From Unhappy Corporate Jobs to Entrepreneurial Excellence: An Interview with Colleen Welsch

(The views and opinions expressed in this interview are those of the interviewer and interviewee and do not necessarily reflect the views and opinions of Proofread Anywhere)

In the internet space of freelance instructors and entrepreneurs, Colleen Welsch immediately jumps out as an example of genuine personality and industry transparency.

From her Youtube tutorials and TikTok FAQs to her freelance writing course and coaching services, Colleen is an internet powerhouse who manages to balance career guidance with the blunt honesty and holistic practices needed to make a mark as a successful freelance writer. 

Colleen is a breath of fresh air in the online publishing and work-from-home communities and is a joy to listen to. 

I hope that you find value and inspiration from this interview, just as I did. 

– Reyné

Meet Colleen Welsch — An Entrepreneur and Freelance Writing Coach

Reyné: Do you want to introduce a bit about yourself, your favorite hobbies, your educational experience, or any other personal information that you would like to share?

Colleen: My name is Colleen Welsch and I live in Cleveland, Ohio, in the United States. 

I’m an entrepreneur, so I have two businesses that I run. 

One is my freelance copywriting business, which I am currently in the process of turning into an agency — which is super exciting, but a lot of work. I think it’ll be worth it. 

I also have a coaching/educational business called The Freelance Writer’s Guide. In this business, I teach people how to become freelance copywriters, or if you’re already a freelance copywriter, how to upgrade your business and make it better. 

But it’s not just about freelancing. It’s also about creating a sustainable, chill business. I’m not about that grind lifestyle. I want to make it so that you have balance in your life and you work smarter, not harder — That’s what we’re all about at The Freelance Writer’s Guide. 

Outside of my businesses, I’m also a musician and music producer. So, I have music on all streaming platforms.

Colleen Welsch – Spotify

Colleen Welsch – Apple Music

Learning how to produce music is something I kind of picked up during the pandemic. I built a little studio in my house and I’ve been having a lot of fun with that.

I also am a comedian. So I do improv and sketch comedy. I’m on an improv team and it’s fun.

Finding Jobs that Accommodate Demanding Schedules

Reyné: It seems like you really are creating businesses based on what you love instead of thinking, How can I find a corporation that will actually support something that I like?

Colleen: That’s really, in my opinion, the way you have to go about it. It just reminds me of that scene in Titanic — the greatest movie of all time — when Billy Zane is like, “A real man makes his own luck.” It’s true. You have to create your own opportunities. I have never had any luck with waiting for the right opportunity to come into my lap. 

I definitely tried the corporate lifestyle for years and never found it fulfilling, never found a good fit for me. That’s not the case for everyone, but that’s been my experience. If I want a certain experience, I need to take steps to create that.

Reyné: A lot of our students and graduates are moms or retirees that have schedules or working difficulties that prevent them from being able to work in a traditional office setting. It’s so hard to find companies that are willing to work with people that don’t fit the 9-to-5 mold. 

Colleen: I’m not a mother, but I certainly have experienced that my schedule doesn’t work with the corporate schedule, because I have insomnia. So, I sleep in every day. I have to or else I won’t get enough sleep. I could never be at work at 8:30 in the morning. I’m not even awake at 8:30. So, I can certainly relate to them. 

Now I have a job where I don’t have to work until one or two in the afternoon and I’m done at five. So, that’s great. 

How She Got into Writing

Reyné: I love that. So, you mentioned that you did some work in the corporate field before. Do you want to tell me a little bit about how you kind of got into copywriting, and how you got into entrepreneurship? Are there any resources or people that guided you in this position?

Colleen: So, I was always interested in writing. My favorite movie, when I was a little kid, was Harriet the Spy and I started keeping a diary in 1997. I still keep a diary to this day and I have stacks and stacks of them. 

I have always liked writing. You know when they do career aptitude tests, like in high school? They would always say, “You’ve got to work in a creative field,” but I was never given any kind of support around that from my family because most people in my family are not that creative.

Yeah, my family members have other gifts. They’re very intelligent, but they’re not artists. So, I never got any kind of encouragement that I could pursue a creative field or that there was money in that. 

It seemed like I needed to be a doctor or a lawyer or an accountant or something. That was the only way that I was going to have stability and money. So, I just didn’t know. 

How an Accidental Double-Major Lead to the Internship of a Lifetime

When I went to college, I went to a very large university where I was just a number and I never saw an academic advisor or anything. I didn’t really know what to do, so I just took classes that I felt like taking. In the end, when I applied to graduate, they said, “Oh, you can have two degrees.” I thought, oh, how did that happen? I just took too many classes. So, I got a bachelor’s in English and another bachelor’s in anthropology with a minor in classics. 

