The Trusty Oak Blog

Overworked and Unsure? There’s a Better Way to Hire a Freelancer

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This is part two 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. Read part one, “Exhausted and Lonely? There’s a Better Way to Freelance,” here.

Hiring a Freelancer: More Challenging Than It Sounds

Hiring a freelancer is an excellent option for a variety of businesses—and reasons! Whether you have a one-off project you need extra help with, are looking for support on tasks and don’t have the time or skill set, or are a small business owner not quite ready to hire staff, outsourcing can be the best way to go. For many, hiring a freelancer is an ideal option, and in today’s internet-connected world it’s an increasingly popular alternative to hiring employees.

This all sounds great, but once you’ve made the decision to hire a freelancer the hard part starts. Who do you hire? Where do you find this person? How do you select from thousands of nearly identical profiles online? How do you know the person is actually qualified, and that you can rely on them? You’ll likely find yourself sifting through sites, trying to vet strangers, and taking a risk on someone you know next to nothing about. This can be daunting, time consuming, and downright scary out on the web!

The Trusty Oak Difference

The good news is, finding a reliable freelancer doesn’t have to be this overwhelming or risky when someone else does the vetting for you. Out there in the sea of job sites, embellished resumes, limited skill sets and so many unknowns, there is another solution— I’m talking about Trusty Oak, here! Below we take a look at some common freelancing drawbacks and show you how Trusty Oak offers something different than the norm.

Finding a Freelancer

Traditional Outsourcing: While ideally you would hire a freelancer you know personally or through a referral, it can be incredibly hard to find a connection with the right skills when the time comes. So, more often than not, your outsourcing search will take you online. When you hire a random person there is an inherent level of risk involved. Not only must you vet their skill set, but it’s hard to know if they care about their work (and by extension, your business), or if they just care about the money and little else. Furthermore, if they don’t care they won’t have qualms about dropping the ball—either slipping on deadlines, or even the dreaded “going dark” scenario where they disappear mid-project.

Trusty Oak: Trusty Oak is an actual company, who contracts with dozens of freelancers (and counting!) We’re a team of real people, with real accountability, who really care about the work we do. We aren’t just trying to make a fast buck, but instead view Trusty Oak as part of our career. Each and every freelancer cares about you and your business as well as the work they do. Think of us as a group of passionate professionals with accountability. We check-in with both our client success managers (more on this coming up) and team frequently, so you never have to worry about us disappearing.

Skill Sets + Support

Traditional Outsourcing: When you hire a freelancer, they often have a specific set of skills— say, content writing or graphic design. While this ensures they are great at one thing, it can get problematic when projects expand in scope, or when you realize you could use help with more than you originally thought. This results in you either having to pick up the slack and do the work yourself or having to hire a second freelancer (and conduct a second time-consuming and frustrating search). It can also be tricky to coordinate between new hires and keep everyone’s projects straight. 

Trusty Oak: All of our freelancers have robust and expansive skill sets, and are able to help with a variety of tasks. More than that, we are a team! If your VA is helping out with writing when suddenly it becomes clear you need help with design, no problem. When you hire Trusty Oak, you hire the entire team, meaning even if your VA doesn’t have a skill, they can reach out to our team and get that task covered with no extra work for you. You’ll have access to this large pool of talented and qualified people, not to mention we coordinate with one another, reducing logistical time and stress on your end.


Traditional Outsourcing: It can be tricky to vet people when hiring in-office for a full time role, and this task becomes infinitely more difficult when you’re hiring freelancers off the internet who you may never meet in person. In an ideal world people would always be honest, but unfortunately, sometimes people misrepresent their skills. That fact aside, the sheer number of sites, profiles and descriptions out there are overwhelming. Even if you spend a great deal of effort vetting, it can be hard to find the right match. Hiring the wrong person can be frustrating at best and a disaster at worst, and not a good use of your precious time or money.

Trusty Oak: All Trusty Oak VAs are highly qualified and vetted. They go through a rigorous hiring process, just like with any full time job. They apply with a resume and cover letter, and conduct a series of interviews—the final being a video interview with Trusty Oak’s CEO and Founder, Amber Gray. References are checked, skills confirmed and validated—meaning you get someone who can actually do the work they say they can. What’s more, our VAs are rewarded for continuing education like getting certifications related to programs and methodology that will help better serve you! 


Traditional Outsourcing: With traditional outsourcing, you interact with one person and one person only—the freelancer. While this is simple, it can also become problematic when an issue, concern, or question arises. Without any sort of leadership to approach, if you have a problem, there’s often little you can do about it.

Trusty Oak: Trusty Oak employs client success managers dedicated to ensuring our clients get what they need. These client success managers check in with our clients frequently, and are available as a resource when you need some support or have an issue to discuss. Our leadership is also easily accessible, too, and our founder is highly involved.

Growth + Scalability

Traditional Outsourcing: Sometimes (ok, who are we kidding, oftentimes) a project you thought was quite simple or straightforward changes scope. Alternately, as your business grows, you find you need more support. While this is exciting stuff, it also means that dreaded search for a new freelancer task begins all over again.

Trusty Oak: Scaling up—whether it’s for a one-off project or to support your growing business—is no problem! While some of our clients work with only a single Trusty Oak freelancer, many employ their own team of dedicated virtual assistants. Trusty Oak will create a collaborative group to help you succeed, with support available for as many hours and tasks as you need. We are based on a tree, after all, so growth is something we do well. 

So there you have it, just a few of the many ways Trusty Oak is different, and dare I say better, than traditional outsourcing. Sound good to you? Want to get started? Contact us today!


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).