Ask HN: FOMO by working in startups only vs. Big companies | Hacker News Reader

Ask HN: FOMO by working in startups only vs. Big companies

77 pointsNalNezumi90 comments

Hi HN folks, I can't think of a better place to ask this.

So I'm not a software engineer but robotics, and my masters degree was more of an "jack of all trades, master of none" in Robotics (but more towards software side of it)

I've now worked for about 3-4 years, so still a junior, but mostly at startups (and in my 3rd one).

Hitting my 30s last year and recently talking to a person slightly younger than me with similar background I got the sense of FOMO. this person had a similar degree and first job out of college at an (now failed) startup, but just recently landed a SDE job at Amazon.

As I haven't really worked at big companies, I've always had this nascent feeling that I never really learned "the right way" to do things. I often feel like a "patchwork engineer", learning how things work only sufficiently to make things work in a smaller scale without understanding important big project/organization principles. (or maintaining stuff)

How much of this is valid, and how much is just the misconception "the grass is greener" at big companies? Is it valuable to try to apply to big companies to get a good foundation in "the right way" to do things? I feel like I've also cornered myself with my resume / experience by only working at startups, and might not even be a lucrative candidate for larger organizations. (30s crisis not withstanding)

Any insight is much appreciated!

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I spent the first 17 years of my career at startups and am going on year 7 at big companies. I really think people should experience both. Startups offer the chance to actually experience and solve many of the same problems faced by big companies. This provides invaluable experience in understanding these problems from the ground up and the benefit of learning from doing, even if not building the optimal solution. At a startup, it's often possible to have a larger scope, giving a good big picture view of how everything works from "servers" to data to services to the front-end. You might even get a direct connect to customers and have to deal with org-level problems. Compensation is likely to be lower, but maybe comes with a lottery ticket.

When it comes to big companies, you'll have to deal with many of the same problems, but at a much larger scale and with many more stakeholders involved. Your big picture startup experience can help here (similarly, your big co experience can help you scale startups). Big companies can pay more and offer better benefits. At senior level especially, that pay difference can be significant.

Finally, regarding "the right way" to do things. At the few big companies I've been at, nothing is perfect and systems are so large that they've reached a level of complexity where few people have a solid end to end understanding of things. Rather than learning about how to build and scale systems, many people end up gaining very detailed knowledge about one particular aspect of such large systems.

I'm going on year 6 of my software development career. I marvel at people doing this for 20+ years, and hope I can be that person some day. Thanks for the insight.

> many people end up gaining very detailed knowledge about one particular aspect of such large systems

Very, very true, except that most of these people also have the experience of having had to build and debug everything end to end in past lives and are therefore good at all of it. They may have ended up in a “depth” position due to focusing on one problem at scale, but the good ones could be thrown at any mysterious problem that isn’t part of their area of expertise and still kill it. This, OP, is where your startup jack of all trades skills shine. I highly recommend trying out the giant cloud experience and becoming one of those subject matter experts for a few years. You can always take that gained knowledge about “how the big kids do it” and apply it back in startup land, and you’ll be extra valuable then. I went from a career in desktop/embedded software to piddling startups to a big cloud and I’m starting to tire of the cloud pressure but feel like I’m going to be 10 times more effective at the next startup I join because of it. Beware, though: it’s hard to say goodbye to the money hose.

This isn't really a fight between corp and startups. I have seen the smallest startups more organized than the biggest corps. It's always about the people.

Personally, I believe starting at a bigger company has many benefits, even though I would now never join one. Considering you never worked there, I don't think a short experience wouldn't be enlightening. Just to learn the rights and wrongs. Be vary about the teams you're joining, though. Sounds to me like you need to figure out first what kind of dynamic you're looking for.

> It's always about the people.

This must be highlighted.

Pick a job based on people that can catapult you to the next levels.

This! I would add, pick challenging projects. Interviewing and hiring is a two-way street. If the project is not one you deem to be technically challenging enough, then hold out for the one that is. Being a part of a competent team raises your skill level.

I'll go against the grain and say that working in startups has been hugely overrated. Each time I worked way harder for less money, and dealing directly with the owner/ceo makes everything so much more complicated.

At a bigger company, sure it can be a bureaucratic mess - but I have been much personally happier every time. I get more resources, better pay, and much better work/life balance.

I didn't realize how unhappy I was working at startups until I took a corporate job again and my wife made me promise not to do another startup until the kids are grown up.

That last sentence speaks volumes - it all depends on your personality and situation. Currently I have no appetite for the startup risk and no time/desire to work myself to death on a daily basis just to see a startup succeed (or more often, fail). Work-life balance is of far more importance to me right now than anything else, including compensation (especially when broken down to an hourly wage).

> I'll go against the grain and say that working in startups has been hugely overrated.

I don't think that's against the grain, and completely agree with the overrated part. The most surefire way for someone to become financially independent is to work in big tech. The money and job security is unmatched.

I've seen it said before that entrepreneurs don't start companies because they want to, but because they have to. Either they can't get those high paying jobs at a big corp or just can't deal with the BS. I found found this to be mostly true IME.

If someone can be a good corporate worker at any of the bigs techs, they should absolutely take that job over pretty much every other option.

I'll also add this - I've found that startups that have founders with industry experience are light years ahead of the rest.

I've worked at startups where they brag about not being a big company despite no one there even having ever worked at a big company. In hindsight, it should have been a big red flag.

Odd take. I guess if you're shitty at picking startups. I know so many people who have made multiple 7 figures across secondary sales in various Series A-B companies.

A VP at a fast growing SaaS company has millions in equity. Their comparable L-8 type position at BigCo won't give nearly the same upside.

It's easier to make mid-high six figures at BigCo. It's easier to make a few million at startups. Frankly, the most talented people I know (outside of in engineering) always inevitably leave BigCo for a startup.

