An artist tries Shape Up by 37 Signals

Personal projects are hard. There is no one to push you to meet the arbitrary deadlines you set for yourself, and they require a level of commitment that is almost impossible to fathom for the uninitiated.

And, they are necessary. They are necessary for your growth and evolution as a person and as a professional.

Also, a human being is a complicated entity. What drives you one day, probably won't the next. Motivation is great, but it's not enough. And what worked for you on one project, may not work for you on the next. So even if you figure out a formula for how to write a book, or a song, or a movie, when you start your next project, you often have to try a different approach.

And so even though I've done a lot of cool work over the years, it's sometimes still a bit of a mystery to me as to why some projects happen and some don't.

Where things get really tricky for me though, is in finding and maintaining any kind of balance, pace and sustainability. Because when things start working, I feel like I will lose all momentum if I don't race to the finish line from that point on.

My projects also tend to be behemoths that require absolute focus and dedication, and usually, no days off. Most of the time I'm working on these projects by myself, which means that many sacrifices have to be made in pursuit of completion.

As a result, these projects are so intense and exhausting that I can usually only work on one each year, with my natural shipping cycle sitting in the August - October period. I've never been able to achieve a steady and sustainable pace of work, and have instead fallen into a never ending cycle of complete rest/burn out.

Jason Fried explains it well here:

When it comes to project work, and specifically software development, executing something the wrong way can destroy morale, grind teams down, erode trust, crunch gears, and wreck the machinery of long-term progress. So yeah, it’s “done,” but at what cost? By doing, what have we done to ourselves? Do we really have to do that again, over and over month after month, year after year?

Last year I completed an enormous project which I will release later this year. I worked 130 days in a row, and then held a solo exhibition in a gallery in Melbourne in late November.

But I don't want to work like this anymore. I have 3 major goals for 2024, and I need to do things differently this time around so I'm going to try Shape Up cycles and see how I go.

Shape Up is an approach to work developed by 37 Signals. And even though the framework doesn't fit perfectly with my creative projects and the way that I work, the bottom line for me is that my current way of working is not going to cut the mustard this year and I have to do something different.

I am hoping that Shape Up will help me:

Achieve/complete my 3 goals
Find a more sustainable and manageable pace/rhythm of work that I can maintain over the long term
Never work weekends
Work to real deadlines, that aren't too far away and give me a bit of urgency.

The last one is key, because each of the 3 goals each take roughly a year to complete properly, but a 12 month deadline was way too far away to create any kind of useful pressure. I knew that I would just drift through the year if I didn't give myself shorter deadlines.

A couple of things I need to be mindful of:

These are the shortest blocks of time I've ever worked to, (I usually sit in the 3 month/100 day kind of regions), which matters because I have a full time job, and I don't have the same capacity that the 37 Signals team do. I need a bit of slack because life happens sometimes.
I generally don't like to work in such a regimented pattern with many dates to follow. I like one big deadline, but I need to have quite a bit of flexibility in terms of how and when I get the work done. In the past, when I've tried to impose too many dates to follow, I've always missed them.
Shape Up cycles are not supposed to be used during periods of 'new product development', which is essentially what my projects are - brand new things that I am creating from scratch. All of my goals are too big to fit neatly into a 6 week Shape Up cycle so I've split them up as best as I could, mainly focusing on daily output and accepting that at the end of most of the 6 week cycles, my work will be finished, but not ready to ship. All 3 shipping dates will be in the October - December region of the year.

Follow along with your own goals or projects if you like, or check back in at the end of each 6 week cycle to see how I got on.

- Linda ✌🏻