Ask HN: How can I pick a side project and stick with it?

1) Write down a clear S.M.A.R.T. goal or thing you want to do on a piece of paper (OKR style), a clear definition of why you are trying to do the thing, and when you should have it accomplished by.

2) On a separate piece of paper, define your expectations around how chasing that thing will feel and what you expect to happen when you accomplish it

3) Put the second piece of paper about expectations in a paper shredder - destroy it

4) Create a google doc (or whatever) with large bold letters at the top: My goal is to do X by Z because Y. Make accessing this doc as low friction as possible (a bookmark icon on home screen, a bookmark in browser, etc)

5) Create a consistent schedule (1 hour every other day?) and use the doc to track. Treat this as your personal standup doc: make entries on the disciplined timeline, and plot out next steps at the end of each entry. Review weekly (Sunday night?), take notes on your progress, etc.

6) Finally, at the target date, reflect on where you are, and celebrate anything and everything that happened as a result of your feeling inspired by an idea or goal and making tangible progress in your life because of it. It's beautiful.

For the progress doc, viewing your progress makes it harder to give up on - think of it like “We’ve gone 100 days without a workplace accident” or “I haven’t had a X in the last 50 days” - you build up momentum and commitment to seeing something through for the sake of not letting down the older version of yourself i.e. You make quitting an increasingly bigger deal.

Regarding expectations - of course, I'm joking about steps 2 and 3. For me, living life chasing the vision for something gets in the way of actually getting after it, because by definition it's dreamy, and each step you take closer that doesn’t resonate with the dream is another kick in the pants. Soon, you give up and move on because the dream (expectation) is significantly different from the actual experiences you have while taking steps towards it.

For goal setting, I cannot stress the importance of setting S.M.A.R.T. goals and detaching from the dreamy stuff. If the vision is truly powerful and meaningful to you, it will be kept alive and supported by material success on the smaller milestones that you accomplish.

Also, make a plan so you see an end. Doing something without figuring out when you will quit is a sure way toward quitting before you get anything accomplished.

It is indeed irritating and confusing at times. I like to do many things and explore new ideas. Curiosity takes me in different direction. At times, I question my personality and character. Perhaps the feeling of "curiosity killed the cat" is applicable when we are feeling this way.

But let's reframe this!

What if we start to accept this trait, not as a flaw, but as a part of who we are? Once you come to the realization, you start holding yourself accountable.

I have been working on a side project (www.wisecharlie.com) for almost 3 years and continue to do so for many years to come. To give you a background, I am a developer and I enjoy the creative side of code and design. So, it is natural for me to keep exploring new ideas, but I also know the importance of execution. Following are the ways I have held myself accountable to this particular project:

1. No expectations (goals) other than a form of exploration.

I have a revenue generating product, but that does not mean, my goal is to sell the most I can, get as many people to come visit my project and get the most sign-ups. I care about the topic, constant work-in-progress and iterate over it periodically. The process itself brings me joy.

2. Sticking to one project at a time removes a cognitive load of finding new ideas.

For some, creative block is a real thing. From the creative standpoint, I have built the website using plain JS/HTML/CSS, then built the blog using Gatsby. I wanted to learn about webflow so I re-built it during Christmas. I don't have to think about new ideas every time I want to learn something new.

3. Incremental steps as opposed to a giant leap.

I assign myself one task at a time on a monthly basis. That is it. I don't set ambitious goals of 100k users or any of that. This has allowed me to work on this project for over 36 months without feeling burnt-out. It is a turtle race so take incremental steps and make frequent progress as opposed to a giant leap. If I complete my assigned tasks, I allow myself to jump on to other ideas. This allows me to stay accountable and execute consistently.

4. Pick a hobby that has nothing to do with side project.

With lack of human interaction amid global stay-at-home orders, I find myself to be draining my productivity (rarely, but it does happen). To fix this, I picked up on sketching because I wanted to forget about everything that is happening around me. Sketching helped me with that because if I don't focus, my shapes don't follow the desired form. Here is the link to my sketch work https://twitter.com/mihirchronicles/status/12160752161594859....

I am sharing these resources so I can share real cases from my own life and inspire you to take steps that may work for you. Good luck! It is okay to feel how you feel, but I would suggest you to make incremental steps, define your process and take a long-term view.

The advice I share took many years of learning and doing. Curiosity brought the cat back and you can too! :)

Cheers and stay safe!

Once I got a rough prototype to the point where I was able to get value out of the software as a user, the project seemed to stick.

I naturally return to use the software every few days or weeks or months (because it is useful), and when I do, sometimes I have ideas for improving the UI or what's going on under the hood. So sometimes I knuckle down and spend a day or two enhancing it.

In other words, I worked on them and developed them to the point of usefulness because I actually needed to make use of them.