BigCo is a far better place for more mediocre performers.

In the context of engineering:

> Odd take. I guess if you're shitty at picking startups. I know so many people who have made multiple 7 figures across secondary sales in various Series A-B companies.

Sounds like those people are the most successful VCs ever and should consider a career switch with their ability to pick winners.

> A VP at a fast growing SaaS company has millions in equity. Their comparable L-8 type position at BigCo won't give nearly the same upside.

A VP at a fast growing SaaS company has millions in fake money. Their comparable L8 type position at Big Tech has ~700k-1 million yearly compensation in real money.

> It's easier to make mid-high six figures at BigCo. It's easier to make a few million at startups. Frankly, the most talented people I know (outside of in engineering) always inevitably leave BigCo for a startup.

Citation required. Who are these people? What were their exits? How many times did it take? Stories from a friend of a friend do not make compelling data.

> BigCo is a far better place for more mediocre performers.

The pool of available jobs at all start-ups dwarf what's available at Big Tech. It's very hard to argue that there's more mediocre people at Big Tech than start-ups.

Who said anything about exits? People are getting rich with ESOP and secondary sales. You seem to be ignoring an entire industry of early liquidation.

I'll reiterate: top performers get rich at startups. Mediocre performers get moderately wealthy at BigCo.

Any form of exit for employees, including secondary sales. Please provide data for your claim. Reiterating things don't make them anymore true.

You didn't provide any data, why would I?

I've been in several startups with really good product/market fit, really good teams/people, and good customers that still didn't make it. (Sometimes it has nothing to do with you, but just luck and the external world, e.g. 9/11 and the 2008/2009 crash.

Yes, it's possible to make millions in startups. Most don't. I've made a bit, and lost a lot. Over the entire span I've done startups, I'd probably have made more money in a solid, boring, big corp job (working for a year or two for near nothing lowers that average quite a bit), but I have no regrets, and I'd choose the startups again in a heartbeat, since they let me love my work in ways a big corp NEVER can. This rubs off on the entire team, which in a well-run startup, has a drive and cohesiveness that is nearly impossible to create in a big corp.

I hope to make big money in a startup (I'm working on another right now that needs a good all-around developer, since I've graduated my previous one to CTO at another company), but money is NOT the reason to do them. They're just way more fun and rewarding in the ways that matter. (Besides, I still own 88% of one dead company, 25% of another, and 40% of a third. Remember, equity is worth NOTHING until you liquidate it.

Money is fun but won't make you happy - I had a Ferrari for 25 years, but I'm quite happy with the much cheaper, but even speedier 15 year-old sports car I drive now, and to be fair, it's more reliable. (And doesn't track me everywhere like new cars do...)

Wow curious what sports car you have now as a former Ferrari owner?

What Ferrari model if you don’t mind me asking? Why did you let go of it?

Thoughts on Tesla’s instant torque? Would you consider electric for speed in your next sports car when the industry sunsets internal combustion engines?

There are many sizes of "startups" too – many Series C and above you'll probably never have to interact with the CEO directly, WLB improves too, but with lower equity and upside

My rule of thumb: if it's big enough to have a dedicated HR person, it's not "really" a startup. Or it's not going to feel like one.

The best size IMHO is ~100-1000 employees. Big enough that you have resources at your disposal, but small enough that you can just pick up a problem and start working it.

Absolutely. These companies aren't "startups" since they've started up a long while ago by that point.

> I didn't realize how unhappy I was working at startups until I took a corporate job again and my wife made me promise not to do another startup until the kids are grown up.

Same... but in our case the kids haven't come yet. I can't believe how difficult some weeks were for me before landing my current corporate job. My wife says that I seem a lot happier.

I did that in the first few startups, but it's not necessary, and is a sign of a poorly run startup. Good startups may occasionally need that frantic burst of "get it done", but mostly, just have a "work hard, play hard" mentality. The other path always leads to burnout, and nothing is more deadly to a startup's prospects of success than a burned-out, demotivated team.

If my teams have to work their asses off to get a demo or funding milestone done, I always make sure they get more than that back as time off to decompress and spend time with family. I'm also usually very flexible on hours - as long as they get the job done, I'm OK with almost any working hours they want. This is another benefit of startups - they have the flexibility to do things like that that you can't really pull off in a big co.

I've worked at small companies for 10 years, large companies for 5... and IMO you're not missing anything. After switching back to a small company it's a big relief, much of the big company "experience" is learning to deal with tons of bullshit. Small companies have their own problems to deal with, but to me they feel like actual problems... a lot of big company stuff is kind of corporate theatrics. Maybe it's necessary at scale, but it isn't fun.

this 100%

Big $CORP employee here. This is a pretty solid take in the parent comment. Big companies offer good pay and advancement opportunities. But, that does come with a heavy dose of corporate theatrics and organizational bullshit. At small companies, on the other hand, your options to advance may be more limited, and if you don't like the job you're in, you can't always jump to a different part of the company the way you could at a big $CORP. Like anything else, it's a tradeoff.

My advice to OP would be to simply try it out. If you see a job at a big company that interests you, go for it. You'll quickly see whether you like working for a big company or not. I never thought I'd enjoy working for a large company, but I gave it a try and I like it very much, corporate BS notwithstanding.

I'm currently working at a growth-stage company, and I wonder if its the worst of the two worlds.

We used to get things done quickly, and now we have all these bureaucratic layers inserted. But they are also immature in that folks are often thinking in the old world "we must pivot" mindset, which we just can't do given how things don't move quickly anymore.

I've gone through this at multiple jobs too. It's hard. You want the company to succeed (especially if you have a stake) but the work itself becomes less enjoyable. I very much understand why some companies choose to stay small even if it means they're limiting their potential.

