Ask HN: What should I do now as a middle aged developer feeling like a loser?

If you're going to optimize for money, optimize for money. I optimized for money for years and have no regrets. I'm now enjoying the fruits of that choice living in Asia and the amount of effort sacrificed was totally worth it.

You have a wife and kids now, I would heavily advise against E. (From the tone of your post it looks like you know this). This is what I do now, but I'm currently not optimizing for money.

C is doable. One leetcode question a day for five months then one month of hardcore interviewing will get you there without much sacrifice for family life. You can find that extra hour in your day by waking up an hour early. Remember, we're optimizing for money here, not short term happiness, if you feel frustrated every day trying to re-learn how to reverse a linked list, remind yourself that's the _correct_ feeling to have and it means you're moving closer towards your goal. The end result is a better life for your family.

D is basically C, except without doing one leetcode question a day. You still need to do a 1-2 months of hardcore interviewing. 80% of the effort for 1/2 of the results is a bad trade.

However, if you're _not_ optimizing for money, there's option F: move somewhere cheaper and work get a remote gig. I'm currently in Taipei and am friends with a lot of people who've made this decision. Some with families, some without, some single. The main thing we had in common was we valued autonomy over everything else. I have other friends who stayed in Canada/USA because they value extended family over autonomy, and that's OK too!

This sounds cheesy, but if you haven't already write down your 4-7 core values then make decisions based on those. Making decisions that align with my values has reduced my anxiety drastically.

Good brutally honest logical take. Did you optimize for money to save up, then move to cheap col in Taiwan, and now changed to prioritize autonomy?

I realized after going through that seemingly cheesy core value exercise that I'd always been optimizing for autonomy, I was just using money as the proxy.

I was trying to optimize to get a green card (I'm Canadian) "quickly" and took a job that promised to help me but didn't deliver. Looking back, I shouldn't have been in such a rush to find a shortcut and just grinded leetcode longer. The whole time I was saving money because my end goal was to go full American Dream and start a business after I got a green card. It all worked in the end though because it lead me to where I am now.

As for moving to Taipei, when the green card fell through I started _really_ doing the leetcode grind because my friends at FAANG companies told me how much better of a job they did for immigration. While I was doing that I decided to interview at some startups for "practice" and ended up getting an offer to move to Taipei (CEO split his time between Hong Kong and Taipei). I'd been learning Chinese for a couple of years and always wanted to check out Asia. Taiwan had zero COVID cases (not exaggerating, literally zero domestic cases for most of 2020/2021) and I was getting no benefit paying Los Angeles rent and not being able to meet new people in person.

It wasn't until about 8 months into the startup job I realized just how affordable Taipei was, and it sunk in I didn't need to keep a job for immigration anymore (Taiwan has a Gold Card visa that's super easy to get and isn't tied to employment like the USA). That's when I decided to go all in taking Chinese lessons every day and starting an engineering training business in the afternoons/evenings. I gave my last job one month notice to not burn any bridges and now I'm on my own.

If you anyone wants to move, I highly recommend not worrying too much about the money and just finding a job and moving. Having some income lined up before you go is nice, even if it's just beer money teaching English. If you're indifferent about the money I recommend at least signing up for a language school so you have a routine you can follow during the week while your friends are at work.

Sounds like a nice little journey and good old mixing it up. Putting the effort in to learning the language is definitely key.

Thank you, this is really helpful. At this point in my life, I should optimize for money.

> but if you haven't already write down your 4-7 core values then make decisions based on those. Making decisions that align with my values has reduced my anxiety drastically.

This is great advise. I will definitely do it. I sort of have some idea about my values, like I value autonomy, creativity, family, and comfortable lifestyle. But I really need to sit down and think hard what is the most important value to me.

This helped me a lot too: https://tim.blog/wp-content/uploads/2013/04/dreamline.pdf basically you write down exactly the lifestyle you want, figure out how much it will cost per month and work your way backwards to get that number. It's usually cheaper than you think.

Just from reading "I value autonomy, creativity, family, and comfortable lifestyle." without any other context tells me a 9-5pm gig at Google (including leaving at 4pm on the odd Friday to see your kid's dance recital) sounds like a good fit.

I'm the weirdo who'll take revenue splits and equity deals, roll the dice on random startups, and move somewhere where I'm completely illiterate. If you leaned towards that though, you'd probably have a post asking how you could get a job at crypto company in Signapore :)

You’re thinking about this the wrong way. Start thinking about how to do with less. A bigger house won’t make you happier, it’ll just take more money to maintain, and therefore more of your time. The more you work, the less time you have with your family. You feel like a loser because, somewhere inside you know you’re the sucker. Stop consuming so much. Stop wanting more. Think of ways to maximize what you have by minimizing the time you spend working. Maybe downsize that house. Maybe move somewhere else with a lower cost of living and work remote.

