My first year of self-employment was equal parts exciting and eye-opening. I left behind the corporate structure, stepped into the world of solopreneurs, and began building a business on my terms.
But along the way, I hit a few painful roadblocks, ones I wish someone had warned me about.
These five lessons will help you avoid common pitfalls and stay on course when you’re just starting on your solopreneur journey.
This post may contain affiliate links, which means I will make a small commission if you purchase through those links. Read full disclosure HERE.
Top 5 Lessons I Learned in My First Year of Self-Employment
1. Don’t Do Business with Friends (Unless Boundaries Are Clear)
Your first instinct may be to turn to friends and family for support or collaboration. But without clear agreements, that support can backfire.
I learned the hard way that working with friends often blurs professional boundaries, and you may end up undervaluing your services or worse, resenting the relationship.
Friendly discounts? Sure, if you choose. But unpaid favors? Not sustainable.
2. Say No to “Too Good to Be True”
Self-employment comes with financial pressure, especially in the early months.
That’s why get-rich-quick schemes can seem tempting when the bank balance dips.
Several polished pitches promised fast returns, but none panned out. Stick to building something real. If it sounds too good to be true, it probably is.
3. Friendly Clients Can Cost You
It is important to have a great rapport with your clients. But when that rapport starts to feel like friendship, boundaries can erode.
I said yes to unpaid extras and justified lower fees because I “liked” the client. Set expectations from the beginning. You’re not a volunteer, you’re a professional.
4. Don’t Give Away Your Expertise for Free
Your knowledge and experience are valuable. Early on, I spent hours crafting strategy outlines and proposals for people who never intended to hire me.
They were “just picking my brain” for ideas, then ghosting. Lesson? Don’t provide detailed advice without a signed agreement and payment structure.
Be generous, but not at the cost of your own business.
5. Get at least 50% of Your Money Upfront
Cash flow is your business’s lifeline. I once took on a project without a deposit, trusting that payment would come later. It didn’t, and I was out over $1,000.
From that day forward, I implemented a simple rule: No work begins until at least 50% is paid.
Use invoicing tools like FreshBooks or QuickBooks to automate this process and stay professional.
Optimize Your Solopreneur Life
The first year of self-employment is filled with growth and growing pains. The lessons I’ve shared here are just a few of many, but they’re foundational.
Protect your time and income, and build relationships that respect your value.
With each new client, project, and decision, I’m learning to stay firm in my boundaries while delivering my best work.
That’s the energy I’m taking into year two, and beyond.
Anna is a solopreneur, writer, and creative entrepreneur who left her 9–5 after paying off over $40,000 in debt to pursue a more intentional life. She founded The Writer Entrepreneur to empower others to build debt-free, freedom-driven lives through smart planning, goal-setting, and online income streams. She has been featured on HuffPost, YouQueen & Fitnancials among others. Learn more about Anna HERE.
This post may contain affiliate links which means I will make a small commission if you purchase through those links. Read full disclosure HERE.
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