Ask HN: Career progression vs. meaningful/appealing products?

94 points by yiiiizzz ↗ HN
I'm in an interesting situation and would like to know about what others who have faced the same situation have done in the past.

I've been in the market for a new job since spring. At the beginning, I was only focused on products I really liked to (in summary, what a futurist engineer geek would like to: AI, blockchain, security, etc). I had several interviews, but no one struck a deal, either because they decided to move on with other candidates or because I decided to drop off.

Fast forward to mid September, I decided to start applying to positions that suit my role and/or career progression, but in less appealing companies. And I have been very successful. The minimum offer I have received doubles my current salary.

So, I'm in this situation in which I have offers which look positive from a financial and career progression point of view, but in boring products which not interest me at all and which have no upside at all.

Have you ever been in that position? What did you do?

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If you progress your career then you'll have more involvement and will be able to have more impact when you eventually move to a company where the product really interests you.
Take the best offer from the least demanding company.

Use 1-2 years there to upskill in area you care about. Effectively work minimum needed to get a good review from them. Then apply again to area you want to work in, with new salary as your standard.

Will take patience and perseverance.

I personally spent 10 years working for banks, which I’m sure few of us are passionate about, but I did grow to appreciate things like the scale, the business criticality, and the opportunity to engineer properly in that environment.

Sure, working for a Crypto exchange might be more fun and look cooler, but if they have 10 customers and you are constantly under pressure to hack stuff into production for an egomaniac CEO, it is not a great environment to grow and work in.

So personally I wouldn’t be so quick to write off the boring or unsexy opportunities. Especially early in your career when you need to learn how to do things properly.

It's hard to answer as it's very personal and there are other elements to take into account.

My first advice would be that if you can double your salary, do it. We don't know what tomorrow will be made of.

Also you don't mention work-life balance and quality of relationships with colleagues which to me is more important than interest in the product.

That being said, you can also keep interviewing and try to find a job which checks all the boxes.

1. Why are you looking (assuming you are still employed)? 2. Why did you get no offers in your 'dream' companies? If you answer those two questions honestly, you will have your answer to this question.
I have been in a similar position multiple times.

And I regret the times where I let money decide. It usually felt like "Ok, I'll just do this for a few years, make a boatload of money and then move on".

In retrospect it feels like I wasted those years. Life is so much bigger than a bank account. Time is priceless.

>Time is priceless.

I wholeheartedly agree, but working at a company is selling time no matter how interesting the technology might be. It's not the same as working on personal projects; there will always be unpleasant aspects to it, certainly after more time passes (I've been through more M&A than I care to think about).

If the goal is to stop selling your time, then double the salary would achieve that goal twice as fast, assuming the job is at least tolerable. Never work for a shit hole where you dread coming in, but money is a means to an end. Money is freedom.

Lots of different things to consider but would also factor in opportunity to learn: if you take that offer which doubles your salary, do you have opportunities for growth, either in leadership or from a technical stand point?

At one point, I personally took a short-term pay cut in order to join AWS, an organization I once really wanted to work with. Ultimately, the decision paid off, both financially and career wise; hard to put a price on working with great people, building great products, and stretching oneself.

Don't get me wrong, money is important and making that leap of 2x might be the right move for you, right now. That choice will also be advantageous when it comes to future negotiations. But if you are early on in your career, you might want to find a position that allows you to master your craft.

There is a spectrum and thresholds we all have but in general: Work for money and find meaning in hobbies/side projects/etc. This doesn't mean money above all else, just that looking for both is unlikely to bear fruit.
All things equal, pick the areas with growth. Google, Meta, Amazon all have natural monopolies in growing markets where your individual performance doesn't matter that much. This is a safe play w good short term upside. AI, blockchain, security, etc are growing areas but you need to make an initial investment and maybe a lateral or down move to retool yourself and reorient your work network. This is the risky play with a lot more potential upside.

Life is short though, once your base needs are met, figure out what you want to work on and spend more time on whatever that is.

When I was in my late teens, I realized that videogame development was harder, underpaid and didn't focus on the aspects I liked about software development (long term vision of the software, software design).

I dropped that and never looked back. My career is very happy, enjoyable, well paid.

