In a perfect world, we’d all have a right-hand man who could take on our least favorite tasks. But, in reality, most of us get far too busy and exhausted before we ever ask for help — and some of us don’t realize it until it’s too late.
Hiring an assistant can feel very risky. Will they be reliable? Will they cost too much? Will training and managing them become a chore in itself? Here’s some advice to determine if you’re ready, and help you make the right hiring decision once you are.
What is a virtual assistant?
A virtual assistant (VA) is someone who supports you remotely. Like a personal assistant, a VA can help with scheduling, correspondence, and general administrative duties. They can also help with personal affairs, like calling in dinner reservations.
Some assistants specialize in specific areas, like:
- Executive Assistants: Focus on high-level administrative tasks, like managing your calendar, coordinating meetings, and acting as a gatekeeper for your time. They may attend meetings alongside you (or on your behalf) to take notes and they might even travel with you to important conferences and events.
- Marketing Assistants: Help with digital marketing tasks, like creating content, managing your social media accounts, or overseeing your email newsletter. They can also help you plan and fine-tune your marketing strategy.
- Technical Assistants: Specialize in tech-related tasks like website updates, software management, and troubleshooting. They also make great general assistants to developers, engineers, and IT personnel.
- Creative Assistants: Handle duties like graphic design, video editing, and branding. They can help you maintain a consistent brand image or design graphics for your social media and blog posts.
Whether you need a jack-of-all-trades or a specialist who complements your skill set, the best virtual assistants are flexible, fast-learners who are eager to learn and grow alongside you.
Are you reluctant to let go?
Early in my career, I was writing content until my eyes crossed each day. I was exhausted and grumpy with a constant neck ache, and I felt completely stuck. After all, my clients hired me to write their content, I couldn’t outsource that! And the things that weren’t getting done, like responding to inquiries, didn’t really matter because I didn’t have the bandwidth for more work anyways… right?
Oh, I could kick myself. An assistant could’ve handled so many crucial tasks for which I never set aside enough time. Things like final proofreads, finding (better) opportunities, delivering documents, summarizing feedback, and setting deadlines.
They would’ve given me much-needed breathing room to finally start shifting to a business model that didn’t rely entirely on my hands-on involvement.
But, what happened instead? Everything came to a head at once: Industry changes I never had time to get ahead of, new personal obligations that couldn’t be ignored, and using up the last of my tolerance for soulless SEO content.
After taking many unexpected months off, I eventually realized that, in some roundabout way, I finally had time to do what I should’ve been doing all along: Working on my business instead of in it — but I had to make up for a lot of lost time.
Thanks to the endless support of my now-husband, things worked out for me. But I’ve met countless women who were up to their eyeballs in to-do lists for so long that key opportunities passed them right by, and they were never quite able to find their footing again.
My advice? The consequences of hiring an assistant too early are minimal; worst case, you simply part ways. But the consequences of hiring one too late can be catastrophic for your business, sanity, and livelihood.
- Self-Sabotage & Success: Defeating Your Upper Limit
Signs You're Ready for An Assistant
If the below scenarios resonate with you, that’s a strong indicator that it’s time to get help:
You’re turning down opportunities. You’re so busy with your current obligations that you’re unable to focus on new clients, projects, or ideas that could grow your business.
Your days don’t seem long enough. You add more things to your to-do list than you’re checking off each day. You have big ideas but no bandwidth to execute them.
Things are slipping through the cracks. You’re missing deadlines, making errors, or forgetting stuff. You don’t have time to put on that special finishing touch.
Your work-life balance is suffering. You feel like you’re working seven days a week. Even when you take breaks, work dominates your mind.
You’re procrastinating stuff. You keep putting off tasks you dislike or don’t know how to do, and they’re piling up. You feel so overwhelmed that you end up not working efficiently.
You’re working in your business, not on it. You see the same key moves like “start a newsletter” or “create a 9-grid” lingering on your to-do list week after week.
How much does a virtual assistant cost?
For an entry-level VA based in the United States, rates start at $15 to $17 per hour. If you’re looking for a more experienced or specialized assistant, rates can be as high as $55 an hour.
If you have a fairly consistent workload, you may be able to negotiate a daily, weekly, or monthly rate to keep your costs predictable. Alternatively, you can set time limits each week to make sure your assistant never surprises you with a huge bill.
You could secure an entry-level assistant for less than $500/month if you only need them for one to two days a week. There are also fractional support services that can take your costs even lower — more on that below!
Questions to Ask Yourself
Don’t get me wrong, bringing an assistant on board is not a magical fix for your business. If you don’t use the extra help strategically (in a way that will help you sustainably grow), you’ll eventually find yourself right back where you started: Overwhelmed with work that doesn’t fill your cup.
Here are some questions to get you thinking about how an assistant can bring real value to your business, and what you would do with your newfound free time.
What is the extra help really worth?
Think beyond the monetary value of the extra hours an assistant can free up in your schedule. Instead of asking how much more work you could take on, ask yourself: How much more intentional and effective could you be with their support?
