How To Start A Side Hustle And Make Your Financial Roadmap Smooth With Samantha: The Debtist

The Fellowship of Penny Calling Penny
April 22, 2023
How to Start a Side Hustle

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Introducing The Debtist! Samantha Keith, who is a professional dentist, but why “The Debtist”? Well, this is her story. A passionate dentist who graduated with a lot of educational debt. This happened shortly after graduating from dental school, and she ended up with a debt of over $5000. Her opinion is that saving money implies becoming more financially savvy, and becoming smarter with money opens the door to discovering innovative ways to find contentment in things that do not entail consumer culture, as well as how we can continue to embrace a simple life.

At a young age, student loans can be extremely stressful, but we are ultimately responsible for our debts, the stress of amassing financial wealth and pursuing our dreams. Although all of this is extremely stressful, there is a real way that you can create your own financial roadmap and maintain it over the course of your life. After all, everyone else is dealing with financial issues, and there is still a lack of information on this subject. Our conversation with Samantha will cover how debt builds and how to shrewdly pay it off. Additionally, she’ll also shed light on how side jobs can actually help one supplement their income and some really great advice for those just starting out with side hustles.

Q1) Before we start, could you please give us a little background about yourself and let people know who you are and what you do?

Of course! My name is Samantha Tilapaugh, otherwise known as TheDebtist. I am a zero-generation immigrant from a third-world country (The Philippines) who graduated from dental school at age 26 with $575,000 in student debt. I embraced the moniker after going on a ChooseFI podcast and sharing my story, one laced with the American Dream and the unequal social and financial footing from which we all start. 

They say acceptance is the first step in battling anything, and once I embraced my debt, I was able to tackle it aggressively and with gusto. Facing it head-on took courage, but it freed me from the chains of debt enslavement. Unlike the majority of graduate students, those who rely on student loan forgiveness programs that last 20 to 25 years, I wanted to be free sooner than the standard repayment time of 10 years. I made a goal to be debt-free after 7 years.

At the same time, I made a promise to myself and my husband that we would not live a life of deprivation. It didn’t make sense to work towards freedom while being trapped in the hamster wheel of everyday life in the present moment. I refuse to work a typical M-W 9-5 and work only part-time as a dentist. In order to pay back the debt, I instead made my hobbies and passions money-making side hustles. I do what is fun, interesting, and enjoyable for me. I have full autonomy of my hours, which are flexible, own my “businesses and roles” and get creative with ways to make money. 

Related Article – Ditch Your 9 to 5: 5 Best Ways to Make Extra Money Today

I am also creative in getting our needs met without spending post-tax dollars on them. For example, we have traveled to 7 countries (New Zealand twice, Australia, Germany, Spain, Iceland, Canada, and Mexico a handful of times) and multiple states in the US by travel-hacking using credit cards. Likewise, running a blog allows me to receive products for free. Our house is outfitted with modern brands that are gifted to us in exchange for blog features, reviews, and Instagram reels. By reducing our spending, we can keep most of our earnings for the loans.

Q2) How have side hustles helped you with your finances? 

Tremendously! Side hustles allow me to live a flexible lifestyle. I work part-time in my profession while meeting my financial goals. Meanwhile, I get paid to do what I like to do.

My side hustles were born out of the opportunity. At their core, they are simply things I enjoy doing that I realized I could get paid for. It started with my blog. I originally wrote the way I would in a diary or journal, not for the public but for myself. I took a course on how to monetize the blog through affiliate marketing when I heard the writer of the course guestspeak on ChooseFI. This started the entire process of monetizing it. The blog was my first side hustle.

My second’side hustle’ was being a landlord. My husband and I were not happy with the rent prices in Southern California. We were staying at an especially nice place, which came with a high rent price of $2,800/month. We reached out to people we knew and ended up finding a roommate who stayed with us for 3 years! We charged that roommate $700 a month, then negotiated with our landlord by offering to handle maintenance as needed in exchange for a discount on rent. We negotiated the rent down to $2,600/mo and with the roommate’s payment, our portion of the rent was reduced to $1,900/mo – a $900 savings per month, $10,800 per year.

This helped us save money for a down payment on a property. We bought our first live/work loft for $25k down in September 2018 – unheard of in SoCal! That property ended up gaining a lot of equity. We bought it for $499k in September 2018 and sold it for $660k in November 2021. We sold it after our roommate left in September 2021.

Once we got a loft, I signed up on Rover to be a dog sitter. I have always loved pets, and I thought pet-sitting would be a great counterbalance to the stressful days of dentistry. We also adopted a toothless cat around this time! I did Rover from January 2019 to when the world shut down in March 2020. I was not happy with the few clients that I received from Rover, so when we sold our live/work loft in November 2021 to move to a different home, I started my own dog-sitting business, RMVTail&Paws, named after our new location and last name. Within six months, we were making over $1,000 a month in pet-sitting. For the past 3 months, we have consistently hit this number. At the height of summer in July 2022, we made over $2,000 watching over pets. 

