110 Money Stories, Vol. 1: The Three Questions You Must Ask Before Starting A Side Hustle
From a financial educator who has had many of them herself
Hi, my friend!
I interviewed more than 110 people in writing my book, “Ask Questions, Save Money, Make More: How To Take Control Of Your Financial Life.” To keep the book from being about 700 pages long, an enormous amount of useful information and many interesting stories simply had to end up on the cutting-room floor, unseen. Until now.
This is the first in a series called 110 Money Stories, in which I’ll share some of the best stuff that didn’t quite make it into the book. The series will include a diverse group of voices and touch on a wide variety of topics, but it will always live up to the promise I made to you with this newsletter: Every story will have some takeaway that you can use and apply to your own financial life.
Enjoy!
Side hustles are an absolute necessity for millions of Americans today. About 4 in 10 Americans say they have one, and most of those who do say they couldn’t get by financially without it.
Vee Weir knows that feeling well. Today, she’s an award-winning financial educator with more than 40,000 social media followers and a self-described “anti-capitalist finance activist.” She’s even been featured in Forbes, Business Insider and CNBC. However, in wrestling with debt over the years, as so many of us have, she’s taken on many side hustles, including dog-sitting for wealthy pet owners in her area.
Those experiences have given her a clear picture of what it takes to start and maintain a successful side hustle. That’s a big deal because, despite what social media influencers and online course sellers might tell you, side hustles aren’t easy money. Sure, you might be able to bring in a few dollars here and there with minimal effort, but if you’re looking for sustained income that is actually going to make a difference to your finances, you need a plan. Even with one, there’s no guarantee that your side hustle will take off immediately – or ever – but without one, chances are that your dreams of that extra income won’t ever become reality.
Here are what Weir described as the three main questions you must ask before starting your side hustle…
1. What are you good at and able to monetize easily?
“We're not trying to start a side hustle that you have to get a two-year degree for, you know,” Weir said. “That's going in the negative direction. So what are you good at already?”
For Weir, it was all about handling animals.
“I grew up with animals,” she said. “I worked on farms. When it comes to animals, I am very comfortable and skilled and knowledgeable. So I knew that that was something that I could monetize.”
It wasn’t just her experience with animals that made her confident, though. She also took the time to do some market research to get a deeper understanding of her potential customers. When she did, she liked what she found.
“I knew that dog-sitting in this area would be very profitable because there are a lot of dogs per capita,” Weir said. “People here are very wealthy, and they really care about their animals, so it was a no-brainer.”
She also knew that she wouldn’t have to look far to find those potential customers. To get her dog-sitting hustle off the ground, she signed up with Rover.com, a site that connects pet owners with sitters and walkers near them. The hustle took off from there.
Photo courtesy of Vee Weir
2. How much money do you want to make?
Is this really a question? You want as much money as you can get, right?
Of course, in an ideal world, you’d make as much money as you wanted. However, as 2025 has proved at seemingly every turn, we do not live in an ideal world. Money’s not growing on trees waiting to be picked. It takes time, effort, planning, sweat and more, and with a side hustle, the amount of all of things that you’re willing to expend is likely directly proportional to how much money you need to make with it. In other words, the more money you need to make, the more work you’re going to be willing to put in.
Weir wasn’t looking to get rich with her side hustle. She just wanted a little extra financial wiggle room as she started her business. “When I decided to start my own business, I needed to supplement my income,” Weir said. “I know social media makes it seem like everybody's successful when they start their business, but it's slow growth. It's a slow burn in most cases.”
Weir said her goal at the outset was $1,000 to $1,500 per month. That’s a big goal, to be sure, but one that she felt was attainable through dog-sitting. Had her need been greater, her plan might’ve looked different.
3. Do you have the mental capacity for a side hustle?
Side hustles can be a grind. Even if you’re doing something that you love and sounds like fun such as dog-sitting, it is real work – and work done in addition to your primary job. (It is called a side hustle for a reason, right?) With that in mind, checking in with yourself and honestly considering whether the extra income is worth the extra stress and strain is crucial.
“Some people have a 9-to-5 job, four kids, a husband and two dogs, and they are already stretched thin, and they just can't,” Weir said. “That's okay if you can't. Then you just need to focus on how you can increase your income with what you’re already doing.”
Weir knows that strain well. She said she suffered a mental breakdown while working three side hustles, and now, as a financial educator, her message is clear: No amount of money is worth the disintegration of your mental health.
“Your mental health is more important than paying off debt,” Weir said. “It's more important than saving. It's even more important than investing because you can't have a good future if you're not here on this Earth. That is something that I really preach and try to get people to understand. Money is very important, but it's not everything.”
That can be incredibly hard to remember when the bills come due and you’re not sure how you’re going to pay them. It can be overwhelming and leave you feeling powerless.
I’ve been there. I remember having 38 cents in my checking account. I remember not being sure if I could get home from work because I didn’t know if I had enough money to get a subway ticket since my credit cards were maxed out. It was terrifying, but even when those times are dark, you have options.
If you don’t know that you can pay your credit card bill, call the bank and let them know. It can be scary to be that vulnerable to a giant, heartless megabank, but the truth is that they –- and most any other lenders, too -- have hardship programs designed to help folks in a short-term financial pinch by offering temporarily lowered interest rates, deferred payments, waived fees and other breaks.
An accredited nonprofit credit counselor can be helpful, too. You should be wary of companies that make promises that sound too good to be true (because they probably are), but there are also plenty of organizations out there that offer real help. The National Foundation For Credit Counseling is a great place to start. They can help you with everything from budgeting and improving your money habits to negotiating with your creditors and creating a debt management plan.
There are plenty of other options that could work for you, too, depending on your circumstances. However, so many people don’t pursue them simply because they don’t even know where to begin.
“It's ultimately about education,” Weir said. “It really is about letting people know there are options because it's not like we're brought up with this. I was never taught about financial education. I was never taught about side hustles growing up. I was never taught that I could earn more, be better.”
“Then I took my first personal finance class when I was 19, and that started the gears going and stripped away the fear. Then I started my debt-free journey in 2016 when I was 22. Once I stepped into that world and started educating myself, the fear just went away. I was like, ‘Well, I can either pass the time and do nothing to change anything or I can pass the time and educate myself and learn about all this stuff and not be afraid of what I can do.’ And that's what I decided to do.”