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Quitting job to focus full time on your hustle, what did/does it take for you?
39 points by ayushjangra on Aug 1, 2022 | hide | past | favorite | 36 comments
Hey, hustlers!

I thought that all it would take was some determination, some hustle, and a few sacrifices, and then boom—I'd be free.

But as I've learned over the years doing this stuff full time, it's not that simple. There are so many factors that come into play when deciding whether or not to quit your job and focus on your hustle full-time.

If you're in the SaaS world, it can be easy to get comfortable with your existing work/life balance.

But at what point do you start to wonder: "is this really where I want to be?"




> "I'd be free"

Free from what?

I'm 4 years into being "free" from a corporate job but this was just a trade off. Here are the tradeoffs from going corporate to solo:

1) Instead of everyone telling me exactly what they want from me; no-one can tell me what they need.

2) I have no deadlines. Anything and everything can drag on for as long as I fuck around with no end in sight, or have to step up and deliver.

3) I have no co-workers to talk to during the work day, or to ask for help from.

4) I have no office away from home, unless I go sign a contract and pay for it.

5) There are no guaranteed paychecks, ever. The sky is the limit with how much I can earn, but the bigger the paycheck usually means the longer the wait until the next one.

6) There is no guarantee of success. And even if there are snapshots of success; I can guarantee it wont stay that way forever.

So going back to your tell... Be careful what you wish for, and be very clear on what you are trying to free yourself from. Maybe look at it as what you are getting yourself into instead of what you are running from.

From the hustle scene: success can only be built on top of a mountain of failures. If you feel uncomfortable at your job then it's normal to think the grass is greener elsewhere. Maybe your job sucks and you do need to change it up, but unless you're a masochist stay away from going solo.


I've lived both lives.

Unless one is financially independent due to inheritance or having made out well with company stock, we are all running from the bear. The bear being healthcare bills, housing and living costs. If you run your own company, as in have for years, you are running from the bear yourself. If you have employees your also responsible to pick them up and make sure they don't get eaten.

In a company where you are not the owner, others help you in running from the bear, you're not alone.


7) You no longer have a corporate boss. You (hopefully) have many. Every new client is an additional boss instead.


Employee - Boss relationship is VERY different dynamic from Provider - Client relationship.

Realized this once I became a contractor. I no longer have a "boss". I have "customers".


I'm self-employed, and my boss is an ass...


> Free from what?

from my understanding (and my own personal desires), the idea of becoming free is the idea of FIRE - financially free (not necessarily retire, but retire from having to produce money to live off).

I think it's part of one's journey to climb the maslow pyramid. The exact nature of the work being desired after becoming "free" is not the same for everyone, but it's a higher form of desire than to produce value economically.


Hustle culture is perpetrated by people who have something to sell you. They pretend to be successful until they are; their product is themselves, and there isn't much room in that space. The truth is that it's quite hard to make a passive income equivalent to what you earn from a day job, and it takes time to build. You tend to have to be willing to experiment. Most experiments (like, 95 percent) will lose momentum by a couple percent per week unless you're putting a full-out effort into them. Terminate those, even if they were the ones you hoped would succeed. Others will grow by a couple percent per week. Double down on those, even if they're not the ones you were passionate about; those are the sacrifices you have to make if you want to make the same kind of money.

The truth is: this process can take years and nothing is guaranteed. Plus, your app that makes $30,000 per month might crater due to regulatory changes, competitors, et cetera. Most of the self-styled passive income gurus were independently wealthy already, or at least had the connections necessary to get back into respectable work if nothing panned out (which makes a huge difference). If you're working a regular prole job--even a programmer prole job, which is physically undemanding but humiliating (daily scrum)--you're probably going to be too exhausted to put all that much into a side effort; that doesn't mean you're weak or lazy, but that you're human.

I don't think you should quit your job and focus on your hustle until you're 99.5 percent sure that it can fail (or that you'll start to hate it once it becomes your primary source of income, and burn out) and you'll be alright. This means you need to build the skills, savings, and connections necessary to be safe if you need to run back to your old career.

Life circumstances can also push you in funny directions. I'm (mildly) disabled and (unrelated) almost died in 2019, and the reflections on my own mortality brought me to take time off to finish a novel (out in '23) and go back to graduate school and try for a legit research job... although it'll be several years (if ever, adjusted for inflation) before I'm back at my old TC level, because research pays 50 cents on the dollar compared to corporate garbage (a pay cut that's worth it, IMO) and no one can predict book sales (even the so-called marketing experts in publishing houses get it wrong half the time).

Good luck. It's hard, and the odds of each attempt are low, so you'll probably have to make a number of attempts. Don't trust anyone who makes it sound easy.


Great points!

Now, I don't think that a hustle must necessarily equal "passive income." It can be a freelancing hustle, or a product hustle, or a SaaS hustle, but there's nothing passive about them.

It takes time to come up with an infoproduct, for example, and you've got to promote it, build your circle of followers, etc. And even if you do everything right, there's a huge amount of chance/luck. Your product might take off, or it might crater (or anywhere in between). Either way it's a lot of work.

