Ask HN: How to restart tech career from scratch at 36?
This last decade has been a tough one and I find myself with a deep sense of stuck-ness and hopelessness.
A little background: Due to familial/personal circumstances, I studied a non-tech discipline through grad school with the goal of eventually getting into tech. After finishing, I eventually found my way to joining the founding team of an early stage startup where for the next 6 years I ran around like a headless chicken. Whether due to lack of education, experience, mentorship, or volition, I learned very little about how to systematically build a product and business. The whole experience was taxing.
I left the company to spend the next couple years working on my mental health. It became clear that much of my ineffectiveness was due to deeply-rooted fears, self-hatred, and maladaptive behaviors from severe childhood trauma.
Now at 36, I do find myself in a much better place. I've arrived at more of an understanding of who I am, my values, the kind of life I want to live. But I do feel as if I've squandered almost a decade of professional potential. I have good intuitive product and design sense, but have very very little in the way of effective skills, such as understanding and facilitating a product development process. Additionally, I have a very small network, if one at all.
Where do I go from here? Do I seek a mentor / life coach to help me build a practical path forward? Back to school? And where do I begin building a professional network? Will a company even look in my direction at this point?
Thanks.
It sounds like your goal is to be a Product Owner/Manager. I think your best career path is to start with Business Analyst or Project Coordinator types of roles at a SaaS company that builds products and is making profit. They will have Product Managers and likely some career options as you get more experience.
The difference with Product Manager vs. Project Manager I think is really a Product Manager will have to acquire or start with in-depth knowledge about the market a product operates in. In some ways a product manager might be a superset of skills including project management. There could be organizations big enough where these are different roles though. If you have knowledge/experience and interest in some domain, start there since that is helpful.
There are project mgmt classes and certifications like PMP or Scum Master. I don't think highly of orgs that require certifications on things like this, they tend to focus a little too much on strictly following a certain framework's guidelines as rules. They could be a way to get a job and some experience under your belt. I think the PMP cert is shorter if you have a college degree and it does require doing PM work as part of the cert, has different levels, etc.
Thanks for the guidance. As an alternative to PMP / Scrum certification, would it be worth looking at Product Management courses directly? Would I be making too big a leap in skill development?
I took a MS level project management class that was geared towards PMP and the instructor had run massive projects to build out factories before teaching. I don’t know what base you’re starting from but if there are courses that seem relevant, research the department/school they are under to see what people that finish those courses end up doing. See if the instructors have real world experience and if you jump into that, aim to build your network along the way. I have no idea if they do product mgmt but MIT and Stanford have some of their curriculum free online or post videos from classes. You could get a feel for the content and see if it would help, if thats available.
I think you’re underestimating your experience at a startup. Bad experiences really help solidify what not to do and the path ahead is easier to see.
Can you code or are you looking for a non-coding role?
If you can code, the path back into tech from a lost decade is pretty straightforward - practice up on coding interviews, spam enough companies with resumes to get interviews, then do well on the interviews. If you can ace a coding interview then people will overlook time in your past that you spent unemployed or working for failed companies.
If you can't code and don't want to then I'm not really sure what to advise. It depends on what sort of job you want, exactly.
I can't code, unfortunately.
My goal from the very start has been to be a self-starting product builder. I worry it's too late at this point as I don't know who'll take me under their wing at this age.
Not sure what coding has to do with product management -- unless you are planning on building an IDE or some very developer-specific tool or something.
I went thru at least one of the product mgmt courses on linkedin and i thought it was great-ish. two guys. one guy was hella funny. i figure if you can go thru that and understand the gist of what they're talking about, and can talk about how prod mgmt can or should be done, just the high-level concepts, then you're good to go -- go get a job.
product mgr. product owner. junior. product analyst. etc.
and, i thought i heard 'Prof G' give some good advice the other day -- he told some older woman who was concerned about getting a job while older -- "well, go get a job -- if you can get a job, then that's the proof, just like it is proof if you can _not_ get a job." -- i.e. don't worry about x y z -- just go get a job.
my biggest problem as a wantrepreneur is i just don't want to do product management for anybody else but myself anymore. :-)
i also think finding a mentor is a great idea. and just like-minded idea-y/imagineer-y/startup-y-type folks -- entrepreneur meetups, etc.
I wrote a book that might help you. It's free and you can get a copy here.
https://jondouglas.dev/free-book
I talk a lot about limiting beliefs and the mindset that will make you successful in teaching yourself a hard skill like coding / data analysis / product management / etc.
Good luck!
Hey hey! I've met people who match the description in your post, and over time they've rocketed to success. Coding is not as important to a product's success as people make it to be. If you think you're good at coding, the furthest you'll go is architect or principal developer. I'm not saying this to reframe or control the narrative. I'm saying this because of fact. Some people are simply inevitable. Others?
Copycats are better off learning how to invest in themselves through introspection. You know the saying that goes "Every time you point a finger at someone else, there are three pointing back in your own direction"? Because character is destiny, the best an imitator can do is desperately say things as if uttering the magic words will achieve anything.
FYI, 'if' is a conjunctive adverb, which doesn't require a preceding comma since it's not a coordinating conjunction. Improving the way you write will improve your thinking process :) As the poster says, "Hang in there, kitty!".
