How I Freelance: Rob Swystun

How I Freelance: Rob Swystun

For Rob Swystun, one of the upsides of freelancing is the opportunity to learn about new subjects. Since launching his freelance business in 2011, his curiosity has led him to write on evolving topics like electric vehicles, robotics and sustainability.

Despite his interest in technology, Rob still sees a need for a human touch in content. Read on to learn more about how he brings this mindset to his work as a content marketing strategist, journalist and writer.

When and why did you go freelance?

I started freelancing in 2011. It made the most sense at the time; I had just left my last newsroom position and started doing freelance writing gigs while I was looking for a job. I enjoyed the freedom of being my own boss and freelancing eventually became my full-time job.

What is your niche?

I have several: content marketing strategy, B2B, electric vehicle charging, space, robotics, fintech/finance, agtech and cleantech.

How did you choose your niches?

I basically learned content marketing strategy as I progressed as a freelancer. Content marketing was in its infancy when I started, so I was able to learn by trial and error, seeing what worked and what didn’t.

Space and robotics are things I’ve been interested in as far back as I can remember, so they were natural niches for me to get into. I kind of fell into the niche of electric vehicle charging, but since I’m interested in new technologies, I wanted to pursue it as a niche as I learned more about it.

I’ve always been around agtech growing up in an agricultural community, so that one was also natural for me. And I love learning about anything to do with finance and fintech. One of my main passions is sustainability, so anything that can help the Earth recover from the current climate catastrophe is of special interest to me.

Who are your clients?

I primarily work with B2B companies interested in content marketing but don’t know how to get started or where to put their budget.

What types of projects do you work on?

Content marketing strategies, website content, articles, blog posts, white papers, case studies, guides, brochures, brand journalism, press releases, video scripts and ghostwritten books.

Where do you freelance from?

I’m in Winnipeg, Canada.

Go forth, learn and write about anything you find even remotely interesting. Just do your research first.

Tell us about two tools you rely on to run your business.

LinkedIn for cold outreach. And Google Docs for writing and sharing work.

Name one thing that’s surprised you about freelancing.

Although I’ve gotten used to it now, I was surprised at just how bad a lot of businesspeople are at communicating. People whose job it is to form relationships with customers will ghost a freelancer for no reason. It’s really quite disappointing. A lot of businesspeople are clueless when it comes to dealing with freelancers.

Made any big mistakes during your freelance journey?

Giving away my expertise when I should have been charging for it. I’m naturally a giving person, so when people ask my advice, I’m inclined just to start talking to help forge that relationship. I’ve probably given away tens of thousands of dollars’ worth of consulting when I should have been getting compensated for it.

What are you proudest of with your business?

That I’ve been able to thrive as a freelancer even though I had no idea what I was doing when I began my journey. Starting in content marketing when content marketing was just getting started has really helped me grow as a marketer alongside the entire content marketing industry.

There’s lots of advice out there for freelancers. What advice do you agree with?

Never stop learning. Whether it’s a new skill, learning how to run your business or just a subject you’re interested in, always be learning. This isn’t exclusive to freelancing; it’s also for life in general. You should always be curious and be willing to learn and grow as a person.

What common advice do you disagree with?

While I don’t disagree with the advice of “write what you know,” I don’t think it should be exclusive. Write what you know, but also write what you’re interested in. Write about stuff you have no idea about, as long as you do your research first. Write about topics you never even knew existed before (again, after doing your research).

As a human who is capable of learning, there is no reason to limit yourself to only writing about what you currently know. Go forth, learn and write about anything you find even remotely interesting. Just do your research first.

What areas of opportunities do you see for current or future freelancers?

As companies continue to get less and less human, I see the opportunities for freelancers being mostly in building those all-important human-to-human relationships with customers who are already growing weary of automation. The value we create for businesses is in building trust with customers. The businesses that understand this are going to be the ones that survive.

Leave us with some words of wisdom.

