Seven Mindsets of a Wannabe Side Hustler

Tim Denning

There’s nothing wrong with wanting to be an after hours wannabe and building something you own.

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Photo by Rustem Baltiyev on Unsplash

We all start out as wannabes.

We want to be a side hustler because being a day-to-day hustler has burned us out. Seeking change sends us down the path of side hustling. Side hustling is simply the desire to work on a small project before and after gours. It’s innocent. Don’t let internet haters tell you a side hustle is evil — it’s your human right if you choose.

As a side hustler, here are the mindsets I see amongst the fifty other side hustlers I spend most of my time with.

You want to fuse your passions with your work (and get paid)

Most of us live in two distant worlds. One world is our day job. The second world is what we like doing.

I lived like this for years. During the day I’d roll up to a bank and clock in. At night I would write about self-improvement — not because I like 4 AM cold showers, but because self-improvement saved my life when I endured the torture of mental illness and had lost all hope.

Self-improvement changed my life. When something changes your life, you want to share it with others. This form of work creates many secret millionaires. The challenge? Taking something that changes your own life and allowing it to change the lives of others isn’t a switch you flick. The transition between your current day job and that thing you love is a slow grind.

The phrase side hustle simply explains the transition between work you don’t enjoy and work you love. At one point, the amount of work you do in your day job and the work you do in your side hustle, flips. You go from doing slightly more work on your side hustle than your day job.

I don’t say this stuff out of nowhere. I am proof. It happened to me. I went from working jobs to pay bills, to doing what I love: a fusion of self-help, writing, teaching, social media, and entrepreneurship. But don’t think the transition will be easy. It won’t be and it’s not supposed to be.

Doing work you truly love, that you’ve waited your entire life to do, will take time to transition to. But isn’t it worth it?

You want to own it

I am tired of building other people’s dreams.

I want to build my own thing even if it’s pissing in the wind compared to owning a billion-dollar startup. It’s not the size — it’s that it’s mine and nobody can tell me to get out of my own home office and find another way to make money. Nope.

The company (LLC) is in my name. The only way I get fired is when I die. Otherwise, you’re going to have to fight me out of this line of work, even if I’m 104-years-old. I’ll still be hustling. I’ll still be writing stuff and hitting publish, even if it’s about the best retirement village my friends are dying in.

Ownership is a mindset. It’s why owning a home is a huge deal for society. Well, you should bloody well own your life’s work. Screw them.

You’re tired of bad decisions at work

My previous job involved selling. A person who worked with me lowered the pricing to the customer by more than 20%. As a result, they made everything we did unprofitable and wiped out all of my KPIs overnight. I got zero bonus, which was most of how I got paid. (Pass the tissues.)

These types of bad decisions are normal in the corporate world. It doesn’t mean you need to continue to witness this nonsense every day. Side hustlers have the mindset of “I’ll make the bad decisions, thank you.”

That’s how I feel. A guy scammed me recently out of a website upgrade. He’s sipping pinot coladas with his cousin in Mexico. No more replies to emails. While I’m an absolute wood duck for paying all of the money upfront, I like that it’s my bad decision to own and learn from.

*Does Borat voice* It feels nicccee.

You want to make the bad decisions. Doing feels better than observing.

You want to make your money from more than one source

One income source feels scary. All it takes is your boss to get a pair of tiny plastic scissors and cut off your salary. We saw it during the lockdowns. Companies simply said, “Sorry mate, see ya later alligator. We gotta save money so we don’t care about you anymore (hint: they never did).”

Two income sources feel like freedom. Three feels really good. The average millionaire has seven income sources.

You want the “work anywhere” freedom of the online world

Digital nomad is a label. God I hate labels. The term has got a bad wrap.

When I say work from anywhere, I’m not referring to the laptop life as a digital nomad. Nope. I’m being much more simplistic. Work from anywhere means working from your home, or a WeWork over the road, or your brother’s house, or from a caravan, or from the destination you’re at while taking holidays.

Eventually, I believe we’ll all be working from a place like Decentraland that’s full of virtual offices. You put on your VR goggles and all of a sudden the clarity of what you see and hear is the same as the real world, therefore a virtual office gives you all the same in-person benefits. Except if Karen from operations wants to chat and ruin your life. Then you just take off your VR goggles right before she makes it to your desk. Niceee.

Work from anywhere is simply the mindset “I don’t want to live in a crowded city anymore and be in mountain of debt to be close to a physical office.” Live three hours from the office and enjoy huge savings. Or better yet, do side hustle work that leads to an office in Decentraland. VR is freedom.

Chosen schedule versus a schedule chosen for you

Wannabe side hustlers hate having executives that are bonkers put stuff in their calendar. We want to own our calendar. I call it Outlook Freedom.

When I choose my schedule stuff gets done. When a huge corporation has the freedom to put meetings in my diary for thirty minutes each, with more than 100 people crammed into a Zoom call, where each person (if everybody spoke) gets less than 18 seconds of talk time, the day disappears like a magic trick. 8 hours turns into an 8 minute lunch in between calls.

Outlook Freedom provides higher per minute returns on your time.

Why not me?

Wannabe side hustlers are slightly optimistic. The mindset we have is “why not me?” We believe there is a better alternative than working for the man to earn dollars that are created out of thin air by governments.

Now, we’re slightly delusional too. We miscalculate how long it takes to transition from side hustle to quitting the regular working world. But we believe it’s possible. We believe there is a better way to live even if we have to do this multiple times and have it explode. Success as a side hustler is far too great of an opportunity not to try and fail multiple times.

We all start out as wannabes in life. The wannabe way of life is how you become a somebody in your own eyes. I’m not going to lie — going from normal work all the way to side hustle work isn’t easy and it’s not going to happen quickly. But here’s what I learned: a combination of a side hustle and a normal job works wonders. Why?

Well, even if you haven’t achieved your wannabe goal, the fact you’re on your way, and building your tiny empire, is a deeply rewarding and motivating feeling. It’s not the end that feels good. It’s the process of reaching your side hustle goal that makes it all worth it. It’s okay to be a wannabe side hustler. Your critics simply want the same, they just haven’t realized it.

Be a wannabe side hustler for a few years and watch it improve your life.

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Aussie Blogger with 100M+ views — Writer for CNBC & Business Insider. Inspiring the world through Personal Development and Entrepreneurship www.timdenning.com

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