Side Hustle Season : Money Matters

Do I have a side hustle? Yes, actually I have 2. (not counting exploring new business opportunities for The Westmoreland Group) 

I remember the first side-hustle I had, selling girl scout cookies. It was simply a means to an end – the end being one of those shiny gifts in the fold out catalog I poured over for hours before each selling season. I can’t recall exactly but I think myself and all 3 of my sisters were in Girl-scout Troops and selling cookies at the same time to the same group of customers. We had my Daddy’s co-workers, church members, family, friends, and the neighborhood – this was when selling door to door was a thing. This was my first side hustle and I did quite well and I distinctly remember the satisfaction I felt when I made a sale. I was determined every year to fill all the lines on that long fold out order form! I wonder what my parents thought about all those darn cookies that then had to be delivered once the orders were filled? I’m sure they loved it – because parents gotta parent right…

When I was in high school I don’t remember many of my friends having side hustles – my parents have always had one or two or three though usually running at the same time in case one revenue stream dried up a bit the other would kick-in. So I know where I get my side hustle spirit from – thanks Henry and Anita. As a college student I remember MANY side hustlers because college students are for the most part broke! There was the girl who waxed and plucked my eye-brows down the hall from me in my dorm. There was another girl who washed hair in Hale Hall (another dorm). There was a person who shall remain nameless that could connect cable channels for you. There was always someone selling mix-tapes that they made using Napster – Christmas Mix/ Greek Mix/ AKA Mix/ Valentines Day Mix/ Slow Jam Mix/ Rap Mix, etc. As a sorority member, I could always find someone who knew how to make Greek things – paddles, picture frames, etc. 

As a graduate student I spent countless hours studying for written exams, practicing for oral exams, preparing my proposal, presenting my dissertation defense and at some point I decided to start baking to help relieve stress. I would start with cupcakes because I was watching TV Shows about cupcakes (during this time cupcakes were all the rage so it was an easy outlet). Although I am a Mechanical Engineer by degree I am also very artistic in nature and as a full-time graduate student I didn’t have much time to explore that side of me. Baking cupcakes gave me the platform I was looking for. I was working as a Graduate Program Assistant in the Center for Minorities in Science and Engineering at The University of Maryland College Park in the College of Engineering at this time. I would bring all my baked treats to work and let my co-workers tell me what was good and what was not. I would find recipes on the internet and try them at home. In time, I received several paid orders for cupcakes and I so I decided to call my baking business Fancy Cupcakes by Sophoria. I really enjoyed baking all those cupcakes and I most enjoyed the reaction of happy customers. After graduate school my work schedule was demanding and I didn’t have as much time to bake as before – I would service a few seasoned customers under a new baking business called Hero Cupcakes over the years but not as many as while in graduate school. 

This year, 2020, I have picked baking up under another new business name called Three Stripes Bake Shop and already have a few cupcake orders. I also am turning a new leaf into baking cakes. I have baked a few cakes over the past years but I am not as skilled in this area – I look forward to learning some new things about baking cakes in 2020. (SIDE HUSTLE NUMBER 1) I already baked a 38th birthday cake for a church member in January and I am taking a local cake decorating class next week at the craft store – I am on my way (again). The nice thing about baking is that I enjoy the process so it is easy for me to keep picking it back up when time in my schedule permits. 

This year, 2020, I will also continue working on the side as a Recorder for some HOA Communities in my local area.  I recently calculated my 2019 earnings from this side hustle were almost $3,000 (pre-tax) which was great for bills I had planned and unplanned.  (SIDE HUSTLE NUMBER 2) This side hustle came through a friend (Cel) with MONEY ears, meaning she can hear opportunites to make money miles away. A friend mentioned the HOA she belonged to was looking for a new recorder and Cel immediately thought, hmmm, I can do that so she wrote up a proposal and that was our first community. Along the way we have build relationships with several Community Management Companies in our local area which in turn have resulted in more opportunities to record on an ad hoc basis. I recorded already this month for one such community just last week. 

A couple of years ago before I was consistently working my 2 side hustles I was listening to a podcast about side hustles and I actually stopped listening to it because I was mad that I couldn’t find myself a lucrative side hustle – at the time I didn’t think I needed one but it sounded like fun to have one. I enjoy my 9to5 supporting my client but is this my DREAM JOB? NOPE! I enjoy the people I work with and I enjoy the difference I make but if I could do this part time and bake cakes and cupcakes the other part of the time that would be my dream job. 

