Ask HN: Build my own startup or continue the high paying job? | Hacker News Reader

Ask HN: Build my own startup or continue the high paying job?

Like many in tech, I have had a successful career in a short period of time. Within 8 years my salary has grown 8x, I am often one of the highest paid people in most gatherings/social circles and having seen what not having any money looks like, it's a scary prospect to let go of a hard-earned high paying and stable job.

I also do not have anything to complain about my job, my manager or my company. I have had a lot of support from everyone at work which has helped me grow as fast as I did.

But the idea of jumping into the start up world, and building something of my own has been consuming me lately. I googled in search for online wisdom and looked at a few articles for guidance but didn't find many of them useful. Given this community is filled with entrepreneurs and others who have gone through the same dilemma at some point in life, I pose the question to you. What should I do? How should I decide which path to take?

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Build your project on the side and until it has enough revenue for you to live from; don't quit your day job. Startup life is overly romanticized. Dip your toes in by working your day job 40 hours and an extra 20 hours for your side hustle. Do this for a few months, and if you think you can keep the schedule up without a salary and it's worth it to feed your dream then hop in and good luck!

I did a similar transition. I started doing projects on the side, many of which never worked out. Finally when I got something that got traction I left my job. Your first idea could be the one but most likely it is not. Experimenting first while on the job will reduce your risk considerably.

This can be difficult depending on the company. Mine has every dev sign a non-compete that boils down to "If you write any code that competes with us is any way, we own it".

They used to let us file requests to confirm whether or not it does compete. They stopped answering and now just say "use your best judgement", which is a nice way of saying "We'll sue you if we need to".

Unless you are competing directly with the company, or doing anything that they are actively working on, any such non-competes, or 'we own your rights to whatever' will not hold in a court of law.

Better to hire a lawyer to verify that while in the well-paid job rather than later when the employer comes after the startup.

does this apply to Washington as well? I've wanted to get my friend who's been working at Amazon for years to do some game jammin' with me sometime, but he says company policy is that HR needs to sign off on literally any code he writes outside of work

While this is probably true, I work for a rather large cloud computing and online retail company who do everything. You can't name a field they aren't in.

High-powered engineers often assume that building a startup's technology is the same as building a startup. In this world, product/market fit is the ONLY thing that matters. A bad, but functional implementation of a great idea is 100x better than a great implementation of a bad idea.

Build an MVP that can acquire actual paying customers, and the growth rate/ROI will end up making the decision for you.

So much this. Most about building a tech startup isn't about engineering at all: https://news.ycombinator.com/item?id=3134322

If you still depend on a job for paying the bills (which means that you don't currently have access to lots of capital), then selling your product BEFORE you have built it is the only option I would personally consider going forward. And if those prospects are just entries on a waiting list. Our product was proven in a cheap 250€ ad test and requested by agencies before we all quit our jobs.

Missing product market fit is the top 1,2 and 3 reason for failing to build a startup.

This. I am in this exact position right now. Love my job and my team and am in a very high paid position, but am trying to grow something on the side.

I am beginning to see some real traction with https://www.budgetsheet.net and it's currently at ~$500-800/mo, but I can see a clear future where I will likely have to make a choice to leave my day job before it is making anywhere near my FT salary. It's a bit difficult to know where the line is.

I'm in such a similar position! Contemplating exhausting the existing profits and/or adding some of my own funds to ramp up marketing for growth (also so I can concentrate on the tech side which I'm good at, and where there is still great market opportunity from unsupported platforms)

In other words, parent is asking you(OP) to validate.

If you have a problem which is itching you to solve by building something, Then it's probably the best way to get started without quitting your day job. If others are willing to pay for your solution for solving their problem, Then you might have a startup idea(which actually can work out).

P.S. In case you want to take a look at some problems which needs solution (or) to check if there are others who want your problem to be solved then I run a platform for that - https://needgap.com.

"building something of my own has been consuming me lately."

How bad is it consuming you lately ? Do you think about this every day ? Do you feel like if you don't do something about this, you would be very unhappy say 5 years from now ?

