Is Upwork Really Undercutting your Freelance Income?

“Upwork is ruining the freelance economy.”

I see this argument a lot. It’s based on the idea that websites like Upwork (or Fiverr, Elance, Freelancer, Guru, whatever) are undercutting the freelance market, so much so that clients now think it’s acceptable to pay designers, writers, artists, and assistants a couple of dollars for a significant amount of work.

And looking through jobs on Upwork, it’s easy to see that many clients have ridiculous budget expectations – and they can because many people around the world are willing to work for these prices.

However, I’m not so sure that Upwork is really killing the freelance economy for those of us battling rents, insurance rates, student loans, and other western costs of living.

Rather, Upwork encourages people with small budgets to try their hand at entrepreneurship and building a business. A majority of the clients you find Upwork are people who would never before have ever thought of building a business, launching a website, maintaining a blog, or designing a logo before, simply because they were not able or willing to make the financial and time commitment to do so.

Once they heard you can get cheap labor online, they jumped at the opportunity – and are therefore unwilling to consider paying reasonable rates for high-quality work. Who can blame them?

Don’t despair. The clients that are willing to pay fair rates and understand the value of high-quality work, delivered on time, are still out there.

But they aren’t on Upwork. And you shouldn’t be either.

It’s time to stop blaming Upwork for driving rates down and start looking outside of Upwork for your income.

Do you have any freelance horror stories? Have you successfully found high-paying clients outside of Upwork? Share in the comments below!


Is Traveling with Debt Irresponsible?

I’ve been traveling for the last two years straight. Since I left Los Angeles in 2014, I haven’t had a true home base.

Instead, I’ve spent 8 months driving up and down New Zealand, 8 months house sitting in Hawaii, a month eating my way across Korea and Japan, 4 months exploring New York City and upstate New York, 10 days in coastal New England, 4 weeks eating all the barbecue in Austin, Texas, 1 week with family in Minnesota, 1 week back in LA, and now a five week return to Hawaii.

International travel, while an incredible experience, is no longer a unique event reserved for once or twice in a lifetime. Shit, traveling long-term is not even that rare anymore.

Twitter, Instagram, and blogs have me convinced that practically every other person is gallivanting around the world on trip with no end in sight.

Because I’ve traveled the last two years with nearly $50k in student loan debt, I assumed other long-term travelers were traveling with debt, too. At least the travelers in my 20-something age bracket.

Until I read a recent article in the New Yorker, Why I Quit My Job to Travel the World. The premise is not new. Still it’s a pretty funny jab at a lifestyle some of us choose to live.

I didn’t think much of it, until I read this response from Our Resume Gap, where they acknowledge their not-so-frugal spending habits while traveling.

The New Yorker piece suddenly took on a new meaning for me, with quotes like

“I couldn’t bear being chained to my desk in a stuffy office any longer. So I decided to quit and travel the world, bringing only my passport, a small backpack, and my enormous trust fund.”

“You don’t need to own a lot of “stuff” to be happy, especially when you can buy whatever you later realize that you need with your massive inheritance.”

Wait. Am I the only one traveling with a massive load of debt?!

I dug a little deeper in blogs, and asked around on Twitter. And it slowly dawned on me that most people who’ve decided to travel long-term are NOT in debt, and in fact might be pretty well-off financially (from either their own hard work or through the family they were born into).

No judgements (although maybe a bit of jealousy).

Still, this response struck a cord with me and ultimately led me to ask this question…

Is traveling with debt irresponsible?

I don’t have an answer, I can only speak from personal experience.

Do I feel irresponsible for choosing to travel, even with student loan debt? No, not even a little bit.

Here’s why: I pay 3x the amount of my monthly payments, EVERY SINGLE MONTH. Sometimes, I pay even more than that. I do use a credit card, but it’s mostly to get points for future airline tickets, and I pay my balance in full EVERY SINGLE MONTH.

Plus, it’s actually significantly cheaper for me to travel than it ever was to live in Los Angeles. I’ve paid more debt off in the last year, than I did in the three years I lived in LA. House sitting helps, a lot.

But that’s just my experience. I’ve made it a point to build up a business, pay off debts, and travel comfortably.