I was thinking I should be able to do what these folks are doing on this podcast but I don’t know where to start. Then after I got over myself I started listening to the podcast again and the host basically said start with what you have and make that into a side hustle. As it turns out I am a decent baker and I am very organized (which helps me immensly in my 9to5). Baking cupcakes/cakes and taking minutes are the perfect side hustles for me. I may not be making millions but I am able to supplement my income enough that I feel both are worth my time and energy. One of my financial goals for 2020 is to pay off my $30,000 student loan balance and these side hustles will help me to advance towards that goal. 

I have heard this sentiment many times and it really is true – start with what you know and figure out how to sell that as a service. Your knowledge and background are all the pre-requisites that you need. You may need to do a little market research, try some things out on your family and friends, use Google to find others who are doing something similar (there is power in community), start small, and grow from there. Your career or life’s work doesn’t have to come from one source and it doesn’t have to only be confined to what you do from 9to5, there are many paths to acheive your vision and walk in your purpose. 

Patience in the process and a willingness to continually learn will take your side hustle dreams far. 

Dream It, Do It! 



Image by Arek Socha from Pixabay 

A Legacy of Making A Way

I once heard Pastor TD Jakes preach a sermon about generational blessings and he gave the metaphor that when the parents are blessed it is like a tea cup and when the tea (blessings) spill over into the saucer that is being passed onto the next generation. (Side-note: metaphor, simile, analogy – in all my learning I have to admit sometimes when I am confounded, all roads lead to Google) When I heard this I liked it and I thought oooooooohhhhh nice, one day I will spill some blessings over for my children (as of this writing I am not married nor do I have children, but maybe one day). 

I also had a second thought,  I sure wish my parents or grandparents would have had some of those blessings (education, cash, property, cash, jewelry, cash, stocks, cash, bonds, cash, mutual funds, cash, houses, cash, silver spoons, cash, knowledge, cash, off-shore bank accounts, cash – you get the point!) to spill over onto me – then I would never have had to struggle, right? 

It made me think of Beyonce’ and Jay-Z and how their unborn great-great-grandchildren are already wealthy which makes me smile more than I should because black excellence is personal (and because Houston girls are lit) . 

I have this exercise I do whenever I feel I am lacking in something or missing out (FOMO) on something I think I need to get through life. It’s simple, I write down what I already have (not really material things…I lie! yes, sometimes material things…sometimes) and I am filled with gratitude. The following list has to do with legacy as it relates to working. The road to success is paved with hard work – no shortcuts there and I have a solid legacy of hard working people in my blood line. I don’t even have to go that far back to see the writing on the wall. 


Mommy (Anita)  –   jobs: 

1. Transcribing  Medical Records  (Summer Job) 

2. Teaching Swimming Lessons at Carver Park (Summer Job) 

3. K-Mart Associate (Women’s Apparel and Lay-A-Way) 

4. Target Associate 

5. Igloo Manufacturing (Putting labels on coolers – think assembly line) 

6. La’ Bon Pain Bakery (Baked and Sold Bread- she was a baker)

7. Sandwich Shop (Work here with my Aunt Jackie and another friend) 

8. Kroger (Baking Bread and Frying Donuts) 

9. Cross-walker (Katy ISD) 

10. Bus-driver (Katy ISD) 

11. Hewlett Packard (Putting together motherboards – think assembly line) 

12. Jeremiah Moonwalks (Owner and Operator) Side Hustle

13. Metro Bus Driver 

14. Molly Maid Housecleaner (This was when there was a uniform that included lots of lace and lots of ruffles and she took us with her on jobs and now I can clean a house like a pro) 

15. In-Home DayCare (At Lakeside Village Apartments – I would sometimes wake up with a small child sleeping at my feet or snuggled next to me in bed, all the children would become KidFirstName Westmoreland) Side Hustle

16. Newpaper Delivery (Katy, Texas) Side Hustle

17. Phonebook Delivery (Katy, Texas) Side Hustle

Grandmother (Barbara Jean) –  jobs: 

1. Cook -Jimmy Walker Restaurant (Kemah, Texas) 

2. Walgreen’s Cook (Texas City, Texas) 

3. Model for Evelyn Johnson Modeling School (Houston, Texas) 

4. Dietician at Mainland Medical Center (this is the hospital where we were all born) 

5. Washing and Ironing Teacher’s Clothes (Wheatley High School Summer Job) 

6. Nurses Aid – John Sealy Hospital (Galveston, Texas) 

Great-Grandmother (Bigmoma) – jobs: 

