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Ask HN: Dream Job or career suicide?

Ask HN: Dream Job or career suicide? For the last two years I have worked remotely for a someone who is trying to convince a financial services company (of about 20 employees) to build a replacement for their existing (dated) software platform. We've been building free prototypes/demos for the last two years. During this time I have been the sole developer. Overall my job is great. I get along well with my boss, there are no hard deadlines, my hours are 100% flexible, and the work is techincally interesting and low pressure. The pay is a bit below the going rate. The problem is that I've slowly become convinced that it is very unlikely that we will actually get a contract with the financial services company. Additionally, my boss wants extremely technically complex features (like a time traveling database) in the prototype application without having any indication that the company actually wants those features. The application is his baby so feature X, Y, and Z are critical. The financial services company also commented in a meeting that his cost estimate was less than 10 percent of what they expected. So basically he is trying to sell the Sun, the Moon, and the Stars to them for dirt cheap. I have very little experience in custom software sales but it seems to me that eventually the project is going to fizzle (no sale) or turn into a huge mess (a sale but an eventual trainwreck when actual expenses collide with requirements). In the meantime, my work conditions are great. My question is: Is it terrible for my resume to work for years on a project that never sees the light of day? Or should I stop worrying and just be happy that right now I have a relaxed work environment?

ilamont 9y ago
How is your boss funding this project, prior to signing up customers? Do you have an equity stake, vested or otherwise?
- throwaway23094 9y ago
  I don't know how he is funding it. As far as I know, he has no existing business revenue streams. It seems like he is paying me out of his own pocket. I don't have any equity.
savethefuture 9y ago
Are you getting paid for your work? You mentioned "free prototypes". You could always just write on your resume that you worked for "X Company", and then give details about the project you worked on, whether or not it sees the light of day is irrelevant. Employers want to see that you can work/code/do your job, not if past projects were a success or not.
- throwaway23094 9y ago
  My boss is paying me. The financial services company hasn't paid my boss for anything. Hence the "free" part. Thanks for your thoughts.
mattbgates 9y ago
I've been building software myself and while I haven't officially started to sell anything yet, I must say, what I've gained in experience far exceeds whether the products I created are going to sell or not. I started out knowing almost nothing and just a year later, I can build just about anything with PHP and MySQL. So there is no waste there. However, "selling dirt cheap" isn't always the way to go. Most companies think: "You get what you pay for" and that may be a mistake on your partner's part. Underpricing a product might seem great in order to beat the competition, but when it comes to companies and profitability: they want results and profits. They don't care how much it costs to get that. They will pay tens of thousands of dollars to have software that is reliable and suits their exact needs. When the client lets you know they expect to be paying more: it usually means they are going to probably have some demands for customization. He wants the clients, but then they will likely ask for custom features or not be happy with something, and.. it may just be a never-ending story, and there is going to be a time where you both have to just say no.. and take the hits and negative reviews. OR.. say yes, but it is best to charge enough to stay in business and even hire additional employees. I have undercharged clients before... many times and many mistakes.. and after a while, when is it no longer worth it? When will you just bite the bullet and take the hit because.. you didn't ask for enough money to be worth maintaining the project. Even if your project doesn't see the light of day, but you have the source code, and it can be seen somewhere, I'm sure its not career suicide. What you have probably learned is more amazing and useful. BUT... he may be thinking smaller or just not reaching the right audience, and you may need to be the one to advise him of a different method, whether he wants to hear it or not. Both of you want the same thing: A Saas in which you are both making good money and developing software as a business.
- throwaway23094 9y ago
  Thank you for your thoughts. I certainly have learned a lot - although I had learned how to build full stack applications before I started working for him. Just to be clear - he's not my partner, he's my client. So I don't have any rights to the source code. Also, we're building a custom software solution for a business and not a Saas product.
  - 9y ago
meric 9y ago
The OP's comments are dead on this thread. If you want to interact with the OP, turn on showdead on your profile.
- throwaway23094 9y ago
  Thanks for the comment. I suppose that is because I'm posting from a throwaway account.
- livingparadox 9y ago
  The entire account is marked dead. I had to "vouch" for the submission to get this thread to show in the first place. I'm not sure why they were hellbanned as this is the only submission and its very much a valid "Ask HN post".
philbo 9y ago
Invariably for questions like this, I think the answer is that you need to go out and see what else is available. Get your resumé up to date, send it to organisations that interest you, attend interviews. Just going through that process should help you understand where you want/need to be. When you get offers for alternative positions and have met the teams that you could be working with, then you'll know whether you should stay or leave.
