How do I get over constant failure?

Possibly unpopular advice on HN, but stop joining startups. Idiosyncratic-Culture Risk is off the charts for startups. Join more stable firms with a more "boring" but predictable culture where things get delivered every Sprint, everyone gets paid well, there is no Mountain Dew being guzzled at 8 pm in the office to meet some deadline, weekends are truly off, and your mental health actually recovers. Your dream jobs are leading to your nightmares.

> ... It's been a couple months and I have achieved nothing. Not a single PR merged. ...

There's a lot to be said for getting into a rhythm of picking an issue, solving it, and merging it. Doing it a few times can be a real confidence booster.

What's the reason behind having no PRs merged? Did you create them, only to have them rejected? Have you not completed the work for any? Is there nobody to review them?

Also, just how big are the issues in your tracker?

I'm going to assume that everything is in place to get a PR merged. Given that, try to find a way to shave off an issue from a larger issue. Go for the smallest possible unit of work that might be useful. Then focus on getting that one PR merged. Rinse and repeat.

Very, very few things survive long-term. Experiments fail, projects fail, market leaders change. I know talented people who have worked long careers & never seen a product ship.

Clayton Christensen made an academic career at Harvard researching market leaders getting replaced.

The Office of Advocacy of the U.S. Small Business Administration reports about half of businesses fail after 5 years, https://advocacy.sba.gov/2011/10/19/what-is-the-survival-rat...

Skill plays a role in these outcomes, but so do other factors including luck & imperfect information. The top engineer at Blackberry was a rising star, until suddenly the iPhone showed up.

After a couple of decades in the field I have concluded that the hardest part in this job is not the technical one, but the dealing with yourself. Yet, through the process you get to develop virtues that eventually make you a better person. Don't give up :)

- Deferring to others for strategic startup/career/tech advice

- More immediately, however, from the way you wrote it sounded to me like you're really, really down on yourself & have this constant churning sense of fear (above/beyond the typical "background radiation" of our insanely distressing life right now)

- I hope I didn't misread, but it sounds like generally you've got your $$$ locked down for foreseeable and are getting paid to work with high-caliber people

- Just going based on what you wrote, all the stuff going at this new gig (omg manager left, less-than-flawless onboarding, new person with lots of ideas learns they might need to come up with different business-valuable ideas, it's unclear how to get stuff merged, etc etc) are not that unusual. Your career trajectory as you describe sounds like somebody who actually gaf about engineering

However, that underlying fear or whatever the gnawing feeling you describe that threads through everything, might be worthy of further examination. Like figure out why is that monkey on your back?

If you're not already, hang out with kind people who don't work in tech

Also this group is like the khan academy of mental health-- check out the mirror exercise: https://wiki.healthygamer.gg/en/Insecurity

Don't know you but rooting for you

I have the same problem as you right now. Long break from work during the pandemic, joined a new company, and have only managed to merge one tiny PR in my first month. It feels terrible.

What I’ve figured out is that I need to have a new way to measure myself. I wanted to be a hotshot from day one, and impress everyone by cranking out new features. But on a project this complex, it will take half a year to ramp up and become an important part of the team.

In the meantime, I’ve realized I can’t simply call myself a failure every day. I need to find smaller goals that I measure myself against, like learning a new part of the codebase, building a relationship with another developer, building a little prototype that might not get used, and so on.

It sounds like you're a holistic or big picture type. I struggle with this too. I don't have all the answers but my advice would be to try and focus on a smaller thing and get a win with that. Don't propose several projects, propose one and give it enough attention and proof that it's hard to refuse. Are your proposals measurable? Are they valuable? Are they framed in business context?

If more is thrown at you, push back using phrases like "adding this initiative may put effort #1 at risk. I think we should concentrate on effort #1 a bit longer while #2 takes more shape"

Why are your PRs not being approved? Do you need more time pair programming so what you submit is more aligned with reviewer expectations? Have you asked for that pairing time?

Overall I hear two disconnects, one at a business/product level and one at the engineering level. Your expectations sound out of alignment with your peers. You might try and work on relationships, build trust, find the fun puzzle and try and enjoy any little bits you can.

