Confession: I Was a Failed Entrepreneur

We talk a lot about being authentic. I think it’s important to be open, and as a brand, to always represent yourself in a real way. This fosters connection between you and your audience, one that builds up that all-important trust—but it’s not always easy to do.

Part of being authentic is recognizing that sometimes you fail at things because as good as you are at what you do, you’re not perfect.

On a personal level, I am a failed entrepreneur…. And that’s how I know I’m exactly where I need to be today.


My Story

I wanted to be a teacher from the time I was a second grader and never once strayed from that course. I got into my first choice of college and didn’t bother applying anywhere else. While I loved college, I didn’t particularly enjoy my teaching classes and the thought of taking the teaching exam scared me.

I signed up for it. Then I slept through my alarm on the day of the test and completely missed it. I never went back.

I ended up taking extra classes on the side and graduating a year early with education as my minor instead of my major, but there wasn’t much work for someone who hadn’t passed their teaching test, so I went back to school to get another BA in Professional Writing.

Now this was my passion. It was what I was born to do—but still, I couldn’t get a job.

I started freelancing. I became valuable to small brands by expertly crafting their messaging. Then I found a mentor and learned how to be more than just a writer, but a marketer.

“We each have our own journeys, and it’s important to acknowledge our failures as much as it’s important to acknowledge our successes.”

I spent hours honing in on my messaging. Getting a logo created. Putting a website together. I reached out to some of my most successful projects and got amazing testimonials. I did research and put lists together of potential clients. My friend helped me with the outreach and I was going to hire her full time once we landed a client or two.

After reaching out to about 300 businesses and conducting a handful of sales calls, nothing happened. They loved me and knew they needed my services, but couldn’t afford it. They weren’t interested in inbound marketing, they just wanted someone to manage Adwords. The list of reasons for the rejections is endless.

I was so excited to work in this niche, but my niche didn’t want or need me.

I had to start working full time again to keep a roof over our head and food on the table. With all my energy going into making my new job successful, I didn’t have the energy or desire for the side hustle anymore. My dream of becoming an entrepreneur was dead.

For some time I even worked at another marketing agency, but it took less than six months for my ambition to get the best of me--and I was fired because the way I envisioned working with clients didn't align with the founder's vision.

Failing was my biggest win

I didn’t have what it takes to be an entrepreneur then, and that’s ok. I’m an exceptional writer (if I do say so myself) and my creative strategies have helped a lot of brands push their operations to a new level.

My “dream” of being an entrepreneur was less about running my own business as it was about having a job that I loved, one in which I had more control over my growth and success.

If that venture hadn’t failed, I’d probably still be writing blog posts for that company. 

If that work at the agency had worked out, there wouldn’t be this blog…. Then where would YOU be?

The value our failures bring

It’s all over the internet in bright fonts and a confident, yet braggy tone….

“I made $100,000 blogging, and so can you!”

“My coaching business brings in one million dollars a year. Take my course to learn how you can attract high-paying clients just like I did.”

“Want to scale your fitness business and leave your full time job like I did? My 127-step course will show you how.”

None of this is helpful. Whether it’s two steps or 500, there’s no magic formula for getting to where you need to go. It’s our failures in business that define us and teach us how to make the right adjustments to move onward.

“The ultimate goal should never be “to succeed”. We all fail, that’s how we learn. When we learn, we grow. When we grow, we are successful.”

It’s ok to fail. Sometimes, it’s encouraged. Whether, like me, you’ve failed at being an entrepreneur, or you simply tried a new strategy and it didn’t pan out, failure is ultimately what you need to help you get ahead.

Don’t be scared of it. Embrace it. Without a little (or a lot) of failure, you’ll never reach your full potential.

Shauna Armitage.png

Meet the Author: Shauna Armitage

Shauna is a Marketing Director or Fractional CMO helping early-stage startups scale with effective strategies, creative solutions, and unparalleled integrity by making the most of small budgets for maximum impact.

As a vocal advocate for women in business, Shauna is on a mission to redefine what it looks like to be a working woman and to support other women doing the same. She spends her free time traveling with her husband and four kids while drinking Coca-Colas. Connect with her on Instagram at @shauna.armitage.

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