Scaling Beyond Yourself: Working ON Your Business, Not IN It
- Cassie Wilson
- 26 minutes ago
- 3 min read
Sigh. I created myself a job instead of a business.
Now, I’ve been down this road before: getting completely lost in the daily operations of my business - fielding all the calls, doing everything administration, being present on the frontline - all while trying to strategically scale. What I can tell you is that there’s no one way to do it. When bootstrapping, growth isn’t always linear and you’ve gotta get quite scrappy until you hit your “big break” and have the advantage of cashflow.

My breaking point was the inability to digitally check out, there was no separation between myself and the success of my business. Putting my phone on DND resulted in huge loss, and I couldn't take a vacation without my phone blowing up. Drowning in emails, stressing about social media, creating/updating/following up on invoices, completing supply orders, and managing staff schedules was my life.
The business ran me, not the other way around.
The Harsh Truth
If your business can't run without you for a week, you don't own a business - you own a job!
My Action Plan for Freedom (& Maybe Yours Too)
Phase 1: The Audit
List every single task I do in a week (yes, even the 2-minute ones!)
Categorize tasks: Must do personally vs. Can delegate
Track time spent on each task (I was gagged at how much time was wasted on low-impact activities)
Phase 2: Delegation/Hiring
Hire a VA: Start with 10 hours a week for email management and basic admin (if you’re on a budget, you can absolutely outsource this to another country, don’t feel bad for that shit)
Social Media Management: For me, I focussed on batch creating content and scheduling it to release since social media doesn’t really drive business - it’s just a nice portfolio piece. Some businesses might want to invest in an actual social media manager instead.
Staffing: Never have I ever hired someone directly from a job posting. When I see talent, I pounce on it, because it's so rare. I'm also ALWAYS asking my network for referrals. The more capable my team, the better it is for me and the business.
Pro tips for hiring:
Don’t try to hire everyone at once. Total chaos!
Hire slow, fire fast
Use contractors whenever possible
Tap into your networks to find the right people
Your competitors aren’t always your competitors. I’ve served overflow clients by outsourcing work to other companies (this tends to be more expensive, but you still get the client at the end of the day)
Phase 3: Systems
Time to make yourself replaceable (in the best way possible):
Create SOPs for everything - even tasks you think are "too simple" to document
Set up automated workflows for repetitive tasks
Build templates for common responses and processes
Onboarding processes
The Scary-But-Worth-It Investment
Hiring help costs money. It's terrifying. But here's the truth: the more freed up time I have to establish new contracts, the more sustainable of a business I’m building.
Sometimes you have to spend money to make money (apparently that isn't just a cute saying)
Your Permission Slip
Consider this your official permission to move towards a business model where you can:
Step away from the day-to-day operations
Let go of tasks that drain your energy
Focus on strategic growth (the fun stuff!)
Take an actual vacation without your laptop

Building a real business means building something that can thrive without you being involved in every little detail. It's scary, it's expensive, there will be fuck ups, and it's all absolutely worth it.
Now, excuse me while I go work ON my business instead of IN it!
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