The #1 Thing That Helped Me On My Self-Employment Journey

Learn more about the decision that most helped me along my self-employment journey as a freelance content writer.

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Disclosure: This site participates in affiliate programs. So you know, Copy Martin, LLC may earn some recompense from the companies mentioned in this here blog post. Thought you should know that before reading!

I saw a LinkedIn poll from Collective the other day, which got me thinking. What’s the number one thing that helped me on my self-employment journey? Fifty two percent of poll respondents chose “Believing in my ability.” Fair enough. I still fend off creeping self-doubt on a daily basis.

Here’s how I voted.

Answer: quitting my 9 to 5

When I was still juggling both a full-time role and running my freelance business on the side, everything was one foot in, one foot out. I wanted to talk about my freelancing journey, engage the community, and step into the shoes of my digital brand; but I couldn’t go all in given my employment status.

At least I felt like I couldn’t.

Once I left my full-time role, however, I found it more natural to embody my business online and in person. On prospect calls. Everywhere. This was near the end of 2020. It’s when things took off with respect to my self-employment journey.

Also, treating my business like a business

Another part of this journey has been treating my business like a damn business. Paying close attention to revenue, client mix, taxes, expenses—all of the numbers stuff that I used to avoid. To kick my own ass into gear, I decided to change my business structure with the help of Collective.

Copy Martin is now officially an LLC! Not just any kind of official—Twitter official:

Back when I was still working in-house while juggling the side hustle, forming an LLC (which is taxed as an S Corp) seemed out of reach. Over my head and too official for what I was up to. Yet, here we are. Of course, I did need help with almost every aspect of the prospect, which is why I decided to hire Collective to take care of it for me.

Why I chose Collective

As someone who has written and researched quite extensively in the customer experience space (see my author page at Coveo, for example), I can tell you that Collective has a terrific onboarding and education process. When I have a question about nearly anything—can I expense the damages to the Ferrari I crashed on a test drive? are new Jordan 1s tax deductible?—I just send an email and a CPA responds within 24 hours.

Moving forward, they’ll be taking care of my taxes, bookkeeping, and accounting (including my family’s annual tax filings). It’s definitely an added monthly expense, but worth it—at least for me. If you’re a freelancer running a sole proprietorship and bring in more than $80-100K annually, an LLC taxed as an S-Corp might make a lot of sense for you.

You could save thousands on taxes alone.

I was skeptical, too, mostly because I knew the process would make me uncomfortable. Again, worth it! If nothing else, poke around the company’s blog and help center to see what’s what (kinda wish I did that before I signed up). It’s a crash course in taxes and bookkeeping for freelancers.

If you like what you see, friend-o, use my code COPYMARTIN to get a month free when you join Collective. Yes, that’s an affiliate link. But I’m selective about the products and services I recommend, and this one has really helped move my self-employment journey forward. I wouldn’t share it if I didn’t think it could help other sole proprietorships get their books in order and save money.

What’s standing between you and full-time freelance?

Lastly, I’m curious: what’s the number one thing that helped you on your self-employment journey? Leaving your job? Finding the right network? Let me know how you’d vote in the comments section.


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