If You’re Starting a Side Hustle in 2020, Start Here

If I were starting over, these are the tools I’d turn to.

Shaunta Grimes
Sep 18 · 6 min read
Photo by Headway on Unsplash

When I started Ninja Writers in 2016, I did a bunch of things right and I stumbled my way through some other things. But it all worked out. My little online entrepreneurial enterprise has done well for itself.

Because of the nature of my business, I spend a lot of time teaching other people and thinking about how well what worked for me would work today for others. That’s important to me, because some of the missteps I took happened because I took advice that seemed good at the time, but was actually seriously outdated.

The online world changes far more rapidly than the ‘real’ world does, and often, by the time someone gets around to teaching you something — it’s just too late. That thing is past its prime.

There are some things that I think are important right now: coming up with a good idea for your business, building an email list, connecting with your followers, standing out, knowing when (and whether) to give up, actually getting started, and having a growth mindset.

Most of those things? They’re pretty universal and timeless. They were important in 2016, they were important well before that. And they’ll be important for along time.

Even the methods don’t change too much, if you get down below the gimmicks and the tricks. Find an idea that speaks to you, find other people it speaks to, and find a way to connect with them.

These are the tools that I’m using now and that I’d want if I was just starting out right now. Interestingly, most of them aren’t particularly new.

Ideas to Get You Started

Chris Guillebeau’s Side Hustle School Podcast

For more than two years, Chris Guillebeau has produced a daily podcast where he talks about an entrepreneur and their successful idea. Every. Single. Day. That’s a lot of ideas. It’s a fun, quick listen that might get your creative juices flowing.

He’s gathered 100 of them into a book, too. The goal is to see how other people are starting their businesses without giving up their day jobs — yet. Guillebeau wants you to see that it doesn’t have to be all or nothing.

Connecting With Your Followers

Superfans by Pat Flynn

Pat Flynn’s book, Superfans, is about taking casual followers and turning them into active fans. The kind of fans that love your work and spreads the word about it.

Superfans are the difference between a good idea and a successful one. And Pat Flynn has written a book — not about changing the whole world with your business, but about changing the world for one person at a time.

I found Flynn’s approach refreshing, because it’s not about gimmicks or tricks or strategies. It’s about making connections.

Email List Building

Growth Tools

So, I tried to find a book. When I was starting out, I tried. Recently, I tried. And I’ve never been successful at finding one I liked. It’s finally occurred to me why. The world of publishing moves so slowly and the world of email marketing changes so quickly — the two just don’t mesh.

But there’s a website that I adore.

Bryan Harris taught me how to build an email list with Videofruit in 2016 and he’s still the best that I know of. He’s rebranded as Growth Tools, and as always, he’s hugely generous with his ideas. I never fail to learn from him.

Growth Tools has a simple step-by-step teaching style that I love. It’s got a ton of free simple guides and tools. The ideas are basic almost to the point of being obvious, but when you try them, they work so well that it’s spectacular.

I really can’t recommend Growth Tools highly enough.

Standing Out in The Crowd

Purple Cow by Seth Godin

This book is a golden oldie, written in 2007 — which, when we’re talking about online business, might as well be the middle ages. But sometimes the best advice is timeless, I guess, because I’ve still never read a better book about how to make an impact.

In fact, I think the concept of the purple cow (being remarkable) is even more important now than it was in 2007. The market is far more crowded. This is a little book and it’s not going to give you any deep instruction, but if you’re just starting out, it might save you from wasting time rehashing the same old thing that hundreds of other entrepreneurs are already doing.

Knowing When to Quit and When to Stick

The Dip by Seth Godin

Okay. So Seth Godin was on a roll in 2007. It says something that his work from a dozen years ago is still super relevant today, especially when we’re talking about an industry that changes with alarming speed.

The Dip is one of my favorite books of all time. It’s tiny and very too the point. It talks about how to know when to quit on an idea and when to stick it out. Important stuff. Godin has a series of videos on his Instagram account about The Dip that are fantastic. (Scroll down until you see the posts that look like the cover of the book.)

The thing about The Dip is that it will help you figure out if you’re giving up because it’s hard or quitting because you’ve started something that won’t work. Those are two very different things.

Getting from Zero to One

Atomic Habits by James Clear

Sometimes, when we want to start something big and hard and a little scary, like a business, we can get so caught up in planning that it actually feels like we’ve started when really? We haven’t.

Getting from zero to one — taking the hard first step and actually starting — is tough. Habits help. The best book I know about habits and how they work and how to utilize them is Atomic Habits by James Clear. He’s got a great blog, too.

Getting Your Mind Right

Carol S. Dweck’s and Angela Lee Duckworth’s TED Talks

First, I hate the word ‘mindset.’ It gives me the heebie jeebie’s for some reason. But there’s one mindset concept that’s not only important if you want to start a business — it’s essential. You have to believe that you can grow into it. Dweck calls it a growth mindset.

Her Ted Talk on the subject is wonderful. Being able to understand that you haven’t succeeded ‘yet,’ rather than believing you’ve failed at the first sign that you’re struggling is huge. She’s talking about children here, to educators, but it’s still a very important message.

One more — Angela Lee Duckworth’s TED Talk about The Power of Grit is a message about a similar mindset.


Here’s my secret weapon for sticking with whatever your thing is.

Shaunta Grimes is a writer and teacher. She is an out-of-place Nevadan living in Northwestern PA with her husband, three superstar kids, two dementia patients, a good friend, Alfred the cat, and a yellow rescue dog named Maybelline Scout. She’s on Twitter @shauntagrimes and and Instagram. She’s the author of Viral Nation and Rebel Nation and the upcoming novel The Astonishing Maybe. She is the original Ninja Writer.

The Post-Grad Survival Guide

We're confused twenty-somethings. We dish on our post-grad blues, successes, failures, and everyday life right here. Featuring topics related to work, relationships, travel, finances, and so much more.

Shaunta Grimes

Written by

Learn. Write. Repeat. Visit me at ninjawriters.org. Reach me at shauntagrimes@gmail.com. (My posts may contain affiliate links!)

The Post-Grad Survival Guide

We're confused twenty-somethings. We dish on our post-grad blues, successes, failures, and everyday life right here. Featuring topics related to work, relationships, travel, finances, and so much more.

Welcome to a place where words matter. On Medium, smart voices and original ideas take center stage - with no ads in sight. Watch
Follow all the topics you care about, and we’ll deliver the best stories for you to your homepage and inbox. Explore
Get unlimited access to the best stories on Medium — and support writers while you’re at it. Just $5/month. Upgrade