267: The Hustler’s Mindset: The 10 Traits of Successful Side Hustle Entrepreneurs

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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.

Consider this:

  • 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.

Join the free Side Hustle Nation community on Facebook.

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.


Your Turn

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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Nick Loper

About the Author

Nick Loper is a side hustle expert who loves helping people earn more money and start businesses they care about. He hosts the award-winning Side Hustle Show, where he's interviewed over 500 successful entrepreneurs, and is the bestselling author of Buy Buttons, The Side Hustle, and $1,000 100 Ways.

His work has been featured in The New York Times, Entrepreneur, Forbes, TIME, Newsweek, Business Insider, MSN, Yahoo Finance, The Los Angeles Times, The San Francisco Chronicle, The Financial Times, Bankrate, Hubspot, Ahrefs, Shopify, Investopedia, VICE, Vox, Mashable, ChooseFI, Bigger Pockets, The Penny Hoarder, GoBankingRates, and more.

7 thoughts on “267: The Hustler’s Mindset: The 10 Traits of Successful Side Hustle Entrepreneurs”

  1. hey Nick! I listened to this one on my ride to work this morning, great stuff! You definitely made a number of great points but the one I most identified with was #8. I too have often found myself to be a lone wolf as a blogger and I believe it has really held me back. I’m making more of an effort to connect with other bloggers and build relationships going forward, though it is easy to fall back into my introverted comfort zone if I’m not focused on being social.

  2. Lately I am a firm believer that #3 also has to do with expectations. If someone starts a podcast, selling on FBA, Merch, a cleaning company, or whatever else is popular at the moment, and goes into it with preconceived expectations on what is going to happen then it is a lot easier to “fail”. If you start a hustle but think that you are going to quit your job next month because you’re rolling in cash since Joe the guru told you so, if you only actually make a few hundred it leads to burnout (not receiving just rewards for your effort) and a failure. But the reality is that a few hundred extra is not that bad, and if you come in with an open and experimental mind instead of getting rich quick, it leads to a whole different mindset. In fact this is actually a big one with myself right now because if I would have kept all the small projects I’ve started and put the hour a month into maintaining them, then I would be far better off right now.

  3. Hey Nick. Just finished this episode. To be totally honest, I almost passed over it because “mind set”. But man, i’m glad I listened. Really good points Nick. For me, the struggle is with #8. Like you, I’m a lone wolf by nature. I try to do everything on my own. I’ve known for a long time that joining a mastermind group should be a top priority. But i have such a fear of criticism and failure, that I’ve never joined one. Fact is, I don’t even belong to a single Facebook group. So that’s my biggest struggle. And if I were to add an 11th to your list, it would be to confront and expose our “inner voices” or fears. You know, the ones that tell us “it’s not good enough” or “no one will like this”. Some of my fears of failure are so severe that I’ve never even invited my wife to view my websites or blog posts. So sad, I know. I’m reading through John Acuff’s book ‘Start’ right now and he mentions physically writing down those fears or “voices” to expose them. And once they’re actually written and voiced out loud, they sound ridiculous. This has been helping me with my fear of joining a mastermind and other groups, like on FB. And to actually involve my wife and other loved ones on my side hustle journey. Thanks again Nick. Keep it up!

    • Thanks for sharing Don! I’m with you. I was deathly afraid and intimidated to practice my TEDx talk in front of friends or my wife. For whatever reason it was way less vulnerable to share with strangers :)

  4. Hey Nick, loved this one. I’ve always been a fan of mindset learning. I know the importance of mindset and know my blocks (not feeling good enough!) but don’t know the reason for that block. Don’t you find that a lot? These damn blocks come up but finding where they came from in order to “fix” them and create a new mindset is the toughest part. Who would’ve thought that becoming an entrepreneur or starting any side hustle would mean ending up feeling like you need a degree in your own psychology! Grrr!
    Thanks for this though! We’ll all get there, wherever “there” is! Xoxo

  5. Great episode! I LOVE number 2. Hustler’s keep an open mind. When I was thinking about adding on an MLM as an income stream, I delayed that choice because others had failed.

    When I chose to educate myself about that business model, learn why many fail, and how not to fail, I finally started to enjoy learning about the sales process. (If you can generate revenue for someone else, you can do it for yourself.) …oh and speaking of…Fall in LOVE with the process, unsure where that was mentioned, but that was a good tip too.

    Again, great episode!


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