Is it irresponsible to do that with $32k left to pay? I don’t think so, but I can understand why many would think it is.

So here’s the deal. I really want to hear from you!

Are you traveling with debt? Did you hold off on travel until your debt was paid off?

Do you think it’s irresponsible to travel with debt? Let me know in the comments or on Twitter.


Ol’ Blue Betty: An Ode to My Ford Focus

Ol’ Blue and I have been together a long time – ever since my first car, a p.o.s. Pontiac nearly started on fire on the freeway in the middle of the night.

I’m not a car person, but I loved Ol’ Blue right away: bright blue, brand new (to me), and a zippy little thing.


At first, she merely took me to class and around Minneapolis and St. Paul.


But eventually, we explored further. Exploring the lakes, prairies, and tall trees of Minnesota.


Sometimes with cats in tow.


When wanderlust struck, Ol’ Blue was along for the ride (because she was the ride.


Our fondness for the West was undeniable, and we made the trip from Minnesota to California, and back more times than I remember (6? 7?).

Never hesitating to stop for photos along the way.


In times of need, Ol’ Blue was strong and sturdy…


And the perfect spot for a snack.


She was reliable in the unrelenting rain of northern California…


And the icy roads of the Rocky Mountains.


In the last nine years, I’ve spent hours in this car – leaving home, going home, starting new adventures, and driving away from places I grew to love.


As travels became international, Ol’ Blue was spending more time rusting out in the snow and salt of Minnesota winters. I knew it was time to let her go.

We had one last hurrah together this winter, traveling from Minnesota to the east coast. I thought the roads around New York City were going to break an axle, but Ol’ Blue made it through. We drove from NYC to Boston to Maine and back again.

Not ready to say goodbye, we took the long way back home (by way of Austin, Texas).

Ol’ Blue returned back to Minnesota in June, where she now has a new owner – my adventurous little sister.

Although I didn’t sell Ol’ Blue for much, I was able to pay off one student loan with the money. Truly the car that kept on giving.

Nine years and 120,000 miles later, I’ve seen so much of America, finding a bit of myself in every place I’ve been. And it’s all because of you, Ol’ Blue.

Heather and Baracus House Sitting

My House Sitting Story

I get asked a lot how I’ve been able to travel AND continue to pay off my student loan debt. Obviously I don’t have a big blog following, and I’m certainly not receiving any free or even discounted hotel rooms (unless you count my AAA discount).

So what’s my secret? Two words: House Sitting.

After ten successful house sits, my partner and I were recently asked by to share our story.


Our House Sitting Story

We first discovered house sitting in 2014. At the time, we were living in Los Angeles, working full-time jobs with long commutes. Both in our twenties, we enjoyed our jobs but were struggling with the idea that a cubicle and a commute would be our lives for the next forty years.

We both enjoyed traveling and got out of the city for a few days here and there when we could, but we were ready to take a longer trip abroad. So in September 2014, we did just that with one-way flight from Los Angeles to Auckland, New Zealand on a one year visa.

Once we discovered house sitting, it seemed like the perfect fit for us! We had both grown up with cats and dogs, and we truly missed having them in our lives while we were living in Los Angeles.

Heather and Baracus House Sitting

Making connections and new friends

Since our first house sit in 2014, we’ve been hooked. Through TrustedHousesitters, we found a young couple based in New Zealand who were looking for someone to watch after their two rescue pit bulls. They had previously boarded the dogs in kennels on shorter trips, but neither dogs did very well. In fact, one would become so anxious that he could hardly eat, and they both missed out on long daily walks.

After an initial Skype conversation and several emails with the home owners, we all felt confident that this was the right fit. And now, two years later, we consider the home owners good friends who we look forward to meeting again soon – especially the two wonderful dogs!

Since then, we’ve had wonderful experiences house sitting back in the United States – from Hawaii to New York to Texas. We tend to prefer longer-term house sits, as it allows us the chance to really get to know an animal (or animals!) and develop a relationship with the home owners during our stay.

Pretending to be Austinites for the next couple of weeks. Who knew Texas was so green?!