Let me be brutally honest hoping it helps. Most people think about doing this own thing since it is a "nice idea". But the execution part is where a lot of us fail.

So the question is: what are you willing to give up today to start something of your own ? Are you willing to give up the salary cushion you have ? Are you willing to grind day in day out for 5/7/10 years ?

Let's say you do your own thing today and 5 years from now, you decide that it is not for you and you want to go back to a job. Would you regret your decision in hindsight ? Would you hate yourself for losing all that cash you could have made in 5 more years from your current job ?

For me, the answer is No, not at all. I did not fail so you can call it survivorship bias but 7 years ago, I quit my very high paying consulting job to do my own thing. I was able to make it work but even if I had failed, I would have 0 regrets. I cannot die knowing that I never tried my own thing. Can you ?

You gave me something to think about codegeek. Haven't looked at it from this lens yet. Thank you.

Not a problem. Doing your own thing is one of the best decisions you can make for yourself but you cannot have it both ways. If you are worried about Opportunity Cost, you would never truly be free in actually doing it.

For me, doing my own thing is my way of life. I cannot accept anything else. Of course, I hope I get rich doing it as well but even if it keeps me afloat, I would be ok with it.

You don't do your own thing because you want to get rich. You get rich because you did your own thing. 2 different things. The focus should be "I really really wanna do my own thing and willing to accept whatever risks it brings". Good luck to you.

As per the intro on your user info page, how do you prefer one get in touch with you to have a chat? Curious about what your business does and how you got started

I second that. You regret the things you DON'T do more than the things you do. In 10-20 years' time you might get bitter wondering what could have been, and seeing another company succeed with "your idea".

It also sounds like you can afford to make this bet. You are young, good savings, tech skills, and I'm assuming "asset light" life (no family or lots of bills weighing you down). If the startup fails you can get back to corporate life after a few years, which startup life experience under the belt.

Another answer said that you should love the market you're in. I agree. You'll live and breathe this market for 7-10 years, so you better love it.

That being said, most startups fail. You have to be fine with the fact that you might lose your savings and those years of your life. And if it does, fine, it's an investment that didn't pan out.

What I did when we made the jump (8 years ago) was set aside a pile of money and a 1-year window to see if the company floated. If the time or money ended before we saw paying customers and some small traction, we'd stop. It all worked out fine but we were very lucky.

I went through this, so I am answering from experience. It was over 15 years ago though, so take it with a grain of salt.

First of all, how much do you love money and the luxuries it affords? I went from a well paid engineer spending freely on whatever I wanted straight back to living with my parents and eating my mom's cooking. I had savings but did not touch them - they were for emergencies, especially medical ones: I had no insurance. Took me 3 years to go back to making some money, and 5 to be comparable to the original level.

Secondly, how are the people around you? I was lucky to be partially understood and not discouraged by my parents and girlfriend and accepted by my friends. Without that I would’ve quit pretty fast.

Third, do you have an actual idea for a product? You need to be in love with that idea, not with the idea of being an entrepreneur.

Finally, how much do you love sales? You’ll get nowhere without them.

Now, if you answered yes to all above, don’t convince me. Go ahead and convince a cofounder. Work together in your spare time (plus a vacation or sabbatical) a few months and build a proof of concept. Then convince an investor for some seed money for a first hire.

Then and only then you can decide to go ahead and build your own startup…

Remember: you can get anything you want in life. But everything has a price. The trick is to really understand that price. The question is: Are you really ready to pay the price?

If you are living in the Bay Area, do not quit your job unless you have enough money to keep your own lifestyle in perpetuity.

I have so many friends that have regretted going into startups because they have missed out on literally millions.

If you don’t have a house right now, do not go into a startup because the ones in big companies will earn more money than you and you will effectively take a break in making money for years.

Of course you might work at the next Uber, but chances are 10 to 1 that you will instead work at the next Juicero. The 5 years you dedicate to that job will see no money but the stock market will rise and you won’t see any of that so your peers will get richer and richer.

So if you have a house and enough money to keep your lifestyle no matter what, then sure. Go for it. If you don’t, then wait until you have enough. Or if you don’t care about money and are okay with things like housing being completely out of reach then that’s okay too.