Would delegating tasks like responding to emails or sending invoices create a noticeable difference in how others perceive your professionalism and responsiveness?
How would it feel to know the back-end operations of your business are being handled for you?
When life throws uncertainties your way, what would it mean to have someone in your corner who truly understands your business? Could their ability to step in — managing your inbox, rescheduling meetings, and keeping things running smoothly — give you the security to take necessary breaks without fear of losing momentum?
- Why Your Business Needs a Fallback (and How to Get One)
Do you need to reimagine your business model?
If your business relies on your unique involvement, it might be time to reconsider that model or look into creating additional income streams that can run without you. A virtual assistant can create downtime in your schedule so you’re able to do just that.
Of course, not every business model is designed to remove you from the core work. But, even as an artist or creative, there are still plenty of tasks a virtual assistant could take off your plate, giving you more time to hone your craft. In the long run, that means you’ll unlock more opportunities, demand higher rates, and (hopefully) achieve a better work/life balance.
Try to 10-10-10 it: Think about where you could realistically be in your business 10 days, 10 weeks, and 10 months from now if you hire an assistant versus if you don’t. What setbacks and opportunities might come your way and how would you handle them in either scenario?
Are you planning to outsource the right things?
Anything you don’t like, aren’t good at, or won’t miss could be outsourced. If you haven’t already, identifying where your work-related duties fall within the four zones of work could help you quantify just how much can be taken off your plate.
The incompetence and competence zones mostly consist of “busy work” that’s easily outsourced, but once you start looking at your Zone of Excellence, you’ll realize that a lot of work you think is meaningful could actually be passed to an assistant too.
Here are some activities I used to feel obligated to do myself, but soon realized my assistant could do just as well:
- Writing SEO snippets and alt tags for my blog
- Repurposing my blog posts for social media
- Responding to non-client emails and DMs
- Finding interesting pitch requests every week
- Keeping my spreadsheets and reports up-to-date
Outsourcing these things gave me even more time to focus on my Zone of Genius, which encompasses all the activities that I’m uniquely positioned to do and truly passionate about.
Where To Hire An Assistant
Here are a few popular places where you can find an assistant and some aspects to consider when deciding which one is best for your needs.
Freelance Platforms (like Upwork)
Upwork is the largest freelancing platform and my favorite by far. It has experts from all over the world, but you can narrow your search to only include people in your country or timezone. It’s easy to hire someone on a fixed-fee or hourly basis, and you can set weekly caps on the contract.
- Negotiate rates and availability directly
- Built-in escrow service to manage payments
- Give raises and bonuses as you see fit
- Conflict resolution team to handle disputes
- Option to hire your assistant outside of Upwork
- Sifting through proposals can be very time-consuming
- Your assistant can quit at anytime, without notice
How it works: Post a job outlining the key tasks and skills and freelancers will submit proposals introducing themselves. You can check reviews, work history, and hourly rates; message applicants with questions; or schedule video calls with your top picks before deciding who to hire.
- How to Successfully Hire on Upwork
Fractional Assistants (like Zirtual)
Instead of finding and managing an assistant on your own, a fractional platform like Zirtual or Boldly lets you subscribe to a fixed-rate package where you can use one of their specialists for up to X number of hours per week. This approach ensures you have reliable, scalable support while keeping costs predictable.
- Easy, secure payments
- Screening and hiring is done for you
- Replacements are handled for you
- Support team for questions and concerns
- Package prices are set by the platform
- No option to give raises or bonuses
- It's prohibited to hire your assistant directly
How it works: Pick a platform, choose a package (based on # of hours), and describe what you need. The platform will match you with a qualified assistant from their pre-vetted talent pool and help you kickstart the relationship.
Networking Groups (like r/VirtualAssistant)
While pretty informal, your personal network, dedicated Facebook groups, and subreddits can be fantastic resources. If you have questions or need a recommendation for a specialized assistant, there’s really no better place to look.
Not only do virtual assistants advertise their availability in these places, but you’ll also find ratings and reviews from other business owners. Plus, they often contain a wealth of lessons, advice, words of caution, and stories.
If you go this route, do your due diligence. I’d highly suggest using an escrow service (at least for the first few months) and using the right type of contract to protect your interests.
Local Platforms (like TaskRabbit)
Ever need assistance with physical, location-specific tasks? Platforms like TaskRabbit connect you with local helpers (“Taskers”) who can do all sorts of things for you, like returning packages, distributing flyers, scanning in your boxes of old family photos, or even making dinner.
Just describe the tasks you need completed, along with any deadlines or constraints. Taskers in your area will apply and you get to choose based on reviews, pricing, and experience. And, TaskRabbit is there to mitigate if there are any issues.
A perk of TaskRabbit is that you can hire a person once, occasionally, or on an on-going basis. You can also try Craigslist, Nextdoor, or a local Facebook group to find an assistant near you.
Setting Up For Success
The first day with your new assistant can be a little overwhelming, especially if you haven’t hired anyone before. Here’s some advice to get your relationship started off on the right foot.
