On Starting Projects: Finding a Balance Between Iteration & Planning
During the last couple of weeks, I’ve been working on the beginnings of a project that I’m quite excited about. This project is the first time I’ve ever gone to the effort of building something around one of my biggest interests, though I won’t reveal which one here.
I’m not a web developer, and some of my plans are quite advanced beyond what I’m capable of accomplishing alone. This necessitates starting off simple, using my limited knowledge of CSS and PHP to hack together something that does a few of the things I want on top of WordPress (which, despite the odd ideological difference of opinion with the people that create WordPress, I think is an absolutely fantastic bit of software). If the project makes me money at some point in the future, I can hire a developer to make the rest of the plan a reality.
The Dilemma
The question for me now is: where do I stop trying to hack something together that falls in line with my plan and begin the launch-and-iterate phase?
You see, I’ve been on both extremes of the spectrum before–meticulous planner, impulsive launcher. To be honest, I don’t think there’s anything wrong with either approach, really. I know many people will disagree with that sentiment. But if you’re the kind of person who needs something to be really finished before you show the world, so be it (as long as it gets out there at some point). And if you don’t care whether the world sees your project half-naked, then who cares? It’ll work out in the end–as long as you’ve created something that’s useful in some way even in its incomplete state.
This time, however, is different. It’s the first time I’ve tried my hand at a fairly complicated web project while employed. In the past when I’ve decided to do something like this, I was self-employed and could devote business hours not consumed by client work to these things.
With limited time (I’m certainly not willing to cut corners and spend my employer’s time on my personal projects) I have less to devote to the project, and less time to teach myself everything required to make the project work from a technical point of view, which is the approach I used as a self-employed bootstrapper.
The Feasibility Test
So, I came up with a very simple test to determine if new ideas are viable for me to work on. Here’s what you do:
- Determine how much of your plan is possible for you to create alone with your existing knowledge.
- Determine how much of your plan requires the help of others, be they artists, developers, marketers–wherever your weaknesses are.
- Figure out the absolute earliest point in development that you could start to make some income from the project.
Test Result A: If you can somehow make money from your project before the complete plan is implemented, and it’s possible to reach that point with your technical abilities, you know what Version 1.0 of your project will look like. Your project is good to go–build that basic first version, put it up on the web, earn some income, and hire the help you need to get to Version 2.0.
Test Result B: If you can’t make any money without the assistance of experts, you have a few less desirable options. You can go out of pocket and hire help (it’ll be good and fast—relative to the time it’d take you—if you hire right, but it won’t be cheap). You can learn the skills and do it yourself–something that’s totally possible but it’s certainly not fast and will not be cheap in terms of time lost. Or you can go back to the drawing board and come up with a new project or retool your existing project so that it can bring in some sort of income with the tools you have at hand.
Luckily, I think I’ve found that point where I’m able to monetize my project without depending on others. I don’t know how much it’ll make, but hopefully I’ll have enough to cover hosting expenses and hire some help after six months.
When it comes to copywriting and content generation, marketing and running a small business, I’m good to go–but I know my weaknesses and think them through before starting a project. What’s stopping you from starting the project you’ve been dreaming about?


