Launching a Business and Scaling Up: Lessons From 3 Successful Freelancers

By Bethany Johnson, Contributor, on June 27, 2018

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As Denis Waitley, author of The Winner’s Edge, famously said, “Never become so much of an expert that you stop gaining expertise.” In the indy world, it’s important to remember that continuous learning separates the entrepreneurs who are experts at launching a business from those who go beyond: those who can start, stabilize and scale a business.

In other words, what got you here won’t get you there. To succeed, you’ll need to master one skill after another. Forever. But don’t allow yourself to get overwhelmed or discouraged. Remember that there’s an easy way for you to learn important lessons from fellow freelancers at different stages of their business growth. All you have to do is ask.

I caught up with three fellow freelancers at varying stages of business ownership:

  • Starting: Ivy Brooks, founder of The Copywriter To Know and a freelance copywriter-for-hire, is an adventurous soul who’s in the thick of launching a business, which is currently under the six-month mark.
  • Stabilizing: Janice Laraine, founder of Miss Adventurepreneur and a freelance brand strategist and website designer, launched last year and has already gained some traction.
  • Scaling Up: Erika Ashley, a personal brand and publicity strategist at Erika Ashley + Co., is a freelance veteran who’s been in business successfully for over 13 years.

To get to the bottom of which business skills are most important (and when), I asked them all three major questions.

At your current stage of freelance business ownership, what would you say is the most essential knowledge to possess?

Ivy: “At this stage, discernment matters most. You have to [be discerning about] the people you follow. It’s important not to do it all alone and to have mentorships. In fact, you should definitely have quality leaders to follow. But you have to discern that, and you have to wade in the waters (for a few months, even) to discern which business coaches and leaders are the real deal.”

Janice: “The number one thing is networking — making connections with other people and helping people — because it’s really going to help you create more income streams the further along you get in your business. So let’s say, for example, you network with another designer and at one point, that person decides to start a podcast. Since you already have that network [established], you can probably be featured on their podcast. And then you can republish that on your website to get extra traction, and then maybe you can get featured on something else since you already have an interview on a podcast.

Also, I would say that a good network could basically be your secondary knowledge base. You only know so much. Networking helps you connect with other people to expand that knowledge, especially in those areas where you don’t know, but you can ask another designer.

And finally, continue putting yourself out there. I know a common beginners’ question is, ‘How do I get my first client?’ And then there’s a transition to the question of ‘How do I book out three months of work in advance?’ So to a beginner, I would say [to] put yourself out there first. Let people know that you’re providing a service. That’s the most important thing. And then, for ongoing clients, it’s about getting comfortable with speaking, and getting comfortable with the sales process. So, really, it’s about the shift from just putting yourself out there to understanding how to have those conversations with potential long-term clients. Then, you get to a point where [you’re] ideally having those high-level conversations and positioning yourself as an expert.”

Erika: “After hitting six figures in revenue, knowing about income stream diversification is essential. In my industry, PR and brand strategy, most people hit six figures with one-on-one client work, but that’s difficult to scale, as you’re capped on how many hours you can realistically work. So knowing about the other options available to you to grow your revenue is essential.

Knowing how to build relationships is also essential. You’re the result of the five people you spend the most time around, so you want to make sure that those people are going to challenge you, motivate you and inspire you. If you don’t up-level your mentors, friends and colleagues, you’ll stay stuck.”

When you reached this stage in your business, what’s something you learned that surprised you?

Ivy: “I learned how heavy in sales it is. If you love what you do, sure, that’s half of it. I strive to be the best I can be at what I do, but I also have to strive to get better and better at educating people [who] don’t know about it. I’m always explaining the value of what I do. I was surprised that pitching and putting yourself out there is a never-ending process, until word-of-mouth spreads or you are just comfortable with your client load.”