DrNuke 9y ago
Until you get paid, all is good. As soon as reality (no customers) bites into your employer and he starts acting the colors of a failed business, politely jump ship and goodbye.
gargravarr 9y ago
If you're working with tech you like and you're earning a comfortable wage, I would say to carry on as long as you like, especially with an unstressed working environment. The trouble, and you seem to be very aware of it, is that everything could change at the drop of a hat - if the deal finally falls through or the costs spiral out of control, you could wind up in a nightmare. Keep options open. If you're working with good tech (which from the sounds of the software you're writing, you are), then the skills are transferrable and you ought to be able to move to a new job with little warning. As for the resume, it's great to see a respectable length of time at the same firm (because it shows dedication), and whether or not the project ever came to fruition is irrelevant to a new employer - that's on the people (person) above you. You're the person building it, you know the code and the tech, you're the one who makes things work. That's what to emphasise in your job search. I can totally understand your desire to remain in a non-stressed work environment, but it would be worth worrying just a little about your future and keeping a close eye on the market. Always keep something available. As much as you may feel loyalty to your current boss, you have to be responsible for your own career and personal state, and if (or when) everything comes crashing down, you can tell him you appreciated the opportunity he gave you, but you must look out for yourself. Don't let him drag you down with him; if his business decisions turn out to be wrong, it's his responsibility, not yours. At the same time, you can try to have a serious conversation about his approach. Lay out your concerns that you, as the author of this project, are not going to see your efforts bear fruit if the customer bails or he drastically underprices it; it begs the question, if he's priced it so low, what source of income is he using to pay you? Personal funds? Those will run out eventually. Tell him that if his business is to have hope of turning a profit, he needs to charge realistic amounts, especially if the customer can be pursuaded to pay more. After all, some businesses (particularly in the financial sector) will stick to a 'get what you pay for' mindset, and will not be convinced to buy a cheap system no matter how fancy the features are, because they will see it as low quality or unsupportable (the latter is a good possibility when they realise what they actually do need). In short, try to get your boss to see sense, but carry on as long as you're comfortable, and be ready to change jobs if the wheels start coming off.
dtnewman 9y ago
If you are worried about the possibility of losing your job and having to do without a salary, then you should start looking now. But from the way you asked your question, it seems like you are aware of this possibility and you are more worried about how this will affect your long-term career. My 2 cents is that in future interviews, it's very unlikely anyone will ask or care about the success of the project. They care about your technical skills and it sounds like this job is good from that aspect. You should be able to spin this in a positive light.
amorphid 9y ago
>> Is it terrible for my resume to work for years on a project that never sees the light of day? As a former recruiter turned engineer, I can say that you shouldn't worry too much about it. If there were a surplus of great engineers fighting for table scraps, I might offer different advice. You may find it mildly harder to break into gigs that want more experience working on a fast paced agile team, but the reality is that you'll always have a mildly harder problem breaking into something that asks for experience you haven't been practicing recently. What I'd be more concerned about is working on tech that is too crusty. If you're programming in MUMPS, using flat files as a relational database, and hosting everything on Windows 3.0 being emulated on OS/2, you may wish to revisit your tech stack. If you can't throw any not-stale tech into the keyword soup on your resume, it'll look like you haven't been motivated enough to keep your skills sharp. Disregard this advice if you have plenty of people trying to recruit you and/or you know people who'd hire you if they could.
hkarthik 9y ago
As an eng manager in SF, I'll form the dissenting opinion here. Get out now. Products need to ship and go somewhere. You only now what works in terms of your tech stack by dealing with the fires of actual production traffic. Lots of teams end up focusing on the wrong thing and building a product no one uses. It's totally okay for this to go on for a year. Going on for two years is a huge red flag and it might make you unemployable at a company that has a real product. Get out as soon as possible.
- tedmiston 9y ago
  Eh. Plenty of product is private. I worked for a few years on tech inside a military research lab where neither the product nor code will ever be seen by the greater public, but that doesn't change the learning that took place. It's not a concern to me or anyone familiar with an industry like that.
JSeymourATL 9y ago
> the work is techincally interesting and low pressure. What are you learning? What are the big problems in your field? How is this role stretching you professionally? Relative to career suicide vs vitality-- one should be continually adding and building skills that will be in demand. Richard Hamming offers briliant food for thought on your career > https://www.youtube.com/watch?v=a1zDuOPkMSw https://www.youtube.com/watch?v=a1zDuOPkMSw