Stop going for that PR. I don't even know what a PR is, but my guts tell me that you should stop pursuing that. Start making yourself useful. Do small stuff, support other people. The guidance you miss - start giving other people guidance. Ask for advice. Don't think you know it all.

The new very successful startup, the many high-performing people. Is that the truth or is that appearance? Fake it until you make it. That may apply to people, but also to companies.

Find a hobby, something outside your workfield that gives meaning to your life. If I hear you, you are successful, but you choose the wrong companies. If they pay you and don't complain, then you are a success in my book, much more successful than I ever was.

Most companies are dysfunctional. If you find a company that is able to take full advantage of you excitement, passion, enthusiasm and drive... you're lucky. Don't take this as a reflection on yourself, don't feel any obligation to suffer at a job you don't love, just keep looking for the right company. You might get lucky and find it quickly, you might get unlucky and spend years, but each time you get a job you'll hopefully learn more about what you need to look to avoid. A great privilege of technology is that job hopping isn't punished because technologists are in such high demand.

There's a lot in here!

Having read some of the comments, it seems really important to me to center the information that you're queer, supporting a disabled partner. I worked in tech from 2013-2020, and from 2015-2020 my Dad's health was very fragile, and he had made no financial plans. I became his guardian, paying for homes, doing the paperwork, managing the care, and I think this is a huge piece of any situation like this.

There's a lot of curiosity in the comments about what the right environment and role is. I share those questions, but I also think it's important to just feel into the situation more before moving to action.

Queerness I also know for me, in tech, reminded me of the idea - everyone has to learn the dominant paradigm, and then there's ours. Meaning, I do think I experience the world differently through queerness, and it was a navigation to own that and lean into its gifts, rather than just feel a sense of otherness. I don't know if that's part of your experience or not, but it felt worth sharing.

I have started offering coaching - if you'd like to just connect for an hour (no charge or anything, just connection) my email is in my profile. My instinct is it would just be good to drop into what you're saying and really feel through the layers of life situation, the creeping in fear, the aloneness, the stuckness, and see where forward might be in all of it...

In my experience, you are in learn more or earn mode, but usually not both, when working a startup job. The early stage startups offer great learning opportunities: you get to implement the first cut of the system and learn from your (inevitable) mistakes. The focus is on building. But there is no guarantee of earnings apart from the cash paycheck that is deposited into your account every pay cycle. In such a setup, you may run into bad personalities who can hamper your learning goals, in which case it's best to leave. Note that early-stage startups have a lot of risk and you may end up not learning anything while incurring the opportunity cost.

On the other hand, if you join a very mature startup or established public company, then there will be established HR processes and the likelihood of wacko personalities goes down. There will be better management and almost certainly better pay. The cost is that you will have a mediocre set of colleagues, far fewer learning opportunities and less relevant skills to pick up on the job (relevant, in the sense of landing your next opportunity).

Too much of one or the other will lead to what feels like constant failure. It may be best to alternate between these, accepting the reality that your skills need updating every now and then, and it's best to do that in an environment where that can happen quickly, and money is important and must come at the cost of work satisfaction and learning sometimes. Striking a balance between the two is the challenging part of career management.

EDIT: Reading your post again a few times, I also see another problem. It looks like you have trouble finishing up projects, i.e., converting prototypes into functional product and keeping it running. This is the boring part, and why people get paid the big bucks, and you need to learn the skill of finishing up and keeping the lights on. If you want to learn this specific skill, join a mid-size company that's growing nicely but has an established product or two in a big market. This type of company is where you will have opportunities to learn this type of skill.

Where is this “constant failure” you talk about? I’m seeing a normal engineer who keeps joining startups, and is living the startup life. In fact it sounds like you’ve even cashed out. I don’t see constant failure at all.

Startups are naturally chaotic. Most fail. Until they mature it’s complete chaos.

If you don’t like this life and it’s causing you stress, you should join a bigger, more mature company. It’s hard to tell from what you wrote if you like the fast pace of a startup or if you hate it. If you hate it and the uncertainty, then join a bigger company with more stable processes.

