When you work in an office, spending 10+ hours a day, butt-in-chair, your mind starts to wander. Amid trying to tune out the mundane office chatter around me, I envisioned a life where I could work on my own schedule, never have to put up with ridiculous company politics, and building a career that served my needs.
At the time, freelancing practically checked all of those boxes. To work with different clients, only doing the things I wanted to do, on my own schedule, and working from wherever I wanted? A DREAM LIFE.
It’s been more than two years since I committed to freelancing full time. And while I feel like while I’ve gotten the hang of certain aspects of working as a remote freelancer, I’m self-aware enough to admit that I’m pretty terrible at it.
Over the years, I’ve explored many potential paths. I considered starting my own marketing agency and quickly realized that agency life was not for me. I’ve built an online course that I could sell instead of client services but ultimately loathed the idea of branding myself as a marketing guru.
Lately, I’ve found my sweet spot in working with 1–2 clients at a time, on long-term projects. I’m not even sure if what I do is even considered freelancing at this point because I’m building long-term relationships that feel much more stable than the freelance work I was previously accustomed to.
I fall more under the “self-employed” category than I do, the full-blown “freelancer” category.
It’s not that I’m bad at what I do. And I’m no longer afraid of sounding too arrogant by saying that I’m actually pretty good at what I do. I put in 100% effort, and my clients always seem very pleased with the work that I do for them. I’m just terrible at “being a freelancer.”
For one, I hate selling my services.
When I tell people what I do, sometimes they’ll respond with an enthusiastic, “oh, I want to hire someone to help me with content!” My response tends to be an underwhelming “that’s really cool you totally should.”
I’ve watched people at parties close new clients, deposit and all, on the spot while drinking beers all because they talked to the right person at the right time. They also had their elevator pitch locked down and what seems like bionic hearing at which they pounce at the first person who mentions their industry or service.
That strategy works. It’s just not for me.
This is almost definitely a limiting belief. But I just don’t care that much about making a sale while I’m out enjoying myself.
I want to have a long-term impact
The limited nature of how most companies communicate with freelancers makes it hard to see how what you do impacts the company. As a writer, I found it difficult to see how I was helping a company meet its goals. My role was to deliver a product. And even though the clients were happy with the product I delivered, I wanted to see how I was helping the company grow.
Now, I’ve been working with the same company for nearly a year. This long-term relationship means that I’ve been able to track how my efforts are actually helping the company evolve and meet its goals. They get to see the value I’m adding on a long-term basis, and I feel more invested in the project because I know my efforts are making an impact.
These long-term relationships have really helped me bridge the gap between the benefits of being an employee versus a freelancer. I still have the freedom of working on multiple projects, being location independent, and setting my own schedule. But I also get to feel like I’m a part of something bigger and contributing to growth in ways that I never felt when I jumped from client to client as a writer.
I’ll never go out of my way to convince someone to hire me
Surviving as a freelancer requires playing offense. Consistent outreach and persistent follow-ups are crucial to maintaining a pipeline of clients and keeping the money coming in.
I played this game for over a year. I spent significantly more time looking for new clients than I did actually doing the work I was hired to do. It was exhausting. I did not sign up to be a salesperson, but the majority of my time was spent selling myself.
When I was broke and desperate, this meant sending follow-up after follow-up until I got a firm “yes” or “no” answer. I got a lot of virtual doors slammed in my face because of this annoying dedication to persistence.
I was working with a coach at the time who insisted that this in-your-face strategy was the only way to show potential clients how serious I was. I was willing to do whatever it took to make it, so swallowed my pride and sent hundreds of cold emails, even a few *gulp* cold calls, until I secured my first handful of clients.
This strategy helped me land clients, but I knew it wasn’t sustainable for me long term. Mostly because I hated it, and also because I felt like a huge bother to the people I reached out to. The conversations felt inauthentic, and I didn’t want a pity invite to the party just because I asked a million times.
I value autonomy and setting boundaries
On a few occasions, I’ve had calls with potential clients who set the expectation that I would have to use a time tracking software in order to get paid. This software in question tracks the amount of time that you spend working on their project. In some cases, it randomly screenshots your computer screen while the clock is running to ensure that you’re not doing other things during their billed time. One potential client went as far as to call to me entitled for suggesting that they should pay me based on outcomes rather than billed hours.
While I understand companies wanting to hold their contractors and employees accountable for their billed time, this is a hard no from me.
In my opinion, it says a lot more about where the company’s head is at if they need to know what you’re working on every second of the day, rather than judge performance based on outcomes.
Sure, there are some cases where hourly billing might make more sense, and I can see how companies may have been burned in the past by shady freelancers. But I also think it’s important to set personal boundaries, and this was one of mine.
A lot of these reasons have probably stifled my ability to scale my income, or may have made me an unattractive option for some businesses. But doing what feels right to me has paid off dividends in the long-run. I’ve found a flow that makes me excited to get up in the morning and do what I do. I no longer stress about what potential clients think or feel resentment because I took on a project that doesn’t serve me or crosses boundaries.
I’ve learned that freelancing looks different for everyone and not to box myself into what I think it should mean to “be a freelancer.” I’ve learned not to be afraid to stand up for myself. And I’ve learned that if one client doesn’t work out, an even better one will come along eventually.