Ask HN: How to find “senior” jack of all trades jobs?
I have been in my current role for about 6 years. While I wasn't hired for it specifically, my average week has my time split between product management, managing a small team to develop those products, ux design, and front-end JS/Python development. It's really a roll where I am all over the place and I do really enjoy it. However, due to the Covid reality in the world right now I am starting to think my time here is up. How can I find another job that isn't specialized to one specific roll as I really do enjoy being a jack of all trades master of none and would like to continue to do that in my next role. I'm also fairly experienced with 16 years of "jack of all trade" type positions.
102 comments
[ 0.27 ms ] story [ 242 ms ] threadThis is why we're building https://peerwyse.com. We think finding people with good salaries from your LinkedIn network who you think of as your "skill-set peers" will identify opportunities in their industry that traditional job-title based searches can't reveal.
Inside a large company, the largest and most prestigious initiatives will be well-staffed with specialists, and a bunch of management types to coordinate them. But even if the company has a tech focus, you'll also find teams of network administrators, billing folks, supply chain people etc who are struggling to have their needs met. Typically their story is "we can't get out of our manual processes quickly enough", and they will be worried about a high manual error rate and/or scary headcount projections.
These teams don't have a product manager or UX designer because (1) they don't need 40 hours/wk (2) those folks will gravitate towards public-facing products. They don't have a deep bench of backend specialists and frontend specialists. They also struggle to get support from centralized teams, because they're a lower priority or they just don't know how to ask. This creates opportunities to unblock the team by jumping in and helping with data/analytics, deployment, testing... all the stuff you might expect to be "cut a ticket to the team which owns this" in a large company.
I'm mostly happy, but my real fear now is - what next?
Like you, in my 20 years doing this type of role (wearing a large variety of different title hats) I've never been HIRED to the role. This feels odd, given playing the role always keeps me in high demand internally to organizations.... so if its something organizations crave internally, why don't they hire for it?
When eng/prod/ux "broke up" and became separate job roles in the post-Google and post-MS world, I found it /very/ frustrating, because I'd rather straddle all of these objectives. Additionally, I find many companies fail around these seams, because its hard to pragmatically find the optimal solution in the broad eng/prod/ux tradeoff space when you have the "deep knowledge trees" spread across many heads, with the limited bandwidth that entails.
When I started taking senior eng management positions, I naturally thought I would change this, and explicitly hire some "jack of all trades" folks. I was surprised by how hard this is to do, harder even (for me) to evaluate than specialist knowledge, was distinguishing pragmatic and effective "jack of all trades" types from, well, bullshitters. This is funny, because the really effective "jack of all trades" I've observed are in many ways the farthest from BSers possible, they're usually so broadly knowledgable partly because they are so voraciously pragmatic that they end up learning a lot of different things. But from the outside, I wasn't personally successful in confidently distinguishing people in an interview context.
The problem is there's a similar appearing archetype to "jack of all trades" the "always reading never doing" person. Conversationally, they can appear similar. And I found (and find myself) that its hard to test jacks-of-all-trades because they often don't keep knowledge at their fingertips, part of their skill is fast learning. But even if they spent serious time using a technology, they still need 4 hrs of work in it to look surface competent again (I think because they're constantly swapping knowledge in and out, vs a deep knowledge person who have practiced the same patterns over and over and over).
So my limited experience as a "jack of all trader" was: 1. Yes, companies seem to get a LOT of benefit from really good people with broad skillsets. 2. But I personally don't know how to select the good ones in hiring. I suspect other people have found good ways, I'd be curious to hear about them :-)
I've been doing professional software work for 25 years. The last several years I've been working with various JS toolkits (vue/angular, some react) as well as backend stuff (mostly PHP, some Node, some Java, some other stuff), and attendant tooling and whatnot (build systems, testing systems, etc). The last 6 months, I've found myself contracting on different projects swapping between these various stacks, sometimes multiple times per week. I know I look incompetent as a JS developer to some folks who are living in that world 40+ hrs/week for years on end. Couple the various tech stacks with each team's own styles of doing things - which, really, they each seem to think any deviation from 'their' standards is heretical and indicates you're a 'lesser' or 'less experienced' developer - it wears thin after a while..
