How To Know If An Idea Is Worth Pursuing

I’ve been on a partially unplanned hiatus from this blog (and in fact, all of my writing endeavors) for a while. It’s good to be back.

Since I wrote The Wantrepreneur’s Blues, an article where I complained about not having any good ideas to work on, I’ve had an influx of ideas for things I could be building. It seems that actually cured part of my writers block, because whether it’s from Twitter, Facebook, some random uncles, or my own head, I’ve built quite a few Trello boards spun up with giant lists of tasks to complete, generated from this influx of idea capital. This, unfortunately, puts me in another predicament I described in that article: there isn’t enough time in the day to move forward on all of these.

So how do you pick? You could just list them out, start from the top, and start working. Maybe list them alphabetically, ideas that start with A are better than the rest.

It’s actually a pretty hard question. We know that some ideas are inherently better than the rest. Any software engineer can tell you that: we weed through terrible “great app ideas” at every holiday party. It’s become a meme at this point. So how do we decide what we should be doing? Is it just a feeling? For most of us, probably. We work on the project that we like the most, or that we think has the most upside, or some other nebulous characteristic. But I think we can be more analytical than that. Maybe we can come up with an algorithm that shows us the way.

So first things first, I think it’s important to note what “working on an idea” actually is. I think it’s something that needs to be defined: it’s not just building that trello board and staring at it. Changing the background colors and tags around does not constitute work. Thinking about the idea does not constitute work. That’s an important distinction, as it has gotten me stuck on projects that I think that I’m working on, but have actually died out long ago (RIP, I’ll come back for you). I’d go through my days saying “oh I’m going to work on that tomorrow”, “I just need to figure out this issue and then I’ll move forward. I’ll get to that this weekend”, “Maybe the solution will come to me if I take a nap”, and then never do anything. So, what does constitute work?

Ideally, you should be able to complete something that moves you towards your end goal every single day. If you’re not moving forward, you’re falling behind, and if you fall behind too much you’re just going to give up. We have to give our future selves a fighting chance, and that’s done by making a commitment towards a goal, and then acting on that goal in a consistent manner. Obviously, ideals aren’t always reality. You’re going to get sick some days, or you’re going to be forced to work on something else. Sometimes you just need to take some time off your projects and clean your apartment (I’m reminding myself of this right now). Lets not get too far into ideal work habits: that’s a post for another day. The point of this is to tell you what your side project needs to survive: Actionable Tasks.

So lets start weeding through ideas, shall we? First thing we should do is write them all down somewhere, and define what the “end” state is. I know that no project is ever truly “finished”, but figure out what that project looks like where you could reasonably say that you brought the idea into reality. Amazon likes to call this “starting from the press release”: figure out the end goal, then we’ll figure out what we need to do to get there. This should weed a few of your ideas out already: some ideas are just nebulous creations, vague and unsuited for action. I would say throw these ideas to the bottom, and then later brainstorm on it and figure out the details. Or just throw them out. They might just be shit.

Next, take a little bit and map out tasks that will move you towards your goal. I think you should time-box this: maybe take an hour for each idea, just so we don’t get caught in analysis paralysis. This would be where you map out features that need to be built, and other background tasks that would need to be completed for this whole thing to come to fruition. For example: I need to build feature A, B, C, I need to find hosting, build a landing page, get a logo made, come up with a name, think up a social media plan, so on and so forth. These should be mid-level tasks, meaning that they’re specific enough to be actioned upon, but could take a week or more to do. The list need not be complete, it’s hard to know every single task you’d ever have to do, but it should at least give you a good idea of what you’ll be working on if you decide to jump on this idea. Some of the tasks could be “figure out how to…”. That’s perfectly acceptable, but tells you that you’re not quite sure how to make this thing work.

If you can’t complete this list to an acceptable degree, then again the idea is just not fleshed out enough to be viable. What’s “acceptable” is entirely up to you and how you feel about your skill set in the area. How confident are you in yourself that the “figure out how to’s…” are not going to derail your progress? How many “hidden” tasks do you think might not have made it onto your list? You need to rate each of your ideas with a degree of uncertainty. This can just be a ranking from 1-10. I’d say throw out anything that’s higher than a 5 or 6.

Alright, so you have your ideas, you’ve mapped the tasks, you’ve ranked them. Just take the top one? Maybe. But I’d say there’s one more step. You’ve detailed out the project goals: what would turn that idea into a real life product. But the final step is to figure out your personal goals for what you want to achieve, and how each idea furthers those goals.

For a lot of us, the side project idea is about making a little extra cash. That’s certainly a fine goal, but there’s other goals too: maybe you want to learn about blockchain, or maybe you’d like to scratch your altruism bug and write an open source project. Maybe you want to write a book about something you did, but you need to do something first. Maybe you have no goals for yourself, and are wandering listlessly through life, trying to find meaning in a bleak and meaningless existence. I don’t know! But you should, and if you don’t, now is the time to figure that out. Remember, the ideal is to find something you can move forward on every day. So what do you want to do every day? Why? Figure that out, and rank your goals.

Now, rank how your project ideas match up with your personal goals. Choose the project with the least uncertainty that matches up the most with your most important goals. I haven’t figured out the exact math here yet, but I think it’s almost certainly there. And there’s our algorithm.

With this in mind, I’ll now talk about the reason for my recent blog hiatus: is a new twist in the money management and budgeting app space. I’ve found that while a lot of competitors have great apps for viewing account balances, managing budgets, and seeing spending habits, none of the major players really focus on how to get money back: with rewards programs. Witsi is based on the assumption that if you manage your spending correctly, using the correct accounts for the correct purchases, you can pay less for items, get cash back, and even get full vacations entirely paid for, and all by buying everything you were normally going to buy anyway.

I love finding “life hacks”, or cheap ways to turn a system to your advantage. I think counting cards in casinos is super cool. And I also love helping people do the same things I do, so this project piques my interest. I also, due to a number of previous employment duties, understand credit cards and how they work in a way that I would say 95% of people do not. So, using the above algorithm, I ended up with a project that I have a high certainty I can complete, and a high mapping to my personal goals and skill sets. It was a no-brainer. We’re going into a beta test very soon, and I couldn’t be more excited.

What do you think about this method? Any other steps I should include? Let me know on Twitter or Facebook. Also make sure to follow @witsidotco on Twitter and Witsidotco on Facebook for more updates.


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