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28 Comments

The early bootstrapper dilemma

I want to talk about a dilemma that crosses my mind frequently because I imagine more people think about it. I'd like to know what's people's approach to it.

As a bootstrapper with technical background with a couple of projects making around 200€ / year in total, I see a few ways to make money:

  • Double down on existing projects. Mainly do marketing.

  • Build new projects.

  • Do freelance work.

  • Get part time job.

  • Get full time job.

From first to last they have increasing expected money generated. The also have decreasing freedom, which is why I want to bootstrap my own projects.

The dilemma is how to choose between those options, or even a combination of them.

I mean, I could double down on existing projects and maybe reach 1k/year, which is not very good. I could spend a few months trying to make something else work and probably stay in the 3 figures or low 4 figures by the end of the year. At the other end of the spectrum I could get a full time job and maybe make somewhere from 80k to 150k.

My approach so far has been a combination of freelance work and building new projects. But I feel not putting enough energy on the new projects they won't work, and I'll be stuck on this stage for a while.

At the same time I think about the amount of money I'm leaving out following this indie hacking life. Is there a point where it makes sense to look for a job?

To wrap up, I'll leave here two memes from Dago that illustrate this dilemma:

- Software engineer quits a $300k job to follow their dreams and build a startup - Makes $50 in 3 years

– How did you end up in poverty? Gamble? Drugs? – I quit a $100k software job to build a startup.

on February 1, 2023
  1. 5

    This dilemma is difficult to discuss about in the sense that everyone's situation is different. Some of us have multiple kids, others don't. Some of us have accumulated enough wealth to "play" a bit, others haven't. Some of us are at ease with taking risks, others aren't. Some of us can still stand having a full or part-time job, others don't. Some of us are ~20, others are 30 or 40+yo. Some of us have tons of friends and need to socialize a lot, others don't. The list is endless :p

    I have 3 kids (one of which is ~1.5yo), a mortgage and fixed costs I have to take care of each month. For me, going full-time on my indie dreams is way too risky. I chose that path for a while and ended up failing "miserably" (https://www.dsebastien.net/2021-01-04-20-months-in-2k-hours-spent-and-200k-lost-a-story-about-resilience-and-the-sunk-cost-fallacy/).

    But at the same time, working full-time is not an option anymore, having tasted real freedom and energy of working on my own projects. I still work half-time as an employee as that covers for my fixed expenses and provides security for my family. I also work 1d/week as a freelancer to cover the costs of my company and build a safety net. That leaves me with 1-2 days of indie hacking a week, which is pretty good for now. It allows me to keep going, even though I have to fight against procrastination and other obligations during those days.. ^^

    1. 2

      Yes, absolutely agree the right answer depends a lot on every persons situation and preferences. I was curious to know people's approaches to it and the reasons behind them.

      It looks like your current situation looks a lot like my ideal one. How did you get that part time job? I think that's what I'm missing to get the ease of mind of not having to touch savings.

      1. 2

        I scaled down the full-time job I had for 15 years. They trust me and they're still happy with what I deliver working half-time. I'm lucky and grateful for that!

        I progressed quite a lot within the company before switching, so my half-time salary is quite good (not FAANG-like tho :p).

        1. 1

          Full time to part time transition sounds like a great way to go into part time. Even if not a FAANG salary, being able to not use savings with a part time job sounds perfect to me! haha

    2. 1

      That's quite a detailed & honest story of your journey Sébastien. And it is immensely helpful.

      I have done something similar for a product that seemed to have a lot potential, and will clients during the C19 days. I had to kill it due to regulatory changes here.

      These days, I'm more into 'small bets'. Not spending more than 4-6 weeks on any project until I see some money in it.

      1. 1

        Fully agree with you. Small bets for the win!!
        I wrote about that a while ago in my newsletter: https://www.dsebastien.net/developassions-newsletter-small-and-riskless-bets/

    3. 1

      Just read your post ... do you have a follow up? Did you get anywhere with that startup or have you switched to something else?

      I feel like I'm in a similar boat ... working on a couple of projects but finding it very difficult to get any traction. Wondering whether it's the right path!