Trying to 'showcase' that 'jack of all trades' aspect in interviews rarely seems to go well, unless it's not an interview and just a word-of-mouth referral from someone who already 'gets it'.
e.g. Interviewing for a backend dev position but don't want to write any code/algos in the interview, and just talk past projects? OK, that's gonna be tougher sell, but I'm game if you think you can convince me of your strength down that road.
This makes me think about, in my case, if somebody were to offer the same interview freedom to me... As a strong senior generalist, how would I demonstrate that most definitively in 45 minutes? I haven't come up with an easy answer, so I still try to masquerade as the type of specialist-to-role expected in interviews (which I can do to some extent, the full line is "jack of all trades, master of none, but oftentimes better than the master of one") but I do think it under demonstrates the real value I bring to organizations.
I don't have an answer yet: under even friendly circumstances, how would a strong pragmatic generalist unquestionably demonstrate it?
In the smaller category of "generalist programmer" (which, like the OP is too restrictive to cover my usefulness) I have thought of games like "pick any domain from a past job of yours, and we'll work on code problems like that, even if I've never worked in that area before", i.e. suggest the true generalist nature by random sampling. But, its hokey, and it still only covers programming.
I'd love ideas, I must confess the frustration of the "useful-in-practice generalist in a world interviewing for specialists" mismatch has me staying at companies that are no longer ideal places to work longer than I think specialists do. Every time I switch jobs, I think the interviews undervalue me, and once I'm hired as a generalist-disguised-as-specialist, it takes time to migrate organizationally into the generalist role where I contribute the most value (even at small companies).
Also for jack-of-all trades looking to perform well in interviews, my advice is to engage context specific memory. If it's a Python role set up a past Python project on your computer and dig into it a little bit in the minutes before getting on the phone. Your Python mind will come back a little bit.
Same here. I started as a webmaster.
> The problem is there's a similar appearing archetype to "jack of all trades" the "always reading never doing" person.
A good metric I used is to check their Github profile. I believe a "doer" jack of all trades will have to experiment often.
But I agree that they are really really hard to find!
> But even if they spent serious time using a technology, they still need 4 hrs of work in it to look surface competent again
This is true, and even more so when you switch between very different fields. For example, I must admit that it takes a little while to go from a UX design "period" using Figma all day to a DevOps "period" to build AMI's and navigate through AWS (which is a FT job in itself!). And the more fields/subfields you practice, the more likely you are not practicing one for a while; so the time switching becomes a burden and comes with an overwhelming feeling.
On the other hand, Jack of all trades have an incredible advantage in seeing the big picture and visualize the intersection of each field at a very deep level.
For example, a marketer with engineering knowledge will think of growth hacking strategies a specialist marketer would never think of. Or a designer with engineering knowledge can design UI's that can be built efficiently.
1) Specialize in at least one thing. This will make you an expert in one thing, while still being the person everyone goes to for other things as well. This will help advance to senior developer.
2) If you have a good grasp of the logistics of how pieces of a project fit together & the coordination necessary, another clear path to a more senior role is team lead where you do PM & part-time development. If you want to go higher than that, you're looking at high level project or product management. Actual development work will be minimal, but again with a jack of all trades background you will still provide valuable insight & guidance to those performing development work. And you can always look for extra opportunities to get your hands dirty back in to coding here & there.
The OP appears to have significant experience already, and it does seem suboptimal to masquerade as a specialist in all job hunts, when that's not the real value you bring to the table.