I’ve had training from some excellent tutors throughout my career, including Mandy Ellis and Adrienne Smith. One of the best things a new freelancer can do is see out help when they need it. It’s worth it to spend a little bit of money to get training from people who have been there and done what you are trying to do.

Want to connect with Rob? Find him on LinkedIn or visit his website at

How I Freelance: Melissa Ripp

How I Freelance: Melissa Ripp

Women have valuable expertise to share and stories to tell. And Melissa Ripp wants to help them tell them.

Mel – as she’s known to her friends – originally started her marketing company as a side hustle, offering marketing services for small businesses. Over time, she shifted her focus to thought leadership and content strategy for female executives and business owners who want to build on their personal and professional brands.

Read on to learn more about how freelancing helped Mel develop new skills and find a fulfilling career path.

When did you start freelancing?

I started freelancing in 2007. My company, Peapod Marketing and PR Consulting, has been a thing for 16 years now.

At the time, I was living in my hometown of Door County, Wisconsin. It’s the thumb of Wisconsin, the Door County peninsula. Funny enough, I now live here again.

Door County is a place that depends on a lot of tourism. We have 300 miles of shoreline. We also have all these lighthouses and incredible water views. Fall leaf-peepers like to come up here. It’s just a beautiful place.

I moved back home after college and got a full-time job as a marketing director for a nonprofit. I worked in nonprofits for a long time, and then my freelancing was a side hustle along that for a long time.

But what I noticed is that when people needed help with their marketing and writing, there weren’t really a lot of resources for them. Social media was just starting to become a thing, and unless you had your own creative chops, you were kind of out of luck.

I was writing arts and entertainment columns for an independent newspaper, the Peninsula Pulse. People would reach out through the Pulse and ask if I would be interested in writing for their business. They had a press release or website copy they needed. That was how I got started.

Do you freelance full-time or part-time?

Peapod has been a thing for 16 years. But I just celebrated five years of full-time freelance work in November 2023. The day after Thanksgiving in 2018 is when I officially decided to hang up my full-time shingle and become my own boss.

Before that, I had a bunch of W-2 jobs. I was a director of communication and PR for an EdTech company. I did a lot of content strategy and writing work. I got tired of saying, “One day” instead of “Day one.”

Why did you choose to pursue freelance work?

I always knew I wanted to go out on my own and run a business. Peapod was a side hustle for 11 years, and I hustled hard.

I loved how freelancing gave me new skills. I was a really early adopter of social media and started to understand webinars and lives and those trends early on. Freelancing opportunities gave me a chance to figure things out.

My full-time jobs were still toying with this idea of digital marketing. I know it sounds funny to think about that now. But in 2007, when I started, we had websites, we had Facebook, we had all this stuff – but nobody was really using social media for business yet. Having a freelance business gave me an opportunity to discover different types of work I wouldn’t have done otherwise.

The other reason? I’ve never quite fit into corporate life. There’s a reason why the first 10 years of my career were in the nonprofit world. It was a better match for the way I looked at marketing and communications. Storytelling resonated with me early on, and it felt like nonprofit and educational institutions were the same way I was.

When I moved from Door County to Chicago and then Madison, Wisconsin, I had to be part of the corporate machine because that’s where I was finding jobs. I quickly learned that I wasn’t corporate materials. I worked my way up to a director position and was managing six people. And I don’t think I was doing it that well.

I decided to pursue full-time freelance work because I thought, I can’t do this. I’m not good in a corporate setting. I’m burning myself out. I had incredibly high anxiety. I’m still an anxious person. I just need to be in the driver’s seat.

What are your niches – and how did you choose them?

I’m a thought leadership strategist and ghostwriter for women executives and entrepreneurs. I help women determine what their content themes are and how they can get their ideas, thoughts and perspectives out into the world. And I write that content for them, in their tone and voice.

This wasn’t always Peapod’s direction. I pivoted to this work in 2020/early 2021. The reason is that I’m 42 and I came up in a world that straddled both of these really interesting times to be a woman in business.