As usual there are exceptions in every context, but what you seem to be doing is similar, I believe that focusing on the product is wrong.

Working on a type of product has little connection to the type of work that is going to be performed, which could be boring or very different from what expected.

My thought has always been: focus on the type of work you want to do, the rest comes naturally (potentially even passion for a new product!)

Pick the position that will equip you with the experience you need (or have growth opportunities for that experience) to get the gigs you want. This means optimize both for the work itself and also the team/people you'll be working with.

The money will follow. Maybe not in the same quantity, but money has a diminishing ROI after a certain point versus working on things you want to work with.

One thing I'd recommend is trying, to the extent you're able, to broaden which layers or dimensions you look to in determining whether something is interesting.

Obviously, there will be some products that viscerally excite you and others that don't, but let me elaborate: perhaps a company is working on a tool to help construction workers orchestrate cleanups at their work sites...or the company is working on a platform to help automate property management...whatever.

These may not seem as exciting, on the surface, as other products you may have seen out there, but it could be that digging into them further there are elements which will pique your interest. For example, perhaps the systems that need to be built in support of these products are particularly complex or they present particular scaling challenges, etc.

The underlying product may not be super interesting to you, but it could be that the engineering work involved in them is actually more interesting than some other product that feels more exciting to you. Or perhaps the business or operations side of these companies is very interesting and well-executed and there are things to learn on that front.

I'm not expressing this very well, but my main point is that there can be a divergence between products that are interesting and work that is interesting - often times the less exciting product presents more interesting/challenging work. To see that, you need to take into account the entire equation: the biggest challenges the company is facing, the long-term strategy, how sharp the business/ops side of the company is, etc.

Keep an open mind; things that, at first glance, don't seem interesting may turn out to involve _very_ interesting/rewarding work.

Great point. This is probably an excellent thing for you to look for as you are interviewing with companies (and yes, you are also interviewing them). Ask your future peers and colleagues what they find fascinating about their work, and how they find meaning in what they do. You may be surprised by what you learn.
I ran into this with a web app to automate unenployment insurance claim processing.

It sounds so boring but it turns out that every state has their own process (that they change without notifying you) and they use different pieces of data to identify workers and companies. Also everything was still paper-based so we got a scanned image and OCR text.

This was 10 years ago and we were doing fairly large scale NLP in PHP, matching millions of documents to claimants and companies and doing some amount of fraud detection.

It's still among the most interesting projects I've worked on.

Awesome example: most work can be interesting, when getting into the nuances.

However, all works and companies do not incentivize doing whatever work interestingly.

A few questions I use for potential employers:

- What's one idea that you came up with and implemented, in order to make your company better? What was that process like? (Read: find out how much the company supports bottom-up innovation)

- What's the process for getting adopting a new dev tool or standing up a new server at your company? (Read: differentiate between command/approval-driven companies and need/self-serve companies)

- All the basic boring stuff: What's your CVS system? Is code visible across the organization? What's your knowledge system? Are documents searchable and visible across the organization? What's your CICD system? (Read: make sure you aren't walking into a dumpster fire where basic hygeniene has been neglected)

That work wouldn't be related to SIDES would it? If so hats off to you and yours for making such a resilient piece of software. I've been working with my states unemployment offices since the pandemic and just the interoffice differences have been causing issues with automation. I don't even want to think about making something work across state lines.
This was right before/overlapping with the beginning of UI SIDES (now there's a term I haven't thought of in a while)!

For some forms the system actually put all the information from various sources on a digital recreation of the paper form we received and faxed it off. We only did that for the most common forms though.

I learned so much about database schemas and performance, since as I'm sure you've seen you often receive claims just before (or sometimes after) the response was due and if they're a minute late the claim gets paid by default and if the claim is due at 4:30 the HR person will casually log in at 4:28 to upload several documents and fill out a lengthy form.

That's a write up I would like to read.
you just described why I started to apply to different companies back in September. Not thinking about the product but about the underlying technology.
I couldn't agree more with this. I'm currently working in a company that builds what could be considered a "boring" product. It's enterprise and thought for big companies. It doesn't have AI, blockchain or anything trendy. However, I love the work we are doing. Instead of using a lot of open-source tools, we develop our own. Even though I'm against this, it allowed me to learn a lot and got me some great experiences and learnings.

