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Heart-repreneur® RadioPodcastsHeartrepreneur® Radio | Episode 25 | How To Work Your Way To Success After Burnout with Laura Pennington

April 3, 2017

25HPRbanner - Heartrepreneur® Radio | Episode 25 | How To Work Your Way To Success After Burnout with Laura Pennington


Even our burnouts could be blessings in disguise. If you search through a number of great entrepreneurs out there, some of them only ever discovered their own paths to success after falling out of something. No exemption to that is Laura Pennington. From being burned out, Laura decided to become a freelance writer, which later grew and turned into a successful business. She shares her story success after burnout and provides some inspiring tips. Laura lays down great advice that would help aspiring virtual entrepreneurs to improve their business in many aspects.

Listen to the podcast here:
How To Work Your Way To Success After Burnout with Laura Pennington

My guest is Laura Pennington. She left her career as an inner-city geography teacher after burning out. I know many of you have been burned out as well. Not knowing what was next, she googled “How to become a freelance writer?” She landed her first paid gig soon after. From there, she built a six-figure freelance writing business that allows her to travel the globe and do what she loves. She now teaches others to start their own careers as a virtual assistant or a freelance writer. She also teaches online entrepreneurs how to use digital teams to scale their businesses. 

Laura has been featured on Writers Weekly, The Huffington Post and Business Insider. She has worked with many of the most successful personal injury law firms in the US as well as companies like Microsoft and TrueCar since she got started as a writer. I went through burnout, which is what led me to be in the career that I love and enjoy. What made you even Google, “How to become a freelance writer?” Was writing something that was in your heart? What was going on?

I was in the midst of a PhD program at the time. My whole adult life had been working towards a career in education, so to come to terms with the fact that that wasn’t going to work for me while I was working as a teacher led me to go, “What skills do I already maybe have?” I had never been paid to be a writer. I wasn’t even on the school newspaper, none of that. I had had some professors in college and in graduate school who had encouraged me with my writing ability. I tutored quite a few college students when I was teaching in the Political Science Department at Virginia Tech while getting my master’s. I thought the learning curve with writing is going to be a little bit easier for me than teaching myself graphic design or web development. I thought all I need to do is teach myself how to write for the web or how to write for magazines and that’s the only reason that I googled it. I never intended it to be a career. I thought it would be a great way to have some extra money, but it grew very quickly.

Focus on giving people a positive experience. Click To Tweet

How did it grow? I’m always curious when someone’s business takes off and how that happens for them.

For me, I focused on giving my first couple of clients an amazing experience. They were taking a risk on me. I’m a total stranger on the internet. I don’t even have a degree in English or anything like that. For me, I focused on delivering early. I focused on turning a content that was above and beyond what they expected. I made things easy for them. I took things off their plate that didn’t require a whole lot of hand-holding or instruction. That made that first couple of clients to want to not just give me one project but keep working with me, refer me to others, and give me testimonials that would allow me to earn other business. It’s so easy to do those little tweaks like that where you’re focusing on giving people a positive experience. Once someone finds a good writer, they’re much more likely to stick with you. There’s no need for them to go back out in the marketplace. When their colleague from law school or whatever asks, “I need a blog writer,” I’m going to be the first name that comes to their mind because they’ve already had a positive experience with me.

25HPRCaption1 - Heartrepreneur® Radio | Episode 25 | How To Work Your Way To Success After Burnout with Laura Pennington
Success After Burnout: I’m going to be the first name that comes to their mind because they’ve already had a positive experience with me.

I know that’s helpful for many of the audience. I’m glad that you shared that. How did the virtual assisting come to be?

