Anna Barnev, examples for the book cover, design by Leah McCloskey

(written by lawrence krubner, however indented passages are often quotes). You can contact lawrence at:, or follow me on Twitter.

My new book is out! Check out “How The Young Anna Barnev Established Her Career As A Graphic Designer“.

In chronological order, starting in January of 2019, these were the designs that Leah McCloskey came up, to try to capture the spirit of the Anna Barnev story.

Here was the first batch, which she sent to me on January 14th, 2019:

Of these, I liked the hand drawn version of Anna, because she looks confident, and I thought it was important to have a cover where she looked confident. So I asked Leah to follow up on that idea.

On January 25th, 2019, she came back with this batch of ideas:

I thought these did a good job of capturing the humor in the Anna Barnev story, but they didn’t capture the confidence that Anna eventually attains. I wrote to Leah and suggested that if we only have one image of Anna, then it should be an image that shows what she eventually attains. So it should be an aspirational image, full of confidence.

On February 24th, 2019, Leah sent me this batch:

All of these seem like they could be great covers for a novel, though not necessarily Anna Barnev. These were close enough that they were all worth considering. The woman in the green sweater seems sophisticated, but is the image too humorous? The woman in the last image seems like the hero of some romantic novel, but is that novel Anna Barnev?

I was willing to move forward with any of these, but I also thought, before we made a final decision, we should experiment with multiple images, and perhaps a cartoon approach. When I first met Leah, she was head of design at a small startup call Haystack, so I now wrote to her and referenced the work she’d done there:

On February 27th, 2019, I wrote to Leah:

I love the humor of the drawings you did for Haystack. They were clearly funny. Also boldly funny, in the sense that Haystack needed confidence to go with that as their look. When Haystack was in crisis, they also removed all of your artwork from the website. They no longer had the confidence to go with something that was so boldly funny, on what was supposed to be a serious business oriented website. But I think whatever we do with the cover for Anna, it should say that you and I have confidence.

That same day she wrote back:

Hmm OK. I guess what I maybe need is some direction on what we think the humor in her situation is. Like before I was thinking of her as a little sloppy and so it was like ok she’s got this big confidence but is like a little messy and rough around the edges and this unlikely heroine and that’s the silly thing? But if she is confident and cool I am not sure what is the silly part. Like maybe she’s SO cool and successful that the joke can be the depth of her success like just her in the nicest apartment with the coolest things… but the story doesn’t really spend that much time on her trappings of success. So maybe think about what the funny part is, if it is her on a white background — also, graphic design isn’t a super funny career, like if it was a carpenter or something she could have like SO MANY TOOLS but there is no visual thing that screams “wow what a typical graphic designer,” something to mull over. Maybe we could have an image with her conspiracy-theorist-style mapping out a path for herself with red paint on a wall? Though in the book her course isn’t really all that premeditated.

I know you already vetoed this idea, but I keep coming back to it – I think because the title so clearly announces the destination of Anna’s journey, and is already a pretty funny title since it’s long and has a full name and gives away the end of the book – the joke can be that the image shows her doing a bunch of different things, none of which is 100% being a graphic designer – just this idea of all the little parts of a life that happen in service of a goal without ever seeming they’re in service of it, which I feel like is territory the book covers. I think it also connects well to the emoji themes in the book, having this sort of generic “young woman” figure moving through a bunch of little vignettes. I did a super fast sketch of what I mean.

In my mind (apologies in advance if I’m totally off) the book is about the nature of a person’s story and path in life – how a person’s career and trajectory is shaped by all these little encounters and strokes of luck big and small and bouncing off of these events and trying to learn from them and grab what you can and use it, with Anna as the character who has an innate sense of when she can use something and her best friend as someone who doesn’t. I think the story is a lot about a journey and not too much about arriving, so I like the idea of a drawing that kind of deals with Anna’s path more than fixing her in a point in time. Just some thoughts, let me know if anything resonates!

Although she wrote “I know you already vetoed this idea” I didn’t recall her mentioning this idea before, and I liked it, and I loved the sketches of the idea that she had come up with:

So I said I loved it.

On March 10th, 2019, she came back this batch:

This struck me as very much what we wanted to do. I liked that it both worked for the Anna Barnev story, and it felt to me like a classic Leah McCloskey cover, based on all I knew of her work. So I asked her to refine this.

On April 9th, 2019, she came back with:

I gave some feedback regarding the font, the amount of space that the icons should hold, and how much prominence the title needed.

On April 22nd, 2019, she came back with:

I loved the cornflower blue color, but the icons tend to get lost against that color, so I suggested the first of these was nearly perfect and suggested she move forward with that.

In early May she showed me a few more variations:

If the font was loud, then I thought it would detract from the cleverness of the artwork, so I suggested we follow up on those designs where the font was relatively muted. Variation #1 worked as the starting point for the final book cover, which Leah sent 3 weeks later:

As always, I have found it very gratifying to work on this project with Leah McCloskey.

My new book is out! Check out “How The Young Anna Barnev Established Her Career As A Graphic Designer“.

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