Stride Stories: Content marketing expert finds flexibility and freedom


Emma Siemasko is the owner of Stories by Emma, a copywriting and content marketing consulting business.

Emma, tell us about your background!

Emma: I’ve been running Stories by Emma, my own company, for the last two and a half years. I serve clients in the tech space where I help businesses with all their marketing efforts, particularly in editorial. Basically, if they need blog posts written, emails written, customer stories written, I guide them and provide help from the ground up.

What were you doing before that?

Emma: I worked in-house at a small, growing tech company. I was there for almost three years and I managed their content marketing. They were later acquired by a larger company. I realized that working for a big company wasn’t what I wanted to do. I wanted to be more in the driver’s seat than anything else.

So I decided to go off on my own. I’d been doing a bit of freelance work on the side, so I wouldn’t say I was jumping off a cliff into the complete unknown. I had an idea that starting my own company was a realistic possibility.

How did you make your plan financially?

Emma: I definitely didn’t have it all figured out, but I did have a few things I knew for sure.

When I’d worked in house, I hired a lot of freelance writers and I knew what we paid them. I knew that these freelance writers seemed to be in a good position financially and weren’t struggling to pay their rent. Because I had exposure to those numbers, I was confident that the field itself was viable.

So when I first started my business, I made a budget of all my basic living expenses. I focused on the nuts and bolts such as rent, auto-maintenance, and insurance. My goal was to hit that budget right off the bat. I decided I’d spend 6 months trying to make it work before deciding whether it made more sense to go back to a traditional job.. Fortunately, in the first month I’d hit my target budget. It was great, because from there the business just kept growing.

In those first 6 months, what would you say were your biggest hurdles?

Emma: Will I make enough money? Can I cover my expenses? Those were big hurdles. Not to mention the accounting and taxes. And finally, will my health insurance cover me adequately? Those were my biggest concerns. I had concerns too that were more of “Can I find clients?” and “Will this be a sustainable business?” Those were in a separate category though. I knew I was good enough to do this. I knew I had the skills to work on this. But the lifestyle hurdles were scarier.

Are there any struggles or challenges you still face?

Emma: Yes, of course! It’s still tough to decide the best way to spend slow time. I ask myself if I should work on the business side or if I should go out and network. If I have 2 slow months it’s not a big deal, but if I was having a slow consecutive 4 months, I’d definitely have to start doing something differently.

The other challenge is that I’m pretty extroverted, and it’s been difficult to work without any co-workers. I have wonderful clients who I talk with all the time, but I don’t work with people constantly as one does in an office. Instead, I work from home and that presents its own issues. It’s like anything else though; it’s so easy to think of how the grass looks greener on the other side. Even though I wish I had co-workers at times, I love working from home and all the flexibility it provides. I’ve noticed that self-employment is very nuanced with what’s great and what’s not so great. Often times they’re the same thing.

What's your favorite thing about being self-employed?

Emma: I’d say the flexibility and control. I absolutely love having the flexibility. Even though it’s a double-edged sword, the lifestyle I have now is pretty amazing. I can choose how much time I want to put into my business, and I can work on the aspects I think are important with clients I like.

Also, I find it to be very fast paced. I don’t have to wait for things to get approved by a legal or compliance team, which is super common in writing for big companies. I can move at my own pace and get things done on my own time. While I’ve considered going back to in-house because of what I miss out on, giving up my freedom and flexibility would be extremely tough. I just feel like I’m gaining so much from it right now.

Do you think you’ll always be self-employed?

I realized that working for a big company wasn’t what I wanted to do. I wanted to be more in the driver’s seat than anything else.
— Emma Siemasko

Emma: I’m not sure. I think that I have the personality type where it’s very likely that I’ll continue to work for myself and continue to find different ways to work for myself. Will it be in this exact capacity? I can’t say.

It’s possible that I’ll go back to a traditional job to grow my skill set. I’m still young, and there’s a lot to be learned from working with other people. For now though, I’m staying self-employed, and I imagine I’ll be self-employed for awhile into the future.

Photography by Ashlee Morgan at Matthew Morgan Photography