Interview With Caitlin Pyle From Proofread Anywhere

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I recently interview Caitlin Pyle from Proofread Anywhere. She’s been proofreading since 2007 and also teaches other how they can start a successful Proofreading Business though her course General Proofreading: Theory And Practice.

You can find her on her website, Instagram , Pinterest , Facebook and Twitter .

Interview With Caitlin Pyle From Proofread Anywhere
Interview With Caitlin Pyle From Proofread Anywhere

Can you tell me a bit about yourself?

My name is Caitlin Pyle! After working as a freelance proofreader, I now teach others how to learn marketable skills they can use as they start their own businesses. I became a multimillionaire in four years and have been featured in publications such as, Business Insider, Fast Company, and more. I live in Florida and want all people to know that living the life you want is possible for anyone willing to do what it takes to get there.

  1. How many hours a day do you work on average?

My business started with me working 16-hour days on my blog and today I’m semi-retired while my team of 8 runs much of the day-to-day. I love having the freedom to still help people without having to work all the time.

  1. Can you describe/outline your typical day?

The great thing about working from home and running your own business is your typical day can be anything but typical! I get to decide what my typical day looks like and it’s always different. How’s that for freedom and flexibility?

  1. Why did you become a proofreader?

My passion for proofreading started when I studied abroad in Germany for a year in college and would help students proofread their college essays. I loved using my grammar talent to catch errors and help others turn their writing into masterpieces.

That love for proofreading continued to grow. I took my general proofreading skills to the next level when I got into proofreading transcripts for court reporters back in 2012. I was so good at spotting errors, I became known as “Eagle Eyes.” In fact, proofreading transcripts became my primary source of income in 2012, 2013, and 2014.

  1. When and Why did you quit your job?

I actually didn’t quit my job; I was brutally fired from the office job I had. It turned out to be one of my best moments too, because that was what led me to writing my proofreading eBook, which led to my proofreading courses, and the rest is history. If I wasn’t fired, I wouldn’t have been forced to look at other options, and I wouldn’t be helping the people I am helping today. 

  1. How has being an entrepreneur affected your family life?

My family life has actually affected my entrepreneur life. I went through a messy divorce which led me to step back from my business for a while. Since the beginning, I’ve hired people who have been able to act on my behalf. It has been invaluable to have the right people on my team so I can have the freedom to step back when I need to.

  1. What motivates you?

The freedom to live the life I want is a huge motivator. I don’t ever want to go back to an office job or to have to work for a boss I don’t respect. I get to make my own hours and decide what my life looks like with the freedom I have created for myself. 

  1. How do you generate new ideas?

When a new business grows, you can’t help but grow along with it. If you’re not moving forward, you’re moving backward so new ideas will be a natural by-product of business growth.

  1. What is your greatest fear, and how do you manage fear?

No matter how successful you become or how much money you make, there will always be the fear that you’re going to fail. Fail is an F word in my book and it creeps itself into my head from time to time. However, what I’ve learned is if you choose to live in fear or let your doubts control your actions, you will never move forward. What we believe about ourselves and what we can achieve is so important! One thing I remind myself of daily is that It’s okay to get scared. There are some steps I have had to take in my career and even changes that I have made that have been crazy scary! It’s easy for us to think that if it’s scary that maybe that means it’s not meant to happen. But everybody feels scared about something and we can’t let it hold us back! It’s okay to be scared, but it’s not okay to let it dictate my decisions.

  1. How do you define success?

Success is different for everyone. For me, success is finding your own path that works for you. It may mean how much money you make or the hours you have to work or even the type of career you have. Because we’re all different, we all get to decide what our own definition of success is 🙂

  1. Do you believe there is some sort of pattern or formula to becoming a successful entrepreneur?

That’s the beauty of it — not at all! My only advice would be to take the focus off yourself and put it on solving problems. Not only will it take a huge burden off you, but it’ll also help you reach more people by genuinely caring about them and solving their problems. 

  1. What business-related book has inspired you the most?

There are so many books I love, but a current favorite is The Big Leap by Gay Hendricks. It helped me break past my barriers. My favorite quote: “It is never too late and you are never too old to create the life you want.” 

  1. What is the part of your favorite aspect of being an entrepreneur?

I love the flexibility! I am no longer chained to a desk, working to help pay for a boss’ Escalade. Instead I have been able to make my own schedule, work in my pajamas if I want, spend more time with those I love, and structure my job around my life–not the other way around! 

  1. What has been your most satisfying moment in business?

I think one of the best moments was and still is when people write in and tell me how my course or one of my books has changed their life or shifted their perspective. Another great moment was making my first 100k online. I was really skeptical going into this — I thought, “Are there that many people who want to learn to proofread?” Turns out there is! 

