I spent $20 creating an avatar of myself.

Issue #43

Hey there, I’m Lesley. Welcome to the latest issue of Failing Forward — A weekly newsletter sharing my experience as a bootstrapped co-founder.

There’s no bravado here. I fear failure, just like you. I write this newsletter to remind us both that failure is not just okay, it’s often the best way forward.

I spent $20 creating an avatar of myself.

I’m sure you’re thinking, “what on earth for?!”

This was a cheap and fun project, and I hope to get lots of mileage out of it.

I’ve been signing up for an increasing number of things on the Internet, and rather than having my real face plastered everywhere, I thought I’d replace myself with a digital avatar instead.

Here’s what I ended up with:

It me!

And here’s how I did it…

I used Fiverr.

Before we go further, let me rid you of this misconception: Fiverr is just a name and a starting point. Most things on Fiverr cost more than 5 bucks. And good thing they do, after all, you get what you pay for.

After looking through some options, I settled on an illustrator, which cost me SGD14 (~USD10).

Sorry to interrupt, but if you’re enjoying this post, you might want to subscribe and receive new issues via email. Your future self will thank you!

[memberhero_form id=244]

When hiring freelancers online, you need to give good feedback, but also be realistic.

Simply put, you can’t pay $14 and expect a Picasso. It’s just not realistic. Having said that, being clear on what you want can get you further than you think.

In my case, I sent her a photo of me and she came back with this:


It wasn’t awful, but it needed work.

Specifically, I asked if she could:

  1. Move the eyes down a little
  2. Make me smile more
  3. Make my eyebrows less harsh
  4. Move the dots on my right cheek inwards, nearer my nose.
  5. Give my skin colour

She came back with this:

Okay, now we’re getting somewhere! This looked decent!

I still wanted to make a few changes, but didn’t know exactly what changes to make.

So instead, I decided to accept the work, pay the illustrator, and continue to mess around myself until I was happy (or accidentally turned it into an unsalvageable mess. Either way, at least it’d be my own doing).

Remember, we have to be realistic. And also fair to the person we’ve hired.

So I paid an additional SGD7 (USD5) for the working files, which gave me the ability to make my own changes, and considered the job complete on her end.

Now it was my turn…

With the working files in hand, I spent an hour messing about.

To be clear, I’m not a pro. I also couldn’t have done this without the illustrator giving me all the elements I need. She got me 80% of the way, and I did the remaining 20% of moving stuff about. She has the skills, I simply have the advantage of knowing what my face actually looks like.

In any case, I was careful not to overdo it. I knew how easy it would be for a portrait to suddenly look weird because an element was a pixel or two out of whack.

Knowing this made me really careful not to mess up the original. So I dutifully made a new artboard for every change I made.

Conveniently, this allowed me to turn my process into a GIF, letting me show you the changes I made in stages. Cool, huh?

After asking for feedback from some friends and making some final changes, I was done! What do you think of the result?

Would I do this again?


It was nerve-wracking seeing myself in illustrated form. Especially the initial version. But with some additional messing about, I now have an avatar I can use everywhere!

Is it the best illustration of me in the world? Obviously not. But for $20, I think I got a decent job!

Look out for it in the wild!

I’m building Newsletter Glue — an email newsletter platform on WordPress with a Gutenberg-first approach.

Here’s what I got up to this week…

🔥 Highlights from this week
  • Created a new logo! I wanted the logo to look more friendly and hand-crafted. And, dare I say it, glue-like.
💔 Lowlights from this week
  • Don’t think anything went wrong.
✅ Completed this week
  • Made some big strides with the newsletterglue.com website
  • Started work on new blocks (meta data and forms)
🎯 Goals for next week
  • Finish up the new blocks and the final touches on the author and callout card blocks.
  • Finish up newsletterglue.com.

Worth a thousand words


Worth your while: Here are my favourite links from this week

Listen: Can A Child Be Raised Free Of Gender Stereotypes? This Family Tried

When Isis was swaddled in pink as a baby, passersby would comment she looked precious. In contrast, when wrapped in yellow or green, people would say Isis looked strong.

This observation cemented Royce and Jessica James’ resolve to raise their child without gender norms. They realised the subconscious impact gender stereotypes had on children and the way people interacted with them. And they wanted no part of it.

Personally, I’m all for it. My parents never forced me or my sisters into dresses or to do girly things as children. While my sisters turned out more girly than me, I’m glad we all got to choose. Listening to this podcast, I’m surprised by the intensely negative reactions this couple got. Listen to podcast (transcript available) →

Read: One of nature’s many attempts to evolve a crab

Convergent evolution is where independent evolution creates the same features in different species. Here are two examples that I find really interesting:

The first is carcinisation, or convergent evolution for crabs. Nature has evolved crabs at least 5 times!

The second is sloths (unfortunately no cool name for this). Two-toed and three-toed sloths are not related at all. They evolved convergently. That’s why they look completely different, despite both possessing similar s l o w movements.

Read about crabs, then sloths

Watch: Desert parkour

This is as cool as it sounds. A bunch of ninja-like parkour runners jumping, running and hurtling across sand dunes. Watch video →

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