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  • Writer's pictureSarah

Serial Entrepreneurship, Self Employment & Side Hustles

Updated: Jan 27, 2021

I've worked for myself for the last few years and have sought out opportunities so that I could continue working from home. My husband and I wanted to start a family and we decided that it would be great if I could work from home and take care of the baby instead of having to juggle daycare costs.

I was terrified but in September of 2017 I took a leap of faith and left my job. Thoughts of what I was leaving behind went through my mind. I was giving up a steady paycheck, health insurance, PTO, sick time, amazing benefits, and that feeling of safety and security that comes along with all of those things. It was a difficult decision to make but it has payed off. Self employment has been so rewarding and I don't regret taking that leap into the unknown.

Back when I first quit my job, reselling full time was all I had been doing to make a living. It didn’t take me long to realize that by diversifying my sources of income I would have a better chance at making enough money to remain self employed because my income is as important as my husbands. At first, I started finding additional ways of reselling. I would sell curated mystery boxes and if clothing wasn’t selling fast enough I would sell the items back to second hand stores to make room for new pieces while still making a profit. Then, I started helping other resellers. I would charge to help list items in their own Poshmark closets. Sellers started to approach me about getting help with sharing their Poshmark closets to help drive sales for them so I pivoted to being a virtual assistant to 100+ sellers over the last 2 years. All this time I was still reselling. I would get payed to do research studies when I could find time between things. Then I started taking damaged secondhand clothing that was destined for the landfill and I would cut the pieces up and make hair accessories. That became Sustainable Accessories. Since I no longer had all of my eggs in one basket it felt like a huge amount of my stress had been lifted. It also gave me the opportunity to pivot if something was not working out or if I started to loose interest.

My journey of being self employed has been long but it has also showed me where my true passions lie. I enjoy helping others and feeling like I’m a part of something bigger than what I’ve built for myself. Freelance/influencer marketing and social media management bring me a lot of joy and help me stretch my creativity. One year after creating Sustainable Accessories, I finally plan to focus on growing that business while phasing reselling out. I’ll still source items while out thrifting as I’ll have a curated secondhand clothing rack at a local business starting this upcoming month. I’ll also still sell items in my Instagram shop and Poshmark closet. But, on a much smaller level and I won’t commit nearly as much time and office space to reselling as I have the last six years. This may be the end of reselling but it may also just be a temporary time out, who knows. What’s great about being an entrepreneur is the fact that you have free reign on what you choose to do and how you pivot in the years to come.

Working smarter not harder and streamlining processes has been a priority especially since becoming a mom and surviving my way through the pandemic. I’ve found things that have worked really well and others that definitely didn’t. I’m working on a coffee recipe ebook to finally have a form of passive income. It’s a little passion project which is important just so the work you’re doing continues to bring you happiness. Below are the reasons I like to think of myself as a “Serial Entrepreneur” and what I currently do to help support my family.


Reselling Thrift Finds (Poshmark, Mercari , Ebay, Instagram, FB Marketplace)

Resale Virtual Assistance (poshmark closet sharing, cross listing, closet reviews, photo editing etc)

Curated Secondhand Clothing Rack at Local Business (sold on consignment basis)

Affiliate Marketing & Brand Partnerships (sponsored posts/stories on IG and discount links)

Sustainable Accessories (wholesale, in local shops/markets and on website)

Social Media Management (manage small local businesses' social media accounts, create content, brand strategy)

Research Studies (L&E Research, Wolf Group)

Content Creation (Instagram page)

Coffee Recipe Ebook (coming soon)


One thing I like to remind myself and others is if you never try or you never take that leap of faith, you'll never know. I'm underqualified for some of what I do now as I don't have a marketing degree. But if I never would have sought out those opportunities, I wouldn't have been able to list them above for ways I'm able to support my family. If you're stuck on trying to figure out where to even start, my advice is to just start. You'll figure it all out along the way.



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