A photo posted by HeatherLois (@ecoheather) on

A career without a cubicle

So much of our jobs back in Los Angeles had us in front of a computer, and we realized we could do much of the same work as long as we had a reliable internet connection. Tae works in online marketing and advertising, and Heather provides communication support for nonprofits and mission-driven businesses.

Because we work remotely and on our own schedule, we’re able to spend most of our time on house sits on property, providing lots of love and attentions to pets. They become our “office-mates” so it’s really a win-win situation for all.

House sitting is such a great fit for us right now! It allows us to experience a new place for several weeks at a time, meet interesting and like-minded people, work full-time on our own schedule, and spend time getting to know and playing with sweet pets. Plus, we love that we can give home owners the peace of mind that their pets and home are well-taken care of while they are away enjoy their holiday.


This post originally appeared on If you’re interested in trying house sitting yourself, use this link to receive a discount on your membership.

Tax Time

It’s been quiet over here on LifeWithDebt lately. But for good reason. My freelance side gig has now become my full-time business – and most of my time at a computer has been spent focusing on my incredible clients.

After a bit of soul searching, I shifted focus from providing freelancing writing services, to committing fully to helping nonprofits and purpose-driven organizations advance their missions and do more good. It’s an exciting shift, and one that dives deeper into my commitment to social and environmental justice.

Aaaaand, it’s tax time. And I’ve been avoiding filing like it’s the plague. This is the first year I’ve filed my own taxes (shout out to Mom for helping me out over the last 8 years!), and 2015 was the first year where I made sizable income from self-employment. Meaning I hadn’t paid taxes all year. And the thought of filing has been causing me stress basically since January 1.

But on this rainy, yucky New York day, I was determined not to leave my desk until these bad boys were filed.

And, actually, it was surprisingly simple. Unbelievably simple.

If you’re still procrastinating, check out H&R Block’s online filing program. It’s free, you can do it all online, and the system walks you through every step.

Nobody’s paying me to say that – although hit me up H&R Block if you need a rep! – I just really can’t believe how easy they made this process.

Now to start filing my quarterly taxes…

Do you have any tips to make tax time a little easier? Any secrets to get your maximum refund? I’d love to hear your thoughts in the comments!

5 Lessons Hawaii Taught Me About Personal Finance

Since April, I’ve been living on the Big Island of Hawaii, enjoying new and exotic tropical fruits (soursop is my new favorite!), dreaming of whales off in the distance, and exploring the peaks and valleys of this incredible island.

But my time in Hawaii wasn’t all about play; Hawaii was a chance for me to up my professional game.

Over the last eight months, I’ve found a core group of entrepreneurs, start-ups, and nonprofits that I love working with every day. I’ve finally started to put money back in my savings account. And I’ve made huge progress on my student loans.

The slower pace of island living (plus ample excuses to spend time outside and away from work) offered a chance to reflect on goals, dreams, and what I want daily out of life. The five biggest takeaways?

Live Aloha

A photo posted by HeatherLois (@ecoheather) on

Aloha is more than a greeting in Hawaii, and I won’t pretend that I know all of its meanings, but to me it came to symbolize a warm welcome and a feeling of gratitude.

I’ve been fortunate to work with interesting, friendly, and fair clients. Every day, I appreciate their dedication to their work and their trust in me to help move projects forward.

Since I work remotely, I prioritize responsiveness and clear communication; but I also want to share a warm feeling of respect, positivity, and warmth – my own brand of aloha.

I believe building client relationships through the spirit of aloha will help me work with the best clients out there while building a sustainable business.  

The Best Things in Life are Free

A photo posted by HeatherLois (@ecoheather) on

The sun rising over the Pacific. Sleeping in the day after a big hike. A glimpse of a whale spout in the distance. Fresh, hand-picked fruit. A technicolor rainbow after an afternoon rainshower. The sun setting behind Maui in the distance.

It’s been said so many times that it’s easy to ignore, but Hawaii was the perfect reminder:

The best things in life really are free – but you’ll miss them if you’re not paying attention.

And, honestly, if you can’t find moments of happiness, every day, wherever you are, than you won’t find it by spending thousands of dollars on a plane ticket or a night at a private resort.