> much of the big company "experience" is learning to deal with tons of bullshit.

This has been my experience as well.

* Startups ask you to work on a huge scope of things, but often give you ownership over those things. Politics are minimal and you kind of just do things in the best way you see fit.

* Enterprises ask you to work on a narrow scope, but you have to spend a bunch of time coordinating with a massive amount of other people.

I disagree with the people who say you're not missing anything working at large companies. Of course it depends on which, but there's great learning opportunities supporting a product used by millions (hundreds of millions).

It's a shock to go from this edge case will most likely never happen because we have at most 5 request per second to this edge case is happening every minute because we have 5000 requests per second. Your approach to monitoring, deploying, and writing software changes.

And great experience to be gained by working with 100s/1000s of diverse team members across the world.

You’re not working with 100s you still working with same number of people (under 10) who just shuffle out due to constant reorgs, transfers, etc

Entirely depends on your org and your role. I work closely with 20-30 people, regularly with 50, and less frequently with 100+. Since joining I have closely worked with 100-200 (not at the same time of course). I've had the ability to work in different roles/teams across the organization, which is not possible in smaller orgs.

While I agree with you in that working with scale is an incredibly valuable skillset, I don't think scale of users or data necessarily correlates with company size. There are many small(er) companies where you will work with enormous userbases or huge data sets.

Likewise you can go work for huge Fortune 500 corporations and the biggest level of scale you work with might just be at the level of a few hundred internal users.

The biggest learning opportunities at a large company are office politics, red tape, and bureaucracy.

My last job was at a a startup, now I work in a big company.

At the startup I set up Linux server instances on Google Cloud and Digital Ocean. I set up Apache web servers etc. I wrote Python REST APIs on the servers. I did Javascript web work on the servers. I also wrote code for an iOS app in XCode. I also wrote more than one Android app from scratch.

Now I work at a non-tech Fortune 100 company. I only do Android. 95% of the time I am working within one module. I also tend to work on similar features during a quarter and across quarters. How much coding I do can vary, but the amount I spend coding is less than the time I spend in meetings, or reading documentation another team wrote, or helping or asking for help from someone, or doing code review or handling the release process.

You're not necessarily going to learn "the right way" to do things, you're going to learn the large organization way to do things. You're better off at a small company with a good, experienced mentor than at a big company without one.

An example for a big company...HN is fairly simple, Reddit is a little more complex. Think of the notion of a post or reply or user on Reddit. Initially these concepts will be pretty simple, but as more features are added they become more complex. I can imagine what the internal data structure is at Reddit is of a post or a user. Not only is it probably very complex, I'm sure some of the data structure is vestigial, old stuff no longer used that was never cleaned up. Changes against these things are by teams, often tending toward the more junior, often on tight deadlines, and the codebase is an accumulation of many years of this. I don't know much about Reddit internally but it is an easy example to think about.

Why don't you just work at one or two big company and get your FOMO out of the way? The worse case is you make more money (hopefully?) and hate it but you never need to look back, while your best case is a much higher ceiling.

You're 30 years old, assuming you work for another 30 doing 1-2 years at 1 or 2 big corp isn't much.

I mean from my personal experience, it's really the team within the big corp that you work at that matters. The big corp can try to drive a cultural and larger goals but that the end of the day it's your manager and peers that has the most say in your work and happiness so if you're interviewing, I'd really focus on getting to know your peers, manager an if you get a chance, your manager's manager (director title, most likely)

I'd never say the experience at 1 startup would be the same as another - so why people are saying you'll have the same experience at 1 big corp compared to another, or even a team within the same big corp...is beyond me.

^ This is excellent advise

Edit: Primarily the bit about your team / manager, its the bit that will get you through the worst big corp can fling at you, in most cases.

> As I haven't really worked at big companies, I've always had this nascent feeling that I never really learned "the right way" to do things. I often feel like a "patchwork engineer", learning how things work only sufficiently to make things work in a smaller scale without understanding important big project/organization principles.

What you write reads like a typical ADHD Imposter Syndrom. Why do I bring ADHD? Because you are a jack of all trades[1], experience FOMO, work at startups, and are concerned with not doing things "the proper way". Been there, done that.

There is "Driven to Distraction" book by Hallowell & Ratay (https://www.amazon.com/Driven-Distraction-Revised-Recognizin...), which deals with ADHD in adults. This type of behavior is common. The crucial thing is to accept that one will never be (or should strive for) being a "typical [insert a job here]". So corporations and other well-specified jobs are usually (though not always) bad fits. And there is a lot of strength in that - startups, freelancing, consultants [2].

Furthermore, big companies push this narration that only "things at a scale" matter. I strongly disagree. All startups start from a small scale. And even in big companies, a lot of innovation comes from small, proof-of-concept projects.

[1] The complete phrase is "a jack of all trades is a master of none, but oftentimes better than a master of one".

[2] For me, school, studies, even Ph.D. were too standardized. Then I started to shine as a freelance consultant, and now I flourish as a founder. It is good to find one's niche!

Thanks for the book recommendation!.

I've often wondered about ADHD but since I know a couple of close friends with serious ADHD, I haven't considered it too much as I'm not comparable to my friends level.

Although, I tried ADHD medication (through friend) and it was eye opening how easy focusing on one task became, and how nondetrimental context switching and parallel scattered thoughts became for focus and anxiety.

I used to live for two years with my close friend, who has ADHD. Since I were way more organized than him, I assumed I couldn't have ADHD.

Only in the last few years I realized that I have ADHD (thanks for a friend who pointed me to some resources). Yes, including a formal diagnosis. Though this one brought little, except for my parents being mildly annoyed that they cannot keep guilt-tripping for not adhering to their very high standards of tiddiness, punctuality, organization, etc.

