This should probably be episode 1, not 267, but if I’m being totally honest, I probably wasn’t in a place personally or professionally to record it as episode 1.
I’ve avoided doing a “mindset” episode for almost 5 because I didn’t think it was necessary. I thought if people are seeking out business information, entrepreneurship information, they’ve already got the right mindset.
They know what’s up.
They get it.
But older and (hopefully) wiser, I’ve come to see the mindset conversation as an important one, and one I’ve been overlooking for a long time.
This is foundational stuff, and before you dismiss this as way to fluffy for a Side Hustle Show episode, let me give you a couple points to consider on the mindset front.
The first comes from one of my favorite podcasts, Tropical MBA. Their theory is for entrepreneurs making:
- $0-100k – the barrier is mindset
- $100k – $1M – the barrier is marketing
- $1M + – the barrier is your team
I’m sure there are counterpoints but I think there’s a lot of truth in that breakdown.
The second point to consider comes from Dane Maxwell. Dane created several software businesses before founding The Foundation to teach others what he’d learned.
He said the easiest way to test if your mindset is in the right place is to ask if you have or are you getting the results you want?
If not, something must be missing, right?
There’s some brutal honesty in that question, and it took me a minute to wrap my head around it, but the gist of it is this: if you’re not where you want to be, there’s room for some mindset growth or changes.
In this episode I’ll share 10 traits of the hustler’s mindset and do my best to illustrate those with examples from either my own businesses or those of my guests.
1. Hustlers Hustle
It probably goes without saying, but this has got to be #1.
Real businesses (even part-time ones) take real work.
And I should clarify, hustle doesn’t mean working 24 hours a day. It means taking control of the hours you can control, and putting your best effort forward in the time you have.
It comes from an old baseball coach of mine who said, “Hustle never slumps.”
2. Hustlers Keep an Open Mind
There’s no such thing as the “best” side hustle business. The best side hustle is the one you take action on.
I started out painting houses in college, and never would have expected that it would lead to building websites and hosting a podcast and writing books. (One of several ways I made money in college.)
In episode 254, you heard how Vincent Pugliese — a professional photojournalist — had a stigma against shooting weddings, but he was open minded enough to give it a shot. And within 4 years of hustle, he and his wife had paid off all their debt and were financially free.
The most important skill? The skill of learning new skills.
3. Hustlers Experiment
Try your ideas. Give yourself permission to test something out and see what happens, even if you don’t see it as a long term thing. Picking what’s next doesn’t mean picking what’s forever.
This is probably the biggest differentiating factor of the people who are building extra income streams and those that are stuck on the sidelines: a willingness to try something out not knowing for certain the outcome.
There’s no such thing as a failed experiment. Just stuff that didn’t go the way you expected.
Then you can learn from it, formulate a new hypothesis, and try something else.
- Every professional was once an amateur.
- Every bestseller started with a blank page.
- Every podcast starts with zero listeners; every email list with zero subscribers.
- Every freelancer starts with no clients and no portfolio.
- Everyone who’s “got it figured out” is still figuring out more each day.
4. Hustlers Bootstrap
There’s no shame in starting small. Most of my projects have cost less than $500 to get off the ground — most of them much less.
The point is you can do this stuff very lean, and it comes down to not making a bet you can’t afford to lose.
5. Hustlers Make Meaning (and money)
Do something you find fulfilling. That’s the whole reason this site and podcast exist.
The balance is it has to be both fulfilling and helpful to someone else.
6. Hustlers Ship
Perfection is the enemy of good enough.
If I was waiting for perfect, literally nothing I’ve done over the last decade would ever have seen the light of day.
I’m embarrassed by the first 50 episodes of this show — and a year from now I hope to be embarrassed by the content I put out today.
And remember, it’s still gotta be good enough — this one isn’t permission to ship garbage.
7. Hustlers Keep Their Goals in Mind
What’s your WHY?
It’s got to be worth it in some way or another. What’s motivating you?
Remember the AMP acronym: Autonomy, Mastery, and Purpose from Dan Pink’s Drive.
- Autonomy – “the desire to direct our own lives.”
- Mastery – “the urge to get better and better at something that matters.”
- Purpose -“the yearning to do what we do in the service of something larger than ourselves.”
If your day job doesn’t check those boxes, I think you can find a side hustle that does. And getting AMPed naturally leads to more happiness.
8. Hustlers Support Each Other
Entrepreneurship can be a lonely road. The journey is better together.
Start a mastermind group for accountability and feedback. These have been invaluable to me over the last 4 years, being able to tab into the collective brainpower and resources and connections of a group of like-minded entrepreneurs.
9. Hustlers Make Time
If you define freedom like I do as having control over your calendar, you can start to exercise that freedom today, even if it’s just in tiny little chunks.
It’s a challenge to unplug because the work is never done. That realization was really starting to wear on me last year and I’m still not sure the best way to combat it. One thing that’s worked is having 3-4 main priorities each day, and the day’s a win if I can accomplish those.
The other thing that’s been helpful the last few months is prioritizing a workout, usually in the morning or in the middle of the day. It’s tough to pull myself away from work, but I found the 20 minutes of getting hot and sweaty tends to make me feel better and more focused the rest of the time.
10. Hustlers Have Fun
Remember, it’s just a game. If it stops being fun, that’s probably a sign it’s time to stop.
How do you know when to quit? When you come to dread the work and you’re not seeing results.
- Ryan Finley on The Side Hustle Show
- Vincent Pugliese on The Side Hustle Show
- Bryan Harris on The Side Hustle Show
- Bryan’s “Figure it out” video
- The Journey is the Destination
- Alternative Investments (Prosper, Fundrise, and PeerStreet were mentioned in this episode)
- Finding Your Slight Edge
- Bjork Ostrom on The Side Hustle Show
- The Millionaire Fastlane
- Stacking Benjamins
- Drive by Dan Pink
- Theresa Campbell on The Side Hustle Show
- Think and Grow Rich
- Rob Dionne on The Side Hustle Show
There’s no secret sauce or magic bullet.
Learn from those who’ve gone before you. Help those who come behind you. Experiment, practice, pivot, and give it time and you will see results.
What did you think of this episode? Helpful? Or not so much?
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