How do I break free from 9-5 and handle the overwhelming amount of opportunities?

As brief background info, I am a 29 year old self-taught programmer (freelanced for about 3 years using Ruby on Rails) and have been working full-time for the last 2 years doing Ruby/Rails development. Overall, I’ve probably been programming for about 7 years. I generally live alone and don’t have children so have plenty of spare time on my hands.

I am STILL thirsty to learn more… but at the same time, I have neglected important skills that will help me with building a software-based business. Namely, communication skills (leadership, public speaking, persuasion). Every time I think about building my programming skills, I start to think “why”? I am more than capable of building almost any kind of software I can think of – if not, I know I can learn most things. The main reason to upgrade my skills now is for job security and advancement.

Over the last couple of years at a full-time job I’ve realised I just cannot live my life in a 9-5 always wondering “what if” I’d stepped out on my own again and carved my own path. I can’t help but think my earning potential is much larger than my salary.

I know this path will be extremely challenging and fulfilling to me… and so I find myself here.

I could have already gone this road many years ago but I think I gave up freelancing for the security of a job. And I didn’t have security in freelancing for the same reason I will struggle building a business - lack of direction, analysis paralysis, etc.

I am slowly beginning to understand the kind of software and markets I would love to be a part of, and noticing plenty of opportunities around me. I’m also willing to give up some passions for cash-flow purposes so I can get out of my 9-5 sooner and work on my own stuff full-time.

I would love some opinions from people here who have been in a similar situation. About 4 months ago I spent a couple of months building a Wordpress plugin that I was going to sell on CodeCanyon. I identified a small gap and believed I could get a foothold. The plugin would probably take me about 3-4 months to finish.

However, the language (PHP) and platform put me off after a while… then came a flood of more SaaS ideas, online courses, ebooks… I’ve reached a state, like a did almost 10 years ago, of being completely overwhelmed with opportunity.

How the heck do you know what direction to go? I don’t want to hang around in this prolonged brainstorming session for too long, and yet find it difficult to commit to a single project.

7 years self taught programmer and last 5 years doing RoR and you can build most anything? Anyway moving on…

If you’re looking to building a business then the coding is actually a small part - sales / marketing / etc etc etc are much bigger challenges (in time and complexity and most of all uncertainty).

To improve your skills in this area it almost doesn’t matter which project you choose. Amy Hoy recommends something like course/ebook where the production of the thing is deliberately tiny and the work is in ‘all the rest’ so you learn, then move onto something bigger. Rob Walling also suggests similar approach (start small move onto bigger things). Amy also bangs on about “just f’ing do it” which sounds like it might resonate with your procrastination problem.

Other places that might be worth a look -

But of course all of that homework may make your main problem (procrastination) worse.

So back to your overwhelming amount of opportunities problem - just pick one and stick to it. It really is that simple!

  • Visualize your end goal (e.g. “build company to provide full time job income but with more XXX” and write it down where you can see it every day.
  • Break it down into milestones and then tasks.
  • Focus one big thing at a time.
  • Write down the one big thing that your going to achieve tomorrow before you stop work.
  • Set a rule (maybe software) to not look at FB/HK/this site until you break for lunch.
  • There are a million guides to personal productivity. Read a few but don’t fall into productivity porn procrastination. They all come down to “just f’ing get on with it” at some level.

<controversial> Since you’ve no dependents consider getting savings together for X months of expeses and just quitting your job. The dwindling bank balance is a good motivator. “Burning Your Bridges” isn’t always a bad thing.

6 Likes worth a read to give yourself a kick up the behind

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Maaaan, you have soooo much advantage! Use it before it is too late - you know, wives and kids appear seemingly overnight!

Not me. I don’t. I spent 10 years trying different project almost at random. I realize I do not have interest in some of them after a time, some were found nobody needs, some were needed but only as open source.

Eventually I’ve found a project that a) in demand and b) interesting to me. This is where I stick to for the last year or so. So find an intersection between “needed by others (non-programmers) and interesting to you”.

Then actively reject all the distractions! What works for me is to put all new cool ideas onto a special TODO list. This way I kind of trick myself into thinking I may come back to them one day.

Yes, he can. Programming is not a rocket science, and whatever he doesn’t know yet - he can learn quick.

Which (ebook) I believe a crappy advice. It worked for her because she and her husband were leaders in some Javascript area, they had a following and had something to tell (and sell) to those people.

A regular developer is not in the same position. Besides, if the end goal is to have a software business, then by all means, start a small project, but a software project. Then the learned skills will be directly transferable to a bigger software business later.


You missed the point. The point is not that it has to be an e-book - it that it should be a small project that you can finish and then learn all the other stuff that goes into running a business.


Fine, I missed the point then.

To not let others miss your points, make those points big and emphasized :wink:

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If you are struggling with analysis paralysis try:


Instead of thinking about Saas idea, think about the kind of customer you want to serve. Then find what they buy, take the biggest competitor and read all their reviews - you’ll find an underserved angle (for example: This feature is premium plan only for the #1 in my space, let me offer this feature for free to get initial traction).

One hack I always do: First thing I do is hiring part time person to help me with project. Not so much as I want this person to do a lot of work (I hire very part time only, say 4-8 hours per week) but committing some money makes me get the project done.