Def agree, but optimize in both directions. There's only so much defense (lifestyle reductions) you can play, but you can go unlimited in offense.

You gotta be honest with yourself, know yourself, know your goals, etc and then base your consumption and lifestyle aspirations around that. Maybe a super cozy and minimal but efficient house is exactly what you need. Maybe you want the ranch with acres of land to explore etc.

You are right, a bigger house won't necessarily make us happy.

TBH, we can still get our dream home, banks said we can get huge mortgage but I am not comfortable with it. Roughly banks will loan you upto 3x of your annual income. I have prefer limit of 2x.

We feel disappointed that we cannot buy our dream home while staying within our limits but it sort of reminds me that I have fallen behind. I know it is a rat race but makes me wonder what would happen in 20 years from now. Will I be able to send my kids to college? Will I be able to retire if I don't participate in rat race.

It is only a rat race for you if you decide to join the race. Who is it that is putting pressure on you to make more $? Is it your wife? Your friends? Yourself? Whoever it is will never be satisfied no matter how much $ you make. Stop comparing yourself to others. Ask yourself what you want deep down and act accordingly. When was the last time you were truly happy without buying something? Focus on that. It is your subconscious ego telling you something. Listen to it.

I just wanted to say that's really great advice!

I’ve built 14 startup companies over my career, currently on the 15th. Out of those 9 were acquired, and 3 were IPO.

Yet I’m not what you’d describe as rich because of the asymmetry of risk vs rewards, and because of the drag of taxation. Outsized rewards are possibly only if you take outsized risks. When you have a big return, a large percentage of it is taken by the government. This is an additional hurdle over the risk you took. The result is that you take all the risk, and the government shares in the reward.

To break out to a level where you can support yourself and your family purely through requires a true outlier 10x-20x the average return. You can wait a long time, your entire life in fact, to have this kind of outlier.

I’ve sacrificed the best years of my life taking outsized risks and chasing the carrot so to speak. I’ve done well enough to maybe stop working in the next couple of years by age 45. My body kept the score of all the stress and my health paid a heavy price.

The time you have as a healthy person can never be replaced. The trick is to stop spending your time chasing dollars. Let other people take the big risks and get the big rewards, while you sit back and collect a tax of sorts.

The best way to do this is to own a business, which minimizes your tax liabilities, and also minimizes your time investment. This means you have to choose the business very carefully. It should be something that is very low risk, something which allows you to hire labor from the middle and bottom of the bell curve. It should have minimal regulation and licensure required to operate. Likely, it will be completely outside your high tech expertise. That’s good, that’s what you want. You’ll have to learn to operate this kind of business successfully.

By reducing your lifestyle, by not going into debt for anything, by not buying that big house, new car, new computer, etc, and by saving your income, you will be able to afford to buy an existing business like this in cash.

After you’ve mastered the operations and cash flow of one business, you can proceed to buy another.

The richest people I know, both in terms of net worth, but more importantly their time, operate in this fashion. My neighbor owns 38 McDonald’s franchises. He started with a laundromat.

The high tech gambit is a sucker’s game. I know, because I’m the sucker. The answer you are looking for is not “work harder”, or “go into management”. The answer is… stop working! Gradually your dependency on your working income until it’s gone.

I love this.

I agree that owning a business that doesn't require too much of your time is better than a business like consulting. This might be something I would do on the side. One of my old manager owned several rental properties, it rarely took any of his time.

Rental properties can be great, but beware they are high risk, not low risk. Properties come with many inherent risks you can sometimes assess before purchase, but they also come with hidden risks, not the least of which is the tenants. I used to own many rental properties. In one, a neighbors contractor sawed into the water main of the high rise, flooding over 200 units below. In another, a gas furnace cracked in the winter, and poisoned the tenants with carbon monoxide. In another, a layer cake of black mold grew 6 inches thick and had to be remediated for tens of thousands. In another, a contractor moved a pile of dirt and triggered 5 years of litigation and 100s of thousands in legal fees.

Better to rent properties for monetizing, insure your risks, and let others bear the big risks. I have a friend who owns timeshares and rents them on Airbnb, thereby avoiding most of these risks. Always look at what is possible in terms of risks. The worst will happen, it’s only a matter of time.