I reallly, really wish I had known it ealier. It would save me from a lot of guilt, shame, and approaching things the way that is doomed to failed (the same things could be approached differently).

When it comes to this friend - he is by far a person with the strongest ADHD symptoms above all of my friends with a formal diagnosis.

Medications - I recommend Armodafinil. Though, I would argue that for ADHD the most important factor is not with getting more productive with boring tasks, but finding the right environment (that provides a lot of dopamine).

Try it out! You're still young. If it's not your cup of tea, you can pivot back.

My FOMO issue was wanting to work in one of the sexy Silicon Valley style tech companies, after having only worked in big enterprise non-tech companies for my entire career. Recently made the switch last year. In my case, the grass was indeed greener on the other side.

I've worked at small and mega enterprise. I will pick small/medium over big anyday for how to do things the 'right' way. Enterprise doesn't care about the right way so much, too many policies and politics get in the way. Similarly you can also get a very 'just get it out the door' attitude at some very small companies.

However you can also find small/medium companies that understand that they need to ship, but also understand how to properly run things. There is a much greater chance of that happening at a small/medium company than any big company.

I've been working for a startup for almost 6 months now, but before this, I've only worked at relatively larger companies, my last company being the largest (7k employees).

I like the independence of working at a startup and the speed at which things get done. This is also a curse though, because it often feels like engineers are competing for who can own or take over a project first. Things are done quickly but also haphazardly; for example, I recently jumped on a project where the lead engineer whipped up the repository within a day and already added a Makefile that had a couple of completely broken commands due to a fundamental misunderstanding of the build process.

With larger companies, I liked that I can largely remain invisible if I want to. So long as I finish my JIRA tickets, I usually "sign off" early and leave my messenger on if I'm needed for any urgent matters. Usually the leaders aren't expecting me to go "above and beyond" like my current job often feels like. I fulfill my creative programming pursuits on my freetime, and I prefer it that way. Also, I do prefer designated PTO time as opposed to "unlimited PTO" like many startups now offer.

So right now I'm in favor of larger companies, but take this with a grain of salt because I've only been in the startup world for 6 months.

Tooling is better at large corps, they will teach you how to build things at scale. Autonomy is greater at startups, they will teach you to do everything yourself.

At a large corp, if you don't like the tooling, it sucks because changing it is akin to pushing against a mountain (doable but you will burn an insane amount of time and value doing so). At a startup, there's the instability and the nagging feeling that what you cobbled together could have been done better "if you just had more time."

It's a tradeoff between autonomy and institutionalization, and that really comes down to personal choice. Some of the best roles are where you can exercise your autonomy in a large organization (within bounds).

Im at a big tech company now. I’ve learned a valuable set of skills in my lengthy tenure, but I think your FOMO is unwarranted.

We’re bogged down in tech debt, legacy systems, endless migration projects, and worst of all, management chains on their way out being replaced by people managers. They’re in technical roles, bringing culture from legacy mega corps like IBM, or IT managers from cost center organizations who don’t give a shit about the product or customer experience.

My company’s corporate culture was unashamedly aggressive in doing big things, even if it meant burning people out.

Nowadays, teams working on critical projects are getting even more pressure than ever from incompetent people managers who don’t understand even the basics of what their team does.

And then you have entire fleets of teams who aren’t working on critical projects. They sort of just exist. Imagine a $400K cushy job where you write 10 lines of code in an entire quarter. Not just you, but your entire team just does random “investigations” every sprint. They ship nothing. It’s just a token job because a director or VP is focused elsewhere.

I don't think you are missing anything here. Both work in different ways (I have worked with companies as large as 250k+ employees to 2 employees). Both try to achieve different things (make something from zero, and create drastic value, v/s incremental changes and building and sustaining existing revenue streams) As an engineer: in bigger company, you will learn how large scale projects are pulled with so many people, v/s in small ones, you know what you are learning. In startup's favour: since a company from 2-1000 employees can be called a startup, so what I mentioned about large scale projects in bigger companies, you can learn that in these companies as well. I would suggest you to speak to more such people and get their perspective. You will figure out what both businesses offer, and based on what you want to do in your life, you can make an informed decision.

Agreed! I was in a large company for my entire career and only recently pivoted to a startup. I am enjoying learning about different types of challenges and how to go about solving them in a different environment. You end up learning so much about your professional self when you have to stretch your skills to apply to different situations.

It's mostly in your imagination. Big companies don't have any better idea how to do things, often worse. I think it's beneficial to work for a large company for a while, if only just to see how things are and to say you've done it. But as far as getting to : "doing things properly", that's something you will need to figure out as you go, by applying critical thinking and by trying to work with competent colleagues where possible.

Oh you are not missing anything great at bigger companies. There is no “right way” there either. But I think you have to experience both sides yourself to understand. I can predict the future: you will go work for a big company someday and then go back to a startup.

I had a serious sense of FOMO after working at startups throughout my 20s. In my early 30s I joined a FAANG company and absolutely hated it, left FAANG after a year and came back to startups. There are some really interesting processes that these companies use, but the problems that they have aren't broadly applicable to startups so it's not so much about "the right way" as it is about "their way". However, if you really want to try it there's very little downside. I found it pretty easy to jump from a FAANG back into startups and now I can sell "that I've seen both sides" when interviewing / managing.

30s is indeed a painful age to reach. There's a reason many celebs have checked out at 28/29. 30s is so depressing that no matter what you achieve it's like well it's expected or it's so late so no one is impressed.

- Made a great company. Big deal, he's in his 30s.

- Cured cancer. Pfft. Einsted redefined relativity at 26.

- Booked a trip somewhere. Checking off yet another goal off of the bucketlist.

- Built a great body. Well he's just desperately trying to hold on to youth.

I mean it's not even 30 it's 3O. The O stands for Over.

Perhaps you should hang out with different people.

