Four years

Holdfast at 4 years

Four years ago I started Holdfast Projects at a time of change. A health thing had happened. I left a company I’d given a decade to. We moved up to Scotland to see more of the wider family. I wanted to work in different industries to security (personal finance? digital but less secretive?) and a different kind of work (writing). I knew that I didn’t want to spend half the week down in London, or every day commuting to Edinburgh. So I did some consulting gigs doing product management and design for tech companies, but gradually I tried to nudge the work towards writing what I (semi) jokingly call “expensive words”.

This is both a quadrennial year note for a company and a triennial-ish year note for a new career, and the latter is probably more interesting. Some things I learned, in no particular order:

1. It was hard to walk away from a company I’d co-founded, and I didn’t realise how much I’d need to decompress. But afterwards I wondered why I hadn’t left years earlier. (There were multiple cognitive biases hard at work in both those sentences and the situations they’re describing.)
2. I’ve done 17 projects for 11 customers, though it feels like more. The shortest project was a day, the longest a couple of years. I’ve typed up to 2,000 words a week, and some of them were good. I have read a lot of the internet, and some of it was good. Half of the projects were me working alone, half with a team or with sub-contractors. Fastest-paying customer: under a day after invoice (take a bow, Thayer Prime). Slowest-paying: about 80-90 days.
3. Most of the work has come from people who already knew me or had already seen my work somewhere. When your sales prospects don’t know you or your work, the sales cycle is often tentative and very slow, more like long-term relationship building. So it is interesting to look at where you already have long-term relationships.
4. This suggests that it helps to put good things out there, to be helpful to people (without expecting anything in particular back in the short term), and to stay in touch with people. Being Helpful and Pleasant can be a marketing strategy!
5. Most deals take longer to put together than you expect, so you have to plan for that, which typically means gradually shoving many things forward in parallel. It is hard juggling a sales pipeline to get the right balance between too much and too little. I had to have plenty of conversations because half of the sales leads came to nothing: the conversation fizzled out, or I was too expensive for them, or the timing wasn’t right, or some other reason.
6. You get the work that you do, so if you’re a database engineer who wants to become a plumber, you can’t wait until someone offers plumbing work to you. You have to find a way to do some plumbing, or at least to get closer to that world (foot in the door by doing databasing for plumbers?) My transition from product management to writing was: put some writing out into the world (an example, asserting that “I’m a plumber writer now”, then writing a few reports and web pages etc for people (and continuing to assert it), and then gradually getting writing work that was more interesting and more frequent.
7. A distinctive story. You need to be able to tell the story - the “promise” - as something very brief and distinctive. You want to say to people “I do X” in a way that they get and remember (and then go on to repeat to other people). You want them to understand why you. Funnily enough, since this is part of the writing-for-digital discipline, I’ve found this quite hard. It can help to think about what’s the twitter-length version of what you do and why someone should care. “Newsletters that explain what’s happening on the internet to big companies” hopefully tells the story and hints at the value you’ll create. “Words that work for digital organisations” is still a bit woolly, I’m working on it. But “I type computer words” would have been unhelpful and dull.
8. Writing for organisations is fun. The job to be done is your guide, as is the organisation itself - its values, how it thinks of itself. The Co-op Digital newsletter’s job is to nudge a primarily internal audience to keep thinking about how the internet is arriving on the shores of retail and services businesses. Its tone is slightly sarcastic, slightly poking-the-organisation. ustwo’s newsletter is lighter, more positive and it tells a primarily external audience “look at this cool stuff that is happening!” One newsletter project got taken in house after I and a partner did a zeroth edition, which is fine. Determining success is sometimes hard: we haven’t tracked the readership and open/click rates particularly closely (the Co-op newsletter has a ~50% open rate and 15% click rate and ustwo has ~75% open, 15% click, which seem to be ok). So you might say the writing has had more in common with marketing/comms, evangelism, opinioning, even analysis. The side project - a “how to do money” thing with Anna Goss - has been great but it suffers from lack of time. She has written it up well.
9. Working with other people is good, whether they’re customers, partners delivering a thing with me, or people I’ve brought a project to and sub-contracted. Conversely, working alone is also good. They are different types of good, and maybe you need both.
10. The product management gigs were short term. I found it hard to have much impact unless the client organisation (often my customer’s client) was very receptive. In one case, I was part of a team that made a pretty good thing but the client never used it, which was a shame :( I suspect that product management’s natural commitment should be 2-5 years, not 2-5 weeks or months.
11. As Phil Gyford says in his evergreen guide to freelancing, you have to be your own everything: account manager, sales dept, HR manager, task master etc. Working remote can add complications - continuous partial attention, finding ways to focus on the work, not knowing what’s happening at The Customer - but being fairly present on eg Slack can help (you wonder if working remote favours people who are happy to be ambiently and interruptibly present and can type quickly).

So there’s a bit of momentum now. I can see a couple of decision points on the horizon:

• keep it at its current level vs grow it by working with more people
• focus in on a particular content type vs stay broader

Of course none of it is possible without support from my family, who are the utter best. And thanks to customers, colleagues and co-conspirators - you are many, a delight to work with. You’re all appreciated, I am lucky. Anyway, year 5 let’s go.