I’ve joined Playground, an “anti-procrastination platform” run by Ida, who I know from Ness Labs. I was curious about her approach that sets up an accountability buddy system but also tries to gamify the whole process. The program is cohort-based and runs over three months. Ida assigns you a buddy in the first session who you’re supposed to meet once every week, and you get a weekly “Playguide” to work through together. My accountability buddy for this cohort is Luise, who is also from Germany, so we can do the exercises in a mixture of English (because that’s the language used in the guides) and German. She’s doing different work and has other goals, but we’re getting along well.

When signing up for the program, you select a goal you want to achieve over the three months. Mine is that I want to shift my work further away from hourly billing and into selling products and services. In other words, the freelancer-to-entrepreneur route. Late last year, I mentioned this in a post where I was thinking about my social media strategy. I co-founded a company that eventually was no longer financially sustainable before starting full-time freelancing, and I’m still working on side projects, both from this time and new. I’ve even found ways to integrate both, but I only have a little to show for it because I need a more precise focus. So I hope to see it during the program, and I will also write about it on my blog.

After a fun getting-to-know-each-other game, one of the main exercises of the first week was to ask “Why?” five times to dig deeper into the reasons behind the goal you set. The challenge for me was that there’s rarely a single reason behind a decision. Multiple reasons require digging deeper into each, so you build up a reasoning tree where you need to ask “Why?” a few times more often.

I want to separate the income from the hours I work. Why do I want this? To have more time and money, both. Here’s where the tree splits into money and time.

The reason for more time is that I plan to spend this time on different things, both professional, like business ideas, and personal, like spending more time with friends or non-monetized hobbies. Why do I want to do these? I like many things, and I dislike saying “No” to anything (remember my musings about focus).

The reason for more money is the freedom that money brings. I can reinvest the money in the business to make even more different projects. At the same time, I’d also like to give away some of that money. As a follower of effective altruism, I am confident that giving money to high-impact causes can make a difference. And I like doing good.

I hope the Playground program can help me work toward this goal, and I will try to document the journey.