My Story: From 9-5 to Owning a Business I Love

I’ll just come out and say it: I didn’t start my business the conventional way. Most people would advise you to save six months of expenses, build a robust portfolio and get all of your ducks in a row before even contemplating leaving a stable 9-5 to start a business. Now, I’m not arguing that advice as it is definitely the wise way to do it, but that just didn’t work for me.

Where it all began

Let’s take it back to 2017. I had been working a 9-5 for over a year when the nagging feeling kept coming up that this couldn’t be it, there had to be more. I couldn’t fathom another decade, let alone four, of unfulfilling work and minimal pay increases.

I had started a side hustle with a friend in 2016 that had planted the seed of entrepreneurship. I just kept thinking how much I would rather use my brain to build my dream instead of someone else’s.

I would binge How I Built This at work and daydream about owning a thriving business. Every night before going to bed I would look at the quote on my wall from Warren Miller, “If you don’t do it this year, you’ll be one year older when you do.” and I knew that I had to make a change.

However, I also knew that as much as I loved working on this side business, it was months (and a lot of work) away from making us money. So, I made a plan to help other people build their websites while we got our business off the ground.

Here is where it probably would’ve been wise to commit to six more months of the 9-5 while building out my freelance portfolio further, but I’m one of those “trial by fire” people. Instead of taking the logical path, I decided to fall back on my years of babysitting for an income while I built my portfolio.

The big leap

At 23, I quit my 9-5 and left it for an interim income made by wiping kid’s bottoms and questioning my decisions.

I committed to myself that by April 2018, I would solely be making money through freelance design work. When March came around and I had only built two brands and websites for free and had yet to build my own, I knew I needed to kick it into gear. I had so much fear and doubt looming about this next shift. However, I knew my time of playing in the mountains and having minimal responsibility for the first time in my life was up. It was time to prove what I could build.

The second leap

On April 3, 2018 I filed for my LLC and invested in a career coach. In the first week of owning my business, I got five clients and I was ecstatic. It was really happening.

I got my start as a designer on Upwork. I love their platform and still find amazing clients on it today and it was also an integral part of my start as it allowed me to build a robust portfolio in three months.

The ups and downs

None of this is to say it’s just been easy. There have been moments of doubt, confusion and questioning what I truly want out of this business after putting so much into it. People aren’t kidding when they say your business becomes your baby.  However, I wouldn’t trade it for anything.

Two years and a lot of lessons later, I’ve been able to create a comfortable income helping people bring the vision of their business to life. It’s incredibly rewarding and I get to use my creativity every day to build my dream and help other people do the same.

There are so many different ways to start a business and a plethora of articles and resources that will advise one path or another. However, just remember this is your journey and you get to do it in whatever way works best for you. And if that includes a couple of detours along the way, that’s okay.

The most important thing is to just start. Because if you don’t do it this year, you’ll be one year older when you do.

I’d love to hear your story of getting started. Drop a comment below if you took an unconventional path or if you have any questions about mine!

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  1. Michela Torczon says:

    This is so speaking to my heart!!! I am incredibly glad that I found you, and your story is definitely inspiring me right now (I’m currently in that back to babysitting phase haha). Not sure quite yet how I’ll need you, but I definitely will let you know when I figure it out. Thank you for sharing your wisdom and helping others!

    • Sydney Smith says:

      Yay! Babysitting was such a great way for me to transition and have flexibility. We’d love to have you in the Pinot and Power Moves facebook group, it’s filled with other badass women and we are always sharing value and tips and tricks! Also always happy to do a virtual coffee if you want to connect 1:1 just to chat about your journey, you’re at such a fun stage of it!

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