A solution to that attitude is to do things not in a race to please others, or for the sake of doing something impressive, but for their inherent value. Doing so might require a change of one's personal value system, but it's probably a change for the better. Extreme example, but curing cancer to impress people is kind of missing the point.

I never got this feeling and a I'm a bit past 30

> I mean it's not even 30 it's 3O. The O stands for Over.

Good thing I'm 32.

I think this could happen at a small or large company. It sounds like instead of blindly choosing a company, you need to figure out how to pick teams and projects where you can grow.

Some things to look for include senior engineers who are happy to mentor (not teach or guide or instruct but to mentor), look for companies that are growing or making new products, and if all else fails look for a place with some sort of educational stipend you can spend going to industry conferences or what not.

You seem to be putting "the right way" on some kind of pedestal. There is no one right way. There are right ways to do software in a lab, there are right ways to do software in a startup. You've learned those two. You lack exposure to one of the right ways to do software in a megacorp that optimizes for making developers fungible resources and maximizing shareholder value. It doesn't make you somehow less of a developer not being able to do the third. If you want to chase a high TC then by all means, jump in and learn it. But, that's the only reason. Learning how to develop for a megacorp won't enrich your life, enlighten you or make you feel anymore like you've made it as a developer.

Also, the grass is greener won't stop. Once you get to the megacorp you will wax poetic about your academia and startup days. You'll tell those fun stories to your coworkers because you stopped accumulating fun work stories when you joined megacorp. You'll occasionally think about going back to grad school, or joining a startup again; but, you'll remember you have an RSU vest in 2 months, better stick around at least for that, can't leave money on the table...

Just seconding stuff that's already been posted by multiple people:

1) You should absolutely try both. You've already done some startups, so now would be a good time to try a big corp. They each have upsides and downsides, and it really depends on you as an individual as to which one you'll be happier at, as well as more successful at.

2) It's all about the people you work with and report to. Really, you should choose based on the team rather than the size of the company. If they are all smart, cool people you get along with, then you'll be fine even if it's a fucking bank (source: I work at a bank presently and it's great). On the other hand if they're incompetent, egotistical assholes, it's going to suck big time regardless of how many foozball tables or beer fridges the company has.

editing to add, at a big corp, a good manager should understand that their job is to insulate their reports from as much of the bullshit as possible. That's critical. You should be able to get a sense of this during the interview, even. If they're up front about the bullshit from the get go, that's a good sign. If they're actively trying to make you drink Kool-Aid... run.

Amazon probably has one of the worst reputations available for a major tech employer, so even if you find the grass rather brown, it may just be Amazon.

I just joined a big tech after 10 years in startups and honestly it just requires quite different set of skills.

Grass is always greener, so there is just a trade-off on both sides in terms of various vectors like money, culture, stakeholders, scope of work etc.

Now what I also always felt that in startups I just didn't learn things that I also needed to, to become a better PM.

For instance, in our $50m ARR company we ran production-driven development, no tests and very autonomous structure until the company hit around 100 employees and started shifting.

In the company that I joined - we have around 1000x microservices and my product touches around 25 squads that I need to get approval before we even ship a single change.

Is it bad? No, its just different. But the only way to know is to try it. I always thought startups are cooler but now I am humbled to admit that I was also missing learnings from BigCo's like management, structure, async writing of documentation etc. and I kind of enjoy it!

I have worked ~ 10yrs in each.

Larger companies can have better structure and mentoring available. They can also have more resources and work on more impactful problems. Public companies can have more liquid equity if that is part of the compensation.

Smaller companies can often provide opportunities with more customer impact earlier in your career at the cost of drinking from a firehose and with less resources available. Total comp wise, on average, startups will pay less because their equity is often illiquid and ultimately worthless, however the home runs can pay dramatically more than a large public company will.

I self identify as a roboticist and a generalist. Holistic systems thinking can be very valuable to a broad range of businesses in my experience. Keep learning the mental and mathematical models of your field and it is likely to payoff.

> I've now worked for about 3-4 years, so still a junior, but mostly at startups (and in my 3rd one).

Your issue here is really tenure , there’s a lot of software engineering fields for which you won’t know anything after a year in the role.

I've never worked at a larger company (>100) so I could be wrong but I don't think I'd enjoy it. Endless bureaucracy, office politics, and stifling policies. At a smaller company I can see my impact directly, I have the power to actually make decisions on how things are done, and I get to build cool new things. Don't assume that big companies know "the right way" to do things, they are just as fallible and sometimes even more so. They can fall into the "that's the way we've always done it" much easier than smaller companies. Also I can tell you from personal experience that more people/engineers does not mean a better product. A better funded one maybe but without naming any names let's just say that I've consumed APIs or similar from massive companies that I once looked up to or put on a pedestal and their API was trash and/or their software was a mess. It really helped break my long-held assumptions that they hire the best talent and produce the best code.

Don't feel like you are missing out, you are only missing out on a bunch of headaches IMHO. I've only worked for smaller companies and I have no doubt I could swing a job at a larger place if I wanted, I regularly ignore recruiters from AWS and the like because I don't want to work in that type of environment. Do what you like and make sure you get paid well for it, past that don't worry about company size.

I have experience working at a small "start-up" (3-5 people), medium (50-100) and large (10k+).

The small company gave me the confidence and experience to dig myself out of most situations and turned me into a "jack of all trades, master of none" (much like you describe yourself).

The medium company was a consulting firm so I got to work with other companies of varying sizes (including government organizations). Having worked multiple roles for a number of organizations, I gained the breadth but not depth. I was exposed to internal policies and workings of these organizations without having to actually switch jobs that many times.

