Ask HN: When should one leave a company based on learning stagnation?

1. One way of learning is to apprentice to a master craftsman. Another way is to figure out things on your own. Yet another way is to take stuff you think you already know and try to explain it to people that knows less than you. None is better than the other, and each has it's unique insights. Maybe you currently don't have some greyback to follow and learn from, but when you find your teacher, you will be able to pick up more of what he says by virtue of having experienced first hand what he's talking about.

2. Kid, life's a marathon, not a sprint. It is pretty much irrelevant if your options will vest now or in a couple of months. What you really need to be in the look out is for dishonest leadership. If this is a one off event, all is OK. But if it is a trend of the founders failing to respect previous commitments to employees... you don't want to waste your time around that kind of people.

3. Assuming healthy leadership, it sounds like you have earned a key role in that company. You probably want to part in good terms and maybe work with those people again, so please speak with your manager about your concerns. Maybe something can be arranged, maybe not. Maybe you can negotiate a better deal if you feel your responsibilities have grown faster than your compensation. But whatever is the end result, your creed as a professional will be much better if you speak beforehand than if the first time your boss hears about your dissatisfaction is the same day you give notice.

Thanks for addressing my concerns point wise! I have been a little worried about the stock option move ever since I have come to know about it. It has been the only sort of red flag as of yet about the leadership, but I will keep your words in mind and see if there is a trend. You have given very actionable advice. I guess talking to them about this should be my first step in any scenario I proceed with.

Glad that you find my opinion helpful.

One more piece of advice that came to mind. Maybe you can negotiate that part of your current responsibilities be offloaded to a more junior engineer with the right balance of knowledge and attitude. This would serve the dual purpose of releasing some of your time for more "research oriented" activities while simultaneously providing you with the intellectual challenge of having someone to mentor for the next 3-4 months. Hopefully after that time you will have a better idea of what you want to do next in your career.

This all of course depends on you having a boss that actually listens and is interested in having the company's personnel grown into the professionals they are meant to be, vs extracting the maximum amount of labor each quarter.

I'm in the same situation, and to be honest, I'm not really sure.

First thing first, for all practical purposes, startup stock is useless -- and especially if you're already thinking of quitting.

In my situation, I joined the startup right after college, and it has been almost 2 years for me as well. I was the first technical employee, and except one other employee (the second hire), I'm not seeing other people better than me joining either. That said, there are a few things to keep in mind:

- Startup is NOT the place to be learning technical skill, especially early stage startup. The big 4 will serve you much better than that (and I know this going in). However, one of the things I've learned over the last year is that there are more to it than just technical skill. I have no doubt that I haven't been learning anywhere as fast as I could have in term of tech skill, but I've learned other stuffs that might just be as valuable: from dealing with (less than ideal) team member, dealing with expectation (mine and others), being resilient, and a gazillion things that probably make me a better human. Startup is emotional, for better or worse.

- I remember reading a quote that if you can only learn from people better than you, it's gonna be awfully hard to learn anything. As you eventually get better, you will have to learn from everyone around you.

- Since both of the previous points are extremely personal and subjective, I think that the one most important point to consider would be this: do you think the startup have any fighting chance? If the startup grows, both of those previous problems will fix itself. If the startup have no chance, well why would you stay there anyway? In my case, I can't answer that question with either a straight yes or no, so I can't decide.

I am also struggling with whether it is time for me to move or not. But I think your point about only learning from people better than you... that is a interesting perspective.

Like the OP, I think we consider ourselves to be at the "hyper-growth-learning phase", where we can really accelerate our potential by working with really talented people. But yeah, eventually you're going to be that "Senior Developer," and it'll be up to you to continue improving and helping others improve.

I've only been in the industry for 2 years as well.

Right now, I feel like I'm the only person on my team that is continually self-improving and trying out new things. It's always me bringing back new things and sharing with the team. Sometimes, I feel like I could benefit way more - like 2-3x - if I was on a team where everyone was self-improving and we could just all feed off that energy.

I have an extraordinary amount of autonomy. My year end review only consisted of, how I knocked everything out of the park and something along the lines of helping get into more of a leadership role.

Sometimes, I think - am I doing so well because everyone around me is just average?

Do I wait around to be promoted into leadership? I mean I've done fine self-learning and keeping myself up to date. But honestly, I think would hate to end up being in some sort of leadership position just because I've been with the company for a long time and have delivered consistent results, and then end up with mediocre tech skills.