One piece of advice I can give is to try asking during interviews what are the most interesting projects the interviewers did and why. It will give you a rough idea about what they are doing and if you would enjoy working there.

Also, I don't think there is any correlation between career progression and interesting projects. You can grow working on interesting or boring projects. The important thing is what you learned and what you achieved.

One of the ways I try to think about is asking myself if I feel like my job is bullshit.

I currently work for an extremely large multi-national company on a really mundane sounding use case with a pretty vanilla Data stack. What we build has direct impact to our customers. That means that we can map what we are building to our customer experience, which means we need to understand the impact of what we make and use that to balance the various Engineering tradeoffs. I don't feel like I'm doing bullshit work.

I had another job cool sounding job with all sorts of buzzwords, including "AI." When I told people the use cases we were looking at and who I reported to, everybody thought I was doing some amazing stuff. Literally 90% of my work was chasing down BS ideas from VPs who seemed to want to find more complex ways of justifying their decisions. That job was the coolest sounding job I had and was 100% bullshit because nothing I was doing had any real impact on anything.

Bullshit work is not interesting, no matter how cool sounding it is.

That's not really much of a position. You got offers from some that solve one problem, and didn't from others that solve a different problem. I'm basically here as well, and I know that software development can be soul-destroying, so you need to get what you can out of it and try to find a place that satisfies both areas if you can. More money, past a certain point, doesn't necessarily bring more life value unless you're a consoomer. But you do want to probably be around that point anyway
>I have offers which look positive from a financial and career progression point of view, but in boring products which not interest me at all and which have no upside at all.

>Have you ever been in that position? What did you do?

Yes, I chose the "boring" job that with fabulous compensation. (It was proprietary accounting systems and it paid better than FAANG.) I spent 10+ years at it and made a lot of money but it's also one of my biggest regrets. Consider 2 groups:

- (group A) prioritize money more than the particular job. They can compartmentalize the boring job and do the fun stuff on the weekend.

- (group B) people prioritize interesting work more than the money. As long as the job offers a decent salary, that's good enough.

I thought I was in group A but it turns out I was actually in group B.

However... the big caveat with my anecdote... The problem with answering your question is that the right choice depends on _your_ personality.

I'd be wary of taking your conclusions at face value. You can obviously reason differently after accumulating a lot of wealth over the 10+ years.

What-ifs are an impossible dilemma, and I wouldn't stress on what type of person I am: I know I change, so I am a different person at different points in time (and in large part, due to circumstances).

It sounds like you could comfortably take a couple years off to do whatever you regretted not doing earlier, and by the end of it, you should have no regrets. If you do, however, plan your days like it's work (I've taken multi-year leave, and I behaved as if I have all the time in the world, and I didn't really achieve much of what I wanted to ;-).

Experience matters.

If you want to increase your ability to get the jobs you want, working at a well-known firm for a few years is the most straightforward way to boost your resume. People with a few years of Google or Microsoft on their resume often move to the front of the line for hiring.

Take one of the well-paying jobs. Do well, leave a good impression, and network well among the people you meet. Re-evaluate in a few years. Who knows, you may discover you like these companies a lot more than you think. If not, your resume will be well-prepped for the next move.

I don't think that having a "career" always means hopping jobs every 2 years in favor of a "more interesting" one. My personal experience is a bit different.

The most important thing about a new job in my opinion is not the technology you work with or the company you work for, but the PEOPLE, you work with / for...

Are they experienced? Motivated? Professional? How nerdy are they? How arrogant? Does the team work together or is it a toxic relationship? Are things like Coding Dojos, Pair Programming, Code Reviews, etc. well established? Is your potential boss fine with this or not?

The problem often is getting to know the team before you actually starting the job. I always ask for a "training day" to see, how the team is working on daily tasks...

Choosing the right "Team" and building trust over YEARS and having a work-life-balance is the most important step to build deep knowledge and still have fun, regardless in what technology. Much more important for "happiness" than money or hype hunting. If you are passionate for what you do, you will build confidence and learn much more than on the other path.

Just my 2 cents.

If you were to get hit by a bus after a few years, which path would give you more satisfaction having spent the last few years of your life pursuing?

