Knowing when it's time to hire help

I needed more support if I was going to scale up

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Support. It means to bear the weight of, to hold up, to give assistance to. So many of us land in the freelance world and feel like we’re on our own little islands, without help or support. But when folks start to approach burnout, I find that one of the big questions we need to ask is this: What support do you need?

For most of us, doing it alone is not sustainable.

In February, I noticed a massive influx of product review assignments from my clients. Because I was working part-time (and acting as the primary caregiver for my kids), I couldn’t take on more than a few of these assignments each month. Frankly, this felt frustrating. I was leaving money on the table, and I knew I could knock out the assignments fairly easily if I had the time or support.

I kept saying to my husband (who was locked into a 40+ hour per week healthcare job at the time): “Why don’t you just join my business?” It was a joke, but I was also wondering what might happen if he did leave his job. If you’ve been following along, you know that he did eventually take a leave of absence. And last week, we set up an LLC together. He’s not going back to his job!

In the midst of all this, I realized that I needed more help and support if I was going to scale up. Without my husband’s job, I needed to bring in between $15 and $20k per month (before taxes) to support my family. We have student loan debt, a mortgage to pay, and need to cover (expensive) childcare for two kids. When I discussed this high revenue goal with my therapist, I realized that I couldn’t do this by myself.

If you, too, are thinking about hiring help, ask yourself these questions:

Am I leaving money on the table?

If you’re turning down assignments often — especially well-paid, interesting assignments — you may be in a place where hiring an assistant could boost your revenue. You can hire an assistant for as little as $200 per month; often, paying $200 allows you to bring in several thousand dollars of extra work each month. This math is really scary for a lot of us, but it usually nets out to being worth it.

Alone, I can make about $12,000 monthly in my business without feeling burned out. But now that I have three people working with me, plus my husband’s help, I’m able to bring in $20,000 monthly without sprinting. I pay those 3 people a total of $2000/ month for their help. (Pro tip: Use Gusto for payroll!)

Are there tasks on my to do list that don’t require my specific expertise?

This one was challenging for my ego. Often, I encourage my clients to track all the work they do for a week. Write down everything from administrative work to strategy work. Then go back and honestly note which of these tasks MUST be done by you. At the outset, I struggled with this because I felt like I needed to do everything myself if I wanted it done right. But this just isn’t true. It’s okay for someone else to work on a project and hand it back to me at 80% completion. This saves me valuable time because all I have to do is polish the work!

While we all like to think of ourselves as unique and special, the reality is that so much of our work can be done by someone else.

If you do this exercise, I also want you to pay attention to the things that only you can do. For me, it’s content creation in my business. It’s writing journalism pieces that contain my by-line. And it’s coaching. Nearly everything else on my list can be at least drafted or started by someone else!

Do I have business or administrative tasks that constantly slip down my to do list?

I had a long list of tasks that would carry over on my to do list, week after week, without me touching them: Organizing documents and folders, turning coaching worksheets into beautiful PDFs, developing speaker decks, updating my website, transferring my coaching platform to a new CMS, and on and on. I tried to address these items but because they didn’t immediately generate income (and they didn’t have deadlines), I would end up de-prioritizing them.

This work is what I hand to my virtual assistants. Overall, the net gain has been massive for both my brand but also my brain — no more lingering to dos!

Am I itching for growth, or resenting administrative work?

Hiring help requires learning to be a manager. Even if you’re only working with someone for 10 hours per month — which is a great place to start! — you’ll have to learn to delegate. Since hiring help, I’ve built Trello boards, learned how to carve out Monday mornings to delegate tasks, and set up onboarding documents. Hiring help forces you to codify your processes, which is a huge benefit for any business owner. In short, it forces growth. You’ll need to level up and get organized if you want to bring someone else into your workflow. Hiring help will also mean that you can focus on more high-level, strategic tasks. Again, this is a huge career benefit.

Who to hire

This spring, I hired an editorial assistant. I also brought on a virtual assistant agency, and I’ve subcontracted work at times. Plus, my husband is now working within my business. Here’s what each person does, and how much I pay them: