Entrepreneurial Side Hustles That Can Turn into Full-Time Businesses
It shouldn’t be a huge shock, but almost all companies started are a byproduct of a side hustle. A side hustle is working after your primary job on something your interested in for additional money or fun.
I mentioned this in my first video, I started my IT services company while working two other full time jobs at the time. There are some key rules when it comes to a side hustle that I really believe in.
A side hustle is just that, something on the side, it must be done on your time not on the time of your current employer.
It’s really important to me to reiterate that your current employer pays you for your time and does not let your side hustle impact or interfere with your ability to perform your core job.
When it comes to the side hustle, the moment it does start to impact your ability to do your full time job is the moment you know its time to make the shift from full time job / side hustle to focusing on your side hustle full time.
When providing IT services, how did I make a side hustle work? First I was very clear with my clients that I was a freelance IT consultant. This meant that I was setting a clear expectation, that I was doing this on the side and that I had an existing full time job.
This meant my first IT services agreements meant outlining support after 6pm most evenings and or weekend only support. In the IT services industry these are normally unsupported windows of time, for many this was more than fine with them as they had more time to work on IT issues past their normal 9 to 5 as well.
What I learned was that its ok to do something you love outside of work. I learned that its important to set clear expectations and boundaries early even in the side hustle phase and its important to understand where that metric for success is that is an indicator that its time to phase out your full time job in favor of your side gig, whatever that happens to be.
For me the metric of success was getting more clients who wanted my services than I had time to support, after 10 people was added to my waitlist, I knew I had something that could sustain and required a more full time approach.
Remember having a side hustle is ok. Michael Jordan said it best. Some people want it to happen, some people wish it would happen, others make it happen.
AI Usage Transparency Report
AI Era · Written during widespread use of AI tools
AI Signal Composition
Score: 0.1 · Low AI Influence
Summary
The article discusses the importance of having a side hustle and how to make it work, including setting clear expectations and boundaries, understanding metrics for success, and knowing when to phase out a full-time job in favor of a side gig.
Related Posts
Clamshell iBook G3 Restoration, Part 1: From Broken Screen to Board-Level Repair
Part one of a Clamshell iBook G3 restoration: a broken screen, a charger detour, a blinking system folder, a full teardown, and the backlight connector mistake that paused the project.
Bromure Gives Codex a Room of Its Own
I installed Bromure Agentic Coding, watched it build the Linux VM, authenticated Codex, and followed a real Codex task through the workspace.
Claude Code Auto Mode Changes Approval Flow, Not the Safety Boundary
Claude Code Auto mode changes how approval decisions are handled. It does not expand the boundary of what the coding agent should be allowed to do.
Amnesia Stealer Shows the Next Stage of ClickFix on macOS
Amnesia Stealer shows how ClickFix-style social engineering is adapting on macOS, while a public malware sample gives defenders an opportunity to study the behavior behind the campaign.
Reporting on Microsoft 365 DLP Overrides with PowerShell
DLP overrides are not automatically bad. They are a business process that needs visibility. This walkthrough covers a Microsoft Purview DLP policy, a custom sensitive information type, user override behavior, and a PowerShell report that exports override events from Activity Explorer.
PowerBook 140 BlueSCSI Install: Cable Fixed, Battery-Bay Power, and Wi-Fi Setup
The PowerBook 140 project moved from preparing a BlueSCSI card in Basilisk II to installing the repaired internal SCSI cable, powering the BlueSCSI Pico externally from the battery bay, booting System 7.1, and fighting through DaynaPORT Wi-Fi setup.
Move Entra Users Off SMS and Voice Before Microsoft Retires Them
Microsoft is retiring Microsoft-provided SMS and voice authentication in Entra ID. The migration is not passkeys for everyone; it is removing weak telecom MFA and choosing supported replacement methods such as Microsoft Authenticator, FIDO2 keys, certificate-based authentication, OATH hardware tokens, or customer-managed telecom.
Fixing a Broken Apple Cinema Display Stand with a 3D Printed Leg
A 22-inch Apple Cinema Display arrived with a broken acrylic easel stand, so I used a 3D printed replacement leg instead of sending the monitor back.
macOS Tahoe 26.6.1 Fixes a High-Severity Screen Sharing Authentication Bypass
macOS Tahoe 26.6.1 fixes CVE-2026-65400, a high-severity Screen Sharing authentication issue where an attacker on the network may be able to authenticate without valid credentials.
Three Mac Update Helpers That Fit Below a Patch Platform
Latest, Applite, and an all-in-one macOS update script each solve a different part of lightweight Mac maintenance: app update visibility, Homebrew-backed app management, and command-line package updates that can be wrapped carefully for small teams or basic MDM.