I know that is a dark way to look at things, but it is also quite pragmatic. People spend so much of their careers building up wealth, skills, and power, hoping for a future day when it all will give them everything they wanted. But often you can build the life you want earlier in life by looking at your options holistically, trying to balance satisfying and meaningful work that you could be proud of in the short term... while also making enough money and building skills to carry you forward if you are lucky enough to get a long-term.

I have always tried to strike that balance - I don't work for below market rate just to get meaningful work, but neither do I seek out the highest paycheck. I look for work that adds some value to the world.

"At either end of the social spectrum, there lies a leisure class.”

—Yosemite golden-age climber Eric Jay Beck

There are many ways to happiness, sometimes you can just go for it directly, sometimes you build some security on your way there.

"Most men, even in this comparatively free country, through mere ignorance and mistake, are so occupied with the factitious cares and superfluously coarse labors of life that its finer fruits cannot be plucked by them. Their fingers, from excessive toil, are too clumsy and tremble too much for that. Actually, the laboring man has not leisure for a true integrity day by day; he cannot afford to sustain the manliest relations to men; his labor would be depreciated in the market. He has no time to be anything but a machine. How can he remember well his ignorance -- which his growth requires -- who has so often to use his knowledge?"

https://www.owleyes.org/text/walden/read/economy#root-14

>If you were to get hit by a bus after a few years, which path would give you more satisfaction having spent the last few years of your life pursuing?

One of the reasons I have a aversion to this question is that it's usually followed by "follow your passion" or something equally trite.

However, I do think it's useful when you are in a situation you hate and you wonder if it's worth leaving. Yes, definitely leave that.

If you have an "okay" job that lets you maximize your mental health and time for other things (e.g. family), maybe you'll feel like you made the right career tradeoff when that bus hits you.

Especially the family part. That is the source of great personal growth, development of virtues (as we learn from each other and serve, and seek one another's comfort and well-being), and of long-term happiness and support in life.

It is not pleasant for me to imagine life w/o my family. We are certainly not perfect, but we try to be a benefit to each other, and we are. Our parents (who are now great-grandparents) have set examples of long-term unselfishness, which helps. Others can do that to start such trends and traditions of their own. So worthwhile.

I agree much. Having a purpose in life can guide decisions. I believe life extends far beyond mortality, and what we become (virtues acquired, like honesty & kindness, learning) and our service to others are important. Edit: and earning an honest living to serve others and support a family is also honorable and good.

There were some other HN discussions where I commented in more detail, and the containing discussions also have interesting comments. (And maybe I'm a cataloguing personality, and like these ideas...):

https://news.ycombinator.com/item?id=22129921

https://news.ycombinator.com/item?id=23452651

https://news.ycombinator.com/item?id=28867645

https://news.ycombinator.com/item?id=23553508 (this one has a bunch of HN links to discussions on internal motivation)

https://news.ycombinator.com/item?id=19708786

Where you are in your career also matters. For my last job, I took a pay cut to work at an interesting startup, and of course went into it knowing it might not last.

I'm more interested in stability now. On my last job hunt i was avoiding some more interesting work in favor of stability. I was in my late 30s at the time and just didnt want to go through all the start up problems I've experienced in the past.

That all said, I'm on a small team now working on an ecommerce site. It seems like a boring job, but I've been surprised at how much I've been able to use "interesting" tech to solve problems. You actually dont know when that boring job might be exactly what you want.

I have two kids so I chose the career and money over the fun product. I left my fun job for double the salary, it was a no brainer. I'll get another fun job in a few years.
Don’t underestimate what doubling your salary can do for you. Unless you already have all the financial resources you will ever need, earning that extra money, especially while you are younger can change the course of how quickly you reach financial independence. Once your financial house is strong, you can make decisions for the rest of your life that optimize for things other than money.

I chose to optimize for higher salary. I plan to get back into the nonprofit and social good world later in my career.

To paraphrase one of my favorite quotes on the matter, "Whoever said that money doesn't bring happiness has clearly never tried being poor."
There's a corollary from some founder (one of the Instagram guys?):

There's really only 3 kinds of money.

There's "I don't have to worry if I'll make rent or be able to buy groceries this month" money.

There's "I don't have to think about prices or when I go out to dinner" money.