I was all over the place doing different projects and a lot of it was writing. Occasionally, I’d have people reach out to me and asked if I could help them with what at the time I considered random projects. A real estate developer in Florida said, “I don’t have time to run this newsletter campaign.” It involves sending things physically through the mail and he goes, “I’ll buy you toner and paper. I’ll buy the stamps and I’ll buy the envelopes. Will you take this information and run it through mail merge and print it for me to take it to the post office?” I thought, “You’re going to pay me to do that? You’re going to give me all the supplies? I can’t argue with that.” I took on quite a few jobs in that virtual assistant capacity as well, running things behind the scenes for business owners. I use virtual assistants today to run my businesses. I know both sides of that opportunity, both being one and hiring one.

Sometimes the market chooses us and sometimes we choose the market and we pay attention when it showed up. Virtual assistants have been a part of my company for the two decades that I’ve been running this company. I started my business and the very first thing I did three days later was I hired a virtual assistant. Most people would be like, “What did you need one for then?” I had the vision in mind, the end in mind, and knew that a team member could help me and now I have a team of three virtual assistants. They literally are why I’m successful. I couldn’t do what I do without them. It’s so important. You also say that you teach online entrepreneurs how to use digital teams. I’d love to hear more of, “What is a digital team? What does that mean? How do they help a business owner scale their business?”

It sounds like you already have what I would consider a digital team, which is basically more than one individual that’s working for you. They don’t all need to be working on the same projects, but there are definitely multiple people involved in the equation. Some of them may be involved at a deeper level. You might have an online business manager who’s your second in command, but then you might have people that you work with on a contract basis.

I use a VA once a month to create all the images for my social media or I have a podcast guy who’s dealing with all my podcast audio editing. Working with a digital team is a great way to replicate yourself. A lot of entrepreneurs say, “I wish I had more of me. I only have 24 hours in a day.” Every entrepreneur is going to hit this point where there’s literally no more than you can do on a given day. If you’re doing too many things, they’re not as effective or as high quality because you’re tired and you’re burned out.

Digital teams make use of whatever type of professional needed to leverage your business and to scale. It is important for any entrepreneur and business owner. Even brick and mortar businesses can benefit from having digital team members. I’ve also worked with companies like TrueCar and Microsoft. I was involved in a project where I was managing a team of twenty writers producing more than 400 blogs a month. We did that for nine months. I learned a lot of trial by fire lessons about hiring, training, retaining, and effectively managing the administrative parts of running digital teams. A lot of people get hung up on this idea of outsourcing because they’ll hit a snag early on in the process and then they’ll get flustered and go, “I should do this all myself anyway. Forget it.” Forget working with a VA, forget working with the digital team, and quit entirely when the truth is there are some small tweaks and some systems and processes that you can put into place to help everybody be effective.

You learn a lot of lessons through trial by fire. Click To Tweet

I do have a digital team. I’ve got someone that manages my Infusionsoft, my website, my newsletter delivery, and helps with social media. I’ve got someone managing my radio show. First of all, I don’t know how I would be successful in business without that. Whenever I talk to someone who is trying to get to six figures and to seven, you cannot do it alone. You can’t and even if you think, “I’m better at something or I need to do that.” Learn to give it up and to delegate and learn to train people and allow them to make mistakes. That’s been my experience in my 30 something years in business. I’m going to say amen to what Laura said. I think that’s absolutely brilliant. What are you most passionate about, Laura? What is on your radar?

I’m making a little bit of a shift in my business and I’m a little bit terrified about it. I’ve spent four years writing words for other people and I know I’m good at it. It’s something I’ve been able to replicate every single month and pay my bills and all that. I feel like I’ve gone as far as I can go with freelance writing. I have some amazing clients. I love what I do, but I’ve been feeling the call to go into fiction and nonfiction writing of my own for a while now. Even though I have all this experience as a writer and I’ve got the academic background to do research and all that, I’m a little bit scared. I feel like I’m visualizing me standing on the edge of a bungee jumping thing. Where they tell you to lean a little bit, I’m leaning, but I’m not jumping yet. That’s what I’m passionate about trying to talk myself into having the guts to do this.