If you think that’s too boring and too slow, then keep joining startups but embrace uncertainty and chaos. There’s nothing wrong with either, but understand the nature of the company you’re joining and don’t have unrealistic expectations.

> How do I get over constant failure?

Constant failure? You are highly compensated and have a mortgage for a house, presumably in a very high cost of living area. It seems like you are an insecure overachiever and need to reframe things.

> My manager left a few weeks after I started, my onboarding buddy has been absent, and the fear has started creeping in again that I'm alone and can't hack it in this high performing team.

That doesn't sound like a high performing team. Stop putting dysfunctional startups on a pedestal and denigrating yourself.

This seems a normal, even successful career to me. You were just burned out and maybe had a mesiah complex. I never had these kind of problems because from the beginning I always had a very mentally checked out a la office space perspective on everything. You pay me for 8 hours of best efforts to untangle your ball of problems but nothing is ultimately my fault and at the same time I see very little of the overall success in the company so why should I care beyond not getting fired?

Two steps to success:

1. Set up a local development environment. (what I call "setting up shop")

2. Read the source. Understand all of it. Debug it. Take it to dinner. Read it at bedtime, coffee time, sexy time. Don't wait for "buddy" to come teach you.

If you are too tired/unmotivated/unable to do those things, just rethink your career. If you do those things, congrats you are a hacker so what exactly is the problem?

It sounds like you've been able to consistently land dev jobs, produce working software (it's not your responsibility to ensure the thing you've been asked to build is commercially viable), and build a good reputation (you mention good feedback and promotions), plus you've made a ton of money (most people make way less money than software engineers, and the average software engineer has not gotten a lucrative stock windfall). I think you've been very successful :)

> It's been a couple months and I have achieved nothing.

At my first software job it was said that a new hire typically wouldn't be a net positive for the team until they'd been there a year. You wouldn't necessarily have even been given a real task in the first two months, let alone gotten it shipped. Big companies have bureaucracy and gatekeeping (for good and bad reasons) and operate on timescales of months or years. By design, a new person can't unilaterally be productive. It's possible that investing the time to empower you to be productive just doesn't seem urgent to them right now - dealing with the fallout of a manager leaving may be much higher priority. You're on the payroll, they know you'll be around for them to utilize when they need you...

> If I can't work in the tech industry it would completely upend my entire life.

Based on what you've said, this fear sounds very unlikely to come about. Even if this company is dysfunctional and you need to move on, you have a history of being able to get tech jobs, and it sounds like you've made a positive impression on many coworkers in the past, so I imagine they'd vouch for you. And there's a ton of demand for developers right now, and a wide variety of companies to choose from!

Maybe move into sales if that is possible, very few people in sales are technical enough and let companies down, you however sound like might know enough to answer those board room sale pitches which require technical details. You can also then find out more about what the customer wants and then use that feedback to drive the technical direction of the product. By being able to code, you can randomly QA the product by getting customer feedback when you drop in on a customer and talk to their users (if that is possible), and you can then pass this feedback back to the dev team. Whilst off the shelf software is mass market, it doesnt always lead to lock ins, custom built software does lead to lock ins and that protects income streams for all.

Also write a bucket list and see how you can change your job to achieve your bucket list. Remote working means more office based employees like coders can now work whilst travelling the world.

that doesn’t really sound like constant failure to me, it just sounds like you changed jobs a few times. startups are inherently turbulent, a job at a bigger company might be less stressful.

The only person responsible for your health and happiness is you.

If you're pushing yourself to the brink of burnout and mental breakdowns, you aren't giving yourself enough time to recover. Period. Take it seriously because it can spiral out of control.

There's this thought that once you cross your threshold of a mental breakdown, you become fed up. That's usually what burnout manifests itself as. It seems like it's showing in your work where you aren't landing things based on your expectations. It could also be that we're in the middle of a great reshuffling and things aren't really stable anywhere. Who knows?

You are ultimately in control of your own destiny. To get over constant failure, you fail more. You fail until you succeed. You keep going. But you need to do this in a way that is sustainable so you can wake up every day to make an inch of progress rather than nothing at all.