Not having money would also probably consume you.

If you have to ask some strangers on HN what to do with your life, you’re almost guaranteed to not be ready.

You’re going to have basic questions about setting up your business, insurance, contracts, payroll and HR, vendors, before you even get to your business idea.

If you don’t have that all sorted out, you’re not even in the right place yet. You’ve got some homework to do before you even take any sort of dive.

Maybe you’ve started a business before and don’t need to hear this, but from what I can tell, you haven’t and startups are not typical small businesses.

If you don’t know how to run a simple small business before attempting to run a startup, you’re going to have a bad time.

Also, I don’t know who is going to take you seriously in fundraising.

I've received lots of similar gatekeeping advice: "If you haven't done ____ you're not ready for ____."

Very happy I didn't listen to any of it.

Yeah, and my point is that he shouldn’t be listening to people on HN.

The guy is either going to do it or not, and when he looks back, he’s not going to say, “Wow, I’m so glad bugblaster1337 told me to reach for the stars.”

everyone saying to build on the side probably hasn't built or shipped anything on the side. building on the side: - hard to think deeply or carve out deep work for side project when work + life keeps interrupting - hard to make progress if project is ambitious given time constraints - enthusiasm can fade due to interruptions

if you have a very high conviction and high savings, the best would be to jump into it. the thing with leaving your job is you can always find another one

+1. I think people romanticize shipping on the side, and for many people that's the only option because they can't afford to quit their job and have no income.

For someone with a high paying job where you can save up money, reduce your expenses, and then quit your job and dive in 100% while knowing your costs are covered for X amount of time, that's a huge advantage to starting a company. You should definitely consider this path if you can.

Strong agree. Building on the side seems like a smart, low-risk move, and you could try it to see if it works for you.

But it's easy to fail to maintain enthusiasm/momentum when working on the side, simply because you don't have the time/brainspace to devote to it. Experimenting with/failing at a side-project won't prove that trying to start a full-time project/startup isn't for you.

I made this jump in 2019. To some of the points made here:

1. You need to understand why you want to do a startup. "Building something of my own...": why do you want to do that? Why is that important to you?

2. Find a problem (market) you love, not a solution (product). You will be working on that problem for the next 10 years.

3. Talk to startup founders who have failed. There is a lot of celebrated romanticism of successful founders. 90%+ of startups fail though. Those failed folks are pretty smart and capable, but it's an uphill battle. If you've typically succeeded at tasks you set out at, startupland can be a big ego hit.

4. Is there a hybrid approach? One failed startup founder I know decided to work at Amazon after and try to grow a division there. He was successful in that. He took it from <$10MM to >$100MM as a GM. Zero to one is hard.

5. There's a lot of unglamourous stuff. e.g., all things legal and finance. If/when you hire people, you need to also focus on management and growing your folks.

I actually disagree with most of the advice here counseling you not to quit.

It sounds like you would be able to find a similar job with similar income if you quit, tried to start your own project, failed, and re-entered the work force.

If you are at a life stage where the opportunity cost of trying to start a company for a year is approximately one year of salary, then I would try it.

Unless you have dependents/need a steady income, then it is probably too risk-averse not to try collecting new experiences.

A strong suggestion: I would find a cofounder or someone else to work with before quitting or trying a startup on your own.

Basically: if you are secure in a high income bracket, you might want to optimize more for exposure to positive, exciting opportunities, rather than play super-conservatively in a way that minimizes variance, may or may not maximize expected value, but certainly eliminates exciting upside.

> I also do not have anything to complain about my job, my manager or my company

This is gold, Even as someone who is very risk-seeking I'm not sure I would want to give this up, until I was truly ready to break out on my own, fully independent, AND have a war chest to play around with startups. However, you might have a different risk tolerance and appetite as me, or, maybe there's nothing to complain about and that's why it's boring. With that in mind:

> Within 8 years my salary has grown 8x

If you're in tech and have had that trajectory, why not pay someone to work on your startup?