“7 years self taught programmer and last 5 years doing RoR and you can build most anything? Anyway moving on…”

No need to be patronising and attempt to bring someone’s self-belief down. Obviously I don’t mean I could build almost anything within any sphere of technology and I’ve worked with much more than RoR for the last 5 years. But in terms of web applications - yeh. I work for a very popular Online Travel Agent in the UK. Believe me, I’m fully aware of the vast amount of work that goes into building such systems.

I’m not saying I could build that BY MYSELF. I could quite easily build prototypes and go from there, though. Maybe that would be a better way to rephrase. Either way, keep your negativity to yourself. If your criticism here were constructive AT ALL then I wouldn’t mind, but it isn’t. It’s just a little dig at someone’s self-belief. Well done you. Is that what this forum is about?

Anyway… thank you for the rest of your post because it was very helpful indeed. I’ve been subbed to unicornfree for a while and followed Amy for a while, too. I think I intellectually understand what I should do next, but emotionally I’m being held back – motivation, values, etc.

“Since you’ve dependents consider getting savings together for X months of expeses and just quitting your job”

One other advantage is that I don’t have any dependents.

I’ll do a bit of homework on those links and try to stop twiddling my thumbs so much and just crack on with what I was building.

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Thanks for the advice! I’m going to be ruthless about building an MVP and just getting it out there, fail fast and learn from that.

That’s a great idea. I’ve considered outsourcing some development tasks just to help motivate me and give me a sense of combined direction.

I agree. It’s about building something I can sell so that I can learn about the many other skills required for running a successful product – marketing, sales, customer service, accounting, etc, etc

I can’t know what you ‘obviously’ meant - only what you wrote. And that pretty tame dig may actually be just a tiny little wee bit constructive in that you shouldn’t overestimate what you can actually achieve - otherwise you won’t actually SHIP. Which is pretty near the start line of this little adventure. One of the skills that you will have to pick up if you’re looking at running a business is a slightly thicker skin.

Good luck.

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He isn’t married yet :slight_smile:


Don’t worry, I’m not actually offended for the dig at me. I’m offended at the attitude itself. I’ve seen plenty of people attempt to put others down online and it serves little purpose.

What exactly did you want to get from making that remark? To remind me I am a mere mortal? Did it make you feel better to put me straight? Because underneath my unwavering self-belief in what I can achieve, I am well aware of my limitations.

…and I see no reason to not overestimate my abilities. I can do that and SHIP; they are not mutually exclusive.

Thanks for the good luck :slight_smile: Hopefully, I won’t need much.

You’re fixated with my perceived slight on your ‘abilities’. I’ve been talking about what you can realistically achieve within the constraints you’ve got (which do include ability but also knowledge, experience, skills, manpower, finance, time, industry contacts etc etc etc).

Sure you could decide to develop software for processing LIDAR signals in autonomous cars (as a random example) but if you’ve got no existing experience in related fields, no knowledge of signal processing, embedded systems or AI, no industry knowledge or contacts - then you’ve just made it a teeny tiny bit harder for yourself!

…and I see no reason to not overestimate my abilities. I can do that and SHIP; they are not mutually exclusive.

That doesn’t really make sense… may not exclude, but would make it less likely, wouldn’t it?

Anyway last word from me as I really shouldn’t have bothered at all.

pick something small, even something you can let die if need be. maybe a blog even. get it up and running and push yourself to get a following and to produce the content. it’s all the other stuff that takes the time especially if you have to learn it too.

I think a blog might be a good idea. I did originally work in internet marketing a good 9 years ago and have worked with our marketing department quite closely in my current position. I have experience with copywriting, adwords, facebook ads, GA, landing pages, split testing, email lists, affiliate marketing, etc. etc.

I’m hoping that will at least give me a head start when it comes to expanding into those areas after I have something to sell.

  1. Try to figure out how to filter/evaluate these opportunities so you can confidently choose one and not be distracted. That is no easy task. If it were everyone would make money investing in startups.

  2. The non-software part of the business an make or break you: Which problem you choose to solve, your revenue model, how you reach (market to) your customers) are all huge and you can make a LOT of mistakes and waste a lot of time.
    3.Don’t quit job until you NEED to do so, unless you are HATING your job and can’t find a better one. Your job PAYS you to get more experience. Get a job in the business area you think you’ll solve your problem in. Then someone is paying you to learn what you need to start your business.

  3. Re: “digs as you”. You still seem to be taking personally. That’s understandable but does YOU no good. Every bit of feedback you get could be useful if you dig deeper and ask “why did you say that?”, either they have a valid point (and save you your own mistake) or you find they have not point. Notice that neither of them involves “is this a dig at me?”.

  4. You do not know what you are ignorant about. None of us do. +1 for launching the smallest thing you can just to see how to run an entire business. ++1 for joining small company so you can learn about all aspects of the business. At learn all the stuff you’ll need to make happen to make money.


Why everyone keeps saying that? I’m almost 20 years in Windows desktop software business, and programming (adding new features, improvements, bug fixes etc) still takes more than 80% of the time I spend on the projects. It really depends on the niche. For products where market is overcrowded, the product is relatively simple, yes, sales/marketing can be the main focus. But for narrow niche products, things can be really different.