanent record which discourages people from asking questions. Also you don't know when you are interrupting people. Even if you dont expect an answer right away when the person doesn't respond for a long time you naturally feel resentful. And repeating my earlier point it's much easier to provide full context when somebody has your undivided attention by showing them instead of typing out what you think the problem is.
If you're not working fully async, you can always ask the person to schedule a call where you can discuss X if you can't come up with one simple question.
Anecdotally, ageism seems to mostly exist in FAANG-type companies, web dev, and startups. If you look around at other industries like logistics, transportation, etc. there's less ageism.
Ageism is higher in companies in domains/work with lower barrier of entry, such as the ones you also identified like web dev, mobile apps and so on.

Ageism is less in domains that require domain expertise and hence have a higher barrier to entry for a newbie. Look at systems engineering, hardware, semi conductor, deep science and so on.

Ageism is a fundamental truism of all society throughout history. It's pretty much baked into the species via evolution.

* women are unable to reproduce until a certain age.

* women stop being able to reproduce at a certain age.

* NOTE: we need not delve any further into the inherent ageism of female biology.

* women select men for mating for a multitude of reasons, of which includes the dichotomy of dominant men.. who (for young women) tend to be slightly older then the men of the woman's own age group.

* men compete with each other for dominance, and age is a factor. Young men have a strength advantage, older men potentially have more experience.

* dominant men who grow older, become less dominant, etc... are no longer as useful for mating.

* older dominant women tend to have different selection criteria, they tend to select younger males who are less dominant then the other males of their own age, yet more so then the men of the woman's own age.

* this is not an exhaustive list...

Older men & women tend to be less useful beyond natural selection, but evolution is a great starting point.

Ageism is everywhere, but I'm surprised by your anecdote that it's more intense in FAANG-type companies. I wonder why?

Perhaps the FAANG working environment is competitive? Perhaps men & women are competing with each other for a kind of workplace dominance? hrm.....

I think you're right, but there would still be some hope in the "Don't call yourself a programmer"[1] avenue.

If he can sell himself not as a programmer, but as someone who does X with programming as a tool that they're going to use to do that, preferably where X is something that he has some expertise in from earlier in his career, he might be able to get people to look at him as an expert X instead of a novice programmer.

[1] https://www.kalzumeus.com/2011/10/28/dont-call-yourself-a-pr...

The probability of succeeding as an atypical programmer is directly proportional to your general enthusiasm for programming.

Someone who has been constantly hacking and building programs for fun on the side while working a different career, and finally thinks it might be fun to do programming for a living at 61: absolutely.

However it sounds like he doesn't have a prior interest in programming. Even for someone in their early 20s I don't recommend getting into to programming for the job (in your 20s this means being a software engineer for the money, for your dad it would be they like they type of schedule/work you have).

This isn't because of some ideal that "real programmers should be passionate", but because there is a reason that despite a massive rise in bootcamps it's still hard to hire devs: most people don't enjoy programming enough to do it for a living.

I love programming, love computer science and ultimately prefer data science work because I don't love software engineering work for 8 hours a day. So even someone who really enjoys programming might not necessarily love software engineering. If your dad was exposed to programming in college and then spent 40 years without ever picking it up again, it's likely he doesn't really enjoy programming and even more likely that he really won't enjoy learning all the tooling and frameworks required to work as a software engineer today.

tl;dr if your dad is the kind of person building a k8s cluster for fun on the weekend, or likes to hack together toy react apps in the evening: the he absolutely could transition. However it's fair more likely that he currently likes the idea of being a programmer much more than he would the actual work.

the OP's father could always try programming as a hobby, see if it suits him, and if so try to find opportunities to do work for others.
I would suggest technical recruiting, you can do that until an advanced age, and it can even be a benefit to attracting senior level people as a recruiter.

My dad did similar, after going back to school in his mid 50s and getting a CS/cybersecurity degree, he tried the engineering side for a bit but ultimately went into technical recruiting for a big enterprise, which is a six figure position.

With all his expertise, he can definitely bring a lot to the table being a consultant or mentor to all kinds of businesses.