Have you read about other famous startup founders that left high-paying jobs? Examples:

- Jeff Bezos quits prestigious job at David Shaw hedge fund to start Amazon

- Jensen Huang at age 30 quits his director job at LSI Logic to start NVIDIA

- Eric Yuan quits his VP of Engineering job at Cisco to start Zoom

Is your conviction for "building something of my own" as compelling as theirs? Is your software idea so motivational that you're also willing to work 90-hour weeks including weekends every week to help get the business going?

At the risk of an HN forum like this doing armchair psychology on your level of commitment... the following quote from your other reply is a red flag: "My biggest dilemma is financial outcomes. With my job, I have a guaranteed path for good financial outcomes..."

For many successful founders, their biggest dilemma was not starting the business to build their idea instead of worrying about a comfortable salaried job paying better in the future. In other words, a startup founder is a little it irrational in choosing to build a startup because statistically, the expected financial outcome is likely failure and bankruptcy. The irrational startup founder doesn't care because must build his software idea to see if it works.

Always remember survivor bias. For every Jeff Bezos there are untold masses of people who quit their high paying job and ended up in financial ruin, but you are never going to see those people on the cover of Forbes.

Also consider how much financial cushion you have. Bezos had his parents invest something like a quarter million dollars to keep his business afloat in the early years. If you don't have that kind of safety net, your risk of financial ruin is much higher.

Just something to consider.

I would recommend you stay in the high paying job. Being a big tech employee is worlds apart from running your own company. And it seems like it is a strength of yours to work in that environment. Running a startup for you is like starting at zero again. Not a lot of people can do it successfully and it takes times. You have to have a strong passion to start a company and I just don't see it if you have to ask.

What does your savings situation look like? If your income went to $0, how long could you comfortably continue living without withdrawing from tax-advantaged retirement accounts or otherwise drawing down on your savings more than you’d like? Don’t assume you’ll cut expenses or be frugal to extend your runway. Use your current spending to calculate this.

Second, do you have an actual startup idea to work on right away? Or do you simply want to do anything that comes to mind? In my experience, it’s much easier to get started and follow through when you’re targeting a specific, known goal. I’ve seen people jump into “doing a startup” without an actual goal in mind. They spend a lot of time spinning their wheels and pivoting over and over again. I’d suggest nailing down the business idea before you leap.

Third, consider finding business partners first. Solo entrepreneurship is extremely hard and can be very lonely. It’s much easier to work in pairs or a group of 3 founders.

My current savings give me a runway of about 2 years with the current lifestyle, if my income went to zero tomorrow. I have been saving for this for the last year or so and would have a runway for 4 years if I continue my job for another year.

I do, I have been validating my idea and have enough to put a pitch deck together. I get commits from the first 3 potential customers as well, to create a strong case for the business.

Yes, I have some potential partners.

My biggest dilemma is financial outcomes. With my job, I have a guaranteed path for good financial outcomes (a million in savings or more, conservatively speaking) if I stick it out for another 5-8 years. But is giving this up a good path? I could make a lot more or nothing at all.

If financial outcomes are your biggest dilemma, you gave yourself the answer.

Let me tell you from someone who's in the twilight between "I should go back to a job" and "I can see how this project is going to increase my lifetime earnings compared to a conservative job": It's not cool. I was in a lesser earnings situation than you, still 3-4X what I make now building a venture.

It's a mental marathon and you need to operate and execute despite that. If money is your single biggest motivator/ driver (nothing wrong with that, it's preeeetty high up for me), the ride will be quite rough I think.

Thinking you or I will be the exception to this rule is rather delusional. The best thing I would suggest is to try and leverage your skillset by getting into a team early when others already have de-risked the idea a bit. Requires quite good networking, though, of course.

Your cost of living sounds kind of high if you only have a 2 year runway on your current high salary. If you reduce it a bit, it wouldn't be hard to have a savings rate of at least 50%. You could read the "Early Retirement Extreme" book or check out mrmoneymustache.com blog posts sometime.

