Life of an Entrepreneur- Getting Started

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Life of an Entrepreneur

To all my fellow entrepreneurs and curious friends. This one’s for you. 🙂


Day 1.

Day 192. November 12, 2013

Five weeks into marriage, I called Blake. “I think I want to start a photography business. Is that okay with you?” There was a pause on the line. Had I even told him I’d been thinking about this?

When I think about how I started my business over 5 years ago I feel an overwhelming sense of blessing. You hear statistics all the time about how new business have an alarmingly high failure rate. Fortunately for me, I didn’t know that then. 😉 All I knew was I had a really supportive family and a husband who had my back. ????


Aimless Wanderer

I had just graduated college earlier that May. The only problem was it was November and I was no closer to finding a job.

To be fair, I probably hadn’t found one because I’d only applied for a grand total of 4 career jobs over the past 8 or so months. The problem was nothing really interested me and since I’d been working 2-4 part time jobs since I was 15, I didn’t feel the pressure to find something. I was working just as many or more hours as anyone else I knew. (And I was pretty sure I was having a lot more fun!)

However, I had a feeling my time was running out.

Blake and I had been married for just over a month. My summer jobs were coming to an end and it was time to figure out what was next.


My First Camera, Canon, Reble T3i, Rachael Watson Photography


The Idea… Again.

What most people don’t realize is that Rachael Watson Photography is actually my second attempt at starting a photography business and my 4th business attempt.

Coming from a long line of entrepreneurs I was always encouraged to explore ideas. Having watched my parents run 3 different businesses in 3 different industries growing up, there was a lot about doing my own thing that intrigued me.

I don’t remember the first time photography crossed my mind again, but I do vividly remember sitting in the PJ’s Camera parking lot at a cross road. My mind was reeling and I honestly wasn’t sure how the day would end.

I had just spent the past 30-45 minutes talking with Margaret from PJ’s asking her all sorts of questions about cameras. I’d told her I was thinking about starting a photography business and I needed to invest in a camera. To her credit, she didn’t try to sell me the most expensive camera. She recommended the Canon Rebel T3i. A perfect starter camera. The camera body, kit lens and one additional lens would be just over $800 out the door. Yikes!


Facing Fear

When I think about being an entrepreneur, fear often makes top 3 on the list of adversaries and I am no different. I pulled out my phone to check my account balance. $800. Wow. I had just enough. Was I enough?

There was so much running through my mind! …Yesterday starting a business had sounded like a good idea. Yesterday I had been really motivated. I had gone online; purchased a domain. I had spent money on a website host for the year and had purchased business cards. I had spent $89.33 yesterday! Another $800 for something that may or may not work? Yesterday this had sounded great. Now… had I even told Blake? What would he say?… I could feel myself doing a downward spiral.

That’s when I thought back to college. While I learned so much in school, one of the most invaluable lessons I learned, didn’t happen in a classroom.


Flashback to 2012

It was my senior year of college and my time on the golf team had come to an abrupt end. Suddenly, I had a lot more downtime than anticipated and the community I’d spent the past 3 years building was shattered. It was hard and uncomfortable, but through that experience, I realized I had a choice to make.

What did I want senior year to look like?

That’s when it crossed my mind. Dance! The more I thought about it, the more excited I got. I thought dance was beautiful. It’s challenging and I wanted to try it. Granted, I had ZERO dance experience, but I decided to try out for my college dance team anyways. How hard could it be? ????

Guys. I didn’t even know what an 8 count was! (I’m so glad it was just me at the try out!) Let’s just say, it didn’t go well.

As the “try out” came to an end, I was pretty confident I hadn’t nailed it. I said good-bye to the coach. Just before walking out the door, I turned around, “I may not be the best, but if you give me a chance, I’ll work harder than anyone else on the team.”

Maybe it was my mad dance skills. Maybe it was the last thing I said to her. Either way. A week or so later she let me know I had made the team! I worked my tail off! However, in doing so, I also discovered something I absolutely love. Something I never would have known if I hadn’t taken that risk!


Making the Calls

What did I want this next chapter of my life to look like?

I could do this! It was a risk, but it was also something I’d dreamed of doing before.

Sitting in the car I pulled out my phone again. I made two calls. One to my parents. I told them what I was thinking and asked if it was wise. Then I called Blake. I told him I was starting a photography business. I had just enough to buy the camera and was he cool with that? (Though I’d basically already decided.) To his credit, a strong 5 weeks into marriage, he told me to go for it!

I walked right back into PJ’s and 20 minutes later I bought my “first” camera.


Pivot Points

Whether you’re just dreaming of a future business/hobby or already working on your side hustle. I believe in life there are pivot points, choices we make that drastically change the direction of our lives. Some of them we recognize when they happen. Once I’d purchased my camera, I was all in. It was an investment I was making in my future and I was willing to put in the work.

Other times we go through experiences that help us build muscle memory for the future. When it happened, I was devastated my time on the golf team had ended, but it gave me the opportunity to practice taking risk. Something I’m forever grateful for!

What are pivot points you’ve reached in your life? What did they teach you or how did they help you with your side hustle?

As always, I love hearing from you! If you have questions you want to see answered Behind the Lens or just questions in general, send them my way. 🙂


Till Next Time Friends,




Rachael Watson, First Wedding, Snow Storm, Rachael Watson Photography




PS. I shot my first wedding just 3 months after buying my camera at PJ’s. (And just 3 days after officially incorporating! 😀 )

I did 30 weddings my first year and I haven’t looked back since!

I LOVE shooting weddings! While I never could have imagined this is what I’d be doing, I’m so glad it is! I love working with couples, capturing the joy of their weddings and helping them with whatever else they may need. 🙂

Bonus: Photo from my first wedding. 🙂 The only time I’ve ever worn a dress to shoot a wedding and there was actually a snowstorm that morning!


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April 3, 2019






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