When I joined the large company I brought with me the benefit and knowledge of having worked with multiple orgs, which is something that was lacking at the time for the teams I worked with. Having worked here a few years, I've gained invaluable knowledge I wouldn't have gotten at small firms. Being a large global organization I get to work with vastly different cultures and experiences, all of which is an overall benefit to me.

Having a variety of experience will make you well rounded. You will have positive and negative takeaways which you can apply in your future roles. And who knows, you may actually enjoy the large corporate life.

Is the grass greener at big companies? It entirely depends on what you are looking for and your personality. Is it valuable? Absolutely. Anyone who says otherwise is closing themselves off to invaluable experience.

I've hopped around a few medium sized established companies and early stage (pre-series A and series A) startups over the past 8 years as an iOS developer.

With coarse grained detail, it's a fair characterization to say that big companies require more navigation of interpersonal politics and hierarchical structures within the company, but afford you the opportunity to work on (more often than not) bigger problems (but you may be a small part of that big problem). And on the other hand startups allow you more autonomy and the chance to work on a wider breadth of the product yourself.

I've been told more than a couple times in bigger company land to stay in my lane, while in startup world that more and more executive functioning is required of me.

Both are valuable and right now I'm in bigger company land, that is until I get the itch again ;) Bigger companies tend afford more work life balance and respect your time, but your millage will vary. If you plan on starting a family anytime soon then it might not be a bad idea to situate yourself at a big company for a while.

One key for finding fulfillment as a smaller contributor in a larger company is finding personal validation outside of work. If you find things are going too slow for your taste and this frustrates you, then realize it's by design; people have lives outside of work and would like to live them :)

Working remote is just as viable in either scenario for my case, but I'm less sure about yours since robotics can only be simulated up to a certain point before you need actual hardware, right?

Technically - Big tech companies have the advantage of big projects, on average good leadership, and a high tech bar. Generally there is someone who knows how to do something in the Big Co's way, and you can learn that technique. Most Big Cos do not support going off the reservation however, and there are usually sacred cows which poking will just result in termination. As an example, even if something is an internal tool used by two people on your team, and that is all it ever will be - you are probably going to be required to make a redundant deployment with unit and integration tests, and full CI/CD pipeline.

The other major advantage of Big tech is typically financial, there is no guarantee that this will last indefinitely - but over the last 15 years the top tech firms have paid better than all other options by a wide margin. This isn't necessarily unique to big tech and could apply to any tech company considered a "top firm".

These trends will likely continue until tech firms paying top salaries either become too bloated to innovate and instead focus on building strange non-profitable vanity projects - or are outmatched by companies using lower cost engineers.

I've been at most stages except early-stage startups.

The main tradeoffs are

- Cash vs lotto tickets

- Breadth vs depth of experience

- Knowing everyone in the company vs being more anonymous

- Knowing more inner workings of the company vs being shielded from those details

- Having broader organizational support vs. doing/learning things for yourself

- Some will say work-life balance, but this varies wildly by company and team

> I never really learned "the right way"

Large companies often do things in very idiosyncratic ways that work for them. These approaches rarely directly translate to startups. Different scale, different tools, and when you're massive, the tools aren't commoditized.

The other part of this is your experience. There's a difference between hacking something together that works and intentionally designing something that works. Some of this comes with experience, some with focus and diligence, but it's orthogonal to the size of the company.

> I feel like I've also cornered myself with my resume / experience by only working at startups, and might not even be a lucrative candidate for larger organizations.

Big companies will happily consider you for mid-level IC roles. They want good engineers. I'd argue it's a little harder to go from a big company to a startup because it's easy to get pigeonholed in a particular role, and you're less likely to be familiar with standard tools everyone else uses. Big companies don't have this problem because no one they're interviewing is familiar with their in-house toolset.

I've done both and there are pros/cons for both tracks. Currently at a startup - it can be total chaos with crazy highs and ridiculous lows. You have to love solving problems and particularly the problem your company is solving. You realize at big companies you have more resources in theory but while there's a department or someone to do whatever you need, there's also internal politics that tends to come w/ bigger orgs to access the resources, move up etc. At a startup you figure out how to help fill those gaps and do things that aren't in your job description because everyone has to just figure it out and yeah that can be exhausting, but it can also feel really good when you get stuff done. If your bet pays off, it can really pay off but it's important to take a hard look at the risks the company is up against to make sure the upside is there and realistic. I'll also add, my closest friendships in business have been from my startup experience.

Don't bother working for a large company. If you haven't seen it already, just watch the movie Office Space (https://www.imdb.com/title/tt0151804/) and you can see everything you need to know about doing software at a big company.

That being said, you have to understand that your new job isn't at a "Big company", your new job is at Amazon: a completely different beast. I live in the greater Seattle area and I can tell you there are two types of Amazon workers doing software development - those who quietly work their jobs and never talk to non-Amazon folks about it one way or the other (e.g. "my Amazon job is great! You should work here!" or "My Amazon job is hell"), or people who are Ex-Amazon who have NOTHING good to say about working there (except for the fact that they left the job). Be careful.

You're not saying what roles you'd try and go for at a big company. If it's robotics, I'm sure they'll assess your tehcnical knowledge and then not sweat the size/scale of your engineering work. If it's a transition into non-robotics software engineering (which is what I'm guessing your friend did), you might not have the level of experience and skill to immediately get a software job at Amazon or other big companies, but you'll for sure find many companies willing to help you change careers. Just seeing robotics on a resume is enough to pique my interest and want to talk, I'd imagine lots of hiring managers feel similarly. I don't think I've ever assessed a candidate and felt that they missed the boat on doing things the right way. It's really about assessing potential and attitude, and if those fall into place, the "right way" can be taught.

Yes that's exactly what my friend did.

I fear exactly what you said that I might not have the level of experience to be able to do the same, and part of that desire is also hinged on the "master of none" part.

