I grew up in a blue collar family. My dad was a cop, his dad was a cop. I sort of figured that’s what I would do, too. Tradition, you know?
But I was a pretty good artist. That was my talent. As a kid I would draw incessantly. I dreamt of becoming an animator for The Simpsons 1. If that didn’t work out, I’d be a cop.
Nobody I knew talked about entrepreneurship or investing or travel. Everyone had the same mental model: get a safe job, never leave it, thank your lucky stars, retire, die.
I strived to be the best version of what my parents told me was possible which, in hindsight, wasn’t much. Greatness was for other people.
Luckily, the internet happened and I was able to reach far beyond what my little neighborhood had to offer. Still, I made a lot of mistakes along the way–mistakes I still see marketers, engineers, and designers making today.
A few months ago, I gave a talk titled 8 Things I Wish I Knew to a group of students at Drew University. My goal was to short circuit many of the key lessons I learned over the past 15 years.
Here’s what I told them.
1. Code is a secret weapon for non-engineers
Even if you’re not a “pure” software engineer, learning enough programming skills to be dangerous can do wonders for your career.
- A marketer that can glue together APIs and understands SQL…call me?
- A banker that can automate away boring Excel projects can double her productivity.
Every time you hear the excuse “we’re waiting for the dev team’s help”, that’s opportunity knocking. Don’t wait for the dev team to help with your project. Be your own dev team.
Once you learn to code, automatable tasks start popping up everywhere. Automate them without asking and then show your colleagues or manager.
Proactively reaching above and beyond my job description, with code as my ally, scored me several promotions.
(Caveat: this won’t work if you do a half-assed job. Make sure your scripts / apps / macros actually work before you show them off. Otherwise you’ll become the guy or gal who tinkers around and breaks stuff.)
2. Ask for more money
Don’t sell yourself short when applying for a job. Aim 25% higher than you think you can get and see what happens. An extra $5k up front will yield you +$100K gross over 10 years.
I used to think that I would personally offend someone by asking for too much money. Then I’d be put on some secret blacklist with all the other pains-in-the-assess, never to be hired by anyone again. How ridiculous.
You won’t offend anyone. Hiring managers do this all the time. I’ve been on both sides of the table many times–in 99.99% of cases, the person doing the hiring isn’t going to take it personally. They aren’t emotionally invested. It ain’t their money! Their kids won’t go hungry if you negotiate a higher salary.
Also, unless they’re an idiot, they’re not going to think, “HAH! He thinks he deserves $X! How presumptuous! Although he’s a perfect fit for the role, I’m not even going to dignify that with a counter!”
This is business. They will counter. The most probable outcome is that you’ll still end up with more money than you thought you could get. If the counter sucks, on to the next.
Dive deeper into salary negotiation with this epic 7,000 word blog post from Patrick McKenzie.
3. What’s obvious to you is amazing to them
It’s easy to forget what it was like to be a beginner and take your own knowledge, thoughts, and creations for granted. You marvel at other people’s work and give them credit for being innovative and clever, not realizing that others may feel the same about you.
Derek Sivers explains this best:
One day someone emailed me and said, “I never would have thought of that. How did you even come up with that? It’s genius!”
Of course I disagreed, and explained why it was nothing special.
But afterwards, I realized something surprisingly profound:
Everybody’s ideas seem obvious to them.
So, ship your damn thing. There’s a new class of freshmen entering your world every day, eager to learn what you learned yesterday, today.
4. Show your work
The only people who care about your GPA are people who you’ve given no other basis to evaluate you. — Chris Sacca
I didn’t even ask for the résumé of the last 2 people I hired. I did, however, see their blog posts, their design work, their code. I looked at the way they interacted with people on forums, Twitter, Stack Overflow.
Showing your work is one of the best ways to prove that you’re Smart and Gets Things Done.
Making your work public also has this strange side effect: people find your site in Google, they sign up for your mailing list, they buy your stuff, they want to work with you.
Nathan Barry’s mantra is Teach Everything You Know. It’s worked out rather well for him.
5. Don’t ask for permission
How many times have you heard “I’ll do it when”?
I’ll do it when…
- I’m able to raise money
- I get older
- I get my degree
- A publisher comes knocking
- I land an audition
The internet has largely eliminated gatekeepers. No more excuses for why you can’t start now.
If you want to be an FBI agent or a heart surgeon then yes, you still need to follow a very specific path. But those careers tend to top out anyway. Once you make partner at your law firm, then what? How do you 100X your billable hours without breaking the space-time continuum?
The cost of entry is hilariously low in online business, software, and the creative arts. You don’t need permission or much money to share your film on YouTube, self-publish your ebook, open your Etsy shop, release your podcast on iTunes.
