Writing with Uncertainty and Why Sisyphus Rocks [Ice Cream Sundae]

Willem van der Horst
Ice Cream Sundae
Published in
8 min readMay 27, 2016
Image Credit: Ann Wuyts

This newsletter was originally published via email on the 8th May 2016. You can sign up here to get it in your inbox first. Ice Cream for Everyone is a marketing & brand strategy consultancy.

Sometimes I struggle writing these essay length Sundae pieces every week. Generally once I figure out my topic it’s been getting easier the more I write. Not so much this week. I’ve been writing several drafts and everything feels kind of sluggish.

I’ve started measuring the time I take to write them. On average it takes me about four to six hours a week. I’ve been averaging four in the past few weeks; this week might be more like six or even seven.

I have no idea if the time is good or bad, I’m still not too sure who or what I should be comparing this exercise to. I think the closest similar inspiration I know could be Maria Popova’s Brainpickings email in terms of length though the content is different, possibly even more demanding of your attention as a reader than this is. Ice Cream Sundae is meant to be a fairly fun, light and easy read.

I’ve been alternating between feeling sorry for myself and picking myself back up lately; getting back on track rolling that rock up the hill like Sisyphus once more. Sometimes I hesitate how personal or negative it’s worth being in writing this newsletter. I don’t want to dwell on anything negative too much, though I think it can be worthwhile to say I don’t always feel like a million dollars. Nobody does and I believe there’s some value in taking a moment acknowledging our own humanity whatever it looks like. The mistake might be to wallow in the feeling and overdo it; I’ll do my best to avoid that.

We always want to show our best sides publicly, though of course being human and life in general carries a whole range of emotions and situations, not all positive.

Social media has done funny stuff for this, we display personas increasingly detached from our real lives and there are sometimes consequences for people on the receiving end. The term “social media depression” was coined to describe states of envy, resentment or loneliness people can feel when passively browsing the multitude of amazing photos friends or acquaintances post.

Just so we’re clear nothing that bad happened, just a few things that make everything else feel kind of tiring. I’m looking for work and it’s not happening as easily or quickly as I would have liked. More specifically after a couple of interviews for this one interesting job, I was told I’m not quite strategic enough for the role. That was upsetting given how being a strategist is my main job title. I guess Sisyphus must have had those days when he thought: “Screw this rock today; I’ll just lay down here at the bottom of the hill for a little while.”

I’ve been freelancing for over a year now and while the independence, freedom and variety of projects is incredible, sometimes the uncertainty is tough.

I’m sure it’ll all turn out fine, partly because it has before and also because I’m confident in my abilities and experience. I know I’m good at what I do (Extremely talented and experienced professionals have told me so and I believe them) though sometimes I look around and wonder if I should do more of the same as other peers; like spend more time commenting and providing opinions about the marketing and advertising industry rather than writing about banana jokes, Japanimation or roller coasters.

Uncertainty creeps in and can easily take over.

I’ve regularly been thinking about what I’m trying to achieve with this email newsletter and realise I haven’t written about it here, now seems like a good time.

Last year a few friends and acquaintances told me that I should start an email newsletter. They said from either experience or hearsay that it was the most effective form of marketing to attract new clients and stay on their radar. I’d only recently started freelancing. Attracting clients, staying on people’s radar and hopefully raising my profile in the industry seemed like an essential endeavour and it still does.

The exercise for this kind of email marketing is slightly different than for online retailers such as Amazon or Zappos, in addition to be kept in mind be having a presence in your inbox, their intention is also to encourage you to visit their website and ideally purchase products. While it’s great if you check out my website, I on the other hand don’t sell anything directly so I don’t necessarily need you to click on the links I provide.

If you’re reading this I’m assuming you know you can contact me if you’re looking for marketing and brand strategy advice. (Though please tell me if I’m mistaken).

I was already signed up to a few different email newsletters. One of the most popular formats for marketers or prominent bloggers and podcasters like Tim Ferriss or James Altucher seems to be a curated collection of the best or most interesting links of the week. Good examples include friends like Neil Perkin’s Weekly Fish Food, the Storythings newsletter, James Whatley’s Five Things on Friday and strategy nomadic couple Faris & Rosie Yakob’s Strands of Genius. I think the latter two typically have less links and a little more personal context but it depends from week to week. I enjoy them all though admit I rarely have time to look at all the links they send. I recommend checking them out though; they’re certainly worth it.