I also got into bread baking. Pre-pandemic, the sourdough fad hadn’t taken off yet, so there were a few of us who knew how to ferment bread for 24 hours. I ended up becoming an early morning bread baker for the only sourdough company in Orange County, Rye Goods. At the time, we were baking bread in someone’s garage. The early bread baker shift is from 2 a.m. to 6 a.m. I was able to do it around dentistry because it was in the middle of the night. After three months, I learned that I could open my own bakery with ease, so I did just that. opened a micro bakery called Aero in the summer of 2019. I started off by selling bread directly to customers, and eventually had my bread in one coffee shop, one restaurant, and at a pop-up in a marketplace. I hired my roommate as my one employee, and we baked out of our home kitchen. In March 2020, I closed the bakery, along with everything else. And less than one year later, when the world started to return to normal, I returned to Rye Goods as their wholesale director when they opened their first brick-and-mortar location. Now I manage their wholesale accounts, onboarding new clients, and managing accounting and billing twice a month. I do the work remotely in the comfort of my home, wearing PJs. I get to meet and talk with local coffee shop owners. It has been a fun and easy job. They are now opening their second brick-and-mortar location and have plans for a third. 

Q3) What suggestions would you give to people who are beginners at this and want to choose a side hustle for the first time? 

Do it for love, not for money. Or if you do it for money, make sure it’s for the love of money. Side hustles are hard work, especially if you are keeping your day job. You need to have the motivation to keep going, or at least something that energizes you. That’s why it helps to tie your side hustle to something you love. This has worked out well for me because I LOVE all the things I do. As you can see, these side hustles are born from things I enjoy – writing, taking care of animals, baking bread, etc. If I were to do my side hustles for money alone, I would get burned out. It would feel like WORK. The entire point of this journey was for us to not be enslaved by debt. It would feel wrong to work for the sake of paying off the loans. It would be against our mission entirely.

Secondly, I would nix the idea that we are born to do one thing. Or that we must stick with our career path. For me, opening a bakery without any sort of culinary degree or training seems impossible, but I did it. You can do anything you set your mind to today. Don’t let your degree or license dictate what you can and can’t do. Think outside the box. You can make money doing anything. For example, my neighbor washes and cleans cars as his side hustle. The person who lives across from me grooms dogs in her garage. One of the parents that I dog sit for runs a wedding and events planning gig on top of her day job. The opportunities are endless. 

Lastly, it’s all about pricing. Do not undersell yourself. Pay what you are worth. Just because it’s a side hustle does not mean you need to get paid less for it. It’s not about the money, but your time isn’t free. That’s why I chose to make money doing what I like to do. 

Q4) How do you manage to maintain a work-life balance?

It all comes down to time management. I run a very tight ship. Being a typical Enneagram Type 1, I am an avid planner, micro-manager, over-communicator, and detail-obsessed. My time is scheduled to the minute. I time-block my day into chunks of work and play. And when I shut off from work, I truly do shut off!

Every morning I jot down the top 3 things I have to prioritize that day. I also write down one thing I look forward to most and one thing I will do to self-care by the end of the day.

The thing I look forward to most can be as simple as “reading my book for 20 minutes” or “grabbing Yogurtland with my parents”. The self-care item can be as easy as “lighting a candle in the evening” or “using a face mask”. 

Once that’s done, I plan my day. Sometimes there will already be tasks jotted down for that day that I added days before. I will tackle the most difficult tasks in the morning. Around 1pm, I revisit what I have left and either cross off unnecessary tasks, delegate tasks to others, or push them to a future date.

I will also schedule a personal time for me and my husband, especially in the evenings and on weekends. I time-block movies, board games, and social events into the schedule. On weekends, there are pool days registered for a three-hour time block, date nights on Fridays, and “Individual relaxation time.”

The important thing is to stick to the schedule. Be disciplined. But also, make sure you schedule things appropriately. If I know my ‘work-life’ schedule will be busy that month, I take special care to double down on freeing up my spare time. I reduce social events so I can focus on personal restoration. I increase self-care activities or choose relaxing activities over rigorous ones. It’s all about allocating your life energy correctly.

Related Article – 13 Best Side Hustles for Night Owls

Q5) Can you share with us some of the challenges you face while managing your personal life and side hustles? 

I think the biggest challenge I have is managing the stress that comes from doing too much. When I am overworked, I tend to be agitated, on edge, and anxious. This can certainly affect my personal life. I am lucky in that I have a great social support system in the form of my husband, my parents, who live down the street, and my sister, who I speak to every week even though she lives in Spain. I also have a sister-in-law that always has my back and a team at the dental office that takes really good care of me. 