Accurately Estimate The Workload
Think about the recurring responsibilities that eat up your day. How much time do these tasks take you, minus procrastination and distractions?
For the most accurate estimate, keep a time diary this week to track how long you’re really spending on the tasks you plan to outsource. Then, decide if they need to be done every single day, or if they can be lumped together to create one or two longer work days for your assistant each week.
If you plan to hire someone on an hourly basis, one thing you should avoid at all costs is overestimating the workload. If someone thinks they’ll be getting 30 hours a week and you end up only having enough work to fill 15, they may decide it’s not worth their time — and that means you’ll have to hire someone all over again.
Figure Out An Optimal Schedule
Think about your ideal schedule and whether your assistant needs to be in alignment with it. Do you need them around when you’re up and working or can their tasks be done during more flexible hours?
Also consider the level of commitment you expect from your assistant. Would you prefer someone who checks in with you daily? Weekly? Do you want them to send you an email summary or take the time to hop on a call with you? Check-ins will need to be coordinated with both of your schedules.
Treat It Like An Investment
Don’t look at your assistant’s fees as a line item that you aim to keep as low as possible. If you’re a great boss, they’ll grow alongside you and become extremely trustworthy and dependable. Paying them fairly from the start sets the tone for a great relationship, and it shouldn’t end there.
Plan for annual raises to keep up with inflation and show that you value their continued contribution to your success. Also, don’t underestimate the power of a bonus — it’s a wonderful way to express your gratitude when they go above and beyond. A heartfelt “thank you” goes a long way too.
Know Your Tax Filing Requirements
You’ll probably hire your assistant as an independent contractor, which means they’ll manage their own taxes, but you may still need to give them a form.
In the United States, you’re required to issue a 1099-NEC to your assistant if you pay them more than $600 during the tax year. Ask them to fill out a W-9 form to give you essential info (like their Taxpayer Identification Number) so you can complete their 1099.
However, if you’re using a middleman like Upwork to process payments, you won’t need to fill a 1099-NEC at all. If your assistant meets the reporting thresholds, Upwork will issue a 1099-K straight to them — you won’t need to be involved.
- A Simple Guide to Small Business Taxes
Maintain Good Documentation
You can train your assistant on tasks by writing them down, making screen recordings, or hopping on a video call. In all cases, it’s a good practice to ask your assistant to create formal documentation as they learn new processes.
As you’re training, give context. Why is the task important? Why have you arrived at this particular process? Is it important that the task is done this way, or can they arrive at their own method? This gives your assistant a better understanding of your business.
Also, make it known when a shortcut is possible or encouraged. For example, maybe you’re open to email filters or automations, but you’ve never had time to set them up. Just make sure your assistant updates your documentation when they find optimizations.
Protect Your Accounts & Privacy
Safeguarding your sensitive info is crucial, especially when you’re still forming a relationship with your assistant. Here are some precautions I strongly suggest taking:
Use a password manager like LastPass or 1Password. These tools allow you to share credentials without revealing your actual passwords and give you the ability to revoke access at any time.
Use a virtual card service like Privacy.com if your assistant needs to make purchases on your behalf. You can create one-time-use or merchant-specific cards with spending limits.
Look for a bank account with role-based access if your assistant will need to review statements or reconcile transactions within your account.
If you haven’t already, set up 2FA on your personal accounts and make sure the verification code isn’t sent to an email your assistant can access.
Don't Overload Your Assistant
Once you have an assistant, it might be tempting to offload every little task that’s weighing you down. But, before you add something to their to-do list, ask yourself: “Does this really need to be done at all?”
Treat your assistant’s workload as a precious resource. Overloading them can lead to burnout, mistakes, and missed chances to focus on higher-value tasks. Be mindful about how you allocate your assistant’s time.
Keep Apps & Tools to a Minimum
Resist the urge to add task/project management or messaging platforms to your workflow. You don’t need to jump into systems like Asana, Monday.com, or Slack unless your business has outgrown simpler (and free) options.
Honestly, you don’t need anything fancy. I know a woman who manages her entire life, six-figure business, and three assistants using Google Calendar alone — and it works!
Don’t fix what isn’t broken. Use what’s intuitive and familiar to you; your assistant will adapt to your systems and processes quickly enough.
What's Next?
If you’re ready to spend more time in your Zone of Genius and let go of the other stuff, bringing an assistant into your corner might be the move. While this transition may be as scary as it is exciting, I think you’ll grow to love it!
If you’re really still on the fence, consider a trial hire. Set aside a few hundred dollars and bring someone on board for just two weeks. See if it makes a noticeable impact on your focus, mindset, and schedule. Had I done that all those years ago, I’m certain it would’ve gotten me unstuck and on track to building the business I love today.
- Identifying Your Zone of Genius
- Self-Sabotage & Success: Defeating Your Upper Limit
- Choosing a Business Structure: LLCs & Other Options
- A Simple Guide to Small Business Taxes
- Why Your Business Needs a Fallback (and How to Get One)