You could take a risk, and tell the truth to a coworker, ideally someone who sees themselves as a potential mentor. It's an act of trust, being vulnerable like that. But it doesn't sound like you have much to lose, and it's a risk that could actually put you in a much better position, personally and professionally. 2 months without a PR merge isn't the worst thing in the world, but yeah, it's time to do something.

Someone else gave some good practical advice, about getting into a rhythm of merging smaller PRs. That can be a good confidence booster. However, that's not without its risks either, as coworkers are sometimes not terribly fond of trivial PRs.

I can speak from experience. I did join once to a team, that was really some levels above me. BUT basically the only thing that helps is to actually work on something. Just ask the team for work.

Of course the best would be for you to do something together with a senior. If there is someone who likes to help, this is your guy.

In my case I think they thought, that this would only slow them down and there wasn't a "nice helper" guy there. So I did my best. It wasn't really good, BUT it was something that could be worked on. After that a lot of help came from the team, because it was kind of useful and later a central component.

You sound like stress/self doubts are your biggest issue. There's plenty of people working in tech who are objectively not very good, but they get along winging it and pretending. Obviously, that shouldn't be your goal, but remember it as your safety net.

The secret of your high-performing people might simply be that they put in the work and spent 100+ hours reading the current codebase and, thus, they now know exactly where to change what. But they didn't start that way. They started out being unproductive and reading the source code base.

First: take it easy, a couple of months is nothing, and your boss left, so you’re kind of in limbo, that happens.

Second: talk to people. There is nothing wrong telling your coworkers / senior people how you feel. Just pull someone who seems senior and nice apart and tell them straight up: “hey Can I talk to you too ne sec. - I am a bit at a loss here, since my boss left I am not exactly sure what I am supposed to do, who do you think I should talk to to sort this out?”

I don't have advice for you, but you're not alone. Been coding for nearly 30 years, full-time professionally for 10, in startups and bigcos. On every team I've been on, I've been the sole expert in several technologies. Yet the most productive I've ever felt professionally was as an intern; it's all been downhill from there. Haven't merged a commit now in probably 8 months. And I have very little code that's running in production anywhere.

My career sounds similar but all at a large company. High performer initially. They wouldn't promote me, wouldn't give a modest raise, and then screwed me over a few times. It's been a downward spiral. I just don't care - even if I perform well I would probably get screwed like in the past.

My advice is to not care. If you get fired for work in tech for a non-tech larger company. It will be boring, but you'll get paid.

You just have to accept you can actually flip 10 heads in a roll when betting tails. I’d keep rolling given the chance if you don’t have another game to play

What I got from all this is that you are telling yourself that you want to do work that continuously causes you a great deal of distress. Why is that?

Thanks for asking, I'm in a similar situation and it's very useful to have more data about this :)

It should even be a page on big websites.

You say that you have been with a number of startups, and each time it seems like your expectation of what the work at a startup _should_ be like clashes with reality. I have a feeling that this clash plays a big part in your frustration.

It can be helpful to make hidden expectations explicit, and thus allow for a reality check.

So, in your opinion, what is the ideal startup like?

If you haven't done any pr for so long, what do you do?

Do you don't work in a Team?

Or aren't you building up a team or org?

Either it's your position to see issues and solve them for the org or it's your job to execute.

If you can't come up with things to do, but it's your job, you should search for a team or product and not for a company.

1. You have imposter syndrome (the “fear” you describe). The good news is, this is totally normal, most people have it and it never goes away. You just have to ignore it and eventually you will get good at ignoring it.

The proof of this is that you describe being worried that you can’t work in tech, yet clearly have managed to get several tech jobs and so far (as far as you described) have not been fired or even laid off. So you objectively can work in tech and should just stop listing to the internal voice that says you can’t.

2. Consider that “tech” is not a monolithic culture, and it’s entirely possible (especially at earlier stage startups, but even at FANG) to have several unlucky experiences in a row.

3. You current job situation is unfortunate, but once you relax and ignore the fear of failure, it’s still a pretty good situation. You have a job at a company you’re excited about working with people you respect. So far you haven’t been fired or put on a performance plan. If the company is unhappy with your output it is up to them to tell you, and you shouldn’t decide you are a failure before they do so.

