Freelancing: It’s Not All Bon-Bons and Yoga Pants

In this week’s episode of the Financial Conversation podcast, we had our first guest, Catherine Alford. We were really excited to talk with her about a topic we all have a lot of experience with, the pros and cons of being a freelancer.

Cat is the coach and mentor that helped all four of us get started with our freelance businesses, so we thought it was fitting the she was our first guest on the show.

One of the common misconceptions about freelancing and working from home is that we do very little actual work. We’ve all had experiences where people have asked us how we can “make sooo much money” when all we do is “sit around in our yoga pants eating bon-bons on the couch”.

This is a misconception that we wanted to dispel, as well as sharing the good, the bad, and the ugly sides of working as a freelancer.

There's a good, bad, and ugly side to freelancing. None of us are perfect, and we sure as heck don't lead perfect lives. Here's our take on freelancing.

The Good

“I love the flexibility that freelancing provides in terms of how quickly I can grow my income. I’ve spent too many years wishing I earned more and could do more with my money so I’m very grateful that freelancing allows me to consistently improve my income while doing something that I love and truly enjoy.”


“There are a lot of good things about freelancing. Yes, I do get to work from home in my yoga pants and my commute is about 10 steps each way, but that doesn’t mean I don’t work. The biggest benefit I’ve seen from freelancing is being able to work without a set schedule. Some days I get up and start working at 7:30 or 8:00 a.m. but there are other days when I sleep in and end up working later into the evening. The flexibility of making my own schedule is the best part for me.”


“Freelance work has given me the ability to focus on both my career and my family. I am able to contribute to our debt pay-off while being home every day for our kids. I’m able to make money while also homeschooling, something that is very important to me. It’s the ultimately flexible job, which is exactly what I need. I’m able to structure my work, my hours, and my jobs around the the needs of my family.”


“Setting your own rates and not having to ask for permission to travel is extremely liberating. Before freelancing, I took one vacation the entire time I worked, and that was to visit my parents when they moved. I love that I can take my work with me wherever I want to go. Raises weren’t as easy to come by, either. With freelancing, you can either look for new clients with bigger budgets, or you can work on providing as much value as possible and making yourself worth more.”


The Bad

“The one major drawback from freelance work is that you don’t have any separation between work and home. Since I don’t have a job to go to outside the home, I am tempted to work all the time. Sometimes I feel like I’m in a never ending cycle of mom work and work work.”

– Kristi 


“This may not be necessarily bad if you can manage your time wisely and set limitations on how much work you should do, but with freelancing, if you don’t work you don’t get paid. There are no sick hours or paid vacation time off to take advantage of when you need it. If you spend the whole week in bed because you’re sick, you won’t have any income coming in later on as a result. It’s also a little difficult to stop working and checking emails if you take a vacation or would like a day off. It’s best to try to always stay at least one week ahead on your work in case anything unexpected happens and have a healthy emergency fund to rely on.”



“Having so much flexibility is a blessing and a curse. On one hand, you can work whenever, and on the other hand, you can seriously work whenever…and take it too far. It can be incredibly difficult to set a schedule for yourself when you’re the boss, and there are a lot of distractions to deal with. Whenever you’re not working, you’re technically losing money, and that’s a hard mindset to get out of.”


“I think the worst thing about working as a freelancer is having to pay for my own benefits and taxes. I know Kristi said in a recent episode that she was excited to have earned enough money to have to pay quarterly taxes, but it’s a hard day when I have to send away a big percentage of my income to the tax man. But those are just things you have to plan for when you set your rates as a freelancer.”


The Ugly

“I suppose the “ugly” part of freelancing is that there are days where I literally don’t get out of my pajamas until I get ready to go to bed again that night. I rarely wear makeup or do my hair and I’ve only worn “real” pants like 3 times since I quit my job to freelance full time last summer… Is that ugly enough? 🙂 On the flip side, the real ugly thing about freelancing is trying to convince potential clients of your worth. There are some people who are new to hiring freelancers that don’t understand the going rate for our services. They don’t understand that part of what they are paying for is the fact that we have to fund our own benefits and retirement accounts, and we have to pay our own taxes. These are clients that you want to avoid so you don’t end up working for pennies.”


“The ugly part of freelancing for me is not getting paid on-time. I send out invoices every month and rely on my clients to pay promptly. Unlike traditional jobs where you get paid a certain amount on a set date, freelance income can trickle in if some clients are slow with processing invoices, or worst case, you have to remind your client and constantly follow up with them to pay. While most of my clients pay on-time each month, one time I went weeks without payment from a client and consistently followed up with them as a result. Luckily, they finally paid, but moving forward I decided to enforce some type of contract to avoid situations like that. Having a specific contract and a healthy emergency fund will help smooth things out when it comes to receiving payment.”


“The ugly side of freelancing for me, is that I allow myself to take on too much. I have a hard time saying no to new projects or new clients and, as a result, I don’t get nearly enough sleep or exercise as I should. Especially since I do have my kids with me 24/7 (my 2 year old is sitting on my lap as I type this), it can be hard to get work done during regular hours. Late, late nights are a reality for me.”


“I’m with Kristi on this one. It’s so, so hard to say ‘no’ and prioritize yourself when you have clients depending on you. You want to do a great job and get paid, but that burden is on you. Unless you set boundaries, it’s very possible to get (or feel) taken advantage of. I’ve pulled more all-nighters due to deadlines then I care to admit, and the self-doubt you experience can be agonizing. When I started out, fear absolutely gripped me to the point of getting stuck in analysis paralysis mode – until I asked Cat for help. Freelancing and self-employment is not for the faint of heart. You have to want it more than anything to keep going and to make friends with failure.”


Bloopers From Episode 7

Okay, we have to have a little fun – we didn’t want to end the post on a sour note. Here’s proof freelancers know how to not take themselves so seriously all the time. 😉

Are you a freelancer? What do you think is the good, bad, and ugly of freelancing? Do you want to become a freelancer? Did you think it was completely different than the views we expressed? 

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