Or do I say its time to part ways and focus on becoming a really good engineer and join a team that can continue to accelerate my skills?

For me, I am leaning toward the latter. When I feel I hit that "Senior Developer" phase, that's where I'll re-evaluate where I want to go next.

The autonomy part you mentioned is something that I forgot about, but that's definitely a very important point as well: from what I've known, there is a huge limit on what you're allowed to do in a bigger environment. There are a risk of learning things that you might not like -- of course, I've never worked in one, so takes it with a cup of salt.

Personally for me, the other thing is that I like to learn a lot of things, and I just figure that whether now or a few years from now (when I'm "Senior Developer"), there would be just as much things to learn about. I figure it's just better to learn how to learn and get people to teach you stuffs without being in the same work place.

Another thing is that leadership skill is different than tech skill, which is also different than "technical leadership" skill, and this is back to the whole autonomy thing: I got a chance to try my ability to cram the idea that "not everything in a language need to be used" to the js guy, or telling the Java guy "may be we will just decide to rewrite our ORM with another library and putting up 5 layer of abstractions could potentially help us do that" is not a sound idea. Engineering skill set seems to be distinct from coding skill, which I'm not sure will qualify in the usual sense of "technical skill" or not, since you can't put "good variable and function naming" on your CV. Believe it or not, working with really bad code forced me to come back to first principle and ask question like "why should we use function", which I don't think you will have the chance to do in a bigger code base?

There are also benefits from working closer to the business: you learn what actually is important, and what is crap.

Of course, all of this would apply if you join another startup ... and I don't mean for any of this to be an advice or anything, more of a commiserating comment.

I can't really put my email here. But since you and some others are on their main account, do you mind if I have a way to contact you? I just want to follow up a few months from now to see your decisions.

For sure, I've added my email in my profile.

Yes I believe the autonomy part is important and helps you learn stuff about managing expectations of all stakeholders in a product, getting work done in a distributed manner from other engineers is also an added skill (which IMHO is bloody frustrating to learn). Also I have learned a lot on maintainability and the cons of technical debts. But when something that excites you most is the joy of learning or building something new, the problem here becomes an ever growing chunk of time that goes into maintaining, supervising or corrective processes rather than creation process. Perhaps this would be true for most places... It's just that for quite sometime when you wake up in the morning and start wishing it was a holiday... something needs to be done I guess. Thanks for sharing your experiences though. It helps to know I am not alone in a dilemma over such a situation...

I have been in a similar situation. I was a co-founder at a company, I was not joining with technical skill. I had more marketing and business development background. I had some knowledge but was just starting out.

The opportunity was fantastic and I learned a lot (things todo and not todo). However, as you stated I felt the exact same things you did:

A. Learning Was beginning to stagnate - I was no longer able to continually learn and develop.

B. Company was not growing and my confidence in the rest of the team plummeted. We were focused on the wrong things and promising things to customers and partners that we knew we could not deliver on.

These two things alone where enough for me to know that my time was done. There is a post on Medium, "Rate-of-learning: the most valuable startup compensation" (link at the end) this is why I had to move on. I knew that for me to continue progressing and learning the best option for me was to leave.

In regards to equity and raising capital. I learned two things (1) people can become extremely greedy when equity and raising capital come about and (2) greed can easily lead to ethics and values being compromised. I don't know your exact situation but I would keep these things in mind.

Hopefully this helps. Best of luck!

Link: https://medium.com/@KyleTibbitts/rate-of-learning-the-most-v...

PS: This is another post that may help you by Ryan Hoover. Great post! https://medium.com/@rrhoover/knowing-when-its-time-to-move-o...

Thanks for sharing your experience. I hadn't read the post by Ryan. Thanks. This does look really encouraging and helpful at this point.

I was on the same boat. After working for 2 years delivering over 5 projects, I decided it was time to move on. Not to sound too arrogant but I was fed up teaching and guiding others. I was doing over 80% of work by myself and it was a hectic period. Since then I have moved to a different company. So far the experience has been really positive.

I was just wondering how did you deal with other senior team members that still stayed back. Hope there was no bad blood. I am curious as it seems you leaving would have been a big blow to them and they could have reacted a little adversely maybe out of self-interest...

The whole team relied on me so it was a hard decision. I gave them a month notice and slowly transitioned myself out of the meetings, code reviews and architectural decisions. I felt bad but it was the right decision for me and my career.