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Sidepreneur: My Side Hustle Journey

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Last Updated on September 6, 2022 by Daniella

My side hustle journey started in high school when I first figured out how to resell clothes. Except this first run in with side hustling was for the wrong reasons and ended up being toxic to me.

After that I tried several different side hustles from being a brand ambassador, to a freelance web developer, painter, blogger, freelance writer, and now blogger and sidepreneur.

I’ve never shared that story and journey until now.

What is a sidepreneur?

After trying so many side hustles in the last 15 years, I never knew of the term sidepreneur until about a year ago.

I came across it in Instagram hashtags I think and loved it when I first saw it. It was finally a term that defined what I did.

A sidepreneur is exactly as it sounds – someone who runs a business part time less than 20 hours a week. However, many sidepreners may spend well over 40 hours a week on their businesses.

They could also run it on the side of their full time job or part time job.

My Side Hustle Journey

I’ve tried and done 19 different side hustles in the last 15 years. It was nothing short of my need to constantly try something new to feed whatever “creative bug” I’ve caught at that time. I always enjoyed trying something new to see where it would lead me, plus I also always had a bill I was trying to pay off.

When I go back and try to think of all the different side hustle’s I’ve done, time doesn’t become so linear anymore. Some of these side hustles were born out of past ones I tried and brought me to a better option, or made me realize when it didn’t fit and I had to move on. 

My day job is in tech so web development and many online side hustles were something that I felt more natural trying out since it was stuff I already did in my day job. Use your strengths and current skills to your advantage when trying out side hustle ideas.

The different side hustles I’ve tried over the years are:

  1. Selling my stuff
  2. Selling my plasma
  3. Clothes reselling
  4. Live painting/sold paintings
  5. Freelance web developer
  6. Brand ambassador
  7. Snow plowing
  8. Waitress
  9. Pet sitter
  10. Mystery shopper
  11. Online research studies
  12. Blogger/content creator
  13. Freelance writer
  14. Freelance designer
  15. Consultant
  16. Coach
  17. Reseller (like thrift store flipping) on eBay, Poshmark, Mercari, and more
  18. Etsy seller
  19. Affiliate marketing
  20. Course instructor
  21. Speaker

Fun fact: After trying all of these side hustles, my first LLC was with my blog, I Like to Dabble which originally began as a hobby to document my financial and side hustle journey. All of my prior side hustles had always been under a sole proprietorship.

Related: How to Legally Cover Your Side Hustle

My Favorite Side Hustle

At the time I was working to pay off debt and was also reselling with my wife. I had just gone through 1 layoff, started my blog, and then the 2nd layoff hit. Blogging became a creative outlet to cope with some work trauma from that time. The more I submerged myself into the creative process of blogging, I became interested in ways I could make it an income stream over time.

4 and a half years later that blog is now a 2 time award winning and globally recognized side hustle blog with a community of over 100,000 dabblers. Even though the blog is 4 and a half years old, it wasn’t producing much income until recently.

The income history of my blog:

  • 2017: $1,000
  • 2018: $9,870 
  • 2019: $29,887.26
  • 2020: $40.007
  • 2021: $60k
  • 2022: Goal is $100,000 for this year 

Which also includes these income streams:

During this time I did take a new job and continued to work full time. However, I was working remote so this made my sidepreneur lifestyle easier than if I had to commute to a job.

Setting boundaries in both my work and my side hustle was still important though, as you can’t maintain any sort of balance without setting those boundaries both with yourself and others.

Blogging has been one of my favorite side hustles because it is something I can easily set and keep boundaries with. I can do it remotely, on my time, and by my rules. But I had to learn the hard way.

In the beginning, I came close with burnout as I was spending a lot of time pouring content into my baby blog. I was reading, learning, and trying so many things. At this same time, I was also experimenting with different income streams but this took a year until it was making just under $1k a month consistently with the blog.

Over time, I could make money with freelance writing or a brand partnership one month, and with a workshop on something readers have requested the next month. If I chose to not work much one month I would still be able to make semi passive income with ads, affiliates, and digital products. The flexibility was freeing. It is also something I enjoy so much that I now have 2 blogs (but 1 is still very much a hobby at the moment).

Blogging is thrilling to me. It was never my passion but through my own curiosity with it, it became one of them that I just had to see through. I never thought I would enjoy writing but the more I did it creatively as a way to release a flow of thoughts and ideas, it was exhilarating. Blogging became very much like having a living book.

This is all to say – When you’re thinking of a side hustle to start, where does your curiosity go? Feel that out.

If you need a website or want to start a blog, get started with Bluehost at a discounted rate just for ILTD readers. 

My Least Favorite Side Hustle

After I turned 21, I heard from friends about a popular side gig that a lot of my friends were doing. It was doing being a “brand ambassador” for alcohol, cigarette, college, and sports brands. It mainly consisted of dressing up in branded clothing, going to establishments, hand out free stuff or ask for people to fill out surveys for free things, etc.

When I worked as a brand ambassador for Bacardi, I would go to grocery stores, liquor stores, and local bars with the other women and give out free shots. I had serving and cocktail waitress experience and enjoyed the fast paced nature of the work. It paid $25+ an hour at the time which was about 2011 and we also got a lot of free stuff.

At this time I did the same sort of work for other brands like Camel and the NFL. It was a really lucrative side hustle for me because it was always on the weekends and I could make a lot in a couple of hours. Then I found a gig that claimed to pay more that ended up being the worst side hustle I had ever tried.

It was for a company called Boobies Rock who first claimed to be looking for brand ambassadors. However, they just wanted us to sell a bunch of merch and ended up being a fraudulent breast cancer charity.

They had a downline sort of structure too, similar to MLMs and my first encounter to a company like that. It is my biggest regret and largest waste of time – well I guess not because you live and you learn, am I right!?

Related: MLM Scams and Horror Stories: The Screwed Up World of Multi-Level Marketing

Lessons Learned

I am a sidepreneur with a full time job. I don’t think you have to leave your job to be a successful business owner. You can run a business and keep your job if you truly enjoy it. If you don’t like your job, then quitting for your side hustle might be ideal for you.

If it get to be too much and you have to decide which to keep, then that decision is yours to make. But the importance of having a side hustle is having those options, especially when one income stream goes away you have another to fall back on.

It all depends what is best for you and your situation. Online “success porn” may make you feel like you need to do one thing or another but remember that every person’s situation is nuanced. You have to do what is best for you and what best aligns with you.

I’ve gone from bad decision to bad decision. From toxic side hustling to building a business. But I’m still no expert.

No one is perfect and I think it is important to highlight the reality of who I am in the sea of online entrepreneurs trying to help you make money.

Every failure has brought me a new lesson and lead me to where I am today.

My number 1 lesson remains to be this: continue to be open to new learning and changing your course but stay true to you.

And be weary of people and companies trying to take advantage of you.

If this was helpful to you, let us know in the comment below and share 1 thing about your own side hustle journey!


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