Janice: “Learning [what] a client needs and delivering it. It’s one thing to have a list of packages on your website, but it’s something entirely different to listen to a client’s pain points and work up a plan to address them. One of my newer clients had a formatting issue with her blog which I did not know how to fix. So I said, ‘Let me look into it, and I will get back to you on this.’ And I did. I made sure that I understood it before telling her I figured it out and offering to show her how to do it or to complete the task as an add-on service. Clearly, I don’t work for Squarespace [and] I’m not a technical expert, but again, with professional networking, I can utilize someone else who’s an expert to address a client’s unique need.”

Erika: “Six figures is not a cure-all to life’s problems. Because six figures is hallowed as a huge milestone to reach, I assumed that it would also come with certain perks — working less, more credibility, all that. And while that’s sometimes the case, in order to grow my income further and scale based on my desired lifestyle, I’m actually still putting in significant hours in my business. And while it’s more than worth it because I know what I’m building, it’s not the six figure dream everyone makes it out to be.”

What are some key lessons you would offer to other freelancers who are entering your unique stage of the journey?

Ivy: “To someone launching a business, [who’s] about to take the leap, I would advise them to prepare financially. First, I would tell them to brush up on personal finances, because you’re going to have to budget your personal finances to succeed on the business side. The second piece of advice would be to put people in place as best you can. You’re going to want to be supported, and that’s not just mentorships. Let your friends and family know what you’re about to embark on so you can get the support you need.”

Janice: “I would re-emphasize the importance of that network, doing research to position yourself as an expert, to give value and answers to those questions that other people are looking for. And if you don’t know something, view it as an opportunity. [Think of it as] a fun little project, that, once mastered, you can add to your list of services or add to your repertoire of things that you know and can offer.”

Erika: “Trust your gut and intuition above all else. When it comes to hiring mentors, strategic shifts in your business and the like, remember, nobody knows you better than you. While you need to take your business seriously to make it work, also treat it like an experiment. Sometimes, you try things and they will fail, but you’ll also have unexpectedly awesome moments that lead you to where you are now.

Have a big-picture vision in mind and don’t make your business all about the money. While we all crave financial freedom, life will get pretty boring if you’re just chasing after more money. Start with a self-centered goal of the life you want to create and then how you want to impact others. It’s like the oxygen mask instructions on the plane: If you try to put on someone else’s mask before your own, you might both end up passing out.”

Tips for Every Stage of Self-Employment

You won’t need to learn how to juggle six-figure clients when you’re just launching a business. And you shouldn’t be looking for a startup mentor after you’ve been growing your freelance business for a decade. Instead, take these time-appropriate tips to heart when they matter most:


Be more discerning. Learn who to trust and why. Research and select a guru (or two) to follow, and do your best to ignore the rest. Recognize that this may take time, but the wait is well worth it.

Learn everything you can about the sales process, because while you may be an expert in your craft, you’ll need to be able to compete to land work. Being able to explain the value of your offerings can help you do exactly that.

And finally, start looking at your personal finances through the mindset of a business owner, and ensure that you can stay afloat financially during the feast-or-famine cycle of typical freelancing.


Congratulations! You’ve got your first client or two, and you’re ready already on the path to success. Forget just keeping your head above water: You now see what’s possible, and you want to navigate your way toward specific business goals. To do that, build a network that you can both pour into and benefit from regularly. Consider hiring and practicing with a sales coach so you’re always ready for any type of client. Lastly, start looking at your clients’ frustrations as potential different niche offerings that you could learn, and advertise your solution.

Scaling Up

As a veteran freelancer, you’ll need to acknowledge the disenchantment that a “super successful” personal brand can bring. Then, adjust your thinking. Diversify your income streams by being more strategic about every business relationship you nurture. Allow yourself to experiment, since these days, very few failures have the potential to sink your ship. Those measured risks can pay off now like they never could have in the beginning. Plus, you’ll bring new skills and offerings to your business that will reinvigorate the passion that drove you to self-employment in the first place.

No matter which stage of business you’re in, it’s essential to continue learning and building your brand. By focusing on particular areas of growth at each stage of development, you’ll prepare yourself to move to the next level — and you’ll have the capabilities needed to succeed as your business grows.

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