If I were you, I'd do the following: live frugally and continue your career until you reach a point where you can safely and comfortably retire. Look into FIRE (financial independence, retire early) communities and resources for more info. Once you reach that point, do whatever you want because the money no longer matters. Especially if you are okay with your current job, I personally wouldn't throw such a great position away just to gamble on a personal business. If it's really consuming you that much, just do it on the side. If you can't keep up your current job and get your business started in your free time, I personally don't think you'll have what it takes to power through the business anyway.

If you want a "safer" financial outcome, quitting your job and starting your own thing is NOT the answer.

If you can do your product without raising money by actually making sales (bootstrapping) and making a profit every month, then this is more "safer" than raising money as you will lose control over your financial outcome. The successful ones (there are not a lot) get a lot of press but there are a lot more failures with raising money and then figuring out profit

Build an open source toy project from start to finish in your spare time and beg people to use it. You will scratch your itch

> building something of my own

What prevents you from doing this right now? At nights and/or on weekends, building your own thing(s)? IP assignment agreement? Lack of time or energy?

My suggestion would be to start now. Start programming things. Most of the Y-Combinator advice seems to be to let the project dictate making a startup as opposed to starting a startup because you want to start a startup.

Also, keeping in mind your IP assignment agreements at work, go to your accountant and open up an S-corp or LLC. If you are very ambitious and want to get angel funding etc., start a Delaware corporation - there is plenty of advice here how to do so. I myself have an S-corp in my state, because I am not working on anything at the moment that I foresee eventually trying to raise venture capital for.

Again, keeping your IP assignments in mind - why not launch while still working? Work your day job during the day and do the side gig at night.

I would recommend doing your best to try and figure out a way to not leave your job completely, yet still give yourself the time you need to build something without completely relying on doing it on the side. Can you cut your time back to 4 days a week, and work on your start up on the 5th day? Can you take a sabbatical for a month or two so that you can dive deep on building something without having to completely leave your job?

I would assume that if you're that successful that your company would be willing to give you some flexibility as opposed to you just outright leaving, and that you have the financial means to do so. Rather than having this be an all or nothing thing, figure out a way to leverage some flexibility to build while maintaining some connection to your current job/position/company.

Why should you be the one building it? Why not take a chunk of the 8x salary, find a person to execute first year or so of the idea? Once it's direction is clear, you can jump full time to it. I understand the other person might not be passionate but atleast he will be your employee.

That's actually a great suggestion

A better question is who depends upon you? Are you single? Married with children? It isn't just you when this discussion comes up. If you drop your job to pursue a pegasus, are you the only one without health insurance, dental etc??? Do it on the side if you do it all. I've been broke all my life and while I wouldn't have pursued the two most logical paths to better money because I believed they would not have made me a better person, I cannot advocate for someone giving up the means that comes with a successful career. I think you should keep your job, bank as much money as possible and scratch your itch in your off hours and on weekends. Just my half penny. HTH

Build it on the side (if your employment contract allows for it, by not claiming all IP you build belongs to your employer).

It'll be slower, it'll take you nights and weekends, but in my book that beats the desperate hustle for cash you have when you've got 0 revenue.

By building it as a side project you can pull the trigger once you get some traction.

As a tech person, you probably hadn't had much experience with marketing, sales, business development, company paperwork/taxes .. all important stuff that will sink your startup if not done well. If you're doing this on the side, you've more time to learn the chops in those areas.

Grass is always greener on the other side, don't let that blind you to the grind.

Since you are debating whether to let go 100% of your salary for your startup, you can also think about how much % you are willing to invest in your startup for getting outside help (yes, even for coding). This route is often completely ignored by founders but if you get freelancers/contractors from the right geography, you might end up speeding up your project more than if you spent 100% time on it.

Many new founders don't think of this route because they usually have a individual contributor role in their full-time job and don't appreciate the productivity scalability in managing others.

If you think you have an idea worth pursuing, work on it on the side while keeping your "day job". If it takes off, quit your job once you can replace your income with the side work. Also, as a warning - double check your intellectual property agreement with your employer. Some employers will draft them so as to read that ANY idea you come up with (either related to their business or not, just because you work for them) is automagically THEIR intellectual property. Needless to say, this not a good position for your new brilliant start-up to be in.