Its leaning on the third clause of the full text of the quote: "jack of all trades, master of none, but oftentimes better than a master of one"... in other words, become a stronger specialist at one thing than most of the specialists in that area. That's great, and some of us can do it, but we're still not as strong as a specialist of our strength. It means you always interview as if you're a couple weight classes below where you actually are.
That's a practical compromise for a person starting out, but like the OP, with enough seniority, and the tremendous value that an experienced generalist provides, it feels bad to lean on that leg in all interview situations!
Another option is to find a cookie-cutter role that fits your interests. For me that means "embedded software engineer", where all of my experience is relevant. I'm definitely all-tech and no-management now though.
Yet another option is consulting/contracting/freelancing. You need a good network for that. I haven't done this. Preparing to potentially do it in a few years after I have a larger nest egg.
In my experience, job titles, levels, and even team membership are more "guidelines" than rules, and are often trailing indicators of what and how you're actually doing. I wouldn't worry about finding the perfect opening - just find a team you like and a manager who seems to get it.
Other alternatives:
- move into management
- found your own company - your jack of all trades skills will then be pressed
- you could also start a side project and put your energy into that, hopefully it will develop into your own company.
- write a book in something (edit: there's the international consultant route for this to I suppose, become a super specialist in one thing and run around talking about it)
- edit: Sales / evangelist etc
Yup. I'd add public sector work to that list (mostly because it's chronically understaffed and heavily siloed so you have to fill in a lot of roles).
BigCos tend to like specialization because of consistency/efficiency. They might have a skunkworks where you can be a jack of all trades but it's hard to get hired into those roles.
Unfortunately, working your ass off for $40k and a questionably managed pension doesn't put food on the table.
On the flip side, I work completely flexible hours. Never more than 37hours a week, and within those 37 hours I get a paid lunch break, so it’s really 34,5 hours a week. It brings flexible, I’ve sometimes had 70 hour weeks doing big transitions or elections (we do digitised voter signin, and there is a lot of preparation involved to make sure it doesn’t fuck up and that everyone knows what to do if it does). In Denmark everyone in stable jobs gets to take the first day of a child being sick off. I get three days. Every man gets 2 weeks of paid and guaranteed paternity leave, I get 13 weeks. I get two extra paid vacation days per child under 13 a year (up to 3 or 4 children, not sure about the limit). I get an extra week of paid vacation a year compared to the national standards. If I have to see a doctor or a dentist, I can do so on and count the time as working hours. And I get to work in an environment where people won’t bat an eye when you use these things, you obviously can’t abuse them without getting attention.
We have some of the lowest corruption in the world, and while our leaderships and management structure is archaic and IT is completely undervalued considering every one of our employees uses it at least 1 hour a day and about two thousand of them spend their entire day working with computers, it’s not terrible.
Like I said, the pay is lower than the private sector, but IT is paid well, so even though I could make more money outside the public sector, I still make more money a month than my mother who’s been a anaesthetic nurse for 39 years. The only professions who rank in more money than me outside of tech is things like doctors, lawyers and middlemanagers. So I think it’s fair enough. Obviously my boss has the same benefits as me and he makes around tripple of what I do, so it’s still better to be a manager in the public sector than an IT grunt.
Our private sector is still relatively booming for developers, so there is always jobs openings. People tend to shop around more in the private sector though.
On the other hand my fulltime contract pr the union agreement in the private sector is 36 hours (and 5 child sick days).
I always find these posts from Americans amusing. “Yeah right, nice vision of some ideal world there, but it can’t possibly exist.”
Get a passport, kids.
and austria :)
sure ... you don't get too much money in the public sector.
but payment is pretty ok, stress is on a considerably lower level than in the private sector, and if you want you are able to work there until you retire ... you remeber: job-safety ... the thing a lot of young people are constantly whining about.
