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

Learn more about the important decision that helped me the most along my self-employment journey, including some accounting advice.

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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 about my self-employment journey. Thought you should know that before reading!

I saw a LinkedIn poll the other day, which asked a simple but powerful question about the self-employment journey:

What’s the number one thing that helped you in your career or on your self-employment journey?

Fifty two percent of poll respondents chose “Believing in my ability.” Fair enough. I do think mindset is an important part of making money as a writer. I still fend off creeping self-doubt on a daily basis. But my answer of choice for this poll was different.

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 it felt like I couldn’t. What if my employer found out? What would my colleagues (and boss) make of my side hustle?

Would the world find out I was living two lives and suddenly come crashing down around me.

Once I left my full-time role, I found it so much more natural to embody my business online and in person. On prospect calls with potential customer. During in-person conversations about “what it is I do for a living.” This was near the end of 2020. And it’s precisly when things took off with respect to my self-employment journey.

How my self-employment journey changed when I began treating my business like a business

Another part of this journey has been treating my business like a damn business. I started paying closer attention to revenue, client mix, taxes, expenses—all of the numbers stuff that I used to avoid. It certainly didn’t happen on its own. Frankly, I grew weary of sending the government what I thought I owed in estimated taxes each quarter.

So I decided to change my business structure with the help of Collective. Copy Martin is officially an LLC! Not just any kind of official—Twitter official:

Why I chose Collective to handle my accounting and bookkeeping

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: no more 9-5 job and my own bonafide LLC. Of course, I needed help with almost every aspect of the process, which is why I decided to hire Collective to take care of it for me.

Strong customer experience and community

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.

The tax savings

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 in revenue annually, an LLC taxed as an S-Corp might make a lot of sense for you.

You could save thousands on taxes alone.

One of the advantages of this model is that Collective helps you legally and ethically reduce your taxable income, something I couldn’t achieve as a sole proprietor (hence my inflated payments for estimated taxes each quarter).

The crash course in how to manage the numbers for a freelance business

I was skeptical, too, mostly because I knew the process would make me uncomfortable. Again, worth it! I spent a lot of time poking around the company’s blog and help center to see what’s what. What I found was a veritable crash course in taxes and bookkeeping for freelancers—one that quickly revealed a lot about my previous approach to accounting that I’d gotten all wrong.

What’s issue #1 on your self-employment journey?

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. That said, you can read my full review of Collective, the S Corp back-office tax platform.

Lastly, I’m curious:

What’s the number one thing that helped you on your self-employment journey?

Was it leaving your job? Finding the right network? Believing in yourself. Let me know how you’d vote in the comments section. I’m always up for a healthy discussion.


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