  1. What piece of advice would you give to college graduates who want to become entrepreneurs?

The biggest thing I could share is to get out of your own head and focus on who you are helping instead of your own problems. I know it’s kind of difficult if you’re drowning, so the first thing would be to stop drowning and then focus on solving problems. And I would give this advice to anyone! 🙂

  1. If you had the chance to start your career over again, what would you do differently?

I would have started working with Julie Stoian sooner. She’s an incredible mentor, friend, and expert in her field. 

  1. What would you say are the top three skills needed to be a successful entrepreneur?

I struggle to answer this because there is no easy three-step process to becoming successful. Talk to other entrepreneurs and you’ll find out all our stories and journeys are so different from each other. For someone just getting started, though, I would tell them to ask themselves these questions: 

  • What skills do you already have?
  • What skills are you interested in attaining?
  • What are you passionate or excited about?
  • Who would you like to help with your skills or what skills would you need to help people?

Think very slowly and carefully through these and see what you come up with. Don’t be afraid to be creative or goofy about your answers either. You never know what may end up inspiring you toward your next step 🙂

  1. What entrepreneurial tricks have you discovered to keep you focused and productive in your day-to-day busy schedule?

I have 3 tips that help me stay productive:

  • Make a list! If you don’t have a plan for what you’re going to do that day, you’ll find yourself investing your time in things that are huge time wasters.
  • Have realistic expectations. Deciding you’re going to get something done in an unreasonable amount of time is only setting yourself up for failure. Make sure to be realistic with your timelines.
  • Set a schedule that works for you. Some people are better at focusing at night while others are morning people. Do what works for you.
  1. What key activities would you recommend entrepreneurs to invest their time in?

Reading books about the financial system and the tax system so they can understand their business better — especially as it grows. My two favorites on those subjects right now are Fake by Robert Kiyosaki and Tax-Free Wealth by Tom Wheelwright. A lot of people will tell you if you get your business set up right in the beginning that it’ll be easier in the long run… and they’re right. Thing is, when most entrepreneurs (affiliate marketers included) start out, they probably don’t expect it to be a slam dunk and may be just experimenting. That’s the boat I was in. My ex husband was also the CFO of my company and when I got divorced, I had no idea how to manage the financial side of my business! Reading these two books encouraged me to take full responsibility for the role of CFO in my media company and not only that, I decided to invest in expanding my real estate portfolio as well. In fact, within a few weeks of reading these two books I invested in three new rental properties!

  1. Who has been your greatest inspiration?

Julie Stoian and JP Sears! Both successful and super authentic entrepreneurs who inspire me to let go of what doesn’t matter and do whatever it takes to embrace what does. 

  1. What life experience would you alter if you had the chance to?

I wouldn’t. I have been through some very hard things but every experience has made me into the person I am today. I am constantly changing and growing and I am so thankful for that!

  1. How did the idea for your business come about?

As I grew in my knowledge and success as a freelance proofreader, others wanted to know more about how to do the same, so I wrote an ebook about how to successfully proofread from home. Turns out a lot of people were intrigued by it and wanted to know even more than what I had originally offered, so in 2014 I started Proofread Anywhere. It took no time at all for it to explode and become what it is today.

  1. What was your key driving force to become an entrepreneur?

Same as motivation question

  1. How did you come up with the name for your company?

I wanted people to know they no longer had to be tied to a desk. They could proofread… from anywhere! 

  1. How do you build a successful customer base?

There are three strategies I use to attract and retain customers. 

First, I actually care about them. I want them to succeed. I want them to use my courses as a way out. But I’m very clear before they purchase that my course is going to be challenging and they’re going to have to work hard for it. But I tell them that because I actually care about them. A lot of energy goes into emailing my students and future students, responding to their comments, and responding to their emails. 

Second, we run ads. Because we’re profitable, we can run ads on Pinterest, Facebook, and a few other places. This helps us to reach new customers that might not know about us otherwise. 

Third, I email them pretty frequently with helpful information. I touched on it earlier but reaching out to our soon-to-be new students is so important in attracting and retaining our customers. It gives us a chance to bond with them and let them know we care about them. 

  1. How do you market your business, and which tactics have been most successful?

Same as customer base question above

  1. What makes General Proofreading Theory And Practice different from other proofreading courses?

My courses don’t only cover proofreading; I also teach my students how to start their own freelance business, how to find (and keep!) clients, and other tips on how to be successful.

Her Courses/Workshops:

General Proofreading: Theory And Practice

Free Proofreading Workshop


I’m Rohmah Azim. I have been blogging for the past 2 years I founded MakeAndSaveMoneyonline as a way to inspire others to believe in their business idea, and show you that you can do this. The MakeAndSaveMoneyOnline blogging community is a friendly and supportive league. If you are looking for guides on how to start a blog, monetize it and turn it into a business, you’ve come to the right place!

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