Why Side Hustling is My Cup of Tea

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side hustling

I have been asked by numerous people since I started by blog, ‘Why don’t I become my own boss and stop working for the man?’  The answer to this question is simple, yet complicated.  The quick and dirty version is that I have been there and done that before.  I have been on my own and it wasn’t something that I really enjoyed.

As John has talked about before, owning your own business is not all rainbows and unicorns.  It takes a lot of work. For those who don’t know me, I started and built up a successful e-commerce company up to a point where it was selling over $1 million in annual sales.  It was a one man company. I was everyone in the company and I made it work.  I was in an industry where the margins were paper thin and the competition was fierce.  It was hard work, but the fact that I built it kept me going.

After some time of owning this company, I came across a job opportunity which I couldn’t pass up. I took the job and ran my company at night and on the weekend.  It was a stressful time for me.  I did this for a few years and then realized I could no longer do it. I shut down the company and sold off some pieces right before the holiday season.

I have never regretted that decision.  It changed my life.  I know there are many others out there who run companies on the side of their full-time employment and I applaud them for it.  I couldn’t keep up with it as the demands of a retail e-commerce company are great.  This is especially true when you are selling so much merchandise.  The problem for me is I couldn’t stay away from owning my own business.  I just love being an entrepreneur.

Enter the Sidepreneur

I never really considered myself a side hustler until I read about the term on a blog somewhere. That was exactly what I was doing with my business after I got my full time job.  I still have that same job by the way, but I love every minute of it. Side hustling has become part of my culture and my financial plan.  People always tell me that I work too much, but I tell them I enjoy the extra money and the flexibility of earning extra money.  I have officially become a sidepreneur.

Business ideas roll around in my head constantly.  I look at the world around me and try to react to what is going on.  Some things stick and others fall apart quickly. That is the life of an entrepreneur.  Starting a new business or launching a new service excites me.  I get all worked up over it.  It gets my adrenaline pumping for sure.  My adrenaline is currently pumping for my technical blog management service that I just launched a few weeks ago.  I really love blogging and the technical side, so this was a natural fit for me.  This is why I love side hustling.

Security and Flexibility

Any small business owner will tell you there is no security with owning your own business. They will also tell you they have more flexibility than a typical 9 to 5 job.  I tend to agree with those concepts.  The issue for me is I need the security of a full time job.  I want to know how much I am going to make each month and when I am going to make it. It really keeps the budget flowing strong.

While no job is secure, I feel a full time job might be more secure than a small business, depending on the concept of the business.  I have seen too many people base their business off of one client and then the client’s needs change.  There goes the business.

I have found that side hustling gives me the best of both worlds.  I get to have the security of a full time job, plus the benefits. I also get the flexibility to earn more money on my schedule.  I don’t have to take a job if I don’t want to and I can be more selective about what I do take.  I am not trying to be a snob here, but flexibility is important to me.  I enjoy spending time with my wife and son, so I don’t want to sacrifice those times.  Along with security and flexibility, my earning potential directly results from what I put into my side hustle.

Technically, my earning potential is unlimited, so I like having options.  I can diversify my services and where I make money, so I am better off financially.  Truth be told, side hustling is my cup of tea.  I love it and that is why I am such a strong advocate for it.  Having a successful side hustle is one of the reasons why John and I started Sprout Wealth.  We wanted to teach others how to do the same thing.


Would you rather be a side hustler or a full time self-employed business owner? Are you an entrepreneur at heart? Do you think you have what it takes to run a side gig alongside your full time job?


Photo courtesy of: Mixunit

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Grayson is the owner of Debt Roundup and Empowered Shopper. He also co-owns Sprout Wealth and Eyes on the Dollar. After going to battle and winning against consumer debt, he decided it was time to learn how to use credit wisely and grow his wealth. He discusses all things personal finance and is not afraid of being controversial. He also is a freelance writer and blog manager.

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  • I have business ideas always going around in my head too. The problem for me is focusing on just one and seeing it through to the end instead of getting caught up in the new exciting opportunity.

    In answer to your question – I personally like the idea of being a side hustler. It allows me to keep my day job where I can interact with people face to face, but it also allows to to earn a good chunk of change on the side. Plus, if I ever get sick of “the man”, my side hustle should keep my family fed for a while.

  • I’ve been side hustling for a few years now and I don’t foresee that changing anytime in the near future. I love the security my day job offers – plus the fact that it’s a career with many opportunities to make more money year-over-year – and I love the fact that side hustling helps with my “entrepreneurial itch” while also giving me the flexibility to stop if I need/want to.

  • Dave Lalonde says:

    Being a self-employed business owner is a LOT of work. I give you props for even trying to balance that for a while. I’m very grateful to say that I’m at a point where I’m content with where I am, but I think side hustles are an awesome idea. I enjoy reading BudgetsAreSexy to read about all the different ways to hustle. It’s very interesting to see how creative people are in managing that in their schedule!