At the beginning of my career, I had situations where I wasn’t taken seriously. I was ignored. A man would say the same thing I did or present the same idea but say it a bit differently. And everyone was like, “Oh, yeah, great idea.” I got tired of feeling like my ideas and thoughts didn’t count.

I wanted to figure out a way to present my own story and my own accomplishments. I didn’t want to feel like I was waiting for somebody to tap me on the shoulder or notice me. I’m a firm believer that if you want someone to notice you, you have to do things yourself.

I also believe that anyone can be a thought leader. I think we all have stories, perspectives and expertise that can influence people to take action and make them feel they are less alone.

Take what we’re seeing on LinkedIn. There are a lot of LinkedIn influencers who say you should be doing this and you should be doing that. But there are also a lot of people who are simply leading and teaching through their experiences. That’s what I wanted to do. And that’s also what I wanted to help other women do.

Women deserve the chance to talk about what they’ve done, what they’ve learned and what it means to them in a way that can help other people. And in doing so, they can also help themselves. A lot of women, myself included, deal with confidence issues. We need to deal with it by actively and openly talking about things related to our lives or our professional careers, and I wanted to remove that stigma.

Who are the clients you work with?

My clients are leadership, executive and organizational development coaches. They’re also fractional CMOs and VPs. What they all have in common is that they’re women, and they’re either building their own incredible thing or doing great things in the corporate world.

All of my clients are incredibly busy people who understand it’s critical to have a personal brand that’s consistent and engaging. I help them discover that – and then I help them put it out into the world.

What types of projects do you work on?

I do individual and personal brand and thought leadership messaging. My clients are asking, “What am I about and how can I make sure my ideal audience knows what I’m about?” I help them decide on content themes that resonate with them and their audience.

Once we have those content themes, I help with social media posts. LinkedIn is my bread and butter. I feel that’s where I shine and also where my clients shine.

I also do a lot of long-form writing, which can be anything from blog posts and ebooks to other lead-generation sources. I do a lot of speechwriting and website copy. And PR work, helping find places where women can extend their voices beyond their own platform. Earned media opportunities. Podcast guesting. I have a pretty extensive network and that has helped me cultivate those kinds of things for my clients.

Tell us about two tools you rely on to run your business.

I would not be able to do my business without Fathom. It’s a note-taking app that integrates with Zoom. It gives me transcripts I can use to create posts and articles. It’s been a game-changer in being able to do my job more quickly.

The other tool I rely on is HubSpot. It’s not only my CRM, but it’s also where I publish my newsletter and my email welcome sequence and all those things. It’s a really great way to make sure everything is all in one place.

Name one thing that’s surprised you about freelancing.

When you surround yourself with the right people, it becomes collaboration over competition. When I first started my business full-time, fellow writers would want to book discovery calls with me trying to get some insights. And I remember thinking, “What if they steal my work?”

There are people who do the exact same thing I do. Maybe they do it for other types of people or they do more PR and less content creation and ghostwriting. I had to adopt a mindset that there’s enough work for everyone. I know right now that’s a little hard to recognize. There have been layoffs in the tech sector and a lot of my clients have said, “Oh, I’m going to start using AI.”

But when it comes to thought leadership work, there really is enough room for everyone. It’s a complete collaboration. I don’t feel there’s a competition or that I need to hide any of my intellectual property from anyone.

Having a freelance business gave me an opportunity to discover different types of work I wouldn’t have done otherwise.

Made any big mistakes during your freelance journey?

When I first started my business, I was so enthralled with the fact that I can do this thing. I can charge for this thing. That led me to take on anything and everything when it came to writing. If you needed something written, Mel was your girl. I wrote copy for B2B manufacturing sites and social media posts for a social services nonprofit and blogs about cybersecurity. The mind cannot compute all of the context-switching you have to do to work within those realms. I kept wondering why I was so exhausted every day.

