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How to Juggle Jobs

I Choose to Juggle 3 Jobs — and Love It

Taking on multiple jobs is not always easy. LearnVest shares the story of how one person takes on three careers and loves every moment of it.

In our Money Mic series, we hand over the podium to people with controversial views about money. These are their views, not ours, but we welcome your responses.

In his last essay for LearnVest, Sean shared his master plan for paying off a large chunk of his home loan in "How I Paid $100,000 Off My Mortgage in Under 2 Years." Today, he talks about how income from two side gigs is helping him to further put a dent in his mortgage — and why he relishes every moment of his jam-packed work life.

It's 5 a.m. and although the sun hasn't yet risen, I've already started my workday. Around this time, you'll usually find me typing away on my laptop because mornings are when I'm most productive.

Why am I up at the crack of dawn when I could be catching some much-needed shut-eye? It's because I have three jobs — and not because I have to, but because I want to.

My regular 9-to-5 has me working as a pension analyst at a global pension and benefits consulting firm, where I make about $49,000 a year. But I also work two side jobs: I have a part-time, weekend position as a meat-department clerk at a supermarket, and I write freelance articles about finance at night and on weekends.

My family and friends often ask me why I choose to work three jobs when many people struggle just to keep up with the hectic pace of one — especially since my salary can sustain my current lifestyle. But I've always had a strong work ethic, plus I have financial goals that won't happen on their own. And my extra income helps me form a game plan to achieve them.

Why Having Three Jobs Is Worth It (Really!)
One of the goals I'm working toward is to pay off my mortgage by age 31—and that's only about three years away. As such, I route much of my side-job income directly toward paying down that loan, and at the rate I'm going, I expect to meet my timeline.

I'm able to do this thanks to a couple of moves I've made. For starters, I rent the main floor of my house for $1,550 per month, while I live in the basement. And since I know that the pay from my supermarket job is a reliable source of income, I increased my mortgage payment to include that amount.

Last year, I earned $10,000 from my supermarket job, and brought in an additional $20,000 from my freelance writing — making it my most successful year to date.

Although I earn a lot more writing, the one downside is that it's often hard to predict how much I'll earn from month to month. For this reason I treat my freelance writing income as "found money," and as soon as I receive a check, I apply it as a lump-sum payment toward my mortgage. And since I'm in a higher-income tax bracket due to my side jobs, I make sure to contribute $300 a week toward retirement savings to lessen my tax burden.

In less than two years, I've managed to pay off more than $100,000 of the $425,000 mortgage on my home in Toronto using my side income and my rental income. This extra money also helped pay for $25,000 worth of recent home renovations — installing a new retaining wall, a sump pump, a sidewalk, and a front porch — so I'm glad I had the financial cushion.

How I Manage the Three-Job Juggling Act
Between my full-time job and the side jobs, I can work upwards of 80 hours in an average week. In addition to waking at the crack of dawn, I go to bed at midnight. It also helps that I'm currently single, which enables me to keep up with this pace.

Once I've achieved my goal of mortgage freedom, I'll scale back my workload by quitting my part-time supermarket job, and only taking on select writing assignments. I'll also likely stop renting out the main floor of my house, but I'm in no hurry.

A lot of how I budget my time is based on an idea espoused by one of my idols, Mark Cuban, star of ABC's Shark Tank and the outspoken owner of the Dallas Mavericks. One of the philosophies he often preaches is a metric they don't teach you in business school: return on time — the idea that you should value every minute.

I use this principle in my daily schedule. Sometimes there are simply not enough hours in a day to get everything done, so I look at the tasks that will achieve the greatest return. As a freelance writer, I'm often juggling many tight deadlines, so it's important to manage the ones that matter most.

I generally try to tackle what's due first, but when my workload becomes too heavy, I'll focus on the most lucrative assignments. I also prioritize personal tasks based on their urgency. For instance, if the lawn is mowed on another day, it's not the end of the world. But if I don't tackle the laundry, I'm out of luck for tomorrow's work clothes.

Every morning, I also make a to-do list in my head of what I hope to accomplish that day, both personally and professionally. I find that once I set a specific goal, it's a lot easier to achieve. My date planner becomes crucial to helping me manage these everyday tasks.

Despite my busy schedule, I also try to schedule get-togethers with those nearest and dearest to me at least a week in advance. Sure, that means I can't do the spontaneous coffee or dinner, but at least I'm ensuring that I have time set aside for my family and friends.

I've held side jobs for five years now, and over that time, I've come up with a few best practices that help me stay sane while managing the juggling act:

1. Stick to a schedule.
Sometimes I do feel like I've got too much going on, rushing from one job to the next. That's why it's important to set a schedule for the coming week — and stick to it. It helps me to avoid feeling overwhelmed. And if I can still manage to find time to cook dinner and spend time with loved ones, you can make it work too.

2. Remember that quality matters.
There's no point in working side jobs if you're putting your full-time job in jeopardy by letting your work quality suffer. So figure out if you're able to commit the time, energy, and organizational skills required to manage the extra work.

3. Be clear about your financial goals. If the motivation for getting a side job is about the income, then make sure you're clear on what money goal you're trying to reach — whether that's paying down debt, buying a home, or gunning for an early retirement.

Then ask yourself whether you really need a side job to reach those goals, or whether it's possible to fulfill them just as easily by reducing your expenses. You may not need to take on extra work if you can get to the same result by simply reexamining your budget.

Working three gigs — by choice — may seem a bit extreme to some folks, and admittedly, I do get concerned looks when people find out how much I work. But for me, it's worth the effort. Not only am I fulfilling my financial goals at a faster pace, but I'm also doing the things I love.

I enjoy the numbers-crunching I do at my pension job, and I love writing about money through my freelance work. Even my supermarket job has taught me interpersonal and time-management skills that I can apply to future endeavors. I always strive to improve and make the best of every day — and what I learn from juggling these jobs is part of that journey.

— Sean Cooper

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