The Trusty Oak Post

Exhausted and Lonely? There's a Better Way to Freelance

April 12, 2019

This is part one of a two-part series that examines the Trusty Oak difference and how our business model provides benefits for both freelancers (our virtual assistants) and the clients we serve.

Freelancing: Perception Versus Reality

Freelancing is appealing. It offers flexibility and control, allowing you to work on a schedule you create from a location you choose. It often evokes exciting images of working from the couch in pajamas or sitting at a laptop by the beach. But for those of us who have taken the plunge to freelance full time, we often find this perception of freelancing doesn’t exactly align with reality. While there are many positives, there are some serious pain points and things that simply aren’t as fun or glamorous as the pajama fantasy led us to believe.

From demanding clients, to lower-than-expected pay rates, to mind-numbing work assignments, to dealing with irritating tasks (I’m talking about invoicing), freelancing can be difficult.

Related: So You Want to Be a Virtual Assistant. Now What? 

The Trusty Oak Difference

The good news is, freelancing doesn’t have to be this way—and here at Trusty Oak it isn’t. Trusty Oak was founded to offer the flexibility and benefits of freelancing without all that less-than-desirable stuff. Below we take a look at some common freelancing drawbacks and show you how Trusty Oak offers something different (and I mean really different) than a standard freelance gig.

Finding Clients + New Business

Traditional Freelancing: If you have an amazing network and many referrals, business development (finding clients) may be a relatively easy task. But for most of us, even the most connected, it still requires a good deal of time and effort to get your name out there. Many of us aren’t bizdev people by nature, so not only is this process time-consuming, it’s hard! And of course, time spent finding clients as opposed to working is time you don’t get paid for.

Trusty Oak: Trusty Oak’s dedicated Sales Team handles all business development and securing of clients. This means you don’t have to find your business, eliminating this not-so-fun and extremely time-consuming part of the freelance equation. With Trusty Oak, the clients are already lined up and you can even select which clients you’d like to work with based on your skills and interests. This means you can get straight to work and focus on what you do best. Trusty Oak even allows you to increase and decrease client workload, depending on your availability over time.

Dealing with Logistics

Traditional Freelancing: You secured your clients and feel awesome! But the work doesn’t stop there. You still have to make a contract, negotiate terms, and secure a rate. This can be unnecessarily difficult and stressful, especially with the abundance of people offering services online for rock-bottom prices these days. And I didn't even mention the hassle of invoicing.

Trusty Oak: Trusty Oak offers standard rates, and takes care of any negotiation and upfront work associated with new business. Your time is tracked quickly in an online system, and Trusty Oak’s billing team takes care of all invoicing, meaning you don't have to deal with any of the logistical stuff!

Doing Actual Work

Traditional Freelancing: While ideally, freelancing allows you to continue to do the work you were previously doing and hopefully enjoyed, the reality is that many times we have to make concessions. Many assignments are low-level and uninteresting, and finding quality projects can be a struggle. Even worse, some people can’t sustain themselves financially on freelancing alone, meaning they turn to alternate means like doling out coffee or selling the latest fashion trends at the mall. Which may not exactly be what you envisioned.

Trusty Oak: At Trusty Oak, you can keep doing what you did before without risk of mind-numbing tasks nor a supplementary retail gig. With a diverse base of high-level clients and a multitude of project types ranging from admin to marketing to strategy, Trusty Oak allows you to do interesting work you actually care about. It’s not so much leaving your career, as continuing it. Which brings me to our next point!

Career Growth

Freelancing: When you’re hustling to make ends meet growing your career may be the last thing you’re thinking about if you are even thinking about it at all. No one wants to be stagnant, but it can be difficult to find the time or resources to grow your skills and progress forward when you’re on your own.

Trusty Oak: Trusty Oak offers a chance to grow, learn and continue to build your career. From mentorship programs, to access to the latest software and tools (more on this below), to opportunities for growth and raises, you can expand your skills. When you become HubSpot certified, for example, you receive a pay increase — and a lot of new knowledge, too! This is important if you intend to go back into a full-time role in the future, or if you just want to be the best freelancer you can be.

Tools + Software

Traditional Freelancing: It can be hard—and expensive—to access software tools and resources when freelancing. These tools are pricey and often geared towards companies rather than individuals, meaning you don’t have what you need to get the job done. Or, perhaps you are finagling endless free trials (and creating endless free email addresses to do so) which is both time-consuming and annoying (hey, just speaking from experience here).

Trusty Oak: As a business, Trusty Oak has access to the latest software and applications - all free for you to use! We have major resources such as HubSpot, which means better productivity for you. It also allows you to stay abreast on the latest technologies and tools (remember that thing about growth I mentioned above).

Collaboration + Loneliness

Traditional Freelancing: While freelancing is flexible, it can also be lonely. Working for yourself also means working by yourself, and the absence of an office to go into or a team to work with is a major downside. This leaves you isolated (and out of luck) if you need help with a project, something unexpected interrupts a deadline, or you could simply use some feedback.

Trusty Oak: At Trusty Oak, we do things differently and you are part of a true team. You have access to a collaborative environment, and we help each other with feedback, sharing information and resources, and everything in between. We even collaborate on client projects sometimes! A team also means if you need some extra support, all of Trusty Oak is behind you. You are never alone. Trusty Oak’s collaborative environment is what makes us truly stand out and changes everything you knew about freelancing. This is absolutely my #1 favorite part about Trusty Oak.

Sound Appealing?

I think so. But maybe I’m a bit biased here. Trusty Oak has allowed me to pursue my dream of traveling the world while continuing to work and progress my career. I was initially drawn to Trusty Oak due to the stability and the chance to do high-level work, but have since fallen in love with the people and collaborative environment. I am sitting at a coffee shop on a beach 11,000 miles from my home as I write this while chatting with a Trusty Oak friend and preparing to start on a challenging project. So tell me, how could I not be biased?

Learn More About Working as a Virtual Assistant


Trusty Oak is expanding rapidly and always looking to add amazing new freelancers to our team. Check out our Careers page and see how you can join the team today!

About the Author

Katie Fishman

Katie is an experienced marketing professional with a background in marketing strategy and content creation. She has ample experience writing across formats and is often responsible for the final edit, proof, and review of items before publishing. Her marketing experience is encompassing and includes product marketing, social media, SEO, PR, and analytics. Katie is highly organized and detail-oriented. She enjoys learning, being challenged and taking on new responsibilities. Over the past 10 years, she’s worked in a variety of diverse industries including cruising/hospitality, finance, advertising, online privacy/security, and gaming. Katie’s passions include photography, swimming, writing (of course!) and traveling. She loves exploring new places, is frequently “on the road,” and maintains her own travel blog. Originally from Pennsylvania, Katie has lived in six states including Texas (Austin).

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