by Hilary Oliver

The Ups and Downs of Freelancing as a Couple

Freelancing can be a cycle of feast and famine. So what happens when two freelancers live under one roof? This is one couple’s story.
Rowing Hero

It was a low moment. Brendan and I swept someone else’s crumbs off a table in the cafeteria area of a grocery store in Bend, Oregon, and opened our laptops. As I scrolled through the email from my accountant, the falafel balls I was chewing began to seem extremely dry—and overpriced. I knew the growing pit in my stomach would not be going anywhere until I opened up and told Brendan: I didn’t have enough money in my account to pay my taxes.

Facing the Reality of Freelancing Living

A little over a year into my full-time freelance writing career, traveling and living out of a van with my boyfriend, I felt like things were generally moving in a good direction, if slowly. I was selling stories regularly, though they only paid $100 here, maybe $150 there. Thankfully I had an ongoing gig that helped me pay my bills each month—but only barely.

My boyfriend, Brendan, had been freelancing for a couple of years already, living out of a built-out van, traveling around the western U.S. He’d built up his freelance writing business in his spare time over the course of a couple of years before quitting his day job and hitting the road.

I think lots of people following Brendan on social media probably thought he had rich parents or something that allowed him to keep traveling, but he’d actually just worked really hard to build up his career and then chosen to live simply in exchange for the freedom of the traveling freelance life.

He was a rare exception to the statement one of his grad school professors had made: “To start a successful freelance writing career, you either need to be independently wealthy or have a very understanding spouse.”

Brendan hadn’t had either—but now, as much as I wanted to be independent and avoid traditional gender roles, I was beginning to understand the part about needing an understanding spouse.

Canyon Pair

When you work for yourself and don’t have a boss to take taxes out of your paychecks before you even receive them, you have to put money aside yourself. Unless you want to find yourself in my shoes, living month-to-month and faced with a large tax bill and no money in the bank to pay it.

Monthly payments on the massive mound of credit card debt I’d accrued in my late 20’s gobbled away my small paychecks instantaneously. Not to mention costs like the $120 monthly cellphone bill to pay for my mobile wireless hotspot—in case wherever we needed to work for the day didn’t offer Wi-Fi. As hard as I was working, I still wasn’t bringing in enough—or saving enough—for all my expenses plus quarterly estimated tax payments.

A Vulnerable Moment

I barely breathed while I waited for Brendan to wrap up whatever it was he was typing across the sticky table. I had never been in a relationship like this before, where my significant other was more financially stable than I was and actually spurred me on to be more responsible myself. I’d also never wanted so badly for a relationship to work out the way I wanted this one to work out—I didn’t want to take advantage of Brendan; I wanted to be an equal partner, to be a support for him the way he was for me. I worried he’d be disappointed, maybe angry. But I also knew I had no other choice but to be transparent about my shortcomings. Financially, we’d have to figure out a way to move forward, and emotionally, we’d have to do the same.

Peak Pair

He was crestfallen when I explained. But not angry. He graciously paid my tax bill, and I burned with a fresh motivation to earn more, and manage my finances more responsibly. The thing is, jumping into freelance life 100% can be risky. I could have waited longer to quit my day job until I had more savings in the bank—or any, for that matter. But we’d made the jump together, me moving into the van with Brendan and giving up the stability of my previous job. It had been more of an emotional decision than one carefully planned and prepared for. And while I wanted deeply to be able to pull my own weight financially, I knew if I was going to get there, I needed to accept this moment with grace and humility, and then work hard to get to a point where I could, ideally, return the favor.

“It’s OK—I’ve got it.”

Two years later, Brendan and I are standing at a grocery store checkout stand, the lady behind the register swiping about two days’ worth of peanut butter, eggs, fruit, greens, and fizzy water. We both pull out our wallets, Brendan asking, “Should we split it?”, and me saying, “It’s OK—I’ve got it.”

It’s been a couple of years of hard work: pitching more work than I can handle and then stressing out about completing it when I get the jobs, asking for raises, completing bigger and bigger projects for bigger and bigger clients. And I just paid my second estimated tax payment for the year, without completely emptying my checking account. Which feels—amazing.

Brendan gave me a huge gift by letting me move into the van with him to save money during those early freelance days, buoying me through that first year or two while I tried to learn to swim in the freelance world. No, picking up a couple of grocery bills won’t exactly cover it, if we were keeping tabs. But this year he’s taking his own professional risks, touring to promote his new book, and I’m happy to finally be in a place where he doesn’t have to worry about me. Where maybe I can be the one to pay for our next vacation.

Finances might be one of the toughest things for couples to learn how to handle together—and when both parties are self-employed, things get even more complex. Income can be, as we say, jagged. Sometimes your mailbox is full of checks, and sometimes it feels like months go by when your bank account is simply draining. Sometimes one of you is feeling rich while the other one is scraping by between paychecks.

Managing Money with Humility and Honesty

For me, partnering with another freelancer has been a lesson in humility and honesty. It’s pushed us to be more vulnerable and compassionate with each other. I’m still working hard and fantasizing about the day when I can feel like the sugar mama in the relationship, but for now I’m simply thankful that all our ups and downs as freelancers have brought us closer together instead of tearing us apart.

For more tips on managing money with your partner, check out the Relationships + Money section of our blog.

Hilary Oliver is an outdoor adventure writer, editor, and filmmaker based in Denver. Her work has appeared in Adventure Journal, Climbing, Sidetracked, National Geographic Adventure, and many other websites and magazines. You can see more of her work at

Cycling Pair

Disclaimer: Hey! Welcome to our disclaimer. Here’s what you need to know to safely consume this blog post: We do our best to make sure information is accurate as of the date of publication, but things do change quickly sometimes. Any outbound links in this post will take you away from, to external sites in the wilds of the internet; neither Simple nor our partner bank, BBVA USA, endorse any linked-to websites; and we didn’t pay/barter with/bribe anyone to appear in this post. Individual situations will differ; consult your favorite finance, tax or legal professional for specific advice. And as much as we wish we could control the cost of things, any prices in this article are just estimates. Actual prices are up to retailers, manufacturers, and other people who’ve been granted magical powers over digits and dollar signs.

Important! This account is for your personal use only

An increasing number of customers are being targeted by fraud scams. Before you apply, review these guidelines to help prevent you from being involved in fraudulent activity.

Do not open an account on behalf of someone else
If anyone asks you to open a Simple Account to receive funds, it is an attempt at fraud. Common fraud attempts include requesting that you open an account to receive a gift or bonus offer, obtain a job or job training, or help someone else receive funds (such as unemployment benefits).

Do not share your login or account information with anyone
Neither Simple nor any other legitimate institution will ever ask for your account information. If any third party requests your Simple Account login information, it is an attempt at fraud. Sharing your account information with another person or allowing someone else to use your account to receive funds is a violation of the Simple Deposit Account Agreement terms and conditions and can expose you to fraud.

Actions we may take if fraud is suspected

We take fraud and security very seriously at Simple, and take rapid action in the instance of suspected fraud attempts.

We may freeze and close accounts
We may freeze and close accounts if fraudulent activity is suspected, including the following circumstances:

We will report fraud attempts
We are responsible for reporting fraud attempts to authorities, including attempted unemployment fraud. There are state and federal penalties for unemployment insurance fraud (including potential fines and incarceration). If you suspect you are a victim of unemployment fraud, contact the appropriate state fraud hotline listed here.

I acknowledge that I have read this notice Continue Application