You didn’t say anything about your new manager, but you should ask them what is a priority for you to work on, and focus on shipping something (anything) aligned with that priority. One project at a time. Don’t spread yourself too thin, or give up on the project because you can’t find someone to approve the PR. Have a singular focus and keep knocking down doors until you finish it.

4. You need to learn to live with setbacks in life and your career. The best way to do this is to get a hobby (outside of work/tech) that is easy to succeed at, such as exercise. E.g. to succeed at running or cycling you just have to put one foot in front of the other, and leave the house a few times per week. This can do wonders to take your mind off professional setbacks.

5. (Edit after reading some of your other comments in the thread) Stop comparing yourself to others (and possibly take a break from social media, especially LinkedIn, if that is the source of your comparisons). There are always going to be people massively more successful in life. Even if you get promoted and write a book and found a startup there are still going to be people way more successful than you and you will still feel like a failure if you constantly compare yourself to them. Also, lots of those people who present themselves as super successful and happy on social media are actually deeply unhappy. That is not your goal.

PS. Happy to DM or chat about specifics if you want to reach out (email in profile).

Honestly there is not enough details about the companies that you could get valid feedback on this. An internet forum is not the right place for this. You need to chat with someone in confidence and tell all the details.

I dont under stand how you can be there for months and not have a single PR. Are they not approving them or you haven't been assigned any work? What's your day to day like?

Whenever I get in this kind of funk, I notice that the more energy I put into it... the more it grows. What always gets me out of it is to stop focusing on my feelings and start focusing on what others need from me.

This is made much easier when you have a supportive team at a company which truly has a learning culture (heuristic: look for founder-led companies which haven't taken outside investment and have sustained growth). The fact your manager left and you have a total absence of feedback sucks. It's very easy to doubt in that situation.

It's entirely possible for an individual contributor to communicate everything right, implement well, conduct everything professionally and STILL have everything blow up. Normally the advice here is "truly great IC's account for environments/problem selection" as well. While true, this also feels a little...cruel? Uh, dismissive? I don't know how to characterize it.

Assessing the state of a business and whether you can fit into it well is a skill which must be learned. You're not gonna be good at it at first. And it sounds like, for you, this may be the key skill to work on. Can you distinguish between what's truly your fault, and what's a product of the environment you're in? You say label it a dream job but... is it? You're certainly going to know more about a place once you're working there than before you've joined.

The hardest part of distinguishing is typically actually admitting to yourself that some aspects are out of your control. At least this was for me... at one point I built something truly great for a business who didn't deserve it. That's when I learned (the hard way) my execution is necessary for, but independent of, the success of the business.

Ignore the fear. Don't feed the FUD. But do be honest with yourself about where you are, and what you're doing. Is it really all you? (really?) Learning in this way is typically expending energy to rid yourself of illusions and scripts which no longer serve you.

For where you're at right now, I also suggest you imagine for a second what someone up the org chart would want to see out of the best version of you. This means you're going to need to approach someone in the company with your vulnerability. But also come with something to offer (a plan, an idea, a direction). Consider this a litmus for them as well as for you. If you put in a good faith effort and they cruelly discard it, time to move one. If they don't, they really listen, and they put in effort too.. maybe there are problems you weren't aware of. Problems you can help with.

Good luck. Don't be too hard on yourself. But don't be too nice on yourself either! ;)

Sounds like you hit the lottery with that one startup and got promoted to a level far above your competence. Common problem. Truly senior people and true startup people do not struggle to find projects and contribute PRs. Find a job at an appropriately junior level at a real company. (FAANG will downlevel you appropriately.) Learn some real skills then try the startup thing again in a few years if you want.

Maybe move beyond startups to more stable organizations doing meaningful product development.

"Real privilege lies in knowing that you are enough." - Nipun Mehta

Normally CTO coach but if you drop me a line we could chat.

You have some self-imposed stench of failure. You’re failing because you expect to fail. Change your perspective. You can do this.

no one can deny or take your personal projects away from you. it's a good defense.