    • Grayson Bell says:

      Being self-employed is a lot of work. I do have my own business, but it is all around freelancing and blog management services. That makes it easier for me to diversify.

  • Unfortunately, no full-time job is secure. My brother- who has worked for the same company for over a decade and constantly wins company awards- just found out that he’s losing his job. You just never know these days!

    Anyway, I agree with you that side hustling is a good compromise. It’s like having your cake and eating it too =)

    • Grayson Bell says:

      First, sorry to hear about your brother. You are correct. Nothing is secure, either full-time jobs or self-employment. That is why I like to diversify my skills and keep options open at all times.

      I do like cake and eating it too!

  • Great blog post. I too am a sidepreneur, and I find it gives me amazing freedom to pursue things I find enjoyable, but wouldn’t necessarily want to make a full time career or business from. Successful side hustles for me have included dog sitting, furniture restoration, mural painting for children’s rooms, and organising conferences and sales events for friends with small businesses. Operating in such a way gives me flexibility to spend time with my family, I can up my hours if I need more money, and down them if I am needed more at home. And I am never ever bored!!

  • Like you, Grayson, I constantly have ideas rolling around in my head, but never compelling enough ideas that we’re willing to risk it all and leave Rick’s job behind. I can see it happening someday, though, if and when the right opportunity and timing come along.

  • Cat says:

    Having done both I can attest that it’s a pretty tough choice. I don’t miss getting off of my full time job only to work 3-4 more hours at night but I do miss that nice paycheck I got since my income has dipped now that I have the beans.

    • Grayson Bell says:

      Yeah, I have done both and I don’t mind working at night. I have worked a schedule where I can enjoy time with my family and then work at night when they are asleep. It helps when you are a night owl.

  • At this point I’d rather be full time and earn extra money side hustling. I miss my 401k and health insurance! 🙂 So I’m looking for full time as well as expanding my freelance client/project base.

  • Lauren says:

    Having a job and side hustling seems pretty good to me. I’ve been freelancing for a few years, and I think I’d like to get a job outside of the home for awhile, as well as keep up with freelance writing.

  • Hey Grayson, I ran a side hustle for 2 years while I worked for the man. Eventually, I was able to quit and I’ve been working for myself since January. I wouldn’t have it any other way personally, but I can understand why some people would rather work a salary job and run a side hustle.

  • I never had the “luxury” of side hustling because my compliance area wouldn’t allow it so I just went all-in on my biz. I researched and did a bunch of work leading up to the leap but it was definitely a big leap of faith. I am glad that I did it because it has led to so many different opportunities that I never would have imagined but it is definitely tough work too.

    • Grayson Bell says:

      If I didn’t have the opportunity, then I don’t know what I would do. I don’t really want to jump all in right now, but I do love making money on the side.

  • Having a full time and family I cannot balance my time to have side hustling. To be a successful in side hustling business requires more time especially if you are in the honeymoon stage of your company.

    In the near future, I will try to venture to be boss of my own business.

    • Grayson Bell says:

      It takes a lot of work. I have a full-time job, family, and side business. I have worked out a schedule that allows me to be productive, yet spend quality time with my family.

  • E.M. says:

    I think it’s a tough decision. Working for yourself seems alluring if you’ve had bad experiences with your regular job. If you love your day job, then I can see how it makes perfect sense to side hustle. Unfortunately, I haven’t found a job that excites me enough, but I am definitely open to the possibility if the right one comes along. For now, i’m trying to freelance, and I’ll be looking for a part time job for some stability.

    • Grayson Bell says:

      It is always a tough decision. It really depends on each person’s situation and what they are comfortable with. I love my regular job and the company I work for. I just can’t sit around at home, so making extra money is my thing.

  • I work a salaried position and live off my side hustle incomes.

  • I do both, and side hustling is my fave. I get to pick the amount of effort that goes into it.

  • Jason B says:

    I love the side hustling aspect right now. One day it will make enough money so that I won’t have to work for anyone else, but until then I’m fine with it being a side hustle.

  • I can understand your perspective. I definitely need the income of my full-time job right now. The blogging community has opened my eyes that there could be a possibility to do something once I retire. I like learning, teaching and trying new things so for now I’m just content to do that and see later what the future holds.

  • I love being a sidepreneur. It’s a lot of fun and I love that at least part of my income is made by being my own boss and working for myself. But I struggle with thinking that I could stomach quitting my job and going out completely on my own.

  • Amy says:

    Full-time side hustling sounds very appealing to me, especially the flexibility and being my own boss, but I haven’t figured out how to make it reliably lucrative just yet. I think you’re right that both “real” jobs and side hustles have distinct pros and cons, and the decision is different for everyone.

  • I currently side hustle in addition to my full-time job. I used to love it, and still do for the most part, but I am seeing the potential for success as a freelance business owner. Perhaps this is because I have always worked in nonprofits, therefore have always had hard work and low salaries. I’m ready for a pay bump. 🙂

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