Anyways, just my 2c, and good luck with your book!


The big thing I have learned with all of this, a fully fledged product often takes much longer, like six months or a year longer, to get to a good state than you would estimate. The pressure of no income while working on your idea is not too bad, until you go 6-9 months with nothing released. This is a huge factor in people failing. You need comfort to build something good without fretting about money/time. Cutting corners to get it out the door doesnt always work. I think the idea of the "lean" MVP is overplayed, some businesses take alot of time and software development to get right


It’s certainly true that you should launch something as soon as is reasonably possible. This is so you can get into a customer feedback loop and start iterating on the product to improve it and build a better product with actionable information. However, how long it takes to build a reasonable MVP depends on a whole lot of factors, like existing competitors, target audience, scope of product, industry, etc etc. some simple saas products can take only a few weeks to build, but if you’re in the aerospace industry a prototype will take years if not more.


Yes, the actual product development takes a long time. But you're not even close to done when you have an actual product. Now you need to market/sell it (which hopefully you started doing while you were building it). And even when you have customers initially, it usually takes 2-4 years for you to build momentum, build trust, build a brand, such that the revenue becomes meaningful. It's almost impossible to go from $0 to 6 figures in revenue in a span of a year.


Hustlers I've met were homeless at one point, didn't have family support, worked 2 to 3 jobs, and got out of homelessness and successful now. None of them write blog posts or use social media.


They should, it'd help with their hustle.


If you don't give it a go you're always wonder "What if?".

But keep your day job for now.

I always recommend @DHH's startup school talk: https://www.youtube.com/watch?v=0CDXJ6bMkMY

You need to balance family, day job and your SaaS/Hustle then you won't have any regrets.

I would recommend keeping your day job as long as possible while still making progress on your SaaS/Hustle.

Having income should make building your SaaS/Hustle easier up till the point where it replaces your day job income.

SaaS/Hustles can be slow to grow revenue. https://businessofsoftware.org/talk/how-to-negotiate-the-lon...

It's hard balancing both but the nice thing is if you love your hustle it won't feel like work.

Checkout Microconf videos and StartupsForTheRestOfUs podcast.

Rob Walling has lots of advice on how to transition to full time on your side project this.

Oh, one more thing. If you want it to replace your day job, don't think of it as your hustle. Aim high. Don't think you're going to get funded but don't aim for $100k AAR think about how it could be $1M or $10M or even $100M AAR. It probably has a higher ceiling than you expect.

Good luck my friend. Follow your dreams (responsibly).


In my experience, aiming high doesn't matter. You either have a big market or not, and most people initially overestimate their market size.


This is true. I've seen a few small SaaS that should have dreamed bigger who had the idea first. I had a stripe dashboard before baremetrics but totally underestimated the size of the market. A friend had a tool like Buffer that was earlier and got some traction and had a small exit but he didn't dream what he had could scale like buffer did. Granted could have requires lots and lots of work. But neither of us considered being able to even try to get to that scale. So dream big or at least take a more serious look at what scale your 'hustle' could reach.


Some numbers for perspective: Baremetrics spent almost 8-10 years working on their product for a $4 million exit. They didn't raise a lot of VC capital, so their founder got a very good payday b/c he wasn't diluted that much.

Buffer still has not exit, to my knowledge and has had 2+ consecutive years of falling revenue. Their list of acquirers is getting shorter and shorter, and their founders have not cashed out yet(excluding the 1 who got ~$1 million or so after raising from VC - very distasteful IMO). Buffer and Moz are the 2 companies that are examples of companies that aimed too high, raised too much money, and made a success less likely for the founders.

So, sometimes aiming high isn't that good if it means raising capital, and where a few $million exit won't be a huge success since you're getting diluted.


>Some numbers for perspective: Baremetrics spent almost 8-10 years working on their product for a $4 million exit. They didn't raise a lot of VC capital, so their founder got a very good payday b/c he wasn't diluted that much.

His investors walked away from their $800k invested so that was helpful.

Even still, netting 3.7 million sounds great but it's somewhat misleading. For comparison, if you got a job today for 250k, got 5% raises, and invested all your money at 5% returns you'd end up with 3.5 million after 7 years.

That's kind of where I always end up w/ bootstrap SAAS ideas. My salary as a developer always sounds like a lot but it really sounds like a lot when you start talking about charging customers to match it. When you add in time value of money and risk the path to a successful bootstrap SAAS is a pretty narrow one.


1) A 250K job is not readily available for everyone, let alone 350K if you're taking into account annual raises for 7 years.

Sure, if you're fortunate/diligent enough, but not everyone can get into FAANG, or have what it takes to master those interview questions (or want to). I also believe the founder of Baremetrics did not have a developer background.

Even if you are able to make that much in your job, the math starts to change dramatically when you have a bootstrapped company, where you can pay yourself half your regular salary for years before you decide to sell the company.

2) Yes, investors walking away from 800K is a good valid point. If we want to talk about true bootstrapped successes, BuzzSumo and Backlinko are better examples.