People think that, because I have an English degree, studying English really contributed to my copywriting, but it really didn’t because I studied English literature. I have never taken a copywriting class in my life — not marketing or anything. 

Getting Her First Big Opportunity

The experience that I did get, which was really great, was an anthropology internship that I had when I was in college. I don’t even know how that happened. It was complete fate that the opportunity presented itself. I guess that kind of backtracks on what I was saying about opportunities falling into my lap. It’s been rare, but this one definitely did!

When I went in to do the interview (this is a really good origin story, I guess, that kind of created a pattern for the rest of my career so far), I made this crazy portfolio to go in for this internship and it was really uncalled for, but I just went all in on it.

The portfolio had nearly every project I’ve ever done, that was cool, in my life. I brought in these t-shirts that I made for the marching band and this anthropology project I did based on Hot or Not, if you remember that website. I brought in all these interesting projects that I had done, even if they weren’t completely relevant, just to say, “I do stuff. I can finish projects. I have good ideas.” They were blown away. 

It was supposed to be a summer internship, but I worked there part-time for two and a half years. Instead of it just being an internship, I worked at the advertising agency three days a week and I went to college two days a week. 

But, I didn’t do copywriting there, either. I was an ethnographic researcher, but I was still in an advertising agency environment, and talking to people who were copywriters. So I knew that it existed, but I never thought about doing it. 

Her First Corporate Job

After I graduated, I started working in fashion retail. I worked in e-commerce. 

Side note — I’ve always had a blog. Not always. I had a blog starting in 2009. I’ve always been on the Internet. I always really liked the Internet — made my first website when I was like in sixth grade. I was just into it. 

So, I started working on an e-commerce site. I was an assistant merchant. I hated it. I hated it. I was at the lowest point of my life, or one of them.

The director of the website just saw something in me and took me to lunch one day and was basically like, what is your problem? Not in those words, but I’m sure that’s what she meant and I just said, “I’m unhappy. I don’t like this work. It’s too much math. I’m more creative. Like, it’s just not a good fit.” So she said, “Okay, we’re going to move you to more of a copywriting role.” 

So, that’s where that started. It was the simplest stuff, though. It was very basic product copy. I just uploaded products to the website and then said — this was for Justice, by the way, the little girl’s store —

Reyné: No way. I loved that store. 

Colleen: — Yeah. I would just write, “unicorn, necklace, glitter.” It was like the simplest copy, but it was still practice. That kind of got me into copywriting, although I was more in digital merchandising at that point, and then kind of moved into just digital marketing over the course of a couple of jobs.

Finding Opportunities within Inefficient Systems

At the last job I had, they had a blog on their website and my boss knew that I had my own blog and she asked, “Do you want to write this? Nobody else wants to do it. Nobody has time for this.” So I said yes and I really liked doing that. 

Then I kind of realized that there must be so many other businesses out there that have these blogs on their websites, and nobody on their team — on the marketing team — can update it because marketing teams are very busy. Also, long-form copy isn’t a skill that people on marketing teams usually have. Even traditional copywriters don’t do long-form copy. So that’s something that gets outsourced, and I knew that from working in marketing and from working at an advertising agency. 

So, I just started emailing people that had a blog on their website that wasn’t updated and I just stuck to things I knew about. I knew about beauty and I knew about fashion. So, I only emailed those kinds of businesses. That’s how I started building my career. 

Resources and People that Shaped Her Career

As far as resources for how to do the business part of it, my then-roommate hooked me up with a couple of people that she knew through networking who had their own businesses in a similar field. She connected me with another beauty copywriter, who was a freelancer, who’d been doing it for like 30 years or something. We had a really great conversation and she gave me a lot of tips. 

Probably the best tip was that I was charging way too little because I was only charging $35 an hour at the time. She said that I needed to charge at least twice that because, when you’re a freelancer, you are in charge of buying your own health insurance and paying your own taxes, including self-employment tax. You’re also in charge of your own retirement accounts and stuff. So you’ve got to double it. Whatever you think you can make, you should ask for more. 

Another thing that she taught me was that, if you have a low price tag, businesses are going to assume that you’re not good. Having a more expensive rate creates the idea that your work is going to be better. Now, will your work actually be better? That’s up to you to level yourself up. It’s up to you to make yourself a copywriter that charges $200 an hour. You don’t wait for someone to tell you that you can charge that much.

She kind of reframed that for me, because I just had that money mentality that I had to work really hard and grind and that’s the only way to make good money and support myself. I didn’t think I deserved to charge $200 an hour because I just couldn’t conceptualize it. 