Don’t Be Afraid to Splurge a Little

A photo posted by HeatherLois (@ecoheather) on

Likewise, you’ll miss out on life if you’re too concerned with saving every penny and striving for absolute frugality.

Buy the plane ticket. Unwind at the private resort for a day or two. Splurge on the dress that makes you feel like the bosslady that you are.

(AirBnB and Google Flights are my go-to to save on accommodation and travel.)

Even Paradise Can Be a Struggle

A photo posted by HeatherLois (@ecoheather) on

Forget about the Hawaii of your dreams for just a moment.

Instead imagine a hot, humid jungle (or desert, depending on what side of the island you’re on) crawling with giant cockroaches, rats, mongooses, huge centipedes, and loud tourists.

While produce is ubiquitous, other staples like bread and milk will cost 2 to 3x more than what you may be used to. Rent and utilities are some of the highest in the nation, and petty theft and homelessness are real, apparent problems in any town.

Remote work feels a bit like Hawaii at times. It sounds like paradise at first – work whenever you want, from wherever you want! But the reality is a bit more complicated.

Taxes, time zones, and finding clients can be huge headaches (to name just a few).

In both remote work and living in Hawaii, if you come expecting only paradise, you’ll likely soon be high-tailing it back home and back to a desk job. But, if you approach both with a practical sense of reality (and a cushion for unexpected surprises), you’ll never look back.

It’s All About the Hustle

A photo posted by HeatherLois (@ecoheather) on

Finally, even in paradise, the hustle can’t stop. Palm trees and ocean breezes are all well and good, but these views aren’t paying off my students loans.

The Most Expensive Present I’ll Buy for Christmas This Year

Merry Christmas to MeOh Christmas tree, oh Christmas tree…

Since quitting my full-time office job in September 2014, I’ve been location independent. First traveling throughout New Zealand, then to Hawaii, over to Korea and Japan, and now back on the Big Island. Prudence allowed me to travel comfortably off of my savings for eight months. And for the last seven I’ve steadily been building up my remote business.

Needless to say, there’s not a whole lot of money in the bank for extravagant Christmas presents this year. Family and friends, I’m serious when I saw ya’ll are getting socks. Every one of you.

But, I’ll admit. This year, I was selfish because the most expensive Christmas present I bought this year was for … me.

This Christmas, I paid off $1,600 in student loans for the month of December.

Alright, it’s not as cool as a personal holiday greeting from Brian McKnight.

And $1500 in a month may not sound like a big deal to everybody, but this is huge for me. This is the most money I’ve put towards my student loan at one time.

And this is truly the gift that keeps on giving.

This $1500 is a step towards financial independence.

This $1500 is a major confidence boost.

This $1500 is evidence that I’m capable of building up a successful business on my own.

This $1500 is proof that quitting my job and traveling the world wasn’t a financially ruinous decision.

This $1500 reminds me that my life is damn amazing and each day can be just as good as the last.

What is the most expensive gift you bought this year?
What did you get yourself?
Let me know in the comments!

Merry Christmas and Happy Holidays.
Here’s a little Brian McKnight on me.

Understand Your Student Loans

Since the moment I took out student loans, I’ve obsessively watched Sallie Mae (and now Navient), watching the numbers double with each new loan. Even when I graduated, every month I watched the dollars slowly add up as I put off making payments.

At any moment, I knew exactly how much debt I owed. And it was a lot. $54,000 upon graduation in 2011.

Yet, shockingly, most Americans have no idea how much debt they have.

On average, individuals estimate their student loan debt to be 25% LESS than it actually is. If you’re guessing your debt load is $20,000, it may actually be closer to $26,000.

Even if you’re starting with absolutely no understanding of your student loan debt, you can dig yourself out that financial black hole.

Baby steps.

Acknowledge Your Debt

Listen, thinking about how much debt you’re in can be totally overwhelming. Several times I’ve calculated how long I’ll have to pay minimum payments and ended up curled up in bed with a strong drink.

I’d like to think I’m mildly more attractive than any of the Baldwin brothers.
That fear isn’t getting you anywhere (except deeper in debt). Acknowledging your debt is the first step to paying it all off.