ilamont 9y ago

How is your boss funding this project, prior to signing up customers? Do you have an equity stake, vested or otherwise?

throwaway23094 9y ago
I don't know how he is funding it. As far as I know, he has no existing business revenue streams. It seems like he is paying me out of his own pocket. I don't have any equity.

savethefuture 9y ago

Are you getting paid for your work? You mentioned "free prototypes". You could always just write on your resume that you worked for "X Company", and then give details about the project you worked on, whether or not it sees the light of day is irrelevant. Employers want to see that you can work/code/do your job, not if past projects were a success or not.

throwaway23094 9y ago
My boss is paying me. The financial services company hasn't paid my boss for anything. Hence the "free" part. Thanks for your thoughts.

mattbgates 9y ago

I've been building software myself and while I haven't officially started to sell anything yet, I must say, what I've gained in experience far exceeds whether the products I created are going to sell or not. I started out knowing almost nothing and just a year later, I can build just about anything with PHP and MySQL. So there is no waste there. However, "selling dirt cheap" isn't always the way to go. Most companies think: "You get what you pay for" and that may be a mistake on your partner's part. Underpricing a product might seem great in order to beat the competition, but when it comes to companies and profitability: they want results and profits. They don't care how much it costs to get that. They will pay tens of thousands of dollars to have software that is reliable and suits their exact needs. When the client lets you know they expect to be paying more: it usually means they are going to probably have some demands for customization. He wants the clients, but then they will likely ask for custom features or not be happy with something, and.. it may just be a never-ending story, and there is going to be a time where you both have to just say no.. and take the hits and negative reviews. OR.. say yes, but it is best to charge enough to stay in business and even hire additional employees. I have undercharged clients before... many times and many mistakes.. and after a while, when is it no longer worth it? When will you just bite the bullet and take the hit because.. you didn't ask for enough money to be worth maintaining the project. Even if your project doesn't see the light of day, but you have the source code, and it can be seen somewhere, I'm sure its not career suicide. What you have probably learned is more amazing and useful. BUT... he may be thinking smaller or just not reaching the right audience, and you may need to be the one to advise him of a different method, whether he wants to hear it or not. Both of you want the same thing: A Saas in which you are both making good money and developing software as a business.

throwaway23094 9y ago
Thank you for your thoughts. I certainly have learned a lot - although I had learned how to build full stack applications before I started working for him. Just to be clear - he's not my partner, he's my client. So I don't have any rights to the source code. Also, we're building a custom software solution for a business and not a Saas product.
- 9y ago

meric 9y ago

The OP's comments are dead on this thread. If you want to interact with the OP, turn on showdead on your profile.

throwaway23094 9y ago
Thanks for the comment. I suppose that is because I'm posting from a throwaway account.
livingparadox 9y ago
The entire account is marked dead. I had to "vouch" for the submission to get this thread to show in the first place. I'm not sure why they were hellbanned as this is the only submission and its very much a valid "Ask HN post".

philbo 9y ago

Invariably for questions like this, I think the answer is that you need to go out and see what else is available. Get your resumé up to date, send it to organisations that interest you, attend interviews. Just going through that process should help you understand where you want/need to be. When you get offers for alternative positions and have met the teams that you could be working with, then you'll know whether you should stay or leave.