Sorry to hear it's been a tough decade...
Reading your post, I get the feeling that your professional potential is probably higher now in some sense that may not yet be clear.
For example maybe the previous years weren't exactly skill -development time in the building sense, but maybe they taught you to be even more of a ninja in terms of knowing what you don't want, or won't do. So your big-picture skills may have grown.
Your writing also points at a lot of other hidden strengths, probably newly-relevant strengths as well. For example you clearly have the ability to improvise. If so, a big question moving ahead is whether you are willing to embrace the convergence of somewhat orthogonal topics like "doing the chicken thing" and "documenting it so well this time that you become a subject matter expert in at least chicken runs, but likely also the processes you want to know well."
There will be lots of other questions here too, for example your journey is clearly that of an autodidact, so should it be kept more subjective and less conventional, to accommodate more of your latent passion and attention to your own drive? This option is rarely pointed out to people with such gifts.
Just some thoughts, good luck with whatever you decide to do.
I appreciate your positive framing.
I definitely do have hidden or not-so-hidden strengths, but they are all fairly abstract and rooted in emotionality. For example, I've often been told I have a strong ability to empathize, to understand the emotional journey of a UX, identify moments of friction & delight.
But I lack the structure to self-catalyze. I've tried for a year now to build something on my own and inevitably flounder due to an ignorant and scatterbrained approach to priorities, process, decision-making, etc, despite attempts to self-teach.
yw. Those two last paragraphs are an interesting contrast. They're like "I have gifts that are really obvious, others even point it out, but also I suck at this other stuff I REALLY want to do."
The rational decision here would be to focus on the first no matter what, as that's what most people do in the career world. Those careers exist and pay money today. You can't bank on skills that don't exist, so if you go and call yourself a real-world builder and try to improvise there, you can count on lots of headwinds just due to basic career logic.
However it's a big clue that the two points of view also form two very clear dichotomies: Real - Abstract & Emotion - Logic. This usually means you will need to find a point of reconciliation before you can feel less locked up. It probably feels like your hands are tied right now due to lack of execution.
This is all wrapped in a clear ability to keep your discussion focused on subjective factors. IMO you may not like the idea, but self-analysis is a likely learning path that would accomplish all the goals you have written.
I would also hesitate to share the path with others until you have made meaningful progress, as there will be a tendency to suck all the vitality out of the room, so emotive is your gift, and so likely strong your desire to be demonstrative here.
You may even inadvertently frame meet-ups with others as your test, or as a time to demonstrate to them what you've become. In fact this will probably get you the opposite outcome from what you want, in terms of influencing people. We could describe your life as WTF Land rn, and most people do not want friends or family to have very strong memories of this time in their life. ;-)
So, it may be that you insist on Being the Builder who Builds Real Things, and that's that, and you develop a bunch of interesting coping habits along the way like people in these shoes do. Or you find a more creative way that syncs with your clear strengths and integrates the "duh" perspective that outsiders have shared with you.
Regardless I think it ought to be an interesting journey!
> I eventually found my way to joining the founding team of an early stage startup where for the next 6 years I ran around like a headless chicken. Whether due to lack of education, experience, mentorship, or volition, I learned very little about how to systematically build a product and business.
I would start by reframing this experience away from something negative and into something positive, and re-examine the assumption that you learned very little.
Just because the startup was ultimately not successful does not mean that the experience was not valuable and that you didn't learn anything from it.
Often we dismiss or fail to realize our own abilities because they see obvious to us. The reality is that virtually nothing is obvious to everyone, and what might appear to be self-evident to you might be deeply insightful for someone else.
I would start by listing out all the ways in which you experienced failure during your startup experience, and for each of these, what you learned from that failure.
> I have good intuitive product and design sense, but have very very little in the way of effective skills, such as understanding and facilitating a product development process. Additionally, I have a very small network, if one at all.
You've already identified the areas in which you are lacking. Take a course on product design. Your lived experience will give you a much better understanding of the course material than someone without it. Go to events related to industries that interest you in order to expand your network. Reach out to people who are successful in the ways you want to be and ask them for advice.
Good luck!
Is money a thing for you? It this a serious hobby or do you actually need it to live?
If you want to become a PO at 40 I think you’ll have to somehow find roots for if from the experience you do have. Else do you really want to start out as a junior analyst and work your way up?
Thankfully, I've got a bit of runway to figure things out.
My ultimate goal is to be an entrepreneur by way of product building. But I'm beginning to question if I'm fundamentally not wired for it.
I think be prepared to accept that — you’ll find orders of magnitudes more joy when you find the thing which you are wired for.
This is a process though... It takes lots of experiments & self-enquiry to reach this point, particularly evaluating the experiences but I believe this is the most rewarding thing that happens in life when we understand it.
Seems like everyone wants to IPO these days, until you ask them what would happen if nobody else would know about their success and they wouldn't be allowed to communicate it.
Anyways, PM roles can be great but are also not for everyone. Best thing is to try and see, same with product building.
For self-reflection I recommend the Life Design Stanford course or Self-authoring by Jordan Peterson.