But yes, the path to a successful bootstrapped SaaS is a narrow one - it's always been a narrow one. But even with a narrow path, it's still larger than the path to a successful funded SaaS. Both have low probabilities of success, but one is more of a moonshot than the other, IMO.


That's true, good points. Yeah, it's a nice balance finding the sweet spot. I did see the article about buffer's revenue peaking and has continued falling.


Fortune favors the brave, but I would say don't quit the day job. Try to 'borrow' 20% to work on your hustle as a hobby project - the company will almost surely get that time back in increased quality and productivity in your day job. I did that 25 years ago, then lucked out by making an initial bootstrap sale that got the ball rolling. My first effort ran for a dozen years, but since then I've been side hustling my side hustle. It's fun to follow your interests, but it's not a good way to have work/life balance.

So much of people's outcome is based on luck, which I got more than my share of. The best advice that I got, however (that you also have to be lucky to take), is to find like minded people and do something with a partner or group.


Day jobs take up so much of your time theres none left to focus on your projects. Especially if your job wears you out and by the time you get home the only thing you have energy to do is eat dinner and shower. I finally just quit my day job, i do have some income i get from a rental property i own so that allowed me a safety net. But for those without any safety net it’s difficult. Maybe if you live with parents and can just work a part time job somewhere then dedicate 30 hours a week to your projects.


Not at all. There are plenty that don't. There are plenty of companies that allow folks to work reduced schedules, take sabbatical etc. I've personally known dozens in this boat.


Yep, of course if you're not willing to downgrade from a FAANG job with free food, 300K+ in salary to a company that gives you more flexibility in time/remote work with less salary, then of course the conversation is over, before it has started.

But there are certainly companies out there where you can do your own gig for 30-40% of the time, let alone 20%, and still can get by.


I would say that if we feel some lack of passion in the regular job the it's already the time to start wondering: "is this really where I want to be?".

However, starting something of our own needs a very careful planning. It also debends on an individual's situation.

I wnt through that journey myself. I was loving my job, but then came a time when I felt that it reached that stage when many of two days were proving to be same. I was into IT, but had moved to the business side. Starting a tech venture just based on my skillsets was not possible. I decided to start something into IT recruitment. It was something completely new to me. A completely different path.

It was not really ethical to devote time in preparing myslelf for the new journey, when I was in aregular (and damn good) job. But then sometimes one needs to weigh - it's my tomorrow's survival and success or being a Godly monk - only 100% loyalty to the employers. Well, I decided that after close to a decade of giving my 120% or more to the company for 10 years, it would not be unethical if I give 75% for 6 months or so.

I am not ashamed to say that, that's what I did. 25% time for 6 months used in preparing and learning about my new hourney - and then I started my nown company 3 years back - and since then we only greww, with no looking back.


> It was not really ethical to devote time in preparing myslelf for the new journey, when I was in aregular (and damn good) job.

Nothing unethical in preparing a side hustle outside work hours.


Keep in mind that as unpleasant as corporate work can be, it still means reliability.

Sure, you can make more money and be happier freelancing. But if you want to start a family, there could be risks.

I don't aspire to be a family man, just a thought.

P.S. Unexpectedly, a list of monetizable hobbies: https://custom-writing.org/blog/affordable-hobbies-you-can-m...


I’ve run the numbers for myself. Every dollar of SaaS revenue is worth 2X that of a dayjob dollar.

I’m not saying SaaS money grows in some mysterious way, or that it’s easier not to spend it. I’m saying that I would be happier with $60k yearly from my SaaS, than $120k from dayjob salary if my customers were my boss instead of the asshole who is my current boss. So the answer is $5k recurring monthly revenue. With that I’d be happy to quit.


You'll never know without trying it. Other people's experiences aren't always relevant to you, either.

The only way to understand is to just do it.


Before you do anything, read this blog. [1]

TLDR; he left a high paying job at Google to start out on his own. After multiple products, he’s gone 4-years and still hasn’t made any money (despite the fact he has a business generating $500k in revenue). [2]

This blog documents the huge challenge ahead. Must read for anyone wanting to go off on their own.

[1] https://mtlynch.io/why-i-quit-google/

[2] https://mtlynch.io/solo-developer-year-4/


Why hasn't he made any money if he's generating 500K in revenue?


cost of goods sold, salaries of his staff, etc.

All of this is explained in his blog (he breaks out the revenue and costs by line item)


What I didn't see is any 'expense' for payment to himself? Perhaps it's there and I just can't find it. Paying yourself as an expense then still having 'profit' left over would be different than "I just worked full time for a year on this and only made $14k for myself". I can't tell if it's the former or latter.


If you're asking yourself whether you should quit your job: take a month to plan, then quit your job.


> Quitting job to focus full time on your hustle, what did/does it take for you?

My sanity, social life, and world outlook. That said, I don't regret taking the plunge. Living in corporate drudgery isn't living at all.


9 in 10 businesses fail within the first year. And another 9 in 10 fail the following years. The odds aren't great. Also now your customers are your boss. You don't necessarily have more freedom.




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