Six months of habits

So, I started a company to do freelance copywriting and strategy development six months ago. It’s been good. But long enough has passed that I’m starting to think critically about my habits so I can make the next six months better.

I’m going to write them here to help me learn.


FreeAgent has been essential. It’s nearly good enough I could use it without an accountant, but I don’t quite have the confidence to do that just yet. Maybe in a couple of years.

I’ve been lucky with clients so far that Google Drive has been a suitable way of getting copy and documents to people. That won’t last forever, but it’s worked this far. I’m still bouncing between Google Slides and Keynote week-to-week. Slides just isn’t reliable enough to do what I need it to. It’s very close though.

I’ve been doing Ben’s One Notebook per project for the first time and that’s been extremely useful for separating chunks of thinking and drafting. I’m also running an occasional notebook because it’s too valuable not to. I still do my best thinking by writing stuff down; it’s the fastest way to find out whether I’m wrong.

Trello, Slack, Clear all useful. Daily utilities, but… not irreplaceable. Slack in particular has introduced different problems (more on that below).

Scheduling and estimates

This is interesting. I think my estimates are pretty good. A lot of that comes down to the practise I got into at GDS, and creating the rhythms I need to get stuff done in time.

But that means I’m not building in a buffer. I haven’t yet worked out if it’s better to estimate high and bill low (‘I thought it would take four days, but actually it took three and a half’). Right now I’m keeping them in line, but I should probably keep that in mind for a few future gigs.

What I’m not taking into account though is Slack. I’m not in the habit of fine tuning my availability there, which means I’ll check in on conversations and feedback outside of agreed hours.

A few options: be firmer about the hours, agree a ‘Slack tax’ with a client, or just accept that’s how this stuff goes for freelancers. After all, this is just Slack doing to me what email/mobile phones/afternoon post did for people in the recent past. I think I need to work out ‘What’s right for this job?’ a bit more clearly than I do now.


I was going to write something about goals, but that’s not quite right. Not when it comes to work. I have things I want to do, but very few of them are directly tied to my professional life. That’s been a common theme for years. Often those things have led to work, through routes weird and delightful, but that’s not often the point of doing them.

So something I’d like to do in the next six months is work out what motivates me to keep working outside of paying rent.

I know people who’d stop working in a heartbeat, if the opportunity came up, but I don’t think I’m there. I like making things. I’d like to get to a place in life where rent is cheaper, for whatever reason, and I want to feel like I’ll have the thrust to do the next thing even when I don’t have to.

Meanwhile, I’m trying to cut down on things that don’t motivate me. Restarting Small Observation was an attempt to kickstart a new daily rhythm. It didn’t manage that, and in some ways worked against new routines. So I’m stopping. Similarly, dropping in and out of sessions of Battlefront elevated my tension in downtime instead of letting me zone out, which is counterproductive. Cooking, jogging, painting… those are great and my mind wanders. I need to make time for more of that.

Get away

I’ve been away a lot in the last six months, but almost every trip has been tied to a job, a mission, or Marioke. I’m going to take a last-minute break in August to shake that up. Actual holidays, Matt: take them.