Harry Donald
Productivity Tip:
Draw the Problem
Ever thought of drawing your way through a problem instead of writing it out?
Harry Donald, who shares his “thinking routine” below, sets aside time once or twice a week to work through ideas visually. “There are lots of ideas that are easy to articulate on pen and paper, but there are some that aren’t ready formed in your head,” he says. “Writing them down is not always the best way to get clarity on what those ideas actually are.”
Whether on paper or digitally, he says you can draw the tension around a problem, or sketch out flows or journeys. “Something about working visually allows you to see where the issue / tension really is and sometimes even helps you with the size of it.”
There’s some science behind this. A 2023 review describes drawing as a cognitive tool that can help make visible the otherwise invisible contents of our minds — giving us another way to explore and make sense of an idea.
Try it this week: Pick one problem that’s been circling your brain and spend 10 minutes drawing it. Boxes, arrows, stick figures, scribbles, whatever! Don’t try to make it look good; just try to make the problem visible.
Routine Breakdown
Harry Donald, Founder of Hugo Date
Walk, Draw, Talk: A Founder’s Thinking Routine

Got a lot of thoughts bouncing around? Entrepreneur and founder Harry Donald does, so rather than your usual morning routine, he shared with us his “thinking routine” — a set of steps and tools he uses to stay creative and mentally flexible.
The Routine:
- Start every week with one question: what is the single problem that, if solved, would make all other problems go away? “Obviously no single problem makes everything else disappear. But asking myself the question forces me to isolate the thing that actually ‘moves the needle’ and put everything else to the side for a bit.”
- Go for a walk or a drive twice a day, every day, for 30 minutes. “I have ADHD therefore struggle heavily at desks, sitting in cubicles, etc. However I also need to spend 12 hours a day on my laptop. Walking around or even driving gives me something light to focus on, and this allows me to focus in a way that staring at a screen doesn’t. I do this twice a day, scheduled, and whenever I hit a wall on something. 99% of the best ideas I’ve had have come on these ‘wanders’.”
- Talk to five strangers a day. “I don’t do this for networking or serendipity but purely because you have to acknowledge your own perspective is narrow and always will be. Even if it takes 100 conversations, you will find one that fundamentally changes how you think about a problem and either gives you the solution or triggers a thought that leads you there. These strangers should be either found online or in the street. Throw things at the wall, the success rate will be low but it gets you there. It’s simply good for your soul and expands your brain.”
- Do 1–2 creative exercises per week that aren’t writing. See “Draw the Problem” above!
Why it works:
- Walking, talking to new people, thinking visually… This routine is really about getting your brain out of its usual grooves so you can stay creative, find solutions, and get a change of perspective. All of that is powerful. Research supports some of these habits: walking can boost creative idea generation, while mind-wandering may help with creative problem-solving by giving ideas time to incubate. Interacting with people with different perspectives can also encourage more flexible thinking.
The common thread? Sometimes the best way to think harder is to stop staring at the problem quite so hard.














