Going from Freelancer to Bootstrapper

Hi everybody,

I’ve been lurking for a few months, and I always wanted to be self-employed which I’ve been doing for over 2 years now. Things are going great, I have a few nice clients and projects, decently payed, etc. I couldn’t be more happier about the simple fact that I ride my own thing and it feels great to achieve victories by myself but lately I’ve been feeling more and more like I was wasting my time.

Instead of climbing some organization’s ladder and get life insurance and all kinds of long-term benefits I’m working on my own, gaining experience but nothing more really. The main goal when I left my job 2 years ago (I’m 26 btw) was to start my own thing, have my own team and live the dream but it ain’t simple like that as you must already know.

Now I’m stuck between a few options:

  • Keep getting contracts via Internet, work by myself (what I already do).
  • Get more local contracts and make my own development firm (I have a few nice contacts and past colleagues, it shouldn’t be too hard). I’d offer website, application development, etc but that’s not really what I wanted but still cool IMO.
  • Bootstrap my own idea, develop it and try my best to monetize it.
  • Go back to a boring office job, defeated and stuck at the bottom of the ladder.

In a perfect world, I’d bootstrap my own thing. That’s my dream, that’s what I wake up every morning for but unfortunately there’s always something more important to work on so I end up letting my ideas rot on GitHub.

I’m a technical person but I believe in my “people” skills as I already made a few sell myself a few years ago and I feel great doing it. I just lack confidence right now as I’ve been stuck inside for 2 years hehe. I don’t know wether or not I should find somebody to start something with or do it alone. Maybe finding a mentor could help me focus on what I should really be focusing on?

I’ve also registered myself to a few local entrepreneurship courses, so I can meet people, find new pains to work on and learn more about this whole new world I’m looking forward to. The thing is, I have a very hard time finding the right idea to work on. I’m trying to do market research, finding pains, reading about people having a hard time getting their things done, finding something I could make better. I’ve got skills, I’ve got a ton of experience, I could develop pretty much anything I want on any platform but I don’t know what to do at all. As time goes by, I feel less and less motivated and that I should make a move as soon as I can before “it’s too late” which means absolutely nothing since I guess I’m still rather young hehe

Anybody feels the same? Anybody went through something similar and finally got it right? I really want to build something, I’m a sucker for perfectly tailored code and user interfaces, I’m all about user experience, all I need is something, somebody to help me push me beyond my boundaries.

Thanks all and have a nice day!

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Mentors and courses won’t help your motivation and confidence problems.

Just build something. Then see if you can get people to use it. Then see if you can get people to pay for it.

The small wins are addicting and you learn new skills along the way.

We like to get all scientific about “the process” and “how I did a successful launch by doing xyz” blog posts and podcasts but I think 90% of that is because people are selling you an info product or have a saas on saas product.

Build your future product success brick by brick. Products are a long play and success should be measured by how well you’ve prepared your future self for success.


How do you get them :smile: ?

I would suggest picking one of your ideas and just start building. Show off anything you have early to potential customers and let this stear you. Alternativly go on and build a landingpage which explains your idea and collects email adresses. This gives you a measure to see if there is any demand for the product without spending a lot of time building.

Best of luck!

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First, you’re not alone. Most freelancers go through this transition from working project-to-project into something more scalable at some point. Sounds like you’re there.

I agree that it’s always good to build stuff, learn by doing, and gain experience in doing things other than client work.


You’ve got to be smart and strategic about it, especially as a bootstrapper.

I’ve been writing in depth about this stuff lately, but here are the bullet points:

  • Look at a Productized Service as a potential first step into a more scalable business model.
  • Start with something (one thing) you’re already doing (especially something clients are paying you for)
  • Find creative ways to streamline, while providing even more value to the client.
  • Over time, you’ll focus more and more on processes so you can systematize and automate your operation… Freeing you up to focus on growth.

Here’s one of my recent articles about this:

Feel free to reach out if you want to talk more.


Honestly I think it takes allot of discipline to make the transition. Once you have a freelancer/consultant mindset, you now calculate everything based on your opportunity cost.

Say you have some downtime, so you start building your side project. Then you get this big juicy opportunity and you jump on that new contract for the next few weeks/months. When you get time again, you start working on your side project but now with a little less excitement. Some time goes by, and now you see competitors adding all these new features, techcrunch is now reporting that they just received a few million in funding, etc. Now it has been 6+ months and you haven’t shipped and don’t even have your server ops side of things nailed down and you are hitting a hard point in the application. Now you begin to really doubt yourself, a few new contracts come in and now you are thinking to yourself…maybe this isn’t such a good idea anyways. I need a new idea, yah that’s it my idea just wasn’t suitable… FAIL!

Having said that it is still very possible, I’m just saying most people won’t get past these hurdles.

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Hey Tommy. Is there some kind of product or tool that you could build which your existing clients could use?

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A couple of hopefully useful points:

Do not make the mistake to “monetize” something: instead build something that provides value and charge for it, straight away. I warmly recommend Amy Hoy’s 30x500 course for a safer path for this. From your age roughly, I made many attempts to “monetize” many sites, until I moved to a “real product”, and I really should have started earlier.

Make room for your future product in your freelancer life (I detailed exactly how I’m doing this in this article). Make sure to find a good balance between your future product and your current freelancing situation (see my little bootstrapper calculator here).

Finally: things take time to boot. A lot of time quite often! But you are young and you have a lot of time ahead. So make sure you enjoy life in the process, make sure your finances are in the clear, and invest, invest, invest.


Sorry for the more-than-late response but I just wanted to thank all of your for your precious advice!

I read a lot of good stuff in the thread and I’m happy to feel myself ready to build something, stop thinking about it scientifically and just go with my guts and clients feedback on my ideas. I need to stop being concerned with everything before even starting and just build away.

I’ll post an update whenever I get something done and ready to show. Feel free to message me anytime and thanks again!

Why are these mutually exclusive?

I’m a freelancer and I get my work both online and locally. The work is the same, just the way I get it is different. I think it’s a good idea to have more than one channel through which you get work. See this post of mine: http://www.jasonswett.net/a-rough-picture-of-my-marketing-system-for-ben-franklin-labs/

As far as bootstrapping goes, you have that listed as an “option”, but it’s probably only something you can do on top of one of the other things, right? You still have to have income somehow?

I’ve been struggling for a long time to make time for my product business on top of my consulting business. I’ve tried setting aside a day a week, which didn’t work. I’ve tried setting aside an hour a day, which didn’t work. The product never “made the cut”. What finally ended up working for me is when I decided to dedicate the first hour of every day to my product.

I would also recommend not letting anything hold you back from getting started, not even not having an idea. If you don’t have an idea, make a list of 20 terrible ideas, pick the least worst one, and work on that. You’ll eventually learn something and get a better idea. I did this with 5 different business ideas, then the 6th one made money.


Chiming in again here because it’s something I really relate to (and I think a lot of us do). This transition is super hard and takes a looong time to truly figure it out.

As a bootstrapper, you’ve got to be smart about how you allocate your time. If you want to change your business, you have to be strategic about it - both in terms of what you will do (software, productized service, saas, etc) and how you will make the time to make this change happen.

In other words, you have to work on your business instead of workng exclusively in your business.

Here’s a more recent article I wrote about a few things that helped me make the Time to transform my business over a number of years.


  • charge more (so you can work less and make the same, freeing up time to build something new)
  • wake up earlier.
  • don’t try to do everything all in one year
  • start simple (but be strategic)