Another person that my roommate connected me with owned his own marketing agency and he recommended a book called Book Yourself Solid by Michael Port. I read that whole book, and I just started doing anything that resonated with me from that book… I also learned a lot from reading Elna Cain’s blog on freelance writing, and then Jorden Makelle’s Writing Revolt. I don’t know if that’s still active [our team checked, and these resources are active at the time of this interview], but I learned a lot of stuff from those blogs too. 

How Entrepreneurs Require Specific Skills

When you are building a business like this, it’s not just following a plan that somebody else has laid out step by step. That might work for some people, but that doesn’t work for me. I learned from a lot of resources, and then took notes on everything that resonated with me — stuff I felt like actually doing. I’m not going to do stuff I don’t feel like doing, you know? 

Then I just made a plan, put it in order, and then just executed it — step by step. 

What do I need to do?

What are the daily tasks that need to happen?

What needs to happen weekly?

What needs to happen monthly?

What are the other tasks, like the one-off tasks I need to complete?

Then you just build a plan and just do it.

That’s how I started my business.

Embracing Change and Improvement

Reyné: I feel like you’ve already kind of covered something similar to this, but is there anything specific that this career has taught you — the most important thing?

Colleen: Not even that change is always possible, but change is always constant. 

There are always going to be changes happening in your business, but you will also always be changing and keeping on top of that and just embracing it. I’m always trying to improve my business.

I’m always trying to improve the way I set up my day. I have reorganized my schedule and how I track what I’m doing and my productivity methods countless times. I’m always optimizing.

Besides that, I’m always working on myself because, being an entrepreneur, being a freelancer — if you’re a freelancer, you are an entrepreneur — part of your business is your brain. So you have to always be working on yourself, finding new paradigms, mentally. It’s even exploring spirituality and therapy. 

It’s about what you can do to improve your mental game, to make sure that you can show up the best you can for yourself, and for your own business. 

Reyné: That’s super holistic. I love that. 

Colleen: Absolutely. It is. 

It all ties into one thing because I’ve noticed that, depending on what I eat, it affects how my business goes, or when I work out and how I work out. It all goes into the same thing.

Reyné: Yeah, it makes sense. It’s not the way that we traditionally view work, but it’s absolutely how we should view work.

Colleen: It is and traditionally, you check all your personal stuff at the door and then you go to work. You’re just like a zombie — you have no feelings or physical needs or anything. Then when you leave, you can deal with that stuff. I don’t believe in that at all. 

The Benefits of Freelance

Reyné: You mentioned a little bit about working around insomnia and working around your values. Are there any other benefits that you feel freelance writing and being an entrepreneur provides to you that a traditional career wouldn’t?

Yeah. Well, there are two, maybe three, main benefits.

One is motivation.

I was never motivated at any job I had, because I was always working towards someone else’s dream. It’s not my dream. Justice wasn’t my dream. It was Les Wexner’s dream, and he’s a creep. I was just putting money into rich people’s pockets, whose values I didn’t align with. 

That wasn’t the case at every place that I worked at, but some were worse than others — just really bad people running it which is not very motivating. 

You also feel like you’re selling people crap they don’t need, that’s hurting the environment — And who knows what’s happening in the factories. 

I can be more intentional now about the types of brands that I work with. Even if I don’t like the CEO or something, at least I like the team that I’m working with, or I feel like it’s a good product, or I am charging enough to feel fine about it.

Another thing is, as a freelancer, you can make a lot more per hour than in a traditional nine-to-five work environment.

In my experience, when I was working in an office, I worked for two hours a day, maximum, and then I was just there for the rest of the day. Maybe I would be in a meeting, talking to my friends, or just online shopping or something but I wasn’t actually working.

Now if I work two or three hours a day, I’ve worked the same amount but then, when that’s done, I can go do something else, which is nice.

I don’t have to be at the office, but I still make the same amount of money. So I have more time to myself, and make the same amount of money. 

That leads to the third benefit, which is that I have time for hobbies, which I never really had before. 

I prefer this format because this is what people did for thousands of years when people had specialties. They got paid to do that one thing. They just sold their services, whether you were a blacksmith or a basket weaver. You just did that thing, you got paid, and you didn’t have to go into an office for eight to ten hours a day.

Who Would Make a Great Freelance Copywriter?

Reyné: Since you also teach people how to freelance and do copywriting, I wanted to ask: Are there people that are better suited for freelancing and copywriting, as opposed to people that probably shouldn’t consider it, in your experience? 

Colleen: Yeah. There’s definitely a certain personality type that I think thrives in this environment more. It’s not for everybody. 