Otherwise, it all goes back to running a pretty tight shift. My free time is precious and I guard it fiercely. When I take time for myself or my family, I put my phone on airplane mode, put the laptop away, and don’t look at emails at all. I don’t even have an email app on my phone. I am actually known to respond very infrequently to emails. And I never pick up phone calls. I used to have a voicemail that said, “I am trying to allocate my time appropriately.” This voicemail will not be listened to and will be automatically deleted. Please send an email with all your concerns, and if this is an emergency, feel free to text me, and I will respond as soon as I can.  

Even for my family members, I place boundaries. I communicate with my husband when I need alone time in order to relax, in which case he knows to stay downstairs in his office while I am upstairs. I communicate what time we can reconvene. When I moved to a house

down the street from my parents, I had a sit-down with them and asked if they could announce whenever they wanted to come over ahead of time so I could plan ahead. I did not want them to ‘just swing by’. Boundaries are necessary and healthy. I have really good, strong relationships because of my transparency about my needs. 

Q6) What ways do you follow to find clients?

Building a community has always been a pillar in my life. I find clients by genuinely being interested in helping others, engaging in my local community, and spreading the word through word of mouth. One can certainly rely on social media to grow, but I prefer personal

connection and face-to-face interaction. I am an open book when it comes to engaging with people. I offer my services to everyone around me, not in the interest of making money, but in the interest of being useful. 

At the dental office, I will talk about the dogs I dog-sit. At my workout class, my instructor will mention how I am her dentist. When I volunteer at the community farm, I will mingle with

dental patients. In the blog space, I talk about my side hustles. The parents I work for always ask about the bakery. I bring in boxes of pastries for my hard-working dental staff. 

I believe in the full expression of the self. I believe in radial networking. When I was starting this blog, I was given the following advice: “If you want to write about finance, you need to only write about finance and capture the correct niche audience in order to grow your numbers. This is the only way you will be profitable.

Unfortunately, profit is not what drives me, and as you can see from my blog space, I never took the advice. I write about all the things that make up my life, and I believe in growing a

community using a ripple effect rather than a linear model that could have a further trajectory but arguably a smaller sphere of influence. 

Q7) What are the most common and well-paying side jobs? 

I don’t think there’s a right answer to this one. I believe that the most well-paying side jobs are the ones you genuinely love to do. It all boils down to how genuine you are, and how you can translate that to others. If people see that you love what you do, they will pay you good money for it because they know you are invested, care about the end result, and are passionate about your work. I did really well with dog-sitting in a short amount of time because I absolutely love taking care of pets. I make sure to take them on play dates at the dog park, go on frequent walks, and cuddle with them on the couch. People saw that I cared for their pets, and that is why they referred me to their friends and family. Another person could start a dog-sitting business, but if they do it just to make money, then referrals may not flow so commonly. Taking care of our client’s pets like they are family is why our dog-sitting business makes $1-2k per month!

Q8) What tips would you like to give to our audience to enable them to start a side job without interfering with their primary job?

Boundaries are key. Time-block your schedule into appropriate hours. Be strict with yourself and don’t let one job bleed into another. It can always wait. To help form the proper expectations, communicate with others that this is your side gig. Tell them what your primary job is and what the normal hours are. Then tell them what you can deliver and be honest with what you cannot. Instead of fearing losing customers by telling them your limitations, you will actually gain their trust, understanding, and forgiveness.

Q9) As we have seen in recent times, the urge to earn from surveys has grown. What do you feel about it?

To be honest with you, I have tried it once, but it does not sit well with me. I feel like surveys help the market economy take money from others, and I prefer to work for the people rather than big companies. As a blogger of slow and simple living, I am quite intentional with the companies I partner with. However, with surveys, one can’t be as mindful. Surveyors make money through quantity and by helping all sorts of companies—even those that have misaligned values. I prefer to provide services to people I know rather than help big companies grow. So, from a moral perspective, no thank you. It’s not for me.

Related Article – Best Survey Sites to Make Money in 2023 (Join Free)

Q10)  Before we wrap up here, are there any more insights or tips that you would want to share with the people who are interested in side hustles and want to make the most out of it? 

Be your genuine self. Find a hustle that makes you happy; otherwise, it won’t be sustainable. Don’t limit yourself to your career or degree. You can literally make money doing anything. Be honest with your clients and with yourself. And run a tight shift. Don’t forget about your own needs and those of your family. When it’s time to clock out, completely clock out. All this money-making stuff can wait. I will leave you with the following resources I made for my readers:

·        A free guide on how to start a dog-sitting business.

·        My top 5 small business tools in this blog post.

·        How I started monetizing my blog.

·        The Ever-Growing Ways to Earn Extra Income

·        15 Early Morning Jobs to Jump-Start Your Day

Check out more information on The Debtist! Samantha Keith here. You can reach out to her through mail:

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