The question that changed my career. (Plus, the top 3 reader-favorite issues!)
Published about 1 month ago • 3 min read
Hey, Friend,
I've noticed there are quite a few new readers here these days.
And if that's you, welcome❤️
I'm so glad you're here.
Hi, I'm Allison, creator of this newsletter.
Throwback photo to 2022, when I first started writing online on my small Chromebook
You may know me as the person who talks about LinkedIn, personal branding, content strategy, and occasionally reminds you not to obsess over the algorithm.
But you may not know much about the person behind these words.
So today, I thought I'd share a little bit about the story behind The Content Cup and how I ended up doing this work.
I've been sending this newsletter for about two and a half years now, and I still catch myself having moments where I think, "Wow...I GET to do this."
This path wasn't something I mapped out at all.
The Content Cup actually started as a newsletter called The Organic Freelancer, and it focused heavily on SEO content. (Many thanks to those who have stuck with me from those early days!) At the time, that was the work I was immersed in, so naturally, that's what I wrote about.
But as my business evolved, so did my interests. I found myself having more conversations about LinkedIn, visibility, personal branding, relationships, and how opportunities are often created long before they're ever offered.
The name changed, but the goal has always stayed the same. Provide value...and create something that might fill your cup before the weekend:)
Prior To This Creator Life
Before all this, for fifteen years, I worked in corporate digital marketing.
Last day in the office, July 2021.
I enjoyed the work, learned from some incredibly smart people, and built a career I'm still proud of. There wasn't a dramatic breaking point or some terrible experience that pushed me to put in my two weeks.
The reality was much simpler.
My kids were getting older, and I wanted to be home during the summers and there when the bus dropped them off. Overall, I wanted more flexibility with my professional life that played nicer with motherhood.
I had no idea what I was building...or that I was building anything. In fact, I can remember telling myself I would just find another 9-5. But one question kept coming back to me...
Is the 9-5 really the only path, or is there another option?
Discovering By Doing
That question led me to exploring and leaning into writing. Throughout 2022, I published more than 400 articles on Medium.com.
The opportunity gave me the courage to practice in public and become more confident in sharing my thoughts online. I made a little, but it was never going to cover what I needed financially.
But then LinkedIn came back into the picture.
I started sharing what I knew about content and SEO, and within a few months, I landed my first two retainer clients.
It was my "aha" moment that maybe... just maybe... the 9-5 didn't have to be the only way to financially support my family.
Then my SEO clients started asking me another question...
"Can you help me do what you're doing on LinkedIn?"
And that's really how this business began. Not because I crafted a perfect plan. But because I learned that when people consistently see your ideas, they start to connect with you, and keep you top-of-mind.
That's true whether you're building a business, looking for your next opportunity, or simply trying to establish credibility in your field.
Today, I spend my time helping leaders and companies do exactly that.
But some of the opportunities I've enjoyed most weren't even on my radar when I decided to leave that corporate role of mine...
Teaching...for one.
Teaching content creation and digital marketing through Denison Edge at Denison University.
And speaking.
Speaking to 100 founders about how to build your brand and business on LinkedIn.
Neither one was part of what I envisioned.
In fact, if you had told Corporate Allison that she'd one day be standing in front of rooms talking about LinkedIn and personal branding, she probably would've laughed. I definitely would have looked at you with skepticism.
But those opportunities appeared gradually through relationships, conversations, introductions, and simply continuing to show up.
That's probably one of the biggest surprises from the last few years.
The opportunities that changed my life happened because, when you boil it down, it always comes back to the people... surrounding yourself with really good people. And continuing to have the drive to forge a different path that works for you.
So if you're at the beginning of your journey... maybe even in the middle... and unclear... without a plan... but just curious that maybe... just maybe... there's something else possible for you...
Lean into it.
The plan will come together. Keep those conversations going.
And let me know how I can help ❤️
In Case You Missed Them...
Here are the top 3 reader-favorite issues from the past year.