As you can probably tell from everything I’ve said so far, I’m a person who doesn’t deal well with authority. I’m not a follower. I’m a leader or a lone wolf. I just don’t like having a boss. 

I think anyone who feels that way would do very well as a copywriter. Some people say that if you’re a freelancer then you have multiple bosses, but you can set up the boundaries so much better when you’re a freelancer. You’re really in charge of that, but you do need to have a certain amount of independence and grit. You can’t just throw in the towel easily because there are going to be trying circumstances.

There are going to be difficult months, especially in the beginning getting set up. You really have to have grit and just remember why you’re doing this and keep going. 

How to Learn and Find Resources

I think you do have to be a self-starter — which I hate that phrase because it’s on every job application — but you have to be a person who, when encountering a problem, can google how to fix it and then go fix it instead of just giving up or relying on someone to tell you what to do. 

I have had a lot of people, like a lot of people, just ask me the same questions over and over again. This is on my YouTube channel. I’ve done 100 TikToks on this. I have a playlist of FAQs on TikTok. It’s there. People will ask, “What’s your advice for someone starting out?” That’s what my whole channel is.

It’s great to ask questions and stuff, but ask questions after you’ve done some research.

I am grateful for everybody who watches my content and asks questions, but I do feel like, in order to succeed as an entrepreneur, you’re not always going to be able to ask people. This is not something that would happen at work or at school where you always have guidance. 

When you’re an entrepreneur, you don’t always have guidance. You just have to figure it out by yourself.

I also think that learning to figure out stuff yourself is a learnable skill. I wasn’t always like that. You can learn that. Once you learn something small — from YouTube or something — and do it, and then you believe that you can do anything. It’s just on YouTube. Just learn how to do it.

If, at First, You Don’t Succeed

Reyné: Along with having hard times: I feel like a lot of people that start out, especially in freelance or a self-directed career, have a hard time dealing with criticism at the beginning because their confidence isn’t that high yet. Are there any times that you felt like your confidence was hit or like things went really poorly?

Colleen: Yeah. Things definitely went poorly. That’s for sure.

I used to be really, exceptionally bad with money. I just didn’t know anything about money at all. 

I have never been a big math person and I never learned about budgeting or how credit cards worked. I didn’t learn any of that stuff. I didn’t know how it worked. 

I failed at freelancing twice before I made it happen on the third try, so I can definitely relate to that.

The first two times I failed, it was because I just didn’t have a plan and I didn’t believe in myself enough to go for it. 

Part of it was because I had a drinking problem, too. I just didn’t have the time or the focus to sit down and work because I was always hungover. So, that was a big issue.

The third time when I did make freelancing work, I almost didn’t. I ran out of money really fast because I didn’t know how much to save or how to budget or how to even figure out how much I should save. 

I ran out of money so fast that I had to move in with my parents. I was incredibly privileged to even have that option. 

That did give me some courage during that period of my life because I thought, the worst thing that could happen is that I have to move in with my parents — and it happened.

Taking Chances and Chasing Dreams

I did one crazy thing before I started freelancing that kind of made everybody in my life shut up about the freelancing thing. I moved to LA when I was 25 and I had $3,000, no job, and no apartment. I just like put all my stuff in my car and then my mom and I drove out there.

I slept on my cousin’s couch for a couple of weeks until I got an apartment and I just moved in with a friend I barely knew and who had just moved to LA too. 

Everything turned out fine. I got a job. We got an apartment. There were some trying times while I was there but I figured it out and I think that gave my parents some confidence in me. But they have also always said that I could do anything I want.

… Everybody else in my family doesn’t understand me and what I’m doing anyways. So, that’s fine. 

Reyné: Thanksgiving is only once a year. It’s fine. 

— Both laugh — 

The Final Spark that Lead to Success

Reyné: I think a lot of people look to successful people and think that it’s never been hard for them. They’ve always done well. Look at them, they’re perfect. But, I think it’s great to realize that everyone is not great at the beginning, and sometimes not great all the time.

Colleen: I would say what made the biggest difference on my third try was that I was really clear about my “why.” 

I knew why I was doing this and I wasn’t going to quit because I wasn’t going to give up. 

Part of it was desperation. I was very depressed and I had significant alcoholism problems at the time. 

What changed everything for me was visiting China. I’d never really been outside of the US before besides Canada — barely counts, in my opinion. I thought, Oh my god there’s this whole world out here and I want to go see more of it.

I knew that I really wanted to become a digital nomad. So, I needed to transition into freelancing. I needed to make this much per month in order to make that happen and I had a timeline for myself because I actually knew I was going to get laid off.