I have about 25–30 tabs open in my browser at any given time and half of those are articles or videos I mean to read or watch. I also have the One Tab plugin with who knows how many more links I mean to check out. I’ve got way more links to interesting stuff than I have time to consume them in.

I recently interviewed Cindy Gallop for my podcast and she talks about this idea of “collaborative competition” to designate businesses reproducing competitors’ work, doing the same thing everyone else is in the same industry. This leads to homogeneity and makes businesses vulnerable to innovative or disruptive newcomers. Think of the iPod showing up in a world of almost identical portable CD players and you’ll get the idea.

I wanted to do something different.

Another recurring piece of advice I read is that if you’re going to commit to doing something on a weekly basis, you had better enjoy it because it will take time.

I enjoy telling stories, may it be about my own life, or made up ones. I have a science-fiction novel vaguely on the go that I admit I haven’t been writing anything for in close to a year or so, aside perhaps a few paragraphs here and there. I wrote an ugly and illegible first draft for NaNoWriMo in 2014 and that’s about it. That said I still want to improve my writing and the most consistent advice from writers is to practice. I thought of the newsletter as an opportunity to do so.

I didn’t feel like writing more about where brands are going or what advertising trends mean because I read a lot of this stuff from other talented strategists and marketing commentators already. I also research and write about branding and marketing for a living. Don’t get me wrong, I really enjoy my job and will happily help you with brand and marketing advice if you need it. It’s just that I consider writing for this newsletter to be more like leisure time — or at least a hybrid of work and leisure. As a freelancer there is little difference.

The four to six hours it takes to write usually represent five to seven more episodes of TV series I used to watch per week, rather than hours working on projects, looking for new work, meeting potential clients or taking care of admin and chasing invoice payments. Now I might only watch one or two episodes of TV series and have drastically reduced the number of shows I’m following.

I enjoy writing and telling stories so that’s the direction I took for the Ice Cream Sundae newsletter. I wasn’t sure what the length would be; I naturally tended towards this 1,500–2,000 words long essay kind of format.

I get great feedback from readers who enjoy it and my email open rate is three times higher than the marketing industry average, so I’m probably doing something right.

If I read something as a story, whether inspired from real events or fictional I’m more likely to remember and the memory is more likely to stick. I think these Sundae newsletters are slowly shaping up and improving. In the past few I feel like I’m getting better at weaving in interesting brand and marketing information relevant to the story I’m writing. I think it’s enriching the whole newsletter with my professional point of view little by little. By the way, if you have questions, comments or feedback it’s always a pleasure to hear from you, don’t hesitate sending a reply.

I’ve been reminding myself of my New Year motto, a sort of guideline to live my life by in 2016: “It’s not over till the fat lady sings.” As I wrote then, I find it really encouraging.

I watched Neil Gaiman’s inspiring speech to the University of the Arts class of 2012 again, about living a life as a freelancer and making good art. His advice is priceless and useful regardless of the kind of work you do. It helped me shape and complete this Sundae. If you haven’t seen it I highly recommend watching it right now. It’s only 20 minutes long.

I also listened to a bunch of motivating guilty pleasure type songs and started researching the effect of music on mood; though that’s a whole topic I’ll keep for another Sundae. One more draft in my slowly growing library of future editions.

Finally today is the celebration of the World War II’s Victory in Europe Day, on May 8th 1945. Nazi Germany signed the unconditional surrender of its armed forces to the Allied Forces.

It’s kind of fitting I published an interview with brand strategist Heidi Hackemer on my podcast this week. Heidi’s consultancy is called Wolf & Wilhelmine, after her grandmother who survived incredible hardships during World War II to give birth to Heidi’s father and look after her family. Her stories are amazing, and it was a fun conversation. I said “Wow” a lot.

I’m ready to get back up and start rolling that rock up the hill again. I think we all have some kind of rock to keep rolling up a hill, there’s just some kind of trick in beginning to enjoy the climb more than focus on reaching the destination. I guess sometimes I forget that part, and then I remember again.

Thanks for reading, don’t forget to forward it to a friend if you’ve enjoyed it!

Cheers
Willem

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Willem van der Horst
Ice Cream Sundae

French/American playful brand strategist, tabletop gamer, skier, and traveler. Check out the Ice Cream for Everyone Podcast & Sundae newsletter on my website!