The Pros and Cons of Juggling a Side Hustle and a 9-to-5 Job

When I first started using PocketSmith, I had a single income category labeled, simply, “Income”. Color code: Green.

Then my work life got a little more complicated. Eventually I up-ended the whole system and started over. Now I use an “Income” parent category, two main sub-categories, “Freelance” and “Other”, and a host of subbier-categories across three layers, from project type to individual clients.

All’s well that ends well, you might say. But it’s not the end, and that’s never the part that interests people. They don’t ask, “What’s your end-goal system?” They ask, “How did you get there?”

Sorry to disappoint you, but I didn’t wake up one morning, quit my day job, and launch a full-time freelancing career by lunchtime. These things take time. A 9-to-5 job has its pros and cons. So does that #sidehustlelife. Let me take you through a few of them.

Pro: Slow and steady growth

I started freelancing seven or eight years ago, through a friend at church. He needed some transcribing done and, with a travel-heavy work schedule, didn’t have time to do it himself. I was working part-time and could do with the extra income. He’s been my most consistent client over the years since; in fact, he pays every invoice within 24 hours of receipt.

Was it busy at times as I balanced his work against various day jobs? Sure. But our timeframes are always flexible. His work is seldom red-flag-urgent, and as a way to lay a solid foundation, it was ideal. I built up my regular income levels and built my client base at the same time.

Con: Knowing when to make the leap

I’ll be honest: If I hadn’t just finished a 12-month contract with no ‘next step’ lined up, I might never have gone full-time freelancing. I didn’t have enough clients at the time to justify it. But I also knew that, unless I put serious effort into growth, this side hustle would stay a side hustle. It would never become anything more. And I would never have the time or energy to grow it while I was still working a regular 9-to-5 job.

I checked my income/expense budgets in PocketSmith, made sure I had a good balance in my emergency fund and took the plunge.

Pro (and Con): Consistency

If there’s one thing that would tempt me to go back to a 9-to-5 job, it’s the consistency. Routine. Structure. You get up, go to work, come home. Leave work at work. There’s far, far less decision fatigue. Life, and finances, are more predictable. You know where your next paycheque is coming from. You can budget the same amount of income every month — even every week! That’s something I haven’t been able to do in more than two years.

If it gets too stifling? Too predictable? Too boring? Well…

Pro (and Con): Flexibility

By contrast, being self-employed is the epitome of flexibility. If I want to take Fridays off, I can (and often do). If I find one client more interesting on the day, I can shuffle projects around without worrying about my boss yelling at me. If I want to vanish off overseas and work that #digitalnomadlife for six months across Canada and the UK, I can. My budgets have to be similarly flexible, though. If I didn’t have PocketSmith’s automations to help manage my day-to-day budgeting, I’d be well and truly lost. My old spreadsheet budget could never have handled the amount of irregularity and vague deadlines that PocketSmith does.

If it gets too unstable and starts feeling like too much of a rollercoaster, then…

Pro: Finding the balance

Juggling a day job and a side hustle can be a tricky balance. There have been times I was working 50-hour weeks at the office, coming home to put a few hours into the side hustle at night, and then studying at the weekend. As if I wasn’t busy enough! It was unsustainable as a lifestyle, and I knew it. The adrenaline surge only carries you so far. Sooner or later, the crash is coming.

Get the balance right, though, and it’s the best of both worlds. On one side, you’ve got a steady income, a solid career track, a good team around you, and your taxes and retirement contributions are all done for you. On the other side, you’ve got the potential to out-earn anyone in your circle and you can set your own schedule for the week — and the year.

And hey. Don’t stress it. Nothing is permanent.

You might find that balance, try it for a while, and decide it’s not for you. You might go full-time one way or the other, ride the wave for a few years, and then make the transition back to the other side. Like any PocketSmith setup, you’ve got a whole range of options out there. And that optionality can only be a good thing.

Rachel E. Wilson is an author and freelance writer based in New Zealand. She has been, variously, administrator at an ESOL non-profit, transcriber for a historian, and technical document controller at a french fry factory. She has a keen interest in financial literacy and design, and a growing collection of houseplants (pun intended).