Over the past decade, since starting a greeting card company and transitioning it into this blog, I’ve met with many people who have sought advice on their product idea, including how to make it, where to sell it and what they can do to promote it. The same pieces of advice are given to each person; the things that I’ve learned through trial and error. However, it still requires making their own mistakes. Most people are too afraid to make those mistakes.

Myself included lately.



Pool Season 2014

“WELCOME…. to Pool Party Season 2014! With your hosts… Annie and Rachel!” We made the announcement, more to ourselves than anyone else, with arms outstretched in excitement. Months had been spent doing ab exercises together, figuring out the perfect hair extensions and finding cute swimsuit coverups.

At 1pm on a Saturday the poolside cabanas at Maya Day and Night Club began to fill in. It was the beginning of April, and the Scottsdale pools were officially opening for the summer.



“And to your left we have the bachelor partiessss…” Rachel said in her best announcer voice as we walked across the pool deck side-by-side in swimsuits we had saved all winter to afford.

“And to your right we have…” before I could complete the sentence, a Maya hostess approached us, welcoming our self-proclaimed “Welcome Committee” into a cabana for free vodka sodas from a giant bottle of Grey Goose.

A sense of pride and pure joy was felt by two 20-something best friends who would later be found dancing across the pool catwalk, blissfully unaware of onlookers. Their only concern was getting their hair extensions and/or designer swimsuits wet.



Pool Season 2018

On a recent Friday at the beginning of April, Rachel and I entered the Montelucia pool in Scottsdale, Arizona. There was no pool party or catwalk dancing or giant bottles of Grey Goose. And in their absence were now adulting concerns that included mortgage payments, business travel and plucking out premature gray hairs.

However, what remained were two excited best friends and a beach bag full of cute swimsuits that the 20-something “Welcome Committee” would have died to have.


“This is one of my favorite new styles,” Rachel said as she pulled a sheer, mint-colored cover-up from the bag. “And you have to try on this swimsuit top…”

As I looked at myself in the women’s restroom mirror, I admired the flattering, patterned top and felt a feeling of pride greater than crashing pool cabanas: “Rachel made this.”

Making Swimsuits

“The reason that I wanted to interview you is because I’ve given advice to a lot of people on how to start something or tips and tricks. And most people don’t ever do it,” I said to Rachel at the dining room table after the pool. “And you’ve actually done it and are getting really good sales on Etsy.”

Since our pool partying prime, Rachel has gained her CPA, found and married a great guy and has become an Experienced Assurance Manager for a Public Accounting Firm. However, that hasn’t kept her from pursuing the swimsuit passion we’ve both shared by combining it with her love of sewing. The final product is RaeLo Swimwear, an Etsy shop and online store dedicated to looking your best at the pool, handmade by Rachel.


Along the way, Rachel has asked questions, including:

  • How to create a logo
  • Where to print business cards
  • How to edit photographs
  • How to record YouTube tutorials
  • How to promote on Instagram

And with each answer, she ran with it, knowing that the results were not guaranteed, work had to be done and that mistakes would be made. More importantly, all of it has been done quietly without many of our friends even knowing. Through trial and error and sticking to her passion, her shop now has 700+ sales, hundreds of positive reviews and nearly a thousand Etsy shoppers who have favorited it.


How to Turn Your Passion Into a Successful Side Business

A second, more secret reason that I wanted to interview Rachel is that though I am the one who once provided advice, I am the one who needs it now. A quest for perfection and constant second-guessing has kept my recent ideas and efforts from truly becoming revenue-generating projects.

It was my turn to ask the questions, and this is what I learned.


1. Start small

“I knew I wanted to do something on the side because I’m really creative, and I just didn’t know what that was yet,” she said. Rachel started her first Etsy shop by selling clip-in hair extensions – a product that we once spent hundreds of dollars on until she realized she could purchase the hair and sew on her own clips. “It doesn’t need to be this big thing; just start small and see what works for you,” Rachel added.


2. Shift when it feels like work

The beauty of having a side business that you’re not reliant on for income is allowing yourself the time to find what works for you, i.e. the thing you’re passionate about. “I think that the second it starts feeling like work, then you should probably shift what you’re doing.” That’s how Rachel transitioned from hair extensions to swimwear. “Now I love it. I love when I get every order. I love when I get a message from customers. Then it’s not work anymore; it’s just something fun.”


3. Expect surprises

For me, one of the riskiest parts of content or product creation is the uncertainty of knowing whether people will like it. I wondered if Rachel felt the same. “Yeah, I’m always surprised by which ones are popular. You think that you make this brand new suit and everyone’s going to love it, and then they end up loving another one you’ve made instead.”

Because of this, Rachel generally doesn’t keep a lot of stock on hand and spends evenings and weekends sewing as orders come in. “I think there’s a lot of surprises. But you start to learn what people like, and it’s not always what you like.”


4. Market to potential customers; not friends and family

One of the things that took me the longest to learn, Rachel seemed to know right away: your customers may be your friends, but your friends are not always your customers. While I spent years holding onto expectations that all of my friends should be my target customers and readers, Rachel intuitively knew that the two are separate. “I’ve had a few friends purchase just to support my business, but I don’t really market a lot to my friends and family as much as just in general on Etsy.”



5. Leverage skills from your day job

“Has your day job helped you at all with your swimsuits?” I asked Rachel, wondering if her Accounting background aided her creative outlet. “Yes, so much!” she responded. “Having a business and accounting degree has really helped with the finance aspect, including margins and keeping track for my taxes.” Rachel also learned a lot about customer services while managing retail stories in college.

“With swimwear everyone has their own opinion as far as how something should fit so sometimes you have customers who want to send them back multiple times to tweak them a little bit,” Rachel explained. “But I’m actually happy to do that because I want every customer to be as satisfied as possible.”


6. Let go of perfection and learn from your mistakes

“So, what’s one of the biggest things you’ve learned from RaeLo Swimwear?” I asked Rachel at the conclusion of the interview. “That it’s never going to be perfect,” Rachel replied. “I’m a perfectionist so I want everything to be perfect: the packaging to be perfect, the swimsuit to be perfect. And I think that’s a good quality so that everything looks the best that it can, but if not everyone’s happy then it’s okay. Just go for it and learn from your mistakes.”


What I’ve Learned From Rachel

The day after our poolside photoshoot, Rachel had to fly to China on a business trip, and she would return only days later to the middle of accounting busy season. While she yearned for the ability to fully dedicate her time to swimsuits, she hasn’t let that desire get in her way of doing what she can. And doing it well.

While she might have learned how to hire freelancers or Photoshop out a wrinkle from me, I’ve learned more from watching her. She has taught me how to go for it without overthinking. She has showed me humility and that success is often achieved quietly. She has proven that when passion leads, even side projects don’t feel like work and that others – even strangers – can feel the piece of your heart you’ve put into it.


Without her knowing, she’s reminded me to celebrate the joy that comes from pursuing your outlet – whether that’s swimsuits or a blog or dancing poolside no matter what onlookers think. Because sometimes the difference is in just doing it, no matter if there are mistakes.