I've (so far) not come across any really "big" robotics company (that is not industrial arms related, which to begin with is not that interested in "jack of all trades" and more interested in experts in Software/EE/mechanical separately). So if big company is a goal, less robotics and more "software" is the only reasonable career nudge.

It is encouraging to hear that the diversity in the experience can be seen in a positive light though, so thank you for relieving some of my anxiety surrounding it.

I started my career in a startup and had a similar FOMO, always thinking that the big corps have figured out all these problems we were struggling with, hoping I can one day learn to how.

Then I joined one and had an eye opening experience - it's not true at all. They might have better tooling (although that's not even always the case), and they might have better established ways to do things, but the engineers aren't any better than at a startup and they deal with the same problems as you.

A lot of work at large corps is "patchworking", and a lot of code is pretty awful and won't teach you "the right way" to do anything. Like anywhere else, there's a lot of v1 code that doesn't get substantially improved after it's shipped because the team has moved on to something else. There can be a lot of churn where code gets moved between teams, rewritten and discarded as priorities change and people come and go. Only a minority of core systems get the benefit of being iterated on and evolved over a long period of time.

I believe that the best way to learn how to do things right is to make mistakes yourself and learn from them. Work on a single project long enough so that you don't just write the v1, but also the v2 and v3 and v4 that make you see the mistakes you previously made and let you figure out how to fix them.

Startups can be a good place to do that, because unlike in a bigger place, you might actually be given the scope and responsibility to do that even as a junior engineer.

You are right that maintaining things is a good way to learn, but you could equally spend 3 years moving on from one new micro service to another as the roadmap priorities change every 6 months, with very little opportunity to spend some time with your own code and learn from it.

If you've worked at 3 different places in 3 years, you might not have seen the benefits yet, but if you try to stay and work on something for long enough, you'll learn a ton.

My experience is quite similar (down to the robotics specialization!), but my first jobs were in big companies in aerospace, oil tools, oil exploration computation, and eventually, computer manufacturers and software. At each of these, I learned some good things, but to be fair, only four of those companies were well-run enough to teach me anything of lasting value. (FYI: Rohr, Hughes Tool, Chevron, Sun Microsystems)

Since I left big corps 20 years ago, I've spent almost all my time in startups. Most failed, but two were successfully, if not terribly profitably, sold. (As CTO or similar for all, I'm happy to say that the failures fell for business or founding team issues, not technical reasons - my teams always delivered the technology/product, often on impossible schedules and budgets!)

Yes, it's true that (unless your startup is wildly successful) you don't learn to scale things as much in a small company, but in reality, scaling is overrated, and many people spend way too much time foolishly trying to optimize for it. What startups DO teach you is to think about building great solutions for the product at hand. The lack of time and resources inherent even in well-funded startups (I've had the fortune to work in one of those) drives more expansive considerations of options and creative approaches, and a focus on the end goal rather than the process. Big companies simply cannot think this way, and I am very fortunate to have had a couple of my own startups under my belt before I was invited to join others. I think that proved that I had not been made utterly useless by my big-corp experience. (I'd also done a lot of R&D work in the big companies, which is as close to startup mentality as they can get.)

I could go on for quite a while, but suffice it to say, you're not really missing much, if anything (except miserable, bigoted big-corp Diversity, Inclusion, and Equity (DIE) training and policies that will never let you speak freely for fear of HR reprisals...) When I am asked to build teams, unless the client is a big-corp culture that only another bi-corp mentality person can survive in, I strongly prefer to draw from people with smaller company experience - they are usually considerably more capable across disciplines, much more creative, and have an MIH (Make It Happen) mentality that you never find in the big corps. In short, having done both, I consider big-corp experience to be more of a detriment (especially true for PhDs IMO), and startup experience to be invaluable for developing real teamwork, creativity, and the ability to make it real!

My FOMO is that my life is wasted being a corporate cog in a machine and has to come to office to work daily warming seat while I can do my job in 4 hrs of work.

But then I need the money of a big corpo (read: FAANG pay-band) to one day have a financial independence and dream of creating my own startup where I can go work remotely at my cheap COL (cost of living) country and be near my families, solving real problems than just another dating/ecommerce/social media/investing/real estate eque app.

Yeah, a lot of the startups these days also focusing on those dating/ecommerce/social media/investing/real estate business, which I don't find any enjoyment in.

So, why not just work and slave away at big corpo earning FAANG pays.

There's a middle ground, too. You can work at a small company that isn't a VC fueled startup. They exist out there. Some in SV call them (with a bit of sneer, sometimes) "lifestyle businesses" but I know some developers who have pretty good lifestyles working for these businesses.

They can be both product and consulting companies and you can learn tons, meet great people, and have a good career.

What you won't have is the startup lottery ticket or the super cush bigco salary/reputation.

Only you can decide if the tradeoffs are worth it, so if you have the desire, give it a try.

Do note that every workplace has its downsides/warts, so the key, in my experience, is finding a workplace where the downsides are acceptable.

Me: older self taught startup guy who transferred to a large edu a few years ago.

Not all large co’s act as a monolith. Some allow smaller depts to run their own shop while having access to their resources. This could be bad in terms of learning ‘the right way’ but that’s what interviews are for - to ask them questions too!

You really want to care about the mission of the large co though.

If you find one you like, get in touch with their recruiters, show them your resume and ask point blank if it needs restructuring to make it through their weedout filters. You bring things to the table that don’t always fit in the boxes.

Also widen the scope in terms of how senior you want to go if the co promotes well from within.

Good luck!

I've felt the exact same way after working (consulting) for mostly very large companies. I'd love to do a startup at some point in my career and sometime I have FOMO on that experience. The grass is always greener.

I can relate to a lot of what you've said here. I've built a similar super-generalist profile in software engineering and have spent the last decade in startups.