There is so much to unpack here I wouldn't even know where to start. First off, you think you're having a mental health crisis so you're going to HN for advice? Now on to you're specific scenarios....

A. "Aggressively move into management" Why do you even think this is an option? Do you really think the only reason you haven't gone into management is because you haven't decided to claim the seat that they've got just sitting there waiting for you? Management is a hierarchy so by definition there are fewer and fewer seats the higher you go up. If you want one you're going to have to beat someone else out for it. "The cons might be too much politics. People skills don't expire though" So you already think the only problem with management is "politics"? You're already starting out with a contemptuous attitude towards management that comes out in later statements.

B. Again, so you're so good at what you do that you can just decide to become a thought leader. It seems like you're assuming you're brilliant and the only ting that has held you back from being a thought leader is that you haven't applied yourself to the task but once you do success is certain. This doesn't jibe with your statement that you think you're a failure.

C. "I could easily make 2x - 3x my salary [at a FAANG]" You're going to get a job at a FAANG that easily? and get a 2x-3x salary bump for doing it. If it was that easy why the hell aren't you doing that now? LeetCode is what's holding you back? You don't want to take time away from your family, perfectly reasonable choice, but then you can't easily get a new job at a FAANG.

D. Again, you can just walk in anywhere AND get a salary bump? Again why aren't you doing that already. It's kind of the no brainer solution which wouldn't preclude any of the other options and you're not even leaning towards this one.

E. This is just pure fantasy.

If your day job is soul-sucking then at the very least go with option D, take your 1.2x to 1.6x salary bump and reassess.

Thank you for honest and brutal feedback.

> First off, you think you're having a mental health crisis so you're going to HN for advice?

I have seen a lot of these posts on HN and gained a lot of value from other people's experiences suggestions. Last night I went to bed feeling lost, but writing out this post and then reading reviews been really helpful. Yes a professional can help with mental health issues better than internet strangers but this is what I have for now. I will contemplate a bit more but I think I am close to seeing clear choice for me.

> A. "Aggressively move into management" Why do you even think this is an option?

I have seen many "I will never be a manager"-developers becoming managers, directors, VPs, both in smaller and larger companies. I think it is a skill that one can develop. One of my friend is a senior director at a 5000+ people company. He has been telling me I have natural leadership skills and I should move into management. Also I have held team lead roles several times, I also enjoyed mentoring junior developers. As a manager my biggest weakness would be project/time management.

>. Again, so you're so good at what you do that you can just decide to become a thought leader.

Doesn't hard work make you good at what you do? Thought leader is a loaded term. It is company lingo. I guess what I really should have said I should work on internal Individual Contributor track. The final stage of our IC track is basically thought-leader.

As for feeling like failure, I failed in my side projects and ignored my career. And really feeling depressed that our dream home that was so attainable is complete out of reach now. Anyways, if I really focus on my career, I think I have a good shot of having a successful career.

> C. "I could easily make 2x - 3x my salary [at a FAANG]" If it was that easy why the hell aren't you doing that now?

Because I was not focused on money until now. I was happy and comfortable. I had a few interviews where I went in with a little Leetcode practice and I failed them horribly.

> D. Again, you can just walk in anywhere AND get a salary bump? Again why aren't you doing that already.

Again I was mostly happy and honestly I don't know if 1.6x bump in salary is worth giving up the comfortable job and the potential to move within my current tech giant.

And thanks for pointing this out. More I think about it, this won't be worth it.

> E. This is just pure fantasy

I forgot who but someone said ask yourself what would you do if you were not afraid. Then do that thing. I guess this is what I would do. Having a family makes it harder.

> If your day job is soul-sucking then at the very least go with option D, take your 1.2x to 1.6x salary bump and reassess.

I think you can change your mindset and turn subjectively bad things in to positive things. Now option D doesn't seem worth it. I rather try to go in management than get a small pay raise in another company and start over.

You’re very welcome. If you think that’s brutal just wait until you step out of that bubble you’re living in. Your entire list is, “do I want to make more money or a lot more money”. You seem to exhibit very little self awareness.

He said FAANG would easily increase his salary 2-3x, which probably is the case if he is making sub $150k. He never said getting into FAANG would be easy.

Yeah I am exactly at $150K.

>A. Keep the day job, and aggressively move into management. Safe and I know internal politics. The cons might be too much politics. People skills don't expire though.

This.

Play the "Game", take home a safe and regular paycheck, keep strict office hours, tune out after work to focus on Family and if you want to stretch yourself do Freelancing/Something on the side.

