The Programmer Entrepreneur Dilemma

Interesting post. I've been thinking lately about the relationship between the drive to create and the drive to master new technologies. I think all programmers experience both types of motivation, but in different proportions. The risk that Dan describes here is a real one - you can become so enthralled with creating apps that you lose your focus on mastering technologies. The opposite extreme can happen as well - you become a master craftsman, but you lose your interest in imagining and creating new apps. The latter is probably more employable, though the new "developer driven culture" I've been reading about lately seems to put a premium on the former.

At the extremes, you do meet some interesting characters (and some hair raising examples of over and under-use of technology). Some people are so antsy to create an app that they just can't stop to learn good practices. These folks learn just enough to implement in the moment, and it's hard for them to pull themselves away. Expect embedded sql in PHP to grow to thousands of pages. Then you get the people who are so interested in a new technology that they almost don't care how or where they're using it. Expect GWT and Guice to render simplest of web forms. The place where these two extremes clash the most is testing. App creator doesn't slow down long enough to write tests. Craftsman says that if it isn't tested, it's broken.

I have to admit that I lean toward the "create now!" side, though I am motivated through a combination of love of craft and personal shame to put some time into good design and testing ;)

You're going to hit diminishing marginal returns on learning new programming languages. Learning entirely new skills is probably far more valuable at kickme444's level. The situation can probably be framed as an exploration-exploitation tradeoff, in which getting more depth of programming knowledge is exploitation and picking up new skills is exploration. Though exploration is typically blind; in this case, kickme444 is experiencing direct demand for his new people/product skills. So I guess my two cents is that he's making the right move.

I'm currently reading Founders at Work by Jessica Livingston (http://www.foundersatwork.com/), and one of the stories seems to apply to your dilemma.

If you have the chance I would suggest taking a look at chapter 3 which discusses Steve Wozniak's early days with Apple. He talks about his hesitation to leave HP where he was an engineer. At the same time, Jobs was pushing him to come over and work on their new venture full time. It wasn't until Wozniak realized (through a conversation with a friend) that he could move to Apple and continue to be an engineer did he agree to make the move. In the end, Woz knew he loved being an engineer, and he didn't think that the time and effort it would take to run/manage a company was something he would enjoy (in fact, he knew he would not like it).

It sounds like you love learning new programming languages, something that is not afforded you in your current venture's structure. Maybe you should consider bringing in a partner to help you manage the business while focus on programming. Or maybe you should hire a programmer to handle the routine stuff for your site. Either option could free-up a considerable amount of time that would allow you to again spend some time each week learning something new.

I'm not sure if that is an option, but it is something to work towards maybe.

I've found that I keep coming across tradeoffs like this, though mine are more pronounced. My whole life I've been obsessed with music, I'm quite a good musician personally (studied it at University) and still really enjoy it. The problem is that I'm also really into business and startups and, through the former, have become quite obsessed with learning as much about web development as I possibly can. This has eaten up a whole bunch of my time and taken me away from my work as a musician and a recording engineer. I'm still trying to balance the two, and then within the startup side, balance being a dev and a business guy.

It's certainly not the easiest thing in the world, especially when my artistic passion is not so related to my startups - though some of the skills transfer. In the end I'm just trying to make sure that I allocate at least a few solid hours each week to just playing/writing and enjoying music. It feels like a relationship to be honest, but I guess this is what most artist's have felt at some point when they realised that they were also good at and interested in something that would help them earn money.

Are there any other HNer's who are artists (of any form) and running startups? How do you guys balance your time?

I have the opposite problem. There's always a new programming technique I could apply to make my product give users a better experience. It's hard for me to act according the the idea that a good product is only one ingredient in a successful business, even though I know it's true. Programmers want to program.

All of the non-tech readers are drooling, thinking

'Oh, don't worry about learning all of that business strategy, customer acquisition and marketing stuff, you can take on a friendly MBA to help you out with it!'

How do I know that they're thinking this? Hmmm.....

It depends on what you want out of Redditgifts. If it is a "project" then you can continue to hack around with new technologies but if you want to make a business out of it then probably you should use the tools which you have already mastered (in your case python). Creating a business itself is so demanding that shifting your focus on "newer" technologies (e.g. node.js) will make it twice as difficult. One approach which you can take is to use the technology which you know well to create critical business components and for housekeeping (metrics, analysis etc.) use the bleeding edge of technology.

I think as a programmer (employed or freelance) you have to improve skillsets in two areas: technical and business. Technical is what you focused on mostly, now it's time to brush up your skills as a business-dude. By starting your own project, venture, startup you will eventually learn first-hand what your current and future employer expects/values of you.

Running my own (bootstrapped) start-up helped me a lot in becoming a better freelancer (and probably employee) - I do freelancing for some beer-money. Once you pay somebody to do something for you, you see the little and big things that an employer values. You also realize that your code is essentially just another part of your company, that has to make money. You will also see if it really matters if the project is written in python or in clojure/scala/node.js.

My problem seems to be the opposite. I spend any free (non-family) time working or tinkering on side projects so I don't get to learn new things like Objective-C or Ruby. Things that I have been interested in for awhile.

If I could get a paying gig on a new technology then I would be golden :)

I have spent about the same time honing my skills in this field, but rarely have I had a clear direction. I've rather just done stuff that I found interesting, which may or may not be directly applicable. Not really related to you main point, but I'm intrigued by the seemingly very different approaches we have.

In my experience, programming is only partly about computers and much more about the reality that you try to model with them. Understanding this reality requires knowledge that people will usually not label as "computer skills". So don't be afraid of picking up some knowledge about how businesses work - It will certainly make you a better programmer.

It is fantastic to learn, but at some point it is also time to do.

> but I worked off hours learning new technologies and programming languages

I don't count that as work. It's rather recreational.