Building a new website, app or any other software as your side project should be fulfilling and enjoyable in terms of learning something new, gaining accomplishments, overcoming challenges and even in the greater sense of finishing “the damn thing”. Many hurdles and pitfalls await those daring to go forward, no matter the role. To a greater extent those who are so inclined to do it all alone and juggle multiple roles at the same time.

If you’re a one-man show, a renaissance man, a polymath of sorts, you probably won’t enjoy both sides the same – even though your love might change from project to project, like mine tends to.
While the actual work a designer has to do might vary drastically from the development side, both may tend to drift towards adapting a similar mental approach, ingrained through a long practice of working for clients. “Do the easy parts first”, get in some quick wins and deliver results for stakeholders – in this case you. What could be so terrible about this method? Isn’t this what they told us agile is all about?
Agile demands results, but Agile needs happy people too.
A happy, joyful and excited team is the fuel that keeps projects running long-term. Choosing to run with an easy-first mindset could possibly hamper anyone in the not so distant future and bring everything tumbling down.
Imagine we’ve started to walk down this road of effortless victories. After some undetermined time all easy wins were won and quick results delivered. What now? Time to put your head down for the real grind, as everything gets tougher and unbearable for increasingly minor gains. Prepare to buckle down! Regardless of your tolerance for frustration, your self proclaimed anti-fragility, the work isn’t just exciting anymore.
Some get hit by it sooner, others later.
This is the place where many side projects ultimately die. They vanish into the distance and move further and further away as you start to find increasingly less motivation to actually do the remaining work. Weeks become months and you start to only remember your tasks vaguely. Like a dark creature in the foggy distance, it waits for you. It deeply knows you and after some more months the creature turns into yet another actualised confirmation on how bad you are at your craft. You drop the project. It won.
Why not start over? If only you could just dig deeper and find the next “real” challenge to embark on. Try something new. This time it will be different! This time your initial excitement will last long enough to carry you through to the finish line.
Well … I’m sure we all know that’s not the case, looking in disgust at our graveyard of discontinued projects. The pile tends to just rise higher and higher.
So what now? Destined to fail. The whole universe against us? Case closed? If we can’t exit the cycle, aren’t we doomed?
Actually, why not change perspectives and simply turn around?
Try to do the hard parts first
Yes, forget about easy wins. No clients to impress – and even they should prefer you solving the most difficult piece first as it shows actual progress towards their goal. Do the work, then reap the benefits of joy.
On my most recent project I’ve just finished up all the hair-pulling – not that I’ve got any hair left to pull – and anger-inducing parts of database structures, REST API endpoints and core functionalities and now happily dive into some real heartwarming design work with UI/UX and all the jazz. Where I could’ve been stuck by now with a beautiful but static prototype that “could be great” once it’s done, but is just a facade.

It seems to be such an obviously stupid mental hack. “Duh, just turn around, idiot!”. Not a foolproof one though. Shit can and still will go down sideways, and your personal pile of shame might grow bigger still. Yet, you gave yourself an additional chance to stay motivated. Another ember with the potential to light a fire and keep you going when you most need it. So why not try starting in the hard-zone and finish on a high by bringing it to a close doing what you enjoy the most. This time that tiny ember might just be enough to keep your fire burning and allow you to reach the finish.
Time to turn the odds in your favor. More embers, more chances, more wins.