248: 12 Steps for Starting & Scaling Your Creative Side Hustle (Pt. 1)
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I get hit up a lot with questions of, “How do I get started with my creative side hustle?”
There’s no one-size-fits-all instruction manual— it requires a lot of patience, experimentation, failure, and figuring it out along the way.
In November 2021, I got an email from subscriber/new homie, Neil Botham, where he asked a similar question.
He basically wanted to figure out a starting point for pursuing his photography passion as a side business outside his IT day job.
While also navigating how to find the time, energy, and motivation to do this outside of being a dad of 3…
Along with navigating the head games we all face such as comparison, imposter syndrome, depressed funks, burnout, etc.
What you’re hearing today is a more in-depth version of my email response to him.
I’m hoping this can reach a lot more people in a similar position to Neil if I share:
My rollercoaster experience of taking my side hustle to dream hustle.
How I slowly built a foundation and scaled outside a day job, family, and life responsibilities.
What I’ve learned from hundreds of convos I’ve had with heavy hitters in the game who shared their successes (and failures) with me.
His question inspired this 2 Part Series of How to Start & Scale Your Creative Side Hustle.
Part 1 will be about getting started.
Part 2 will be focused on slow and steady scaling.
Many of these tips are interchangeable and overlap within different seasons of your creative hustle—it’s not necessarily a linear progression of each 12 steps in a row.
This is simply a framework to guide someone on a path that:
Reduces the guesswork and boosts clarity and confidence.
Provides balance and structure to leverage in the long-term.
Creates work they love while establishing boundaries for self-care and relationships.
Overall, take what applies to you as everyone’s path is unique.
Let’s dive in…
1. Take Yourself Seriously
The true key to finding success with your creativity depends on developing between your ears.
Mindset is everything, as you’re playing a difficult game built on navigating internal and external critics.
The world is a mirror…
The more you take yourself seriously, the more the world will start to align with what you believe about yourself.
If you treat your creative pursuits like a hobbyist, doing it when it’s convenient, the world will view you as a hobbyist.
You don’t need to do your thing full-time and be profitable in order to operate like a professional.
Even in the early stages, showing up intentionally each day, showing yourself in your work, and cranking out art/content consistently will show people over time that you’re a force to be reckoned with.
Discipline is great, but true change is sparked from a deep burning desire…discipline and habits are shaped from this desire.
So basically, how badly do you want it and what are you willing to do (or not do) to become a successful professional?
2. Have a Target
It’s helpful to have a basic understanding of WHAT you want and WHY you want it?
Simply start by giving yourself a target to work toward—if you can see it in your mind, you’re one step closer to achieving it.
This macro focus and intent will guide your efforts when you show up in the micro.
Start by asking yourself:
“If money wasn’t a concern, what would my creative dream job look like?”
Followed up by:
“What would I be creating and in what dope places does my work exist?
“What dream clients/brands am I working with?”
“How much am I making?”
“What does the perfect day in my dream job look like?”
Be specific AF with your answers. Once we understand what we want during this season, we can take steps toward reaching them.
I want you to feel hella uncomfortable and ridiculous for dreaming that these farfetched fantasies are possible…
Because most people never give themselves permission to dream out loud, which keeps them living a small, bitter life.
The more you get these out of you and where you can see them each day, the less scary and more realistic they become…it’s all about rewiring your mind.
Finally, embrace that your targets can and WILL change as you evolve and grow over time.
(We’re all just little Pokemon trying to evolve into our ultimate, most successful forms.)
3. DON’T Focus on Money.
You're NOT a failure if you’re not making money right away with your work.
Chasing the paper when you're finding your creative groove tends to scare the cheddar away.
You can't force the process—the more you connect with your art, the more your future fans will connect with it, too.
When you’re starting off, or finding your groove, eliminate the need to monetize right away.
This reduces the pressure to make it successful overnight—this shit takes time, and there's power in organically evolving and the opportunities/answers that’ll come your way.
Finding both your creative gift AND yourself in your work is the foundation for success…
But obsessing over the money (and vanity metrics) as a measure of your performance/success is the quickest way to suffocate the joy.
4. Keep it Purposeful Play
Sure, we scheme up targets to be intentional, but we still gotta make sure we approach this from a purposeful play angle.
Doing your thing full-time successfully one day should be rooted in play…
Because that’s what will push you through the hard times and the non-glamorous parts of running your own business.