There can be a lot of bureaucracy around hiring leading to quite well defined roles. You're right about understaffing and if you end up in a good sub organisation there'll be a lot of work to do and room to branch out. But you're unlikely to get hired as a jack of all trades. Startups are far more likely to hire useful people who can do a lot of different things. Public sector you'll be hired to do a specific thing but then might be able to pick up lots of random things if you have the right rep or people around you.
It gives you a great taste of startup life w/o a lot of the extreme downsides. Sure, you don't have all the upside, but one step at a time.
Lack of a steady paycheck is pretty crushing for most people.
evangelist? elaborate please?
I'm not sure how to find them other than to ask in your community.
Ones that I know of (in Colorado, my stomping ground):
* https://www.culturefoundry.com/
* https://crowandraven.com/
* https://devetry.com/
Not sure where you are located, but I'd search for "web development <city>" and see what pops up as a starting point.
I recently moved into devrel for a smaller company and can vouch for the fact that it is a great position if you are a jack of all trades. In the last week or so I have:
* worked on ad landing pages
* written code for an example app
* recorded and edited a video
* filed a couple of bugs against the product
* responded to support requests
* written a blog post
* stood up cloud infrastructure to help me document a new feature
As Robert A Heinlein wrote: “Specialization is for insects.”
If you do stay in management, get your priorities straight. You do need to be the jack of many trades but these are probably not the trades you are thinking of.
Your first and foremost priority is building the right team. Hiring right people, giving autonomy and sense of purpose to the team members. You want people that are smart but even more importantly you want people that get things done with little or no supervision.
Having said that your second most important priority is to get people unstuck. Be it your gravitas in organization, making the right introduction, or sharing a critical piece of knowledge - check in with your team regularly and actively ask if there are stumbling blocks or blockers. Many people are good in asking for help but there are many for whom it is hard.
I could go on but the point is that the trades you want to master in management are more like: communication, courage to delegate, empathy, accountability, being able to make decisions on imperfect information and deal with whatever consequences come up, etc.
EDIT: if you are leaning more towards individual contributor role, you will probably either find startups more interesting OR - if you looking for seniority - find an organization that has parallel ladders for management and individual contributors. Those companies will have positions that are worded “staff engineer” or “principal engineer” and tend to be on a larger side.
Take health insurance: I'd imagine employers are buying plans offering per-employee costs lower than if each employee were paying for their own insurance. Economies of scale, bargaining power (at least when it comes to larger firms), etc.
Perhaps at some firms the processing costs really do outweigh the savings, but I would expect this to be the exception rather than the rule.
I could be wrong -- maybe someone with experience could shed some light here.
There were companies that offered full, proper health insurance, but I had my own so the value was close to nil, and the salaries were 25% lower than the smaller companies offered.
Benefits tend to be mostly flat across employees to make use of economics of scale. I'd love something like a company car, and would happily take a salary cut because they're liabilities and it's a win-win where taxes are involved. But if a company won't offer a car to everyone, it's not going to happen. I got free parking as a benefit once but only used it a quarter of the month because it was cheaper to Uber to work. I know they were paying for the parking every month and I'd rather take the cash, but I wouldn't turn down an extra $30 of savings even though it cost them about $100.
In my opinion, we should do whatever maximizes product-market fit.
For the first type of role, you're essentially hired help to solve non-technical problems in broken well-capitalised businesses, whereas in the second you're hired individually for your own skills. The second type are normally much more flexible with respect to remote and lack of travelling.
Consulting.
if you're looking for the rare individual who transcends categorization, you don't do it through job ads or an HR department. it's hard enough to find a person who can do one role well.
so, if you're a jack of all trades, look for a job fulfilling one of your many possible roles, in a place where you will be able to fulfill the others as well. it sounds like that's exactly how you got the job you have.
I don't have the lofty "Sr" in my title but I have a special designation as the "edge case SME" in the list of experts. I also do big crisis management which is pretty fun. Not a dev, so take it as you will.
https://jtauber.com/journeyman_of_some/ is a particularly eloquent way of putting it.