I realized I loved the variety, but I couldn’t keep doing this. I hired a coach who helped me get really clear on my values and purpose and what I wanted Peapod to become. I went backward to go forward. I was able to think about what I wanted the business to be and how I didn’t just want to be an order taker. I wanted to be a strategist and a partner.

And honestly, working with that coach helped me determine I really love ghostwriting work. I stumbled upon ghostwriting by accident. It was a woman who I had done a bio for her and she asked if I would be interested in helping her craft some LinkedIn posts. I loved it, and it was because I worked with that coach that I uncovered that little nugget. Now that’s 60% of my business.

I don’t know if it was a mistake, but I moved way too much in the direction of I don’t care if I’m overworked and I don’t care if I don’t exactly like what I’m doing. I wonder what would have happened if I had worked with a coach sooner. Maybe I would have uncovered that it didn’t need to be that hard.

What are you proudest of with your business?

When I quit my job, I had six months of bill money saved up in my savings account. There was definitely a part of me that was like, “OK, here’s my six-month vacation.” I had a couple of clients in the pipeline. I knew my money was going to run out in April and I would need to look for another job. I just didn’t have a lot of self-confidence that I would be able to do this full-time.

And then I got to my one-year anniversary and then two and three. That was during COVID. I had my best year ever during COVID, which is pretty wild. Now I don’t think about what happens when my business dries up, because I don’t feel it will.

I also have a much better business development strategy than I used to. I’m not just waiting for things to come in. I don’t pretend that I’m not scared sometimes. This year has been weird, just like it was for everybody. My phone wasn’t ringing as much as I thought it would be. But I’m proud that I’ve been able to support myself and my family for five years. That’s pretty cool.

There’s lots of advice out there for freelancers. What advice do you agree with?

I’m not particularly a “woo-woo” person, but a lot of things shifted for me when I changed my mindset. I’m not saying mindset is the only reason I’m successful or that if you just change your mindset, everything will be OK. It’s a constant battle to get up every morning and say, I choose to believe I won’t have problems booking work with my ideal clients. I choose to believe there is enough work for everyone. Those things are really tough to believe because most humans aren’t wired to think that positively.

But I know mindset is a choice. It’s choosing to think differently. It’s not easy and it takes an awful lot of time. I’ve been on the other side of that equation, where I thought no one would hire me and my business would go down the tubes. My grandmother always used to say worrying is like a rocking chair: It gives you something to do, but it doesn’t get you anywhere. That’s something I think a lot about when I think about freelance work and entrepreneurship.

What common advice do you disagree with?

I don’t agree with the idea that you have to be constantly scaling and doing other things besides your craft to grow your business. The way you grow your business is to be impeccable with your word, to do things when you say you’re going to do them and to build solid relationships and become incredibly referrable.

I don’t always do a great job at that. I slip on deadlines. Sometimes I over-promise and under-deliver. It’s part of me being a perfectionist. But if you want to write for a living, you should write for a living.

Your business will sometimes have to shift, as we’ve seen with AI. But I don’t agree that for freelancers to be successful we have to be doing five different things and creating five different revenue streams.

I believe anyone can be a thought leader. We all have stories, perspectives and expertise that can influence people to take action and make them feel they are less alone.

What areas of opportunities do you see for current or future freelancers?

I think there is a perma-lancer movement that’s really interesting. A lot of companies are bringing in freelancers and having them act as an internal agency. Sometimes when you keep things in-house, a lot of innovation and ideas get missed. Having a freelance writer or designer or developer gives you a competitive edge.

The coolest thing about freelancing right now is that we are in the driver’s seat. We have the authority and the expertise. We have what it takes to be thought leaders ourselves. We have the ability to perfect our brands and get out there in a way that people can see us. They see our values and what it’s like to work with us. We have the ability to pick and choose our clients based on what’s best for us. And that part’s really cool.

Want to connect with Mel? Find her online at or connect on LinkedIn, Instagram, Facebook or Threads.