That’s when we make the biggest shifts in our life when we’re standing on the edge like that. The biggest transformations happen. How can the listeners stay in touch with you, get in touch with you, and be connected with you? What’s the next action they can take to get to know more about you and maybe even hire you and get some help? You offer some great tips and tools.

All of my writing and advice is housed on I separated my advice for busy entrepreneurs about all things business, digital teams and things like that on If you visit, you can get a list of 70 tasks to get you started thinking about outsourcing. 70 tasks that you can get to your first virtual assistant. That usually helps people get the juices flowing and thinking and realizing all of the things they’ve got on their plate that they don’t need to be doing.

Is there anything else that you want to say that an audience would need to hear? Any words of advice or Laura Pennington words of wisdom?

One of the consistent themes in my life and one I need to highlight for myself again is this idea of just go ahead and do it and try. My only real regret with my freelance writing business is that I didn’t start sooner. I had no idea that I had such a sellable skill and that it would be something I wake up and love doing every day. If you have a passion for something and you feel as though you’re being called to do it and have that drive to push through, don’t wait any longer because there is that chance that down the road you’re going to look back and go, “I wish I’d done that earlier.”

25HPRCaption2 - Heartrepreneur® Radio | Episode 25 | How To Work Your Way To Success After Burnout with Laura Pennington
Success After Burnout: If you have a passion for something and you feel called to do it, don’t wait any longer because there is that chance that down the road you’re going to look back and go, “I wish I’d done that earlier.”

I always believed that. No matter where you are, look at, “What if I do, what if I did?” versus sitting there. The human brain is so good at coming up with excuses. “Not now, this isn’t a good time.” We can all do that. Laura wouldn’t be where she is, I wouldn’t be where I am, and many of you wouldn’t be where you are. Some of you who might be stuck right now. Laura googled something and changed her entire career and probably changed her life in many ways.

I was on the fast track to burnout before and never imagined that this would be a career. At this point, it’s also the job I’ve held down the longest. Even though there are difficult days, even the worst day of my freelance writing business does not even come close to a day in the life of a seventh-grade teacher. It’s definitely been worth it and a major change for me.

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About Laura Pennington

ZEjqS4Cg 400x400 150x150 - Heartrepreneur® Radio | Episode 25 | How To Work Your Way To Success After Burnout with Laura PenningtonI’m Laura Pennington, and my passion is teaching you exactly how to fast track your freelancing career, skip over the trial-and-error stage that can last for years, and build a fulfilling lifestyle business as a freelancer.

In 2012, I went from part-time freelancing to a six-figure freelance writing business in just 18 months.

I want this kind of success for you, too. And in today’s rapidly-growing freelance economy, it’s more than possible. It’s yours if you’re willing to put in the work and fine-tune your skills.

And if you’re willing to put in the work? The returns are immeasurable. My military family and I move all over the world without my career skipping a beat. My schedule is my own and I get to explore all my favorite things, from swimming to literature to tap dancing. I even have a passion for public policy research impacting domestic violence victims (I’m currently a PhD candidate).

It’s a full life I wouldn’t trade for the world. And my lucrative freelancing business has made it possible.

It’s why I offer one-on-one coaching, courses, writing reviews and more. I want to help freelancers like you launch your business and grow it into the six figures.

But let me level with you: you’ll never hear me telling people how amazing life will be as a freelancer without also talking about the reality that it can be tough sometimes.

My students tell me they love my upfront approach grounded in practical, actionable (and affordable) advice they can actually get started on today:

  • One client had been trying to land a freelance writing client for two years with zero luck, then landed two clients within a week.
  • Another client booked her first 100 hours onUpworkeasily using my strategies, all working with clients she loves.
  • Several clients landed their first few (or ten!) clients after implementing my strategies.

If you have the talent, you absolutely can make an amazing living online. It’s time to bust through your mental limitations and just get started.

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