You should absolutely do it. Chances are the startup won't be successful, but it's a life experience you won't regret having.

Start building something on the side, and make sure you have enough savings to maintain your life without getting paid for a while. Once you have some traction, you should be able to raise money and hopefully pay yourself a reasonable salary.

If you do fail, you shouldn't have any problems getting re-hired. Sounds like you've been successful in your career so far, and the skills you learn as a founder will only make you more valuable.

If you've been working at the same company for a while, ask your HR department if they have a policy around a leave of absence or a sabbatical! You can take a few months off to build a prototype of your idea, test it out with some users, and then decide whether to return to your day job or continue with your startup idea full time.

This will be much less risky than quitting your high-paying job and going all-in on a startup idea. Many startups fail for a variety of reasons, besides just poor execution.

Whatever you plan to do, make sure you have a backup plan.

Yes, this. Though I am not sure if I would start at HR or with your manager/director because of the risk of telegraphing an intention you do not yet have, leaving the company behind.

If you have a very good relationship with your manager/director, I think I would start there, something along the lines of "I've got this germ of an idea, and it won't leave me alone. It's in a completely different area, and I've got such a strong urge to explore it... ...but I like this place so much, I don't want to just walk away."

Leave it open like that, see what they say. They might offer the sabbatical idea themselves.

Alternatively, if your co's HR policies are available for all to peruse, check for the aforementioned policy.

Another alternative, based on experiences friends and colleagues of mine have had....

If the owner or GM or insertHeadHonchoTitle here is very entrepreneurial, spend evenings and weekends working on a business plan or 7-10 slide pitch deck, then, when it is ready to go, let them know you are heading out on your own.

I know a few people who did this and, instead of being thanked for their service were offered their first angel investment. Their boss, Terry Matthews, knew he had good people and knew he could make more by funding them than either keeping or just letting them walk away.

Good luck!

I recently left my job so I could contract to pay the rent and work on my own ideas.

I've had a number of connections who have done this and of course there are more famous cases like Basecamp.

There's not as much risk and there's no fear about IP. You also don't need to do all the extracurricular worrying about employer product, org direction and dealing with on call.

The hardest part I anticipate is just getting depressed from not being able to make progress fast enough. That or not having enough human/coworker interaction, which is a big deal for me.

I think the drive to do something like this will not be with you forever. Once you are in your thirties you will probably want to prioritize your (potential) family life and will not have time or inclination or freedom to pour yourself into a start-up. So if you have no current commitments/responsibilities outside work, and there's a good job market for your skills to fall back on later, I suppose it's now or never. Even if it fails I'm sure you'd learn a lot.

Been there and back. Quit a high-paying but crappy job together with my cofounder to do our own thing. In hindsight we were so naive and unprepared. After 8 months I was lucky to find a part-time staff-aug contract, so I'm doing that now while continuing on one of the products that got some traction. This was even with plenty of money still in the bank, as I felt we weren't really going anywhere at that point... Some thoughts:

- A high paying job with good environment which you don't dislike is very, very valuable. Lots of folks will say you can get another job again if needed, but you're starting from scratch again in terms of clout, and it's hard to judge company culture from interviews so you might get a worse environment

- The opportunity cost is very real, both in terms of what you’re leaving on the table and what the profitability bar of your business will be. It would’ve been easier if my full-time job only paid $50k.

- If you wanna take a shot at it, REALLY commit to it instead of half-assing it. That way when it's all said and done you can sleep well knowing you gave it a good run. (That said, still advise trying to find product-market fit and figuring out the X's and O's part of running a business while you're still employed)

- What course and decision is best for you will be VERY personal. This is one of my biggest takeaways from my time. It’s as much a journey of figuring out your limitations and yourself as a person as it is about the business side and product.

- My "it" moment was when I got a pang of extreme jealousy when a friend told me he got a first major customer for his side product.

- IMO next to having a partner and child, creating and running your own business is one of the most special life experiences you can have. It’s what I think about most of the time when I’m not working, and getting new customers / validation feels so much better than anything I can experience at work. I also truly enjoy the creative side of it, where the world's your oyster and you’re free to do literally anything you can fathom to grow the business.

