Making the Jump: From Side Hustle to Full-Time

I’ve been freelancing since 1996. Started as a side hustle while working at a digital agency - late nights, early mornings, weekends. Eventually made the jump to full-time, but those side hustle days taught me something crucial: if you’re serious about making this your main thing, you need to know exactly where your time goes.

Most side-hustlers I meet are brilliant at their craft. Terrible at tracking their time. They’ll spend three hours perfecting a logo, bill for one. Forget to log that Sunday morning client call entirely. Undercharge because they “weren’t really working.”

The Scattered Life of a Side-Hustler

Your work happens in fragments. 7am coffee shop session before the commute. Lunchtime client calls between meetings. Weekend marathons when the house is finally quiet. Late-night sessions after everyone’s asleep.

The context switching is exhausting. Corporate strategy meeting at 2pm, sketching logo concepts at 2:15pm. Balancing family time with client deadlines. Managing two professional identities. Finding space to be creative when your brain is already done for the day.

But the real money drain? You don’t value your work properly. Two hours flipping through logo inspiration books, doodling concepts, researching typography for a client’s brand - but you only log 30 minutes because it felt more like playing than working. That branding breakthrough while you’re sketching ideas on the shower glass never gets tracked because it doesn’t feel legitimate. Every minimised hour is money you’re not charging for.

The Real Cost of Bad Time Tracking

You quote a website at $2,000. Twenty hours at $100/hour seems fair.

Then reality hits: one hour for the initial meeting, three hours of research and planning, 22 hours of actual work (scope creep is real), four hours of revisions and feedback calls, two hours for final delivery and handover.

That’s 32 hours for $2,000. $62.50 per hour.

Without tracking, you’ll repeat this mistake on every project. Keep underestimating, keep undercharging, keep wondering why your side hustle feels like hard work for mediocre money. With tracking, you spot the pattern. Start pricing based on reality instead of optimism.

The Invisible Work That Adds Up

Side-hustlers forget to track the work between the “real” work. That quick phone call becomes a 20-minute strategy session. Email chains eat up hours across several days. WhatsApp messages feel too casual to log, but they’re still your expertise being delivered.

Then there’s project-specific research. Understanding your client’s industry, finding reference materials, researching technical requirements, studying their target audience. This isn’t general learning – it’s specific work that benefits their project.

Problem-solving time is massive. Troubleshooting technical issues, testing approaches, debugging code, working through layout problems. File preparation, quality checking, documentation, training clients on what you’ve built.

All of this is work. All of this should be in your invoices.

Building a System That Works Around Your Life

Your side hustle happens everywhere except a traditional office. Your tracking system needs to be mobile-first and lightning fast. Sketching on the train, client calls during lunch breaks, late nights at the kitchen table, inspiration strikes during weekend walks.

You need something that captures work in 30 seconds max. Something forgiving enough to backfill forgotten sessions. The key is making tracking automatic. When you switch projects, log the previous task immediately. Before you pack up, quick mental scan of what you accomplished.

The Mindset Shift

Track your time for a month and you’ll notice something. You start taking yourself seriously. You’re not “doing some design work on weekends” – you’re running a design consultancy that operates outside traditional hours.

This changes how you price projects. How you talk to clients. How you plan your future. You stop apologising for your rates. Start managing scope properly instead of rushing to keep clients happy.

When you can see “I earned $2,400 last month working 15 hours per week,” the path to full-time becomes clear. You know exactly what you need to replace your salary. Real data, not guesses.

Making the Leap

The side-hustlers who make it to full-time? They treated it like a real business from day one. Tracked their time, knew their numbers, had data to back up the decision.

Without tracking, you’re guessing. With it, you know exactly when you’re ready.

Steve Leggat has been freelancing in design and web development since 1996, starting as a side-hustler while working at a digital agency. He runs Front&Back, a solo design company in Auckland, and created TallyHo specifically for freelancers who want to capture their time naturally without breaking their flow.