Compared to my peers/friends in larger companies, I've always had far less politics/BS to deal with at work. I would not say its non-existent; sometimes all it takes is one bad hire, and the smaller the startup the more outsized the impact of the bad apple. So in that sense, impact is a double-edged sword.

On the other hand, I've been able to build a super-generalist profile because of the startups I've worked at. Backend-engineering, frond-end stuff, DevOps, hands-on data-center experience, automated QA, SRE, growth hacking; you name it and I've probably checked that box off at some point in the last 10 years; mostly because I've been able to cultivate good relationships within the company to be able to move around different roles. This would be impossible in a large company, even with a lot of personal connections. A few jumps are possible, but not the kind I'm describing above.

The smaller size of startups also means that you have fewer people between yourself and key decision-makers. I've had the good fortune of being able to work directly with/report to CXOs for over half a decade, which IMO provides a lot more exposure to understanding how a business operates. I would not trade that for working with mid-tier management in most large companies.

With regards to not being appealing to large companies, I'd say that is not true. I've known folks who've moved from startups to FAANG companies in their mid-40s without any issues. The experience always counts. You may lack some of the specialization, but you can always compensate for that with breadth of experience.

Ultimately it boils down to what you want to accomplish. If your goal is to eventually start your own business, working at startups is a great way to get the requisite experience. It is definitely not a walk in the park though. Being able to work with little to no direction, constantly changing goal posts, and the lack of any structure does take its toll on you slowly, but surely. However, I can say from personal experience that I don't regret it one bit.

If you only work at startups you may never really know what the real industry best practices are. The people who are best on any given topic have a tendency to keep it a secret, so you're not necessarily going to be able to learn it outside of direct experience. Startups will often choose the expedient and obvious path to shipping that MVP, even when that pattern has known problems. Of course you can choose an innovative startup and get the opposite experience, but you'd have to choose it carefully and probably on the basis of personal relationships to be sure.

I've done much of both.

Working at a big company is much easier, but it's harder to get things done. You'll have at least 10 hours a week in meetings. The CEO or a guest speaker will deliver a Ted Talk speech once every 3 months.

Try getting a server deployed for an internal side project. Even if everyone wants it, your wading though miles of redtape.

Startups are more fun, but less stable. The stress is intense. I'm in my 30s and unless I personally know the founders, I'm never working in a startup again. The Company might just randomly shut down !

I worked as a self taught software engineer for over the last decade starting from junior and climbing my way to seniority at small startups, some where I was the first engineering hire, some where I was employee #30-50. Last year for the first time I made the jump to BigCo for the first time. I am seriously loving it. People are more professional. Surprisingly diversity is higher IMO - startups can easily become culture fit clubs as they try to build a brand.

Here’s my ranking

1) working at YOUR OWN startup/for yourself

2) working at big co

3) working at a startup owned by someone else

I think you are being too hard on yourself and suffering a bit of faraway fields are greener. My post college employment from went from companies of size 10-35-3000-50000-60000. I'm the kind of the opposite of you in that I want to go back to a smaller company. If you are going to do it do it now but beware of getting trapped financially with no way to go back to living on a smaller income if you wanted to.

Theres also the nice middle-ground of smaller but more established companies. They may not IPO any time soon but aren’t so chaotic, and also don’t have the multiple levels of bureaucracy of a big company.

Usually in these companies roles aren’t as formally defined, so you can grow in skills and experience even if the company is never going to be a unicorn or re-define the future of ‘XYZ’.

I'm at one and it's pleasant. Pay is smaller than my country's large corps, but I can basically work on all projects and do things however I like. There is ML research as well as interesting dev projects.

It's sometimes annoying to see people use lazy solutions and refuse to learn the proper way, but since I took ownership of the important modules I use early on, I've built a small bubble of good software I can build upon.

I'm working in a public company and I have FOMO about startups. Problem is the public company pays 3-4x (liquid) what a startup would. For now my compromise is that I have a number, and once I hit that number I can take jobs that merely pay the bills with modest savings instead of really moving me ahead. But who knows, it's hard not to get addicted to TC.

I have a corollary question.

If you're a hiring manager in a large company, what are the pros and cons you see about hiring engineers who have only worked in startups?

Vice versa, if you're a hiring manager in a startup, what are the cons and pros you see about hiring engineers who have only worked in Fortune 500 companies?

Sounds like you've got some Impostor's Syndrome, just like all the rest of us.

Maybe also look at other dimensions, like tech vs non-tech or consulting vs product-oriented. For me, switching from consulting to a product-oriented company (both small companies) made a huge difference.

YMMV and really depends on the startup. I moved from a startup to a big company and back. My very personal experience was this - I learned more in 5 years at AWS than in my entire 20 years career. Then I moved to start my own company with 2 other amazing co-founders, I can say I learned more in 5 months at my own startup than anywhere else before. My experience from AWS definitely helped, but I think that the pace of learning and managing to "do more with less" (as much as frugality is a leadership principal at AWS, when you run your own seed stage startup, frugality gets a much more realistic meaning) - is orders of magnitude stronger at a startup.

If none of your startup peers or founders ever had any corporate experience - while it might be good (big corp didn't "ruin" them yet) it also might mean they will repeat mistakes or have to learn from scratch things that become common knowledge after a few years. How to run effective meetings, business writing, hiring practices, UX, scalable infrastructure and architecture. At AWS, there isn't a distributed systems concept that you can't just find someone who literally wrote the book on it and you can just ping them on slack.

So tl;dr - it all depends, I recommend diversifying your career, and just trying it out. I think that a mix of startups and big companies can only do good to your career.

I worked in a startup for my 2nd serious job in Canada, and it was a mess.

The company burned through $7 mills, and went under in under a year. Such a mess. I will never ever work for a startup again.

If I owned that company, I would've already recouped the money many times over.

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