      1. 1

        Yes, there's a follow-up post: https://www.dsebastien.net/2021-02-28-21-months-in-and-80k-views-later/
        I didn't publish much regarding that story afterwards, but it didn't end well. Got nowhere, abandoned it all, and the IP is "in conflict", so I can't reuse much from what I did during that whole period 😂

        But I'm well over it now, life's good! ;-)

  2. 4

    This is certainly a dilemma that has crossed most of our minds. I have always built tools on the side, but as a father and a husband, my first concern is always making sure that I am providing well for my family, which means that I interpret the list from bottom to top, ranked by "security" (of our lifestyle), rather than by "freedom". I think the fact that I am always building, even on the side, keeps me sharp so that I can make the switch when the time is right. As with most things in life, I don't think this decision is black or white; there exists a happy medium.

    1. 1

      Father and husband here as well, although father just recently. Which I think contributes to thinking about this more often lately.

      I used to prioritize freedom, but I think at my current income level I still need to use savings. So I'm open to a combination of options from the above. However, I'm not sure I could go back to a full time job.

      Having something on the side is something I don't want to stop doing, but I don't think I'd have energy to work 8h, some more time on a side project, be with my family & friends, and workout.

      How much time do you spend on side projects?

      1. 2

        Good question :). I pretty much spend most of my time that I am not with my family, working, or sleeping on "side projects". But my side projects go beyond digital work. I own some rental properties and a couple of small businesses that take up some of that time. I spend a lot of time learning and researching, not so much creating.

        I do have a product that I created for myself and that I use pretty much on a daily basis to keep me on top of all the responsibilities -- but I haven't really made any improvements in a long while; I think it could be improved and monetized.

        I recently (like 2 weeks ago) started the research and prototyping phase for another product that I really need. One of my businesses is an event venue that we rent out for small parties/events (soon to open a second one). It's a simple business, but it keeps me busy and includes a lot of manual work like managing customers, contracts, invoices, payments, receipts, reminders, and events. I have tried countless CRM products, but haven't found one that is affordable (under $50/mth) and is really made to handle this type of business. I will be embarking on a quest to create something that will solve this problem for me. Perhaps it could become a business instead of just a personal tool.

        1. 1

          Thanks for sharing!

          I think the problems you face as a company are probably a great starting point for starting a business. It sounds like you're doing just that, and making it in a way that can be monetized sounds like a very good option here.

          Not to be confused with the problems you face NOT as a company. Many times I've thought "it would be great if X existed", but B2C things like that are too hard to make it work. Maybe the exception here would be if you're part of a niche that's looking forward to spend $$, but I feel that's the minority.

          Good luck monetizing the solutions to your own problems! :)

          1. 2

            Thank you Daniel. Good luck on your journey as well and I hope you find your happy medium.

  3. 2

    I can completely relate to this. This was my dilemma as well.

    At the same time I think about the amount of money I'm leaving out following this indie hacking life. Is there a point where it makes sense to look for a job?

    I left a well-paying job at the beginning of this year, and I'm experimenting with building my own stuff.

    This is what I have decided -

    I'm going to treat this entire year as a year of experiments. This is when I'm planning to do -

    • Find part-time/freelance work for some assured income. I'm not committing more than 10/15 hrs/week for this. (Any takers? I'm available)
    • Build projects, put them in public and see which ones get some interest/traction. Double down on what is working, dump the ones that don't work.
    • At the end of the year, if I make 35% to 50% of what I was making while working in a full time job - I'd happy and won't go back to a full time job.

    Indie hacking or entrepreneurship won't work in a linear fashion. But they have tremendous potential for compounding your efforts. So in 2-3 years, it is possible that one successful product you build can earn you multiple times your full-time job.

    Moreover, as you have rightly identified, it is about the freedom. Building stuff you want, on your own terms, and earn some money from it. If you're happy with the returns - it's worth trying IMO.

    That's what I have set out for this year. :-)

    1. 1

      Yep, that's kind of what I'm doing at the moment. The only problem is point 3, where I'm making about 15% of my full time salary from 2019.