So, I saved money, did a bunch of research, made a plan, and that was what really made a difference for me — just knowing why I was going to do it.

Once I moved in with my parents, who live in Ohio, I knew that I couldn’t give up on this, so I just did it.

Being Vulnerable and Honest About Imperfection

Reyné: I really appreciate you being so raw and open and honest about this, because I feel like, especially in the influencer space or the social media space, there is a lot of skimming over issues or avoiding them — especially eating disorders, especially drug problems, especially drinking problems — because people don’t want to make it seem like they’re not perfect. If they have issues that everyone has, then it might affect their business, but I really appreciate you being so real.

Colleen: Yeah, I mean, definitely keep in anything about having a drinking problem because I think that is an important part of the story. 

I always thought that I couldn’t have a drinking problem. I didn’t drink that much compared to other people I know and definitely not intervention-levels of drinking. I wasn’t drinking a gallon of vodka a day and laying on a mattress on the floor. I had a job and stuff, but if you feel like you have a problem, you probably do have a problem.

Even if you drink less than other people you know and they don’t have a problem, it’s personal. It’s not about how much you’re actually drinking.

Also, I’m not a drug counselor. That’s just my experience.

I’ve also read a lot of books on drinking and if your readers are curious about that subject, I would say Quit Like a Woman by Holly Whitaker is a really good resource, not just for women — anyone can read it. 

That book completely changed my perspective on alcohol in general and now I’ll never drink again, because I feel like alcohol is a tool that “the man” uses to keep us down. I’ll never drink again. There’s no point to it.

I just wish someone would have said to me, when I was younger, “You don’t have to drink.”

That never occurred to me until I started seeing a therapist when I was 30.

Everyone should go to therapy. Even if you feel like you don’t have a problem, go to therapy — there’s probably something. There’s always something. I didn’t think I had any problems and oh, lord, I did.

Salary Estimates for Freelance Copywriters

Reyné: Do you have an estimate of what you think people would make in this job or an example that we can give people that might be interested? It doesn’t have to be your salary.

Colleen: I mean, as with anything, it’s what you make it.

If you think that all you’re worth is $0.01 a word, that’s all you’re going to make. It has a lot to do with your money mindset. 

Whatever experience you choose to have, that’s what you’re going to have, but I think it is helpful to know that there are people who make six figures in this field. There are people that make multiple six figures in this field.

I, personally, don’t make that much. I make between $6,000 to $8,000 a month but, as I said, I work for two or three hours a day.

So that’s my choice.

I could work more and I could probably make more money, honestly. That’s something that is a block that I’m up against — feeling like I can’t make more than $8,000 a month as a copywriter.

I know I could and that’s what I’m trying to figure out now.

That’s what I’m researching and making a plan and going for next. 

Where to Find More from Colleen Welsch (and Free Resources)

Reyné: Is there anything else that you want to throw in there — anything that we should know?

Colleen: Well, I have tons and tons of free content on my website, on my YouTube channel, and on TikTok. 

On my website, I also have some freebies, like a cold pitch kit. As I mentioned before, that’s how I started my business — cold pitching. 

So, I have the templates that I used to launch my business and the tracker that I used to track all the people that I was cold pitching to so I didn’t forget who they were or pitch them twice.

That is all available for free on my website, The Freelance Writer’s Guide.

I also have some digital products on there, like how to get started as a freelance copywriter.

I have an SEO workshop. I have a service menu template.

Those are all on my website and they’re all less than $40.

I have a course called The Freelance Writers Guide to the Galaxy, which is a self-guided course, step by step (Proofread Anywhere readers can get 20% off when you use the code “PROOFREAD” at checkout). You can learn what you need to do to be a freelance writer based on my experiments and trying to freelance. As part of the course, we have a monthly office hours call and anybody can sign up and ask questions. You can also submit your portfolio for review. The call is on Wednesday evenings once a month.

I have a one-on-one coaching program called Six Weeks to Launch, where I will help you and tell you what to do to be successful. There’s accountability, so I’ll check over everything that you’re doing, edit your portfolio pieces, and guide you along to get you to that place where you are ready to freelance and ready to have clients.

Also, you should stream my music on Spotify or Apple Music and, if you live in the Cleveland area, come to one of my improv shows!

Reyné: Thank you so much for this. You’ve been really fun to listen to. I feel like I also got a lot of great advice from this.

Coleen: Well, thank you.

Thanks for asking me and thanks for giving me the opportunity to just go off on a really long tangent.

Reyné: I enjoyed every minute of it.

Find Out More

If you want more information about Colleen or her business, you can follow her on Instagram:

The Freelance Writer’s Guide – Instagram

Colleen From The Internet – Instagram