- Know what your end goal is. Personally I’d enjoy the day-to-day of running a lifestyle business I could live off of because I’ve gotten to the point where I’m ambivalent about regular software dev work. But that’s just me.

Thank you, granshaw. Yours inputs have made things a little more clear for me.

Really glad to hear it, and best of luck :)

Everything had tradeoffs. Don’t think of this as a binary “work vs startup” decision. Instead, take some time to think about what tradeoffs you’d be making in other areas of your life. For example, 0 income could affect your decision on how often to eat out, going solo means taking on all support issues which can affect your social life. No one can answer this question for you, but the collective wisdom here can help you ask yourself the right questions.

> Within 8 years my salary has grown 8x, I am often one of the highest paid people in most gatherings/social circles and having seen what not having any money looks like, it's a scary prospect to let go of a hard-earned high paying and stable job.

> I also do not have anything to complain about my job, my manager or my company. I have had a lot of support from everyone at work which has helped me grow as fast as I did.

Why would you ever leave?

Keep the job until you’ll no longer be asking this question.

Keep your job, hire freelancers to build the MVP, reduce your working hours once you confirmed the market fit with a few customers, switch to consultancy or part-time job when your startup makes enough money to pay your bills for at least 6 months in a row, quit your job when your startup makes enough money to make you happy but you feel it needs to grow faster than before.

> How should I decide which path to take?

I've been in exactly this place (big salary in big tech, started my own company). I find that these types of decisions are complex, I don't think I could capture everything in a comment, but I''d be happy to throw 30 mins on my calendar for a Zoom (9-5). Shoot me a DM on Twitter (@MattLovesMath) or LinkedIn if you'd like to.

Thank you, MattyMc, appreciate your offer. I will take you up on it soon. :)

Both.

Build it on the side: evenings and weekends on your own equipment NOT at the employer.

Get undeniable traction (preferably sales and investment) before working-out a resignation and continuity plan with your employer.

Good employers (managers with rational egos and empathy) should want you back if it doesn't work out because you're a known quantity.

Do NOT burn your ships (or bridges) behind you like Cortés.

Your fifth startup will be successful. First four will not. So, save money on first four startups for the fifth one, e.g. commit 10k for a first startup and try to make it profitable first (you will fail with probability of 99.9%), then commit 20k for a second one, and so on. Don't leave your job until a fourth startup at least.

Entrepreneurship is a... special kind of mindset. You have to basically trick yourself into believing that you unconditionally love a project that will hurt like nothing else ever has. Most people don't come out the other side the same, so you should be wary of throwing away a comfortable position.

> Most people don't come out the other side the same

This!!

My greatest fear was that once I tried it I'd like the founder/owner lifestyle and mindset so much that I'd not be able to mentally go back to the corporate world, and that has unfortunately somewhat come to pass. Right now in an in-between situation trying to figure out my next move.

Stay in the high paying job, save, retire, do hobbies.

Alternative: Work really hard for almost no money. If it goes well, you can make close to your engineering salary again as a founder. If you "win the lottery" you get an exit and get to retire and do hobbies.

I assume you work 5 days a week? Can you not go to 4 days a week and spend 1 day working on your side project full time until it has enough merit? If you do, make your day a Wednesday, not a Friday, otherwise it just becomes part of the weekend.

Thank you everyone for your comments. These have been very very helpful and I think I have a better idea of what I should do. Appreciate you taking the time and helping me out!

Do you have the option to go on a leave of absence? I have friends who have done this to work on their own ideas or go traveling for an undetermined amount of time.

What is your startup?

What appeals to you about a startup?

It's a couple: 1. So many real needs that people have that are unmet. Anyone who has a potential solution should try, if they can afford to of course. 2. Having as much control over my life's outcome as possible. It's never a 100%, may not more than 50% even, but I don't feel like I want to wait for someone else to dictate the terms of my success anymore. Don't know if it's just a millennial thing or there is merit to this feeling.

How much are you paid?

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