And then there's "I can take unpaid time off whenever I feel like it, and travel to where I feel like" money.

Past that, everything is just bigger numbers.

It always resonated with me, because (a) it phrased money (which doesn't really matter directly) in terms of outcomes (which do matter directly), (b) it coalesced things down into a few, very different outcome buckets, & (c) it made the observation that in terms of life outcomes, there's definitely a ceiling: unless you're looking for ways to blow money, there's a cap on how much you can reasonably spend.

Bill Gates' description of that ceiling: "I can understand wanting to have millions of dollars, there’s a certain freedom, meaningful freedom, that comes with that. But once you get much beyond that, I have to tell you, it’s the same hamburger."
Maybe hamburgers are not the thing you should be spending your money on.

There are all kinds of projects that are potentially useful but not necessarily profitable. Having more millions of dollars means you could do more of them.

This is essentially what very wealthy people do with their money. They purchase changes in the world around them and so shape the world to more closely fit their own ideals.
I see it a lot like obesity. Too little is very bad. Too much is also bad. But there's nothing to flag when you have too much.

You see people here complaining that they can't go from $500k to $600k and everyone says that they're being greedy. But the dissatisfaction is a lot stronger at that range, and it only goes up when people become millionaires.

I think it's quite important to check that you're eating because you're hungry and not out of habit/greed/pride.

Seems to me that this is an effect of selection. Why are people not satisfied with having million dollars? Because the personality type who could become satisfied with having million dollars, would probably also be satisfied with having half million dollars, so they are unlikely to ever have the million dollars in the first place.

People who want "exactly one million, not less, not more" are less frequent in population than people for whom no amount of money is ever enough.

> Once your financial house is strong, you can make decisions for the rest of your life that optimize for things other than money.

Even if you are not a long-term thinker, just doubling your pay for a year is almost like being able to skip work for 9 months after.

High paying jobs come with other externalities (managers who are beyond caring for anything other than their cars's model years, deadlines which are about some VP's travel schedule etc), which suck while it is happening, but having the ability to just step away from it for a 3-6 month period afterwards makes you feel less trapped in that.

The pain is real, but feeling less trapped can alleviate the suffering.

That's not to say that you should rush into a burnout factory, but getting paid more has immediate consequences to your time-value at a young age - I took a sabbatical at 28 years old, which was triggered by personal issues, but the fact that I could stop work & not worry about rent for 3 months was a big factor in actually doing it.

Is this a common pattern, work a big tech job for a year or two, take a big break, rinse and repeat?

I'm about to take a big break to recover from burnout, and while I don't expect to have trouble getting back into the market next year, I'm not sure it's something I could do repeatedly without my resume looking suspicious.

I took three months off between jobs recently which is the longest I've done since graduation. It's expensive but worth it.
I am currently on a (hopefully) three-month "vacation" between jobs, and the only thing I regret is that it cannot go on forever.
there's a lot of bullshit in AI, and blockchain is almost 100% bullshit. Much of the engineer-porn industry is just marketing hype, so if you set out to get a job based on marketing hype I'm afraid you might be disappointed.

You could try to find a product that interests you intrinsically rather than based on marketing? If you have passions, it's rarely a bad idea to pursue them unless the industry exploits said passion (ie, games industry). Failing that, money's always nice.

Commit to building up significant reserves, then pursue passion. Your compensation rate increases will likely ceiling out at some point, that's when you should consider jumping back out. If you can stand it that long, try to enjoy the ride too so it's not all about the money.
I had a conversation with a friend of mine online last week. We got onto the subject of what I do for work. I told him I'm a software developer for a customer relationship management platform that's focused on real estate. He said "wow, not gonna lie, that sounds booooooring! I'd hate doing that."

Funnily enough, my current job has been one of my favorites. There are always creative and interesting problems to solve. The feedback from my team and from the customers is also rewarding.

I certainly have some itches that I need to scratch in terms of personal projects, but generally, I'm satisfied with just how involved and exciting my "boring" job is.

Don't get discouraged if you're not seeing what you want right away. Consider cutting your teeth with some not-so-appealing companies. It may turn out that it's not so boring to you. And also, you'll get some additional experience for when those jobs turn up later.