Thank you, I am leaning hard on this choice.

To elaborate on my above comment ...

Remember the fine balance between Idealism and Pragmatism. Given the current state of the World/Economy, taking unnecessary Risks when you have a Family dependent on you is absolutely not worth it. "Safety First" should be your current motto. Don't listen to rah-rah/gung-ho/YOLO folks and ruin what you have now. The proverb "A bird in the hand is worth two in the bush" is more relevant now than ever.

That said, staying in your current company and trying to move up the Management Ladder will come with its own challenges. Confidence is good but not Recklessness nor Foolhardiness. As others have pointed out it will not be easy but Persistence, Hard-work and some "Smarts" will see you through. "Stick it out", "Don't rock the Boat" and you will be good.

Good Luck!

Thank you, this is what I decided to pursue. It makes a lot of sense.

Have you considered not wanting a bigger house?

F. Get a remote position and move to a low cost & decent area. You’ll probably afford to buy a mansion with your salary with plenty left to truly focus on the family.

I would also work on some version of (b) and (e)

This is an excellent choice, my current job is already remote. We are stuck in our current general area due to school for 2 years or so. After 2 years, we can move to country if things don't change.

Schools are absolutely a big consideration. I live in central Louisiana (schools are ok, not great). I made the move 15 years ago - sorta forced into it, thanks to hurricane Katrina, but it has grown in me. Remote jobs weren't a thing then so I started my own company!

I cannot imagine being in the rat race of big cities ever again.

First, I want to say thank you to everyone who responded. I really liked what jameshush said about writing down my top values. After some thought, I think my top values are:

1. Kids - I will not do any job or business that will negatively impact our time.

2. Autonomy/freedom - In long run, I rather have more autonomy than money.

3. Money - This is not to say that money is not important to me but rather it is one of top 3 things I value. In short term, I need to optimize for money.

After thinking about my values and reading comments here, my plan is to combination of option A and C.

At my current company, I will start conversations with my management about moving up the ladder. And do whatever they suggest. This may take several months before they actually promote me to any leadership position, if they do. I have a lot of freedom at my current company, like I can run errands during day and catch up on work later etc. It is safe and there is possibility that in a couple of years, my salary can be close to FAANG engineers.

At the same time, I will do 30 mins of Leetcode/interview prep daily. This way if things don't workout, I will have something to fallback on. I will not stick with my company for vague promises of more money in future. If they don't offer me any concrete plan for my career progression, I will jump the boat as soon as I am ready for FAANG interviews.

> We need a bigger house, but we cannot afford it. We could have bought our dream home in 2020 but prices have skyrocketed in my area.

Have you considered moving to an area with a lower cost of living? You said you're at a major tech company. As far as I know, pretty much all of them are providing an option to work remotely and even locate out of state (assuming you're in the US).

> I am leaning towards option A or option E. What do you think?

What is your main motivation? You mentioned affording a bigger home. Is money the main issue? Do you enjoy the work you do? Do you want to work on other projects and maybe not what you're working on in your current team?

> A. Keep the day job, and aggressively move into management. Safe and I know internal politics. The cons might be too much politics. People skills don't expire though.

Based on the information you gave us in the post, this is a serious red flag. Being a manager is not easier than being an IC. As a matter of fact, the blast radius of performing "poorly" or being ineffective is much higher. You're not just going to let yourself down (assuming you even care), but you're potentially going to damage other peoples' careers. As a manager, not only will you work on roadmaps, but you're responsible for hiring and coaching your team. You need to identify their strengths and growth areas. You need to give them real opportunities, and you need to help motivate them.

If your focus is your side projects, this is train wreck waiting to happen.

Good points. Unfortunately, relocation is not an options for us due to extended family.

> What is your main motivation? You mentioned affording a bigger home. Is money the main issue? Do you enjoy the work you do? Do you want to work on other projects and maybe not what you're working on in your current team?

Money seems to be main issue. I love programming and didn't mind dead-end job as I was programming, at work and after work. I would love to stay programmer and make FAANG salaries but having tough time with Leetcode.

> If your focus is your side projects, this is train wreck waiting to happen.

No, side projects are over. As a parent, I cannot do it without taking time away from my kids. If I go in management, I will be all in. Blast radius is bigger but I hope I can be effective manager.

E is dumb, d is pretty manageable but the cowards way out and c is the right answer. You are undoubtedly capable of working these jobs just for whatever reason you seem unwilling to grind out the interviews. Yep it sucks, and it takes a long time and it's hard but it's going to be life changing for you, and your family. So suck it up,put in the work and go get a job that pays what you are worth.

