Advice to a younger me

Go Cubs Go

Someone recently asked me advice I’d give my younger self. Well, here are three things of an endless list 🙂

Don’t be embarrassed

I think I’ve done a relatively good job putting myself out there in the world, but I can still point to many moments where I should have done one thing, yet did another. I didn’t release that app. I didn’t start that blog. I didn’t go to that audition. Because I was too embarrassed.

That fear of embarrassment is the key thing holding most of us back from the stuff we really want to achieve. The best of us are out there trying as hard as they can without fear of embarrassment, and yet they screw up constantly. They just deal with it. And quickly move on.

I bet there’s something you’re considering doing right this very second but keep putting off just because you fear what others are going to think. I know I am.

Become a better storyteller

I’m obsessed with becoming a better storyteller. Not just in words and articles, but now especially with video. How can I better inspire/captivate/motivate people through my content and ideas?

One of the key lessons there is to think about how an article or video or whatever leads people from one end of the spectrum in a strong human theme to another (hate/love, fear/security, despair/happiness, failure/success, embarrassment/pride, ignorance/genius etc.) Show people how the hero struggled to find love from a hateful place, or overcame great odds to go from failure to success, etc.

And it doesn’t always have to go from “negative” to “positive”. People crave authenticity. It’s ok to show people an autobiographical story of you moving from something good to something bad. Of course, they’ll probably love to tune in again to see how you can reverse that course.

A book I’m hooked on right now is Story. It’s about screenwriting, but really it’s universal. You want to write a blog post that keeps people’s attention, figure out how screenwriters and movies get people to stay in their seats.

Learn what really makes “good design”

Sounds like you’re focused on being a great developer. That’s awesome. But I wish my younger self also spent more time early on figuring out how to be at least a moderately ok designer. Too many people think they can’t design, just because they suck at things like picking aesthetically pleasing colors. They feel like, “I can’t make things that look good. Shit, I can’t even pick nice furniture for my home. I can’t design.”

Yes, there are some ridiculously good designers and their talents should be employed and not taken for granted.

But as a solo developer you don’t want yourself stuck in a spot where you can’t get a project out the door because you can’t find someone else to craft something that you think is “good design”. Figure out some basic principles of what makes great design.

Here’s one: writing.

It’s similar to watching video. Sure viewers want great visuals, but if the sound is terrible you’ll walk out. The opposite isn’t true. People watch poorly taken video all the time as long as the sound is good.

Same goes for writing. The “aesthetic” design can lag, but the copy can’t. It needs to be engaging, helpful, clear.

And there’s some great resources that can help you see a few basic principles to making good design. One of my favs is Bootstrapping Design.


I could go on and on.

P.S. If you enjoyed this article, you should follow my YouTube channel, where I share more about how history, psychology, and science can help us create better businesses. And if you find yourself overwhelmed while organizing your own small business or customer feedback, check out how Highrise can help!


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