1. Picked cotton in Madisonville, Texas (Crockett, Texas) 

2. Maid for Dr. Brown (Crockett General Hospital) 

3. Sold Insurance (if you know anything about selling insurance you know the grind is REAL – it doesn’t sell itself) 

4. Breakfast Cook (Cafe’ in Houston) 

5. Housekeeping for Owner of FingerHut Furniture 

6. Shackle Representative (Side Hustle – Selling Health Products Door to Door) 

7. Resale Shop Owner (Hwy 1765) 

8. Childcare Worker 

9. Director/Assistant Director of Galveston County Head Start (I spent many days as a tiny tot hanging out with Bigmoma here, I remember taking naps with my cousin LeLe on those green cots) 


Daddy (Henry) – jobs: 

1. Cutting grass in neighborhood (Started when he was 13) 

2. Filing Station Attendant-  Pumping Gas/Fixing Flats  and other miscellaneous duties (Texas Ave. @ Anita Street) – This was a black owned business owned and operated by his cousins the Crittendons 

3. Banquet Waiter in Holiday Inn Hotel Restaurant (Galveston, Texas) – started in the 10th grade and worked for 5 years 

4. Co-op Program at Union Carbide (Chemical Plant) Summer Job (11th and 12th grade)  

5. Construction – Vox International (Worked in the eqiupment yard and was laid off when the company moved to Houston) This was the only job he was ever laid off from. 

6. Machine Operator / Extruder / Shift Manager / Lab Technician (VanLeer/ITW- Houston, Texas – 40 years – he worked here longer than I have been alive) Note: ITW actually funded part of my college education through a scholarship – shout out to them! 

7. Jeremiah Moonwalks (Owner and Operator) Side Hustle

8. Newpaper Delivery (Katy, Texas) Side Hustle

9. Phonebook Delivery (Katy, Texas) Side Hustle

10. Cleaned Houses (Katy, Texas) Side Hustle

Grandmother (Grandma Rose) – jobs: 

1. Maid – Holiday Inn Hotel (yes, this was the same place my Daddy worked and they had a cousin working there too – this was her first job going back to work after being a full-time mother to her 6 sons) 

2. Flag Waiver – Brown & Root Contruction Company 

3. Cashier – Crittendons Liquor Store (owned and operated byt the same cousins above) 

4. Beer Cafe Owner (Galveston, Texas) 

Grandfather (Papoo) – jobs: 

1. Grain Elevator Operator (Dingy Operator:  Moved rail cars around the yard) – Bunge (Grain Export Company) – he retired from this company the year I was born! 

2. Grain – spillage from company he was allowed to sell, Side Hustle

3. Collect scrap metal, Side Hustle

4. Carpenter, Side Hustle

5. Gardender 

6. Raised Chickens 

Great-Grandfather (Big Daddy)- jobs: 

1. Jack of all trades – Self-Employed 

2. BBQ Cook 

3. Cut Pulp Wood

4. Lumberjack (I should note here that he was at one point struck by lightening and survived, he was 104 when he passed away if I remember correctly) 

5. Carpenter 

6. Farmer (My grandmother noted that when snakes would get after his chickens he would pop off their heads) 

Great-Grandmother (Charlotte)- jobs: 

1. Being a Mother 

I have excelled at many jobs from being a cashier at Gerland’s to the many retail jobs (Nine West and Banana Republic were my favorite – I can fold clothes for days) I held in college and being a full time PhD student (yep, that’s a FULL-TIME job and I have the paystubs to prove it – it ain’t for errrrbody). I have learned many lessons along the way especially the hard truths about income taxes but what I had going into those jobs came from what my family deposited in me by raising me with ‘spill over’ blessings.  

Also, it is interesting to me to find out that some of the jobs I am doing now are very similar to what my family has done. I am currently and entrepreneur with my own consulting firm – I am the boss.  I am currently working on the side as an on and off cupcake and cake baker and looking to take some classes this year to improve my skills. Resale shops are my favorite go-to place for reasonably priced fashion. I also have a side-hustle as a Recorder for Home Owners Associations that I came into a few years ago and has been a great blessing when unexpected expenses have occured. 

My siblings and cousins on both sides of my families also have careers/jobs that align with the family traits of working hard. One of my cousins has recently started her own photography business, LINK. My sister recently started her own interior decorating and handy-woman business, LINK. My oldest sister and my younger brother are now both working at Van Leer/ITW where my Daddy retired from. I have a cousin that is a nurse and one that is a world traveler. I have a cousin that is a cook/chef/caterer. 

My famiilies unofficial motto should be the same as Clark Atlanta University – “I’ll find a way or make one” because that is exactly what we do. It is with much gratitude and grace that we carry on the family legacy of hard work to build our own families and create our own success stories. We are building up from the firm foundation passed to us by our family (native Texan). 

From Victory, 

-Sophoria Westmoreland