How I Built a Freelance Portfolio Career


It’s been almost four years since I quit my “dream” HR manager job. Turns out, it wasn’t my dream after all. And I was miserable. I’ve shared this story in detail in my column on The Muse (you can read all about it here) but that’s not what this blog is about.

Since walking away from the career I’d spent nearly a decade building, I’ve created something totally new. And it doesn’t look at all how I thought it would. Maybe that’s because I’ve been piecing it together, like a puzzle. Only I have no idea what the finished product will look like. I’m kind of winging it over here.

Which I kind of love.


I always laugh when people ask me what I do because it’s hard to explain. Why? Because at any given moment, I have about five different jobs. Without even meaning to, I’ve built a portfolio career. Which basically means that I’m a freelancer juggling multiple contract gigs that span a variety of industries and responsibilities. Like a Jac(lyn) of all trades!

Read on for a peek inside my career portfolio, and the inside scoop on how I landed each gig.

Career Advice Columnist

I used my HR and recruiting experience to pitch an article to The Muse, which led to my own career advice column! It’s such a fun way to leverage my expertise to help others, and the editors there are amazing. Their feedback has helped me to improve my writing skills and build up my confidence. I’ll write for them forever if they’ll let me!

Writing for The Muse also led to tons of other opportunities. I’ve gotten to write for Jobscan, FairyGodBoss, Maven Recruiting Group, and more because their editors read one of my Muse articles. So cool right? I’ve also been syndicated on Forbes, Business Insider, Mashable, Fast Company, and USA Today.


I owe this one to The Muse, too. I’ve been hired to ghostwrite thought pieces for HR executives, an employer branding guide for a well-known consulting firm, and a career advice guide for a huge corporation (coming soon – and I can share this one!).

Freelance Writer

While I love sharing career advice, I’ve been working on expanding my portfolio to include more of my interests. I’ve picked up writing gigs with The Bold Italic, Arrivedo, and a well-known boating company (coming soon!) by pitching travel, lifestyle and boating topics to some of my favorite publications. This is easily my least stable source of income, but it’s also the most fun.

Real Estate Marketing Assistant

I found this job on Craigslist, of all places! I help a local realtor with her marketing needs (blog, social media, newsletters, listing flyers, websites, etc.) and basic administrative stuff (data entry, scheduling inspections, coordinating with photographers, etc.). It’s a fun way for me to use my creative skills and get a break from straight up writing. It also gives me an excuse to get out into the world! I usually stop by the office to check in once a week.

The number one thing that helped me land this job was my writing and social media experience. Lucky for me, this realtor was able to look past my lack of industry expertise. And in case you were wondering, she was super supportive of me moving onto the boat 😊

Personal Assistant to an Animal Rights Activist

Another Craigslist find! The founder of a local animal rescue organization (and all around amazing person) was looking for someone to assist him with a variety of random tasks, ranging from picking up his mail to tracking down celebrity contact information. So, I sent him my resume and a little blurb about myself, and I got the job! It probably helped that I live a plant-based lifestyle and am the proud mom of a rescue dog.

It feels so good to know that I’m contributing to a cause I care so strongly about – even if that just means picking up some dry-cleaning or creating a spreadsheet to track every kind of plant-based meat on the market. Plus, I love the variety – I never know what he’ll need help with next!

I’ve also tried out…

Resume Writing

A few months after I quit my HR job, I started a small resume writing business called The Job Hop. I was suddenly so busy that I was able to build out a really pretty website (, expand my service offering, and hire a couple of freelancers! This was my primary job for more than two years, but eventually, I realized that I really wanted to focus more on my writing career. So, I sold the business.

Dog Sitting & Dog Walking

After I sold The Job Hop, I wasn’t sure how I’d make up for the decrease in my monthly income. So, I picked up a few clients on Rover. It was a great experience, but I found being away from Brian and Indy overnight to be really hard (I also got really attached to the dogs, and would cry when I had to say goodbye). And sticking to a rigid dog walking schedule just wasn’t for me.

Freelance Recruiting

At first, I thought the reason I was so unhappy with HR was the lack of flexibility. So, I picked up a part-time recruiting contract with a local agency. The team was amazing, but at the end of my contract, I knew that I just didn’t love recruiting like I used to. So, I started blogging for them instead!

Virtual Styling

The very first contract gig I picked up after quitting my HR job was with Stich Fix. They hire virtual personal stylists to put all of their beautiful “fixes” together. It was a really fun and kept me from turning into a totally unproductive, deeply depressed blob. I had no idea what I really wanted to do, so this was the perfect holdover. But, after a few months, I got a little bored. So, I started looking for something with a more variety. Looking back, I’ve certainly achieved that!


So, that’s my career portfolio. I admit it’s been a little all over the place. But I’ve learned a lot, and every piece of this mysterious puzzle is bringing me closer to my ultimate goal: to write! And travel. Maybe write while I travel?

I also have a few short stories and a novel in the works. In a perfect world, that’s all I’d do. But for now, I’m grateful for the income and flexibility that my portfolio career provides. Plus, I get to work from the boat!

Jaclyn Westlake