I'm of the same age, two kids as well. Totally normal to feel this way, so don't beat yourself up. Why not stick with B and then move to A down the road? Why give yourself the added stress right now? If you are at a major tech company, there should be room to move within the organization later on down the road as well. Also, don't worry about the careers of others, everyone moves through their careers at different rates.

On a side note, every job is going to have its soul-sucking aspects, no matter how amazing the position might look from the outside. Politics, stress, anxiety, etc are going to happen whenever people and emotions come together. Time with your kids is something you won't ever get back, maximize for this before anything else (especially since you seem to already have a good career). Separate the job from your life as much as possible, don't become your job so to speak. The time for side projects will come back. When I do get the time to work on a side project now, I find it much more enjoyable and I appreciate the slowness.

Thank you, love it that you said maximize time for kids. It puts everything in perspective. Only reason I started to compare myself with others is because we got priced out of housing marketing when we could have bought our dream home just 12 months ago.

Otherwise, while I didn't care so much about my job, I was mostly happy.

Same thing happened to me (east coast), was looking to upgrade to a single family home but pandemic bumped up the housing prices and demand. I spoke to a realtor while out on a walk one day who mentioned that houses were selling at $80K+ above asking price and to just sit tight for a bit. So that's what we'll do...I'm not in any rush. What can you do anyway? No sense in paying inflated prices.

Yeah I am Texas. Before 2021, one could buy a beautiful home with a pool in a top rated school districts for $450K easily. Now same homes are going for $650K+.

I personally am not in rush to buy new home but it just made me feel like I didn't keep up with inflation and should do something about it. Wife is in slightly more rush but I am very strict on our loans to income ratio.

Keep in mind that E can occupy your mind a bit more than A. Im not a management type, but if you feel good about it go for it. As for l33t code just read couple of books, clean code, design patterns and pragmatic programmer. If you like to code choose a nice framework and get great with it. I understand its hard with kids, but think about it in diff perspective. If sacrificing one hour per day to learn new, well paid tech can get you to make same money or better money in just 4 days instead of 5 in one year, then maybe its worth it? Thats ethernal trade off. Putting more effort when its hard to enjoy early retirement. And keep in mind theres not that many joba where you can work from home and take care of your kids. Devs and it people (not the printer guys) are extremely privilleged we must admit it.

I recently found "D - Find a new job in my field" was effective for increasing my salary, reframing my outlook on life, and getting my swagger back.

Was your field specific? Or just like a generalist java job etc.

Def good to change it up when things get stale.

My field is not all that specific, but experience is how you sell it.

In my case I have 5 years of experience working on ETL processes (SSIS) and 10 years of SQL either troubleshooting said ETL or writing aggregated reports.

Now I could be down on myself and say "I only use C# occasionally for troubleshooting or glue code", or I could sell my experience and point out that I designed and delivered reliable solves to complicated customer requests. Often those ran reliably for years. Usually they were "boring" SQL solutions, but hey, use the right tool for the job.

Another option, that is simpler to manage is to get rid of items, junk, gear, objects, etc; you'll get plenty more space.

Improve the space you already have.

Are you using the room where you sleep or is it just used to sleep? Do you have a garden? Maybe build a small office space there? Do you have a big bathroom? Make it smaller? Do you have a garage? Park outside, use it for something else?

There are beds you can transform into something else or save space, etc

Oh yes, we are working hard to optimize current space. But I think the real issue is 12 months ago we could have bought any home in any of nice middle class neighborhoods. Now homes are so expensive for us. This made me start comparing my career with some of my friends.

I don't even care for a bigger home but my kids ask for backyard. That is what kills me.

Getting a bigger house will not solve anything. You are chasing the wrong goal. I recommend getting therapy so that you can find out what is really going on. If you have enough money to have a home, food, health etc. but are still unhappy then it is not materialistic things that is the problem.

A - could be good depending on the timeline

D - even 1.2-1.6x is a pretty good raise, depending on what you make now. If you own your current house, that salary increase may be enough to afford a bigger place. May even be the option requiring the least amount of effort/extra time.

C. and take time from your current job to do the LeetCode. You want to leave anyway and there is high chance nobody even notices you work little less.

Also, FAANG companies are really big, there are a lot of teams with a good work-life balance.

I'm a mid-level loser with a family. Just coast in your current job.

Just about any house is big enough for a family of 4.

Can you relocate? Easiest way to save money on taxes and buy a bigger house.