Lucy Cantley’s First Year Freelancing: You Don’t Know What You Don’t Know

By Erin Ollila, Contributor, on July 25, 2018

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Lucy Cantley is a military wife, a new mom and a burgeoning businesswoman who’s wrapping up her first year freelancing. When she moved from England to the United States at age 21, she started out in administration and eventually became a jack-of-all-trades in a corporate position.

But throughout her early working years, Cantley never felt like she was truly doing what she was meant to do. As a child, she loved the work flexibility her mother was able to enjoy as a self-employed accountant. Many years later, Cantley’s own frustrations with the business world led her to realize that the freelance life could be the key to a happier future. This realization gave her the drive she needed to start her own business.

Today, Cantley works as a “business sidekick” to help online entrepreneurs create beneficial systems and strategies — all while managing the projects clients throw her way. She recently sat down with me to discuss her indy experience, as well as the lessons other individuals looking to start their own businesses should know before diving into self-employment. Her main takeaway for new freelancers? You don’t know what you don’t know.

Lucy Cantley

What motivated you to leave traditional employment and start your own business?

I was doing my MBA full time. I was tied to a venture capital group that was part of the university, and through that I met an entrepreneur who needed some help, and I started working full time for her startup. So I was doing a lot of different things all at once, and then I got pregnant.

I don’t know, just everything changes when you’ve suddenly got to think about, ‘Okay, how is my life going to work around a newborn?’ — and I learned very quickly that the tech startup just wasn’t going to work with me. The uncertainty. I wasn’t getting paid because there wasn’t enough money coming in from investors, so I knew I needed a shift. I can’t work as much as you need me to work on zero pay and have a newborn, because I can’t pay for childcare if I’m not getting paid.

How did you decide what you would offer?

I knew that strategy and problem solving and advising people on their business [were things] I really loved to do, and so initially I was like, ‘Oh, I can be a consultant!’ And then I realized that, because I’m a little bit of a control freak and I like to see things through, I didn’t want to just advise and hand over things. I wanted to be involved in the process, which kind of led me to think, ‘Is that a project manager?’

I call myself a business sidekick. I don’t call myself a project manager, because I’m a hybrid. I made up what I do.

It was interesting, because my [business] coach needed someone like me, and so that was also part of the journey. She was like, ‘That’s really interesting that you said that, because I need something like that,’ and it really validated that what I wanted to do was something that people needed from me.

When starting a business, I think it’s so important to get outside your own head and talk to people about your idea. It’s the best — and fastest — way to get validation on whether you’re onto something.

What kind of support would have made life easier or better during your first year freelancing?

When I first started my business, my first big expenses were a copywriting course, a branding package and headshots. Having a professional brand from the get-go was important to me, but I know plenty of people who’ve had great initial success without this. Next, I hired a business coach — not only to advise me on next steps, but also to help grow my network of collaborators, clients and entrepreneurial friends. I [knew] I could go to the government’s small business website and find information on how to start a business. And I was very proactive about finding mentors and things, as well …

The challenge is: You don’t know what you don’t know. And I think that’s the problem when you start a business.

There’s just so much you don’t know, and you just have to figure it out as you go. Knowing where to find the things that you need to know is kind of the important thing. So, for example, it’s only recently that I started working with a lawyer to make sure I’m checking all the boxes that I need to check for my business in a legal sense. I’m self-employed, but there [were] just a few contracts and things I needed to have in place.

I feel like I reached this point where I was like, ‘Okay, I’ve upped the ante and the stakes feel higher, and I’m starting to feel very uncomfortable with the fact that I don’t have these contracts in place.’ So that was the point of [a] gut check … it [was] time to take action on this thing now. It wasn’t an easy process, because there was still a lot that I didn’t know. So that was the great thing about working with [my lawyer], because she knew what her other clients needed, and was able to take her experience and apply it to my situation, so that I had the coverage and the protection for things that I didn’t know that I necessarily needed.

So reaching out to the right people was helpful for you. How did you learn to navigate tax and financial considerations unique to freelancers?

I will say that one of the best things I did was [make] sure that I was tracking everything from an early point in my business. This year, taxes were not too bad, because I really tracked everything, and there wasn’t anything big and scary that I needed to get advice on … There was some Googling, and some asking people for support, and then I realized that I didn’t need to hire a professional at this stage. I’ve worked in accounting, and I’m quite good at keeping track of the numbers.

But as I approach next tax season, I think there are just more complexities. My business wasn’t profitable in 2017, so I didn’t owe anything. I invested money into my business and took time to do everything. Next year, I’m going to need an accountant.

You don’t think about those things when you start your business. You just want to do your business. But those are the things that are important, and by the time you hit that first-year mark, you [have] to have a clear idea of: Have you got your accounting stuff in order? Have you got your legal stuff in order? Are you doing everything by the book? Because you don’t want anything to come back and bite you.

Do you think your first year as an indy helped you to determine the new things you needed to learn and know?

Yes. The reality is that you can spend forever planning your business, and trying to prepare to do everything [perfectly] from the get-go. But that’s not realistic. That’s not what people do. Just jump in and do it, and figure it out as you go.

How do you feel we could “fix” freelancing so that the transition from a typical working situation is easier?

We live in a world of information, so information’s out there, but as I said, we don’t know what we don’t know. I wish I had known earlier the number of opportunities that were available to me, especially in the online space, because I could have been doing this a long time ago. It wasn’t until I fell into online groups. I don’t even know where I started, but I spiraled into this community and was like, ‘This is where I need to be.’

So I think that’s the first step — being aware this option is available. You don’t have to go work for a corporation. You can be a freelancer, and you can have great success being a freelancer. You just have to have a skill set and apply it.

To learn more about Lucy, visit her website, follow her on Facebook or take her free training on how to go from idea overload to a focused plan.

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