Tools to Help You Understand Your Student Loan Debt

Before you practically begin to make pay your loans and make dramatic financial changes, take a moment to understand your student loan debt and your spending habits.

Play around with numbers.
When it comes to student loans, or any debt, the best way to understand its impact on your life is grasping just how long it will take you pay it off.

If you have public loans, check out the Federal Student Aid Repayment Calculator.

For private loans, try out PowerPay, a debt paydown calculator that allows you to create a plan to pay off your student loans. This is a great tool to understand how crushing interest can be over time.

If you’re not ready to test out the above calculators, give this one a try first.

Track how you spend your money.
I use Mint to monitor my spending and bill payments. Mint connects to your bank account and credit cards, so you never need to remember to track every purchase.

You may also want to try You Need a Budget (YNAB).

Consider Your Lifestyle

Some blogs will urge you to live as frugally as possible while you pay off your debt. And you should But honestly, you’re the only person who can make the decision of what frugal means for you.

Personally, I’ve dramatically cut down on certain living expenses (like rent and car payments), but absolutely refuse to give up my morning coffee.

Or my afternoon coffee.

Or a Saturday morning croissant at my favorite bakery in town.

No amount of debt will take this away from me.
“Personal finance” is personal for a reason. And what financial independence means for you likely means something completely different for me. And it will change, based on your income, expenses, lifestyle, and goals.

Personal Finance is Personal
Your ideal lifestyle will dictate what personal finance means to you.

Why It Took Me 4 years to Pay off 11k in Student Loan Debt

If you’re like me, this is your new least favorite website:

Navient Student Loan Debt Site

I graduated from a public university in December 2011 with $54,000 in student loan debt. Which, admittedly, is twice as much as the national average of $27,000 for 2011. (What I wouldn’t do for only $27,000 in debt…)

Since December 2011, I’ve dutifully paid student loan payments every month (well almost…see below) for sixty months. And what do I have to show for it?

A still gigantic, although slightly less panic-inducing, debt of $42,500.

If I’m being honest with myself, I’m actually fairly impressed. 22-year old me couldn’t fathom even making a dent on that loan, let alone cutting it down by 20%.

But I can’t help but ask – how have I only paid off $11,000 when it feels like I’m constantly throwing money at the damn thing?

Well, there’s a few reasons.

Six Month Grace Period

Like many , I took advantage of the six months of grace that many loan institutions (looking at you Sallie Mae) allow after graduation.

Unfortunately, the interest fees don’t stop. Not paying anything on my loans for six months cost me at least $1200.

Calculate your daily interest rate.

Another Six Months of Forbearance

Six months after graduation, I still wasn’t making enough to comfortably make minimum payments on my loans. Serves me right for getting a degree in outdoor education.

Looking to delay payments further, I put loans in forbearance for another six months.

Forbearance, life deferment, is a way of temporarily postponing loan payments. If you’re unable to make regular payments, student loan forbearance can help you avoid delinquency and default.

Making Only the Minimal Payments

Once I entered the world of full-time, regular, office work I immediately took control of my student loan debt and took the loans out of forbearance.

Unfortunately, I only make the minimum payments for two years. After two years I made a startling discovery…

Only Half of My Payments Went to Student Loan Debt

Each month, I dutifully tracked how much student loan debt was left to go. And each month, I couldn’t figure out why my debt wasn’t declining by the hundreds of dollars I would putting towards it.

And then I sat down and actually looked at the numbers.

Each month, interest on my loans was costing me $200. My minimal payment was $400.

By making minimal payments, half of my payments were paying for interest – accumulated just over the last 30 days!


Time to Get Serious about my Student Loan Debt

After the initial shock and subsequent mild depression, I determined to get serious about paying these bad boys off, starting by paying more than the minimal payment each month.

About this time, I was also serious about finding an alternative to the 9-5 desk job. When I quit my office job in 2014, I wasn’t going to let my loans sit on the back burner again, collecting even more interest and haunting me every day.

Instead, I determined to pay all of the debt within 10 years while enjoying the fantastic, wonderful thing we call life.

And thus, Life… with Debt was born.