Regarding programming, it depends if he just wants to work or work to earn money.

If the former, he could look at OSS projects that interest him, there are so many! He could make meaningful contributions (for the project and for him)!

If the latter, he can definitely give it a go but maybe not get his hopes up too much. He could start his own startup/blog/company though which might not be a bad alternative to paid work.

Also he could look at the no-code tools which would allow him to build stuff quicker than learning to program. It would probably be a step up from Excel already and he could see if he likes it and wants to dive deeper (some contractors are specialized in building stuff on top of no-code tools)

Anyhow, good on him to want a career change at 60+, I wish him all the best!

I would say yes absolutely. He doesn't have anything to lose.
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Given his background I think he should become a recruiter that peddles the over 40 tech crowd. That way he can dabble with programming on the side, leverage his business acumen, and see first hand whether there is a market for old folks in tech.
If he has to make enough money to support himself then I'd say it's a bit tricky. If it's more for keeping busy and the mind sharp then yes, go for it. Especially if he has a lot of domain-specific knowledge from his time in management.

My grandpa learned programming, (BASIC, on a TRS 80) when he was 80 and got proficient at it quickly although it was just for fun.

> As he grows older, he has noticed it becomes increasingly difficult to find work

Programming/software dev is not a field I would choose if I were trying to avoid age discrimination. It can be hard enough for 61 year olds who have been in the field for 35 years and have all that experience to find work.

I'd encourage him to do it as a hobby, but don't get his hopes up about being able to find steady work doing it.

I don’t know his motivations to become a programmer.

However with his experience as a CEO, CFO. He might want to look into becoming a Data Engineer, BI consultant, Data Scientist or Data Analist.

With the experience you mentioned he might be better at understanding how the “business” thinks and what they need. Therefore a lot of his domain knowledge could be applied while being in a technical role.

Most of the roles I mentioned involve some programming but often that can also be drag and drop tools.

Good luck!

If I were you, I would ask him to study up and then give him parts of my projects(you said you're a contractor) and we can see if it works out or not. If it does in a couple of years or four he can be a contractor himself under your mentorship.

Maybe thats what he's asking anyway ;)

Plus, he gets to work with his son which is maybe what he really really wants.

It is important to distinguish between needing to work and wanting to work.

I would try to identify an ecosystem where he could start building on his own: Custom Shopify functionality, Wordpress plugins etc. he can try to find small customers with simple needs and scale up as he learns. The ecosystem will provide him some guardrails and shrink the surface area to something manageable. You could coach him as he goes if you have time.
2 things: age & language

1 - age

> As he grows older, he has noticed it becomes increasingly difficult to find work, even though he would love to continue working for the years to come.

There’s a significant age bias in the tech community that might be hard to overcome.

He is in a protected age class though: https://www.eeoc.gov/age-discrimination

Just make sure he knows his rights during the hiring process that it’s not acceptable for a company to not hire him based on age.

2 - language

Learning a new modern language like Node/JS will be a brutal race to the bottom in a highly competitive marketplace.

However there are some jobs that pay great money to folks who know older languages like COBOL, Perl, etc., maintaining old systems. And I’m guessing he’ll find the work and coworkers more relatable. These jobs are just much more scarce.

A question he might get from having an impressive C-suite resume and applying for programming jobs is: why? So just be prepared to answer that.

And probably have him build one or two personal projects so he can make sure he likes the process and has something to showcase.

Good luck!

Does it make sense for him to try and become a professional programmer. No. Not at all.

However, using programming tools and concepts to provide more value than his younger Excel-munging peers. Definitely, and will help him figure out what he is good at.

Subscribe to Datacamp and start learning python. Get some of those Excel spreadsheets that executives like to drown each other with and start doing some business analysis on them in jupyter notebooks. He can definitely find an edge doing financial analytics, financial forensics, that sort of thing.

We (programmers) would be shocked at how bad those business spreadsheets are. He can use his experience, and desire to learn, to find plenty of work munging executive financial and other data using programmers tools.