Why I freelance: Designing a lifestyle-based business

A few months ago, I was at a retreat for women when one attendee, a fellow freelance writer, mentioned that she puts her values above any income goals. In the past, she was earning a six-figure income as a freelancer. Now, she lives in a rural part of the Northwest, where the low cost of living allows her to earn enough to sustain her lifestyle by writing just one article a day. “When my freelance work gets in the way of getting involved in local politics, that’s when I get annoyed,” she explained.

There are a handful of reasons one might choose to freelance rather than work for an employer. For some, it's the ability to earn more. For others, such as my colleague and myself, it's the ability to live in step with your values and maintain control over your own lifestyle—a concept that can seem as distant as it is appealing if you work 9 to 5.

Here’s how freelancing has enabled me to create a lifestyle based on what’s most important to me:

I have the freedom to work anywhere

In the four years I’ve been a full-time freelance writer, I’ve spent summers dog-sitting in Chicago, and accompanied my partner on some commissioned art projects. We’ve trekked across the country to Marfa,Texas; Santa Fe, New Mexico; and New Orleans, Louisiana. I’ve worked on assignments in hotel rooms, and even attempted to type away with a laptop balanced on my knees while en route to our next destination.

There have also been a number of workcations — while in Hawaii with my family and during weekend “work getaways.” Some vacations I’ve managed to work for a few hours in the morning and “turn off” work mode the rest of the day.

While these aren’t ideal getaways, as I would much rather just leave the laptop at home and not work, the fact that I can still earn income while traveling has allowed me greater flexibility to see more of the world. (I do take real time off as well — last year I took about six weeks off in addition to these workcations.)

I have more time to volunteer

Volunteering has long been a big part of my life. When I was a depressed teenager, community service was a way for me to overcome mental and emotional struggles. It helped me learn to work with others, develop empathy, and connect and engage with people from all walks of life.

The last few years, I’ve been able to devote a weekday morning to volunteer with my mom at a local food pantry. It’s a way for us to bond and stay involved in one another’s lives. And after moving to a cabin in a canyon about 20 miles east of Los Angeles about a year ago, I volunteer at a botanical garden. As a newcomer to the area, I’ve met some amazing, community-minded folks who share a love of nature. What’s more, it’s been a welcome respite from spending long hours alone, working.

I don’t want to wait until I’m retired to have time to volunteer, or take a sabbatical to fit in my other interests. Because I can design my own schedule, I can squeeze volunteering into my weekly routine.

I enjoy a flexible schedule

Greater flexibility has long been touted as a freelance perk, and I try to take full advantage. I relish having the luxury of running errands in the middle of the day, and heading to water aerobics class in the mornings. After all, it makes up for the downsides of being a solopreneur (feast and famine cycles, paying for your own health insurance, and budgeting on variable income — to name a few).

I have the opportunity to develop my career goals

Long before I was a personal finance writer, I wrote fiction. My time outside of my day job was spent working on my short stories and flash pieces. I labored over craft and syntax. And when I decided to transition to full-time freelancing about five years ago, I set aside time every morning to write fiction.

Fast forward to the future, and while my ambitions have changed, I still devote time to developing my career. In the past year I realized I wanted to pivot, so I’ve enrolled to become an AFCPE® accredited financial counselor.

My hope is to help artists and freelancing creatives to be more financially savvy and help them build their businesses. I’ve also enrolled in a community counselor course to improve my people skills, particularly with underserved populations in Los Angeles. At the same time, I’m working on the first installment of a series of books designed to help freelancers. I’ve also been putting on more workshops, and spoken as a panelist at conferences and talks for freelance writers.

If I had a day job, it would be much harder for me to carve out time to devote to these professional goals.

I have the option to say “no” to work

Every year I set a reasonable income goal. And once I hit this number, I go into “work optional” mode. That means that I can hold on taking on new clients, or say “no” to assignments that I don’t want to take. The great news is that ever since I became a solopreneur, I’ve hit this goal earlier each year. And while I’ve bumped up the amount on average, I can still usually hit it with a few months remaining in the year.

My partner says that I would probably be severely unhappy and bored if I didn’t have work to keep me occupied. So while I am in “work optional” mode, I don’t turn completely off. However, when I do want to scale back on client work, I’m fortunate to be in a place where I can without taking a financial hit.

My struggle remains

There are times when these values fall to the wayside.

As freelancers we’re prone to “feast and famine” cycles, where we toggle between periods where we’re getting tons of work with lulls where jobs are scarce. When I’m in the trenches of a “famine” period, I forget why I decided to freelance in the first place. I take on as much client work as I can, I get entrenched with deadlines, and my self-care goes out the door. And although all this work causes my income to steadily climb, my overall sense of wellness depletes if I’m not spending my time and energy on what I care about the most.

When I transitioned from full-time employee to freelancer, I thought that my greatest challenge would be earning a decent living. It wasn’t; the most difficult part of being a freelancer is that I’m responsible for making more decisions, day in and day out. It’s ultimately up to me whether I want to take on more work and what I want that work to be. For better or worse, I’m the master of my own destiny.

To combat this, I’ve created a spectrum. On one end are things I ultimately want to do more of, both professionally and personally. On the other end are things that I want to do less of.

And when tasked with a decision, I refer to my personal spectrum. I ask myself if each choice is helping me move toward my long-term goals, and whether it’s aligned with my values. I consult with my tribe (members of my freelance writers mastermind group and a cohort of trusted friends who know me well). I also refer to a basic checklist of questions that I ask myself. As I deliberate over these decisions, I also reflect on where I am devoting most of my energy, and how that energy might be better spent.

While at times designing a lifestyle-based business feels more aspirational than a reality, in the past year I’ve made a more concerted effort to bring my day-to-day schedule in sync with my values and my natural ways of being.

It’s taken a combination of tactics: achieving greater self-care, staying focused on my priorities, and making decisions that best suit my interests, values, and long-term goals. While it’s been a process of constant recalibration, the freedom I exert over my life as a freelancer has made it possible for me to keep experimenting and finding new ways to build the life I want.


Jackie Lam
Jackie Lam is an L.A.-based money writer whose work has appeared in Forbes, Business Insider, and GOOD Magazine. She is currently studying to be a financial coach (AFC®) to help artists and freelancers with their money. In her free time she blogs at heyfreelancer.com.

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