(Taxes, accounting, and admin work, anyone?)
Don’t lose sight of play and trust/believe that this can (and will) scale to something bigger in due time.
At the end of the day, if you’re not having fun, it’s just another soul-sucking day job.
5. Find Your Secret Sauce
With so much noise out there in the world, bringing something to the table that is uniquely YOU will stand out from the trends and copycats.
I call this “Finding your Secret Sauce.”
My interpretation of this concept is made up of a 3-Part Recipe:
Your story and experiences.
Your strengths and skills.
Your core identity ingredients (interests, passions, beliefs, and values).
The goal ISN’T to share everything…but to pick and choose a select few ingredients to experiment with for a season.
This allows you to show up as your true self while serving up a dish that overlaps something you’re good at/desire to be great at with something you truly enjoy/are interested in.
You may be wondering, “How do you define what a season looks like?”
A season is arbitrary and subjective, varying from each individual’s desires, needs, and circumstances.
For one person, a season could look like me in 2016 dedicating 2 years to building up the podcast to see what happens.
For another person, a season could look like an intentional personal project series of 10 pieces over 3 months (more on these types of projects in step #6).
Notes: I originally came up with this idea way back in Episode 161: Finding Your Secret Sauce.
I’ve since revamped this concept into an in-depth exercise within the Side Hustler’s Handbook Interactive Course for Creatives.
6. Create Intentional Personal Projects
When you have a target to shoot for and you have a 1st draft Blueprint of what your Secret Sauce could be…
The fun part is bringing it to market and testing it through intentional personal projects.
These are meant to showcase who you are plus your talents…
All while aligning with the big picture direction you’re steering your ship.
Constraints
Constraints are a powerful way to simplify the game while providing structure.
Constraints breed creativity and confidence because there’s less margin to overthink.
Staring at a blank artboard with unlimited possibilities can overwhelm and paralyze us from getting lost in the sauce…
That’s not a happy, productive headspace to tap into your best work.
Example: Here are some constraints me and my students leverage:
Limited color palettes, medium, subject matter, theme, how much time you’ll work on it, days and times you post, the platform you leverage, type of post (short video, static image, audio, etc.).
Series
Are you too afraid of feeling pigeonholed into one direction and style?
Do you have a lot of ideas, mediums, and themes you want to test out?
If so, consider doing things in sprints…
More specifically, small batches of series or collections where you can test the waters and create small bodies of work.
If you vibe to the project, you can always expand and do more, or pivot and onto the next idea.
Example: Here’s how you could plan an Intentional Personal Project:
Create a small series of 5 digitally-drawn Halloween-themed gift card designs (because Halloween and spooky shit is your jam) with the goal of getting hired to do gift cards for places like Target, Michaels, etc. one day.
You’ll spend a max of 5 hours on each with a frequency of posting the final static art and final mockup as a Reel every Tuesday and Thursday at 12pm CT on Instagram.
Note: I provide actionable exercises on how to build Intentional Personal Projects in the Side Hustler’s Handbook Interactive Course for Creative.
What I Needed Starting Off
Again, there’s no instruction manual as to how to build a successful creative side hustle.
I hope this series puts you in an incredible position to gain traction and bypass the hurdles I went through over the years.
It’s truly a “loose” framework I wish someone would’ve shared with me early on…it would’ve spared me a ton of guesswork and headaches.
Stay tuned for steps 7–12 next week; we’ll dive deeper in scaling after you’ve established your foundation.
And if you want more hand-in-hand guidance on how to navigate these steps…
Consider joining the 12-Week Side Hustler’s Coaching Program Waitlist for the upcoming Spring 2022 session.
We will condense all 12 steps you hear in this series, so you can fast track your way to rapid growth with the support of a coach and tight-knit family holding you accountable.
Q1 Side Hustler’s Boot Camp enrollment is live!
Enrollment is open Wednesday, January 19th - Thursday, January 27th!
This is a 3-Week Planning, Strategy, and Execution-based Group Coaching Live Workshop that will radically set the tone for your 2022 and beyond.
🗓 We kick-off Saturday, January 29th - Friday, February 18th.
Credits
Music - Blookah
Executive Assistant - Paige Garland
Video Specialist - Jared Cunningham
Social Media Coordinator - Hannah Schick
Animation Specialist - Greg D'Amico