      Compounding and freedom are the two things that make me continue on this path, at least for now. And with compounding I don't necessarily mean compounding with a given project, but more with my growth. I'm learning a ton, getting to chat with very interesting people, and in general increasing my exposure to luck.

      But all that is not tangible and hard to put in terms of $$. Is that + freedom worth what I could be making in a full time job? That's the main dilemma for me

  4. 2

    That's really true, Daniel. It's quite hard to make people pay money for something. Requires constant feedback & experimentation.

    I also personally know of 1 founder who quit his job and was building a SaaS in the social listening space. It didn't generate any revenue for a year. So he went back to a job only to quit it again in 2 months as he hated working for someone else

    But during that time, after he quit, he started making around $1K in a few months. Currently he's at $7k MRR.

    One thing which is evident is that it takes a lot of time to build trust with people especially when we're first time founders

    1. 2

      I think I'd also hate working full time for someone else. Part-time could be different because I'd be able to do side projects with more energy, spend time with family & friends, etc. But I'm not 100% sure I wouldn't hate it as well haha

      That founder you mention, did he continue working on the same project on the side? or did he start a new project that took off faster than the previous one?

      1. 2

        Same here, Daniel. I'd hate working full time too.

        So he was working on the same project :)

        1. 1

          wow amazing that after a year not generating revenue it only took a few more months to start making $1k!

          There's a learning right there. I might have just killed the product, and with that the $7k I might be making in the future 😬

  5. 2

    Building products without revenue is very much risky process. If you don't have any runway left in savings, I would highly suggest you cut down on the number of side projects first. The best bet here would be to get '1 Full time job' and then pick 1-2 side projects and see how far you can go. Once you comfortably goto $1K MRR, then you can think about quitting full time.

    Some other alternatives you can think about - Start writing any Newsletter, Building quick info products, Building a productized service etc.

    Between, if you need more inspiration, pointers, trends around SaaS projects - Micro SaaS Ideas Newsletter could be a good starting point.

    1. 1

      Thanks for the link! Just subscribed 🙌

      I still have plenty of runway, which I think it's part of the problem. I'm at that point where I need to use savings but not much, and at the same time I don't see a hard deadline that makes me go all in. I'm not sure if that makes sense, but I feel having less runway would make me act differently.

      I'll look at the micro SaaS ideas and see if I get some inspiration :)

      1. 1

        Regarding the "plenty of runway" problem: I faced a similar problem. If I had less runway, I would have got a stronger "urge" to be successful again with my projects. What helped me get on track despite the runway:

        1. 10 hours a week work in a supermarket. Yes, such a job has horrible pay. But it gives me MORE energy to work on my projects and it balances out all the time I spend in front of the computer.
        2. Finding a team - I'm working with two awesome guys and with one of them I even work together in-person all the time.
        1. 1

          Those are good points. Creating incentives to focus on the projects are a great idea, even when they're negative incentives like working in a supermarket. I'm not sure I'd do it because I feel those 10 hours would be time lost, but definitely interesting to investigate the negative incentive concept. Maybe there's even room for a product here 🤔

          As for finding a team, I've done a team and a solo project before. The team I feel we had overlapping skills and missing ones. And as solo founder I could definitely use some help. Next one will probably not be solo, although I'm more aware of skills I'm lacking. First in the list: marketing.

  6. 2

    This is pretty much my dilemna as well. Its a little bit difficult to find a part-time programming job, but maybe teaching could be an option. I might try offering hourly programming coaching sessions for people who are new to programming. It could have more flexibility that way.

    1. 1

      Hmm I hadn't thought about teaching, and I believe I'd like it quite a lot! I've already done some (free) mentoring online and with friends who were switching careers into tech.

      As for part time programming jobs, I've been told these could work, although haven't tried myself, yet. Sites are

      They are companies filtering devs, and their clients are other companies looking for vetted devs.

  7. 1

    Depends on your family situation.
    If you can invest your time on your own startups — why not to do it?

    But if you can't you don't have a dilemma.

  8. 1

    Hey guys, I am in the same dilemma.

    I have a full-time job well paid but want to pursue my own dreams but I am not ready yet to pull the trigger. Not sure what holds me back, the worst case really for me is to find a new job if things don't work out

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