DrNuke 9y ago

Until you get paid, all is good. As soon as reality (no customers) bites into your employer and he starts acting the colors of a failed business, politely jump ship and goodbye.

gargravarr 9y ago

If you're working with tech you like and you're earning a comfortable wage, I would say to carry on as long as you like, especially with an unstressed working environment. The trouble, and you seem to be very aware of it, is that everything could change at the drop of a hat - if the deal finally falls through or the costs spiral out of control, you could wind up in a nightmare. Keep options open. If you're working with good tech (which from the sounds of the software you're writing, you are), then the skills are transferrable and you ought to be able to move to a new job with little warning. As for the resume, it's great to see a respectable length of time at the same firm (because it shows dedication), and whether or not the project ever came to fruition is irrelevant to a new employer - that's on the people (person) above you. You're the person building it, you know the code and the tech, you're the one who makes things work. That's what to emphasise in your job search. I can totally understand your desire to remain in a non-stressed work environment, but it would be worth worrying just a little about your future and keeping a close eye on the market. Always keep something available. As much as you may feel loyalty to your current boss, you have to be responsible for your own career and personal state, and if (or when) everything comes crashing down, you can tell him you appreciated the opportunity he gave you, but you must look out for yourself. Don't let him drag you down with him; if his business decisions turn out to be wrong, it's his responsibility, not yours. At the same time, you can try to have a serious conversation about his approach. Lay out your concerns that you, as the author of this project, are not going to see your efforts bear fruit if the customer bails or he drastically underprices it; it begs the question, if he's priced it so low, what source of income is he using to pay you? Personal funds? Those will run out eventually. Tell him that if his business is to have hope of turning a profit, he needs to charge realistic amounts, especially if the customer can be pursuaded to pay more. After all, some businesses (particularly in the financial sector) will stick to a 'get what you pay for' mindset, and will not be convinced to buy a cheap system no matter how fancy the features are, because they will see it as low quality or unsupportable (the latter is a good possibility when they realise what they actually do need). In short, try to get your boss to see sense, but carry on as long as you're comfortable, and be ready to change jobs if the wheels start coming off.

dtnewman 9y ago

If you are worried about the possibility of losing your job and having to do without a salary, then you should start looking now. But from the way you asked your question, it seems like you are aware of this possibility and you are more worried about how this will affect your long-term career. My 2 cents is that in future interviews, it's very unlikely anyone will ask or care about the success of the project. They care about your technical skills and it sounds like this job is good from that aspect. You should be able to spin this in a positive light.

amorphid 9y ago

>> Is it terrible for my resume to work for years on a project that never sees the light of day? As a former recruiter turned engineer, I can say that you shouldn't worry too much about it. If there were a surplus of great engineers fighting for table scraps, I might offer different advice. You may find it mildly harder to break into gigs that want more experience working on a fast paced agile team, but the reality is that you'll always have a mildly harder problem breaking into something that asks for experience you haven't been practicing recently. What I'd be more concerned about is working on tech that is too crusty. If you're programming in MUMPS, using flat files as a relational database, and hosting everything on Windows 3.0 being emulated on OS/2, you may wish to revisit your tech stack. If you can't throw any not-stale tech into the keyword soup on your resume, it'll look like you haven't been motivated enough to keep your skills sharp. Disregard this advice if you have plenty of people trying to recruit you and/or you know people who'd hire you if they could.

hkarthik 9y ago

As an eng manager in SF, I'll form the dissenting opinion here. Get out now. Products need to ship and go somewhere. You only now what works in terms of your tech stack by dealing with the fires of actual production traffic. Lots of teams end up focusing on the wrong thing and building a product no one uses. It's totally okay for this to go on for a year. Going on for two years is a huge red flag and it might make you unemployable at a company that has a real product. Get out as soon as possible.

tedmiston 9y ago
Eh. Plenty of product is private. I worked for a few years on tech inside a military research lab where neither the product nor code will ever be seen by the greater public, but that doesn't change the learning that took place. It's not a concern to me or anyone familiar with an industry like that.

JSeymourATL 9y ago

> the work is techincally interesting and low pressure. What are you learning? What are the big problems in your field? How is this role stretching you professionally? Relative to career suicide vs vitality-- one should be continually adding and building skills that will be in demand. Richard Hamming offers briliant food for thought on your career > https://www.youtube.com/watch?v=a1zDuOPkMSw https://www.youtube.com/watch?v=a1zDuOPkMSw