The market is the judge and jury. And the market doesn’t care if you’re 7 years old, or if you went to Princeton, or if you grew up in a bad neighborhood. If you make something people want, you can win.
If we’re being honest with ourselves, the biggest barrier to starting is our fear of failure. Our fear of critics.
In my experience, success is negatively correlated to f*cks given. Everyone has critics, says Amy Hoy:
Has there ever been anyone in the entire history of humanity who was universally loved? Of course there will be people who don’t like your work.
Unless of course…Do you think you can do better than Jesus? Jesus had haters.
6. Sell your by-products
This is a lesson I learned from the guys at Basecamp, Jason Fried and DHH. Jason has a brilliant post about it, which I make myself re-read every year.
Everything has a by-product. Observant and creative entrepreneurs spot these by-products and see opportunities.
I had this tactic in mind when I was building Munchkin Report, which is a Ruby on Rails app. Before I could build Munchkin Report, I had to learn Ruby. What was the by-product of learning Ruby? My notes.
As I was learning, I turned my detailed notes into a book called Learn Ruby the Hard Way, modeled after Zed Shaw’s Learn Python the Hard Way.
I could have learned Ruby and kept my notes to myself. Instead, I turned that by-product into something that made money and created tremendous value for thousands programming students around the world.
(This essay you’re reading right now is a by-product of the talk I gave at Drew.)
7. Play on easy mode
I wrote an essay about this, but the biggest takeaway is to resist the urge to make something completely new.
Instead, innovate on an existing idea. It’s one of the best ways to increase your likelihood of making something people want.
Build yet another bug tracker. Build forum software. Build a help desk tool. Find a space where the existing products are ordinary and make something remarkable.
The remaining 4 elements of easy mode are:
- B2B not B2C
- Recurring revenue
- SaaS not self-hosted
- Established tech stack
Ultra-easy mode would be a digital product like an ebook or course aimed at an audience that pays for things and can be easily reached online.
8. Perfect is the enemy of good
When you face writer’s block, just lower your standards and keep going. –Sandra Tsing Loh
When the kids in my middle school learned that I could draw, they’d gather around me during lunch and make me sketch their favorite comic book characters.
I’d toil away for 40 minutes, letting my chicken nuggets go cold. Then the bell would ring, and while my friends were busy holding an auction to see who got to keep Wolverine, I’d glimpse a tiny imperfection, rip up the paper, and toss it in the trash.
I couldn’t let my artwork escape into the wild if it wasn’t absolutely perfect. This is a fatal flaw that I still struggle with. I’m embarrassed to tell you how many times I’ve edited this essay.
More often than not, done is better than perfect. My “customers” would’ve gotten value from the pencil drawings I threw away. Flaws and all, my work was worth something to them. And that’s the only thing that matters.
There’s a great story from the book “Art and Fear” that illustrates why you should ship your imperfect work and learn from your mistakes:
The ceramics teacher announced on opening day that he was dividing the class into two groups.
All those on the left side of the studio, he said, would be graded solely on the quantity of work they produced, all those on the right solely on its quality.
His procedure was simple: on the final day of class he would bring in his bathroom scales and weigh the work of the “quantity” group: 50 pounds of pots rated an “A”, 40 pounds a “B”, and so on.
Those being graded on “quality”, however, needed to produce only one pot — albeit a perfect one — to get an “A”.
Well, came grading time and a curious fact emerged: the works of highest quality were all produced by the group being graded for quantity.
It seems that while the “quantity” group was busily churning out piles of work-and learning from their mistakes — the “quality” group had sat theorizing about perfection, and in the end had little more to show for their efforts than grandiose theories and a pile of dead clay.
If you’re convinced that shipping early and often is a good idea, but you need a detailed plan of attack, I highly recommend reading the book Just F*cking Ship.
9. Everyone gets overwhelmed
(I know, I know, I said 8 things. Consider this bonus material.)
Things will get hard. It’s important to find your pressure release values. Whether it’s yoga or reading fiction or watching Netflix or playing with your kids. Find something apart from work that gives you joy.
When I get overwhelmed or frustrated, I read Merlin Man’s essay, Cranking. It really puts things in perspective for me.
It’s quite sad, but it’s beautifully written and the moral of the story–never let your hard work fuck up the things you love–really hits home for me. I hope it speaks to you, too.
Another thing that always puts me in a great frame of mind is this goofy 5-minute video called Where The Hell is Matt?. This dude, Matt, travels around the world dancing with strangers from all different cultures.
I started watching Matt’s video every morning before I start my workday and it reminds me that there’s a vast and incredible world with remarkable people facing challenges and opportunities of all shapes and sizes. It has a funny way of making Bug #4124 (Not Reproducible) seem rather insignificant.
Good luck. 🍀
1. I can still draw Homer Simpson in less than 20 seconds.