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When Should You Hire Your First Employee?

Outside photo of woven hat with dark blue bow and small white basket of blueberries tipped over spilling out on a white cloth laid on the grass

I used to try to do everything on my own… web design, bookkeeping, graphic design, etc. It was so overwhelming and completely exhausting. In my mind it was like I had to do everything myself and waited way too long to hire my first assistant because I kept psyching myself out.

Is it time to hire help for your small business? 

If any of these scenarios sound familiar, it’s time to strongly consider hiring an independent contractor or employee:

  • You need more time and space to create new products and grow your business.
  • Your work/life balance is constantly out of whack.
  • You’re overwhelmed + stressed because you’re spending so much time on tedious tasks.
  • You spend too much time doing things that aren’t bringing in $$$.

But wait! Knowing it’s time to hire someone and being ready for it are two totally different things, especially when it’s your first time outsourcing work. First there’s all the icky feelings that get in the way, “I can do it myself! Nobody’s going to do it like I do!” Then there’s the lies we tell ourselves, “It’s going to take so much time to train someone, I may as well do it myself.” And lastly, there’s the whole money-out-of-my-pocket thing, “I don’t have the budget for this yet!”

Well, I’m here to tell you that there’s NEVER going to be the perfect moment, and it'll be difficult to build a team if you keep that mindset. If you can part with a few hundred bucks (business expense!) for a training, conference, or workshop, then you can part with a few hundred bucks for an assistant. Getting things done is infinitely more valuable at a certain point than investing in education (again).

Get your free 'Planning for Your First Hire' workbook here.


You know what’s really motivating for getting your products launched and bringing in new clients? The need to pay someone other than yourself. You’re not going to miss a payment to your employee, right? How embarrassing! (Not to mention, they won’t stick around for long if you do that.) Being accountable for taking the financial hit is a pretty good incentive to get things done and generate more revenue.


Some of us really struggle with raising our prices and asking for valuable compensation. Once you start increasing your overhead with a team, you’re going to need more revenue to cover those expenses. Much of that will come from new products and new business, but it’s also an opportunity for you to evaluate your current rates and increase them if they’re too low to be sustainable.


You can step away from your business and it will be OK! If you’re attending a conference, planning a vacation, or getting away for a long weekend, you’ll be able to enjoy yourself because someone else is taking care of the day-to-day.

If you feel “too small” to allow yourself this freedom, think of it this way… giving yourself permission to step away from the parts of your business that drag down your energy is good for your creativity.


Being a solopreneur is lonely. You’re the one coming up with all of the ideas (and probably validating them, too, within your very small bubble). Building a team pushes you out of your comfort zone… it suddenly opens your business up in a way that nobody else is likely to see. With that vulnerability comes the opportunity for great collaborations.

That eCourse you were designing on your own? Well your graphic designer can make it better, and your copywriter can make the headlines snazzier, and since they had their hand in creating it, they’ll gladly share it with their own audiences, growing your bubble *that* much more.

Ready to hire? Get an independent contractor agreement.

Something holding you back from hiring? Let’s talk about why in the comments.

Just starting and not even thinking about hiring someone yet? Learn how you can seem like a pro, even if you’re just starting out.

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